Retired-ish: Recent Episodes
Cameron Valadez
Retired·ish is the retirement podcast for those exploring retirement and those currently in retirement. The retirement ideas and strategies discussed are focused around preparing for one of life's biggest transitions, and how to preserve the wealth that you have worked so hard to achieve! This educational podcast was created to provide you with confidence in your retirement planning decisions. Your host, Cameron Valadez, is a CERTIFIED FINANCIAL PLANNER(TM) and partner of financial planning firm for retirees, Planable Wealth. In each episode, Cameron shares actionable ideas and strategies to help you Simplify Investing, Reduce Taxes, & Grow Your Net Worth, so you can retire on your terms! Cameron will answer some of the top concerns of retirees including: How can I potentially pay less in taxes to the IRS? How can I better preserve my retirement nest egg and draw a sufficient income? How can I simplify my investments? How can I keep more wealth in the family? Cameron also takes a deep dive into more complex issues retirees face regarding retirement income, estate planning, Medicare, Social Security and more! Retirement doesn't have to be a means to an end. To be Retired-ish means to have the CONFIDENCE and FREEDOM to spend your time on what matters most, and retire on your terms! Cameron believes this can be achieved through well-designed financial planning that adapts to life's unknowns. Find more information about Cameron or ask a question you would like answered on the podcast by visiting retiredishpodcast.com Want even more detailed retirement planning insights? Join our monthly Retired·ish Newsletter!
Five people. Five completely different net worths, ages, and family situations. And every single one of them is sitting on a stock position that's grown so large it's now the single biggest risk in their financial life. In Part 2 we're taking the strategies we learned about in Part 1 of this mini-series and we're running it through five real case studies with real numbers, so you can see exactly which strategies fit different situations, and more importantly, why the "obvious" answer is wrong more often than you'd think.
More specifically, I discuss:
- 5 case studies for diversifying and managing taxation
- Selling stock, direct indexing and using charitable giving strategies
- Avoiding unnecessary taxation from mutual funds
- Diversifying after utilizing the Net Unrealized Appreciation (NUA) strategy for stock in 401(k) and ESOPs
- Managing continuing awards of Restricted Stock Units (RSU)
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Ask a Question
- Get Show Notes Here
Key moments:
(02:20) Case study 1: Combine selling, direct indexing, and charitable tools
(11:40) Case study 2: Sequence charitable giving and direct indexing
(16:16) Case study 3: Avoid unnecessary taxation from mutual fund distributions
(24:24) Case study 4: Use NUA and patient diversification
(33:28) Case study 5: Manage a moving target of employer equity
(40:30) Match diversification to each person's timeline and goals
(42:38) Prioritize diversification over avoiding taxes
You've watched one stock turn into more money than you ever expected. And now you can't bring yourself to sell it — because the second you do, the IRS gets a check with a lot of zeros on it and you come to the realization that you are not going to receive all of that money you've been looking at on paper all these years.
But on the flip side you're also wondering how that money can change your life and all the things you can do for you and your family.
In this episode, we're talking about what that fear of taxation can actually cost you, and some ideas to help you take risk off the table and mitigate the inevitable tax bill.
More specifically, I discuss:
- Why a concentrated stock position carries more risk than you think
- Worry more about taxes from selling or a sell off in your biggest stock position?
- Strategies to defer taxes or diversify a concentrated stock position
- Direct indexing and exchange funds
- Opportunity zone funds
- Charitable giving strategies for large, embedded stock gains
⏱️ Chapters:
(04:09) Why a concentrated position is sneakier than it looks (09:37) Which is the bigger threat: taxes or concentration risk? (11:41) Thought experiment: selling today vs. waiting and potentially losing value (14:46) The biggest misconception: taxes vs. concentration risk (17:35) Strategy 1. Just sell it (18:56) Strategy 2. Hold on to it until death and receive the step-up in basis (21:10) Strategy 3. Gifting to family (25:23) Strategy 4. Direct indexing (31:04) Strategy 5. Charitable giving
Resources:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
The market just dropped. Your IRA or 401(k) is down bad. And your gut is telling you to do something about it.
The problem is, most of the things people instinctively want to do when the market tanks are exactly the wrong moves.
But buried inside that volatility — if you know where to look — are some of the best retirement and tax planning opportunities that exist. Opportunities that only show up when things get really scary.
In this episode, Cameron walks you through some of those opportunities and explains where people blow it so you don't make the same mistakes.
More specifically, I discuss:
- What kind of market volatility constitutes executing a particular strategy?
- The ideal Roth conversion timing during market downturns
- What can you do about Required Minimum Distributions (RMD) if your IRA or 401(k) drops significantly?
- Net Unrealized Appreciation (NUA) "basis reset" for those with company stock inside their 401(k) plan
- 72(t) payment plans from your IRA and how to mitigate the damage during market downturns
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key moments:
(03:21) Roth Conversions: The Silver Lining
(14:14) Required Minimum Distributions (RMDs) During Market Declines
(18:39) Net Unrealized Appreciation (NUA) Strategy
(22:39) NUA: Capitalizing on Downturns and Avoiding Pitfalls
(26:23) 72(t) Payments: Early Withdrawal Strategies
(32:28) Common Mistakes to Avoid
Divorce is never easy. But divorce after 50? That's a completely different animal.
We're talking about decades of accumulated assets, retirement accounts, Social Security decisions, healthcare coverage, and tax consequences that can follow you for the rest of your life — and one wrong move can cost you far more than just the marriage.
In this episode, we're breaking down the real financial damage of what's called "Gray Divorce"; the mistakes I see people make in practice, and exactly what you need to do to protect yourself.
More specifically, I discuss:
- Gray Divorce Study – What Divorcees are saying about retirement and finances post-divorce
- The difference between divorce after 50 versus divorce in your 30s and 40s
- The differing realities of men vs. women post-divorce
- Mistakes during and after the divorce process regarding retirement savings
- Social Security and healthcare decisions post-divorce
- Making key financial decisions under pressure and common regrets
Key moments:
(03:04) Uncertainty in Retirement Planning for Divorcees
(06:38) Retirement Savings Mistakes
(11:11) Financial Blind Spots and Costly Decisions in Divorce
(14:27) Social Security Claiming Risks Post-Divorce
(21:11) Health Insurance Decisions Post-Divorce
(24:40) Seeking Professional Financial Guidance During & After Divorce
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
You wake up everyday, check your bank account on your phone, and you see all your money sitting there, just as it was the day before. How do you feel? Pretty good, right? That number hasn't moved. It's exactly where you left it. Safe.
Here's the problem: that money is slowly disappearing even though you can't tell by looking at your bank app. This is because every single day, the purchasing power of that money is quietly shrinking. The things you will actually buy one day with those dollars — groceries, gas, insurance, healthcare — are getting more expensive. But your balance stays the same, so it feels fine. However, it's not fine.
That is inflation. And most people will go their entire lives without sitting down and doing the math on what it actually does to their money over 20 or 30 years and take it seriously because we're too busy watching Netflix and wasting time wondering how our neighbor could afford that nice new car.
In this episode, we're explaining the two best — and in my opinion, the most effortless — ways to fight back against inflation to make sure that your money keeps up with rising prices, because let's be honest, they're never going to start trending backwards.
More specifically, I discuss:
- Why is inflation for so important and how can it damage a retirees' financial life?
- What is the rate of inflation?
- Different types of inflation
- How does inflation affect retirement accounts? What about cash in the bank?
- Effortless inflation hedge #1: fixed-rate debt + home ownership
- Effortless inflation hedge #2: the primarily equity investment portfolio
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key moments:
(03:26) Understanding Inflation's Impact
(07:09) The Illusion of Cash Safety
(09:42) Fixed-Rate Debt as an Inflation Hedge
(14:48) Addressing Homeownership Objections
(20:28) Equity Portfolio: The Best Hedge
(23:08) The Power of Compounding Equities
(25:16) Equity Liquidity and Flexibility
(29:20) Long-Term Investing Discipline
(33:37) Combining Strategies for Resilience
(35:00) Final Takeaways
My firm, Planable Wealth, is currently very busy in the midst of our Spring Strategy Meetings with clients where we help people just like you create and retool their financial and tax plans for 2026 and beyond. That said I wanted to bring you an encore episode this week, which I think, is one of the core episodes we've done so far
Back in episode 70, I discussed the importance of retirement income and the realities of your cash flow in retirement. I also share my thoughts on dividend investing especially when trying to utilize dividends as an income stream in retirement.
Income planning will make or break your retirement years - This is because your income in retirement will be what controls your lifestyle, not your net worth.
When doing your pre-retirement planning - hopefully several years before your desired retirement - you'll want to match your lifestyle wants, needs, and goals with the income you are able to generate from your various financial assets and resources – but, depending on where you generate income from, you may run into certain hurdles along the way.
In this episode we break down the important pillars of retirement income planning, matching your income sources to your retirement goals, and why a dividend income strategy may not be the best choice.
Thanks for being a loyal listener and we'll be back with new episodes soon.
More specifically, I discuss:
- Defining retirement income planning
- The 2 major pitfalls you need top watch out for when creating your retirement plan
- Investment returns or income?
- Potential cons of a "probability-based" retirement plan
- Wade Pfau's Four L's of Retirement
- Matching your various retirement income sources with your goals
- Potential issues when relying on only one income source such as real estate or dividends
- The importance of dividends
- A pure dividend spending strategy isn't a great retirement income strategy
The Key Moments In This Episode Are:
(02:43) The Error of Relying Solely on 1 Retirement Income Source
(03:39) Challenges of Basic Income Planning
(06:03) Retirement Income is More Important Than Investment Returns
(09:15) The Four L's of Retirement Planning
(11:57) Funding Your Desired Lifestyle
(13:09) Rental Real Estate May Not Be The Most Efficient Retirement Income Plan
(15:35) Planning for Legacy, or Not
(16:46) The Importance of Liquidity in Retirement
(18:42) The "Live Off Of Dividends" Strategy Debate
(25:25) The Risks of High-Dividend Paying Stocks
(30:36) Total Return Investing as an Alternative
Resources:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
You worked hard your whole career, you saved, you did everything right — and now you're on Medicare and you get a letter from Social Security telling you that you owe hundreds of dollars extra every single month in premiums just because you made too much money!
No warning. No opt-out. Just, what looks like punishment for doing a good job and setting yourself up for retirement.
That's IRMAA. And what most people don't know is that in certain situations, you can fight back — and win.
Today we're breaking all of it down. The real numbers, the real rules, and exactly how to use the appeal process strategically if you qualify.
More specifically, we discuss:
- What is Income Related Adjustment Amount (IRMAA)?
- How to calculate what your potential Medicare premium surcharges will be
- Common situations that cause Medicare enrollees to be subject to IRMAA surcharges
- When and how can you appeal IRMAA surcharges on your Medicare premiums?
- Practical tips when appealing IRMAA surcharges
- Strategies to avoid IRMAA surcharges
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
Key moments:
(02:56) IRMAA Medicare Premium Surcharges: How it Works
(05:50) Calculating Your MAGI (Income) for IRMAA
(09:27) IRMAA Brackets and Cliff System
(17:37) Common IRMAA Medicare Premium Surcharge Triggers
(23:07) Appealing IRMAA with Form SSA-44
(26:52) IRMAA Appeal Example Scenarios
(31:37) Non-Qualifying Events for IRMAA Appeal
(40:02) Practical Tips for Filing an IRMAA Appeal
(41:00) Strategies to Avoid IRMAA
(46:51) Listener Question: IRMAA appeal for deferred compensation
Your spouse works at a major publicly traded company. You're going through a divorce. And somewhere in their compensation package are restricted stock units or RSUs — awards of shares of company stock that haven't even vested yet.
Are you supposed to receive stock? Are the RSUs considered income? Are they both? How much are we actually talking about here?
By the end of this episode, you're going to understand Restricted Stock Units (RSU) and how they are commonly handled in a divorce so you can be better prepared!
More specifically, we discuss:
- What are Restricted Stock Units (RSUs)?
- Dividing RSUs in a Divorce
- Characterizing RSUs as Income or Assets
- Determining RSU Community Property and Separate Property
- Commonly Used Formulas for Splitting RSUs in California
Key moments:
(00:00) Introduction
(00:59) What are Restricted Stock Units (RSUs)?
(04:37) RSUs vs. Stock Options
(07:02) Understanding Vesting Schedules
(09:14) Companies that Offer RSUs
(11:45) Dividing RSUs in a Divorce
(13:15) Characterizing RSUs as Income or Assets in Divorce
(16:11) Unvested RSUs at Date of Separation (DoS)
(17:36) Determining Community Property and Separate Property for RSUs
(20:32) Commonly Utilized Formulas for RSUs in California Divorces
(27:48) Practical Example: Jim and Rachel Johnson
(33:52) Important Information to Gather Regarding RSUs In The Divorce Process
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
You just came into a large sum of money. Could be an inheritance, a business sale, a 401(k) rollover. And now you're paralyzed trying to figure out when to invest it.
Do you invest it all today? Spread it out over six months? A year? Wait for the markets to drop or the perfect opportunity to cruise by?
In this episode, Cameron summarizes what the research actually says, and more importantly—when the math matters and when it doesn't.
More specifically, we discuss:
- What is Dollar Cost Averaging (DCA)?
- The Problem With Dollar Cost Averaging
- Vanguard's Research on DCA vs. Lump Sum Investing
- What If You End Up Investing "At All Time Highs"?
- How To Decide Whether or Not To Invest The Lump Sum or DCA Over Time
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
- 2012 Vanguard: "Dollar-cost averaging just means taking risk later" https://static.twentyoverten.com/5980d16bbfb1c93238ad9c24/rJpQmY8o7/Dollar-Cost-Averaging-Just-Means-Taking-Risk-Later-Vanguard.pdf
- 2023 Vanguard: "Cost averaging: Invest now or temporarily hold your cash?" https://corporate.vanguard.com/content/dam/corp/research/pdf/cost_averaging_invest_now_or_temporarily_hold_your_cash.pdf
- Vanguard Summary Article: https://investor.vanguard.com/investor-resources-education/news/lump-sum-investing-versus-cost-averaging-which-is-better
- Kitces Article: "Dollar Cost Averaging Manages Risk But Reduces Returns" https://www.kitces.com/blog/dollar-cost-averaging-versus-lump-sum-how-dca-investing-can-manage-risk-but-on-average-reduces-returns/
Key moments:
(00:00) Invest All at Once Or Gradually Over Time?
(01:16) What is Lump Sum Investing vs Dollar Cost Averaging?
(05:18) The Math Problem with Dollar Cost Averaging
(07:35) Vanguard's Research on Lump Sum Investing vs Dollar Cost Averaging
(11:27) The All-Time Highs Myth
(16:07) The Impossibility of Being Right Twice
(18:44) Three Questions to Ask Before Investing a Lump Sum
(23:02) A Hybrid Approach to Investing a Lump Sum
(27:03) A Hierarchy for Investing a Lump Sum
(28:38) Get More Useful Information
If your aging parent owns a home and they are reaching the point in life where their physical and or mental health is rapidly declining and they need additional care, there is a clock ticking on decisions that most families don't even know they need to make.
And those decisions — specifically, what to do with their house and how to fund their care— carry tax consequences that can either preserve tens of thousands of dollars for the next generation or quietly hand it to the IRS. Typically, the responsibility of figuring all this stuff out lands on your shoulders.
In this episode, Cameron walks you through a real-world case study, step by step, so you can see exactly how this can play out while minimizing taxes as much as possible and funding their care.
More specifically, we discuss:
- What are the tax ramifications of selling the home to fund long-term care?
- What are the tax ramifications of renting the home to help pay for care?
- What are the tax consequences of staying in the home and paying for care?
- Utilizing a Multiple Support Agreement to obtain tax deductions for the adult child caregiver
- The Section 121 gain exclusion on a personal residence
- A detailed walkthrough of tax saving strategies in all scenarios
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
This episode is actually a replay of a previous episode we had done - Episode 63 - about the danger of picking individual stocks. This time we wanted to rename it "Betting the Farm" because we feel like that title is more representative of what we're seeing today in 2026.
In January of 2026, the S&P 500 had crossed the 7,000 mark and the Dow Jones had passed the 50,000 mark. These are both tremendous milestones in the United States stock market. Not to mention, countries other than the United States, which have struggled over the past decade plus, have significantly outperformed most companies in the United States over the past year or so, and history has shown us that this trend can continue for quite a long time.
Another reason I wanted to bring this episode back is because it's easy to look like you know what you're doing and feel good about picking stocks when the overall market is doing well. It isn't until you experience a significant drawdown that your thoughts, confidence, and emotions start to change.
And this isn't just about stocks either. This can be really any asset class. It could be owning real estate while it's going up substantially. It could be buying gold before it takes off like it has throughout 2025 and 2026 so far, or even cryptocurrency.
Simply as a product of human nature, investors are extremely overconfident in their abilities and they're not realistic with themselves. Many times, in practice, we often see portfolios full of risky positions that have very little to no rational rhyme or reason for owning – and the reasons are many.
Many times, investors get into these positions simply because it was recently going up in value and so they didn't want to miss out. Or someone they know, who, by the way, is not a professional investor, shared with them their recent experience in the position. It also happens by reading some article on the internet or watching some show on financial television that all seem to be in consensus that a particular company or investment should be a good investment moving forward.
Another common one we see in practice is that positions start to build substantially and become overly concentrated in a portfolio when investors are afraid of taxation. Everyone hates paying taxes, including myself, and when people purchase an investment and it appreciates substantially and now has embedded capital gains, if they were to sell some or all of it, oftentimes people do not want to pay the tax that comes with it.
That causes them to hold the position for far too long and add additional risk to the portfolio by being over concentrated in that position. While this is understandable, you cannot let the tax tail wag the dog. Would you rather pay preferred capital gains rates and rip the band aid off to diversify, or would you rather take the risk that your position falls 70 or 80% or worse, slowly drags on with little return over the next decade? People hate paying taxes but I'd say losing 70 to 80% is worse than paying 15 to 20% in tax.
It also commonly happens when you work for a company that offers employer stock awards, such as RSU's, stock options, or stock in the 401k plan. Because as you work, you just continue to accumulate this stock and, while it's going up, you feel like you should just continue accumulating it without a need to diversify at any point in time, since it seems like it's always going to make you money, and you have a natural bias towards the great company that you work for.
But the vast majority of the time, it's purely a hunch or a guess. You're purchasing an investment just hoping and thinking that it will succeed over the long run.
I want this episode to serve as a reminder about risk taking and diversification.
While times are good we feel good and we often lose sight of the ultimate goal for our investments and what we need them to do for our financial plan. Sometimes when things do extraordinarily well, we continue to ride the wave, thinking we'll make more and more money, and don't think about the potential ramifications of when the tide goes out. And I have a feeling that the next time the tide goes out, many people are going to be caught swimming naked and get burned in a lot of the positions we're seeing people accumulate today. Whether that's stocks particularly in companies in the US, large positions in AI-related stocks, your employer stock awards at work, cryptocurrencies, or even commodities like gold.
If you're one of those investors that has been riding the wave on a certain position and you feel like you've made a lot of money and that the trend could continue, you may want to rethink your overall goal and strategy and consider proper diversification. Especially if you are trying to grow a portfolio that you will need to live on throughout a potential 20 to 30-year retirement.
That being said, enjoy this week's replay of why picking stocks can be dangerous.
More specifically, we discuss:
- The most important question for DIY investors picking stocks and funds
- What does the research say about stock picking and market speculation?
- A surprisingly small percentage of stocks generate an overwhelming majority of shareholder wealth
- Investor emotions serve as a significant roadblock in making investment decisions Your Family Risk Profile
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
Key Moments:
(00:00) Introduction to Betting the Farm
(08:43) DIY Investing: Picking Individual Stocks
(10:43) Stock Pickers Typically Underperform Market. What Does The Research Say?
(16:41) Very Few Stocks Drive All of The Market's Growth Over Time
(23:34) Emotions Make Investing Extremely Difficult
(26:03) The #1 Question You Should Ask Yourself When Picking Stocks or Timing The Markets
If you're doing your own taxes or working with a tax preparer who doesn't specialize in wealth accumulation, financial planning and retirement, there's a good chance you're leaving thousands of dollars on the table every single year.
We're talking four and five-figure mistakes that happen because nobody's looking at the details.
In this episode, Cameron walks you through six of the most expensive tax blunders he sees wealth accumulators and retirees make - from losing track of IRA basis to triggering Medicare surcharges you didn't see coming.
These aren't theoretical problems. These are real mistakes costing real people real money.
Learn about these potential issues before they arise so you don't make the same mistakes!
More specifically, Cameron discusses:
- Losing Track of Form 8606 and Non-Deductible IRA Basis 2. Estimated Tax Payment Disasters 3. The IRMAA Time Bomb & Medicare Premium Surcharges 4. QCD Mistakes 5. Missing Cost Basis on Old Stock Positions & Paying More Taxes Than Necessary 6. State Tax Exempt Interest and Dividend Mistakes
Resources:
- Get Show Notes Here
- Retired-ish Newsletter Sign-Up
- See if you're a good fit for our Free Tax-Optimized Retirement Playbook™
Key moments:
(00:00) Tax Season Blunders to Learn From and Avoid
(05:33) 1. Losing Track of Form 8606 and Non-Deductible IRA Basis
(12:28) 2. Estimated Tax Payment Disasters
(18:10) 3. The IRMAA Time Bomb
(22:56) 4. QCD Mistakes
(28:16) 5. Missing Cost Basis on Old Stock Positions
(32:30) 6. State Tax Exempt Interest and Dividend Mistakes
If you think estate taxes are only a problem for billionaires and celebrities, I've got news for you:
A couple in their 50s with a combined few million in retirement accounts, a paid-off home, maybe a rental property, and 20 + years of compounding ahead of them? Their beneficiaries could easily be looking at a 40% + federal estate tax bill when they die.
However, there are legitimate, legal strategies to dramatically reduce or even eliminate these taxes. Some of them are as simple as how you spend your money today. Others involve sophisticated trust structures that can save your family hundreds of thousands, if not millions in taxes.
In this episode of Retired-ish, Cameron pulls back the curtain on estate tax reduction strategies that high-net-worth retirees utilize to preserve their wealth and pass it on efficiently.
More specifically, Cameron discusses:
- What are gift and estate taxes? And how much are they?
- Who is subject to gift and estate taxes?
- Should you try and avoid gift and estate taxes or capital gains taxes?
- Stocks and real estate in irrevocable trusts
- Power of Substitution to swap assets between irrevocable trusts and your estate
- Retirement accounts and estate taxes
- Other strategies to reduce gift and estate taxes
Resources:
- Get Show Notes Here
- Retired-ish Newsletter Sign-Up
- See if you're a good fit for our Free Tax-Optimized Retirement Playbook™
Chapters:
(00:00) Understanding Estate Taxes
(04:00) Who Needs Estate Planning?
(08:19) Gift & Estate Taxes vs. Capital Gains Taxes
(10:41) Irrevocable Trusts: Real Estate & Stocks
(17:00) Advanced Asset "Substitution" or "Swap" Strategy
(20:29) Retirement Accounts & Estate Tax
(25:00) The Smart Spending Strategy
(30:42) Sophisticated Estate Planning Tools to Reduce Estate Tax Exposure
If you're going through a divorce or thinking about one, I've got news for you: your divorce decree doesn't override federal tax law, no matter what it says.
That rental property buyout you negotiated. You could be getting screwed on the tax basis. And that division of your ex's 401(k)? There's a one-time penalty-free distribution opportunity that most people miss because nobody tells them about it.
In this episode, I'm covering the frequently asked tax questions I get from clients and prospective clients going through divorce—from filing status rules that actually matter, to rental property tax nightmares, to who gets to claim the student in college. Some of this is basic and applies to everyone, while some of it's rather nuanced, but all of it can cost you real money if you don't understand.
More specifically, Cameron discusses:
- How do I file my taxes in the year I get divorced?
- Is Alimony or Spousal Support taxed?
- Can I deduct legal fees paid during a divorce?
- What happens to a retirement account like a 401(k) or IRA in a divorce? Do those get taxed if transferred to my ex?
- What happens with Health Savings Accounts (HSAs) during divorce?
- After a divorce, who gets any capital losses we have that we have been carrying forward to offset our capital gains and income?
- What are the tax implications of buying out your ex's share in an investment property?
- Who gets to claim our student in college?
Key Moments:
(00:00) Introduction to Divorce Tax Questions
(02:47) Filing Status and Suspended Divorce
(07:27) Married, Filing Separate, or Head of Household?
(09:19) Alimony and Legal Fees
(11:34) Retirement Account Transfers
(15:10) Health Savings Accounts and Capital Losses
(17:36) Rental Property Buyouts & Basis
(24:24) Claiming Dependents and Tax Credits
Resources:
- Get Show Notes Here
- Retired-ish Newsletter Sign-Up
- See if you're a good fit for our Free Tax-Optimized Retirement Playbook™
If you're planning to retire in the next year or two and you have a 401(k) loan, this episode could save you thousands of dollars in taxes.
I've seen too many people walk into retirement with an outstanding loan balance and get blindsided by a massive tax bill they could have easily avoided with a little planning.
Then we're going to tackle one of the biggest myths in the retirement world - the idea that 401(k) loans are double taxed. Spoiler alert: they're not, and even very influential financial gurus get this wrong.
More specifically, Cameron discusses:
- The requirements for a tax-free loan from an employer plan such as a 401(k)
- The tax ramifications of a "Deemed Distribution"
- The tax ramifications of a "Qualified Plan Loan Offset" or QPLO
- Potential tax pitfalls when retiring with an outstanding plan loan balance
- Are 401(k) loans double taxed?
Key moments:
(00:00) 401(k) Loans and Retirement
(02:12) Requirements for Tax-Free 401(k) Loans
(06:33) "Deemed Distributions" Explained
(11:03) "Qualified Plan Loan Offsets" and Rollovers
(15:43) Retirement Tax Planning & ACA Subsidies
(19:28) Case Study: ACA Subsidies at Risk with Outstanding 401(k) Loan Balance
(27:01) Alternatives for 401(k) Loan Repayment
(30:20) Debunking the Double Taxation Myth of 401(k) Loans
(39:51) True Costs of 401(k) Loans
Resources:
- Get Show Notes Here
- Retired-ish Newsletter Sign-Up
- See if you're a good fit for our Free Tax-Optimized Retirement Playbook™
If you are turning 65 soon, you are closer to becoming eligible for potentially thousands of dollars in tax deductions and savings opportunities that many people never take advantage of.
And if you're helping with your elderly parent's finances, there's a good chance they're entitled to tax breaks they don't even know exist.
The tax code is full of opportunities specifically designed for retirees—but here's the problem: Social Security isn't going to call and tell you about them. The IRS certainly won't. And unfortunately, most tax preparers are so focused on compliance and filing deadlines that they miss most of these strategies entirely.
I'm about to walk you through the most valuable tax-saving opportunities available once you reach your retirement years — some you've probably never heard of, and some that could literally save you tens of thousands of dollars over your retirement.
More specifically, Cameron discusses:
- Changes in the Standard Deduction and the new Enhanced Senior Deduction for those over age 65
- Tax impacts when a spouse or parent passes away
- When and what medical expenses can be deductible
- Using suspended rental real estate losses from previous years to offset other taxable income
- Funding Roth IRAs from otherwise taxable money and inheritances
- How an elderly parent can become a dependent of yours for tax purposes and the potential tax advantages
- Tax strategies when receiving lump sum payouts from Social Security now that the WEP & GPO provisions have been eliminated
- Qualified Charitable Distributions from IRAs
Key Moments:
(03:11) Increased Standard Deductions & New Deduction for Seniors
(05:32) Tax Opportunities After Spouse or Parent Passing
(08:31) Deductible Medical Expenses
(15:59) Utilizing Rental Real Estate Losses
(19:54) Taxable Wealth to Tax-Free Wealth
(26:12) Claiming Elderly Parents as Dependents for Tax Purposes
(29:58) Taxation Options for Social Security Lump Sum Payments
(34:50) Qualified Charitable Distributions (QCDs)
(41:39) Conclusion and Disclaimer
Resources:
- Get Show Notes Here
- Retired-ish Newsletter Sign-Up
- Cameron's book for Divorcées and Widows: Finding Financial Clarity & Confidence When Starting Over
- See if you're a good fit for our Free Tax-Optimized Retirement Playbook™
Most women become widows at just 60 years old—right when they're finalizing retirement plans and making critical Social Security decisions.
And here's what nobody tells you: after the death of your spouse, your brain literally doesn't work the same way while you're grieving, yet people around you are pushing you to make life-altering financial decisions.
In this episode, Cameron gives you a timeline of what needs to happen soon, what can wait six months, and what absolutely should not be decided on within your first year. Because the decisions you make in the next 6 to 18 months will determine your financial security for the next 20-30 years—and many widows are making at least two or three major mistakes that cost them hundreds of thousands of dollars over their lifetime.
Whether you've recently lost your spouse, you're preparing for the inevitable, or you want to help someone who's going through this right now—this episode could be the difference between financial clarity and decades of financial struggle.
More specifically, Cameron discusses:
- How your decision-making changes after the loss of a spouse
- The importance of creating a written timeline of to-do's to help gain financial clarity in widowhood
- What actions to take shortly after entering widowhood
- What actions can wait 6 months or more after entering widowhood
- Considerations and financial implications when it comes time to make big financial decisions
- When to consider making changes to your investment strategy and financial plan
Resources:
- Get Show Notes Here
- Retired-ish Newsletter Sign-Up
- Cameron's book for Divorcées and Widows: Finding Financial Clarity & Confidence When Starting Over
- See if you're a good fit for our Free Tax-Optimized Retirement Playbook™
Key moments:
(00:00) Widowhood: A Financial Guide
(03:26) Grief and Financial Decisions
(06:18) Immediate Financial Organization
(07:22) Urgent Financial Actions
(09:39) Accessing Emergency Funds
(10:41) One-Month Financial Priorities
(12:09) Contacting Institutions & Asset Identification
(14:37) Six-Month Review and Updates
(16:17) Longer-Term Decisions: Housing
(19:21) Housing: Financial and Tax Implications
(21:02) Investment Strategy Overhauls
(22:45) Key Takeaways for Widows
Our firm is currently hard at work conducting our second semi-annual strategy meetings with clients, serving real people just like you, and doing important planning for their retirement for income, taxes, investing, estate planning, and making important decisions such as Medicare enrollment and Social Security claiming.
Therefore, we're bringing you another encore episode today in honor of Medicare Open Enrollment, which kicks off every year on October 15th and runs through December 7th.
During this time you can make certain changes to various types of additional Medicare coverage such as a Medicare Advantage plan or Prescription Drug plan (Part D).
Then, Cameron breaks down the different components of Medicare and additional coverage options in layman's terms.
More specifically, Cameron discusses:
- Medicare Open Enrollment
- What is Medicare, and what are the main components
- What does Medicare pay for?
- What types of additional coverage are available? What are the costs?
- The difference between Medicare Advantage Plans (Part C) and Medicare Supplement Plans (Medigap), and some of the pros and cons of each.
- What factors should you consider when making coverage decisions?
Resources:
- Get Show Notes Here
- Retired-ish Newsletter Sign-Up
- See if you're a good fit for our Free Tax-Optimized Retirement Playbook™
Key moments:
(00:00) Medicare Open Enrollment 2025
(05:16) Medicare Basics and Misconceptions
(07:45) Original Medicare (Parts A, B, and D)
(09:13) Medicare Advantage Plans (Part C)
(14:30) Costs of Medicare Advantage Plans
(17:03) Medicare Supplement Plans (Medigap)
(22:31) Costs and Benefits of Medigap Plans
(28:27) MA vs. Medigap: Key Comparisons
This is an encore episode of one of our favorites!
Retirement income planning is vital to the sustainability of your lifestyle in retirement, so don’t neglect it!
Plain and simple, your retirement income plan will make or break you in retirement. In this episode, we discuss the importance of creating an actual plan that focuses solely on how you will get your income in retirement, and the greatest risks your income will face.
An appropriately structured income plan is crucial so that you can avoid entering retirement being uncertain about how much you can spend each month, vulnerable to the big retirement risks, and unstructured with your nest egg – meaning that you really have no idea how to arrange your affairs, what accounts to have, what investments to select, and what accounts they should go in.
Your retirement income will drive your lifestyle, not necessarily the amount of money you have. The more confidence you have in your retirement income plan, the more likely you will live a happy and fulfilling lifestyle that allows you to focus on the more important things in life.
More specifically, I discuss:
- How to Determine of You Are a Constrained Investor
- The Dangers of “The 4% Rule”
- Retirement Timing Risk (Sequence of Returns Risk) Explained
- Inflation and Longevity Risk
- Advantages of Segmenting or Bucketing Your Nest Egg
- Our Free Tax-Optimized Retirement Playbook™
Resources:
Get Episode Resources Here Free Tax-Optimized Retirement Playbook™ Retired·ish Newsletter Sign-Up
This one free action could save you thousands in an identity theft or fraud situation - yet 90% of affluent Americans never do it.
In today's world of AI-powered scams and relentless fraudsters, protecting your identity isn't just optional, it's essential. Whether you're safeguarding substantial assets, retirement funds, or helping an elderly parent navigate their financial vulnerability, the threats are real and growing.
While some asset protection strategies require complex planning for those with intricate financial situations, there's one powerful tool that’s available to everyone: the credit freeze.
In this episode, we dive into how this simple step can become your first line of defense against identity theft and fraud.
More specifically, Cameron discusses:
- What is a credit freeze or security freeze?
- Who is a credit freeze a good strategy for?
- How do you freeze your credit?
- What happens if you need to apply for a loan or new credit when you have a credit freeze in place?
- How do you remove or lift a credit freeze?
- Can you help your elderly parents freeze their credit to better prevent fraud?
LISTENER Q & A:
Question: "I am about to start the process of creating a revocable living trust for my spouse and I. We own our home, but we also own three rental properties out of state, two located in the same state and one located in another state. From what I understand so far, this trust is going to be specific to the state in which I live. What are the implications here for my home and my other properties? Any tips you can provide on what to do so I can make sure I understand the situation better when I consult the attorney?"
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Access Show Notes Here
Key moments:
(03:17) Credit Freeze: How It Works (06:12) Implementing and Managing Credit Freezes (08:17) Lifting and Removing a Freeze and Other Tips (11:18) Credit Freezes for Elderly Parents (13:39) Listener Question: Funding a Revocable Living Trust with Real Estate (16:25) Multi-State Properties and Insurance When Dealing with Trusts (18:47) Estate Planning Guidance & Additional Resources
Attention retirement savers!
If you don't expect to accumulate tens of millions in your retirement account, you may want to stop contributing to a Roth. That’s right, I said tens of millions.
Roth accounts can be a fantastic wealth accumulation for some, and an expensive mistake for others.
In this episode, we discuss what many people, including many professionals often miss when it comes to deciding whether or not to contribute on a pre-tax basis, or after-tax basis to a Roth.
More specifically, Cameron discusses:
- The common errors people make when trying to determine whether or not to go Roth.
- 3 major factors that contribute to your future tax situation
- The impacts of taxation at marginal vs. effective tax rates
- An example case study of a high earning married couple
- A shocking reality for some making the case for Roth contributions
- An alternative example for our case study that reflects most people’s reality
Key moments:
(01:05) The Critical Math Most People Miss
(02:30) The Real Decision Factor: Your Personal Future Tax Situation
(04:12) Three Key Questions to Ask Yourself
(05:15) Understanding Marginal vs Effective Tax Rates
(06:28) High Earner Example: $500K Income Analysis
(08:36) The Shocking Reality: $40 Million Required to pay 32% in Fed Taxes
(09:55) Realistic Retirement Scenario: $240K Annual Spending
(12:25) The 32% Tax Rate Scenario Breakdown
(14:54) Why You Need a Financial Plan
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
If you’ve ever wondered why seasoned investors tell you to “stay the course,” it’s because history has taught us something simple but profound: time in the market beats timing the market.
But let’s rewind a bit. Investing isn’t just about stocks going up and down on a chart — it’s about preserving your purchasing power, compounding your money, and building resilience against life’s financial curveballs.
So today, I’m going to take you on a journey: from the magic of compound interest, to the harsh reality of inflation, to how the stock market has historically rewarded patience — even through wars, recessions, and crises.
More specifically, Cameron discusses:
- A powerful example of how compound interest and inflation will affect you over time
- Historical statistics of the U.S. stock market that will shock you
- Bull markets vs. Bear markets and what to expect
- The difference between volatility and risk when investing for your financial goals
- How to manage risk with asset allocation and diversification
- The overconcentration problem of the S&P 500 as it stands today
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Definitions:
The S&P 500 tracks the performance of 500 large-cap U.S. companies, serving as a benchmark for the U.S. stock market. The index is weighted by market capitalization. Compound Interest: Compound interest is the interest earned on both the original amount and the accumulated interest. Bear Markets are defined as periods when the S&P 500 experiences a price loss of 20% or more following a gain of 20% or more from its previous trough. Bull Markets are defined as periods when the S&P 500 experiences a price gain of 20% or more following a decline of 20% or more from its previous peak.
Key moments:
(03:24) Compound Interest and Inflation Explained (06:48) Rethink What You Think You Know About Investing (09:55) Historical U.S. Stock Market Performance (14:27) Understanding Market Cycles (17:49) Market Volatility vs. Investment Risk (21:11) Asset Allocation and Diversification (26:20) Key Takeaways
You’ve saved diligently in your IRA, built a comfortable retirement nest egg, and set up a family trust to avoid probate and streamline your estate.
And then—because it feels like the safe, responsible thing to do—you name your trust as the beneficiary of your IRA. But here's the problem...
In the post–SECURE Act world, naming a revocable living trust as the beneficiary of a Traditional IRA can unintentionally trigger a tax disaster for your heirs. Instead of a steady stream of income over a lifetime, they may be forced to drain the account—and pay taxes on the entire balance over just several years at the highest marginal tax brackets.
We’re talking about six- or even seven-figure IRAs being distributed in ways that not only defeat your estate planning goals but also crush your heirs with avoidable taxes.
This isn’t theoretical, it’s happening now. And with compressed trust tax brackets, a badly structured trust can push your retirement dollars into the 37% federal tax bracket, sometimes with just $16,000 of income.
More specifically, Cameron discusses:
- When should you consider naming your family living trust/revocable living trust as a beneficiary of your retirement account?
- What are the potential consequences of naming a trust as the beneficiary of your retirement account?
- How should my trust be structured in order to pass retirement assets to my beneficiaries in the most tax-efficient manner?
- What if my one of my trust beneficiaries is a charity?
- What if I name my trust as a beneficiary of my Roth IRA?
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Access Show Notes Here
- Schedule a Discovery Call for a Free Tax-Optimized Retirement Playbook
Key moments:
(04:41) When Naming a Trust as the Beneficiary of Your IRA Makes Sense
(10:22) Potential Issues with Trusts as Beneficiaries of a Retirement Account
(17:55) Why Trusts Fail to Qualify as a “See-Through” Trust
(21:52) Tax Implications of Trusts as Beneficiaries
(27:42) Charities as Beneficiaries of Your Retirement Accounts and Trusts
(31:44) Roth IRAs: A Potential Solution
Social Security can be a maze of rules and decisions to make if you’re widowed or divorced, which makes claiming a daunting task.
Most claiming decisions are permanent and can make a difference of tens if not hundreds of thousands of dollars over the rest of your lifetime, so you want to get it right.
In this episode, Cameron Valadez, CERTIFIED FINANCIAL PLANNER™ and Enrolled Agent shows you how to navigate these important decisions faced on your own.
More specifically, Cameron discusses:
- The current state of Social Security and why early filing may not be in your best interest
- What divorcées need to know about benefit eligibility, what they may be entitled to, and future changes in life circumstances
- Questions Cameron has received in the past from divorcées
- What widows need to know about survivor benefit eligibility, what they may be entitled to, and future changes in life circumstances
- Differences between widow and divorced widow benefit eligibility
- Coordinating survivor benefits with your own potential retirement benefits
- Questions Cameron has received in the past from widows
- Tax withholding implications on Social Security benefits
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Access Show Notes Here
- Schedule a 20-Minute Discovery Call & Get Your Copy of “Finding Financial Clarity & Confidence When Starting Over”: 10 Blind Spots You Should Know To Help Mitigate Financial Uncertainties In Your New Life
Key Moments:
(01:11) The Social Security Crossroads (02:09) Debunking the Bankruptcy Myth (08:19) Understanding Divorcee Benefits (12:04) The 10-Year Rule and Its Impact (17:03) Real Questions from Real Divorcees (22:06) Survivor Benefits: What You Need to Know (27:06) Strategic Options for Survivor Benefits (29:22) Understanding Survivor Benefits and Earnings Limits (32:20) Navigating Remarriage and Survivor Benefits (35:03) Full Retirement Age Confusion: Survivor vs. Retirement Benefits (36:00) Strategic Switching: Survivor to Retirement Benefits (37:20) Tax Considerations for Social Security Recipients (40:33) Final Thoughts and Key Takeaways
Can Artificial Intelligence really give you solid financial advice—or just a generic roadmap that ignores the potholes? In this episode of Retired·ish, we explore the growing trend of people turning to AI tools like ChatGPT for help with retirement planning, tax questions, and investment strategies.
Sure, AI can be fast, cheap, and eerily accurate… sometimes. But when life gets complicated—and it always does—there’s no substitute for personalized advice from someone who understands the human side of money. Join Cameron Valadez, CFP® and Enrolled Agent, as he breaks down where AI shines, where it falls flat, and when it’s time to stop asking the chatbot and consult a pro.
More specifically, I discuss:
- The use of AI chatbots for advice
- CFP® Board consumer survey on where Americans are getting financial advice
- Limitations and drawbacks of financial advice from AI chatbots vs professional advice from humans
- Generative AI vs Predictive AI
- AI financial scams and how to protect yourself
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key moments:
Here we go again, discussing hot takes on permanent life insurance and its use as an investment vehicle.
In this episode, I tackle one of the best questions I have received in a long time regarding the cash value and hidden costs associated with permanent life insurance that I think is critical to understand.
Before considering a permanent life insurance policy as an investment option, make sure you are utilizing the more transparent, low cost, and tax efficient investment vehicles on a regular basis.
More specifically, I discuss:
- The biggest hidden cost in many permanent life insurance policies
- Where your premiums go when funding permanent life insurance
- What is the cash value component of a permanent life insurance policy?
- How does the death benefit payout work in permanent life insurance policies?
- What can happen if you take a loan from your permanent life policy?
- Why permanent life insurance policies make for poor “investment vehicles”
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key Moments:
(02:05) The Controversial Question About Permanent Life Insurance Nobody is Asking
(05:18) The Answer
(06:23) Understanding Permanent Life Insurance Premiums
(10:33) Taking A Loan From Your Permanent Life Insurance Policy
With the growing US federal deficit, tariffs, fears of recession, and upcoming tax breaks, inflation is a top concern in the minds of many retirees and soon-to-be-retirees.
Investing in TIPS, or Treasury Inflation-Protected Securities, is one of the most commonly touted strategies that can help stave off unexpected inflation, however there are still important risks to understand.
Can TIPS really preserve your purchasing power in a meaningful way and kill off inflation no matter what happens in the markets or economy? Or are they just another government bond with a fancy name and a built-in marketing hook?
More specifically, I discuss:
- What are Treasury Inflation Protected Securities (TIPS)?
- How do TIPS work? How are they different from traditional (nominal) bonds?
- Important things to know when purchasing TIPS
- Individual TIPS vs. mutual funds and ETFs that invest in TIPS
- Potential risks of investing in TIPS
- Tax ramifications of TIPS
- Why would a pre-retiree or retiree consider adding TIPS to their portfolio?
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key moments:
(02:35) Understanding TIPS: The Basics
(08:55) Important Things to Know When Buying TIPS and/or TIPS Fund
(15:09) Some Risks With TIPS
(19:03) Tax Implications of TIPS
(23:32) Should You Consider Investing in TIPS?
The “One Big Beautiful Bill” recently passed through the House of Representatives by a narrow margin and is now in the Senate’s hands.
This bill consists of extremely important tax legislation that aims to continue on and add to the current tax provisions we have grown accustomed to for the last several years under the Tax Cuts and Jobs Act.
As a pre-retiree or retiree, many of the federal tax proposals in the current bill are highly relevant and could warrant adjustments to your retirement planning if passed.
In this episode, Cameron provides a breakdown of the most impactful changes and how they may affect you.
More specifically, I discuss:
- Proposed changes to current Tax Cuts & Jobs Act legislation
- State & local tax deduction (SALT) cap proposed changes
- Deduction updates for business owners and landlord (bonus depreciation, QBI)
- Current tax provisions to be repealed under the One Big Beautiful Bill
- Brand new provisions in the One Big Beautiful Bill relevant to pre-retirees and retirees
- Proposed changes to Health Savings Accounts (HSA)
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key moments:
(00:00) Introduction to the One Big Beautiful Bill (02:05) Key Provisions of the Proposed Bill (03:56) Proposed Changes to Current Tax Law (08:52) Proposed Changes to SALT Deduction (11:01) Proposed Changes in Small Business Owner Tax Breaks (14:10) Proposed Tax Provisions Set to be Repealed (15:43) Proposed Brand New Tax Provisions
Income planning will make or break your retirement years - This is because your income throughout retirement will be what controls your lifestyle, not your net worth.
When doing your pre-retirement planning - hopefully several years before your desired retirement - you’ll want to match your lifestyle wants, needs, and goals with the income you are able to generate from your various financial assets.
However, depending on where and how you plan to generate income from, you may run into problems along the way. Many times, we see issues arise with those who primarily focus on a dividend spending strategy from their investment portfolios to supplement their other retirement income sources.
More specifically, I discuss:
- Defining retirement income planning
- The 2 major pitfalls you need top watch out for when creating your retirement plan
- Investment returns or income?
- Potential cons of a “probability-based” retirement plan
- Wade Pfau’s Four L’s of Retirement
- Matching your various retirement income sources with your goals
- Potential issues when relying on only one income source such as real estate or dividends
- The importance of dividends
- A pure dividend spending strategy isn’t a great retirement income strategy
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key moments:
(02:02) The Error of Relying Solely on 1 Retirement Income Source (02:57) Challenges of Basic Income Planning
(04:58) Retirement Income is More Important Than Investment Returns (08:33) The Four L’s of Retirement Planning (11:15) Funding Your Desired Lifestyle
(12:30) Rental Real Estate May Not Be The Most Efficient Retirement Income Plan (14:53) Planning for Legacy, or Not (16:04) The Importance of Liquidity in Retirement (18:06) The “Live Off Of Dividends” Strategy Debate (24:44) The Risks of High-Dividend Paying Stocks (29:52) Total Return Investing as an Alternative
This is a must-listen episode that could save your family's financial future… Seriously. Estate planning is important, we know that, but what happens when things go wrong, very wrong?
In this episode, we delve into true stories of oversight and missed opportunities, each one a powerful lesson in what not to do.
Learn how simple mistakes today can cause chaos tomorrow and discover the steps you can take to avoid these pitfalls. Don't let your hard-earned legacy become a cautionary tale.
More specifically, I discuss:
- When multiple executors/trustees disagree
- Who has the power to make decisions when you’re gone?
- Corporate trustee failures tie up significant family wealth
- Digital recordkeeping in the 21st century put beneficiaries at a stand still
- Outdated estate plans can create tax time bombs
Resources:
- Retired-ish Newsletter Sign-Up
- Get a 2nd Opinion on Your Estate Planning Strategy
- Get Show Notes Here
Key moments:
(02:00) Sibling Disagreements and Executor Conflicts (08:22) Who Holds the Power After You’re Gone? Decision-Making in Trusts (13:04) Corporate Trustee Mishaps (20:25) Digital Recordkeeping Issues (24:32) Retirement Accounts and Trusts (29:57) The Expensive Dangers of Outdated Estate Planning Strategies
Long-term care insurance typically becomes a consideration for people in their 50s and 60s after they experience helping out with their aging parent’s care and realizing the substantial hit it can make on their life savings.
But one of the most overlooked aspects of long-term care insurance is the potential tax benefits that can be had. When considering long-term care insurance, understanding the potential tax benefits and how they pertain to your own financial situation can help you make a more informed decision.
More specifically, I discuss:
- How does the potential deduction for long-term care insurance work?
- What are the limitations when trying to deduct qualified long-term care insurance premiums?
- How might changes in tax law allow for or increase your long-term care premium deduction?
- What types of long-term care insurance are considered “qualified”?
- Can you deduct premiums paid for hybrid or asset based long-term care insurance?
- Can business owners get a deduction for long-term care insurance premiums paid?
- When can’t you deduct premiums paid for long-term care insurance?
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key moments:
(03:02) Are Long-Term Care Insurance Premiums Deductible? (05:33) Deducting Medical Expenses Above 7.5% Adjusted Gross Income (06:14) Long-Term Care Premium Deduction Limits By Age (10:53) Issues With Itemizing Deductions & The SALT Cap (13:24) What Constitutes a “Qualified” Long-Term Care Policy (15:31) Deducting Hybrid or Asset Based LTC vs. Traditional Long-Term Care Insurance (19:19) Deducting Long-Term Care Premiums for Business Owners (22:19) When Can’t You Deduct Your Long-Term Care Premiums?
Since President Trump took office for the second time in 2025, tariff talks are all the rage and markets have entered a new phase of extreme volatility.
Since tariffs can be a good and a bad thing, we think it’s necessary to have some additional context beyond what the mainstream media seems to be focused on specifically - which is higher prices and inflation.
To understand the potential economic impacts moving forward and how these tariffs might affect markets and your investment portfolio, we need to zoom out and take a look at more than just the current headlines.
More specifically, I discuss:
- What are tariffs in layman’s terms, and why do they exist?
- What are the potential impacts of tariffs?
- What has happened historically with tariffs in the U.S. and how did the stock market react?
- What happened to inflation and the stock market during President Trump’s first term and his “America First” trade policies?
- What can happen with inflation and volatility in the stock market when tariffs are increased?
- LISTENER QUESTION: Collecting Social Security Benefits while working and when benefit payments adjust for additional years of earnings.
Resources From The Episode:
- Retired-ish Newsletter Sign-up
- Get Show Notes Here
Key moments:
(02:01) What are tariffs and why do they exist?
(03:14) Potential impact of tariffs
(04:19) Historical facts about U.S. tariffs
(06:53) Potential impacts of tariffs on your investment portfolio
(07:36) What happened the last time President Trump’s Administration increased tariffs?
(14:42) Listener question: Collecting Social Security while working and benefit adjustments
Due to the increasing political and market uncertainty, and recent stock market correction, we felt it was more important than ever to reintroduce this episode of the Retired·ish Podcast throwing it back to episode #8!
In this episode we defined the downside of what is called Sequence of Returns Risk - which is in my opinion can be the greatest threat to your retirement savings and income.
This risk can present itself when markets happen to be volatile to the downside at nearly the same time that you enter retirement when you go from saving to spending your retirement nest-egg – which can be a very nerve-wracking experience to go through.
We explained why it is crucial to understand that saving for retirement is actually the easy part, and how spending what you’ve saved up in your investment portfolio can quickly become a risky endeavor, especially if you have no strategy to mitigate the downside of Sequence of Returns Risk.
More specifically, I discuss:
- What is the greatest threat to your retirement savings?
- Examples of sequence of returns risk in the savings phase of your life
- Examples of sequence of returns risk in the spending phase of your life
- The difference between monitoring account balances vs. average investment returns
- What types of strategies can you implement to try and reduce sequence of returns risk
Resources From The Episode:
- Retired-ish Newsletter Sign-Up
- Get Show Notes Here
Key moments:
(05:23) "Sequence of Returns Risk": Retirement's Hidden Threat (08:06) When The Sequence of Returns is Irrelevant (10:34) Impact of Return Sequence When Spending in Retirement (20:51) Emotion-Free Investment Strategy (23:09) Short-Term Retirement Fund Strategy (26:11) Investment Growth and Legacy Strategy
When the stock market produces double digit returns over multiple years in a row, investors and retirement savers naturally begin to get nervous and anticipate some sort of inevitable financial bubble.
This fear often stems from two things, from living and investing through recent historic market crashes such as the dot-com bubble and the great financial crisis, as well as the mere thought about how the recent and exuberant growth of your financial nest egg can sharply and suddenly be given back – and ultimately the thought of how that hit to your investments might impact your livelihood in retirement.
In this episode, we take a historical look at financial bubbles and what a “bubble” entails.
More specifically, we discuss:
- Insights from Howard Marks’ memo: “On Bubble Watch” and defining a financial “bubble”
- What causes financial or asset bubbles?
- How bubbles and market crashes can negatively affect investor behavior
- Media headlines and stock market bubbles
- Understanding the cycle of investment fads: My “Asset Bubble Circular Calculation”
- How an investment plan can guide you through market turmoil
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
- “On Bubble Watch” – Howard Marks https://www.oaktreecapital.com/insights/memo/on-bubble-watch
Key moments:
(03:36) Exploring Stock Market Bubbles and What They Really Are
(04:15) What Actually Causes Stock Market & Other Asset "Bubbles"
(09:55) Bubbles Can Cause Negative Changes To Your Investing Behaviors
(12:49) The Impact of Media Headlines
(15:17) "The Asset Bubble Circular Calculation"
If you’re a diligent retirement saver, you’ve likely heard of - and maybe even explored - executing a Roth conversion of some of your pre-tax retirement savings.
Executing the Roth conversion itself is the easy part, but trying to figure out whether or not it makes sense and will benefit your particular financial situation is the hard part - since you will voluntarily pay taxes when you convert and the conversion can’t be undone.
Rather than start converting to Roth on a whim, a thorough analysis should be done before making any decisions since a Roth conversion has risk and could end up being a very expensive mistake, but when done opportunistically, can save tens of thousands or more in taxes.
More specifically, we discuss:
- What has to happen for a Roth conversion to make sense?
- What is a Roth conversion and why do people and their professional advisors typically do them?
- What are the potential benefits that can come from a Roth conversion?
- Understanding Net Present Value (NPV) when determining whether or not a conversion makes sense
- When might a Roth conversion hurt you?
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
- Blog Article: Roth 5 Year Rule
- Previous Podcast Episode: What is a Roth Conversion and Should I Consider It?
- Decision Chart: Should I Consider Doing a Roth Conversion?
Key moments:
(05:01) What is a Roth Conversion?
(07:50) When Does It Make Sense to Consider a Roth Conversion?
(12:30) “Net Present Value” and Why It’s Important to Understand
(15:55) Recouping The Costs of a Roth Conversion Depends on Multiple Factors
(19:25) Roth Conversions with The Fastest Pay-Off
(20:25) When a Roth Conversion Might Hurt You
(25:40) Roth Conversions Carry Risks
Investing in the stock market by selecting a handful of individual stocks is tempting for many investors who dream of making substantial gains by picking the "next big thing." But despite the allure, there are many compelling reasons why investors should think twice before diving into individual stock picking and market speculation…
More specifically, we discuss:
- The most important question for DIY investors picking stocks and funds
- What does the research say about stock picking and market speculation?
- A surprisingly small percentage of stocks generate an overwhelming majority of shareholder wealth
- Investor emotions serve as a significant roadblock in making investment decisions
-
Your Family Risk Profile
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Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Ask Cameron A Question!
Key Moments:
(02:15) DIY Investing: Picking Individual Stocks
(04:15) Stock Pickers Typically Underperform Market. What Does The Research Say?
(10:12) Very Few Stocks Drive All of The Market’s Growth Over Time
(17:04) Emotions Make Investing Extremely Difficult
(19:33) The #1 Question You Should Ask Yourself When Picking Stocks or Timing The Markets
Retirement is often imagined as a permanent vacation that’s been earned over many years of sacrifice. You envision yourself traveling the world on cruises, playing endless rounds of golf or pickleball, or telling yourself that you will finally spend more of your time with family and start exercising more.
While these dreams can certainly be part of your retirement, it’s essential to understand that this is just one side of the coin.
More specifically, we discuss:
- How retirement has changed over the past few decades
- What it means to be Retired·ish
- Your dream retirement vs. the realities of day-to-day life in retirement
- Emotional aspects of retirement and sense of self-worth
- Changes to your social network in retirement
- The importance of financial and retirement planning before retiring.
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
Key moments:
(00:00) Redefining Retirement: A Lifestyle Choice (06:17) Plan Retirement Activities Early (10:00) Reconnecting with Social Circles in Retirement (11:14) Dynamic Retirement and Financial Planning Essentials
Two of the most prominent provisions – the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) - that can substantially reduce Social Security benefits for some federal, many public sector and civil service employees were just eliminated after being in effect for the last 40 years!
Teacher, police officers, firemen, and some federal workers are some of the most common groups affected by these provisions, and as of December 31st, 2023, they may see a bump in benefits or expected benefits they’re eligible to receive.
More specifically, we discuss:
- President Biden passes the Social Security Fairness Act on January 5th, 2025
- What are the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) and how do they work?
- How were some public sector and federal employees and retirees affected by these Social Security provisions?
- What are the potential benefits now that these provisions have gone away?
- Retroactive 2024 lump-sum payments
- Tax implications now that the WEP and GPO have been eliminated
- What you need to do to receive potential additional Social Security benefits
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
Key moments:
(00:00) WEP & GPO provisions reduce Social Security benefits for public servants.
(07:00) How do the WEP and GPO provisions work?
(08:51) GPO reduces public pension spouse's Social Security w/ examples.
(13:25) How might your benefits change moving forward in 2025 and beyond?
(14:19) Lump sum back-pay of Social Security benefits for 2024.
(14:55) Tax implications of lump sum payments and increased benefits.
There’s no question about it, that when it comes to saving for retirement, the financial mass media pounds the table with all things retirement accounts like IRAs and 401(k)s, but there’s a vastly underutilized investment vehicle that can help retirees enjoy a potential 6-figure retirement income, entirely tax-free.
We are referring to the good olé brokerage account.
A brokerage account is simply an investment account you open where you deposit money from your own bank account and then you can use that cash to invest in various investments held inside that brokerage account. Most commonly, people will invest in things like stocks, bonds, mutual funds, ETFs, things of that nature. In this episode, I teach you how you might utilize a brokerage account for a 6-figure retirement income, tax-free.
More specifically, we discuss:
- The difference between a brokerage account and a retirement account such as an IRA or 401(k)
- How a pre-retiree might accumulate funds inside of a brokerage account
- How taxes work when it comes to brokerage accounts and the investments held inside them
- How exactly you can end up paying no federal taxes on over 6-figures of income
- Hypothetical scenarios (basic concept and real-world)
- The importance of a retirement income plan and investment strategy
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
Key moments:
(03:44) Build brokerage account for retirement income flexibility (07:35) Pre-Tax IRA/401(k) assets taxed as ordinary income, brokerage assets can be subject to lower long-term capital gains rates (10:08) 0% capital gains tax up to $96,700 for married filing joint in 2025 (12:07) Conceptual Scenario: high 6-figure income in retirement, zero taxes (15:24) Real-World Scenario: high 6-figure income in retirement, zero taxes (23:02) Key points when using brokerage accounts as part of your retirement income strategy
Building up a substantial amount of savings in your 401(k) or IRA may serve as an indicator for a job well done in saving for retirement. But what soon-to-be retirees need to realize is that if the majority of your retirement savings is in pre-tax dollars, taxes will eventually be owed while in retirement and taking distributions.
Depending on your tax situation in retirement and the tax laws in place at that time, these large account balances may cause a tornado of taxation that you weren’t expecting - which can cause you to have to rethink your retirement strategy altogether.
In this episode, Cameron discusses why pre-retirees should reconsider building up their pre-tax retirement account balances, and what to do instead.
More specifically, we discuss:
- The potential tax problem Cameron has seen recently when talking with those age 50+
- The “shadow taxes” that await you in retirement
- The potential tax ramifications of building up large pre-tax IRA and 401(k) balances
- Alternatives to saving money on a pre-tax basis
- Why tax rates are likely to be higher in the future
- Roth conversions
- How to mitigate or avoid estimated tax penalties when implementing Roth conversions
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
A Roth IRA offers tax deferral on any earnings in the account. Qualified withdrawals of earnings from the account are tax-free. Withdrawals of earnings prior to age 59 ½ or prior to the account being opened for 5 years, whichever is later, may result in a 10% IRS penalty tax. Limitations and restrictions may apply.
(01:58) Those age 50 and over should slow down building up pre-tax 401(k) and IRA.
(06:01) Roth 401(k) employer match/profit sharing is taxable; 401(k) plan document dependent.
(07:48) Tax deduction today, or in retirement? Time Value of Money concept isn’t always what it seems.
(10:13) Consider choosing Roth IRA/401K over traditional savings moving forward.
(15:09) Optimize tax strategies with underutilized brackets.
(16:22) Potential tax changes could affect inheritance complexities.
(18:27) How to pay for taxes due from a Roth conversion and avoid underpayment penalties.
The landscape of taxes, retirement savings and Medicare are ever changing. Every year we see changes to the laws and limitations such as tax rates, brackets, and deductions, limitations on retirement plan contributions, and premium changes to Medicare to name a few.
2025 brings us some run of the mill changes sprinkled with substantial changes that can largely benefit retirees and soon to be retirees.
In this episode, we discuss some of the most important changes and how they may affect you.
More specifically, I discuss:
- Important adjustments to common tax deductions and tax rates
- Changes in the gift and estate tax landscape
- New retirement savings laws and updates for those still working in 2025
- Important changes for Medicare and prescription drug plans
- Social Security related updates for 2025
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Ask Cameron A Question!
Key moments are:
(00:00) 2025 standard deduction amounts increased for inflation. (05:32) Estate tax exemption may significantly decrease post-2025. (09:40) Those ages 60-63 can now put more into their employer sponsored retirement plan in 2025 (12:29) Employers can now contribute Roth, impacting taxes. (17:41) High out-of-pocket costs for Medicare prescriptions. (20:07) Out-of-pocket drug costs capped at $2,000. (22:59) 2.5% COLA for Social Security in 2025. Wage limit increases 4.5%.
If you’ve built or inherited an investment portfolio alongside the savings in your retirement accounts, you are likely to face some taxation every year on things like interest, dividends, and capital gains generated from the investments.
These might be investments such as stocks, bonds, mutual funds, or ETFs held in a brokerage account to name a few. While these investments can serve as a fantastic compliment to your other retirement savings, you’ll want to be sure to manage this money in the most tax-efficient manner each year to allow your money to last as long as possible.
In this episode we discuss 6 year-end strategies to help you reduce the annual tax bill from your portfolio.
More specifically, I discuss:
- 7 basic tax rules you need to know when it comes to non-retirement investment portfolios
- Properly offsetting gains and losses
- Properly use long-term losses
- Avoiding the wash-sale rule
- Make use of lower tax brackets
- Donating appreciated stock to charity
- Do not donate depreciated stock to charity
Resources:
- Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
- Ask Cameron A Question!
Key moments:
00:00 Non-retirement accounts have annual tax implications
05:29 Capital gains can be taxed between 0% to 40.8% based on income and nature of gain
09:02 Properly offset short and long-term gains with losses to defer taxes and optimize savings
10:22 Consider strategic tax planning for mutual funds held in non-retirement accounts
15:04 Transfer appreciated stock to family in lower tax brackets
17:22 Donate appreciated stocks if itemizing deductions and charitably inclined
In a recent study published by the investment research company Morningstar, they estimate that the average dollar invested in funds by individual investors over the 10 years ending December 31st, 2023 earned a 1.1% lower rate of return per year than the actual investments they were invested in.
This resulted in individual investors out on nearly 16% of the investment’s actual returns each year, even without consideration of any investment fees.
Morningstar updates this data annually as part of their “Mind The Gap” study, and in this episode I break down why this is happening and what this means for investors.
More specifically, I discuss:
- What investing insights does this research show us?
- The difference in investor return “gaps” per asset classes invested in.
- Investors miss out on 50% of taxable bond fund returns!
- Why are many individual investors earning lower average rates of return than their investments themselves?
- The difference in investor return “gaps” based on the volatility of a particular asset class.
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Ask Cameron A Question!
Key moments are:
00:00 Difference between investment and investor returns.
05:07 Investor behaviors remain consistent over the years despite political and economic uncertainty.
06:37 Return gap varies widely depending on asset class.
12:55 Investors tend to receive about 50% of bond fund returns.
16:33 The more volatile the fund, the more likely investor’s poorly time investment activity.
Kamala Harris and Donald Trump present starkly different tax proposals for the 2024 election reflecting their contrasting economic priorities. And while the exact outcomes of future tax policy are unknowable, you can be better prepared by having a good understanding of the potential changes.
In this episode, I address some of the major tax policies at play if either candidate takes office, and how they might affect your situation.
More specifically, I discuss:
- A basic review of the current tax laws in place under the Tax Cuts and Jobs Act (TCJA)
- What will happen if the TCJA sunsets (expires) in 2026 without intervention from either candidate?
- How might you be affected by the sunsetting of the TCJA.
- Brief overview of Harris’s main tax proposals and what it means for you.
- Brief overview of Trump’s main tax proposals and what it means for you.
- Will the State and Local Tax deduction (SALT) limits be removed before 2026?
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
00:00 Political uncertainty surrounds future tax provision changes
04:15 Middle-class tax burden increasing significantly by 2026
08:01 Harris aims to raise taxes on the wealthy, but Trump’s cuts may be too expensive
11:12 Higher corporate taxes could mean higher prices
16:39 $10,000 SALT cap limits state tax deductions significantly
21:05 Existing small businesses may face tax increases in 2026
24:50 Tax proposals may influence voters significantly come November 2024
In today’s challenging and expensive economic environment, many young adults in their 20’s and 30’s are struggling to find stable footing when it comes to their finances.
Whether that’s struggling to find that perfect career that can help them pay off their student debt, saving enough for a downpayment on a first home, or having extra cash each month to pay for childcare.
These common issues are causing many parents in retirement to rethink their own situation by contemplating whether or not they should step in to help, and if so, how?
More specifically, I discuss:
- How to go about making the decision to help your children out financially from your own retirement resources
- Gifting and seeing your kids benefit from financial help while you’re alive, or let them inherit your wealth at death
- Potential financial and tax ramifications of gifting your children money or assets vs. inheriting
- Important things to consider before making the decision to help your children out financially
- Real-life case study of a retired couple with 4 children
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
Key moments are:
02:37 Case Study of retired couple wanting to help children financially
04:55 Capital gains implications and cost basis
07:45 Child daycare for grandchildren, downpayment for a bigger home
10:50 What to consider when deciding whether or not to gift children money
15:01 Consider family dynamics, fair inheritance, and taxes
18:50 Assessing your children’s “wants” vs. their actual “needs” and strategies to preserve wealth
When approaching a retirement from a long and successful career, you’ll likely have a list of big decisions to make in a relatively short time.
One of those decisions will be whether or not you should manage your retirement account(s) on your own after retiring - when you begin to convert them into an income stream to support your lifestyle. This is opposed to looking for outside help from a professional such as a financial advisor or planner, and it’s a decision that comes with both pros and cons.
However, before you decide, I think it’s important to understand what you may be getting yourself into since spending and distributing your retirement savings is much different than saving for retirement.
More specifically, I discuss:
- What does it mean to manage your own retirement savings?
- What common tasks and expertise does managing your own retirement account(s) entail?
- What are some of the pros and cons to the “do it yourself (DIY)” approach to investing?
- Common examples of costly retirement mistakes, even when it feels like you’re making money
- Should you take on the responsibilities of investment management and retirement planning or seek help?
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Start Your Complimentary “Jump-Start” Retirement Analysis Here
- Ask Cameron A Question!
Chapters:
00:00 Managing your own retirement accounts: what's involved.
05:21 DIY investing can save direct costs but may have larger indirect costs.
09:55 Having accountability from a 3rd party may yield better outcomes.
13:57 Market drops can cause panic, lifestyle, and strategy concerns.
16:24 Have a plan to mitigate potential retirement risks and changes throughout life.
20:45 Examples of costly investment mistakes that feel like wins.
27:09 Managing your investments in retirement is not what you expect it to be.
When you have assets such as rental property that are going to need to provide you with cash flow throughout your retirement years, you’ll want to look into some level of asset protection at some point.
When it comes to rental real estate, the Limited Liability Company or LLC might be worth considering. However, the methods and strategies you use will depend on what you have at risk and certain risks that you might be creating yourself.
More specifically, I discuss:
- Setting up an LLC prematurely
- What is asset protection?
- Determining what assets to protect and how with examples
- Basic asset protection techniques
- What is a Limited Liability Company (LLC)?
- Benefits when used for rental property
- What does an LLC not do?
- How is an LLC commonly used for rental property?
- How can an LLC provide asset protection? - “Inside” & “Outside” liability
- When might you consider putting rental property in an LLC?
- Having your Revocable Living Trust own an LLC used for rental property
- Asset protection techniques to explore before creating an LLC
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
Key moments are:
00:00 Asset protection, LLCs, benefits, drawbacks.
04:00 You may not need an LLC for your rental property
05:38 There are no silver bullet asset protection strategies, even LLCs
07:37 Potential benefits of an LLC for rental properties
09:25 Tax return ramifications with an LLC
10:45 Potential drawbacks of an LLC and what they don't do for you as a landlord
13:46 How can an LLC actually give you asset protection (inside and outside liability)
19:17 When might you consider putting your rental property in an LLC?
22:29 Series LLCs
23:30 Consider having your Revocable Living Trust own your LLC
Having too much of your net worth tied up in one or a couple individual stocks can be a dangerous game to play. It’s one that relies heavily on luck and can present a significant risk to your life savings.
Things can either turn out really well, or very poorly. Sadly, many people often let their emotions and the potential tax ramifications dictate their next move, but should they?
In this episode, we discuss the risk of relying on one or two companies’ success to dictate your financial future, and how you can begin to mitigate that risk while saving taxes.
More specifically, I discuss:
- Why are large, concentrated stock positions a potential problem?
- What types of investors might have highly concentrated stock positions?
- What if the majority of my compensation is via employer stock?
- The dangers of relying on one company and overconfidence
- How to diversify your concentrated stock position
- Examples of methods you can use to divest of shares
- Tax efficient example of reducing concentrated stock positions, diversifying, and saving taxes
- A little-known strategy to consider if you have appreciated company stock positions inside your 401(k)
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
Key moments:
00:00 Diversify investments to minimize risk and avoid emotional biases
05:34 Active management and stock picking often fails to outperform benchmarks.
07:59 Timing markets is risky; consider long-term goals.
10:31 Diversification benefits
16:44 Expect intra-year stock market declines
18:54 Strategy for controlling taxes and staying diversified in the market with concentrated stock position
Implementing important estate planning documents is critical to leaving your ideal legacy upon your death.
Among the critical estate planning documents are wills and trusts. Often times, many people confuse the differences between the two, the benefits they can provide, and whether or not they need them at all!
More specifically, I discuss:
- Why getting the appropriate estate planning documents in place is so important
- What is a Will? What can it do?
- What is a Trust? What can it do?
- What is the difference between a Revocable Living Trust and an Irrevocable Trust?
- Common uses for Revocable Living Trusts
- Common uses for Irrevocable Trusts
- What Revocable Living Trusts and Irrevocable Trusts don’t do
- How the titling of assets can work in your estate plan
- The importance of naming beneficiaries
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
Key moments are:
00:00 Estate planning: wills, trusts, assets, and advice. 05:09 What does a will do? 08:26 Title of property and beneficiary designations. 10:24 What can a trust do? 14:16 Revocable trusts does not offer tax benefits. 20:20 Irrevocable trusts can have significant tax implications, good or bad. 22:18 The importance of naming beneficiaries and titling assets appropriately. 26:35 Estate planning can save your family money.
Retirees and pre-retirees often struggle when it comes to spending down their nest-egg in retirement because of the fear of the unknown. No one wants to run out of money too early, yet most people would also like to enjoy what they’ve worked so hard for. So how do you find that balance? How can you know what you can spend, and for how long? Living off of your wealth is entirely different than building your wealth. Without a retirement spending strategy, most people are going to either end up really worried about running out too early throughout their retirement, but end up leaving a pile of money on the table when they die, or running out of money too early in retirement – which for some, can be scarier than death itself
More specifically, I discuss:
- Why are retirement withdrawal strategies important?
- The main types of retirement withdrawal strategies
- Systematic Withdrawal Plan/Constant Dollar
- Time-Based Segmentation or “Buckets”
- Floor and Upside
- Dynamic Spending Strategy
- Variations and examples of real-world withdrawal strategies
- Strengths and weaknesses of the different retirement income strategies
- LISTENER QUESTION: Excess IRA/Roth IRA Contributions
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
Key moments:
00:00 Decades of work for retirement, learning to spend. 05:09 Customized retirement planning requires personalized, flexible strategies. 07:15 Customize retirement income strategy to meet financial goals. 13:57 Constant Dollar Strategy / 4% rule 16:36 Time Segmenting and Bucket Strategy 22:28 Floor and Upside Strategy 27:20 Dynamic Withdrawal Strategy 34:47 Listener Question: Excess IRA/Roth IRA Contributions
Life insurance has become an increasingly controversial topic in recent years due to the opinions of financial gurus on YouTube, insurance salesmen, and media giants especially when it comes to using it as a vehicle to build wealth.
When considering life insurance as a wealth building vehicle, it really comes down to who is using it and how they are using it. Ultimately, when it comes to building wealth, permanent life insurance is a potential option, but only in very unique circumstances.
More specifically, I discuss:
- The two main types of life insurance
- The main types of permanent life insurance
- The structure of permanent life insurance
- The different variations of universal life insurance
- Benefits and downsides to permanent life insurance
- How permanent life insurance can be used to build wealth
- How to structure permanent life insurance policies for wealth building purposes
- Who should consider using life insurance to build wealth, and who shouldn’t
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
Key moments:
00:00 Understanding when life insurance can build wealth.
05:58 Permanent insurance costs more than term insurance.
10:05 Universal life insurance allows tax-free loans.
13:35 Insurance policies allow redepositing, not like retirement.
14:58 Limited control over investments, potential for higher returns.
21:17 Evaluate costs and fit for wealth building.
23:11 Future episode will cover life insurance info.
Investing in real estate historically has been a tried-and-true method of building wealth over the long-run, if you have the right wherewithal and mentality to do it – Let’s face it, it takes work.
However, as with any type of investment, investing in real estate has its own set of risks.
Without proper analysis, you can lose a lot of money even if you accept what looked like a great deal. Or, you might be generating minimal cash flow that could have been a lot more cash flow if you were better prepared when analyzing your real estate deals.
In this episode, we show you how to analyze a real estate deal and compare it with other investment opportunities.
More specifically, I discuss:
- Real estate is a numbers game
- Some of the risks involved with real estate investing
- The “4 Return Components of Rental Real Estate”
- The potential tax benefits of investing in real estate
- Analyzing a real estate deal
- Using your analysis to help you make decisions
Resources:
Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis Ask Cameron A Question!
Key moments are:
00:00 Real estate investing has inherent uncontrollable risks
04:07 Critical components of real estate investment analysis
07:25 Hypothetical 20% return on property investment
11:26 Consult a tax advisor for potential write-offs
14:17 Avoid negative cash flow with proper monitoring
18:27 Using analysis for hypothetical $650,000 inherited property
21:36 Low rate of return, mortgage doesn't matter
23:14 Conservative 4% annual appreciation yields $26,000
27:26 LPL Financial offers advisory services, consult professional
28:57 Municipal bonds tax free, consult advisor, no guarantees
2024 is an election year, and not just any election year, but what could be one of the most controversial election years in our Nation’s history.
Given the constant influx of media hype around everything such as: geopolitical tension, political dispersion within the US, inequality, inflation, government spending and the nation’s screaming debt levels, the collapse of the US dollar, student debt, the uncertainty of Social Security, all while the stock market has continued to new make new highs - Investors and everyday people saving for retirement are left to wonder, what’s going to happen to my investments?
More specifically, I discuss:
- Does the US president influence US stock market returns in an election year?
- Have markets fared better during election years with a Republican or Democratic President?
- Does the political make up of Congress influence market returns in an election year?
- What should I do with my investment strategy during an election year?
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis Ask Cameron A Question!
Key moments are:
00:00 Presidents have limited impact on the economy.
03:48 Economy and stock market are driven by many factors.
09:59 Investing not tied to political party affiliations.
12:16 Worrying about market uncertainty can be counterproductive.
14:54 Invest carefully for long-term success in companies.
18:11 Investment strategy should match long-term goals.
Whether you’re self-employed or an employee, a Health Savings Account or HSA can provide you with a triple tax benefit! Therefore, if you’re serious about saving taxes and building wealth, it’s critical to understand the benefits and rules of the Health Savings Account.
If an HSA makes sense for your situation, you can benefit by receiving tax deductions based on money contributed into the account, tax-deferred growth on any interest or gains earned on the investments inside the account, and potentially tax-free distributions from the account that you take for medical expenses.
The HSA is the only tax-advantaged account that has the ability to give you both a tax deduction for the money you put in, and tax-free withdrawals on the way out. Even better than the Roth IRA!
You can also invest the money inside an HSA in a wide variety of investments! In some people’s opinion, it is seen as the ultimate retirement savings vehicle, so don’t let the name fool you!
More specifically, I discuss:
- What is a Health Savings Account (HSA)?
- The triple tax benefits of an HSA
- The rules and eligibility requirements when utilizing an HSA
- Who should consider an HSA?
- The “13-month” or “last month” rule when contributing to an HSA
- The 3 methods of using an HSA
- Other unique strategies and other opportunities unique to HSAs
- BONUS: HSA strategy for adult children under age 26 with high earnings such as professional and college athletes, entertainers, business owners, and young professionals
- LISTENER QUESTION: HSA contributions and Medicare!
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
Key moments:
00:00 HSA for healthcare savings provides a triple-tax advantage.
03:38 HSA offers triple tax benefits for saving.
09:02 Eligibility for HSA: high deductible health plan.
11:04 Consider plan's deductible, out-of-pocket expenses. HSA criteria.
16:41 HSA contributions and potential penalties explained.
18:08 At 65, take money out - no penalty.
23:00 Be careful of double dipping with taxes.
28:42 Maximize HSA contributions for long-term tax benefits.
30:20 Listener Question from Diane
Are you tired of handing over too much of your money to the tax authorities every year? Or wondering if there’s a better way to go about managing your cash flow when it comes to paying your taxes?
If so, it's time to take control of your finances and maximize your wealth building machine. In this episode, I will show you how to adjust your tax withholding to keep more money in your pocket throughout the year so you can create a plan to make more of your money work for you, and not the IRS.
More specifically, I discuss:
- Understanding tax withholding
- Why adjusting tax withholding is important
- Major factors to consider when adjusting tax withholding
- How to determine the appropriate tax withholding or estimated payment amounts
- Steps to adjust tax withholding or making estimated payments
- Exemption from tax withholding
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
The key moments in this episode are:
00:00:00 - Tax Withholding Challenges
00:03:17 - Importance of Adjusting Tax Withholdings
00:06:11 - Avoiding Underpaying Taxes
00:11:56 - Factors to Consider When Adjusting Withholdings
00:15:36 - Understanding Withholdings and Tax Advice
00:16:13 - Tax Implications of Inheritance and Investments
00:17:32 - Tax Considerations for Starting a Business
00:18:57 - Navigating IRS Withholding Calculator
00:25:32 - Options for Adjusting Tax Withholdings
00:31:51 - Qualifying for Tax Exemption
00:32:26 - IRS Lock-In Letter
00:33:04 - Updating Form w Four
00:34:11 - Maximizing Financial Growth
If you are nearing retirement and have your eyes set on that dream day on the horizon (or even if you have recently entered into retirement) you need to know that you’re more responsible now - than ever in our nation’s history - for figuring out how to save, invest, and convert the financial resources you’ve spent your entire life accumulating into spending power that will last you a two to three decade retirement.
You are responsible for doing the necessary planning ahead of time in order to fund your ideal lifestyle in retirement.
More specifically, I discuss:
- How your retirement income will drive your ideal lifestyle
- The importance of after-tax retirement income
- The timing of your retirement income and how it can affect your lifestyle
- The risks that can threaten your lifestyle in retirement
- The role of personal preferences when doing your retirement income planning
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
The key moments in this episode are: 00:02:01 - Retirement Income Efficiency 00:04:48 - Risks and Obstacles in Retirement 00:09:03 - Real Estate Investment Case Study 00:13:21 - Personal Preferences and Retirement Goals 00:15:45 - Understanding Retirement Income Streams 00:16:26 - Listener Questions and Newsletter 00:17:11 - Sharing the Show and Learning Opportunities
It seems that each and every year when our firm reviews tax returns in consultations and second opinions we find dozens of missed tax savings opportunities: whether it be missed deductions, forgone strategies, less than ideal business entity or real estate structures, or simply improperly reported figures.
This holds true whether you do your taxes yourself with an online software or use a professional. Sometimes these missed opportunities are due to honest mistakes, other times it is due to tax documents with improper figures such as 1099s from investment firms, but more often than not it is due to the complex tax code and the lack of awareness of the potential strategies available to you and how to properly implement or report them when filing.
Every year we are reminded of the importance of reviewing tax returns to make sure that these savings opportunities aren’t continuously missed in future years, and you pay more in taxes than necessary or have to pay penalties that could have been avoided.
In this episode, we review some of the areas of your tax returns you should pay more attention to, and some of the potential strategies to be on the lookout for.
More specifically, I discuss:
- The first steps to take before beginning your tax preparation
- What to look out for when receiving tax documents such as W-2s and 1099s
- Common pitfalls and errors to watch out for when gathering information and inputting it into your individual tax returns
- Commonly missed deduction opportunities for business owners
- Potential carryover losses for beneficiaries of a trust or estate
- What to do with your newfound tax savings
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
The key moments in this episode are: 00:00:00 - Missed Tax Savings Opportunities
00:01:29 - Importance of Reviewing Your Tax Return
00:03:05 - Checking Tax Documents
00:08:25 - Providing Accurate Information
00:11:52 - Tax Considerations for Investments
00:16:08 - Understanding Tax Loss Carryovers
00:17:06 - Taking Advantage of Market Decline
00:18:38 - Managing Tax Savings
00:19:35 - Seeking Second Opinion and Getting Retirement Planning Resources
00:20:56 - Investment Risks and Tax Considerations
Over the past few years one of the hottest topics has been the rise of inflation throughout the economy. Inflation impacts our day-to-day financial lives in numerous ways, good and bad, and has a significant effect on our investments over time. It is a silent killer that affects our spending habits, retirement income and other financial goals you we have.
Understanding how inflation works over the long-term and how it can affect your investment decisions is a critical piece to your financial and retirement plans. Social Security has two unique provisions for those who will receive pensions from government related entities known as the Windfall Elimination Provision (WEP) and the Government Pension Offset (GPO). If you are to receive a pension from a government related entity, these are two must know provisions to help you make Social Security claiming decisions.
More specifically, I discuss:
- The misconceptions around inflation
- How inflation affects your investments and planning
- Predicting the movements of the economy and interest rates
- Listener question regarding Social Security WEP and GPO provisions
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
The key moments in this episode are: 00:00:00 - Understanding the Impact of Inflation
00:04:19 - Long-Term Impact of Inflation
00:07:42 - Addressing Inflation and Taxes in Financial Planning
00:11:09 - The Risk of Predicting Inflation and Interest Rates
00:14:30 - Understanding Social Security Provisions
00:17:41 - Understanding the Windfall Elimination Provision (WEP)
00:18:56 - Impact of WEP on Spouse's Social Security Benefits
00:20:25 - Complexities of WEP Calculation
00:21:55 - Government Pension Offset (GPO) and Its Impact
00:24:14 - Seeking Comprehensive Retirement Planning
Although you may be familiar with some of the basics of Traditional IRA and Roth IRA retirement accounts, there are many different rules and tricky nuances that you might not know that can open the door for more wealth building opportunities, or possibly be a cause for concern.
For instance, you may think you make too much money to contribute to a Roth IRA or that you can’t because you have a 401(k) plan at work when that may not be true. Or maybe you’re contributing to one of these types of accounts and taking tax deductions when you’re not actually allowed to. Or you may be reporting contributions and withdrawals incorrectly on your tax returns.
All of these issues are crucial to understand each year when using Traditional IRA and Roth IRA retirement accounts to accumulate wealth.
More specifically, I discuss:
- Summary of the differences between a Traditional IRA and a Roth IRA
- The rules surrounding contributions to a Traditional IRA and Roth IRA including:
- How to fund them
- Annual contribution limits
- Eligibility to make contributions
- Contribution deadlines
- Defining “Earned Income” for contribution eligibility
- Contribution limitations to Roth IRAs
- Deductibility of Traditional IRA contributions and limitations
- Non-deductible IRA contributions and the “Back-Door” Roth IRA strategy
- Tax reporting implications of contributions to be mindful of
- Roth 5-Year Clock for Roth IRA contributions
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
The key moments in this episode are:
00:00:00 - Understanding Traditional and Roth IRAs 00:01:28 - Critical Information for Retirement Planning 00:03:00 - Pre-tax and Tax-deferred Retirement Accounts 00:04:10 - Contribution Limits and Eligibility Requirements 00:06:01 - Strategies for Capitalizing on Contribution Opportunities 00:16:48 - IRA Contribution Deadlines 00:17:18 - Maximizing Contributions 00:18:25 - Income Fluctuations and Planning 00:19:44 - Pro Tips for Contributions 00:27:34 - Tax Implications and Reporting 00:32:32 - Understanding the Pro Rata Rule 00:33:36 - The Five Year Rule for Roth IRA Contributions 00:35:31 - Starting the Five-Year Clock 00:36:22 - Seeking Professional Retirement Planning Advice 00:38:18 - Risks and Considerations in Retirement Planning
When looking into getting extra healthcare coverage beyond the basic coverage provided by Original Medicare Parts A and B, you’ll have to choose between either a Medicare Advantage Plan or a Medicare Supplement Plan also known as Medigap.
One isn’t necessarily better than the other, they each have their place in the market. In order to make the decision on which one you should go with; you should have some basic level of financial planning done ahead of time since the route you choose to go can have a significant effect on the potential out of pocket costs you pay for healthcare over the remainder of your retirement.
More specifically, I discuss:
- Summary of Medicare Advantage Plans and Medicare Supplement Plans (aka Medigap)
- How Medicare Advantage Plans work compared to Medicare Supplement Plans
- How the decision between the two route of additional coverage coordinate with your overall retirement plan
- The pros and cons of Medicare Advantage Plans
- The pros and cons of Medicare Supplement Plans
- How prescription drug coverage works depending on the route you take
- How to go about making a decision regarding which type of additional coverage to go with
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
The key moments in this episode are: 00:00:00 - Understanding Medicare Advantage and Medicare Supplement Plans
00:01:46 - Original Medicare Coverage and Additional Healthcare Costs
00:04:04 - Pros and Cons of Medicare Advantage Plans
00:10:51 - Limitations and Risks of Medicare Advantage Plans
00:15:28 - Understanding MA Plans and Drug Coverage
00:17:35 - Exploring Medigap Plans
00:20:14 - Pros and Cons of Medigap Plans
Large pre-tax retirement accounts such as Traditional IRAs, 401(k) plans and the like are great savings vehicles for retirement. The problem is, they make for lousy and tax laden estate planning.
The tax authorities have a claim to the money in these accounts, and the retirement and tax laws surrounding them are very complex and ever-changing.
This requires careful strategizing if you have large balances in pre-tax retirement accounts in order to pass this money in a tax-efficient manner to your surviving spouse, children, or favorite charitable organizations.
In the end it’s not about how much you’ve accumulated, it’s about how much you keep.
More specifically, I discuss:
- The tax authorities and your retirement account: The Distribution Phase vs. Accumulation Phase
- Understanding what will happen to pre-tax retirement accounts when inherited
- A summary of the new retirement and tax laws that complicate retirement accounts and estate planning:
- Adult children as beneficiaries of your retirement account
- A surviving spouse as beneficiary of your retirement account
- Other types of beneficiaries such as a charity
- Strategies to consider in order to pass more of your unused retirement savings to a spouse and other beneficiaries
- Trusts as beneficiaries of retirement accounts
- Additional considerations and things to avoid
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump-Start Analysis
- Ask Cameron A Question!
The key moments in this episode are:
00:00:00 - Importance of Estate Planning for Retirement Accounts 00:02:13 - Complex Retirement and Tax Laws 00:04:20 - Challenges of Passing Wealth Efficiently 00:08:01 - Inheriting Retirement Accounts and Tax Implications 00:13:00 - Strategies for Beneficiaries 00:16:18 - Options for Spouse Beneficiaries 00:19:27 - Charitable Considerations 00:22:09 - Leaving Retirement Accounts to Trusts 00:25:27 - Things to Avoid and Consider 00:27:51 - Additional Guidance and Resources
One out of four people that experience divorce in the United States is age 50 or older, and nearly one out of ten is age 65 or older. These later-in-life separations is commonly referred to as Gray Divorce, and with it often comes complex financial situations.
By properly creating a thorough financial affidavit during the divorce process, you can significantly increase your confidence in your financial independence post separation.
More specifically, I discuss:
- What is a financial affidavit?
- Who prepares a financial affidavit?
- What should you include in your financial affidavit to prepare you for negotiations?
- The role of an attorney and financial professional in the divorce process
- Common mistakes made when preparing a financial affidavit and how to address them
- Where to get help if needed
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump Start Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are:
00:00:00 - Gray Divorce and Financial Complexity
00:03:55 - Importance of Financial Affidavit
00:08:40 - Preparation and Consultation
00:11:50 - Long-Term Financial Impact
00:15:16 - Post-Divorce Financial Planning
00:18:12 - Considerations for Traditional IRA to Roth IRA Conversion
00:18:44 - Risks and Considerations in Bond Investments
00:19:17 - Tax Implications and Asset Allocation
00:19:35 - Importance of Tax Advisor and Diversification
By having a better understanding of your tax situation, you are more likely keep more of your hard-earned money, which can also mean you don’t have to rely as much on exuberant investment returns.
Moving to another state in order to potentially save money in taxes can have a huge impact on your finances in retirement by allowing your money to go further, which means less stress on your income producing assets throughout a potential 20–30-year retirement.
In this episode we discuss the various tax implications you’ll want to know when deciding where to enjoy your retirement years!
More specifically, I discuss:
- Some of the major tax differences between states
- How income taxes differ between states
- How different states tax different types of retirement income such as Social
- Security, IRA/401(k) distributions, pensions, and capital gains
- State tax nuances of Health Savings Accounts (HAS)
- State deductions, credits, income exemptions, and property tax exemptions
- Sales tax differences between states and localities
- Property tax considerations when making a move
Resources:
- Access Show Notes and Sign Up for the Retired·ish Newsletter HERE
- Free Retirement Jump Start Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are: 00:00:00 - Importance of Estate Planning for Retirement Accounts
00:02:13 - Complex Retirement and Tax Laws
00:04:20 - Challenges of Passing Wealth Efficiently
00:08:01 - Inheriting Retirement Accounts and Tax Implications
00:13:00 - Strategies for Beneficiaries
00:16:18 - Options for Spouse Beneficiaries
00:19:27 - Charitable Considerations
00:22:09 - Leaving Retirement Accounts to Trusts
00:25:27 - Things to Avoid and Consider
00:27:51 - Additional Guidance and Resources
While the vast majority of people will choose to live in the same home once they retire, many more housing opportunities typically open up during your retirement years due to kids being out of the home - hopefully – and the fact that you don’t have any obligations to show up to any specific workplace or maybe you’re now able to work on your own terms from the comfort of your own home.
In this case, Snowbirding by splitting time between two homes might be ideal dream retirement for you.
However, you’ll want to keep in mind the many financial and tax challenges that you’re likely going to run into. In this episode, we review the snowbird implications many people don’t think of when taking the leap!
More specifically, I discuss:
- Non-financial considerations when maintaining two homes
- Affordability when it comes to owning vs renting
- Various tax implications & establishing residency
- Costs of maintaining multiple residences
- Healthcare costs and coverage complexities
Resources:
- Access Show Notes HERE
- Free Retirement Jump Start Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are:
00:00:35 - Housing Opportunities in Retirement
00:02:19 - Nonfinancial Considerations of Snowbirding
00:04:33 - Buying vs. Leasing Property
00:09:39 - Establishing Residency
00:15:14 - Managing Mail and Utilities for Snowbird Living
00:16:10 - Hypothetical Cost Example for Snowbird Living
00:17:22 - Considerations for Healthcare and Insurance
00:18:46 - Liquidity and Overspending Considerations
00:20:38 - Planning and Professional Involvement for Snowbird Lifestyle
There typically comes a time when your income sources drastically change from one source to another, or from one to multiple sources.
For most, this will be shifting from earning income from a career, to then living off your own savings, potential pensions, or even passive income from real estate or businesses.
During this phase of life is when you have the opportunity to capitalize on tax planning and reduce your lifetime tax bill substantially!
More specifically, I discuss:
- Planning early enough to be able to implement tax savings strategies.
- Getting strategic about when you claim Social Security for lifetime tax savings.
- Tax planning strategies for retirement accounts.
- Preserving your capital gains from taxation.
- Roth conversions during your “gap years”.
Resources:
- Access Show Notes HERE
- Free Retirement Jump Start Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are:
00:01:15 - The Art of Paying Less Taxes
00:03:15 - Importance of Early Retirement Planning
00:05:54 - Differentiating Tax Preparers and Tax Planners
00:08:31 - Strategic Social Security Benefits and Tax Planning
00:14:37 - Tax Planning Strategies for Retirement Accounts
00:15:48 - Shielding Capital Gains from Taxation
00:17:13 - The Importance of Long-Term Planning
00:18:55 - Delaying Social Security and Tax Implications
00:24:01 - Roth Conversions and Tax Savings
00:30:13 - Investment Strategies and Services
00:30:44 - Considerations for Roth IRA Conversion
00:31:16 - Risks and Considerations for Bonds
00:32:03 - Tax and Legal Advice Disclaimer
If you have an aging parent, there’s a high likelihood that you will eventually need to step in to help them with their caretaking and financial decision making.
There are many steps you can take to protect their finances and well-being as long as these steps are taken ahead of time so that everyone’s better prepared. Many of these things you should actually be doing for yourself, such as making sure you don’t pay more than you need to in taxes, having a plan for care as you get older, and simply making sure your finances are managed in a way that benefits you in the long run.
By being prepared, mom, dad, and even you can enjoy life in retirement to the fullest.
In this episode we discuss what to expect and the steps you can take to be better prepared.
More specifically, I discuss:
- How to better prepare an aging parent for potential financial elder abuse
- The power and uses for a financial power of attorney (POA)
- How to prepare mom or dad financially ahead of key financial threats during retirement
- Examples of common mistakes made when paying for caretaking
- Protecting more of mom or dad’s income from the IRS
Resources:
Access Show Notes HERE Free Retirement Jump Start Analysis for Ages 50+ Ask Cameron A Question!
The key moments in this episode are:
00:02:10 - Elder Abuse
00:04:52 - Family Loans
00:06:13 - Financial Power of Attorney
00:09:20 - Types of POAs
00:15:12 - Planning for Long-Term Care
00:16:31 - Who Will Take Care of Mom?
00:17:20 - Long-Term Care Insurance and Self-Insuring
00:19:17 - Sequence of Returns Risk and Investing
00:20:46 - Considerations with Real Property
Women have unique challenges that they typically face in retirement, and although men have their own share of obstacles to face, women tend to juggle more than just worrying about themselves and their own livelihood.
This phenomenon is mostly due to the fact that many women today are part of a “sandwich generation” in which they typically support themselves, their children, and often times aging parents. This makes retirement a lot more challenging, especially when life throws a wrench in the mix such as divorce, or the death of a spouse.
In this episode we discuss what to expect and the steps you can take to be better prepared.
More specifically, I discuss:
- Why women tend to face their own unique obstacles for retirement
- How statistically living longer than men presents financial challenges
- How temporarily leaving the workforce to care for others can affect your finances in a major way
- Why investing on your own is paramount to sustaining the lifestyle you desire throughout retirement
- Understanding risk and why being “too conservative” when investing can hurt you in the long run
- Common mistakes made during the divorce process and negotiations How to mitigate elder abuse in your later retirement years
Resources:
- Access Show Notes HERE
- Free Retirement Jump Start Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are:
00:00:00 - Unique Challenges Faced by Women in Retirement 00:03:08 - Longer Life Expectancy and Financial Stress 00:04:51 - Earning Less and the Sandwich Generation 00:06:12 - Investing Knowledge and Risk Tolerance 00:09:51 - Common Mistakes in Divorce Settlements 00:16:00 - Importance of Understanding Investments and Goals 00:16:45 - Importance of Insurance Coverage 00:17:21 - Importance of Organizing Important Documents 00:18:26 - Seeking Professional Help 00:19:37 - Risks in Investing and Asset Allocation
Our emotions impact our investing decisions when it comes to the stock markets. In this episode, I share a thought experiment to help you understand how to make your investing decisions.
More specifically, I discuss:
- With everything going on in the world, why would anyone still invest in the stock market?
- When fear and uncertainty are at a peak, how do I go about making investment decisions?
- Thought experiments to go through before reacting
- What Crisis have we been through in recent history?
- What advances have we made in recent history?
- What really is “the stock market”?
- Factual data regarding the US stock market over the past several decades
Resources:
- Access Show Notes HERE
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are:
00:00:00 - The Current State of Affairs
00:01:26 - Reacting to Fear and Uncertainty
00:03:11 - Fears in Retirement
00:06:27 - Reflecting on Investment Goals
00:10:11 - The Role of Facts
00:14:53 - Probability of Positive Returns Over Time
00:16:14 - Importance of Best Days in the Stock Market
00:17:17 - Potential Downturns and Long-Term Returns
00:18:03 - Importance of Reevaluating Goals and Financial Plans
00:18:51 - Conclusion and Call to Action
I discuss the common options you have for health insurance coverage when retiring before you are Medicare eligible at age 65.
More specifically, I discuss:
- Jumping on Your Spouse’s Employer Health Plan
- Considering Shopping The Health Insurance Marketplace – Affordable Care Act
- Continuing Coverage Through The Consolidated Omnibus Budget Act – COBRA
- Looking into Healthcare Cost-Sharing Arrangements or “Faith-Based” Plans
- Retiree Health Plans Through a Former Employer in the Public Sector, Government, or Military
Resources:
- Access Show Notes HERE
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are:
00:00:00 - Planning for Health Insurance Coverage in Retirement
00:03:22 - Spouse's Employer Group Health Plan
00:04:36 - COBRA Continuation Coverage
00:06:55 - Health Insurance Marketplace
00:10:43 - Choosing Coverage via the Marketplace
00:14:47 - Health Coverage Options for Retirees
00:15:57 - Considerations for Spouses
In this episode, I discuss some of the financial strategies you can implement into your own personal finances as the recipient of a financial windfall from a parent.
More specifically, I discuss:
- Strategies when inheriting property from a parent
- Strategies when inheriting cash and investments from a parent
- Tax considerations and planning when inheriting various types of assets
- How and why these strategies may be beneficial to you
- How to incorporate these strategies into your own personal finances
- Avoiding reckless spending and burning through a potential inheritance
Resources:
- Retired-ish Newsletter Sign-Up
- Begin Creating Your Own Financial Map After An Inheritance
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
- Get Episode Show Notes Here
The key moments in this episode are:
00:00:00 - Incorporating an Inheritance into Your Life
00:01:46 - Strategies for Inheriting Property
00:06:47 - Selling Inherited Property
00:11:31 - Managing Cash Proceeds
00:14:46 - Allocating Inherited Money
00:15:55 - Tax Planning and Roth IRAs
00:18:14 - Benefits of Funding Roth IRAs
00:20:36 - Inheriting Pretax Retirement Accounts
00:25:13 - Having a Plan for Inherited Money
I discuss the potential pitfalls to watch out for when inheriting assets from a parent. Receiving an inheritance isn’t the same as maximizing an inheritance, as you could lose a significant portion if you’re not prepared.
More specifically, I discuss:
- What are common types of assets that are passed down to the next generation?
- What are the common pitfalls to watch out for when inheriting property?
- How should assets be titled before they are passed down?
- What impact do trusts have on an inheritance?
- How do taxes work when inheriting assets?
- What are the common pitfalls to watch out for when inheriting retirement accounts?
- What are the common pitfalls to watch out for when inheriting non-retirement accounts?
Resources:
- Retired-ish Newsletter Sign-Up
- Begin Creating Your Own Financial Map After The Loss of A Parent
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are:
00:00:00 - Introduction and Importance of Understanding Inheritance
00:00:57 - Projected Increase in Inherited Wealth
00:02:12 - Assumptions about Parental Financial Planning
00:03:36 - Common Types of Inherited Assets
00:05:27 - Pitfalls of Inheriting Property
00:14:28 - Considerations for Inheriting Property
00:15:48 - Retirement Accounts and the Secure Act
00:19:37 - Tax Considerations for Inherited Retirement Accounts
00:21:28 - Handling Non-Retirement Investment Accounts
00:25:35 - Importance of Understanding Inheritance Planning
In this episode, I discuss potential Social Security Survivor Benefits available to a spouse and other family members after the loss of a loved one. Everyone’s situation is unique in that they will typically have many options when it comes to deciding how and when to apply for these benefits which could be the difference of tens if not hundreds of thousands over a lifetime.
More specifically, I discuss:
- What are Social Security Survivor Benefits? How do you know if you are eligible for Survivor Benefits?
- How are Survivor Benefit amounts determined?
- What are some complications that can affect the benefits you may be entitled to?
- Other than a spouse, what other family members may be able to qualify for Survivor Benefits?
- How the “Family Maximum” can affect benefits paid when multiple dependents are collecting a benefit on a deceased’s record.
- A checklist to review before reaching out to Social Security to apply for Survivor Benefits
Resources:
- Retired-ish Newsletter Sign-Up
- Begin Creating Your Own Financial Map After The Loss of A Loved One
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
- Access Resources from This Episode
Cameron Valadez and Planable Wealth are not affiliated with or endorsed by the U.S. Social Security Administration or any government agency. The Social Security Administration provides free Social Security forms, publications, and assistance.
The Bucket Strategy, also know as Time Segmenting, is a simple and effective strategy to implement approaching retirement. This simple yet effective strategy allows you to assign a purpose to your various assets so you can understand how to enjoy the financial benefits they can provide.
More specifically, I discuss:
What is the “Bucket Strategy” aka “Time Segmenting”
What is “Sequence of Returns Risk”?
How Can The Bucket Strategy Help Alleviate Sequence of Returns Risk?
Developing a Bucket Plan
How Implementing a Bucket Plan Can Potentially Increase The Longevity of Your Retirement Income
For more resources and information, visit the show notes at https://retiredishpodcast.com/26
The key moments in this episode are:
00:03:54 - Preventing Sequence of Returns Risk
00:09:09 - The Three Buckets
00:12:26 - Goals of the Third Bucket
00:15:10 - Implementing the Bucket Strategy
00:16:37 - Tax Considerations and Asset Allocation
00:18:31 - Superiority of the Bucket Strategy
00:19:39 - Implementation and Management
Revealing the mysteries around financial planning: What it means, what it can do for you, and what the process looks like. I also discuss the problem with simply knowing or researching things rather than using information to implement in your own life.
More specifically, I discuss:
- What is Financial Planning? – Personal/Retirement
- What Are The Steps to Creating a Financial Plan?
- Examples of What to Consider When Creating Your Plan
- The Implementation of Information and Strategies
- What Can Financial Planning Do For You?
Resources:
- Retired-ish Newsletter Sign-Up
- Begin Creating Your ONE-PAGE Financial Map
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
The key moments in this episode are:
00:00:50 - Types of Financial Planning
00:02:17 - The Purpose of Financial Planning
00:04:58 - The Process of Financial Planning
00:09:07 - Importance of Getting Organized
00:14:37 - The Importance of Open-Mindedness in Financial Planning
00:14:59 - The Sign of a Completed Plan
00:15:51 - The Most Important Step: Implementation
00:17:23 - The Value of Assistance in Staying Consistent
00:19:01 - Continuous Monitoring and Course Correction
Learn how your business may be able to help you save more in taxes!
In this episode, I’m joined by Mike Jesowshek, CPA and host of the Small Business Tax Savings Podcast as we discuss how to unlock the true benefits of an S-Corporation.
Having a better understanding of your business shouldn’t be complicated. Whether you’re new to the business world, or semi-retired with a thriving family business, this episode is packed with strategies presented “in crayon” just for you.
More specifically, we discuss:
- What is an S-Corporation, and how does it work?
- What are the main tax benefits of an S-Corporation election?
- Who should consider an S-Corp election, and who shouldn’t? What are possible disadvantages?
- What are the costs associated with being taxed as an S-Corporation?
- How should you run and manage your S-Corporation?
- What do business owners need to know before stepping away from their business?
- Tax strategies you can implement in your business:
- Maximizing everyday deductions
- Retirement plan
- Charitable giving
- Hiring your children
Resources:
- Mike’s Podcast: Small Business Tax Savings Podcast
- Retired-ish Newsletter Sign-Up
- Ask Cameron A Question!
- Free 4-Step Retirement & Tax Analysis for Ages 50+
- Additional Episode Related Resources Here
LPL Financial and Planable Wealth are not affiliated with or endorsed by Mike Jesowshek or the Small Business Tax Savings Podcast.
In practice, I have found many people think they are diversified looking at the surface, but come to find out their investments have very little to no diversification. In this episode, I discuss the benefits of diversifying your investment portfolio and the common myths around diversification.
More specifically, I discuss:
- What does it mean to be truly diversified?
- What can diversification do for you?
- What should you expect by diversifying appropriately?
- Common, real-world examples of “pseudo diversification”
- What not to do when trying to diversify your investments, and alternative approaches
- Why alternative investments don’t belong in a retiree’s investment portfolio
Resources mentioned, which you can get at http://retiredishpodcast.com/23:
- Retired-ish Newsletter Sign-Up
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
In this episode, I discuss the key facts that you need to know about Social Security benefits after divorce.
More specifically, I discuss:
- What are the requirements to receive Social Security benefits based on an ex-spouse’s record?
- How much can you receive as a former spouse?
- What if your ex-spouse dies before or after you begin receiving Social Security benefits?
- Can you start collecting an ex-spousal benefit if your ex is not taking Social Security yet?
- What happens to Social Security benefits if you remarry?
- Does the Social Security annual earnings test apply to benefits you receive as a former spouse or survivor?
Resources mentioned can be found in the show notes at https://retiredishpodcast.com/22
I’m joined again by Long-Term Care expert, Hospital Discharge Planner, and Geriatric Care Manager Eileen Dunn where we guide you through what to expect during the claims process for long-term care insurance.
More specifically, Eileen and I discuss:
- When is it time to make a long-term care insurance claim?
- What are some reasons why someone may be denied a long-term care insurance claim?
- How long does it typically take between initiating a claim and actually getting approval?
- Who pays the care provider, you or the insurance company?
- How does a waiver of premium work?
- How does an elimination period work?
Resources can be located at https://retiredishpodcast.com/21
LPL Financial and Planable Wealth are not affiliated with or endorsed by Eileen Dunn
I’m joined again by Long-Term Care expert, Hospital Discharge Planner, and Geriatric Care Manager Eileen Dunn where we educate you on how to determine how much long-term care insurance you may need, and what factors you should consider.
More specifically, Eileen and I discuss:
- Factors that influence the amount of long-term care insurance you may need
- How to find the cost of care in your area
- How to calculate your “Insurance Gap”
- Tax considerations when calculating your insurance needs
- How a professional can help you plan for long-term care
For helpful links to resources mentioned, visit the show notes at https://retiredishpodcast.com/20
I’m joined again by Long-Term Care expert, Hospital Discharge Planner, and Geriatric Care Manager Eileen Dunn where we discuss the basics of long-term care insurance and the Long-Term Care Partnership Program.
More specifically, Eileen and I discuss:
- Why should you consider long-term care insurance?
- What does long-term care insurance pay for?
- Common types of long-term care insurance policies
- Cost and benefit considerations of long-term care insurance
- Long-Term Care Partnership Programs
- Taxation of long-term care benefits
Resources:
- Retired-ish Newsletter Sign-Up
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
LPL Financial and Planable Wealth are not affiliated with or endorsed by Eileen Dunn or Mutual of Omaha.
What is long-term care & how does it work? In this episode, I’m joined by Long-Term Care expert, Hospital Discharge Planner, and Geriatric Care Manager Eileen Dunn to educate us on the basics and realities of long-term care from a “boots on the ground” perspective.
More specifically, Eileen and I discuss:
- What is Long-Term Care?
- What Qualifies Somebody for Long-Term Care?
- Does Medicare Pay for Long-Term Care?
- Does Medicaid Pay for Long-Term Care?
- What Kind of Care Are People Actually Getting?
- Adult Children Helping Mom and Dad
- Having The Tough Conversation About Long-Term Care Planning
Resources:
- Retired-ish Newsletter Sign-Up
- Free 4-Step Retirement Analysis for Ages 50+
- Ask Cameron A Question!
- Access Episode Show Notes Here
In this episode I’m joined by mortgage lending expert John Stanfield with Viewpoint Financial as we dispel some of the myths about rental property investing so you can decide how you want to approach given your own situation and investing preferences. And while a portfolio of rental properties can absolutely generate wealth and income in retirement, there is no one size fits all solution as everyone will have different opportunities, situations, and skill sets.
Together we share various tips and considerations rental property owners should consider, and John will also be sharing with us some of the options you have to acquire real properties with financing should you decide to use them as part of your retirement income and wealth accumulation strategy. John Stanfield is a mortgage broker with a decade of experience. John began his career in underwriting and funding on the operations side of the industry before moving to the consumer facing side where he originated loans for individuals where he has been ever since. John has earned accolades from United Wholesale Mortgage as being among the top 1% of fastest purchase transaction closers in 2020, 2021, and 2022. His passion for helping clients achieve their homeownership dreams has driven his success thus far, and he continues to be a respected and sought-after professional in the mortgage industry.
More specifically, John and I discuss:
- What Are The 4 Components to the Rate of Return on Rental Real Estate?
- What Are Some of The Main Pros and Cons to Investing in Rental Property in Retirement?
- What Are Some Common Ways to Get Financing for a Rental Property?
- What Are Some Potential Ways to Protect Your Rental Property & Your Other Assets?
- Other Insights and Considerations For Those Who Are Considering Owning Rental Properties Throughout Retirement
Resources:
- Retired-ish Newsletter Sign-Up
- Free 4-Step Retirement Analysis for Ages 50+
- Access the Show Notes Here
At some point nearing retirement, retirees often wonder: Are annuities a good idea for retirees?
The internet and world-at-large is full of conflicting information about annuities, and whether or not they make sense for today’s retiree.
The topic of annuities is definitely an interesting one since many retirees are in one or two camps:
- They either don’t know much at all about them,
- Or they completely fear and avoid them due to a horror story they read on the internet about someone else’s experience with an annuity.
Heck, even financial professionals have wildly different opinions on annuities and whether or not they are worth the benefits they can provide.
Some professionals love them, some hate them. I’m not here to settle that score, but to let you decide since ultimately people value different things differently.
More specifically, I discuss:
- Why Would a Retiree Consider an Annuity in The First Place?
- What is an Annuity? What is a Deferred Income Annuity?
- Pros and Cons to Annuities for Retirement
- Cost Considerations With Annuities
- Practical Uses of Income Annuities
Resources:
- Access Show Notes Here!
Sources:
- https://www.oecd.org/newsroom/healthier-lifestyles-and-better-health-policies-drive-life-expectancy-gains.htm (October 2017)
- R-P 2000 Mortality Table, Society of Actuaries
Plain and simple, your retirement income plan will make or break you in retirement. In this episode, we discuss the importance of creating an actual plan that focuses solely on how you will get your income in retirement, and the greatest risks your income will face.
An appropriately structured income plan is crucial so that you can avoid entering retirement being uncertain about how much you can spend each month, vulnerable to the big retirement risks, and unstructured with your nest egg – meaning that you really have no idea how to arrange your affairs, what accounts to have, what investments to select, and what accounts they should go in.
Your retirement income will drive your lifestyle, not necessarily the amount of money you have. The more confidence you have in your retirement income plan, the more likely you will live a happy and fulfilling lifestyle that allows you to focus on the more important things in life.
More specifically, I discuss:
How to Determine of You Are a Constrained Investor The #1 Danger of “The 4% Rule” Retirement Timing Risk (Sequence of Returns Risk) Explained Inflation and Longevity Risk Advantages of Segmenting or Bucketing Your Nest Egg
For resources, go to https://retiredishpodcast.com/14
In this episode, we show you how to spot shadow taxes which are hidden taxes you may pay without a trained eye. These are taxes and penalties hidden from plain sight that many people pay, although there are numerous ways to reduce or avoid them entirely.
More specifically, I discuss:
- The Repayment of Advanced Excess Premium Tax Credit
- The Net Investment Income Tax
- Medicare IRMAA Surcharges on Medicare Part B & D Premiums
- Additional Taxes Owed on Social Security
- Ways to Reduce or Avoid Shadow Taxes
Resources:
Free 4-Step Retirement Analysis for Ages 50+ Retired-ish Newsletter Sign-Up Episode Show Notes
In this episode we will go through a process that will help you figure out what to do when an elderly parent or a spouse dies.
This is especially useful if you are the named executor of an estate, or trustee or successor trustee of a trust for the deceased since you will be the one who will aid in determining and/or delivering on their wishes.
More specifically, I discuss:
- What immediate tasks must be done when an elderly parent or spouse dies?
- What important documents to look for when organizing an estate
- What people and organizations to reach out to and why
- What is probate and is it required?
- How does a trust work when settling an estate?
- General guidance on what the process of distributing an estate looks like
For more information and resources, visit the show notes at https://retiredishpodcast.com/13
Bonds are very misunderstood by most retirees and investors alike simply because they don’t get much love and attention, but bonds are actually very simple, more-so than stocks. In this episode, I teach you some interesting, exciting, and actionable things about them you may not have known that can help you. My goal is for you to better understand the role bonds can play in your portfolio, and when you might consider them in retirement.
More specifically, I discuss:
- How do bonds work?
- What are the different types of bonds?
- What are the different ways to invest in bonds?
- How do taxes work on bonds?
- What role do bonds play in a retirement investment portfolio?
- Key considerations for bond investors
Resources:
- Free Retirement Analysis for Ages 50+
- Retired-ish Newsletter Sign-Up
- Quick Guide: 2023 Important Numbers
- Free 4-Step Retirement Analysis for Ages 50+
Estate planning in retirement can be a daunting task. The problem is that most of us put off this aspect of retirement planning because it doesn’t raise an immediate need. The truth is that estate planning is much more than a will and trust and can have a dramatic effect on your legacy, for better or worse. In this episode we discuss what estate planning is, and the little things you can do to pass a meaningful legacy to your family.
More specifically, I discuss:
- What is estate planning?
- What does a well-thought-out estate plan look like?
- What are the common components of an estate plan?
- Estate planning tips you never thought of
- Identifying what you want your legacy to be
- Identifying the ultimate PURPOSE of your wealth
Resources:
Get Show Notes Here Free Retirement Analysis for Ages 50+ Retired-ish Newsletter Sign-Up
Roth conversions are a great strategy that you can use to help build up your “tax-free” bucket in order to provide you with more flexibility in retirement. Having more tax-free money can help you avoid tax time-bombs, maintain some control of your taxable income in retirement, or even be used as an excellent legacy to pass down to heirs.
More specifically, I discuss:
- Our upcoming “Retirement Planning Today” classes in February 2023
- The main differences between a Roth IRA and Traditional IRA or other pre-tax account
- What is a Roth conversion?
- What are the main reasons to consider doing a Roth conversion?
- Pitfalls to look out for when doing a Roth conversion
- Strategies on how to pay potential taxes owed on a Roth conversion
Resources:
- Get Show Notes Here
- Free Retirement Analysis for Ages 50+
- Retired-ish Newsletter Sign-Up
Medicare is a daunting program to understand for most retirees. In this episode we break down the different components and additional coverage options in layman’s terms. Having a good understanding of the different options and various costs components can provide you with more confidence in your healthcare plan during retirement.
More specifically, I discuss:
- What is Medicare, and what are the main components
- What does Medicare pay for?
- What types of additional coverage are available? What are the costs?
- The difference between Medicare Advantage Plans (Part C) and Medicare Supplement Plans (Medigap), and some of the pros and cons of each.
- What factors should you consider when making coverage decisions?
Get Show Notes and Resources Here https://retiredishpodcast.com/9
The greatest threat to your life savings is lurking in the shadows ready to strike when you least expect it. This threat presents itself when going from saving to spending your retirement nest-egg - which is nerve wracking for a new retiree. This phase of your financial journey is far more complicated than simply putting money away year-in and year-out and is susceptible to major threats such as sequence of returns risk.
More specifically, I discuss:
- What is the greatest threat to your retirement savings?
- Examples of sequence of returns risk in the savings phase of your life
- Examples of sequence of returns risk in the spending phase of your life
- The difference between monitoring account balances vs. average investment returns
- What types of strategies can you implement to aim to reduce sequence of returns risk
For the links and extras mentioned in the episode, please visit the show notes page at https://RetiredishPodcast.com/8
Retired-ish Newsletter Sign-Up Get Show Notes Here
There are many nuanced factors to consider when creating a retirement investment portfolio. In this episode I go over some of the more important foundational building blocks, and how to begin the process of creating a retirement portfolio for you.
More specifically, I discuss:
- Identifying a specific purpose for your different accounts, based on your financial plan
- Factoring in personal preferences when determining your portfolio allocation
- The goal of diversification
- Types of asset allocation
- Asset location and practical use cases
For the links and extras mentioned in the episode, please visit the show notes page at retiredishpodcast.com/7
- Retired-ish Newsletter Sign-Up
- Roth 5-Year Rules
Financial markets are scary… and we humans make decisions largely based on our current emotions. Mixing those two things together, and you get a toxic concoction.
Investing should be based upon us acting on our own rational and intellectual thoughts, but it hardly ever is… So rather than staring at markets and making emotional decisions, what can we actually do to better the outcomes of our financial situations?
More specifically, I discuss:
- How to “check yourself” when markets are volatile and declining
- What investments you probably shouldn’t have
- Using bad markets to get rid of tax inefficient investments
- Recency bias
- Buy out the government’s share of your retirement account at a lower cost
- How to take less risk going forward in order to pursue your retirement income goals
- Buy low, sell high
For the links and extras mentioned in the episode, please visit the show notes page at retiredishpodcast.com/6
Taking the proper steps early to prepare yourself for one of life’s biggest transitions can alleviate much unwanted stress and…save you money.
In this episode I continue the conversation on taxes and how they can be paid in retirement, what to do with your retirement accounts when you retire, and some tips to help you make healthcare decisions around retirement.
More specifically, I discuss:
- Estimated tax payments and withholdings in retirement
- How to make estimated tax payments in retirement
- Retirement plan rollovers, cashing out, and direct rollovers from 401(k) plans to IRAs and Roth IRAs along with some pros and cons of doing so
- The greatest risk to your retirement nest egg: “Sequence of Returns Risk”
- The healthcare marketplace, COBRA, and Medicare
- Accumulated vacation/sick pay and year-end bonuses from your employer
For the links and extras mentioned in the episode, please visit the show notes page at retiredishpodcast.com/5
- Podcast: Preparing for Retirement Pt. 1
- Retired-ish Newsletter Sign-Up
- Roth 5-Year Rules
- How to Make Estimated Payments Online
- Do I Need to Make Estimated Payments Flowchart - 2022
- Blog: “Sequence of Returns: The Greatest Risk to Your Retirement Savings”
- Will Healthcare change as I transition into retirement? - 2022
- If I retire early, should I buy health insurance through the health insurance marketplace?
- Social Security withholding form – W-4V
Cameron Valadez and Planable Wealth are not affiliated with or endorsed by the U.S. Social Security Administration or any government agency. The Social Security Administration provides free Social Security forms, publications and assistance.
Taking the proper steps early to prepare yourself for one of life’s biggest transitions can alleviate much unwanted stress and…save you money.
The first step in preparing for retirement is determining if you are actually ready. In this episode I go over what you can do to determine your retirement readiness along with a host of other important financial planning considerations.
More specifically, I discuss:
- “Practicing” retirement
- The importance of an emergency fund specifically for retirees, and how to structure it
- Cash savings ideas to implement tax savings strategies while in retirement
- Various types of retirement income, and how to structure them to meet your needs
- Understanding YOUR tax situation in retirement, and how taxes affect your income sources
In part 2 of the Preparing for Retirement series we will continue the discussion with:
- Tax withholding on retirement income sources
- What to do with retirement accounts
- Healthcare in retirement and Medicare
- Managing expenses in retirement and tips to reduce them
- The timing implications of your retirement from the workforce and last minute considerations
For the links and extras mentioned in the episode, please visit the show notes page at https://retiredishpodcast.com/4
- Retired-ish Newsletter Sign-Up: https://lp.constantcontactpages.com/su/VjiTbE7/retiredish
- Checklist - What Issues Should I consider Before I Retire 2022: https://www.planablewealth.com/wp-content/uploads/2022/01/What-Issues-Should-I-Consider-Before-I-Retire-2022.pdf
- 5 Advantages of a Roth IRA: https://www.planablewealth.com/blog/retirement/5-advantages-roth-ira
- Roth 5-Year Rules: https://www.planablewealth.com/blog/retirement/roth-ira-and-roth-401k-5-year-rules
Let’s go over two little known Social Security strategies and the long-term implications of each.
In this episode, I discuss why Social Security is paying out lump sum payments to retirees and the pitfalls of taking the payment, as well as a strategy to tap into benefits early and rebuild them later.
I also review tax and estate planning issues that may be caused as a result of implementing these strategies, and where they can make sense to take advantage of.
For the links and extras mentioned in the episode, please visit the show notes page at https://retiredishpodcast.com/3
Retired-ish Newsletter Sign-Up: https://lp.constantcontactpages.com/su/VjiTbE7/retiredish
Find your Full Retirement Age: https://www.ssa.gov/benefits/retirement/planner/ageincrease.html
Retroactive Benefits: https://secure.ssa.gov/poms.nsf/lnx/0501130600
Social Security Payment Withholding Form W4-V: https://www.ssa.gov/benefits/retirement/planner/taxwithold.html
Episode #2: How to use tax gain AND loss harvesting to your advantage. If done appropriately, tax gain/loss harvesting can help you reduce taxes, thereby keeping more money in your pocket which can help you increase your net worth! More specifically, I discuss: Tax loss harvesting with examples Tax GAIN harvesting with examples Capital gains and losses When it’s a good idea to implement this tool Common pitfalls to avoid when tax harvesting is implemented What is a capital loss carry-forward and how to use it
For the links and extras mentioned in the episode, please visit the show notes page at https://retiredishpodcast.com/2
How Capital Gains Tax Works https://www.planablewealth.com/blog/tax-planning/how-capital-gains-tax-works
2022 Important Numbers https://www.planablewealth.com/wp-content/uploads/2021/11/2022-Important-Numbers.pdf
Episode #1: Don’t add the IRS to your list of beneficiaries! Here are 5 of my favorite tax and estate planning tips when it comes to retirement accounts including IRAs and employer plans!
You’ll also learn:
- What your Required Beginning Date or RBD is, and why it is so important
- What is a Required Minimum Distribution or RMD, and how it affects your financial planning
My goal for these retirement tips is to help you preserve more of the wealth you worked so hard for.
My top 5 favorite retirement account tips are:
- Retirement accounts pass by contract or operation of law, not your will.
- When inheriting an IRA as a spouse, make sure to title it properly pursuant to your goals!
- If the original retirement account owner passed their Required Beginning Date (RBD) and did not take an RMD in the year of their death, the beneficiary(ies) needs to take it!
- If you and your spouse both have large retirement account balances, consider what I call a “spousal skip strategy” for your beneficiary designations.
- Understand the Required Minimum Distribution Rules with Roth 401(k)s vs Roth IRAs
For the links and extras mentioned in the episode, please visit the show notes page at: https://retiredishpodcast.com/1
Guide to inheriting an IRA (https://www.planablewealth.com/blog/inheritance-planning/inheriting-an-ira-from-a-parent/)
Roth 5 Year Rule (https://www.planablewealth.com/blog/retirement/roth-ira-and-roth-401k-5-year-rules/)
RMD Needed when inheriting an IRA flowchart (https://www.planablewealth.com/wp-content/uploads/2021/11/2021_Can-I-Delay-Distributions-From-The-Traditional-IRA-I-Inherited.pdf)
Retired-ish is the retirement podcast for those exploring retirement and those currently in retirement. The retirement ideas and strategies discussed are focused around preparing for one of life's biggest transitions, and how to preserve the wealth that you have worked so hard to achieve!
This educational podcast was created to provide you with confidence in your retirement planning decisions.
Your host, Cameron Valadez, is a CERTIFIED FINANCIAL PLANNER(TM) and partner of financial planning firm for retirees, Planable Wealth.
In each episode, Cameron shares actionable ideas and strategies to help you Simplify Investing, Reduce Taxes, & Grow Your Net Worth, so you can retire on your terms!
Cameron will answer some of the top concerns of retirees including: How can I potentially pay less in taxes to the IRS? How can I better preserve my retirement nest egg and draw a sufficient income? How can I simplify my investments? How can I keep more wealth in the family?
Cameron also takes a deep dive into more complex issues retirees face regarding retirement income, estate planning, Medicare, Social Security and more!
Retirement doesn't have to be a means to an end. To be Retired-ish means to have the CONFIDENCE and FREEDOM to spend your time on what matters most, and retire on your terms! Cameron believes this can be achieved through well-designed financial planning that adapts to life's unknowns.
Find more information about Cameron or ask a question you would like answered on the podcast by visiting retiredishpodcast.com
Want more detailed retirement planning insights? Visit planablewealth.com or join our monthly Retired·ish newsletter here!