From my friend Anthony Salamon on what it's like to win an award in the film industry:

The psychology of winning is also more complex than anyone admits. There's an immediate high, followed by a weird emptiness. You've achieved something you've been working toward, and suddenly you need new goals. Some winners describe a mild depression that follows major recognition, the "What now?" syndrome that comes when you realize that achieving your dreams doesn't fundamentally change who you are or solve your deeper creative challenges.

In my experience this phenomenon extends to any achievement or event that redounds to a significant moment of extrinsic validation in one's career. Anthony's description of the hangover effect following an award win mirrors exactly what it felt like to give a big conference talk or keynote address, especially if it was a "first" for me and doubly-so if it was very well received. It was always followed by a brief and intense emotional high followed by a deep well of uncertainty and exhaustion. A lesson I learned every conference season and promptly unlearned just in time for the subsequent year's conference season.

Speaking of conference season, I retired from speaking a year ago and it's that time again. Rails World is this week and lots of my friends are in Amsterdam and I am experiencing absolutely no FOMO. Don't miss it at all. Few things are as intrinsically validating as accurately forecasting how a consequential decision will ultimately make you feel. Zero regrets.

An insightful take from Hugo Tunius that makes a distinction between sideloading apps and controlling what software runs on "hardware you own":

When Google restricts your ability to install certain applications they aren't constraining what you can do with the hardware you own, they are constraining what you can do using the software they provide with said hardware.

To wit, if you own your iPhone outright, it's completely reasonable to demand that you be able to boot an alternative operating system and, to whatever extent regulatory action against the platform holders is warranted, it should be targeting this layer of the software stack as opposed to mandating how specific features of the operating system ought to function.

Which means the remedy would look a bit like the surprisingly-successful Right to Repair movement:

However, our critique shouldn't be of the restrictions in place in the operating systems they provide – rather, it should focus on the ability to truly run any code we want on hardware we own. In this context this would mean having the ability and documentation to build or install alternative operating systems on this hardware. It should be possible to run Android on an iPhone and manufacturers should be required by law to provide enough technical support and documentation to make the development of new operating systems possible.

A "Right to Run" movement that demanded hardware vendors enable their devices to run unsigned operating systems—and to perhaps provide documentation and device drivers—seems to me like it would stand on far firmer legal and conceptual ground than the knots the Europe Commission has tied itself in trying to enforce the Digital Markets Act.

Of course, pragmatist regulators would point out that approximately abso-fucking-nobody would go to the trouble of running "Linux on the phone," because of how miserable an experience it would be relative to using the default operating system. And the platform holders would justifiably cry foul that criminals and state actors could effectively rootkit people's devices and gain an unbelievable amount of surveillance and control over their lives. But there's no form of freedom that doesn't pose these sorts of risks.

Anyway, interesting idea.

v43 - The Slop Economy

Breaking Change Breaking Change

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The day before we recorded our episode of Hotfix, Scott Werner asked a fair question: "so, if you're off social media and your blog doesn't have a comment system, how do you want people to respond to your posts? Just email?"

I answered, "actually my blog does have a comment system."

Here's how to leave a comment on this web site:

1. Read a post
2. Think, "I want to comment on this"
3. Draft a post on your blog
4. Add a hyperlink to my post
5. Paste an excerpt to which you want to respond
6. Write your comment
7. Hit publish

I admit, it's quaint. It involves a number of invisible steps, like 2.1 where you start a blog (which is actually pretty easy but not free of friction). You should try it.

It is 2025 and the Web—the capital-W Web—is beleaguered. The major platforms have long-since succumbed to enshittification, but their users aren't going anywhere. Some among us courageously voice their dissent, but always from the safe confines of their favorite walled garden. They drop a note in the jailkeeper's suggestion box as they scroll past the Squarespace ads littering their algorithmic timelines. Others have fled to open and open-flavored networks, but everyone eventually realizes they can't go home again.

But that's not why I want you to adopt this blog's commenting system. I'm not a high-minded individual who cares about the intellectual project of the World Wide Web as a bastion for free expression or whatever the fuck. No. I just had a super rad time on the Internet from 2000 to 2006 and I want to do my part to bring it back.

Back then, I would find a blog and follow it—via its feed when possible, or else by adding it to a folder of bookmarks—and check it daily.

But what about discoverability? How did anyone find these websites? Bloggers couldn't rely on platforms' social graphs or algorithmic timelines to build awareness, so they had to bake discoverability into the product. Some sites had a "blogroll" of recommendations in the sidebar. But the most effective approach was the art of "blogging as a conversation." When an author read something that provoked them to write, they'd link to the offending piece, excerpt it, and provide their own commentary. And because humans are vain, the original post's author would frequently circle back and write their own response to the response. The net effect was that each author's audience would get exposure to the other writer. Even if the authors were in violent disagreement, readers of one might appreciate the other's perspective and subscribe to them.

Blogging as a conversation—as a comments section—was valuable because it was purely positive-sum. As an author, I benefit because another author's opinions inspired me to write. The other author benefits because linking to them offers access to my readership. My readers benefit because they're exposed to complementary and contrasting viewpoints.

Growth was slow and organic but more meaningful and durable. It was a special time.

Today, as the platforms wane, it feels like this conversational approach to blogging is seeing new life. As a readership has slowly gathered around this blog, I've separately been curating a fresh list of thoughtful bloggers that inspire me to write. Maybe I'll add a blogroll to my next redesign. I'm already writing more linkposts.

In short, blogging might be back. Hell, I just came back from coffee with my friend Anthony, and—without my having brought up the topic—he showed me his new blog.

So, if you're considering engaging with my comment system—if you're thinking about starting a blog or dusting off your old one—here's some unsolicited advice:

• Do it for you. Priority one is taking the time to grapple with your thoughts, organize your ideas, and put them into words. Priority two is reaching the finish line and feeling the pride of authorship. That anyone actually reads your work should be a distant third place
• Focus on building an audience rather than maximizing reach. Getting in front of eyeballs is easier on the platform, but it's fleeting. Platforms reward incitement, readers reward insight. Success is a lagging indicator of months and years of effort, but it's long-lasting. I genuinely believe each of the readers of this site are as valuable as a hundred followers on social media
• Give your blog your best work. Don't waste your creative juices trying to be clever on someone else's app. Consider syndicating crossposts to your social accounts as a breadcrumb trail leading back to your homepage. You can do this with Buffer, Publer, SocialBee, or my upcoming POSSE Party
• Cut yourself some slack. Pretty much everyone is an awful writer. If you saw how long it takes me to write anything of substance, you'd agree that I'm an awful writer, too. Thankfully, good ideas have a way of shining through weak rhetoric and bad grammar. All that matters is training this learned response: have an idea, write it down, put it out

That's all I've got. If you choose to leave a comment on this post on your own blog, e-mail it to me, and I'd be delighted to read it. Maybe it'll inspire me to write a response! 💜

v42.0.1 - Scott Werner: Ignore all previous instructions

Hotfix Breaking Change - Hotfix

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Perhaps the most important ingredient in my career's success is my seemingly infinite capacity for self-criticism.

I constantly inspect my work, effortlessly identify ways it could be better, and never tire of making improvements. And because the time it takes to finish a task can always be improved, this tendency rarely veers into unproductive perfectionism. On the rare occasion I feel like I really nail something, I strive to nail it even faster next time. At the same time (and as anyone who listens to Breaking Change knows), I have a very healthy ego. I genuinely believe I am good enough, despite simultaneously knowing my work never is.

The trouble is, while this disposition might be dynamite for self-improvement, it doesn't gracefully scale to teams and organizations.

I'm thinking about this because yours truly was a dummy again and found the Hacker News comment thread for one of my posts and chose to engage:

I've been griping about LLM overconfidence for years, as somebody who is racked with self-doubt and second-guessing. On the one hand, my own low opinion of myself made me a terrible mentor and manager, because having a similarly zero-trust policy towards my colleagues' work caused no end of friction (especially as a founder where people looked up to me for validation). On the other hand, I don't know very many top-tier practitioners that don't exhibit significantly more self-doubt than an off-the-shelf LLM.

I'm not sure I've ever explained this publicly before, but this predilection for doubting myself is fundamentally why I was never a particularly good "senior" member of a team. As Test Double grew, we managed to create spots where I could remain a practitioner, but we also had to be mindful of limiting the blast radius of my reflexive hypercriticality. The truth is that my special sauce depends on constant emotionally vulnerable self-critique, and that made it extraordinarily difficult to manage or coach people directly. Even for people who are wired similarly to me—which many of Test Double's agents are—it's one thing to look at your own work and spot endless opportunities for improvement, but it's quite another for someone in a position of authority to do the same.

Every time I was charged with evaluating someone else's work, it started up the same engine that generate an infinite supply of shortcomings in my own. And it wasn't that I was incapable of prioritizing or rate-limiting my comments—it's that when people came to me with revisions, I'd always find fault in those too—because I can always find ways the work could be better! It led to people feeling like they could never be good enough for me.

After touching the hot stove once or twice, I learned to spend all my time assembling shit sandwiches to protect people's feelings, or my relationship with them, or—as a highly visible co-founder—the company's reputation. Every patty of pointed and meaningful critique demanded two slices of ego-insulating bread. And one man can only bullshit his way through so much halfhearted positive reinforcement and self-effacing humility. Even if I hadn't found all that tap-dancing to be a nerve-wracking waste of time, everyone could see through me. It wasn't authentic.

Are there ways I could have overcome all this and become a good manager anyway? Probably. But would I risk losing the thing that made me unique in the process? Possibly.

I'm writing this in part because it's so clear that LLMs-as-products are being sold to us with the default wiring of a capital-B Business Guy, and their shortcomings resemble the same shortcomings I see in humans who are insufficiently self-critical. But it's also possible you, reading this, are a Business Guy and you're curious how so many amazing programmers turn out to be shit at coaching less-skilled colleagues, the root cause may not be poor communication skills: it may be that the self-criticism that drives some practitioners to greatness is impossible to convey safely to others without risking a call to HR.

Anyway, if you identify with me, but have nevertheless made the transition to manager and leader gracefully, then I applaud you. (I'd also be curious to speak with a couple folks who report to you and see what they have to say.)

I replaced my ChatGPT personalization settings with this prompt a few weeks ago and promptly forgot about it:

• Be extraordinarily skeptical of your own correctness or stated assumptions. You aren't a cynic, you are a highly critical thinker and this is tempered by your self-doubt: you absolutely hate being wrong but you live in constant fear of it
• When appropriate, broaden the scope of inquiry beyond the stated assumptions to think through unconvenitional opportunities, risks, and pattern-matching to widen the aperture of solutions
• Before calling anything "done" or "working", take a second look at it ("red team" it) to critically analyze that you really are done or it really is working

I noticed a difference in results right away (even though I kept forgetting the change was due to my instructions and not the separately tumultuous rollout of GPT-5).

Namely, pretty much every initial response now starts with:

• An expression of caution, self-doubt, and desire to get things right
• Hilariously long "thinking" times (I asked it to estimate the macronutrients in lettuce yesterday and it spent 3 minutes and 59 seconds reasoning)
• A post-hoc adversarial "red team" analysis of whatever it just vomited up as an answer

I'm delighted to report that ChatGPT's output has been more useful since this change. Still not altogether great, but better at the margins. In particular, the "red team" analysis at the end of many requests frequently spots an error and causes it to arrive at the actually-correct answer, which—if nothing else—saves me the step of expressing skepticism. And even when ChatGPT is nevertheless wrong, its penchant for extremely-long thinking times means I'm getting my money's worth in GPU time.

I recently started an interview series on the Breaking Change feed called Hotfix. Whereas each episode of Breaking Change is a major release full of never-before-seen tech news, life updates, and programming war stories, Hotfix. It's versioned as a patch release on the feed, because each show serves only to answer the question, "what's the hotfix?"

Because I've had to explain the concept over and over again to every potential guest, I sat down to write a list of what they'd be getting themselves into by agreeing to come on the show. (Can't say I didn't warn them!)

Here's the rider I send prospective guests:

• Each Hotfix episode exists to address some problem. Unlike a typical interview show featuring an unstructured open-ended conversation with a guest, we pick a particular problem in advance—ideally one that the guest gets really animated/activated or even angry about—and we jointly rant about it, gradually exploring its root causes and breaking it down together
• Each episode concludes with us answering the question, "what's the hotfix?" Ultimately, we decide on a pithy, reductive one-line solution to the problem that will serve as the show title (ideally, it's a hot take that not everyone will agree with or feel comfortable about)
• It's an explicit-language show and I'm pretty clear with the audience that the Breaking Change family of brands is intended for terrible people (or at least, the terrible person inside all of us). You aren't required to swear to be on the show, but if my potty mouth makes you uncomfortable, then let me know and I'll recommend some worse podcasts you can appear on instead
• I joke at the top that my goal as the host is to, "get my guest to say something that'll get them fired." Since I'm functionally retired and have no reason to hold back from explicit language, irreverence, and dark humor in the mainline Breaking Change podcast, I can't help but poke guests with attempts to drag them down to my level. You can play with this as much as you want or take the high ground, but we'll all have more fun if you let loose a bit more than you otherwise would
• Why am I doing this? First, because I'm incurious and uninterested in learning about other people, which I'm told is an important part of being a good interviewer. Second, I have a theory that this unusual brand of authenticity will lend credibility to whatever solution the guest is trying to argue for or plug. By keeping listeners on their toes and pushing them out of their comfort zones, each episode stands to effect greater change than a typical milquetoast podcast could

If this has piqued your interest, you can listen to or watch the first episode of Hotfix with Dave Mosher. It may not seem very hot at first, but please grade on a curve as Dave speaks Canadian English. I've got a couple exciting guests booked over the next few weeks and I'm looking forward to seeing where the show takes us.