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Searls of Wisdom for August 2025

Hope you're having a lovely September so far. Hard to believe it's almost Fall! Always love seeing the first signs of the end of Summer—I refer, of course, to Apple's annual iPhone event.

In case you don't subscribe to my every waking moment, some highlights of stuff I put out over the last month:

Every month, I scroll through the last month of photos for one to include in this newsletter. Not many pictures this month, so here's a little surprise Becky left me that showed up in our iCloud Shared Photo Library

How dare you assume this coaster saying that I add liquor to my protein shakes is true even though it is

I feel personally attacked. And thirsty.

Today, I'm writing you about my favorite topic: capitalism. Or, more specifically, I'm here to shed a little light on a few "special" kinds of people who tend to be highly-valued in the economy but who are often portrayed as stereotypical caricatures. Each is as stubbornly human as the rest of us. Each possess an unusual blend of attributes that make them well-suited for the current epoch. My consulting career brought me face-to-face with more than my fair share of these people. The experiences I reflected back on while writing this were sometimes interesting, sometimes impressive, and rarely both.

Forced to categorize the most impactful people I've observed and encountered at work, I'd break it down into three archetypes: visionaries, entrepreneurs, and innovators. Each persona combines tremendous capability with comparatively bewildering blind spots. The business world holds these folks up as paragons of Employee Virtue. Not because they are perfect, but because their unique traits—when harnessed appropriately—can produce unparalleled results. And because the people doing the hiring always have faith in their own ability to harness the people they hire, candidates who fit these molds are often hired on the spot, bypassing any standard process. Most employees are employed by a business, whereas these employees happen to a business.

Visionaries

Investors can't resist the siren song of visionary leaders who are preoccupied with growth. Visionaries want to achieve massive scale, can sustain obsession over decades, and believe in their own ability to change the world. Remember how Steve Jobs said he wanted to make a dent in the universe? That's the vibe. Audacious founders armed only with a half-cocked idea and delusions of grandeur have raised more in funding than you or I will earn from a lifetime of productive labor.

Beyond Wall Street, the general public also valorizes the growth-obsessed, because visionaries' irrational optimism reads as endearingly plucky in an underdog. But once that dog catches the car and begins to steer it from behind, those same traits become terrifying for us as passengers. To wit, you probably feel differently about Zuckerberg, Bezos, and Musk today than when you first learned about them. But the billionaires haven't changed at all. Our perspective of them is what shifted. They merely represent the natural end game for people wired to believe that more is never enough.

Of course, hating the ultra wealthy is nothing new. More recent, though, is a prevailing suspicion of growth for growth's sake, especially as the externalities of unregulated growth are becoming harder to avoid. My former colleague and mentor Daryl Kulak would often counter clients pushing for unrestrained growth with, "we actually have a word for something that grows forever: cancer." As much as the economy might love those with an unbridled ambition to grow, the rest of us can pretty easily spot the downsides. And while every visionary's light shines brightly, most are inevitably snuffed out—there's only room for so many winners.

Entrepreneurs

Think of a world-renowned business. Any business, doesn't matter which. That business would have ceased operations long before you'd ever heard of it were it not for some number of entrepreneurial employees predisposed to action over deliberation. When an issue arises, they add it to their plate. When someone else drops a ball, they can be counted on to catch it. When others deliberate endlessly, or stick their head in the sand, or waste time playing the blame game, they get shit done. They're sharks: if they stop moving, they die.

The action-oriented are not constrained by the bullet points on their job description. Hell, they probably hadn't finished reading the job description before picking up the phone and asking for the job. People driven to action make for appealing candidates not because they're confident "alpha" types per se, but because they talk in terms of what they will actually do to solve a problem as opposed to how they'll merely think, plan, or coordinate their way through it. Small businesses need them, because there's always far more shit to do than they can deal with. Large businesses need them, because their calcified bureaucracies prevent anything getting done otherwise. Struggling to visualize these people? Think of the guy who says, "ask forgiveness not permission," but who—come to think of it—has never actually apologized to anyone.

Of course, it's possible to over-index on action. There are plenty of times when the best course of action is to take no action at all. (Unsurprisingly, entrepreneurs tend to get trapped in the urgent half of the priority matrix.) Large and novel problems often demand mindful introspection, time-consuming research, and careful deliberation—none of which come naturally to someone wired to equate the size of a problem with its urgency. Beyond being prone to strategic myopia, entrepreneurs can struggle to delegate effectively. For example, suppose you hire somebody to do something you've been doing for years. Naturally, they'll have less experience and they'll be slower and worse than you at first. But patience and failure are anathema to most entrepreneurs. It takes every ounce of energy to stop themselves from grabbing the steering wheel the moment anyone takes a wrong turn. And when they do grab the wheel, the new hire does learn something: stay in your lane and out of that guy's way. Don't think for yourself. Defer decision-making to the boss. Hyper-productive people often complain that nobody else ever picks up the slack, but their own behavior is usually to blame.

Innovators

Another word that can make you a lot of money is innovation. People with an insatiable creative drive are always in demand, because there will always be new problems to solve and opportunities to seize. In this sense, "innovative" means more than throwing out a good idea in meetings every now and then. Innovators represent a fusion of creativity, proficiency, and pragmatism. There are plenty of incredibly-skilled creatives out there who don't build stuff. And there are plenty of highly-motivated builders who aren't the least bit creative. But when you combine all three elements, watch out.

The most innovative people I've worked with were absolute pains in the ass to deal with in the moment, and generally only appreciated by their colleagues in the past tense. That's because it would never cross the mind of an innovator to pay an ounce of respect to whatever plan is handed them. They bristle at any line of reasoning that doesn't perfectly mirror their own, and adamantly refuse to take a single step down a path they believe to be wrong. They stubbornly push back until they get a satisfactory answer to a thousand "Why" questions, with notably less interest in "Who," "What," "When," and "Where." As soon as they grasp the bigger picture, they run off in a direction of their own choosing. They can be wonderful collaborators to whoever is willing to get on board—and better to just go along with them, as they tend to out-hustle and outflank everyone else.

But by constantly coloring outside the lines, innovators are frequently seen as agitants. They disrupt the calm of their colleagues. Few organizations know how to incorporate itinerant change agents—the value they provide isn't well captured by most annual review rubrics. But sometimes, innovators manage to overcome this and capture lightning in a bottle and accomplish something nobody thought possible. And success seems to do a funny thing to people's memory, as everyone else is suddenly quick to brag and share war stories of working with them.

Innovators may lack as many telltale character flaws, but many share the same blind spot: whatever they're building, they don't care about the thing itself. That's because they're not in it for the outcome, they're chasing an experience—the practice of creating something no one has ever seen before. Lost in the act of creation, their relentless drive makes them like unguided missiles, ones that leaders can aim at whatever target they wish. In the early 2010s, I had the opportunity to grill engineers working at companies like Lyft, Airbnb, and GrubHub about the potential downstream harms their apps might eventually wreak. I never stopped being surprised at how little any of them had ever thought of it. The real-world impact of their work, good or bad, simply wasn't the point.

The Innovator's Other Dilemma

Of the three, I identify most as an innovator. It surprises people, but I've genuinely never cared about a single thing I had a hand in creating once I was done building it. After something's built, it no longer has anything of value to offer me. Whether it goes on to be used by a billion people or no one at all, I won't feel any differently. (I'd still reserve the right to boast at cocktail parties in the case of the former, however.)

There is one thing that doesn't sit well with me after writing this, though. The fact I've never cared about the things I've built means I've spent a lot of time building a lot of things that never mattered to me. Since striking out on my own in January 2024, I assumed the freedom to choose my own projects would allow me to identify work that really mattered to me. And I have! I've got a whole list and everything. Stuff that could change my life and others' lives for the better.

So far, I've taken all that time and freedom, and gone out of my way to build literally anything else with it. Not because I'm afraid of building those genuinely worthwhile things, but because those things' worthwhileness doesn't register as a valid criterion in my brain. The moment I sit down to work, my attention will be immediately captured by an unrelated problem and I won't be able to get it out of my head until it's either solved or supplanted by an even more daunting challenge. I won't let the day rest until I've proven to myself that it can be done. I can seemingly prove my ability to do anything except whatever it is I've consciously decided to do.

It's a strange, uncomfortable thing to sit with. Freedom often presents as a paradox. Maybe for an innovator, freedom to keep tinkering comes at the cost of a sort of aimlessness. A natural consequence when the motivation to tinker is for the act of tinkering itself.

I do have to say, though, that building meaningless stuff is a great way to pass the time. Realizing that's all I'm doing is hard, however. That I'm just passing time. When I get lost in my work, hours melt off the clock. Days pass in a blur. Precious weeks elapse. Seasons come and go—which, mercifully, doesn't mean much in Florida.

But if nothing changes this trajectory, will I regret it decades from now? Is this a problem I should be solving, and if so how? More rigor and discipline? More essays about my broken nature? More New Year's resolutions?

Who's to say.

At least I have a lot of experience deciding things don't matter to me. Perhaps that'll come in handy down the road.