Freelance Writing Coach: Recent Episodes
Kaleigh Moore and Emma Siemasko
Kaleigh Moore and Emma Siemasko have long shared a dream: to build the world’s most fulfilling freelance writing businesses. Over the past 6 years, the two friends have become successful freelance writers, finding new clients (hello Salesforce + Vogue Business); refining their service offerings; building six-figure businesses; and ultimately, creating their dream careers.
Now, they’re sharing everything they know and discussing what they’ve yet to find out. Why? Because they know you can build a great freelance writing business, too. But first, you gotta get real.
On Freelance Writing Coach, Kaleigh and Emma discuss all things related to building a successful freelance writing business. Topics include things like client boundaries, digital products, rates, proposals, loneliness, and much more.
Their promise? To tell it like it is.
Did you know we are really good friends? HA. We enjoy each other’s company, love chatting about WHATEVER, and are catching up and giving you a picture of our holistic selves beyond the world of freelance work. We talk about Kaleigh’s history as a dancer, Emma’s weird modern house, and get into what’s happening outside of work. For anyone who wants to get to know us better, listen in on this episode to learn what’s happening outside of work.
This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
Freelance writing is really weird right now. Layoffs, the rise of generative AI, and internal chaos at a lot of companies have made many of us feel super insecure about the field. Our friends and colleagues are kinda freaked out… and maybe we are too? In this episode, we talk about what we’re seeing in the world of freelance writing and what we’re doing about it.
This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
We both work in B2B SaaS. So do A LOT of writers. But what even is B2B SaaS? Why does it seem like so many writers are working in this area? In this episode, we talk about how we got into B2B SaaS, explain why it’s so popular, and offer some guidance on how to figure out whether it’s the right niche for you.
This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
If you’re creating original content, you’ll likely find yourself conducting interviews. You might interview subject matter experts, customers, or your client’s customers! Emma does it all the time when she writes case studies. Kaleigh does it for more journalistic assignments. In this episode, we offer advice on how to conduct a gosh darn good interview that guarantees you’ll get the info you need to do your best writing.
This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
Working with an intense editor can be, well, intense. It has the potential to elevate your writing, poke helpful holes in your sentences, and take you to the next level. But it can also be really annoying. In this episode, we’re discussing our experiences working with editors who’ve got high high high standards.
This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
What does it mean to be a REALLY GOOD writer? In this episode, we’re exploring what content managers, thought leaders, and others look for when they’re hiring writers. In particular, we discuss writing abilities and editorial chops.
WOOOOOOO boy. Where do we start with this one? Unless you’re living on the moon, you have feelings about what generative AI tools mean for your business, livelihood, and craft. In this episode, we explore our thoughts and feelings on AI and offer some ideas on how we can rise to the occasion in the new world of robot writers.
This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
We’ve all had clients that were,,, awful. But what if we told you avoiding nit-picky, cheap, or boundary-crossing clients was well within your control? We believe a screening process makes the difference! Don’t worry– we’ve made our fair share of mistakes, too. In this episode, we’re explaining how we screen prospective clients to avoid bad eggs and maximize good experiences.
This season of Freelance Writing Coach was generously sponsored by Automatic Evergreen (yourweekly.email), B2B Writing Institute (https://b2bwritinginstitute.com/), Growthtrackers (https://supereasydigital.com/growthtrackers), and Ivy Magic (https://thativymagic.com/).
A plethora of new tools are on the market, all claiming to help you write. Are these tools a threat to our livelihoods? Or is it possible that can we use these tools to make our offerings better? Kaleigh and Emma share their experiences with the latest AI tools to help you suss out whether they’re helping or hurting.
Everyone and their mom says they’re a business coach, which might make you wary of hiring someone to help you grow and shape your freelance career. But we’ve both worked as coaches and hired them– we’ve seen the good and the bad and are sharing our experience with freelance writing coaching. This season of Freelance Writing Coach is sponsored by Catch https://catch.co/benefits/health/?r=fwcpod&utm_source=fwc&utm_medium=podcast&utm_campaign=OE
Freelance writing has a ton of benefits, but it’s not for everyone. We’ve known many who’ve decided to hang up their freelance coats and go to a more traditional, full-time job. And many love this trade! In this episode, we share why some freelancers give it up for a regular, full-time job, as well as when you might consider this option. Spoiler: going in-house is not a failure. This season of Freelance Writing Coach is sponsored by Catch https://catch.co/benefits/health/?r=fwcpod&utm_source=fwc&utm_medium=podcast&utm_campaign=OE
Is writer’s block even real? Kaleigh isn’t sure. At least, writer’s block isn’t an excuse to go months and months without writing. But what happens when you’re just uninspired? How can you get the words onto the page and break through… especially when you have looming deadlines? This season of Freelance Writing Coach is sponsored by Catch https://catch.co/benefits/health/?r=fwcpod&utm_source=fwc&utm_medium=podcast&utm_campaign=OE
We had to delay the release of this season due to personal disaster. Unfortunately, these types of disasters are part of life. When you’re battling chronic health conditions, a family emergency, sudden lack of child care, or any other disaster, it can be hard to power through and focus on work. In this episode, we discuss how we navigate these disasters so they have minimal impact on our relationships and careers. This season of Freelance Writing Coach is sponsored by Catch https://catch.co/benefits/health/?r=fwcpod&utm_source=fwc&utm_medium=podcast&utm_campaign=OE
The internet is a weird place full of weird people (can we say that?). While we’ve met many of our closest friends, colleagues, and clients online, we also have encountered our fair share of online bullies, devil’s advocates, and naysayers. As a freelancer, you’re the face of the business, and whatever you say online is fair game to the internet’s trolls. How can you deal with it? This season of Freelance Writing Coach is sponsored by Catch https://catch.co/benefits/health/?r=fwcpod&utm_source=fwc&utm_medium=podcast&utm_campaign=OE
The economic landscape is a little unstable. Rising interest rates, sinking stocks... is this going to affect your freelancing career? Hmm. In this episode, we discuss our perspective on a changing market and share some strategies for recession-proofing your freelance business. This season of Freelance Writing Coach is sponsored by Catch https://catch.co/benefits/health/?r=fwcpod&utm_source=fwc&utm_medium=podcast&utm_campaign=OE
This episode needs a disclaimer which is that we are not lawyers. However, someone told us to get business insurance so we looked into it. In this episode, we discuss business insurance. One of us has it and one of us doesn’t. The person who doesn’t was unlikely convinced by this episode. Basically, talk to an insurance agent. But if you’re looking for a brief overview of what two experienced freelancers know about business insurance, listen in.
Both of us have done our fair share of speaking gigs throughout our freelance careers. Speaking is a great way to share your authority and meet new people. At some point in your business, you may want to start booking speaking gigs so you can share your knowledge with the world. In this episode, we discuss how to start small and what to keep in mind as you embrace speaking. Emma also shares a comedic and bizarre tip for getting people into your talks.
Kaleigh got a new L-shaped desk. Emma’s is vintage. Kaleigh works in an office. Emma works in the corner of her bedroom (thanks California real estate + COVID). In this episode, we’re sharing our freelance desk and office setups. You’re going to hear about a zen-like place and a corner of chaos. By the end of this episode, you’ll want one of our desks and not the other’s… ;-)
WE ARE GETTING REAL ABOUT WHAT WE CHARGE FOR CERTAIN ASSETS. In this episode we share what we think are reasonable rates for blog articles, case studies, websites, and more. We thought we’d be able to share numbers WITHOUT explaining the nuance but couldn’t really do that. There is always nuance when it comes to pricing. If you’re wondering if you’re totally off base with your rates, give this a listen.
Neither of us are LinkedIn masters, but we’ve seen freelancers get massive amounts of value from the platform. In this episode, we discuss how we approach LinkedIn and how we’ve seen others leverage it. We call out Michal Eisikowitz and Leah Neaderthal who are both doing awesome things with the platform. If you’re interested in how freelance writers are using LinkedIn, give this one a listen.
Some freelancers work with one or two longterm clients while others do a series of one-offs. It can depend on the type of work you do, but it can also depend on what you like and what matters to you. In this episode, we discuss the pros and cons of longterm clients, retainers, and one-off projects. There’s no perfect mix, but there’s probably a right(ish) mix for you.
Are your clients texting you in the middle of the night? Do they expect instant responses on Slack? Do they want you to deliver a draft within 24 hours or hop on a call right now? AHHHH. You became a freelancer so you wouldn’t be beholden to a boss, but it feels like your clients are owning you. We know the feeling, and it’s one that can be solved with good boundaries. In this episode, we cover everything client boundaries. We discuss how to create them and uphold them so you can take back control of your business (and your life!).
A listener asked us how we juggle the daily demands of our lives and careers: how do we eat nutritious meals? How do we make sure we get outside every day? How do we make the most of the flexibility that freelancing has to offer? Well, it’s a work in progress for both of us. We’re far from perfect, but we have been freelancing for a long time and have some ideas. In this episode, Emma confesses to just how long she went without renewing her car’s registration.
This episode references the “Wheel of Life” exercise which can be found at this link: https://storiesby.us/wp-content/uploads/2022/04/Wheel-of-Life-Reflection-Exercise-1.pdf
There’s nothing wrong with starting your freelance career on Upwork, Fiverr, or another platform. In fact, we know many successful freelance who did (and still do!) gain a lot from these marketplaces. But what do you lose when you continue to rely on these platforms to get work? Freelancers often tell us they want to get “off platform” but aren’t sure where to start. In this episode, we discuss the pros and cons of these platforms, why it might make sense to get off, and some strategies on how to move away from them.
Both of us write about fairly technical topics we once knew nothing about. But now, we’re experts. In this episode, we talk about our strategies for understanding a topic when we’re out of our league. This will be particularly helpful for those who write about topics they haven’t encountered before.
Some freelancers have a staunch “no negotiation” rule, while others are willing to wiggle on their prices depending on the client and project. In this episode, we discuss our own approaches to negotiation. Warning: neither of us is a good negotiator– we would not get a good deal on a car.
A proposal is a summary of a project plan, something that you and your client can agree upon. Seems simple, right? Proposals can be super helpful for making a sale, but they can also waste a lot of time. In this episode, we go over how to use proposals, available software options, and clever strategies for closing more deals.
Kaleigh has been Tweeting for more than a decade. She’s winning on Twitter with 44,000+ followers. In this episode, she shares how she thinks about Twitter, how she grew her following, and what she thinks other freelance writers can do to get value out of the platform.
Can you really freelance and parent at the same time? With childcare, sure. But what if you don’t have it? In this episode, Emma discusses how parenting has affected her freelance writing career. She goes over maternity leave, the necessity of childcare, and how the COVID-19 pandemic brought more of these issues to light. SPOILER: If Emma has another kid, she’s doing it differently next time.
It’s every freelance writer’s nightmare: a client who doesn’t pay! In this episode, we discuss our experiences with non-paying clients. Should you hire a lawyer, use a collections agency, send a strongly worded email, or just walk away? If you’re trying to track down payment, give this episode a listen.
There are lots of reasons people might want to pick your brain– perhaps they want to get started as a freelance writer themselves or think you’ll have perspective on a particular industry. But if you say “yes” to every request that comes your way, you might waste a looooooot of time. In this episode, we go over how to respond to “pick your brain” requests. When should you say yes, when should you charge, and when should you walk away?
Do you have to introduce a new offering, snag a brand-name client, or revamp your entire business to make more money? NOPE. In this episode, we share 6 simple strategies that have helped us make more money as freelancers. These are achievable strategies that can significantly increase your revenue, especially when sued together. There’s advice in here you can implement today.
Maybe you have one client (or a few) who are dragging you down. They don’t respect your boundaries, aren’t paying you enough, and you’re no longer sure if they’re worth keeping around. In this episode, we discuss how to cope when a sneaky “bad” client makes it in. We talk about preventing scope creep in the first place, knowing when it’s time to say goodbye, and how to part with grace.
Emma loves meetings. Kaleigh hates them. We’ve built different freelance businesses based on our preferences. In this episode, we discuss all our feelings about client meetings, as well as where they should fit into your services.
Social media sites like Twitter, LinkedIn, and Facebook can be powerful ways to connect with your community. But what happens when using these tools has a negative impact on your mental health? In this episode, we discuss how we’ve re-framed our thinking around social media so that it’s not only a better tool for business, but a better tool for ourselves.
“Choose a niche” is one of the most common pieces of advice in the freelancing community. But we’ve seen people flounder when it comes to choosing niches. Why is that? Are niches really necessary?
Other freelancers are not the enemy. In fact, they’re your friends. In this episode, we discuss how we partner and work with other freelancers.
Writing is demanding work, so what happens when you’re giving all your writing energy to your clients? It makes it tough to write a novel, comedy sketch, or op-ed for the local paper. In this episode, we discuss how you can make time for writing side projects.
After many years of success as freelance writers, we still have days where we feel that everyone else has it figured out… and we… don’t. In this episode, we discuss those feelings and how we handle them.
You want to over-deliver for your clients, but you don’t want to provide them with loads of extras that are out of scope. Too much for your clients = not enough time for you. In this episode, we discuss some easy ways to over-deliver for your clients so that they see you as a freelancer who goes above and beyond.
What do you do when you’re overloaded with work? One option is to subcontract that work to other writers. In this episode, we talk about how we came to subcontract, the objections we hear from freelancers considering it, and how we approach sharing the news with our clients (or not).
You’re in control of your own schedule, so it should be easy to take a vacation. But, it’s really not. Why is that!? In this episode, we share our strategies for taking breaks, as well as the challenges along the way. Emma also shares how she approached maternity leave.
Most freelance writers get business because of referrals, but how do you find your people? In this episode, we discuss why building relationships is so important, as well as how to stand out and be memorable.
Did you know that female freelancers make only 84% of what male freelancers do? Ouch. In this episode, we discuss how positions of privilege affect freelance writing businesses, as well as what we can all do to create a more equitable environment.
What do you do if your client tears up a perfectly good draft? In this episode, we discuss how to manage clients so that the revision process is a piece of cake. Our secret? The work comes before we get to revisions.
An efficient business is one that runs like a machine, and it’s dependent on a lot of unsexy stuff, like contracts, accounting software, and templates. In this episode, we discuss the tools and resources we use to make sure we’re not wasting time on the tasks we don’t want to do.
TEN MILLION. Just kidding. Freelance writers can structure their business in a multitude of ways, working with dozens of clients at once or handling one at a time. In this episode, we discuss how many clients is the right number for us, and how we know when we’re working with too many.
When you’re 90 years old and you look back at your life, where is freelancing going to fit in? In this episode, we discuss how freelance writing and self-employment fit into your overall career. This episode is for people who have gone in and out of freelance work, aren’t sure it’s for them, or are midway through their career and can’t figure out how to start.
When you productize a service, you make it easy for your clients to buy a service off the shelf. Productized services may help you sell more, but they may also deter clients from working with you. In this episode, we discuss how to think about adding a productized service to your business.
A portfolio is a curated collection of your best work. In this episode, we talk about what to include in your portfolio, as well as how you should design and format it. We also discuss WHEN to share a portfolio– it might not be at the moment you think.
There are lots of educational resources available to freelance writers. Which ones should you buy? In this episode, we explore whether certifications, courses, and coaches are worth the money and give advice on how to assess whether a program is right for you.
Your freelance writing business is coasting along. How do you take things to the next level? What does it mean to grow? Two not-so-big-picture thinkers discuss how we think about growth and offer suggestions on where to go (grow?) next.
Flaky. Unprofessional. Frustrating. These are some of the words we’ve heard to describe freelance writers. But it doesn’t have to be this way! In this episode, we discuss why companies hate most freelance writers and how you can rise above the rest.
The blank page. Ugh. It’s a source of intimidation and frustration. In this episode, we talk about our processes for getting a piece of writing out the door. We also concluded we don’t want each other’s jobs. Listen in to find out how many words Kaleigh writes in a day.
People say to pick a niche, make a course, and build a website. But we don’t think there’s a right way to run a business. Everyone’s path is unique and different. In this episode, we explore a number of myths about freelance writing businesses and offer alternative perspectives.
Does your freelance website really matter? Kaleigh doesn’t give the website too much credit, while Emma sees hers as a mark of her whole identity. Emma put her head into her hands while recording this episode. If you’re creating a website for the first time, revamping the one you have, or find yourself unsure what a website even means, this is a must-listen.
Guess what? You should probably charge more. But how do you figure out what to charge when there’s not a go-to source for setting freelance writing rates? In this episode, we cover strategies for setting rates, as well as some ways to justify those rates to the clients you serve.
WE ALL WANNA KNOW: How do I find quality, high-paying clients that are a pleasure to work with? In this episode, we cover how we found our first freelance clients, as well as how we find new ones today. It’s a BIG topic, but you’ll come away with ideas on where to start.
Freelance writers have the ability to control our days, but only if we create a structure for guarding our time. In this episode, we discuss what a day looks like in our businesses today, as well as our journey to recognizing what we need to be successful. We also cover strategies on how to deal with clients who want you to be “always on.”
What do you do when you’re a freelance writer in the business of selling you? We discuss why you should approach freelance writing as a very official business. We talk about invoicing software, bank accounts, and recount the moments when we knew we were more than just piddly order takers.
Kaleigh Moore and Emma Siemasko have been friends ever since they started freelance writing almost a decade ago. Now, they’re sharing everything they’ve learned on their brand new podcast. We give quick introductions and explain what the hell we’re doing here.