I spend a lot of time thinking about tools, systems, workflow, efficiency, and all the usual modern obsessions. A decent chunk of my working life these days is basically trying to figure out where technology can remove dumb friction, save time, and free people up to do things that actually require judgment. I am very much in favor of that. If software can take repetitive nonsense off my plate, great. If AI can handle some of the mechanical work that does not bring energy or deepen anything or make anyone better, even better. Why spend time on data entry if you don’t have to?

But I also think there is a real risk in getting too fluent in that mindset.

Once you get used to seeing the world through the lens of optimization, it gets harder to turn it off. You start looking at everything the same way. Work, obviously. But then also your evenings, your weekends, your hobbies, your downtime. There is always some more productive use of time sitting there, staring at you. You could clean something up. You could research something. You could map out an idea. You could stay up too late vibe coding with Claude because you convinced yourself that building a half-baked prototype for no immediate reason is somehow a good use of time.

The point is, once your brain gets wired this way, it becomes very easy to treat unstructured enjoyment as laziness, or at least as a missed opportunity. And I think that is where things can go sideways. Because the goal cannot just be to make everything more efficient forever.

Somewhere along the line, you need a way to step out of that mode and rejoin your actual life. Not in some grand spiritual sense. Just in a basic human sense. You need rituals, habits, recurring things that signal the workday is over, the optimization loop is closed, and now you are allowed to enjoy yourself without turning the evening into one more project.

Friday night pizza is one of those things for me.

Not because pizza is sacred, and not because I am trying to build some sweeping philosophy of life around takeout. It is just one small weekly ritual that helps mark the transition. The week is done. We pick a place. Sometimes we go back to an old favorite, sometimes we try somewhere new. We talk about what each place gets right, the dough, the char, the toppings, whether one place clearly has its act together and another is getting by on local nostalgia or an overconfident Instagram presence. The vegetarian options matter in our house, which narrows the field in useful ways. None of this is profound. That is part of why I like it. It’s just a good way to unplug.

And I think that matters more now, because the tools are getting so good, and so available, that the line between useful work and ambient pseudo-work is getting blurrier. There was a time when being done for the day was more obvious. Now there is always one more thing you could do. Your laptop is right there. Your phone is right there. Claude is right there, ready to help you spin up a new idea, refine an old one, or disappear into some suspiciously compelling workflow experiment that has just enough addictive engagement to make you feel like you are not really working when, in fact, you absolutely are.

Not that the tools are bad. They are useful. I like them. I use them frequently. The trap is that if you are not careful, they can turn all of life into a soft-edged extension of work. Not mandatory work, necessarily. Often it is self-imposed, curiosity-driven, maybe even enjoyable. But still, it keeps your mind in the same posture. Still processing, refining, pushing. Still trying to get a little more out of the hour. And I do not think that is sustainable, or even desirable, all the time.

I think people need some part of the week that is allowed to remain ordinary. Dinner. A drink. A walk. Sitting outside. Having friends over. Watching something dumb. Going out for pizza and overanalyzing it slightly because it is fun and because paying attention to small pleasures is a decent use of a life. Things that are not building toward anything. Things that do not need to scale. Things that do not need to become content, or output, or a side project, or a clever proof of concept for what an AI-assisted life can look like when you really lean in.

Sometimes the healthiest thing is just to stop leaning in. I don’t mean that in a romantic, anti-technology way. I am not arguing for digital asceticism or pretending we all should to go back to some cleaner, simpler era that mostly exists in hindsight and nostalgia. I just think there is a difference between using tools to improve your work and letting the logic of optimization quietly annex the rest of your life. The older I get, the less I think the point is to eliminate every inefficiency. Some inefficiencies are just life. Some things are good precisely because they are not instrumental. They are good because they let you be present, because they mark time, because they give shape to a week, because they remind you that enjoyment does not need a productivity defense.

That is what Friday night pizza is, at least for me. Not a symbol carrying the full weight of modern existence. Just one recurring reminder that the week does not have to end with me hunched over a laptop, trying to squeeze one more useful thing out of the evening because Claude and I got on a roll. There will be time for that. But there also has to be time to just enjoy things. I think that is easy to lose sight of when you are ambitious, curious, and surrounded by tools that make it increasingly possible to do more, faster, with less friction. The danger is not just overwork in the old-fashioned sense. It is that you start forgetting how to be off. You start treating every open stretch of time as available inventory. And once that happens, even the fun stuff begins to take on the texture of work.

That is why I think these small rituals matter. Not because they are impressive. Because they are not. They are small, ordinary, easy to overlook. But they help draw a line. They help you remember that a good life is not just a maximized one.

And on a Friday night, that can be as simple as putting the laptop away, getting pizza with my wife, and talking about whether one place really does have better crust than the other.

The best investment committee debates don’t usually start with someone politely telling you that you’re underwriting a corpse.

But in a recent committee meeting, that skepticism was the collective initial reaction to what I was pitching. The argument was that the grocery giants are finally finishing off the little guys, and that specialty grocers are a dying breed and the whole independent ecosystem is just a slow-motion liquidation sale. The implication was that if we were underwriting the independent grocer end market, we were essentially underwriting nostalgia. It would be the retail equivalent of buying a rotary phone because you like the mechanical click of the dial.

I get the reflex. If you look at grocery from thirty thousand feet, the “common knowledge” story writes itself: price compression, labor headaches, and the inevitable gravitational pull of Amazon disguised as Whole Foods.

Plus, let’s be honest, independent grocers sound boring. In private equity, “boring” can be a polite euphemism for “how am I supposed to explain this to LPs.” But the more I sit with this deal, the more I realize that “boring” might be a substitute for a story we haven’t interrogated enough yet. Yet my own viewpoint on the deal hasn’t been immune to bias from my own internal narrative.

In my personal life, I hear a steady drumbeat of people (myself included) lamenting that they keep buying more from Amazon. It makes you feel slightly complicit, like you just stole an opportunity from your own community. We talk about wanting better options. We get almost embarrassingly sentimental about the local cheesemonger or the person at the bakery who actually knows your name. While the sentiment is real, it is does not make a useful market analysis, and it’s not a good way to gauge confidence in the future performance of an investment.

The trap is that these anecdotes are presented as “evidence” with the plural of that anecdote being assumed to equate to “data”. It feels like proof because we can all identify with the narratives and they come in neat little packages. But underwriting an end market isn’t the same thing as telling a plausible story about consumer guilt. The first job is to separate the story from the structure and forget entirely about whatever you want to be true, so that we can focus on creating something from scratch, untethered to any influence from selection bias.

The company we were evaluating provides the entire tech stack for these independent grocers: managed services, cybersecurity, payments processing, POS, electronic shelf labels, et cetera. You might equate it to something like the digital plumbing. No customer notices it until it breaks, at which point we all become acutely aware of how critical it is to our seamless day-to-day experiences.

So the real question wasn’t “Do we like grocery?”

It was: “Do we understand the sub-sectors within this market where a store owner with a sustainable competitive advantage will keep paying for technology, keep upgrading, and keep outsourcing complexity?” That is the compounding benefit we’re actually looking for, even if it doesn’t make for a good sound bite.

Some trends start to emerge when you stop thinking about independent grocers as a monolith. When someone says “specialty grocers are dying,” the only useful response is: “Which ones?” There are stores running on 1950s business models that are permanently bracing for impact. They’re fighting a price war against national chains with procurement scale they can never match. They are structurally challenged and they are fighting against basic arithmetic.

But then there is the other category. The ones that don’t try to be a smaller, worse version of a Kroger or a Wegmans. They compete by being specific.

• The Ethnic Grocer: Deep community ties and high basket frequency.

• The High-End Importer: Where you’ll happily go out of your way to pay $11 for a jar of olives even though they don’t carry any basic paper products.

• The Fresh-First Format: Winning on produce freshness and local sourcing that the giants can’t replicate at scale.

This differentiation changes the underwriting entirely. You aren’t asking if “grocery” is growing; you’re asking which operators have a defensible reason to exist. Those are the owners with the margins and the willingness to invest in digital transformation.

At a certain point, the debate can shift. If the market is split, the IT provider’s primary focus is no longer just “selling tech”, but rather customer selection. “Good selection” means targeting the operators who serve high-household-income shoppers and have the stickiness to survive a downturn. It also means having the discipline to say “no.” That can be one of the biggest challenges for a small business. Revenue is seductive, and the “bad-fit” customer is usually the one waving cash with the most desperation, hoping a new POS system will solve a structural business failure.

If the company picks the right winners, they become part of the operating fabric. They benefit from the growth of their customers, tenures get longer, and revenue becomes highly recurring. If they pick wrong, they’re just chasing small fires in a portfolio of struggling stores.

The ending here is ambiguous because, frankly, the discussion is still very much active at my firm. My colleagues might even be reading this. And I don’t want to sound like I’m grading anyone’s homework or claiming my “segmentation” approach is the only path to the truth. What I’ve realized is that underwriting an end market really just means refusing to let the easiest narrative do your thinking for you. It means noticing when you’re using your personal life as a proxy for data. It means treating a market like a collection of individual purchasing behavior decisions rather than one big trendline.

Maybe this end market is sneakily attractive, or maybe the “split” is still too messy to bet on during a cycle. I don’t know yet. But I’d rather have a debate about segmentation than a debate about vibes. And while clarity isn’t the same as confidence, it’s a much better place to start.

Share

I was never a history person. I liked it in high school, but I never went looking for it later. I spent more time in math class or at the lab bench for physics and chemistry. When I read for fun, it was fiction, or food, or travel. Forward motion stuff.

So it surprised me that buying a house that’s “supposedly built in 1770” has turned me into the guy with fifteen browser tabs open, zooming in on scanned deeds at odd hours like there’s a prize at the end.

The former owners left us a small pile of old deeds. I assumed they’d be a quick curiosity, maybe an hour of skimming, maybe a fun anecdote at a dinner party if someone asked. Instead, they sent me straight down a rabbit hole, over and over.

It felt relatively straightforward at first. Find the deed, match the property description, trace the owners back. Easy enough. Then it got messy, fast.

The main problem is that old property descriptions are not written for someone in 2026 with Google Maps and an addiction to clean spreadsheets. They’re written for someone in 1820 who knows where the “old road” is, who knows which neighbor is “Mr. Green,” and who can look at a stake with a pile of stones and say, yep, that’s the one. Some of these deeds reference a rock, or a birch tree, as a corner marker. Which is great, unless you are trying to prove anything definitively two hundred years later and the tree is, predictably, not responding to my emails.

I also learned quickly that a lot can go wrong with a single misread detail. The deeds we were left by the former owners pointed to a chain of ownership that seemed plausible, until I realized the whole thing might be based on a bad assumption. Whoever originally tagged these deeds as belonging to this house appears to have misinterpreted the cardinal directions. East and west mattered a lot when a road was the main reference point, and it matters even more when the road has shifted, been renamed, or been swallowed up by new streets and a totally different way of describing addresses. One wrong directional read and you can end up confidently researching the history of someone else’s land.

Which was, I’ll admit, a little deflating. I’d been feeling productive up to that point.

The most satisfying moment so far came from my wife, not from the deeds. She found an old town map from 1838. It doesn’t get us back to 1770, but it gets us close enough to feel real. When we zoomed in, our house was right there, plain as day, sitting near the center of the map. The brook behind our house is there too, in the same spot it runs today. And a house down the street, the Alms House, shows up on the map as well, and even today we drive by some iteration of that same place.

We’re going to print that map and hang it in the house. Not because it solves the whole mystery, but because it’s a clean snapshot of this place at a point in time when it was still small enough to fit on one sheet of paper, and because it’s oddly grounding to see your home as a labeled object in someone else’s world.

At this point I’ve accepted that the online digging only gets me so far. The next step is going to be going down to the county deed records office and doing the in-person version of this, the part where you stop pretending everything is searchable and you start flipping through books, asking dumb questions, and discovering that one key record is filed under a name you didn’t think to search.

I’m sure I’ll hit more roadblocks. More false trails. More moments where something looks obvious and then isn’t. But I’m also kind of looking forward to that, because the point has shifted. I started out trying to prove a date. Now I mostly want to learn the story, even if the story is incomplete, even if the best answer ends up being “we think it was around then, but here’s what we actually know.”

Either way, I’m in it now, and I have a feeling this is going to take longer than I expected, in the good way and the frustrating way, which is usually how anything worth doing goes.

Subscribe now

Heading into Thanksgiving, I’m clearing the notebook and putting down a few thoughts that have been nagging at me. They go back to a June night at the Rose Bowl. We were living nearby and went to PSG against Atlético Madrid, a match that would have sent ten-year-old me into cartwheels. It nudged me back into following the sport, so I subscribed to Football Daily, the Guardian’s evening newsletter. Then work got busy and I stopped opening it. Months later I clicked one at random and found a line I did not expect to read.

Steven Gerrard—best known as Liverpool’s leader and a mainstay for England’s national soccer team—told Rio Ferdinand—his England teammate and now a podcaster—that England’s Golden Generation were ‘egotistical losers.’ And then, perhaps even more unexpectedly, that he often felt deeply and tragically alone. That’s the part that surprised me. Maybe it shouldn’t have, but it did.

Why did it land so hard? Perhaps because we rarely hear this from the inside. After a disappointing run the script is usually familiar, to blame the outcome on each of these in the following order: tactics, selection, luck, penalties, the press. Safe topics that stay on the whiteboard. This felt different. Gerrard pointed at the hours around the work. Long afternoons in an empty hotel room with a few channels. The same tables at dinner. Club cliques that were hard to un-stick. He said he loved playing for England in the 90 minutes of the match, and hated the time before and after. That is simple, and for that reason it is striking.

I keep thinking about why this feels like a bigger moment than a spicy quote. Gerrard is not a side voice. He is central to that era. You expect careful nostalgia, or a narrow argument about roles and systems. You do not expect a blunt noun like losers followed by a plain statement about loneliness. It made me wonder how often the real reason a great team falls short sits in a place we don’t see.

A little history can help. England in the 2000s had names everyone knows. Gerrard and Lampard together. Beckham on the right. Ferdinand and Terry. Neville. Cole. Rooney. Competent managers. Sensible plans. Familiar and disappointing exits. Quarterfinals, analysis, the same debate every time about why failure seemed unavoidable. Each explanation had a piece of the truth. None touched the feeling Gerrard described.

Maybe the shock is also about what television teaches us to see. Warm-ups look cheerful. The tunnel looks friendly. Social media shows the plane, the jokes, the bus. It looks like a traveling party. Gerrard’s account suggests something more ordinary and more difficult. A door that shuts after lunch. An afternoon that passes like molasses. A seat at dinner that never changes. Perhaps what looked like team chemistry from afar was more like choreography.

I think part of the surprise is that it breaks a code. Elite athletes learn to keep emotion away from the microphone. Not because they lack it, but because it can be used against them. English football adds a bias toward stoicism and strong club identity. The badge you wear nine months of the year is not just a shirt. To say those identities carried into the England camp is to accept some responsibility rather than sliding it to the manager or the press. Easier to say nothing. Easier to let time soften the edges. He did not do that.

Share

The timing matters too. He said it years later, when confession can be a brand move. This did not read that way. No heroics and no sermon. Just a straightforward description of good work surrounded by hours that didn’t help. That calm tone is why I think it is worth noting. It closes the gap between what we thought we were seeing and what one of the main actors says he was living.

What follows from that is not a tidy lesson, at least not for me today. It’s a different question. If the issue was not only talent or tactics, what happens to a high-talent group when the empty hours never get solved. I think the answer is not dramatic. Passes arrive a half beat late. Runs are not made. Small risks are not taken. People sit with their own because it is easier and they are tired. No scandal, just drift. Perhaps that is why the results were stubborn without being catastrophic. Things mostly worked, until it mattered that they worked together.

Football Daily helped me take this in because it did not oversell it. The note was steady, a few facts, a little context, no gloss. That restraint matches the content. “Egotistical losers” is a hard phrase for a group that won almost everything with their clubs, but the weight is in the second part. A player saying, in public, that the day around the match felt empty. We like to believe elite inputs guarantee elite outputs. Maybe they usually do, until seven unstructured hours start to carry the result.

I also keep coming back to how this reached me. If we had not gone to that match in Pasadena, I probably would not have subscribed. If I had not ignored the newsletter for weeks, I might not have opened it on that day. It makes me think that some ideas arrive when you are ready for them and not necessarily when they are published. That feels right for this Thanksgiving week, when many of us will sit at the same tables and run familiar plays. Maybe the hours around the thing matter more than we admit.

So why should anyone be taken aback? Because it is rare to hear a principal voice say, without spin, that a famous team fell short for a human reason, not a schematic one. Because it challenges the highlight reel we carry in our heads. Because it suggests that what looked like a mystery might have been something simple, and a little sad, happening in plain sight.

Subscribe now

Category education, in plain English, means you are not just selling a product. You are teaching people what the product is, why the underlying problem matters, and how this thing could fit into everyday life. It is the work that happens before potential customers even decide if they have a preference. That can sound like homework from marketing class. The fun part, at least for me, is seeing how a company tries it at full scale and what follows.

Here is what my reading suggests. In late 2020 the NFL named Hyperice its Official Recovery Technology Partner. That appears to have put the devices inside all 32 clubs and, more importantly, on camera. If you watched a game that season, you may have seen trainers use the tools and heard broadcasters say the brand name out loud. Search interest seems to have climbed. Some retailers who had been slow to respond reportedly called back. If that is right, the lesson on national television did what it usually does. People moved from “what is that” to “which one should I buy.”

Then the next chapter arrived. Once the category made sense to regular people, the marketplace did what marketplaces tend to do. A lot of similar products showed up on Amazon at lower prices. The company that paid to teach the lesson now had to explain why its version was worth more than the near-matches in your cart. Inside Hyperice, I would venture to guess that the weekly rhythm shifted. Launch plans still moved forward. Two new kinds of work probably took more time. One was federal litigation, which follows a slow calendar of filings and hearings. The other was Amazon’s in-platform patent process, a faster, platform-run procedure focused on whether a specific listing should stay up or come down for IP infringement. Glossy creative doesn’t matter here. Documentation, dates, and diagrams do.

The press covered the back-and-forth like a trade. Hyperice files a suit. A rival responds. More names enter the story. From the bleachers it looks dramatic. From the inside it likely feels like the bill that shows up when an awareness play succeeds. You taught a lot of people that recovery matters and now everyone wants to sell recovery to them. The real question is whether there is enough customer preference and enough protection to keep a lead.

Share

Why did this pull me in? Because using the NFL as a classroom seems to have forced the rest of the company to mature faster. A league partnership is rarely just media. It can pull forward distribution deals. It can test supply chain discipline. It can push customer support to handle a higher volume of questions. It can also bring copycats sooner than expected, which means legal and operations need a plan. Many brands reach for a big stage and then discover their systems cannot carry the weight. Hyperice appears to have built those systems in real time, in public, with a lot of people watching. That is a hard thing to do.

This thread also lines up with a few traps marketers learn to respect. Attention does not automatically become advantage. Teaching the problem gives attention to everyone in the category. How much of that attention can any one brand really hold? The part that turns attention into category leadership sounds unromantic. Make the product reliable. Prove the claims. Keep shelves stocked when interest spikes. Answer emails.

Another trap is underpricing the follow-on costs. You set a budget for awareness campaigns. It is easy to forget to set one for enforcement and channel management. Those costs show up later and can eat margin if you ignore them. A third trap is treating borrowed credibility as permanent. The NFL helps at the start. After that, trust is earned the slow way.

Was this a bold bet with real upside, or a downside risk that should have been obvious from the start? My guess is that it depends on timing. If you buy mass awareness before distribution, service, and defensibility are ready, you may gift the market a lesson and leave the door open. If those pieces are already in place, the same awareness can harden your lead. The stage tends to amplify whatever foundation is already there.

Yes, this does sound like I spent an evening with press releases and law firm blogs. That is accurate. I like this story because it is messy and practical. It suggests a path, not a rule. I plan to keep watching Hyperice and the copycats to see which way the line bends.

Subscribe now

Others have done the work in mapping this territory. Joshua Rothman, at The New Yorker, gives it a plain name, unlived lives, and points out why they glow: we see an edited cut of the path we did not take and mistake its neatness for inevitability. It is a narrative trick and once you see it, you notice how often the mind swaps in a cleaner version of someone else’s day and assumes it is reality, which is why the alternate route often looks wiser after the fact. Kieran Setiya, who teaches philosophy at MIT, offers two words that help sort the feeling. Telic is about finish lines and goal posts, the map part of us that wants routes and endpoints. Atelic is ongoing, the weather part, the quality of the air while you are inside a day. Miss the second and the first starts to run your life. Taken together, those two lenses are enough context for what follows and they keep me honest about what I am really comparing when I try on other lives from a bench in the heat.

The usual argument goes as follows. When you are young the options sprawl out in front of you. Then work and place and people set a shape, and switching tracks gets costly or complicated or impossible. Careers reward compounding and moves get harder. A city begins to fit, and other cities get reduced to candidates for weekend visits. You keep the friends you can actually see. You are in a corridor that is tightening around you. It explains the tug you feel in a lobby when you see a different logo on a badge at check-in and remember the route you did not take. It explains the small ache when you meet someone who stayed in one place for twenty years and can tell you who taught their kids to play piano on that block. Or the equal ache when you meet someone who never stayed and carries a pocketful of stories that start in one country and end in another. The corridor model allows for loss without drama. You choose this and not that, and the not-that feels real.

Still, it is not the whole story. The corridor is a map. It shows roads and intersections and cul-de-sacs. It makes it look like if you had taken the other road you would have ended up in a fixed town with a known climate. Life has not worked that way for me. The lives I imagine when I look at other people are clean. The lives I have actually lived are not. The difference is something akin to the weather.

These maps tell you where the roads are but the weather impacts your day. You can stand on the same corner two days in a row and one day will feel possible and the next will feel like a chore, and nothing on the map has moved. We forget this when we look at the lives we did not pick. We imagine road and destination. We skip the cold front pushing through at 3 p.m., the bad light in the room, the week you get nothing right. From the bench, the contractor walks like the stress and anxiety have lifted after rain. The teenager’s stride has gusts in it. The stroller dad looks like a fog advisory and a pocket of sun at once. None of that is on the map.

Share

Sometimes I picture a teaching track. Chalk dust, office hours, a few students who surprise you in ways you can describe to no one else. The scene in my head is quiet and specific, a door cracked open, a stack of esoteric books. It leaves out committee meetings that start at four and run long. It leaves out the fight over who gets what course. It leaves out the fifth paper in a row that cites the introduction to a theory and never quite lands. The image is tidy because I made it tidy. That is how the mind can cheat us.

People who study regret and “what if” thinking keep circling the same point. Neal Roese is one of these people and his research shows how we trim the rough edges from our mental edits. We cut to the best parts and we mute the friction. It is the director’s cut with the hard scenes missing. Daniel Gilbert studies how we predict our feelings and finds we are not very good at it. We overestimate how long regret will sting, then adapt faster than we expected once real life arrives. Put the two together and you get a simple caution. The imagined version looks great partly because we are holding a highlight reel, and the pain we fear inside the real version tends to fade. You can see this in your own history. Think of a decision you once dreaded. Now think of how ordinary it feels in memory. That shift is adaptation doing its work. Which is another way of saying my professor daydream leaves out the long meetings on purpose, and maybe the dread would lessen with familiarity, or perhaps it would just become part of the weather.

I don’t think the solution is to shame the imagination. Wondering about other roads is not a moral issue but rather a standard feature. If anything it is a sign that the machine is running. You are paying attention. You recognize that every decision shapes the next field of view. You look up from your phone and a contractor in paint-streaked cuffs gives you a full paragraph on a way of living you did not test. You see a teenager and remember the exact tilt of your own head at that age when a narrow thing felt like the whole world. You watch a dad bounce a stroller wheel down from a curb and you can feel the small calculation he makes in his body, and the worrying soundtrack that never stops. The point is not to stop doing this. The point is to be honest about what kind of feedback it is giving you.

There is also the simple fact of drift. Weather shifts plans. It creates new roads and closes off old ones. People you meet change the probabilities in ways you cannot model. A health issue appears and the thinking you did about the next five years becomes a different kind of thinking. A company merges and the team that made sense last spring does not make sense now. A friend moves back to your city and every Friday changes shape. None of this is redemption or tragedy on its own. It is the system. If you stand in it long enough, you see the patterns. Pressure builds, pressure releases. You get a run of days when you think in straight lines. Then you do not. This does not make choice irrelevant, it makes it honest.

I have heard the counter that weather is an excuse, a way to avoid owning your map. I do not buy that. The point is not to make choices lighter. It is to right-size the stories we tell about what we did not choose. If the picture of the unlived life is going to have any use, it should at least be true to the way days feel when you are inside them. Otherwise you are comparing a shelf display to a used thing. You will always pick the display.

Back on the bench, the small things keep happening while the big idea tries to take over. The door opens. The door closes. Someone laughs at something you didn’t quite catch. A car creeps past trying to decide if that spot is a spot or if there’s a motorcycle hiding. The dog turns, plants his front paws on my knee, and looks at me with the face that means he has adjusted his plan from sitting like a person to being treated like a person. He tries to sit again and fails again. He stands, resolved. I check the time.

Suddenly I realize the contractor has crossed the street and is gone. The teenager props the racket bag against a hydrant and ties a shoe and then is gone. The stroller dad makes it down the curb, checks the baby, nods once at no one, and is gone. I keep doing the same thing, trying on their days like jackets you would not buy because they do not quite fit but you like how they feel in the moment. I remind myself that I am picking lining and buttons and ignoring the seam that digs in under the arm.

What about the lives I could still take on, the side corridors that are technically open. Those exist. They always exist. You do not have to torch your map to walk a different block. You can add a course without quitting school. You can work with a different set of tools and see if the work feels different. You can spend more time in one neighborhood of your own life and see whether depth gives you something breadth cannot. I do not think of these as grand pivots. They are local moves. Weather moves. You feel a front and you close a window. You see a break in the rain and you go around the block. No slogans needed.

If this all sounds obvious, it’s because we know it and forget it on a loop. The corridor story returns because it is simple and it feels fair. You picked A and not B, so you cannot have B. The weather story takes more patience. It asks you to accept that a big part of how a life feels sits outside the lines. It changes while you look at it. It will not hold still for your comparison. It is hard to put on a slide. It is easy to live and hard to summarize.

There is one more piece that matters, which is that gratitude and the small mourning can sit next to each other without canceling out. You can be happy and still feel the loss of a road you did not take. You can feel the loss and not make it into a verdict on the road you are on. If you accept the weather model, this gets easier, not harder. You stop acting like you missed a perfect day and start remembering there are not many of those. Most days have a mix.

My wife comes out of the ice cream parlor with the cups. Peanut butter for her, purple for me. Somehow it’s already running down my thumb. I miss it with the napkin and now my hand is sticky. The dog finally stops trying to sit. The bench creaks. It is still hot. The corridor narrows. The weather keeps changing inside it, and the forecast looks good to me.

Subscribe now

We spent twenty-seven minutes on a one-time fifteen-hundred-dollar benefit for three staff members, a small question that swelled to fill the room because small questions do that if you let them. I asked whether we were in the right conversation for the board, which is governance-speak for: “please tell me if I am over my skis, or whether this was better handled as a policy somewhere else.” The air eased a little, chairs settled, someone circled a note. It might have been the right call; walking to the car I wondered if I had called it a minute too soon, my batting average on perfect timing remains safely hypothetical. Looking back all these years later, I realize that was the first time I felt the job in public, the thin line between being useful as a board member and being in the way.

Over time these nonprofit board roles began to look less like a series of important pronouncements and more like boundary work. Staying curious, keeping noses in and fingers out, turning live issues into policies when they belong in the room rather than on a to-do list. What follows are a few moments when I missed the line and a few when I caught it, and the small tests I reach for now, provisional as they are.

My apprenticeship started years earlier in a Harlem cafeteria where I tutored after work, with wobbling tables, two cups of apple juice warming between me and my assigned middle schooler, fractions that blurred into nonsense from repetition. I stacked chairs, chased markers, stayed late because someone needed to lock up, said yes to the small roles that never make a brochure. Most nights I was thirty percent tutor, seventy percent furniture mover, one hundred percent sticky with apple juice. One evening the program director handed me a packet the thickness of a paperback and a seat at the junior board. No ceremony; just read this and show up. In my early twenties I expected board decisions to live in speeches. Slowly I began to suspect they ride on the questions that get asked and the ones that do not.

In Boston at Wondermore where I eventually became Vice Chair and then Board Chair, I started to see boundary errors in public, including my own. I once let a swag-giveaway debate hijack a meeting because it felt urgent; we burned forty minutes deciding nothing the staff could not decide faster, then ran out of clock for the strategic item that actually needed us. I drove home with the sour sense of having been present and unhelpful. After that we tried a simple experiment: if an item was operational and we could not shape it into a policy within a minute or two, we parked it, named an owner, set a date, moved on. It did not fix everything; a few times we parked too much and had to circle back. I suspect it helped more than it hurt.

Boundary work also meant saying no to distractions, even when the dollars glittered. We declined a shiny program that promised a flattering announcement and restricted income; it would have nudged us a few degrees off what we do well and soaked staff time we did not have. The announcement would have been photogenic and my ego wanted desperately to say yes. Saying no cooled enthusiasm and cost us a report we would have enjoyed writing; we kept the more important thing we needed, which was attention for the core job the organization exists to do. On paper that sequence looks neat and tidy; in the room we were feeling our way through the dark.

Only later did I find cleaner names for what these rooms had been teaching me. An HBR conversation with Ellen Zane gave me a phrase for something I had been fumbling toward, “noses in, fingers out”, and left me with a better question than the slogan: what counts as a finger, and who decides, and when; I keep checking to see if mine are showing. People talked about quarterly meetings where acronyms stampede and the usefulness of a naïve question asked once. None of it was new, only more legible for having been said aloud, and stamped with the HBR brand.

Share

Nonprofit time slips quickly on the calendar. In September the year looks orderly, a retreat here, a fundraiser there, packets you can read on a train. Then a filing slides past a deadline, a key staffer gives notice, the lease comes due. When that season hit us and the packets doubled, what seemed to help was not volume but plainer talk and tighter asks. Shorter memos that led to decisions, the criteria, the owner, the date, and what would count as “done”. Then we tried to stick to it. The discipline read as warmth to the staff because it respected their time and decision-making authority, which is another way of saying we were learning to respect our own.

Different rooms, same boundary. Most days now I sit in for-profit boardrooms where the acronyms change and the units of consequence seem larger, but the rules feel familiar. I try to come in read-in enough to ask plain questions. I try not to solve operational puzzles from the bleachers. I try to respect the people who carry the bag every day and try to avoid grandstanding. On good days those habits are enough and the room feels inviting; on other days you miss and try again.

If there is a lesson here, it is provisional. Informal roles can turn out to be small apprenticeships, and sometimes they lead you into rooms, and sometimes, once you are there, they hand you responsibility you did not expect. I keep a few simple checks that seem to help, like the quick test for whether an issue belongs in policy or in operations; they fail often enough that I do not mistake them for rules. I have tried to laminate them. Mostly I try to notice which question might move the work an inch and ask that one first.

Somewhere there is still a cafeteria where a kid is chewing a pencil and a volunteer is trying to be helpful for an hour before catching a train. I do not want to romanticize it; I want to admit that those hours teach you how to carry chairs, then packets, then the weight of a vote without theatrics. I am still learning what counts as a finger, usually after I have pointed with it.

Subscribe now

I found the broker the way most people find preventable trouble, by searching Google and skimming Reddit until the repetition of vague adjectives started to feel like validation. In the end I picked the one that showed the most reasonable price next to “best reviewed” and “book now to lock rate,” because it promised the earliest pickup window and I was out of patience. I filled out the form, paid the deposit, and let them choose the carrier for me. Which is why I suddenly knew the name “Prairie Star” only about two hours before their truck rumbled down that quaint little side street.

This is where Dana Mattioli has some useful insight to share. She is a Wall Street Journal reporter who has spent years understanding and scrutinizing the way Amazon runs a marketplace and sells inside it at the same time. Her book, The Everything War, lays out the mechanics of that posture and why it matters beyond books and batteries. Her point is that once a company writes the rules and plays the game, the customer’s “choice” is mostly a path someone else drew. That is what this brokered world felt like: a wide page that narrowed into a form that said we will decide the rest for you, and bright buttons that looked like decisions but were really signposts. As Mattioli puts it in one interview, these platform businesses win “oftentimes… because they have their fingers on the scale.”

What I dealt with was not brokerage in the old sense. It was a platform-shaped market that set the terms, sorted the options, and only then, after further delay, revealed the counterparty. The quote page did the steering with “best reviewed,” lowest price, and a bright “book now”. The carrier was assigned later from a behind-the-scenes marketplace. The upsell cadence for “extra insurance” arrived on an marketing-optimized schedule. When delays hit, the broker and carrier pointed past each other. That is the structure Mattioli anatomizes: the rule writer also playing on the field. Once the platform both sets the menu and sells from it, “choice” is a path already drawn.

Subscribe now

A couple days after the car was picked up and hauled away to god knows where, the broker who promised white-glove coordination became a maze-like phone tree. After notifying me of a delivery delay with a short text, the carrier answered my call with the tone of a weather report, then put me on hold to “check with dispatch.” Yeah, right, and I’ll go check with his holiness the Dalai Lama while you’re at it. I pictured an empty desk chair and a wall calendar with a truck on it. All this while I was refreshing the tracking page as if the truck could sense my attention and speed up. Every path to a human with authority was hedged by policy – “sorry, sir, nothing I can do about it.” Meanwhile my inbox kept filling, every three days like clockwork, with invitations to buy extra insurance on top of the insurance that was supposed to be enough. It felt like being asked to tip the pilot while the plane was still taxiing.

Lauren Oyler approaches the same landscape from the side of language. Her collection of essays, titled No Judgment, is her account of what public ratings and review platforms have done to how we make and present discernment. She argues that the ritual of rating every interaction trains us in a performative way, which is why a hundred five-star reviews can blur into something both pleasant and simultaneously useless. I think she is right because I cannot recall a single voice from those pages, only the gloss of agreement. Everyone sounded reasonable, though no one told me anything that would have helped while stuck on hold trying to figure out where that car was and when I could see it again. Oyler describes the feeling cleanly: “you start getting so many recommendations that you think, ‘this is completely meaningless.’” You do not need to be a literary critic to know what she means. Try shipping a car.

Here is my view, without the polite hedge. Mattioli explains the structure that bends your choices before you arrive, Oyler explains the language that makes that bend feel normal. Together they describe why I could drown in ratings and still feel unprotected. Why “best reviewed” and “most trusted” functioned as décor instead of guardrails. Why a broker could sell me coordination and then disappear into hold music. This is not about one bad actor. It is about a system that turns consumer anxiety into a premium pricing model and makes my judgment content.

Share

Somewhere in the country a truck I cannot picture is moving through a place I cannot name, straps holding, tires humming, a clipboard full of notes I will never see. My phone chirps with the promise of new information, though it turns out to be the exact same sentence as before, as if repetition could grind doubt into trust: “your car is on the way, do not reply to this message.”

Early on I pushed us to assimilate. She had a craving for chilled soup to fight the summer heat, so that weekend we came back from the farmer’s market with a couple bags full of ingredients that, to a neophyte like me, seemed could plausibly result in gazpacho. I had never been a huge fan of gazpacho, but one afternoon and three spoonfuls later I became a convert, which said more about the produce (and my future wife’s cooking skills) than it did about me. Seasonality has a practical way of directing your plans. And then calendared obligations took over. Most weeks I was on the moving walkway between terminals and coasts, Delta through Atlanta, the same gates at odd hours. I will not name the quiet lounges where I found respite; the hidden escalator in that terminal is a moderately well-kept secret. A Red Sox cap lived in my carry-on and kept me rooted. In hotel rooms Shark Tank bred familiarity; at home we saved The Sopranos for the couch and flew through all six seasons. I am good at productivity, but this past year asked for presence. Maybe Tony was right about family and rituals.

One of our favorite third-places was a small café in a leafy neighborhood with simple sandwiches and a sidewalk table good for people-watching. A sitcom actor you might recognize walked by with a coffee on one of our first visits; he never reappeared, though I kept half-expecting him like a running joke. The grocery store grew familiar in the steady way that matters. Same staff, same shifts, same quirks. The sort of faces you start to recognize before names, a quick hello that says we see each other here. That is enough.

Rituals are what I’ll end up missing. Not so much the map or the topography. William James, the psychologist behind The Principles of Psychology, called habit “the enormous fly-wheel of society”; my interpretation is that repeated acts steady a life when everything else moves. Cultural historian Svetlana Boym, in The Future of Nostalgia, draws a line between restorative nostalgia, which tries to rebuild what was, and reflective nostalgia, which lingers on the texture of a time. I’m attempting to describe the second kind, a reflective look at a liminal chapter. And when a chapter closes, the choreography stops.

You are not grieving a neighborhood or a sunset or a vista so much as the reliable order of its moves. The way Sunday tennis set the week in order and the way a saved episode held a place for two people to be in the same room at the same time. I do not want to reconstruct a shaded corner tennis court or the exact café table; I want to remember with fondness that our days had a pattern that fit the time. There is plenty to look forward to in the next chapter. The sentimentality sits alongside it. You can be eager for what comes and still miss the old choreography. Choreography like the five wedding-dance lessons that did something I did not expect. They gave me a different kind of confidence, more posture and timing than mindset; standing up straight, listening with your shoulders, moving together without rushing. It’s unlikely I’ll miss California all that much, in the geographic sense. Instead I’ll miss what won’t be possible to recreate.

Share

Fridays had a routine that took some dedication to refine but eventually found something we could not improve on: driving to the next town for a Neapolitan pie, picking up a good Barolo at the shop nearby, and heading home on my favorite winding drive through the hills. The oven heat on my forearms as I carried the box to the car, the Barolo bumping the console on turns, the small exhale when we set it all down on the table. What I will miss is the order of it all, and the small relief that arrived because the steps were well worn.

Not everything fit neatly, and in July our attention turned towards prepping for a move. When we scheduled the appliance donation, our temperaments showed. I wanted to keep them plugged in until the last possible hour; she wanted a two-week buffer in case the hauler slipped so we could reschedule without a scramble. We rarely disagree, this one simply made our risk tolerances visible. I tend to see how close the needle can run to E. She prefers to keep a full tank. We found a middle that worked, packing has gone off mostly without a hitch, and we still despise the whole process, which counts as shared values even if not always done with shared methods.

When the week of ‘lasts’ arrived it did not announce itself like something you might expect. We just kept our schedule. The last Sunday morning tennis lesson gave us a coveted shaded court and our best rally yet. The final first-dance check-in confirmed we had finally managed to (mostly) remember the whole routine. The last pizza was consistent, reliable. Then there were farewell cards from our instructors: kind, unexpected, and heartfelt. The sort of notes that land because someone paid attention while you learned.

The practical case for moving back east is easy for us to make. Travel shrinks. Work, friends, and family move back within reach. The relief is not theoretical. Eagerness for what is next is not at odds with gratitude for the pattern that got us here. Still, what we built is not a fragile museum of coastal clichés. The place itself will leave its mark. Cool walks under the marine layer. Produce that makes even a simple salad feel like you cheated the recipe. And the way late light casts the hills aglow late in the evening. I remember my fiancée’s colleagues folding us into a birthday party, showing how temporary community still matters. The clerks at the grocery store became familiar company without a single exchange of names. None of it photographs well, but it still built up all around us.

A wedding and a honeymoon sit just ahead, so looking out more than a few weeks feels both hard and unnecessary. Day by day feels right. Somewhere in our packed-up cardboard boxes there is a preserved butterfly in a small frame that will carry for me a symbol of our time here. Not because it is rare, but because it reminds me that change is normal and attention is the part you get to keep.

On the last Friday-night pickup she held onto the pizza box in the passenger seat, and I set the wine in the back. A relatively cool night in August, the scent of jasmine blossoms reached through the open car window while we waited at the light. The place was background, the pickup was the ritual. The light changed. I checked the mirrors and turned toward home. Wherever that is.

Subscribe now

A chef fussing over a playlist is not a hobbyist’s indulgence. Charles Spence calls it “sonic seasoning,” the deliberate pairing of sound with flavor, and his lab has spent years showing that what we hear changes what we taste, from the crispness of a chip to the way sweetness blooms when the music tilts brighter. Heston Blumenthal made this literal with Sound of the Sea, serving shellfish alongside the hush of waves in a set of tiny headphones, demonstrating that context can heighten sensation the way salt wakes up a tomato. In a room as intimate as Le Comptoir, music is pacing and temperature, the rise and fall that tells the service when to glide and when to lean in. Curating it is hospitality in stereo.

About ten days later, back at my desk trying to put a dent in the pre-wedding to-do list, the welcome-party playlist muscled its way to the top: a seemingly straightforward task that felt larger than the others. Le Comptoir kept echoing in my head, that slow tip from table talk to toe taps, the way the room seemed to grow with the music as the evening warmed. This party is family and old friends, the kind of night that should travel from handshakes to hugs without anyone noticing the gears. The little rectangle of metal and glass that controls the sound suddenly felt like a promise to help it along. I could picture the space, the french doors open to the gardens, the first drinks arriving, the first stories loosening, and I wanted the sequence to earn that shift.

If you want a single authority on why this even matters, you could do worse than David Byrne, who has more than earned the right to talk about how sound meets space. He helped reinvent the American music scene with Talking Heads, took home an Academy Award for the score to The Last Emperor, watched his band enter the Rock & Roll Hall of Fame, and turned a concert into a Broadway event with American Utopia, which the Tonys honored with a Special Award. In How Music Works he makes a deceptively simple claim, that music is made to fit its room, and likes to pose a question that sounds almost too neat until you sit with it for a minute: does the venue make the music? He traces how human chanting swelled to meet stone and vaults, how punk sharpened itself to cut through CBGB’s concrete box, how arena anthems learned to bounce off steel and air. Context, he keeps saying, shapes the thing itself, including unglamorous forces like budget and logistics. A playlist for a dinner counter is part of the pacing, the way conversation finds its rhythm.

Subscribe now

There are two of me editing the track list, each with an opinion and a memory, and they do not always agree. The Purist likes a clever segue, the kind that earns a grin from anyone who has ever squinted at liner notes. The Host likes a room that loosens its shoulders without having to think, a low pressure tide that pulls people toward one another. Early in the night the Purist reaches for a deep cut with a perfect intro, brushed cymbals and a bass that walks without hurry, but the Host catches the rise in conversation and chooses space instead, something that leaves air between the glasses and the opening chit-chat. Later, when the bar grows loud and the floorboards pick up the rhythm of shoes, the Purist wants to stack two tracks that were written in the same key, as if they were distant cousins. The Host imagines the laughter by the bar and chooses the album cut with a longer intro, giving the table in the corner time to land its story. The voices are not enemies so much as a duet, call and response, and when they start to bicker I hear David Byrne in the background asking his question again about the room teaching the music how to behave. Which is another way of saying that the audience is not the crate, the audience is the room itself, breathing and deciding.

Here is the embarrassing fact first: I want you to like the songs on my playlist. Not just tolerate them, not just sway politely, but like them in a way that makes your face change. Though it’s of course true that none of these songs are mine, they are borrowed light arranged in a line and I am simply angling the mirrors. The insight might be that curation is still a kind of authorship, a small act of arranging attention, and that makes it tender in the same way cooking from a recipe is still cooking. We risk versions of this all over our lives, at work and at home, whenever we draft a letter to a friend or set a table that says stay; whenever we pick a story to tell about who we are. If I am honest, the hope is simple, that the thing I made out of other people’s brilliance will land warm and be taken in good faith, and that the room will meet it halfway.

You hope for that one lift that belongs to the room and not to you, and if you are paying attention you will feel it before you name it. The clatter dims without effort, the talkers slow down mid anecdote, a harmony surfaces from nowhere and surprises the person who sang it. The chorus arrives and you can hear the grin move across faces, same as it ever was. I have loved this part since I was a teenager fumbling with burned CDs and speaker wire, throwing parties that were mostly an excuse to make the mix. I spent more time on the order of the tracks than on the snacks and felt no guilt about it. That pleasure has not changed.

Share

The simulation, devised in the 1960s to expose the bullwhip effect (small shifts in demand that swell into wild upstream swings), unfurls similar to the way a new job does. Early inputs feel harmless. Yet by round four the board is a yard sale of cardboard and regret. One hasty decision at the retailer ricochets upstream until the factory groans under mountains of phantom inventory, while the storefront sits empty and confused. The lesson stings because it is immediate. Information delays breed anxiety, anxiety breeds over-correction, and over-correction cements a cycle of waste.

For a freshly hired CEO, those first moves arrive in unassuming calendar blocks labeled “listening tour” or “strategy refresh.” Investors and employees scan every gesture like auditors, searching for clues that signal discipline or drift. McKinsey once tallied the data and found that companies led by CEOs who nail early priorities deliver a twenty-five percent higher total shareholder return over their first three years. A new CFO’s credibility with lenders lives or dies in the first quarter, when forecasting rigor meets the gray fog of inherited assumptions. A new COO takes over supply lines no less twitchy than our beer game chain, except the currency is real cash and the scoreboard is public.

Share

Two weeks after taking the helm of Citigroup in 2021, Jane Fraser declared “Zoom-free Fridays” and a hybrid work pilot, signaling that employee wellness was now table stakes for performance. By day sixty she announced Citi would exit consumer banking in thirteen Asia-Pacific markets, redeploying roughly $7 billion of capital into wealth management and U.S. cards. The early clarity reset investor expectations and let Citi absorb a $3.8 billion restructuring charge without a share-price nosedive.

Why does the window close so fast? Because organizations, like cardboard counters, develop memory. By day thirty, hallway gossip begins to calcify. By day sixty, budgets and head-count requests point back to the priorities declared in week one. By day ninety-nine, habits morph into culture and any reversal can feel like trying to erase ink with a damp napkin. Ignore that clock and future staff meetings can stagnate with polite silence and without meaningful progress.

It can happen outside the corner office, too. Move to a new neighborhood and the equivalent of a week-one order slip is the grocery store route mandated by Google Maps. If you avoid challenging these assumptions you might find yourself using pale tomatoes and microwaving take-out because the farmer’s market stayed out of sight. Start a novel and the first thousand words dictate a voice that will either invite exploration or box you in. Skip those starter habits and by day one-hundred-one the half-finished chapter haunts your desktop like that audiobook you never finished.

The plan matters, yet the order in which you place your bets matters more. A hundred days is enough time to watch small inputs compound into culture, balance sheets, or manuscripts. Watch those first slips on the table and insist on clarity. Whether it’s classrooms or boardrooms, that is how you keep the cardboard supply chain from buckling, and how you give a new chapter the stable footing it deserves.

Subscribe now

My professor recently forwarded a note to the cohort: “New research from MIT Sloan documents the ‘WBB’ — Worse-Before-Better — dynamic in AI adoption by firms … and, as our framework predicts, the depth of the ‘worse’ period is larger for older, less digitally mature organizations.” The article traced tens of thousands of U.S. manufacturing plants from 2017 to 2021, finding that productivity slipped 1.33 percentage points on average after an AI rollout, and ballooned to nearly 60 points once the authors corrected for optimistic self-selection. The valley, it warned, yawns widest where routines have calcified. I skimmed the email twice, felt the curve settle behind my eyes, then let the message sit in my inbox like an uncashed check.

Later that same day a close confidant, the former head of R & D for pharmaceutical interventions whose therapies have saved more lives than I will ever meet, forwarded Ethan Mollick’s Substack dispatch, “The Bitter Lesson versus The Garbage Can.” Mollick paints organizations as “chaotic garbage cans” where problems and solutions collide at random and recounts a CEO who, after seeing a true process map, put his head on the table and groaned, “This is even more fucked up than I imagined.” Sutton’s Bitter Lesson — AI self-learning outpacing hard-coded human expertise — hovers over the anecdote, and my confidant’s note in his email seals the point: “My bet is on the messy model.” Different inboxes, same crooked “U.” Time to cash that check.

If artificial intelligence will stumble, plain old operations has been paying the fare for years. Since turnaround specialist Brian Niccol slipped into Starbucks’ corner office last September, the coffee giant has been tearing up its playbook: paring menus, redesigning stores, and unleashing “Green Apron Service,” a hospitality drill that vows 80 percent of drinks in under four minutes that will march through 11,000 U.S. shops by mid-August. Two-day rallies for 14,000 managers, thicker staffing rosters, and wage bumps north of half a billion dollars are part of the tab. So nobody attuned to the WBB curve should flinch at this quarter’s headlines: U.S. traffic down for a sixth straight quarter and net income plunging 47 percent to $558 million. The J-curve is simply doing its job.

Subscribe now

The landmarks of that valley rarely change. First comes the honeymoon, a rollout party with glossy forecasts. Next arrives the ugly middle, when legacy and pilot run in parallel: two billing systems, two recipe queues, two mental models tugging at the same bandwidth. Costs double, throughput stumbles, and morale frays. Only after yesterday’s workflow shuts down while new muscle memory takes hold does performance climb toward the far rim.

Why do managers keep falling to greater canyon depths than could otherwise be expected? Three culprits surface again and again.

• Learning-curve overhead swallows hours that never appear on a blueprint.

• Resource cannibalization forces teams to bankroll both the old and the new until the switchover is safe.

• Cultural drag keeps bright people welded to familiar tools long after the upgrade is live.

Scholars have also mapped ways out of the canyon. Nelson Repenning and John Sterman (two leading researchers in this area I’m lucky enough to count as my professors) show that leaders under quarterly pressure often cut the very training spend that would shorten the slog. They recommend instrumenting the valley with leading indicators such as queue length or cycle-time variance so hidden gains surface before profit does. Erik Brynjolfsson, Daniel Rock, and Chad Syverson describe the Productivity J-Curve, where intangible capital soaks up resources first and shows up in the metrics only later; their cure is to ring-fence capacity so the right-hand ascent is funded rather than starved. Finally, practiced operators storyboard the climb, showing investors the whole “U,” time-stamping milestones, and repeating that the dip is tuition, not failure.

The valley is no shallower for being charted. But a good map steadies the nerves. Wherever you stand on that downward tilt, may the next step tilt a shade higher, and may you keep the budget, the patience, and the curiosity to keep walking.

Share

That night’s mission: whole 2.5 pound lobsters on Boston’s waterfront to kickoff a celebratory weekend for our friend the Graduate, fresh out of his Kellogg EMBA program. Claws snapped, butter pooled like molten gold, and I sheepishly wondered if ordering lamb chops was a regrettable choice. Though being good friends, they passed tender knuckles across the table for grilled lamb the way kids swap baseball cards. Proof, in case anyone doubted, that grown-up friendship still runs on shared mess.

We gathered the next morning at Olde Scotland Links, a public course whose name promises gull cries and crashing waves yet sits beside a commuter road and a 24-hour Dunkin’. The starter handed us scorecards and a lecture on pace of play while a Pepsi machine wheezed behind him. I picked up a grayish (but freshly grilled!) hot dog that tasted faintly of cardboard. Nobody complained because the reunion itself was the condiment.

Subscribe now

My own MIT EMBA lecture notes floated somewhere behind my eyes. Organizational Processes says you learn a company’s cultural soul by seeing what it celebrates; Leading Organizations insists a repair job can be simple: carve a moon-shot into snack-size milestones, then throw a party each time one falls. But theory offers little help when you have just topped a four-hybrid fifteen yards and the townie starter is judging you without blinking.

This weekend’s milestone belonged to one of us: the Graduate. A routine steakhouse toast felt thin, so we promoted the idea to a weekend of golf, reliable weather if mother nature allowed, and something off script (tapas anyone?). Boston rewarded us with one of its few perfect Saturdays: seventy-four degrees and sunny without even the slightest drizzle.

The front nine behaved better than expected. Drives stayed in play, six-foot putts listened, polite barbs skimmed the surface without drawing blood. By thirteen my swing vanished, maybe hiding under a goose-pocked fairway, maybe snickering in a group chat, but the collapse was easy enough to laugh off. Watching someone else find rhythm can be its own celebration; my trench work in the rough simply added sound effects.

Sunday morning had us trading irons for deck shoes. We boarded Adirondack, an eighty-foot schooner built for postcards, and let a patient breeze carry us past the skyline. Sun on the mainsail, salt on our lips, gulls brazen as pickpockets. Conversation drifted from AI in half-baked business ideas to whose slice is more likely to send range balls screaming toward Providence (definitely mine). Mostly we sat still, relaxed, and watched the water do its slow glittering work.

Somewhere between the outer harbor and the turn back to the dock, those classroom theories caught my wandering mind’s attention. Marking milestones is scaffolding, not garnish. Companies tell employees what matters when they stop the workday to applaud. Friends do the same when they carve a weekend out of calendars packed tighter than a TSA-approved carry-on. Personal growth, too, needs a band or at least a kazoo. When you skip the celebratory toast, memory can blur, and morale wilts in the corner like a stale box of factory-made donuts.

We eased into the slip, sails flapping themselves quiet. Clubs thudded into trunks, sunscreen odor clung to fabric, and a mild sunburn made an imprint of my sunglasses. We promised another round soon, and returned to the click of keyboards and calendar invites. Two days later, fishing for a charger at the bottom of my carry-on, I found a bright-orange tee, scuffed and bent, proof that it all happened.

Look at your own calendar. A colleague finishes a certification next month; a friend achieves a new personal best at the 5k; maybe you finally ship that side project. Pick a date and gather the people. It need not involve schooners or oversized shellfish. Though both help.

Share

Yara
Norway’s fertilizer giant woke in February 2022 to find half its customers under shellfire in Ukraine and the other half boycotting Russian phosphate. Imagine planning Taco Tuesday and discovering the grocery store is out of tortillas, beans, and electricity. European gas prices spiked fifty-fold—yes, fifty—and “just-in-time” suddenly read “just-in-case-you-enjoy-bankruptcy.” Headquarters tossed the playbook to regional managers, who did what competent New Englanders do in a nor’easter: swap ingredients, beg neighbors for supplies, and keep the kids fed.

Subscribe now

Lime
Calamity struck the e-bike and scooter company in in March 2020. Revenue for its e-bikes and scooters fell ninety-plus percent, which for the CFO meant “we’re about to hold meetings in a cardboard box.” New CEO Wayne Ting drew three circles on a whiteboard: durable hardware, data-driven ops, city relations. Then Marie Kondo’d every budget line that didn’t live inside those circles. Head count shrank, fresh cash came in, and the company survived long enough to claim it had always been about sustainable urban mobility instead of joy-rides for brunch.

Uber
Uber’s train wreck, by contrast, was entirely homemade. In 2017 a gush of scandals (harassment, “toe-stepping” gone feral, regulators banging down doors) turned the brand into a case study for top business schools. Enter HBS professor Frances Frei, who found brilliant engineers running a frat house. She forced managers through thirty hours of “how not to be a jerk,” let employees rewrite the values, and finally sent the company to etiquette class. Today, Uber is finally showing sustained profitability. Cue the saxophone solo.

Three takeaways:

1. Push decisions to the front line. Whether you’re running friends-giving or organizing a nonprofit fundraiser, the person closest to the action spots problems first, so trust their judgement.

2. Practice before improvising. From fire drills to spare batteries or dry runs for new dance moves, rehearsal buys you seconds and confidence when things go sideways.

3. Know why it matters. A mission with real teeth helps teams stomach detours, budget cuts, or PR nightmares.

All of this leaves me with more questions. Does this jazz doctrine work in fields where mistakes get people killed, like aviation or hospitals? How do leaders know whether a fumbled chord can be rescued or the band should just stop playing? How often must companies rehearse the apocalypse so the first drill doesn’t feel like the actual apocalypse? No matter how many times we face the same problems, flexing our muscle in response to them can always be challenging.

Share

The Google Drive for our upcoming September wedding currently resembles an overstuffed keepsakes box. Full of mismatched files and folders labeled “Possible Centerpieces v7,” “Piano or String Trio?”, and “Chicken?”, each one a rabbit hole we’ve tumbled down as life’s regular obligations pile up around us. The catering menu presents unexpected challenges, such as whether Philly-cheesesteak egg-rolls at cocktail hour can really hold up to a pairing with top-sirloin au poivre as an entrée. Pinterest lingers in the background to give endless grids of inspiration that feel more like photo albums for parties I haven’t been invited to.

In many aspects of life, we’ve learned to lean on recommendation algorithms out of habit, grateful to have something just to “throw on.” Yet lately the convenience feels flat, like lukewarm instant coffee beside a fresh espresso. Spotify recycles the same 30 songs on your hyper specific “cowboy sunshine indie road trip” daily mix. Same cymbal crash, different day. Netflix lines up reco’s in thumbnail form, hoping we click, but rarely do. A 2024 analysis from Luminate’s Streaming Report found that the average listener skips a song before the thirty-second mark. Abundance, it seems, can dull appetite. That impatience lives in my thumb every time I hammer ‘next’ hunting for a show to watch. In an age of algorithmic overload, what can be said about the importance of good taste?

As our wedding date draws nearer, the band we hired sent over a template to help finalize the finer details. Staring at its vacant rows felt like peering into a void that somehow expected a perfect soundtrack from me. I wanted every song that once blasted from tinny car speakers on teenage summer nights, every melody that had stitched itself to a chapter of our story, yet I also wanted each guest to feel as though the set list had been tuned to their pulse. I peppered my fiancée with rapid-fire questions—Was “Mr. Brightside” too on-the-nose? Would my family actually dance to Phoenix?—until the task outgrew the moment and started nibbling at our patience. The recessional, that single walk back up the aisle, felt especially important: it had to avoid wedding-playlist cliché, respect the ceremony’s gravity, and elicit joy. Spotify and ChatGPT lists only multiplied the possibilities, each suggestion convincing me we were missing a better one just out of frame. After an hour that felt like three, we knew we had to move on and hope we’d come up with something better later, a tried-and-true strategy for tastemakers.

Share

Imagine the relief I felt when a few weeks later our wedding band’s lead singer offered a single, perfect suggestion for our recessional music. A real human, not a digital hive-mind, had paid attention long enough to offer a choice that made me feel something. It’s what ‘good taste’ can actually mean: sorting signal from noise, turning overwhelm into relief, and nudging a crowd toward shared delight. It’s central to the human experience. It’s how we keep refining the texture of daily life. And when that fine tuned judgement fades, the loudest voice can end up setting the tune. The question isn’t wedding playlists. It’s one of cultivated discernment in an age of abundance.

Some people spend entire careers betting on that compass. Music producer Rick Rubin devotes a chapter of his acclaimed book The Creative Act: A Way of Being (2023) to the claim, “I have no technical ability. I know what I like and what I don’t like. I’m paid for my confidence in my taste and my ability to express what I feel.” Rubin has earned nine Grammys, co-founded Def Jam while still at NYU, and shepherded household names like Johnny Cash, the Beastie Boys, and Adele. In 2002 he asked Cash to pare Nine Inch Nails’ “Hurt” down to voice, guitar, and the creak of a pew, a great rendition that still feels fresh today. Taste, for Rubin, is a muscle built by attention and exercised without hesitation.

If Rubin shows how taste can be inward and spare, John Maeda—former president of RISD, longtime MIT Media Lab professor, and now Microsoft’s VP of Design & AI—demonstrates what judgment looks like when algorithms churn out options faster than humans can blink. Writing in a 2023 Figma essay that distills his annual Design in Tech Report, Maeda warns that “AI promises unparalleled efficiency and limitless potential for creatives. On the other, it threatens to spawn a masterful new generation of cookie-cutter designs that could spell the end of many creative careers.” Speed, in other words, is no longer scarce; meaning is. He adds a blunt reminder that echoes our own playlist fatigue: “The most efficient solution is not always the most creative one… the route of greatest efficiency is rarely the most impactful.” Maeda argues that as software floods the canvas with flawlessly executed variations, designers must trade the role of maker for that of orchestrator. To be the person who decides which one-in-a-thousand image actually matters here and now. It’s the same relief I felt when a very human bandleader, not an algorithm, named the perfect recessional song. One of the important few luxuries still seemingly far out of reach for LLMs.

Enter Alice Waters. The Berkeley, California chef opened Chez Panisse in 1971, seeded the farm-to-table movement, and accepted the National Humanities Medal for melding the ethical and the edible. Taste, she told the New York Times Magazine in a 2021 profile, “is a language of its own; once you learn it, it guides every other choice you make,” and, as she wrote in The Art of Simple Food, when the ingredients truly sing, “you can cook very simply and the food will be extraordinary because it tastes like what it is.” For Waters, taste begins not with seasoning but with the life of the soil and ends with the judgment of the cook. Her writing and activism insist that even a single carrot plucked from the earth embodies dozens of tiny yet critical decisions, resulting in a cumulative act of discernment. Taste, in her hands, is not flourish but foundation.

Different domains, identical pattern: judged attention over raw abundance. Across music studios, design boards, and farm rows, the lesson is clear. Cultivated discernment in an age of abundance hinges on the habit of noticing, the courage to choose, and the willingness to live with the fallout. Rubin’s practiced conviction, Maeda’s orchestral eye, and Waters’s reverence for craft suggest that good taste is an ongoing discipline of noticing keenly, choosing bravely, and sharing decisively. It listens hard, arranges what it finds into something coherent, and offers the result with enough confidence that others can feel it too. Now, more than ever, good taste matters.

Subscribe now

Large-language models have permeated homework assignments, group projects, take-home exams, and every other space where students once wrestled with uncertainty in the pursuit of real understanding. The allure is obvious. Yet the erosion of independent thinking is already dimming intellect in classrooms across the globe. A recent MIT Media Lab study found that when students leaned on large-language models for problem sets, their capacity for critical reasoning eroded measurably within weeks. The Wall Street Journal has chronicled an accelerating spike in generative-AI cheating scandals, with detection software one step behind and policy responses struggling to keep up. Though, frankly, both the AI-doomsayers and AI-evangelists miss the point. What matters most right now is making sure future students aren’t shortchanged by institutional neglect.

Most painfully, inequity is widening. Well-resourced schools are building sophisticated guardrails to integrate these tools thoughtfully. Leaner districts, by contrast, are defaulting to outright bans or chaotic workarounds. The result is a paradox we’ve all seen before: the students who would benefit most from high-quality guidance are the least likely to get it. Underlying this is the hollowed-out transcript, with rows of top-tier grades masking a mind that never learned how to pick apart an argument or build one from scratch. Worse still is the normalization of dishonesty, chipping away at the shared trust that gives academic credentials their meaning. AI use among teens doubled in the past year, according to Time Magazine, but the growth clustered in schools with the staff and resources to shape healthy norms. Where scaffolding is absent, shortcuts are becoming habits.

There is broad consensus that we need strong measures to shape this transition rather than be swept up in it. I see a five-to-ten-year period of reform during which academic curricula, employer hiring habits, and social norms will evolve in response to these trends in various ways. The institutions quickest to adapt to those changes will win. But we also can’t ignore the human cost of that evolution, the students trapped in outdated systems, graduating with a cheapened experience they never chose.

In some places, the realignment has already begun. Employers are shifting focus from reputation to readiness. Recruiters follow simple incentives, shifting toward campuses that incorporate AI as an extension of rigorous thinking rather than a substitute for it. Those campuses will enable their students to flourish in the modes of traditional learning while incorporating AI as a complement. Few signals are clearer than the resurgence in demand for “blue books” reported on by the WSJ.

Large and well-respected universities such as Texas A&M, University of Florida, and UC Berkeley have seen blue-book purchases increase anywhere from 30% to 80% over the last two academic years. Brand-name universities leaning on historical prestige may discover job-market placements slipping, but schools that build a tight feedback loop between classroom achievement and workplace accomplishment could vault into first-call priority for coveted blue-chip internships. Here lies open a window of opportunity for lesser-known niche and regional schools to advance in the rankings.

How do we build classrooms that treat AI as a tool instead of a crutch? First, every student needs baseline literacy in how generative models are trained, where they stumble, and why confident outputs can still be wildly wrong. Second, AI-related competencies would be mapped onto existing courses instead of relegated to a one-off workshop or a new siloed department. Third, teachers should model best-practice adoption of the tools on the planning side while students learn to scrutinize outputs line by line, perhaps through annotated drafts or oral defenses of AI-assisted work (a method many MIT professors currently use). Instructors over-reliant on AI tools for providing feedback will be retrained or phased out by administrators vying for higher placements on competitive school ranking indexes. Pair that with low-tech safeguards (handwritten problem-solving, in-class essays, Socratic seminars) and the machine shifts from brain-rot to power tool. No more threatening than in the 1970s, when calculators threatened traditional math instruction until teachers re-tooled syllabi around conceptual depth instead of manual arithmetic.

Campuses that master this balance will grow more attractive to applicants who want a clear runway to jobs and to employers desperate for capable graduates. Schools that refuse the challenge will watch cohorts slip through their fingers half-formed and lacking any serious level of critical thinking skills. Those unlucky students will matriculate into a labor market that will not tolerate the lack of skills developed from overuse of AI as a permanent crutch. A decade from now, top employers will still be recruiting future employees from the schools best preparing their students for the modern workforce, as they do today. However, this transition period is likely to have a profound impact on which schools are at the top of that list, and what it means to be a top contributor at a modern employer.

I remain a long-term optimist because we’ve been here before. In the 90s, search engines forced writing classes to pivot from memorizing facts to synthesizing sources, and “you won’t be walking around with a calculator in your pocket” was a common refrain from middle school math teachers. We adapted then, and we will adapt now. The next decade will be messy with accreditation fights, shifting rankings, and painful mismatches between student needs and institutional capabilities. But eventually our academic institutions will re-calibrate in a way that continues to advance human development. Our task is to make that happen sooner rather than later, or we’ll watch another generation left behind by failing institutions that refuse to adapt.

Subscribe now

We all occasionally mistake busyness for progress. It feels natural to triage an overflowing inbox, chase down urgent decisions, and fill silence with activity. Yet the most valuable insights I’ve gathered arrived when I stepped away from my desk and let my mind drift.

Research shows that when we give our brains a little room to wander, we're not just zoning out, we're actually tapping into a deeper, more creative way of thinking. When the so‑called default mode network lights up, it knits scattered experiences into fresh patterns. Kary Mullis famously conceived the polymerase chain reaction while driving a winding California road. This idea revolutionized areas as diverse as genetics, medicine, and forensics, proof that a wandering mind can redraw the map of entire fields.

Patience, therefore, should rival urgency. Knowing when to act quickly versus when to sit back and carefully observe is crucial. The difference might seem small, but it's significant: urgent actions can solve immediate problems, yet patient reflection often reveals longer-lasting solutions and ideas. The sharpest thinkers I know schedule time to read, walk, or simply stare out a window, trusting that reflection will pay dividends.

Foodies, writers, even dinner guests thrive on the same rhythm of pause and engagement. Chef Dave McMillan once told Anthony Bourdain on an episode of Parts Unknown how hard he works at being an excellent dining companion: McMillan emphasized the importance of presence and thoughtful engagement, recognizing the effort it takes to prepare appropriately, respond genuinely, and truly connect. Bourdain lived the same discipline, often lingering on the sidelines before he spoke. “Maybe that’s enlightenment enough,” he wrote, “to know that there is no final resting place of the mind; no moment of smug clarity… and how far I have yet to go.” Bourdain understood that rushing through an experience diminished its value, and his writing celebrated patience and attentive observation as pathways to deeper understanding and richer experiences.

Of course, patience taken too far morphs into paralysis. Miss the right window, and opportunities evaporate. The discipline lies in asking one clarifying question: Is this a clock‑speed decision that demands immediate action, or a calendar decision that benefits from another lap of reflection? Pose it, answer honestly, then move. This tension is precisely what makes an interesting life both challenging and fascinating.

So step away from your screens and urgent to-do lists. Take a walk, gaze out a window, or simply close your eyes for a few minutes. Embracing these pauses not only makes you a more thoughtful human but a more interesting and insightful person overall. Allowing ourselves this kind of mental breathing room might just be the key to spotting opportunities, recognizing patterns, and nurturing innovative thinking. Sometimes the most impactful ideas show up precisely when we stop chasing after them.

Subscribe now

Barely twelve hours had passed since wrapping up our board meeting over a dinner in downtown Pittsburgh. A few of us had decided to stay for the U.S. Open and by nine o’clock that morning, it was already sweltering. The hundred-year elms that once threw shade over Oakmont Country Club were gone. I learned they were victims of a course that prizes punishment: “hard usually beats handsome,” or so I heard from a born-and-bred Pittsburgher earlier that week. The renovation toughened the layout and, judging by the sweat stains, the spectators too. I slathered on drug-store sunblock, bought a souvenir cap in a feeble attempt to beat the heat, and refocused on the task at hand. Oakmont is one of America’s most storied tracks. This year marks its 10th U.S. Open, the only major where a weekend-handicap dreamer can claw through qualifiers to face the world’s best. It’s here that you learn fast about making tough decisions.

The day before the Open, a handful of us huddled around a different sort of course map: org charts, key metrics, and Q1 financials that left a few directors uneasy about the start to the year. If ever a board meeting invited finger-pointing, this was it. Instead, management took the blame without flinching. No talk of vague “headwinds,” no gentle euphemisms. They laid out fixes already under way and early signs the business was catching a second wind. A deft way to skip endless questioning over already-made decisions and to keep the spotlight on building potential for a bright future. Though tough questions lingered, like the possibility of stripping a department’s budget to zero in order to rebuild from scratch. All of this made Oakmont feel fitting. In a city that forged steel long before it forged champions, good intentions matter less than grit. Someone has to take the hit, then swing again, harder.

Subscribe now

Back at the course, with the board meeting still fresh in our heads, the company’s senior leadership joined forty-thousand hopeful witnesses to crisp swings and tidy fortunes. Halfway down a long par five, a pro studied his lie, murmured with his caddie, and fired an iron straight into a bunker not ten feet in front of him. I felt bad for the guy, but it’s moments like these that make my own middling game sting less.

Crossing the Pennsylvania Turnpike overpass on our way to the second green, we caught whiffs of warm pretzels and Steel City hot dogs: kielbasa, coleslaw, fries, no ketchup. I risked mild heresy with a swipe of yellow mustard but escaped local persecution. Once at the green, we ran into a fellow investor from yesterday’s board meeting. Conversation drifted from the slow resurrection of the Pittsburgh Pirates to the notion that any dentist with a two-handicap could qualify for this championship. We discussed what it meant to provide real stewardship for a company going through a period of unexpected challenges. Showing up to a board meeting once a quarter is fine for a casual observer. Palpable change comes from tough personnel questions over coffee, the tone set between meetings, and in how you speak about a company when management is out of earshot. “Is that manager really in the right seat?” you must ask yourself. Or is she even really at the right company?

As the afternoon crawled into the nineties, volunteers hawked overpriced lemonade, and the gallery pressed on because people will brave heat to watch pressure find its mark. Boards do the same. We sketch targets on legal pads, knowing reality will redraw them. The value lies in rehearsing possibilities, then keeping your head on straight when the next variable breaks loose. Around here, comfort is optional and resilience is required. Similarly, while the course maps at Oakmont promise orientation among tee boxes, hazards, and walking routes, anyone who plays knows maps guide but never guarantee. The terrain always wins. Companies and boards are no different. Facts are shared, conditions are brutal, and judgment rests on how well you improvise.

And so in the mid-afternoon heat we departed, scattering to airports and hotel lobbies. I saw maybe a dozen swings all day, a fair trade at a crowded Open. Board work teaches you to live with partial views, to focus on angles and outcomes instead of every motion. Besides, I polished off a Steel City hot dog and logged good miles with a team I trust. Tough to beat a June afternoon where even missed swings feel useful, because here in Pittsburgh, hard always beats handsome.

Share

Orlando Bravo, steward of a seventy–odd–company software empire and one of the most successful investors in SaaS, recently told Dan Primack of Axios that Thoma Bravo’s most potent use of generative AI is “summarizing data.” Think about that for a second. He then went further and declared that he sees no application likely to “dramatically affect how we add value.” In reading only for syntax, those quips can glide by. In reading for subtext, it’s a firecracker dropped on a pile of dry brush.

Subscribe now

Within private equity, language is currency. Cheap talk depreciates on contact while credible restraint appreciates in subtle undertones. A billionaire who built his brand on the premise that software pulverizes incumbents does not shrug at transformational technology without considering how the shrug itself will be perceived. Whether that be by rivals hungry for reconnaissance or by limited partners primed to feel either euphoria or regret.

A straightforward reading of the remark says Bravo is merely marking the top of the hype curve, refusing to mortgage tomorrow’s cash flows for today’s demos. Inside operating companies, change travels at human speed: sales teams cling to scripts that have helped them reliably meet quotas; finance chiefs blanch at integration budgets; mid-level managers, tethered to inbox metrics, discount benefits that sit two fiscal years away. Social proof keeps the herd moving together. Temporal discounting pulls expectations toward the near horizon. Availability bias elevates gaudy prototypes over the slow, dull plumbing most generative applications require. Against that cognitive weather, Bravo’s related quip about “evolutionary, not revolutionary” changes in the corporate world functions less as heresy than as prophylactic. Stay calm everyone.

A more skeptical reading of the remark treats the sentence as camouflage. In games where information asymmetry drives edge, first movers in revelation often become first victims of imitation; show your algorithm, lose your moat. A deliberate understatement can serve as decoy, inviting complacency in competitors while capital and code accumulate behind the glass walls of a Chicago data room. Game theory points to this as a form of cheap-talk sandbagging. In the Crawford–Sobel sense, a low-cost signal that nudges rivals’ beliefs without surrendering real information.

Let us look briefly at the public breadcrumbs. A Thoma Bravo managing-partner essay earlier this year argued that network effects now arise from “collective intelligence at unprecedented scale”; Thoma Bravo podcast episodes have wandered into generative AI use cases inside portfolio companies; even their website foregrounds products whose names (AiseraGPT, Copilot) pulse with AI bravado. The dissonance between the marketing trail and Bravo’s Axios interview shrug is striking enough to qualify as evidence of intent.

Now imagine, for a moment, the most plausible projects thriving in the windowless dungeons of the Thoma Bravo back-office laboratories: a private knowledge graph knitting together the revenue histories and churn patterns of thirty billion dollars’ worth of SaaS customers; a portfolio-wide drafting assistant that digests board packets before the analyst finishes her espresso; a simulator that lets diligence teams query alternate pricing regimes the way meteorologists test storm tracks. None of this requires frontier-scale research. All of it requires the kind of proprietary data, cross-company trust, and patient capital a scale-out buy-out platform already possesses.

More intriguing than the machinery is the human dividend each tool promises. Reduce informational noise and you stifle decision fatigue; surface anomaly alerts before monthly close and you weaken status-quo bias; oblige an investment committee to explore bearish scenarios and you chip away at confirmation bias. In that light the code is merely plumbing; the real renovation happens in the habit loops of the people who wield it.

Limited partners, for their part, do not fund algorithms; they fund narratives of risk converted into return. By lowering the reference point—by telling investors that AI is, for now, a note-taking intern—Bravo narrows the band within which disappointment can register, banking goodwill against the inevitable friction of implementation. At the same stroke he denies rival firms the schematics they would need to copy whatever skunk-works engine may already be humming in the server closet. Expectation management and competitive secrecy, braided into a single sentence.

Whether the shrug reflects caution or stagecraft, a few indicators will resolve the ambiguity soon enough: the career pages that suddenly court data engineers; the CEO LinkedIn posts that casually thank the “shared Copilot team”; the bolt-on acquisitions whose synergies make sense only if a proprietary model is starved for new training fuel. Absent those signals, perhaps the line was nothing but candor; present them, and Bravo’s recent remark will read like the practiced aside of a magician nudging our eyes away from the hat that already holds the rabbit.

Artificial intelligence is the latest chapter in a very old story: confronted with uncertainty, we invent tools to tame it, then renegotiate the trust those tools rearrange. Bravo’s casual aside reminds us that the workshop, not the press podium, determines who gains the next edge. Substance outruns narrative only when the real work hums beyond the reach of click-bait headlines. The question that lingers is less about code than temperament, about what our appetite for crisp declarations reveals about our unease with stochastic reality. Machines can summarize data all they like; the bottleneck remains the human impulse to stage-manage the story.

Share

A Pilgrimage to Omaha

Every spring, chartered jets spill investors into the Great Plains like migrating starlings, all angling for a seat close enough to glimpse Warren Buffett sipping Coca-Cola on the Jumbotron. The scene feels part revival meeting, part stadium concert, and wholly at odds with the messy, fractured world that usually governs markets. It is a testament to our appetite for order that the “Oracle of Omaha” has become a modern prophet, someone we trust to reassure us that compounding cash flows and common sense can still out-run chaos.

Yet the very fervor of this ritual hints at a deeper anxiety. We want to believe that if we repeat the mantras “buy the wonderful company at a fair price,” or “be fearful when others are greedy” we, too, will sidestep volatility. But certainty in investing is a comfort food, not a complete diet.

Share

Before the arena lights and the Dairy Queen coupons, Buffett was a twenty-something rummaging through the bargain bin of American capitalism. In 1958 he zeroed in on Sanborn Map, a once-dominant cartography firm whose primary operations were fading while its investment portfolio out-valued the whole company, without much notice from outsiders. Shares had slid from $110 to $45; Buffett bought aggressively, then engineered a restructuring that unlocked a swift 50 percent gain for his partnership.

Three years later he wrestled control of Dempster Mill Manufacturing, a windmill-and-farm-equipment maker bleeding cash. Installing Harry Bottle as a ruthless cost-cutter, Buffett helped steer the company from unprofitable to solidly cash-generative, sold off excess inventory, and exited with a tidy profit that dwarfed the S&P’s returns for the period.

These were not polite, buy-and-hold gestures toward blue-chip consumer staples; they were deep-value raids on cigar-butt businesses that otherwise would’ve filed for Chapter 7.

By the early 1990s, Berkshire’s engine had morphed from cigar-butt turnarounds to an insurance-float machine: billions in low-cost premiums from GEICO, General Re, and a mosaic of smaller underwriters functioned as an interest-free loan that Buffett could reinvest long before claims came due. The tactic swapped sweat-equity rescues for balance-sheet leverage, a maneuver many retail investors attempt to replicate with margin, though at far steeper carrying costs. Buffett’s underwriting discipline made the float a tailwind; plenty of imitators, lacking that discipline, have watched similar leverage sink them.

Context, Structure, and Luck

Why does this matter now? Because despite the fact that he continues to be praised as among the brightest and most adept investors, the feats that minted Buffett’s legend occurred inside a context that no longer exists.

• Structural edge: He operated through a closed-end partnership that liberated him from the flows and redemptions that plague modern fund managers.

• Market micro-structure: Mid-century micro-caps were thinly researched, letting patient allocators harvest mis-pricings before Bloomberg terminals leveled the field.

• Regulatory climate: Takeovers and activist tactics faced fewer procedural trip-wires, making a Sanborn-style shake-up feasible for a twenty-something with more ambition than capital.

Strip away those conditions and you strip away half the magic. Revering the blue-chip investment style of Buffett (Coke, American Express, Apple) without studying the partnership years is like admiring Picasso’s Blue Period while ignoring the charcoal sketches that taught him anatomy.

The human brain would rather invent causality than concede randomness. Investors amplify that preference into hero worship. A single, successful narrative feels safer than a thousand messy data points, so we elevate the sage and downplay the noisy ensemble of collaboration, timing, and luck. And while patience is often cited as Buffett’s secret sauce, this patience untethered from its context congeals into inertia. Would you rather wait for the next Coca-Cola at 15 times earnings, or roll up your sleeves to fix a broken tool-and-die shop in Nebraska? It’s messy, but it’s where compounded knowledge and capital get forged.

Lessons for the Modern Investor

The question, then, is not whether to mimic Buffett but which Buffett to study. The late-career oracle teaches discipline; the early-career swashbuckler teaches resourcefulness under uncertainty. Most of us need doses of both, seasoned to our own opportunity set.

An honest audit might ask:

• Where in today’s market do neglected assets hide behind stale narratives, the way Sanborn’s securities portfolio hid behind dusty fire-insurance maps?

• Which operational turnarounds can still be nudged back to life with more sweat than spreadsheet?

• How do we balance the lure of “quality compounders” with the reality that edge often lies where headlines and algorithms are absent?

The parallel that most animates me lives in the lower-middle-market private-equity arena, where a mismanaged HVAC contractor in a sleepy Hudson Valley town often trades at an attractive discount. Yet we’re still confident of the cash flow it could generate with sharper pricing, cleaner books, and service techs who show up on time. These businesses are today’s Sanborn Maps and Dempster Mills. Ill-loved, relatively unknown, and occasionally run by the second cousin who inherited the CEO title when the founder retired to Florida.

Public markets have arbitraged away most of the obvious mis-pricings that Buffett once surfed. Private markets, especially below $10 million of EBITDA, still teem with them. I do not aspire to invest the way Berkshire has since it crossed the trillion-dollar-float Rubicon. The S&P is winning that footrace. I do aspire to the earlier playbook. Dig where the analysts are not, roll up sleeves, refit the engine, and let compounding do the work the algorithms cannot yet see.

Beyond the Oracle

Reverence is a fine sentiment, but reverence without context becomes ritual, and ritual without inquiry calcifies into dogma. Better to treat giants like Buffett the way a geologist treats earthen layers: drill down, date the bands of sediment, understand the pressures that formed each vein of ore, then decide what is still minable.

We crave order, yet markets repay those who make peace with disorder; those who can underwrite ambiguity without worshiping at the altar of a single method. That was the real trick of the young Buffett: a tolerance for incomplete information married to an appetite for risk.

The next time the faithful gather in Omaha, consider watching from a distance. Then open the dusty filings of a sub-$100 million industrial nobody has bothered to model since the Great Recession. That exercise will teach you more about risk, process, and humility than any stadium-sized parable of Cherry Coke and compound interest.

Faith, after all, is most productive when it propels inquiry, not when it silences it. The rest is hero worship, and markets, unlike myths, have no obligation to honor our heroes twice.

Subscribe now