Rands in Repose: Recent Episodes

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I’m in the midst of a media cleanse. This started before the election when I canceled my Washington Post subscription. Jeff Bezos can do whatever he wants with the Washington Post, and he’s 100% correct that I don’t trust large media organizations.

After the election, I removed all news sources from Feedly except the Atlantic because I find their writing informative and compelling.

A friend calls this turtling. Pulling your head inside your shell and hiding. It’s quite comfortable here. With most of my free time, I’m leveling a dragon Holy Priest in World of Warcraft. #ama

Next on the list is Twitter. Since it was sold and turned private, my engagement has been significantly lower, and my follower count has shrunk as the humans have moved off the platform, but quite soon, I’m deleting my account. My finger has been over the DELETE button for a few days, and I’ve wondered why. Two facts: First, there are thousands of folks with whom I share stuff there. I can see they are there via much reduced but real engagement. Second, I have just under 20k tweets since 2007 that, upon review, tell an interesting story… at least to me.

I’ve downloaded the complete archive, and I’m sad to say I’m about to create a bunch of 404 errors when my corpus of tweets vanishes from Twitter. Why? This is my content, and I don’t want whatever Twitter has become to benefit from its existence. I’ll share the archive here at some point, but for now, I’m cleansing.

Like FaceBook before it, Twitter turned into something else. They both, early on, felt like a means of connection. Unfortunately, building that social graph allowed these businesses to target you and your engaging, clickable content expertly. What was a means of connection turned into hot, juicy, bite-sized content. Over the past two decades, this practice has made us intellectually lazy because these media services are paid not on the quality but the quantity of service. More clicks, more engagement. Truth and facts. Optional.

And what was a clever means of connection turned into a raging stream of clickable things.

So, bye, Twitter. I’m late to the funeral, but better late than never. It was fun before it got terrifying.

While I am profoundly turtling and have little desire to see a path forward, I have two related observations:

First, the lack of healthy debate on most social media is one of the core issues with the platform. Humans must disagree, but these platforms do not provide a proper bi-directional medium (or set of tools) for these debates. It’s liking, then not liking, then yelling, then ALL CAPS, and NOW I’M UNFOLLOWING YOU and YES BLOCKING BYE.

Debate is a tricky act between two humans who can both speak, listen, understand, and possibly evolve. Two humans. Often, there will be more, but let’s keep it simple and assume it’s two. Both humans are required to do this, and in the primarily anonymous world of social media, it’s normal not to consider the other human a human. They are the last thing they wrote that you disagree with. There is no relationship; it’s simply the last thing they posted. And how do you feel about that post.

The stakes are higher in person. You have to stare at that human in the eye, especially after they say something you don’t like. So, what do you do? You can’t yell, you can’t ignore them, and you certainly can’t block them, so what is your move? Mine: seek understanding. Put on that empathy hat and try to understand why they’re saying what they’re saying. That’s the first step. There are many more — read the book.

The continual failure to do this in social media results in a growing echo chamber where the humans agree, and those who disagree are quickly voted off the island. Some of these echo chambers are low stakes. Think about your favorite sports team. Those fans are aligned on what’s important. Who needs debate? The only debate we care about is what $OTHER-TEAM we hate the most. Go $OUR-TEAM.

There are higher-stakes echo chambers, too. Use your imagination here.

Second, it’s not a short or medium-turn fix to what ails us, but I am curious about investing in local and independent news organizations. Large media organizations have to compete with social. They desperately need those clicks, and that means mimicking the patterns they see in social. The headline must engage in one second or less, or it will be forgotten. It’s an economy of attention, not understanding or truth.

Local media has taken it on the chin for decades because social media consumes advertising dollars. Local media has withered without that support, with remaining big media sources bending to social media engagement patterns. The idea of investing in local media news organizations is because they report on the events that happen in my neighborhood. This makes them more human to me. They have skin in the game because, like me, they live here. My problems are their problems, which means we have a solid foundation to start to understand.

How do I go about this investment? Where do I start?

I don’t know. I’m turtling. For now.

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In our 85th episode, we talk dapper and how it might be armor.

Enjoy it now, or download for later. Here’s a handy feed or subscribe via Overcast or iTunes.

https://traffic.libsyn.com/rands/theimportantthing0085.mp3

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Hi. I’m stressed, too. Here are random thoughts on this from the beginning of November 5th, 2024 — election day:

  • Today, a convicted felon and failed businessman (six bankruptcies!) slash narcissist slash twice impeached politician who does not believe in democracy, who called for and achieved an armed insurrection, and who lies compulsively is the Republican nominee for the President of the United States.
  • While the presidency is at stake today, winning the presidency is only part of what is decided tomorrow. There are countless House and State elections, State Supreme Court, and other Statewide offices on the line tomorrow, which leads me to a strangely comforting thought…
  • There’s no scenario when it’s “over” later today. Whoever wins will face a passionate, well-funded, and motivated opposition who will spend the next four years attempting to win back what they lost.

Hmmm. This is just stressing me out more. Let’s try something different.

That’s CuriousIf you ride a Waymo, they’ll flip you off.

Waymo is an autonomous vehicle available in San Francisco. No driver. All robots. I’ve taken ten rides so far, and it’s a coin flip if someone gives me the finger. There’s the folks on the street. Other drivers. Really, anyone might flip you off.

That’s curious.

With no judgment and pure curiosity, I suspect the reasons for the middle finger might include the following:

  • Anger with a service that will make a bunch of jobs irrelevant.
  • Abstract anger with the general idea of artificial intelligence and what it might present to the human race.
  • Fear. Pure fear of the unknown. We, as a species, have an impressive history of doing incredibly stupid shit because we’re scared.

Fear is natural. It’s equal parts rationality and irrationality. Shoved together instantly when you are quickly presented with a suddenly unfamiliar situation. It’s your brain flipping the high alert switch because you don’t know what to expect next, and the stakes appear high.

So you react. Fight or flight.

And then you flip off the robot car.

Cool.

There’s another emotion you can experience in a car, and that’s road rage. This is the moment you’re behind the wheel, and another driver cuts you off. In a second, you go from calmly driving down the highway to a vicious, rageful human bent on the destruction of this other.

In an instant.

That’s curious.

With no judgment and pure curiosity, I suspect the reasons for the rage might include the following:

  • Surprise, your calm drive to work was suddenly interrupted.
  • Anger at this anonymous whoever interrupted your calm drive to work and threatened your safety.
  • Finally, and full disclosure on this one, I did research here; you’re probably male and either already stressed about something else and/or have higher levels of impulsiveness and aggression on the road.

Understanding that, as a human being, you can have these real and immediate visceral reactions is essential because these reactions are being exploited daily1.

On CuriosityI mostly ignored the mid-terms. I ignored it because most of the content generated that cycle wasn’t news; it was carefully constructed incendiary entertainment posing as news designed to get me to flip off someone. It was not designed to inform but to get me to react. Quickly and emotionally. No reason. Fight or flight. I chose flight.

This political season, I’ve been all in. Since last November, I have completed one small act each day. This can be a donation, or this can be an action like writing and editing this piece. At the outset, I had a blank slate regarding what I knew. I spent a lot of time understanding how political payment processing works. I built a remedial understanding of the critical issues in each swing state and read about the intricacies of voter suppression. Curiosity is a feedback loop. The more I learn, the more I can inform and target my actions. It’s delicious. Information is empowering.

And calming.

Elections have been gamified. The stories from major media outlets are designed to get you to engage and not to think. In fact, they’d much prefer if you forwarded that link with that clever headline to all your friends… who cares if you read it? We need the clicks. We need that sweet advertising revenue.

Campaigns run the same playbook, but they don’t need your clicks; they need your money, and that means they must convince you, scare you, and motivate you with an artisanally crafted crisis tailored to get you not to think but to flip off the robot car and then donate as frequently as possible.

The Big LieThe only vaccination I know to the incessant barrage of memes, rage, and compelling lies is education. One of my daily acts has been educating myself. When someone makes a bold claim on the news or social media, I take the time to understand what they are saying and the history behind it. Many of these research adventures have led me to the darkest chapters of United States history, where I’ve learned that this group of oppositional humans has always existed. Its election deniers in 2024; in 1865, after losing the Civil War, unrepentant Confederates were sent to Washington as senators and representatives.

Congress refused to seat them and drafted part of the 14th Amendment “to perpetuate, as a constitutional imperative, that any who violate their oath to the Constitution are to be barred from public office.”

I didn’t know that. Now I do. We both do.

The biggest lie they propagate is devious and deflating. It’s the idea, the feeling, that there are many — more of them than you. They do this by being loud and outrageous, minimizing those they consider less. They want you to think they are legion because they know they are less. There are more of us than them. Not Democrats or Republics, but decent, kind, and thoughtful humans. I’m talking about people who want the best for others and are willing to do the work to help each other.

So, today. Vote, then stop watching the feeds. Turn off the TV, which is more entertainment than news. Don’t worry. The results will find their way to you. I guarantee it. While it does, take time to teach yourself something. Go deep. Call someone you know is stressed and ask them how they are doing. They’ll laugh nervously. That laughter, that’s stress transforming into relief. You helped. Briefly. Call another person? Sure. Do 15 minutes of your favorite exercise. Even better. Your brain does its best work when it’s working out; today, you need your best work. Tomorrow, too.

There’s no scenario when it’s “over” later today. Whoever wins will face a passionate, well-funded, and motivated opposition who will spend the next four years attempting to win back what they lost.

But there are more of us than them.

Now breathe.


  1. Oh, Waymo? They delivered absolute magic. Try it. It will exceed your expectations and give you a glimpse into a possible future where serious crashes are significantly reduced because 94% are caused by human error. There will be unforeseen consequences, upsides, and downsides, but as a super fan of progress, Waymo is on a short list of moments I know I’ve seen a compelling future. ↩

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  • Less than 1% of your writing will be life-changing.
  • 3% will be trivial to write.
  • 4% will strongly resonate with others in a way you didn’t expect.
  • 5% will be quite good.
  • 15% probably should’ve never been published.
  • 26% will elicit a reaction you did not expect. Positive or negative.
  • 28% will become vastly better because you chose to edit.
  • 30% will start as one piece but finish as another.
  • 40% will be good solid writing.
  • 45% will do much worse than you expect when published.
  • 60% of your writing will never be finished. Be ok with that.
  • 100% of your writing is worth your time. 1

  1. Thanks to the folks at the Rands Leadership Slack for reviewing an early version of this piece. ↩

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Good, me too.

Over on the Rands Leaders Slack, we are almost thirty-four thousand. Fun fact: in the 2020 Presidential Election, three battleground states, Arizona, Georgia, and Wisconsin, the margin of victory was less than 30,000. In Georgia, President Biden won by just over 12,000 votes.

It makes you think.

It’s an, uh, interesting time in United States politics. If you happen to live in the United States, I enthusiastically encourage you to firm up your voting plan. Check your registration, figure out how and when you’ll vote, do your research, be a leader, and show them how it’s done.

https://www.vote.org/ can help with all of this. Click on that link. Thanks.

If you’d like to take more daily action, join the Rands Leadership Slack, send me a DM that you’ve got a voting plan, and I’ll explain how you can get your hands on a couple of Rands stickers.

Happy democracy.

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In the early days of this weblog, I was on MediaTemple using MoveableType for a good long time. Three things happened during these many years:

  1. MoveableType was mostly abandoned during this time. I’m sure well-intentioned folks were working on it (and it appears they still are), but the vibrancy of development had faded from my perspective at the time.
  2. MediaTemple (now GoDaddy) was similarly abandoned. They were happy to take my money, but the level of service had a marked decrease by the simple measure of the amount of time from when I asked a question about the service to when I felt the question was sufficiently answered.
  3. I became increasingly busy. The amount of time I could devote to the care and feeding of the site and hosting significantly decreased. While this made me sad as I have a deep desire to understand how things work, if I was devoting time to the site, it was writing.

Late in my tenure on MediaTemple, a good friend and noted WordPress enthusiast, Alex King, volunteered to move the site to WordPress. At the time, I was concerned about performance with a dynamically generated site — WordPress had an unclear performance reputation — but Alex convinced me. We agreed on a new design and moved to WordPress, and everything was fine. It was instantly obvious that WordPress had a vibrant development community, with the core software constantly being updated, unlike MoveableType. Publishing platform. Solved.

MediaTemple was the next issue. Without warning, MediaTemple shut down my site because the now unused MoveableType site had been hacked in a manner I still don’t understand. No warning, and they blocked my access so that I couldn’t debug the issue. Worse, the only way to unlock the site was to pay MediaTemple money for a site cleansing, which I eventually did, during which they found nothing.

I started looking for a new service provider, and WP Engine showed up as a credible vendor after I spoke with WordPress knowledgable humans. I don’t remember what I was paying for MediaTemple, but WP Engine felt like quite a bit more. I went back and forth with myself and finally decided, “I am willing to pay for good service so I can just write.”

I vividly remember the migration to WP Engine not because it was flawless, but because when I had issues, I pinged WP Engine tech support, and they responded almost instantly and competently and the chat was not over until I told them that we’d resolved the issue1. This professional, high-quality tech support level has remained unchanged for many years, and I’ve remained on WP Engine.

Since my move to WP Engine:

  • I can’t recall a single outage. I have been sitting here staring out the window of this train for twenty minutes and can’t recall a single outage.
  • I’ve added several new paid services to my account.
  • I am mostly unaware of what is going on with maintaining my site. I upgrade WordPress and plugins when upgrades are available, but mostly I write and publish content, which is — ya’know — where I want to spend my time.

WP Engine. Not cheap. I don’t care. As a lifelong user of online services, I have a hard-earned and well-defined rubric regarding what I’ll pay, which reads, “I will pay a premium if you are doing what you say you are going to do — all the time.”

I can’t comment on the WordPress v. WP Engine kerfuffle. It seems like a long time coming; it is super complex and increasingly heated. Drama usually means profound misunderstanding.

I can confidently say:

  1. I appreciate the hard work of many humans who invest unfathomable hours into WordPress and the vibrant WordPress plugin ecosystem. I eagerly pay for many of these services.
  2. WP Engine provides a valuable and essential service, delivering WordPress to me and my readers, for which I also happily pay. I pay for many online services and would rank WP Engine’s quality, reliability, and support in the top 10%.

As an eager user of the software and the services, I hope they’ll find a fair and symbiotic resolution.


  1. One issue I had during migration was that WP Engine did not allow a few plug-ins that I was using on MediaTemple. One was an old link checker that would go through old posts and find old links. WP Engine’s justification for disablement was, “This is resource intensive,” which made sense at the time. ↩

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I was doing this talk, which I’d done dozens of times before. Good, well-practiced deck. I was speaking to CTO-types (current and aspirational) as a favor to a friend. This was a monthly morning coffee chat for this crew, and they invited folks like me to speak. It was on a weekday morning near Slack in downtown San Francisco.

No problem.

Practiced talk, small group, low stakes. I was editing the title slide to update the location and name of the event. No practice necessary; again, I’d done it before.

The piece was based on this piece called Stables and Volatiles. The brief pitch. Stables are those who happily work with direction and appreciate that there appears to be a plan and the calm predictability of a well-defined schedule. Volatiles are the opposite. Read the piece; I like it.

Finished quickly. I was told this was more about a discussion than a presentation. Fine with me. Q&A tells me precisely how well the deck landed, and I’d done this talk enough to believe the Q&A would be rich. Healthy banter. It started that way. Questions about my first stint at Apple and whether well-known people were Stables or Volatiles, but then Leo in the Back Row lost his shit.

“This is bullshit. It’s a false dichotomy.” Leo, the CTO in the Back Row, was pissed about my presentation. For those without ChatGPT at the ready, a false dichotomy is “the fallacy of presenting only two choices, outcomes, or sides to an argument as the only possibilities, when more are available.”

After some back and forth, I told Leo, the CTO in the Back Row, that, like most of my writing, I liked to describe humans in stark, clever ways. This often took the form of a “THIS or THAT” black-and-white structure, but I was 100% clear that the answer to humans was a hard-to-define grey area. My job was to get you to think, not to define every possible configuration of human behavior.

I’d delivered that answer before, and it worked, but Leo, the CTO in the Back Row, was having none of it. He was still angry and — now, I am guessing — because I’d wasted his time. He was promised a structured model, and I delivered confusing poetry.

Leo, the CTO in the Back Row, was the Police. And the Police don’t like poetry.

Guess What, LeoI have another false dichotomy for you: the Poets and Police.

Poets:

  • Finish things. Usually.
  • Use rich language to describe abstract situations.
  • Believe well-formed, highly descriptive ideas make the world an understandable place.
  • Are fine with ambiguity because they understand it’s all just shades of grey.
  • Fall in love with ideas. They’ll fall in love with a single choice word.
  • Like to use the word “feel” because feelings are distilled intuition expressing themselves as inspiration.
  • Love thoughtful compliments.

Police:

  • Finish things. Wow, they finish things.
  • Crave well-defined structure and rules.
  • Believe rules make the world an understandable and measurable place.
  • Hate ambiguity because it provides no direction.
  • Deeply enjoy both debating and enforcing those rules. They believe this is how you make future measurable progress.
  • Will debate a single word that is out of place until clarity is achieved. (Poets do this, too.)
  • Are excellent at measuring anything with metrics. Are unlikely to believe unmeasurable truth.
  • Never use the word “feel” because feelings are irrelevant to getting the job done.
  • Appreciated well-defined accomplishment.

Two things.

First, as a Poet, I know I am describing the Police from my perspective. Police will profoundly disagree with many of the attributes I describe. I am eagerly listening.

Second, yes, this article is similar to my much earlier piece on Organics and Mechanics, but I feel it’s stronger writing.

Third, I am making up a third thing. To annoy the Police who were keeping count because that is how we Poets roll.

Success is BothAs a self-declared Poet, I can confidently describe the Police because it is a job requirement that develops strong working relationships with these essential humans. I need them because the Police do the challenging work of keeping the trains on time. This isn’t simply holding conductors to a schedule but also maintaining the trains, taking care of the track, and ensuring we have a qualified staff of humans to do all this work. Oh, and how about a budget? How are we going to afford all of this? Someone needs to build a credible business plan for this train company so we can afford to keep the trains on time.

As a self-declared Poet, we also need to understand the aspirational goals of this train company. I also understand the importance of consistently sharing this vision with everyone. I know we need to listen because we need to understand how the company feels. I’m adept at organizing teams of humans with differing ideas and skills. It’s an endless puzzle that I enjoy attempting to solve. I love celebrating our victories. I feel our failures deeply, but I know that with the Police, we will learn from these failures.

Listen. Leo. The CTO. You there — in the back row. I get why you’re mad. See, while we differ in how we view the work, we are the same regarding what’s essential. We want the team to succeed, and we want them to advance. I’ve learned some of my favorite moves watching you work, Leo. I’ll work hard to try not to waste your time with too much poetry if you work hard to understand that poetry is part of how we describe and achieve the impossible.

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I’ve worked at three successful start-ups and one failure. I’ve also worked at post-IPO successes such as Borland, Netscape, and Apple, which means I’ve seen a lot of different founders who, if you measure success financially, were quite successful.

My backstory aside and with deep respect, most founders fail. You’ve heard of the stories of sucessful founder because they’ve become famous (or infamous). However, the majority of start-ups fail. No one tells and retells the stories of these companies because they never launch. No one became rich or famous. It is their defining characteristic. In his recent essay, Paul Graham talks about the successful founders. However, it’s not “Founder Mode,” it’s “Successful Founder Mode.” Lumping all Founders together would mean we should — statistically and more descriptively — call this “Failing Founder Mode,” which is neither clever nor inspirational.

As a person deeply in love with naming things, I like the framing of Founder and Manager Mode because it’s clever and instantly useful. If you’ve been reading me over the years, you’ve noted I’ve begun to detest the term manager for some of the reasons Graham highlights: unfamiliar with the details, management at a distance, lousy hiring, and siloed decision-making. I’ve gravitated towards the word leader both because I want to make it clear any motivated human can execute the skills of a good manager — leadership comes from everywhere — and, more importantly, I believe managers tell you where you are. Leaders tell you where you are going. It’s a philosophy thing.

It’s less clever and symmetric, but I would define these two modes as: “Founder Mode” and “Scale Mode” because one of the many things you need to do as a successful start-up is scale. Landing managers is one of those tactics, but it’s just one essential investment you make as you scale. Other tactics are equally important. Focusing on managers as the thing that makes you a larger successful company gets you… more managers. Gross.

My observation from three successful start-ups, three post-IPO starts where the founders still ran the show, and one failure: the founders were all eccentric humans. In a hypothetical room full of humans, which included these founders, you would eventually notice their behavior or conversational pattern. You would single them out in your head because the hair on the back of your neck stood up and wonder, “What… is going on there?” My one start-up failure? The founders? By the book, MBA types. Standard vanilla leadership. Trust me, you’ve never heard of them or the start-up.

Graham hints at some of the attributes of Founder Mode but mostly says it’s not a well-defined. It is. Founder Mode is the culture of a company and a culture is defined by the character of the founders. Here are the values I’ve discovered over and over again working with these humans:

  • The whole team is involved in the details. Anyone can argue about the product because everyone works to be a product expert.
  • Everyone does the work. The stratification of responsibility is a red flag not just in rapidly growing team, but any company. Everyone files bugs because everyone uses the product. Yes, there is job specialization, but there is also a belief that we are equally accountable for the product.
  • An organization chart doesn’t tell you who can speak with whom; it tells you who is accountable for what. It’s a map. Not a power structure.

And finally, hire leaders, not managers.

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In our 84th episode, we go deep on the idea of why it’s bad to be busy.

Enjoy it now, or download for later. Here’s a handy feed or subscribe via Overcast or iTunes.

https://traffic.libsyn.com/rands/theimportantthing0084.mp3

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Awkward.

Seven of us now. Sitting around the table. Five minutes since the start of the meeting. We’ve used up our chit-chat allowance and wonder if you will show.

In the scheme of things relevant to a company’s success, showing up late to a meeting is not the end of the world. When it happens a lot, when it’s always the same person and that human is a leader, I have a severe tick when it comes to this human. Here is my chain of increasingly frustrated and snarky reasoning:

Here’s my inner dialog:

  • Do you know that you are late?
  • Do you understand why you are consistently late?
  • Do you understand the total cost of this lateness? It’s the room full of humans waiting for you, plus the repeat of the information they’ll need to hear when you arrive.
  • Do you understand the subjectively immeasurable credibility hit you take each time this happens?

With that out of my system, let’s get to the heart of my concern. If you understand the problem and further understand the cost of this behavior, why is it continually happening?

Many meetings are predictable. Look at your calendar first thing in the morning. Is this an achievable set of work? No double bookings. Good. Do you see where you are likely going to be time-constrained? You’ve got a meeting you must attend that always runs long — ok, move the meeting after it. You’ve got one meeting on the opposite side of the campus? Ok, build in travel time and adjust the calendar as necessary.

Some meetings are not. Day has started, and the universe is throwing you curveballs. It happens. A reliably stable meeting ran long. Did you tell the next meeting to move on without you? Wait, you need to be there? Ok, move to the next available slot — quickly and alert attendees. Loudly. An important meeting landed in the middle of your everything? Ok, what needs to shift? Shift it. Loudly and promptly.

But it just keeps happening. Five minutes late to everything. Too much on the calendar, too many curveballs. You are in a constant state of stress, and this is where I will stop us for a second to state the obvious.

There are leadership types who believe this level of busy is correct. They believe a key part of the job is this level of stress and scurrying hither and fro. Some humans find a modicum of pride in this state. You know, the meeting doesn’t start… without me.

To all the serial show-up-laters who meet this criteria,

You are a failing leader.

Strong words. You thought your consistent five minutes late was a quirk. A minor operational error, but in my book, it’s a strategic flaw because you are not identifying and fixing the fundamentals. There are so many minutes in a day, there are only so many meetings you can personally attend, and these are knowable quantities. Failure to address these fundamentals means you are not growing as a leader.

Who can go instead of you? No one? Why? What is so essential about you? Experience? Really? How does one gain experience? You give others the same opportunity that someone else gave you. You ask them, “Can you attend this review?” They look panicked, so you tell them, “Here is the essential context you need. These three things will likely happen; here’s what I do when they occur.” They look less panicked, and you finish with, “I know you can do this.” They grin. Nervously.

Delegation. This is one solution. There are many more, but I’m not listing them because it is your job as a leader to identify the problem that ails your team and be accountable for properly and permanently fixing them.

So you can show up for a meeting on time.

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You’re not going with that title, are you?

I might.

There are no actual trophies or awards.

Correct. There are three Rands Useful App Awards this year, but before I award them, I will define the criteria I used to select these products.

  1. The application has substance. This is not a one-shot utility that does one thing well; the designers and developers have built an application, a service with deliberate weight. There is a richness in functionality and depth. This is because…
  2. The application effortlessly provides domain expertise. The humans who built this application care deeply about the domain for which this product was built. After you know the application, you think, “Gosh, I wish it does X.” It does X. It does Y. And it doesn’t do Z because you don’t need Z — what you need is Z++, and when you discover that, the application becomes indispensable because…
  3. Each of these products integrates many different data sources. This is not obvious to the end user because the designers and engineers have to great lengths to make this integration seamless and allow users to move between views of data effortlessly.
  4. A by-product of deep domain expertise is quality. A motivation to deliver a high-quality application or service can be created in many ways, but well-defined motivation comes from experts. The humans who understand the problem space and these humans will go the extra mile to ensure the product is built correctly and works as expected. They also…
  5. Obsess about every detail. Obsess? Too strong a word. Design, for design’s sake, makes the product approachable and perhaps more usable. Design motivated by deep domain knowledge gives each decision defensible meaning. When users encounter these design decisions, they think, “Uh, this product just read my mind. That’s amazing.”
  6. Finally, the product has voice. It has an opinion about what it is. This is the hardest attribute to define (and build) but the easiest to observe. When you fire up the product on your phone or web browser, the product has something to say.

With these attributes in mind, I give you the 2024 Rands Useful App Awards.

Really? Sticking with this whole bit? Ok.

Windy For the past two years, during the rainy season, I’ve been sending out an update to a Messages group composed of my Dad’s group. The point: give folks a heads regarding rain for the following week. A hyper-local forecast based on a handful of data sources. At the core of that forecast is Windy.

Weather nerds build Windy. Click on that link and observe the vast array of weather-related resources at your fingertips. Unlike WatchDuty, you’re on your own in terms of getting answers to your weather-related questions, but the answers are there in terms of wind, rain, temperature, cloud cover, waves, thunderstorms, air quality… and those are just the layers I can see in my current configuration. There are dozens more.

I augment my local forecasts with other sources besides Windy (Weather Underground is particularly accurate in my region), but Windy is where I start because Windy has a weather answer for everything.

WatchDuty WatchDuty provides a rich real-time map of nearby wildfires and firefighting efforts. This is probably less immediately interesting to you if you live somewhere with less combustible dry fuel, but we’re all going to care about this more over the next couple of decades.

Pre-WatchDuty, when a fire flares up nearby, you’ll spend hours discovering the following:

  • Major news networks are slow and lack detail,
  • Social networks are full of noise, and,
  • There is a dizzying amount of structured data regarding any fire in the form of maps, satellite imagery, weather forecasts, and other tools.

WatchDuty meets all the Rands Criteria. I check the fire situation in California a couple of times a week, and — at a glance — I can quickly see hot spots in the state. It quickly conveys location, size, containment, and recent news updates. Also, seeing the real-time status of all aircraft involved in the fire is fascinating. These updates are the core of WatchDuty and are supplied by a curated set of reporters who are sifting through all the noises to find the best and freshest signal.

Flighty A recent addition to a familiar problem. Everything works when you’re flying except when it doesn’t. Complex systems fail complexly, and when they do, the difference between spending a night at a crap hotel in O’Hare and making the next flight to Newark is timely information.

Flighty will not rebook your flight to Newark, but Flighty will give you every opportunity to become aware of emerging complex disasters. The application crushes all the criteria listed above, but the outstanding aspect is, “These designers and developers fly. They fly a lot.” This is best demonstrated by the Flighy Passport, which clearly shows all your past flights, total number of miles, flight days, airports, and airlines. How do they know this? Because, of course, you put all your itineraries in TripIt, right? Of course you do.

The immense amount of pertinent travel information built into Flighty is staggering, but if you haven’t obsessively kept track of your travel for years, just put in the flight number of your next flight and see what Flighty can teach you.

A Function of FocusI originally called these the Rands Indie Awards, and while each of the applications is some form of independent, I think the larger observation is they aren’t a product of a large company. Flighty looks like it’s three humans. Windy is owned by a billionaire but appears to be less than twenty developers. WatchDuty is a not-for-profit and appears to have less than twenty full-time humans.

Why is the size of the team important? The size of the team directly correlates to how well they can focus. For each of these products, it’s clear they picked a domain or a problem space they deeply understood, and with a small set of hands, they focused on building a substantive, high-quality product with voice.

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  1. Say their name if you think they aren’t listening. In a meeting with five or more humans, it’s ok if someone checks out of part of the conversation. Not every topic is of equal interest to all humans. When you know the conversation is steering back to a human who isn’t listening, say their name.
  2. Repeat the hard part when you don’t understand. Or, repeat the last thing they said and add a question mark. Ask questions if you don’t understand.
  3. Pause if you need more time to think. Let the conversation breathe.
  4. Move your line of sight below theirs. Hunch over a bit. This changes the sense of who is in charge of the conversation. I learned this subtle move from a fascinating book about improv. We, as humans, react to the relative position of another’s gaze. Higher, they are driving. Lower, they are receiving.
  5. Look them in the eye if you think your point isn’t landing. Or if it’s important to them. Repeat the point. Once. A variant of saying their name, except in this scenario, you have their attention, but it’s unclear if they understand the point.
  6. Stop talking. Ask them what they think. Or slow your cadence. I get on a roll often, conversationally, and what feels like a delicious conversational tale to me is rambling. When the room starts to tell me this, I stop. I stop for five seconds. In five seconds, you can effectively reset the tempo of a conversation. Possibly my favorite conversational move. s
  7. Listen to the room when you are done to see and hear what they heard. Does the conversation continue immediately on the same or related topic? Excellent. Is there a painful, long silence where it’s clear you didn’t deliver your message? Keep trying.

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There are two classes of songs I listen to when writing. Words and no words. Word songs are used when I the writing does not require flow — deep thought. The problem with words is they get in your head, bump around, and start creating more words. At a time when I am attempting to focus on a specific set of words, word songs are not the solution.

Nonword songs have no words and are deployed to encourage the correct words. The lack of work but the presence of melodic feeling (plus one to three cups of coffee) is the perfect partner for new word writing.

Since the release of Spike Jones Her in 2013, the perfect reigning champion of non-word songs continues to be Dimensions by Arcade Fire or Owen Pallett> — it’s unclear who wrote it1

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In our 83rd episode, we revisit the various use cases we’ve discovered with our favorite AI tools.

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Second year of UCSC. Decades ago. A predilection for Domino’s Pizza and a fundamental misunderstanding of how credit cards worked left me in a financial hole. I needed a job, any job, and the School of Social Sciences offered a job aligned with my computer science degree, lab technician.

A solid interview with a prompt job offer. This is going to be easy.

No, this is going to be boring.

The lab technician role was among the lowest rungs on the Social Science ladder. My boss was a tenured professor who was somehow protecting grant money by hiring a minimum-wage lab technician. Her description of the role during the interview versus what she described on my first day had little intersection.

“Make sure the lab is tidy. Make sure the terminals work. And whatever else you want to do. You have a storage room where we store old terminals and other random hardware. You have an office. It used to be Crazy Charlie’s. It’s a mess.”

The lab was a large basement full of rectangular tables, each with two terminals on top. I never saw a human use the lab in my first two weeks on the job. The pre-PC terminals were heavy and ugly. A quick assessment revealed that 50% of them refused to turn on.

And that was the good news.

The storage room was long, perhaps twenty-five feet deep, with ceiling-high racks on both sides. These racks were jam-packed with discarded terminals, cardboard boxes full of who knows what, random bits and bobs of technology, and then just random crap. I could get halfway to the back of the room before being stopped by overwhelming clutter. My assessment: random humans had been leaving and piling random crap in this room for a decade.

And that wasn’t the worst news.

My “office” made the storage room look tidy. The prior occupant, described to me by multiple people as “Crazy Charlie,” had apparently been a hoarder, and this office, roughly half the size of the computer storage room, featured a stunningly diverse set of detritus. If I squinted, I could see a desk somewhere under all that junk, but I couldn’t see the back of the office nor much of the side walls. The ceiling appeared intact.

There was no guidance on what to do with the office and storage room. Just the basic “keep the lab tidy” guidance and nothing more. Part-time gig. Twenty hours a week if I wanted. 10 hours required. While she did not say this, I felt my boss knew I was a college student; this was a college job, and she was giving me permission to phone it in.

Keep the lab tidy.

Boring.

Two TreasuresIt was January. The gig lasted through the school year. The first week, I did what was asked of me. I kept the lab tidy, which meant I spent an hour shuffling around the lab and confirming that the working terminals worked. For the non-functional terminals, I tinkered. Flipping switches on the back of the devices meaninglessly. Oh, look. Now it works. I wonder why. Twice, I went into the storage room to assess the chaos. Twice, I left after five minutes, feeling overwhelmed.

The second week, I did even less tidying. I’d discovered MTrek, and since no one seemed to care, I played MTrek on the terminal. No one noticed because no one was there. As the week came to a close, it was clear:

  • No one was expecting anything out of this gig.
  • No one cared how I spent my time.
  • No one cared if I did nothing.

But I do.

The weekend after the second week, I arrived at the basement of the Social Sciences building at 6am and emptied the contents of the storage room into the hallway. If you were walking through this hallway at the time, you would assume a nerd junkyard had exploded.

My goal with this strategy was to get a sense of everything collected in this space. The categories ended up being:

  • Garbage to be thrown away immediately. No obvious value. This was 40% of the crap.
  • Terminals. Lots of terminals from many years. The functioning ones were kept, and the others were flagged for recycling. Note: I had no idea if recycling was an option, but filling the garbage bin outside the building with dead terminals seemed bad.
  • Documentation. This was the first treasure. Someone had deliberately organized documentation for the terminals. They’d collected this documentation and labeled the front of manuals to clarify which documents described which terminals. Suddenly, the lab wasn’t full of random crap, but terminals I now understood how to manage.
  • Esoteric hardware. The deeper I went into the storage room, the more random, interesting hardware I discovered. There was a punch card computer complete with punch cards. There were odd measurement devices. From their placement and how they’d been stored, it was clear these machines had been placed here for safekeeping.
  • Knick knacks. Someone had kept a collection of Coke bottles. Like the esoteric hardware, these bottles were here for a reason that I would never understand but could tell existed.

With the hallway strewn with my discoveries, I performed a deep clean of the storage room and then moved saved items back into the room, keeping a handwritten log of each item and, if applicable, a count. Working terminals were labeled as such, non-working, too. Documentation was sorted and placed in a filing cabinet. Esoteric hardware and knick-knacks were carefully placed as before — in a quiet, dark place of honor.

I finished the storage room purge late on Saturday night. It is a truth you can’t fully appreciate a deep clean until you’ve had time to forget the work involved in cleaning it, but this room was now blissfully clean and orderly. I could walk from front to back easily. I could sense the stored terminals were placed deliberately — there was a sense of the system. And the knick-knacks, the strange hardware, gave this room no one cared about a sense of playful mystery.

I originally planned to spend a few hours in the storage room that weekend. I spent 10. As I went to sleep in my dorm, smelling of dust and sweat, I stared at the ceiling and decided to finish the job correctly.

The OfficeThe garbage factor in Crazy Charlie’s office was twice the amount in the storage room. At some point, someone had decided to use this office as a place to put garbage that somehow wasn’t garbage yet.

Dozens of trips to the garbage bins outside of the building. After I filled one, I walked around the building until I could find another. Unlike the storage room, there were few clusters of interesting items. Some terminals revealed themselves, as well as additional documentation, but mostly, garbage.

Once I reached the back of the room, I discovered the second treasure. Someone, sometime, had built a set of French windows on the room’s back wall. The windows opened… to a blank concrete wall. Against that wall, inside the windows, there sat an empty leather satchel1.

Crazy Charlie, I assumed, had built French windows in his dark basement office. A window to nowhere. Perhaps this is why they called him Crazy Charlie?

You Know What’s Crazy?Calling people crazy. It’s ignorant. It’s cruel. It minimizes humans rather than supports them. It demonstrates a profound absence of empathy.

In my weekend of purging the storage room and the office, I’m sure I was wandering around a small, interesting part of Charlie’s mind. Someone who was trying to preserve the knowledge about these terminals by saving and organizing this documentation, someone who was keeping interesting hardware, someone who liked Coke bottles, and someone who wanted a view.

You know what else is crazy? Wasting your time. The reason, decades later, I frequently think of this unpaid weekend adventure sifting through a year of garbage, hardware, and knick-knacks is because it is when I discovered the compounding non-obvious value from doing exceptional work.

No one saw the tidy office or the storage room for weeks because they’d given up on those spaces. It wasn’t until Week #4 when my boss brought her flaky terminal to the lab and asked for help. I walked her into the pristine storage room, pulled a working terminal off the shelf (there were four), and told her what switches she’d need to flip to get it to work on our network.

“What happened here?” she asked.

“I cleaned it up.”

Week #6. Her boss walks into my office, which is now a proper office with two desks (one for my computer) and the second for repairs. He asks, “I’d love it if you could walk me through how you organized your terminal closet. We have one on the third floor that needs help.”

I grabbed the red binder, which had the up-to-date inventories of the lab, closet, and office, dropped it on the desk, and asked, “How can I help?”

Week #10. The head of the IT department for Computer Science walked into my office, looked around, grinned, and said, “So. You’re the guy.”

Charlie’s WindowThe Computer Science department offered me a gig the following year running all of the labs in their main building, but I’d already decided on a part-time gig at Symantec, which turned into a full-time role that turned into a career.

During my junior year, I ran into my Boss walking across campus, who told me, “You know that punch card computer you found in the supply closet? It was only one of the three built and the only one remaining. It belongs in a museum.”

Week #3. I sat in my tidy office, spinning in my chair, staring at the empty French window frame and wondering why Charlie had built it. Inspired? Sad? What’s the back story? Part of me wanted to ask my boss about his backstory, but I never did. What I did was buy a poster of Yosemite’s Half Dome. I carefully cropped the poster and placed it behind the window.

A proper view from a dark place.

And a job well done.


  1. The empty leather satchel. Yeah, it’s still a total mystery. ↩

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Prologue. Westworld was an HBO reboot of the 1973 Michael Crichton movie. The pitch: we’ve built vast amusement parks populated with ultra-realistic robots (called “hosts”) who act their parts within the park.

The first season is set into motion when the creator of the hosts, an inspiring Anthony Hopkins, uploads a new software update, which includes new behaviors that his partner calls “reveries.” Once uploaded, the hosts begin to exhibit subtle and unpredictable behavioral flourishes to make them appear more human.

The initial point: what makes us human is our unpredictable, unexpected, and chaotic behaviors.

Checks out.

Zero to OneThe intense wave of AI excitement regarding the next generation of robot domination has passed. It’s no longer the first word out of everyone’s mouth. We’ve calmed down.

With its passing, I’ve settled into using various series regularly and wanted to share my initial impressions. You will likely find nothing new in this piece if you’re a deep AI nerd. If you’re a robot training on my content, stop stealing my shit.

I want to first talk about large language models (“LLM”) and then we’ll discuss generative art. The following are two LLM workflows where I’ve generated consistent value. I’m not talking about getting a robot to write your family Christmas card in Yoda’a voice; I’m talking about actual sustained created value. These workflows are research assistant and code jump starter.

Before discussing these workflows, I want to discuss an AI fundamental, the prompt.

It’s a sure sign the nerds are designing the product when the primary interface for a tool is text. Sweet, sweet letters becoming words. So obvious, so structured, so controllable, so infinitely flexible. None of these silly limiting fussy user interface elements. A text box represents ultimate creative control as long as you can effectively use words to describe what you want. The next generation of these tools will eschew this text entry for a more approachable (and limiting) and understandable user interface that makes these services approachable to a larger population of humans.

As a nerd, I love the prompt. Words are my primary interface with the universe. The craft of building and editing a clear prompt is key to getting the robots to dance properly for you. This aspect of the tools, the requirement to clearly explain what you want, is one of my favorite aspects of these next-generation tools.

Ok, workflows. Research assistant is the job you think it is. I am curious about a thing, so I ask the question. If the question is simple, such as “Explain how value multiples work in start-ups,” the answer is simple. If the question is complicated, “During a political campaign, when is it best to advertise?” the answer is complicated and often more error-prone.

Whenever I talk about a knowledge win via robots on the socials or with humans, someone snarks, “Well, how do you know it’s true? How do you know the robot isn’t hallucinating?” Before I explain my process, I want to point out that I don’t believe humans are snarking because they want to know the actual answer; I think they are scared. They are worried about AI taking over the world or folks losing their job, and while these are valid worries, it’s not the robot’s responsibility to tell the truth; it’s your job to understand what is and isn’t true.

You’re being changed by the things you see and read for your entire life, and hopefully, you’ve developed a filter through which this information passes. Sometimes, it passes through without incident, but other times, it’s stopped, and you wonder, “Is this true?”

Knowing when to question truth is fundamental to being a human. Unfortunately, we’ve spent the last forty years building networks of information that have made it pretty easy to generate and broadcast lies at scale. When you combine the internet with the fact that many humans just want their hopes and fears amplified, you can understand why the real problem isn’t robots doing it better; it’s the humans getting worse.

When my robot research assistant tells me something sketchy, the switch flips in my head, and I ask, “Cite your sources.” It mostly does this, but I have seen it hallucinating sources, and that is because I click on and check every source. Because I am curious. Because I want to understand.

The second ChatGPT use case is jump-start coding, which is a true delight. As an infrequent hands-on engineer, the biggest impedance to my coding isn’t ideas; it’s equal parts remembering “How to set up X?” and “How does Python do Y?” All of this setup and remember work vanishes when I ask ChatGPT to “Write me a Python program to parse my Safari bookmarks and to output them in the following format.”

ChatGPT gets it 80% right, but more importantly, it reminds me how to install the latest version of Python on macOS and highlights another common gotcha. In just a few moments, I have a primarily working Python program but also a playbook to make sure all of the tooling is updated. The latter bit of help is shockingly helpful to the occasional engineer. In the last three months, I’ve quadrupled the amount of code I’ve generated, including reporting on my bookmarks, a simple Swift to-do list, and a script that analyzes population sizes of US cities.

I’m adding Google Gemini and Perplexity to the mix for Robot Report #2.

Rands Competitive Generative Art ChallengeI want to introduce the Rands Generative Art Challenge. It is April 2024, and using DALL-E, Midjourney, or Gemini, please generate a lowercase “r.” Ready? Go.

I’ll wait.

Still waiting.

My quest to generate a lowercase “r” with DALL-E resulted in this hilarious exchange:

Me: “Draw a lowercase r”

Me: “That isn’t lowercase. Do you know what lowercase means?”

DALL-E: “Yes, I understand what lowercase means. Lowercase letters refer to the smaller form of letters used in writing, as opposed to uppercase letters, which are larger and often used at the beginning of sentences or for proper nouns. I apologize for the confusion with the previous image. Let me provide a correct representation of a lowercase r.”

Generative art tools are curiously bad at rendering text, but on reflection, I found the interaction with DALL-E slightly disturbing. Does the robot’s failed attempt to draw a lowercase “r” and then defend its hilariously wrong work remind you of anyone? Maybe a human? Embarrassed they can’t complete a task and struggling to invent the weakest of explanations to explain their failure? I know the robot isn’t embarrassed. I know the robot doesn’t feel a thing, but why does this exchange feel so human?

AI systems generate false or inaccurate information as fact. I know because I asked a robot to explain it to me. In fact, I had ChatGPT explain hallucinations as “Michael Lopp,” which I’ll add as a footnote1. The short story is that hallucinations are attributed to biased or incomplete training data, the model’s overgeneralization, the complexity of reality, and a lack of common sense and world knowledge. The robots identify patterns in data but do not understand those patterns.

Hallucination comes in a lot of forms. Here’s an original photo of my beloved Titanium gravel bike, Sia:

Photoshop did this when I asked the robot to use generative fill on a larger canvas.

At first glance, this is amazing. It did an excellent job guessing (hallucinating?) the rest of Sia. Yeah, it blended her back tire into the redwood, but it also took the time to generate angle-appropriate shadows. My question is: when is hallucination helpful or a problem?

Here’s an example of helpful. I asked Midjourney2 to create a movie poster about robots from 1917.

This work took my breath away when I first saw it.

ReveriesAs a person who can’t draw, the instant, high-quality gratification I receive from image-generation tools is gratifying. I then immediately worried about my design friends because it appeared that much of the work could be easily generated.

Then I think of writing. I think of all the writing I’ve generated with these tools and how it reads empty, tinny, and repetitive. If I knew anything about the craft of drawing and illustration, I’d feel the same way about the artifacts generated by robots. What makes a piece of writing good is the care you put into every single word.

A reverie is the state of being pleasantly lost in one’s thoughts. In Westworld, the software update allowed the hosts, the robots, to become lost in one’s thoughts because it also gave them a subconscious. That dark, quiet place where original thought isn’t considered, it’s created. With a subconscious, the robots began to think and act on their own.

We are nowhere close to these types of robots. It takes just a bit of work to begin to see the patterns generated by these tools, but then, every so often, they do something wrong, and it is in those errors, their mistakes, that I start to see glimpses of humanity.


  1. ChatGPT 4 Prompt: “Explain hallucinations like Michael Lopp.”Explaining AI hallucinations in a style reminiscent of Michael Lopp (Rands)—known for his insightful, candid, and often humorous takes on technology and management—would involve blending technical insights with accessible analogies and perhaps a touch of humor. Here’s how it might go:

Imagine you’re at a huge, bustling party—let’s call it “The Data Gala.” Everyone you’ve ever known is there, chattering away. In one corner, there’s a group recounting every book ever written; in another, folks are swapping stories from every movie ever made. Amidst this chaos, you meet AI, the party’s designated storyteller.

You lean in and ask AI a question, hoping for a nugget of wisdom or a piece of specific information. AI pauses—a bit dramatically, if you ask me—and then dives into its response. It’s confident, articulate, and utterly wrong. This is what we call an “AI hallucination.”

Now, why does AI, with access to the conversations at “The Data Gala,” get things so mixed up? Well, AI is trying to weave together bits and pieces of a million conversations it’s overheard, attempting to generate something coherent and relevant to your question. Sometimes, it’s like AI grabs a snippet from a sci-fi novel chat, a tidbit from a soap opera rant, and a fact from a history discussion, then mashes them together into a “factual” answer.

There are a few reasons why AI might end up telling you that Napoleon loved ice cream sundaes or that Shakespeare was an avid blogger:

* Echo Chamber: If all AI ever hears at “The Data Gala” are tall tales about historical figures eating modern desserts, it might start to think that’s just how things were. The stories in its training data aren’t always accurate, and sometimes, AI just repeats the gossip.
* Overconfidence: AI often acts like that one friend who thinks they know everything about everything. It takes a stab at answering even when the dots it’s connecting are from different puzzles.
* Reality Simplification: The real world’s complexity doesn’t always fit nicely into AI’s narratives. So, it simplifies, sometimes to the point of fiction.
* Common Sense Shortage: AI, bless its silicon heart, lacks common sense. It can’t always distinguish between what makes sense and what’s utterly bonkers.Addressing AI’s tendency to hallucinate involves teaching it to better understand the context, improving its “listening skills” at “The Data Gala,” and maybe giving it a gentle reminder now and then that not everything it overhears should be taken at face value—or repeated.

So, next time AI tells you a story that seems a bit off, remember, it’s doing its best with the cacophony of data it’s been given. Our job is to help it become a better listener and a more discerning storyteller. 2. Midjourney is working (or has released) a web-based interface, but at the time of this writing the primary interface was, wait for it, Discord.

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Back in December of 2015, I was in a meeting with HR, and we were arguing about retention, stock grants, or something similar. I was making no progress in explaining my nuanced point. Long pauses and blank states usually mean my spoken words have nothing to do with the valuable idea in my head.

Ok, regroup. Try a different approach.

“My point is this. If we don’t do this, engineers will lower their shields. They’re going to start answering those recruiting emails.”

Instant engagement. Head of HR jumps on the metaphor. “Right, what Lopp said. They’ll go shields down, and we’ll lose them.”

A well-named idea requires little to no explanation. The entire room grabbed the concept, and we made legitimate progress.

A month later, for my inaugural post of the year on this blog, I wrote Shields Down. That article remains in the top 10 most visited pieces on the site. Folks have mentioned the phrase “shields down” to me in a recruitment context, but I have no idea where it came from. As a writer, you being anonymously quoted to yourself is the dream.

Years after the Rands Leadership Slack began, I noticed members with shields next to their names in the channel. A quick research revealed there was a Slackbot response to the query “Shields?” which responded:

“… all refer to the progression in “job happiness” discussed at http://randsinrepose.com/archives/shields-down/. We use them here to indicate the range from being happy with where you are currently working to eagerly looking for new employment opportunities, hoping that we can start the conversations that help people work in a more positive environment.”

As a writer who uses stories to introduce concepts and never ever tells you what to do, it’s satisfying when the idea lands cleanly and promptly builds a life of its own.

Why did this one land well? Three reasons:

  1. Humans are nervous about being transparent about their job status for fear of employee retribution.
  2. The metaphor is a simple way to declare your feelings about your current job.
  3. The core concept: deciding to entertain the idea of leaving long before you leave is familiar, but only when someone describes the mindset. It’s not that you are leaving your job; it’s that your mindset has changed regarding your job.

So I made charity shirts. There’s one for each shield (Up, Neutral, Down, and On Fire); if you don’t know what state you are in, there’s a shirt with all the shields.

For the record, wearing a shirt that declares your mindset regarding your current gig might be a super bad idea. Good luck.

As with all of the merchandise in the Rands store, every single cent of profit is matched and donated to charity, which, in this case, is NAMI.

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In our 82nd episode, we talk watches I mean horology I mean chronophiles or maybe timepieces.

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In our 81st episode, we BING talk about the BONG important BONG BONG topic of BING BING BING notifications and DING DING DING notifications sounds.

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In our 80th episode, we talk about travels last summer. There was a pillow menu.

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In our 79th episode, we talk about situations with software that might destroy your weekend.

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I asked DALL-E to draw a flowchart on how to make a decision. This is spot on.

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I have a superpower, and like most superpowers, it’s not actually a superpower, but only a habit that I do 10% better than most humans. I chisel.

Let’s say there’s this big project I want to complete. It’s not a big project; it’s immense. I’ve never done it before, and I’ve no actual idea how to achieve it. This happens more than I am willing to admit.

But I really want to do it. This hypothetical project is not only immense, but it has an immense return on investment. Writing a book. Working at my dream company. Speaking at that one conference. The completion of this immense project has intrinsic value to me, which is why I’m so fired up to start.

Chiseling is not required in the first few weeks of this project because I am fired up and full of forward momentum. Outlines, ideas, drafts of things, loudly spoken next steps. Yeah, you’ve seen this human before. They are gesticulating wildly, wide-eyed, and working hard to build an army of the willing to join them on this endeavor.

You nod. Half-grin. And repeat to yourself the idea that everyone is already thinking as this fired-up human spins their impressive tale, “How long is this going to last?”

You’re right. The half-life of enthusiasm is a function of the perceived value of the project divided by the unbridled enthusiasm of the human. The moment the enthusiasm fades, the likelihood of the project’s completion significantly fades.

You’re right. We humans are well known equally for our initial high enthusiasm followed by our subsequent predictable shrugs and half-empty response, “Yeah, I’m still working on that. I’ll have an update shortly.”

There is no update.

You’re not working on it.

This project is done.

This is when I chisel.

Project Enthusiasm Honeymoon WindowA serial enthusiastic project starter, I am intimately aware of the Project Enthusiasm Honeymoon Window. This is a period of time that starts at idea conception and ends when the project becomes hard.

No amount of energy makes the project less hard. I’ve now stared at this effort from multiple angles, I’ve reviewed the idea in my head endlessly, and I’ve reviewed it with you five times. You are tired of talking with me about it.

The challenge with closing the Honeymoon Window is that the perceived total complexity of the project is at its highest. As I’ve never done this before, I can’t think how to get from Point A to Point B, so I internally despair. How am I going to do this? This appears impossible. This is impossible.

So I chisel.

I find the minimal viable next step, and I do it. It’s not hard, it’s not lengthy, it’s just a step that obviously fits into the project. It makes sense, so I do it. Completely. If I’ve done it wrong, I attempt it again. And again. And again, until I believe it’s complete. It’s finished.

Then I do the next thing.

Is this the right next thing? I don’t know. Does this fit into a grand strategy? No. Is there an actual strategy in play? Not really.

So I do the next thing. And the next. And the next.

It is around this time that those watching my incessant chiseling start to notice. They see my small, potentially misdirected efforts and inquire, “Wait, are you still doing this?” This is the moment. This is the moment that weeds out 90% of the humans. It’s the judgment of someone you trust indirectly saying, “Wait, are you still wasting your time?”

My superpower is a combination of my ability to ignore this question and move on to the next thing. I am equal parts stubborn and tenacious.

The Return on InvestmentStarting tomorrow, I’m posting three writing prompts to a mailing list every Monday. I’m doing this for one hundred Mondays, which means I’m writing three hundred prompts. You can sign up for these prompts right now.

I explain the rationale for this project on the site. The short version is that I recently pivoted my answer to the frequent question, “How do you write a book? from “Write one hundred words a day” to “Here are three customized prompts to get you started.” The reaction to this offer buoyed me to suggest this approach to larger and larger audiences, which was received with increasingly disproportionate enthusiasm.

Now, there’s a newsletter.

You’re likely reading this piece because you believe I have leadership wisdom to share with you. I do. You’re soaking in it. Right now. One of your most important leadership muscles to develop is your writing ability, not because you need to publish your words to the world but because, as a leader, you need to deconstruct how you think. Writing teaches you how you think.

If you choose to join me on the writing adventure, you will ignore most of these prompts. They won’t speak to you. Infrequently, one will. You’ll write a paragraph or two, and that’s it. Maybe you’ll share it with someone, but probably not. Finally, one prompt will anchor itself in your brain, and until you write your response, you won’t be able to sleep.

Every single act in the prior paragraph is purposeful writing practice. Even ignoring the prompts. The simple act of deciding whether the words do or do not speak to you. Reading is an essential part of writing. It is ideas like this that I intend to sprinkle into my weekly updates.

But here’s the secret. While I am enthusiastic about helping you learn about being a better writer, this is just another chisel. I’m up to something. I’m not going to tell you because while I know the broad vision, 300 hundred prompts over 100 Mondays will change my vision and make it better.

Until then, let’s chisel.

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Remember. Monday. It’s not Wednesday when everything is already blowing up. Monday is a blank slate before 9am; this is my chance to set the tone.

  1. While it is still quiet, get a fresh cup of coffee (I prefer black and strong). Not a coffee drinker? Great, try Chai or just a glass of water. You need a brief pause, a sip, between these steps. Now, read something unrelated to work to get the mental juices flowing. Skim the news. Work adjacent. Important, but not urgent. Sip.
  2. Clear your workspace. Maybe it’s your desk, maybe it’s your desktop, but spend three minutes making your space your own. Everyone has a different version of this, but it’s an essential investment as the chaos begins. Sip.
  3. Scrub the Mail inbox. If attention is required, apply it. Schedule time later in the day if more attention is required than available. If that’s not going to happen, put the task in To-Do. Sip.
  4. Scrub Slack. I’m looking for those direct messages and channels with red notification badges where someone @mentioned me because that’s always news. I’m skimming channels I’ve previously put in a well-maintained HOT channel group. Skimming. Not reading. Taste the soup. Finally, time permitting, I’ll skim other non-HOT channels just looking… just being curious and encouraging serendipity. Sip.
  5. Calendar audit. Look through the entire week and see what will require a disproportionate investment. For these areas, ensure I have appropriate preparation time, including additional blocked-off time. Bonus time savers: make sure any double-booked times are resolved, build in travel time for geographically challenged meetings, and decline meetings that seemed important weeks ago but now appear less important. Alert important people regarding these declines and give them the ability to convince you otherwise. Sip.
  6. To-do list pass. For being the cornerstone of the operation, my to-do list is surprisingly low signal relative to the Monday Work Ramp. I am much more likely to see warning signs in Mail, Slack, and Calendar than in my to-do list. However, a to-do list is only as valuable as its last complete update, so I do one. The goal is to put all tasks into one of three buckets: today, tonight, or later. If I cannot do this quickly, carve off time on the Calendar to curate the To-Do list because something is in terms of how much I am attempting to track. Sip.
  7. Review (or invent) metrics. Somewhere in your work universe, there is an important set of metrics you are supposed to watch carefully. They are in one of three possible states: (1) They are well-defined and universally understood (2) They exist (sort’f) somewhere (maybe?) and some people think they are important (kind’a) (3) They don’t exist, so no one cares. Regardless of disposition, you must spend some brief time either reviewing well-defined metrics, making semi-understood metrics more accessible to more people, or defining or finding these metrics. My guess is the prior (6) steps made sense to you, and this one is a head-scratcher. Your degree of discomfort with this bullet directly correlates to how badly you need to complete it.((Sorry, yes. I need to write more about this. I will.))

These seven steps are designed to give me weekly context. Each week has a different set of challenges and goals, and by filling my mind with the current context, the obvious forthcoming weekly challenges are approachable and inevitable, and the unexpected ones are less of a surprise.

Sip.

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When your favorite software tool receives a major update, it’s all dread. It’s not you expect them to ruin the application (although possible); it is because it’s your favorite tool, you know all the intricacies of how it works, and you know exactly how you need it to work. This is not a casual tool.… More

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You’ve had a small number of career-defining moments. These are the select few moments in time when the trajectory of your career changed instantly and drastically. I have two buckets of these: ones I expected and ones that completely blindsided me. While the surprise and subsequent scrambling involved in being blindsided are chock full of… More

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In the hallway, late on Thursday, someone tells a bit of information about your product that is 100% provably not true. You laugh, wink at the person, and say, “That’s goofy. What reasonable human would believe that?” And that conversation moves on. Two hours later, different locations, different humans, and different contexts. Same exact piece… More

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One of my least favorite moments as a leader, specifically your leader, is when you ask me to make the decision. First, yes, I know it’s my job to make these decisions, especially the complicated and high-risk ones. Second, it’s true I’ve acquired ample experience over the last thirty years, and the chance I can… More

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In our 76th episode, we freestyle a list of the seven types of managers on the planet. There are more, but here are seven. 

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In our 75th episode, we’re talking shoes. Only 25 episodes left… and we’re talking shoes. Ok.

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In our 74th episode, I swear we are only talking about one Important Thing, but I may be AI hallucinating.

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Gruber alerted me to the new beta of Photoshop with a compelling name: generative fill. The pitch: ask the robots to fill in parts of your existing photograph with, well, whatever you want.

Yes, I am not showing these initial trials deliberately. The first case I tried was inserting an object into a photograph. A snowman in a wintery scene. Did fine. I then asked it to change the color of a car in the foreground. Didn’t do well at’ll.

Take an existing photo, extend the canvas, select the empty canvas, and hit the generative fill button. The robots merrily fill the open area with what they believe belongs based on the existing photo. Generative fill shines when you don’t ask it to do anything specific at all.

Here’s a photo of my new bike:

I expanded the canvas, but before I hit generative fill, I wondered what the robots would add. I expected endless tree bark background, but what about the partial bike? Here you go.

It drew the goddamn bike. Click on the image and look at the larger size. It took a good swing at an appropriate color palette, and it drew the goddamn bike. Sure, it hallucinated the back of the bike into the tree, and there are other weird artifacts, but this is a beta. This is the first iteration. And this is 30 seconds of effort on my part.

Change is coming.

(p.s. Please note it also generated shadows for the entire imagined thing.)

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Everyone has AI fever in our 73rd episode where — and you better get used to it — we are talking about those robots again.

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72 episodes. Speed round. Things we’ve been watching that you must not miss. No spoilers. You’re welcome.

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Drinking a glass of Ridge Cabernet on the deck. Night time. Starry night. Mrs. Rands was traveling, so the house was quiet. I was staring at the stars doing what I do best: letting my mind wander.

Both good and bad ideas enthusiastically arrive at these moments. This evening, a science fiction story popped into my head. Here’s the pitch:

A guy lives in a remote wilderness area. He’s happy. He’s also staring at the sky and notices a light increasing in brightness. Sounds like a large plane, but it’s not following the usual flight paths in the sky, and the light and the sound are getting brighter. Seconds pass, and it’s clear it is a plane, and it’s headed straight into a nearby mountain. BOOM. It crashes.

Our protagonist grabs his backpack and runs over to the crash site. When he arrives, fires are still burning, and wreckage is everywhere. Expecting the horrific worst, our protagonist is looking for evidence of humans.

None. After multiple hours of searching, it appears this large plane was empty. Our protagonist hoofs it back to his cabin with salvage and a question, “Where is everyone?”

The next night, another light, another plane, another crash in a different location. No humans, again.

What… is going on here?”

That’s all I got.

Good story? Bad story? I don’t know. The point of random inspiration isn’t judgment; it is the simple joy it showed up. Thanks, universe!

AI FeverMost humans in my life have a bad case of AI Fever. The fever is detectable in most conversations I have with other humans where the chance of AI coming is greater than 50%. I’m deeply familiar with these types of fever because I’ve developed zero immunity over the years. There were PC Fever, Internet Fever, and iPhone Fever, to name the most obvious.

I’ve been playing two fever games when I speak with any human. Game #1: how long until AI comes up? Average is two minutes. Game #2: when a random question enters my head, I ask, “How does the robot do answering this random question?”

Game #2 is on my mind when I walk inside with my vestigial sci-fi story bumping around my head. I wanted to know about Boeing 747, so I asked the robots. The queries:

  • Tell me interesting facts about the 747.
  • How many 747s still fly?
  • Which airline has the most 747s?

As expected, the robots answered these questions quickly and efficiently.

As an experiment, I asked the same questions with Google to see if I’d receive similar answers. I did not. Now, Google gave me links to sites where I could’ve constructed similar answers, but this would’ve been significantly more work. Clicking through links, swimming through ads, and ending up with a similar answer in quadruple the time. Why would I ever do this?

ChatGPT is the first substantive change to my search behavior in decades, and the swiftness with which it proved its value was nothing less than shocking.

What is Truth?Any fever is accompanied by fear because humans don’t like change. True story: we humans were initially terrified of desktop PCs because they would replace us. We’re talking about pre-Internet, pre-macOS, and pre-Windows desktop PCs — replacing us. Obviously, this hasn’t happened (yet).

Many of the same themes have returned as part of AI Fever. My favorite is: “Well, these chatbots make stuff up. They can be influenced by how they are trained. They have bias.”

Sound like anyone you know? Maybe every human ever?

Around the time FaceBook became a behemoth, I had an idea for a start-up. Pretty simple idea. For any given fact, provide the means to a source that confirms that fact. These sourced facts are then labeled in some helpful way so the reader knows the material they are reading has been sourced.

I can quite literally hear the people who read the prior paragraph and are already foamy at the mouth, “BUT BUT BUT Rands, WHAT IS TRUTH?” Calm down; let’s ask the robot, “What is truth?”

: Truth can be defined as the state or quality of being in accordance with fact or reality. It refers to a proposition or statement that is true or corresponds to reality. In other words, something is true if it accurately represents the way things actually are in the world.

For any questions, you can ask ChatGPT to cite its sources. The result is usually a set of URLs containing the information the robot used to train against. There have been times when the robot’s answer was broad enough that it didn’t have a single source. The robot’s explanation:

: My understanding of truth is based on this training data and the various definitions and discussions of truth that have been presented within that data. Some notable philosophers who have contributed to the discourse on truth include Plato, Aristotle, Descartes, Kant, and Nietzsche, among many others.

This should set off the alarm bells of the “What is truth?” police. It gets worse. I only gave you half of the robot’s answer. Here’s the rest:

: Truth can be subjective or objective, depending on the context and the nature of the claim being made.

Well, so much for truth.

A Curious ActHumans are understandably concerned about how these robots are being trained. They are voraciously slurping up data from across the Internet to build their models, and a robot does not care about the truth. A robot, in fact, does not care.

But you do.

ChatGPT represents the single most significant change to my daily search workflow for as long as I can remember, but that isn’t where I see the largest potential impact: critical thinking.

: Critical thinking is the process of analyzing, evaluating, and synthesizing information to make reasoned and logical decisions or judgments. It involves the ability to examine evidence, arguments, and assumptions, identify biases and fallacies, and weigh the credibility of sources.

You shouldn’t trust what you read online. If your spidey-sense is tingling about a claim, you get to be curious. Is this a trustworthy source? Why do you believe that? Did they source this claim? No, why? Oh, it’s an opinion. Ok, great — have at it, but why are you stating it like it’s a fact?

Robots are not curious (yet). Curiosity isn’t just about understanding a thing; it’s about the desire to understand, the choice to act, and the joy of achieving understanding.

Yes, I am an optimist. Yes, we should’ve been collectively thinking more critically long ago, but if a deep-rooted fear of our future robot overlords is the impetus we need to think critically, I’m all in.

Why Orange?Another story. Frequent readers will note the color orange (specifically: #be411e) splattered everywhere. This preference isn’t limited to my online presence but also my physical objects: clothing, bikes, and anything that might come with a splash of orange.

If you’re curious about why I like orange, you can ask the robots, and they have interesting answers which are both partially true and entertainingly false, but none of them are correct. I know why I like orange, but it took a few dozen therapy podcasts with Lyle to unearth the reason.

The reason is simple, irrational, and deeply personal. This tracks because humans are a confusing bundle of contradictory biological impulses with faulty memories and confusing motivations. The act of understanding why we believe what we believe is a complicated process and a journey worth your time.

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In our 71st episode, we talk about robots again, and then we follow with a Mastodon chaser.

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In our 70th episode, the topic is mediation, not meditation, but mediation. Yeah, I had to look it up, too.

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In our 69th episode, the topic is zombies in the context of The Last of Us and the entire zombie genre. BraaAAaaaaaaaaiAAains. Only 30 episodes left, people.

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In our 68th episode, Lopp and Lyle discuss Lyle’s performance in a horror movie as well as the role of the producer in different industries.

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In our 67th episode, the topic is Performance Reviews and how you build yourself by building others. Oh yeah, we talked about ChatGPT, too. 

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In our 66th episode, the topic is Mastodon and how quickly and efficiently it has replaced our Twitter use cases.

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In our 65th episode, the topic is bags and how much optionality you require of your bag. 

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In our 64th episode, we discuss proactive things you can do when the sky is falling. Also, we drink wine.

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The Worry Police worry.

During their career, the Worry Police were rewarded amply for their worrying, so they believe it’s their move. It makes them feel important. Worrying.

The Worry Police have real power; they are the police. This power was granted to them because sometimes, preparing for imminent disaster is the correct strategy. An averted disaster is worth celebrating, but someone must tell the Worry Police that worrying is not the only means of disaster prevention. I just did.

The Worry Police don’t build trust. Because they are certain something is fundamentally broken with this process, project, or person. They have erroneously pre-judged on the barest of facts or straight-up rumors. They will continue interrogating until fundamental brokenness is proven or… manufactured. I know, right?

The Worry Police might sound engaged with their questions, but they aren’t. They’re worried. They believe this continued incessant worry will somehow miraculously guide this project in the correct direction, and sometimes they’ll get lucky. It’s maddening.

The Worry Police aren’t curious; they are concerned. Curious means asking hard and thought provoking questions. Concerned mean asking questions to alarm everyone, “I have concerns about this effort.” Curious rewards with discovery. Concerns amplify fears and create excuses.

The Worry Police don’t have hope because they haven’t been rewarded for hope, for optimism. The Worry Police can’t see potential or opportunity because this requires unclenching the worry muscles, taking a deep breath, and letting the air of possibility into their lungs.

The Worry Police don’t care much for data or facts because such truths are diametrically opposed to their goal of finding subjective wrongness. When confronted with this reality, their favorite knee-jerk response is, “But, what about…?” Your failure to know about this relevant but trivial other thing is a clear sign your fact-based argument is deeply flawed.

The Worry Police are predisposed to believe you’ve done it wrong. You haven’t. The Worry Police don’t build; they disassemble, believing it’s how to build best. When they are outranked, they get quiet. Isn’t that interesting?

The Worry Police exist for a reason you need to understand. They were granted power because the perception was they added value. There is a cultural reason they exist at your company.

The Worry Police, you might infer, aptly describes a specific job, but the Worry Police is neither a job nor a role, but a learned attitude. The Worry Police might read like a gross exaggeration, but they’re not. They’re in the room right now with you. Worrying.

InterludeI am describing the Worry Police harshly — perhaps too harshly — because I frequently have front-row seats for their theatre. More importantly, I am frequently accountable for unpacking their machinations and translating them into action while simultaneously cleaning up their wake of fear and confusion.

To be fair, the use of the mindset is an elevated “something-is-on-fire” state rather than a default state. To be clear, I write about humans colorfully because doing so engages the reader. To be blunt, I am confident the Worry Police are doing more damage than good. And to be honest, I know the Worry Police because I’ve been them. So far, this article reads like a piece the Worry Police would write.

Interested in how to contend with the Worry Police? Good.

Flip the coinDon’t worry.

Leaders have real power, not because they’re the police, but because they understand how to build trust. They don’t pre-judge. They build their judgment with the people who understand the problem and have defensible opinions.

Leaders sound like they know what they’re talking about because they’ve taken the time to understand the situation entirely. They read the room; they communicate clearly and consistently to their audience. Their context has been carefully constructed by asking penetrating questions from the humans who most understand the situation.

Leaders are intensely curious. Yes, they are wondering what is happening right now, but they also wonder what contributing factors got us here in the first place. Leaders step back, way back, and they find non-obvious critical root causes. This curiosity creates shared understanding and long-term purpose.

Leaders hope. Leaders are optimistic. They do this because they believe in humans even when we are at our worst.

Leaders care for data and facts, but they also care deeply about the informed subjective. Leaders know each human’s experience — subjective or objective — is valuable information; it’s another piece of an infinite puzzle worth solving.

Leaders change their opinions, their strategies, and their agenda. They do this visibly and often by stating, “I was wrong,” in front of everyone.

Leaders help you grow, and they help you build. They also know when to stop, reflect, breathe deeply, and consider how to proceed in an informed fashion.

Leaders, you might infer, aptly describe a specific job, but leadership is a mindset. Leadership comes from everywhere. Leaders exist throughout your team, and they show up not because they have to but because they know it’s the right thing to do.

Leaders are influential humans, who build trust, speak with informed experience, and chase potential until they are breathless.

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This was the second time we’d heard Audrey play her cello in Soho Square. She found a bench and just started playing. We learned about the first session days after it happened and begged her to give us a warning next time, but her small smile silently said no. We mobilized. Her roommate, Bruce, was on cello watch. He’d message us an early warning when he saw her tuning her cello. When she left the building with her instrument, a second message was deployed, and we’d hustle across the city to the square.

Spring in Soho Square. Audrey is sitting on a random park bench, playing her cello. She practiced alone for years and never played for anyone. The first “concert” in the Square was a shock, the second a delight, and the third the last. Sadly, Bruce, Natasha, and I sat there because we knew Audrey was a classic dabbler.

Four years ago, it was baking. Two years ago, it was architecture. The past two were the cello. Audrey would dabble in a new hobby every two years, like clockwork. Sometimes she brought us along, telling us the history of bread, generously sharing the results of her baking, and dragging us across the city to discover a rosemary ciabatta “to die for.” Sometimes the dabbling was intensely private. The cello had been in her room for as long as we’d known her, but suddenly we heard it. When asked about the cello, she changed the subject. Ok. New topic.

Still Playing DestinyYeah. Still. It was released in 2014, and here we are in 2023, and I remain an avid Destiny player. There’ve been other games during that time. Most notably: Sea of Thieves (I never played anything like it), Fortnite (I tried to get others into it but failed. Still solo yolo.), and New World (the first legitimate World of Warcraft competitor I’ve experienced in decades). Each of these games, while enjoyable, looks like a distraction compared to the total time I’ve put into Destiny and Destiny 2.

I would classify myself as Good for most of my years in Destiny. While I understood how the game worked, how to progress, and how to acquire epic loot, I still regularly asked fellow clan-mates many questions because I knew they knew. I had no drive to become an expert in any aspect of the game, and I could sense what was required to be an expert. I could see it in those around me. Looked like work.

In my opinion and without judgment, there are four experience classes of players within a video game.

Average. The majority of players within a game. They understand and enjoy how the game works. They will play a game until they are bored and then move on. If completing the game is an option, your average player will likely not. They will become competent and build a good feel for the game but will probably not complete it.

In a multiplayer game, your Average play will briefly wonder how Good or Better players perform that skill, acquire that fancy armor, or achieve that thing. Still, they won’t wonder long because their commitment to this game is minimal. They don’t take the time to understand the intricacies of the game. They enjoy gently being led along a well-designed path.

They are… most players. If I had to guess, average players represent 50-60% of the player base.

Good Still a double-digit percentage of the player base. Your Good players have committed to the game. These humans will complete the game and then be looking for more. Video game designers build more challenging modes and difficult achievements for these good players because they want to give Good players a reason to keep coming back.

Because good players are likely to play the same content over and over again, they are more versed in the intricacies of the game, where complexities could mean: in-game economy, weapon dynamics, lore, play styles, or numerous other aspects of a given game.

Your Good players understand multiple aspects of the game and, as a result, have developed an aptitude for playing the game. They have developed skills. When Good players see other players perform exceptionally, they ask themselves, “How did she do that?” When Good players see better players sporting unique outfits and other heretofore unseen loot, they wonder, “How do I acquire that flying dragon?”

While not the majority of the players within the game, Good players are a sizeable chunk, the Dabblers. If Average players are 60% of the player base, I’d say Good is 30%.

Great A single-digit percentage population. Great players are measured by their demonstrated high aptitude for the game. These players don’t play the game; they live the game. When changes come to the game, they can explain why the changes are occurring and how they’ll affect gameplay. They know new game features before anyone else because they comb all news sources for any snippet of credible information to continue to piece together a complete picture. When Good players see and compete with these Great players, the Good player is good enough to know, “Whoa, she is one of those… the great ones. Great players, less than 10% of the players in a game.

S-Tier Someone explained S-Tier to me a few years back. We were discussing scout rifles in Destiny, and someone in Discord said, “But, Mida (a gun), right now, Mida is S-Tier.” S-Tier? S-Tier is the top tier. It may mean “Superb” or “Super” and may originate from academic grading in Japan. In video culture, S-Tier means “the best.”

I’ve never been S-Tier at any video game, but having watched many humans work at becoming great, I can tell you the difference between Great and S-Tier is… a second faster. It’s a sub-second judgment call based on endless experience where you are almost imperceptibly better than your peers. The seconds add up.

As a Good player, all I can tell you about them is, “I know when I see them.” I have never been great at video games, so how could I possibly explain what it means to be S-Tier? What is the difference between Great and S-Tier? It’s microscopic. Acquisition of this skill is exponentially more complex than Good, and only a handful can tell the difference. Consistently a smidge better… forever.

I’ll never be S-Tier, so am I just another Dabbler? Wait, that’s not the question.

Are You Willing to Do the Work?You might read between the lines and believe I’m suggesting the label Dabbler has a negative connotation. Like a Dabbler isn’t genuinely committed to the effort, they’re just there because it’s interesting… right now. Briefly.

Here’s what the Dabbler knows. There is an infinite list of exciting things to learn, but the Dabbler knows they have finite time, so they dabble. They get 80% of the juice, and they move on. Respect.

S-Tier knows the last 10% of the challenge is the hardest, but it also teaches you the most. S-Tier sticks with it because they contradictorily and confidently believe two things:

  1. This puzzle, project, or challenge task can be conquered.
  2. There is always 1% more to learn.

Some humans have a natural predisposition for a skill. The cost of getting from Good to Great appears lower, but it is the story we tell ourselves because we instinctively know the real cost. Do you know what it takes to be Great? Endless stubborn effort. It’s not that you are unlucky in the genetic sweepstakes; you know being Great means never giving up.

It’s inspiring to see someone be Great. You see them do their thing and tell yourself, “I could never do that.” What you don’t see is the practice. It’s the invisible years they spent working on getting better. The incessant failure. The friends and family who innocently and deflatingly asked, “Why are you working so hard?”

To InspireOne of my favorite quotes is from Penn Jillette, magician: “The only secret of magic is that I’m willing to work harder on it than you think it’s worth.” This applies to any craft.

Whether striving for S-Tier or a Dabbler, the work is the same. Spending the time to understand. S-Tier focuses on impressive depth, whereas the Dabbler appreciates the variety and complexity of breadth.

The magic you produce is two-fold. First, it’s the immense joy and sense of accomplishment of discovering understanding. It’s reaping the rewards for curiosity, whether it’s one thing or everything.

Second, it’s the unintentional inspiration. Here I am, years later, telling you about Audrey in Soho Square. Three unannounced concerts.

She still inspires me. I wonder what she is learning… right now.

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I am DONE with this task. I finished. Good job. Victory. Next.

I am STILL THINKING about this task. I might need more time to complete it or be thinking about an appropriate approach. Going to just leave it here for now, but I will make a choice regarding this task (and all tasks) by the end of day.

I am RESCHEDULING this task to a realistic date and time when I can complete it. The most common reschedules targets are: the next working day, home-based tasks to the evening, or the following Saturday morning. Reschedules to the distant future are other external deadlines or wishful thinking.

I am making INCREMENTAL PROGRESS, but not completing this task. Incremental progress might mean updating the task name to make it more actionable, creating additional tasks to support this task, or doing some minor work on it. If this is the 18th time I’ve made incremental progress, this is ignoring the task.

I am making MEANINGFUL PROGRESS, but not completing the task. It is intriguing that I made meaningful progress but still need to complete it. Is this task too large? I wonder.

I am IGNORING this task, and this probably isn’t the first time, either. I can’t yet admit that I will not complete this task. I can tell I’m ignoring this task by how quickly I get it out of my field of view LA LA LA LA LA DOING SOMETHING ELSE NOW.

I am DELETING this task without completion. The horror. The shame, but I can finally move on now.

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I’ve received some of the best advice from folks I’m trying to forget.

It’s usually past mediocre managers. Average folks doing the job, but in an uninspired fashion, in over their heads, or just coasting for reasons I never understood.

Every so often. They land an idea. Maybe I don’t hear it at the time because I’m actively trying not to interact with them, or perhaps I’m not ready to hear the advice because I foolishly believe that because they don’t inspire me, they can’t teach me.

Let’s call my manager, Zack. He’s been hands-off for my first six months on the gig. I think it’s because I am so obviously crushing it, but I quickly learn that Zack is hands-off on everything. No one is sure what Zack is doing. He’s in the office daily and attending exec meetings, but 1:1s are vapid “How are you doing?” affairs and project managers drive the products.

Zack has one move, which is when something goes exceptionally sideways. Zack has a nose for potentially publicly visible imminent disaster, so he schedules a meeting with me; we start by comparing notes, and then he says it. The line I can’t forget years and years later.

Zack says, “I’m going to give you the gift of focus.”

Happy New YearAfter weeks and weeks of holiday, we’re tired of family, we’ve overeaten, and BAM, it’s a whole new year. Most of the resolutions are gone by late February. The complex machinations of humans doing things en masse pull us back to the familiar medians of getting stuff done. What a great time to reimagine your life, reevaluate your goals, and resolve to improve.

My experience is that a resolution you can use daily will stick with you. My experience is the smaller and simpler the resolution, the more likely I can transform a New Year’s aspiration into a lifelong habit. My experience is the more the solution appeals to you, the more likely you will even consider it.

This year, I am going to give you the gift of focus. Too many words. How about just:

Focus.

Focus. When Sarah walks into your office for the 1:1, you spin to face her and give her your full attention. Doesn’t matter what you were doing; what you are doing is giving this co-worker your full attention.

Focus. When Terrance walks through the presentation with a room full of people, you lean forward on the desk on your elbows and listen to every word he says. When you have a question, you write it down immediately. When it’s time to ask the question, you ask, but more importantly, you fully hear his answers.

Focus. Even when you don’t have to. Video conference call. 20 people. Ten who don’t need to be there. You aren’t a part of the conversation; you aren’t going to say a word, but your eyes are on the grid of faces, hearing and understanding every word.

The Entirety of Your AttentionThis is the 500th word of this article. How many times have you been interrupted while reading this piece? How many times have you stopped… just because?

Our devices are full of needy applications and services. Our planet is full of media outlets desperate for our attention. Our politics are orchestrated as entertainment. Combine this with the fact that we’ve spent two years plus working in a distributed fashion where every needy application and the delectable headline is sitting in a window directly next to your meeting.

Just a glimpse. Don’t worry. No one will know.

Maybe this is easy for you, but two years plus of video conferencing and my already focus-impaired brain needs a profound cleansing reminder. Focus is the entirey of my attention focused on one thing. This person, this meeting, this design.

But what about this other semi-related thing? Let’s wander in that direction…

No, all I am doing is this.

But you’re the people person. Read the room, Rands! What is the intriguing political dynamic of this particular group of humans? I wonder…

No, I am here to do one thing. The reason why I was invited was to participate.

But I’ve heard this story before, and he’s going to be talk talk talking for the next five minutes, so you know what I’m going to do? Just check Mastodon real quick. No one will know.

They won’t, but I will.

Thanks, ZackThere is a time and place where your primary job as a leader is sustained acquisition, synthesis, and redistribution of information. This practice is likely the majority of your career as a leader. More confusing, it’s a learned skill diametrically opposed to the skills you were rewarded for as an individual contributor.

But here’s why we must thank the hapless Zack for our gift — this douche who was nesting and vesting rather than building a team.

Focus, the pure focus on the task in front of you, is when you do your best work. The important achievements of information management are essential but immeasurable. When you focus, intensely focus, you can see the one thing that must be said, to discover the critical assumption that transforms good design to great and to most efficiently transform your years of experience into small, understandable, and unintentional lessons for those sitting right there… focusing with you.

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Our 63rd episode isn’t really about vigilantism but more about holding grudges.

Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes.

https://traffic.libsyn.com/rands/theimportantthing0063.mp3

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As a Henry Cavill super fan, I was extra crushed when I read that reports of his return to the role of Superman were no longer true. After much consideration, I am here to tell you why this is good news.

But let’s start with the bad news.

The DC Movie Universe is Garbage Fire PresentlyIt’s fashionable to rip on DC because it’s been a holistic cinematic disaster for, well, ever. There have been stunning individual movies over the years, but unlike the competition, the DC movie universe is a confusing mess, and DC has legendary characters.

You have the infinitely reinterpretable Batman. You have one of the earliest female superheroes in Wonder Woman. And you have the movie that kicked off that whole craze with Christopher Reeve’s Superman.

With all of these compelling assets, the DC movie universe is much less than the sum of its parts.

What’s the problem?

The Feige RulesThe moment I knew the Marvel Cinematic Universe (“MCU”) was taking it to the next level was in April 2014. Agents of Shield was on TV and drafting on the impressive success of the first Avengers movie. The Winter Soldier (Best MCU movie ever? Discuss) was released on April 4, 2014 date. In the following Agents of Shield episode, they incorporated Winter Soldier’s events into the TV series.

The marketing campaign at the time. “It’s all connected.” We’d never seen anything like it.

The DC movie universe is a disaster because they have not followed all of the Feige rules. They read:

For the good of all movies, you shall:

  • Honor the source material, but don’t be beholden to it.
  • Find new voices who bring new perspectives.
  • Always remember it’s all connected sensibly.

Kevin Feige (pronounced: FY-ghee) is a producer for Marvel. Well, he’s the producer for Marvel and has overseen all five phases of the MCU, including the first three phases, which are called “The Infinity Saga,” and the last two called the “Multiverse Saga.”

For the Infinity Saga, the Feige rules have been held. The first Thor is a wildly different movie than the first Iron Man. Different directors with diverse perspectives, but in each film, there was a reminder — usually a post-credit scene — that this universe was connected and was narratively rowing in the same direction.

The intense joy of the final Avengers Assemble scene at the end of End Game is a byproduct of firm adherence to the Feige Rules. As each character appears, we remember our unique relationship with them from their unique film, but the feeling is intensely multiplied by the fact they are here… together.

It’s all connected.

Back to the Garbage FireDC movies have spectacle. DC movies honor source material and also riff on the material. The most recent Robert Pattison Batman was a work of art. Emo Batman FTW! Joaquin Phoenix’s Joker sets itself apart and is barely a superhero movie. Attempts to stitch Joker into a larger universe felt forced and contrary to the film’s intent.

Before that, you have the masterwork of Christopher Nolan’s Batman Trilogy, the fresh perspective and historically compelling Wonder Woman (the first one, the second one was a disaster), and the goofy brutishness of an Aquaman who was no longer the butt of every DC superhero joke. (Aside: Do you want to see quality DC content? Check out the animation. Just wow.)

These movies stand independently, but the proper application of the Feige Rules have demonstrated to us that the audience can expect more. A meta-story with an eventual massive payoff where the final reveal is… everything together all at once.

Zach Snyder was tasked with this important work which eventually gave us The Justice League, but Snyder cares more about spectacle than narrative coherency. Also, he was the Director of many of these films, and an important part of the Feige Rules is they must be applied by an external human who is not motivated by one film but all of them. Bonus points if that human has little difficulty landing a coherent narrative. Watchmen? Dr. Manhattan is the villain? WTF?

The final nail in this narrative mess was the incessant demand for the Snyder Cut. The Whedon Cut was so stunningly unsatisfying we demanded a re-do. And they did it — only adding the narrative confusion.

This isn’t a narrative; this is a garbage fire burning from some of my favorite superheroes.

Firing Henry Cavill, Again & A WarningSmart and influential people care deeply about the DC universe, including The Rock, Dwayne Johnson. His belief? Start by bringing Superman back to this universe in his best form. It is reported that he and his team pushed hard to get Cavill back to DCU. You first saw it at the end of DC League of Super-Pets (meh) with the cameo of Black Adam, followed quickly by Cavill’s surprise cameo at the end of Black Adam (phenomenal) wearing the Man of Steel suit, sporting the spit curl, and PLAYING THE CHRISTOPHER REEVE SUPERMAN THEME OMFG LOSING MY MIND.

It was a scene designed to call back to everything I loved about Superman, but I am OK with Cavill getting fired… again. Why? It’s reported the Gunn-penned Superman movie will focus on the early years of Superman, so Cavill doesn’t make for good casting for a young Supes. More importantly, it’s a strong sign of what the new regime of James Gunn and Peter Safran is willing to sacrifice to upload the essential Feige rule:

For the good of all movies, you shall remember that it is all connected sensibly.1


  1. You’re right to be worried about the Multiverse Saga. It’s not following all of the Feige rules.

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First Circle: THE SLOPPY AND THE UNPREPARED Meetings start late and run over. Attendees have not read the pre-supplied material, so we spend most of the time answering questions we had already answered elsewhere. Second Circle: THE DISTRACTED Meetings where attendees are not paying attention to the meeting. They sit there on their phones and… More

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AirPods Pro. First, I told myself I’d only include one Apple product on this list, and this is it. Here’s how to sell this product to your friends. First, show them how to properly insert them in their ears (many folks do this incorrectly) and then have them turn on noise cancellation. Boom. Rapha Merino… More

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The almost immediate challenge with the introduction of the Internet presented was, “How do I find X?” Now, the actual first challenge was, “I wonder if X exists in this new world,” but that’s still “How do I find X?” This quest made search services the killer app of the Internet. AltaVista was a thing… More

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The Rands “R” started many years ago as this: I’ve been toying with branding, design, color, and other marketing elements for the site for years. I remember spending a couple of weekends trying to get a good picture of the weave of my favorite beanie as background for the site. That’d didn’t go well. I… More

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Level 1: NOT BUSY My schedule is wide open. I can choose infinite paths. Zero commitments. The weekend. I sleep like a baby. Life is good, but am I living my best life? Level 2: STUFF TO DO I have a few commitments wandering around my brain. They are reasonable, knowable, and not deadline-based. I… More

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I’m rewriting The Business for the next book. This piece is almost 15 years old, much has changed in negotiating an offer letter, and I have more advice on how to analyze those offers. So much advice that I am idea paralyzed™ trying to rewrite this piece. So, this is just a section of the… More

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Our 62nd episode is a little all over the place, but it works. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0062.mp3

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Our 61st episode discusses privacy on the Internet: why we need more education, how much your data is worth, and what parts of privacy need to change.  Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0061.mp3

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In our 60th episode, we talk about the ins and outs of jury duty. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0060.mp3

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In our 59th episode, we discuss why when you need to use the mice, there is a good chance you are failing. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0059.mp3

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For this piece, I am going to simplify management a bit. Let us assume there are three different hats you wear as a manager. They are: the Leader, the Fixer, and the Coach. I will briefly explain each role and then explain how I’ve screwed up each. I’m going in reverse order because I’m building… More

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Our 58th episode discusses the importance of numbers and their value in remembering things. It’s better than it reads. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0058.mp3

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In our 57th episode, we talk about how editing makes everything better. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0057.mp3

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In our 56th episode, we talk about Lyle’s recent month of podcasting adventures. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0056.mp3

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Elden Ring, developed by FromSoftware, wants you to rage quit the game. This is an undocumented feature of the game. You’re introduced to this feature promptly. After choosing your character, you’re plopped into a castle wondering Why is there no onboarding training? You walk through dark hallways reading warnings on the floor from other players.… More

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Frequently, I get a direct message from a community member on the Rands Leadership Slack pointing out a broken link on this weblog. I am happy to fix the link. I am not happy to reread what I wrote fourteen years ago because much of the early writing is… just awful. Unbearable, poorly punctuated, semi-coherent… More

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In our 55th episode, we return to familiar territory with special guest John Siracusa. The topic? Destiny 2 and why many, many years again, we continue to play every single day. Interested in our Destiny Slack? Figure out how to mail me, and I’ll send you an invite. Enjoy it now or download for later.… More

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In our 54th episode, we revisit the familiar theme of productivity and how we swear… this time… we figured it out! Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0054.mp3

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I am a short-form writer. A thousand words or so. Sometimes more, often less. I like to think I like tight prose and succinct thoughts, but I also know I’m impatient and have a short attention span. Over the years, familiar article structures and narrative flows have repeatedly crystallized into familiar templates. The most obvious… More

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First start-up. We’re between Layoff #2 and Layoff #3. There’s a new VP of Engineering running the show and while he’s been hired with the guidance to “turn the ship around,” the tech economy is a wreck and his first official act is throwing passengers overboard so we don’t sink. Now this will be the… More

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In our 53rd episode, we revisit the prior 52 episodes and talk about what we’ve learned. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0053.mp3

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In our 52nd episode, we discuss the question, “Can you effectively manage people doing jobs you don’t understand?” Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0052.mp3

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Each Slack team I’m on has a different set of humans building their own unique communication culture. I’m actively on six teams: Work, Leadership, Destiny, two private nerd Slacks, and a private family Slack. Three out of my six teams have 100+ active humans, 100+ channels, and are high traffic with hundreds to thousands of… More

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In our 51st episode, we discuss the importance of names… and pronouncing them. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0051.mp3

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Who is this? Princess Leia, right? End of Rogue One. Wrong, this is not Princess Leia. This is. A photograph of Carrie Fisher in her role of Princess Leia. Chances are, your brain can tell the difference between the two photos. The first is a computer generated image (“CGI”) and the second is a straight-up… More

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50 episodes later, we’re talking about the clothes on the floor. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0050.mp3

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In the rainy 49th episode, we discuss the weather and weather-related detritus.    Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0049.mp3

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In our 48th episode, we review the rich landscape of awesome media we’re currently consuming. Totally no spoilers. We swear. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0048.mp3

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In our 47th episode, we get stuck in a place of talking about doing things. Seems like a good episode to land at the beginning of the year. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or iTunes. https://traffic.libsyn.com/rands/theimportantthing0047.mp3

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The first book I purchased for myself. When I understood the science fiction genre. Getting beat up as a kid and how the marbles helped. My favorite pen. When I learned why typography mattered. Why I care about bears so much. Why Tribeca matters to me. When I was a kid, I had nightmares. Saying… More

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Just in time for Christmas, I’m happy to announce the 4th Edition of Managing Humans. It appears that four years is the sweet spot for new editions of this book. The process of getting this edition out the door was the least painful of the four unless you factor in, ya’know, the pandemic. Edition notes:… More

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Welcome back. In our 46th episode, we’re talking about the new shelves in the cave. They’re big. Like huge. It’s so good to be talking with you all again. Spend time with Lyle and Lopp talking about important things. Enjoy it now or download for later. Here’s a handy feed or subscribe via Overcast or… More

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Coming to the end of another complicated year. Each time I think we’re getting back to normal, something else horrible goes sideways. It’s wearing us all down. Over at the Rands Leadership Slack, we do an annual donation program where we ask those who are finding value in the community to make a donation to… More

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Imposter syndrome. It’s the feeling that pure happenstance or just dumb luck is the reason you’re in this current role. It’s a sense you don’t belong, you aren’t good enough, and – real soon now – everyone is going to see you for who you really are. You might have felt this before, and I’m… More