Systems

  • August 14, 2025

    My D.A.D. Framework for Overwhelmed Solopreneurs

    One of my favorite lines in 30 Rock, a show full of one-liners, is uttered by Jack Donaghy, Alec Baldwin’s character:

    I’m the Sisyphus of Reaganing.

    Reaganing, in the show, is where you have a day where you make no mistakes. It’s the “perfect game” of business.

    It’s a deep joke. You need to know a little bit about US politics during that time. You also need to know who Sisyphus is.

    Sisyphus, if you don’t know, was condemned to pushing a boulder up a hill, just to have it roll back down, after a life of hubris in which he tried to cheat death.

    Futile labor, for all eternity.

    Don’t you kind of feel like that running a business sometimes?

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  • July 23, 2025

    Why I’m Trading Highlights for Voice Notes

    “What if I need it?”

    This is the justification for keeping anything you haven’t used in a long time.

    It could be mail, books, kitchenware, clothes, or anything else you’ve accumulated over time.

    For me, it’s cables. I have cables that would be completely unrecognizable to my kids. Heck…I have cables my wife probably never used. Because…”What if I need it?”

    Most other stuff I’m fine getting rid of — almost to a fault. I’ve overzealously thrown out things that were still very much needed, but that weren’t in use the day I got sick of the clutter.

    Clutter in the physical space drives me crazy. But clutter in the digital world…I almost never see that.

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  • July 17, 2025

    I made the mistake of trying to do it myself

    There are some things you can DIY well enough by watching a YouTube video or reading instructions.

    Smaller home improvement projects fall under this category. Over the weekend, I was able to rewire our new smoke alarm without shocking myself, for example.

    I was very proud of myself.

    There are some things you could probably manage doing yourself, but it’s far better if you hire a professional.

    Editing your own podcast and YouTube videos lands here. The time you spend for the quality you get isn’t worth it for most people.

    Back in the home improvement realm, we recently got a new smart lock, but I realized our exterior door doesn’t have a deadbolt, so we need to add one.

    I could probably do this myself…but the time/quality factor isn’t worth it. It will take me much longer, I’ll have to buy the right tools, and if I mess it up, we’ll need to get a new door.

    Then there are things you definitely shouldn’t do yourself. Replacing your roof if you’re not a roofer, or installing a new HVAC system.

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  • July 15, 2025

    How Bad Defense Ruins Even the Best Teams—and Businesses

    Long-time readers will know I’m a big baseball fan. I think it’s a great sport, and I find a lot of inspiration from it.

    And not always good inspiration.

    My favorite team, the New York Yankees, entered June in 1st place, leading by 5.5 games. That’s a pretty healthy lead.

    But injuries started creeping in, players got shuffled around, and now they’re in 2nd place, behind the Blue Jays a little more than halfway through the season.

    What’s most interesting is that it wasn’t their offense that failed them.

    They consistently scored five or more runs per game (20/38 games, starting from June 1), which should typically be enough to win.

    So why did they have a record of 18 wins and 19 losses? The issues ran deeper.

    The issues ran deeper.

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  • July 10, 2025

    How I Let AI Ruin My Podcast Content Strategy

    On Monday, I wrote about spending your time wisely; I don’t think I’ve been doing that with my podcast.

    I’ve been more focused on “parking lot” stuff, to use the analogy from that newsletter:

    1. Episode numbers
    2. Making sure the YouTube playlist has perfect parity with the audio feed
    3. Whether or not my audio notes should be their own feed or part of the main show
    4. Should I put my shorts on the podcast YouTube channel or my main channel?
    5. Should I even have a separate YouTube channel for the podcast?

    It’s perhaps stuff that I should think about over the long term.

    But it doesn’t solve my immediate problem, which is that my downloads are way down.

    So what should I be focusing on? I’ll give you a hint: It’s not tactics.

    In 2018, Seth Godin said podcasting is the generous act of showing up.

    And while his last book is the worst business book I’ve ever started to read, he’s still right about this.

    Reflecting on this got me thinking, “Have I been showing up in the best way?”

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  • July 8, 2025

    The Parking Lot Problem: Why You’re Focusing on the Wrong Things in Your Business

    I was looking at a new karate studio that opened up in my town and I couldn’t help but think that there were very few parking spots for people to park…like 8 at most.

    What would happen if one of the classes got too big? Where would people park? Are there more spots in the back?

    Why haven’t they thought about this?

    I realized that the people who opened the studio were probably more concerned about the most important parts of their business:

    • Making a good space inside the studio
    • Hiring good instructors
    • Getting the right insurance

    …and all sorts of other aspects of the business that had nothing to do with where cars will park.

    That’s a secondary problem. They found a great space where they could open a karate studio; if they suddenly had a parking problem, they’d figure it out.

    I don’t run a physical space, but I know I can learn a lot from this.

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  • June 26, 2025

    Why “Just Ask AI to Code It” Doesn’t Work

    Back when I was a web developer, every week a friend or acquaintance would come up to me and say, “Joey, I have a great idea for an app.”

    They would then explain some brilliant app to me that would make a ton of money. I’d patiently listen, then ask them 4 questions:

    • Who would use this app?
    • How will it make money?
    • What competition is out there?
    • What do you see as the partnership for this app?

    Ultimately, they’d say:

    • “Everyone”
    • “I don’t know yet but it will”
    • “There is none”
    • “I was thinking 50-50”

    …which were all terrible answers to those questions. Mostly because it showed they did zero work outside of having the idea.

    And partially because 50% for an idea wasn’t exactly my favorite business model. Even if it was 50% of nothing.

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  • June 22, 2025

    Trying superwhisper as my Voice Notes App

    I’m trying a new voice notes app.

    I’ve used Whisper Memos for a while now, and really, truly loved it. But the last four or five notes I’ve tried recording with it were completely lost. No transcript, no recording, no summary.

    When I rely so heavily on a tool that becomes this unreliable, it’s time to move on. So after a brief stint with Whisper Transcription, I’ve decided to look at superwhisper.

  • May 28, 2025

    Vision, Workflow, Purpose: Lessons from Watching 13 Movies in 4 Days

    When I was a kid, the flu hit me extraordinarily hard. I was down for 2 weeks. I couldn’t eat. I slept poorly. I got way behind on school work.

    I did lose like 15 pounds, though.

    Due to diligently getting my flu vaccine every year since, I haven’t really gotten the flu, let alone as bad as I did.

    Until last week.

    The flu is going around the county, including at my kids’ school. So when my daughter came home with a 103°F fever, I knew it was only a matter of time for me.

    By Thursday, I was feeling pretty rotten; rotten enough to go to urgent care over the weekend for fear of pneumonia or something worse.

    Thankfully, it was “just” the flu.

    So I had a lot of time on my hands. And I decided to watch a bunch of movies — 13, to be exact.

    • The Original Star Wars Trilogy
    • The Star Wars Prequel Trilogy
    • Every movie featuring Chris Evans’ Captain America (The first Captain America Trilogy, plus the first four Avengers movies).

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  • May 14, 2025

    The Intentional Vacation: How My Systems Delivered True Family Time

    I’m back from our family Disney Vacation and there’s a lot to be happy about.

    My kids were troopers — Casabona vacations are not very relaxing. Out of the hotel early, back late. Long, hot days.

    They handled it well and had a lot of fun. We made some great memories.

    And I’m happy to report that I was fully present for all of it.

    This may seem like a silly statement. “Of course you were present…you were part of the vacation.”

    But before the trip, I wrote about everything I did to prepare for not working at all while down in Florida.

    It totally worked.

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