Searls of Wisdom for June 2025

Greetings everyone, and welcome to the middle of July in Orlando, where it's too damn hot outside and too damn cold inside. Thank you for joining our Q2 Performance Review of the Justin Business Unit at Searls LLC. Before I share status updates on this year's strategic initiatives and dig into how we're tracking against our KPI benchmarks, here are a few highlights regarding our output over the past month:

• The latest pre-release build of POSSE Party adds support for four new platform integrations, a 200% increase over the previous version
• I started a new interview series on called Hotfix on the Breaking Change feed, and its inaugural episode is getting rave reviews. When you factor in March's launch of Merge Commits, podcast series are up 300% compared to the year-ago quarter
• "Full-breadth Developers" generated tens of thousands of organic impressions in its first 24 hours of publication, marking the fastest growth of a buzzword-defining post in justin.searls.co history
• Speaking of the website, a new suite of automations has been implemented that add support for scheduling posts in the future, fetching social images for outbound links, normalizing typographical inconsistencies, and pissing off most of my followers by spewing an endless stream of my Japanese restaurant reviews

There were some bittersweet notes this month, as well. The Walt Disney Company decided to conclude its partnership with Searls LLC with the closure of Tom Sawyer Island, ending a 16-year tradition of my posing in front of the name "Tom" on this fence:

What's with all this corporate year-in-review stuff? Well, Becky's latest podcast prompted me to consider doing my own, "6 months down, 6 to go," retrospective on 2025. This is me leaning in.

The verdict is in, and I've decided to give myself a failing grade.

Why I haven't started yet

Autonomy may not be all it's cracked up to be.

Over two years ago, I found myself consumed by a flood of ideas for an ambitious app to support my lifelong pursuit of acquiring a second language. These ideas emerged from years and years of struggle to learn everyday Japanese. In mid-2023, I reached the point where it was the only thing I wanted to work on. Here we are in mid-2025, and I'm still at that point. That is, of wanting to work on it.

I haven't started yet.

Today, I'm going to play back the tape and try to figure out where I went wrong.

756 days ago. I asked my co-founder Todd Kaufman for a meeting to discuss my desire to step back from day-to-day operations at Test Double and pursue a vision for building an AI-enhanced app for learning a second language. He was, as always, incredibly supportive. We mapped out a plan to transition my responsibilities to others by the end of the year.

562 days ago. I formally ended my career as a full-time employee of the company I had co-founded at 26 (I was 38 by then). I felt optimistic about dedicating myself fully to building this thing, but it was tempered by the knowledge that I'd have no one to blame but myself if it didn't happen. Deep down, a part of me—and I suspect, a part of all of us—found a secret comfort in being able to point to extrinsic factors (other people, responsibilities, circumstances) as a potential excuse for failing to do whatever we claimed to be most important. After quitting my job, the only immediately observable change was the loss of that excuse.

569 days ago. As if to prove the above point, a week before my last official day as an employee, I made my first commit to the project that would eventually power my wife's business, Better with Becky. I started with a public-facing blog called Beckygram and then extended it to deliver her strength-training programs as a subscription product. It was a massive undertaking, but I told myself there wasn't much point in freeing myself from the daily grind if my spouse was still chained to a desk, manually assembling Google Docs and Sheets for her subscribers.

552 days ago. I started an explicit-language podcast for some fucking reason. I guess no longer having several hours of Zoom meetings to look forward to every week made me feel the need to get things off my chest some other way. Don't get me wrong, I really enjoy Breaking Change and the audience it's finding, but I am endlessly frustrated by the fact that recording a three-hour show takes three whole hours. That's too much time!

310 days ago. We (finally) launched the first Build with Becky strength-training program to subscribers via the new member portal. It took longer than I hoped to get the app over the finish line, but that's how it always goes. I enjoyed a moment of relief as I imagined being able to switch gears to pursue my own ambitions.

292 days ago. Just kidding, because several months prior I'd separately agreed to give a presentation about building SaaS apps as a solo developer at the second annual Rails World conference. Naturally, given how obsessive I am about crafting presentations, I worked day and night to perfect my slide deck right up until showtime. I was so exhausted by the end of it that I decided the only way to prevent myself from repeating the same mistake was to publicly announce my retirement from speaking live on stage. Life's too short to spend two months of every year tweaking slides in Keynote to produce a 30-minute presentation.

249 days ago. The worst part about launching a product is that people might pay for it and develop their own opinions about how it should be "fixed." While I'm proud to say that—by my definition, at least—the Better with Becky software platform shipped with only two Actual Bugs, it was almost two months before the dust had fully settled and I'd addressed all the feedback from its initial subscribers. I still bear the perpetual monthly burden of updating its dependencies, but beyond that chore I was well and truly done. I could finally buckle down and break ground on this language-learning app, nearly a year after quitting my day job.

246 days ago. But first, we needed a break. So Becky and I departed for a mostly-computer-free vacation in Japan. We spent a few weeks road-tripping to famous leaf peeping locales and scouting cities I'd identified as potential places we might like to live someday. Incidentally, we made an unplanned pit stop in Shizuoka City on our way to someplace else, and that's where we eventually wound up buying a vacation home.

223 days ago. We got home from Japan, recharged and ready to take on what's next. For real this time, I was going to finally install Xcode and start building this app. My mind was buzzing with ideas after spending several weeks criss-crossing the country and finding new ways to suck at Japanese. I started a fresh notebook and quickly filled it with architecture diagrams and UI sketches.

212 days ago. My dad passed away.

187 days ago. After we'd returned home following the funeral and settled back into our routine, I scanned my to-do list for a software project that would feel like a quick win. I'd lost my appetite for ambitious endeavors. I craved the productivity equivalent of comfort food. Something I could build using familiar technologies, doing things I'd previously proven out elsewhere. That's how I embarked on building a single app to replace the assortment of ramshackle tools I'd assembled to syndicate my content from justin.searls.co to my various social media accounts.

141 days ago. Even though I'd already built a working version of the app that could have sufficiently met my needs, I wasn't ready to move on just yet. I registered a domain name and announced this syndication project as a product with a splash page and a waitlist and everything. I justified giving it precedence over the language-learning app by saying I wanted to put to bed the problem of content distribution so that I could more widely share a development diary which would document my journey into the world of designing native apps for Apple's platforms.

75 days ago. I boarded a plane to convince a real estate developer to sell me a condo. As luck would have it, achieving this took a month of near-full-time effort.

48 days ago. Despite announcing POSSE Party as if it would be a traditionally-hosted SaaS product, I decided I was unwilling to operate the app as a going concern. Witnessing firsthand how often these social media integrations break, I simply could not imagine running a business whose operation depended on the platforms' unreliable, semi-abandoned APIs. I spent five minutes imagining being responsible for a support@posseparty.com inbox and immediately noped out. (If anyone wants to buy a gently-used, pre-launch SaaS app, let me know.)

8 days ago. After a series of really positive experiences putting what I hoped would be the finishing touches on POSSE Party by leveraging AI agents to write all the code, I wrote a thinkpiece nobody asked for, started a new interview show to discuss it, and got underway building a CLI tool for onboarding Claude Code into existing software projects.

0 days ago. I finally acknowledged that I've lost all control of my life.

I taught Becky the phrase yak shaving last year at some point, and she takes joy in searching for opportunities to use it. Try this one on:

• I'm currently building a tool to make it easier to adopt AI coding agents, because…
• I wrote a post advocating for software developers to reckon with the sea change currently underway, because…
• I started using AI agents myself in a rush to finish an app that wasn't worth my own time and effort, because…
• I refused to stand behind and support a product that could break for reasons totally outside my control, because…
• I realized I'd been laboring under the mistaken notion that maximizing the reach of my content was more important than the work itself, because…
• My dad had just died, and I lacked the courage to risk failing and losing something else I really cared about

So, here I am, six levels down the stack, wondering where this year has gone. And that's just one series of distractions I've become mired in—if we had the time, I could share others!

Anyway, it's now mid-July and I'm ready to admit that my 2025 Strategic Plan is decidedly off course.

I thought it might be useful to write all this, if only because I'm probably more retired than you are. So, in case you might be harboring the same delusions I was: if you think you know exactly what you'd do tomorrow if you were to quit your job today, you're very likely wrong. We all live in prisons of our own design, and it's worth pondering whether being liberated from all constraints would result in true freedom or in the installation of new constraints.

I'm as ruthlessly disciplined as anyone I know, and time after time I've failed to take a single step forward toward my own purported goal in over 18 months. Why not? Why doesn't matter. The only thing that separates a valid reason from a flimsy excuse is the subjective value we assign it. The end result is the same: it hasn't happened yet.

Even now, as I type this, I have no faith it'll be enough to convince me to do anything differently tomorrow—we've got contractors coming to fix the fridge, seal the pavers, and replace a few toilets, after all.