Musing on Connective Tissue

Imagine 10 or 100 people describe you, and their descriptions become a word cloud. Now take your word cloud, and compare it to other people’s.

Would we find that the people you spend time with have similar word clouds — similar descriptors, similar nouns about them? Does your cloud sit close to the clouds of the people near you? If so, in what ways alike, and in what ways different? (That’s graphing friend groups or political links in n-dimensional space according to personal traits, as a word cluster of noun descriptors of the person: clustering by cloud similarity and then drawing lines between the points based on social or political ties.)

My bet: people befriend and connect based on proximity. But the friend network is different than the leader. The map of who we like is not the map of who leads us.

Maybe “Yalie” is a noun about you, and a bunch of the people around you are also Yalies. Maybe most of the people you spend time with are quite tall — about the same height. But what about groups with diversities of traits instead: An office might cluster around Yalies but diversify by role: one person described “HR,” one described “accounting,” one described “CEO.” Some friend groups are all CEOs; other circumstances produce diversity. How does that work in an office? In politics? 

I wonder what they’d learn about politics. Is the most successful politician of a group the person who overlaps most with the rest of the group? I wouldn’t think the leader is necessarily the person with the most words overlapping others (because that person might miss a key trait, e.g. the desire to lead). Maybe the person who is friends with everybody is the one with the most in common with everybody. Or maybe the leader’s lowest commonality is higher than anybody else’s lowest (i.e. “The leader is nobody’s stranger.”). It’s got to be more complicated than that, depending on the group structure and incentives and the outsized impact of specific traits like desire for power.

Why I’ve been thinking about this: in a group that I interacted with today, the leader shares the most traits with the other group members. Each bloc shares one of her dimensions. Thinking about the descriptors of these different people and how she ended up being president: she is the person all of these different groups can agree on.

But often the leader of a group is not the leader because they have much in common with everybody, but because they plan things. That’s an interesting difference. The leader of a friend group is not the one most overlapping with others but more likely the one who organizes the events. In her case, part of it is she makes the thing happen — the leadership thing. This differs from the second-in-command, who doesn’t organize people, just makes the wheels run. Doing isn’t organizing.

Does anybody map social groups this way? A thing I’d be curious about: how do the friend network and the leader differ? The mapping half is studied — sociologists call it homophily. The gap between who connects and who leads is the fresher question.

Games Played

The writers missed out by failing to name it, “The Devil Wears Prada 2: The Devil Still Wears Prada.”

The 12 Steps: Not Just for Addicts

Why should addicts get all the healing? 

I went to an AA meeting once to see what the fuss was about. A friend was going and invited me along. (It turns out the only requirement for membership is a desire to stop drinking. I drank for a few years in college, then realized I didn’t like alcohol, so I came along as a member.) The meeting piqued my curiosity but didn’t resonate with me. 

A few years later, I attended another Anonymous meeting of a different type. (A different friend was going.) Then a third type, another few years later. 

It’s shocking to me that the most impactful solution we have to a whole family of physical addictions is psycho-socio-communal-spiritual. That is to say: Alcohol is physically addictive. Why does making amends with other people help heal that addiction? 

The best doctors don’t treat symptoms. They treat causes. Addiction is self-medication. Anonymous meetings and the 12 steps work on that level. 

I don’t buy that you have to do every step of the 12 steps in order. If order were mandatory, I wouldn’t do them at all. I think each step has a key trait (or traits) that, when satisfied, does the healing. Ben Franklin did a moral inventory before AA was ever invented. 

Today I started my step 4 personal inventory. I spent 45 minutes jotting up areas in my life in which I feel angry and unable to let that anger go. I’m “hung up on it”, as the kids in 1972 might say. 

This is to say I’ve admitted I have a problem (just not in that way). A set of problems. A set of regrets that pop into my mind and which cause me to psychologically spasm with deep and profound regrets. 

So, without any obvious addiction that’s sent me to rock bottom, I’d like to do the steps. Specifically step 4 and step 8. 

Step 4: “Made a searching and fearless moral inventory of ourselves.” 

Step 8: “Made a list of all persons we had harmed, and became willing to make amends to them all.”

I think that, to do step 8, I may also need to do part of step 5 (“Admitted to God, to ourselves, and to another human being the exact nature of our wrongs.” [I’m not sure the God part is important. The self and other human may be.]) 

16 months ago, I noticed something I felt a profound regret about. I jotted up a letter to that person in an attempt to mimic these steps (well, technically sending the letter is step 9). I shot it their way. They responded positively. I feel much better now. 

Today, I took step 1. Er, step 4. I skipped step 1. I’ll be the first to admit that’s not a problem.

Performance-Enhancing Drugs Are Fundamentally Good

Chemicals don’t care what you call them.

Performance-enhancing drugs are great. They enhance performance, and isn’t enhanced performance good? 

Look: today I felt grumpy. So Partner grabbed me a pearl tea: sugar, plus a substance the Olympics banned until 2004. Twenty minutes later I was up and rolling, knocking out work I’d been avoiding for three weeks. It got me thinking.

The classifications we give – food vs supplement vs medication vs drug vs illegal drug – are not chemically meaningful. If you eat the vitamin C that’s in an orange, that’s called eating an orange. If you take the same amount of vitamin C in pill form, that’s called taking a supplement. Yet we think about these very differently. The exact same chemical process that ten years ago was called doing drugs is now called “doctor-prescribed medication for sleep” (cannabis). 

Why does our society (all societies?) have these classifications? We want to restrict some behaviors: for the safety of others, for the safety of the individual, or for reasons that aren’t about safety at all.

The biggest not-about-safety category is purity: questions of what a human is, and what appropriate human behavior looks like. So what’s with the obsession with purity?

I’m reminded of a lawyer who built a Supreme Court practice by soliciting: He would identify cases the Court might take, contact the potential plaintiffs to inform them of their potential case, and end up arguing before the Justices. Chief Justice John Roberst pooh-poohed this: “If I’m going to have heart-bypass surgery, I wouldn’t go to the surgeon who calls me up.” 

But actually, wouldn’t you? Let’s run the thought experiment. A surgeon approaches you out of nowhere: “Based on the shape of your face, I know that you have obstructive sleep apnea. I’m a medical doctor. I studied at this school. I’m not some quack making things up: here are the rigorous scientific tests you can take to verify what I’m telling you. And get a second opinion, if you like.” I would think: that’s excellent.

In fact, this is roughly what happened to me before my jaw surgery. After six doctors’ worth of searching, I found Dr. Christian Guilleminault – one of the founders of the field of obstructive sleep apnea, since passed. While he hadn’t found me on the street, his diagnosis was as unsolicited as they come. He looked at my face and said: “I can tell by the shape of your face that you were a rambunctious child.”

What a funny thing to say! 

He followed it up with, “We will send you in for the lab tests, of course, but I already know what they will say.” He then predicted the results, which aligned perfectly when the tests came back a few months later. That’s the doctor I want to hire! 

So much of our restriction runs on purity. But purity is not itself good for the individual. Purity puts the individual into a particular game — a game they can win only by behaving in one specific way, and a game they never asked to play.

The purity game is about packaging. Take virginity, the archetype of purity: a woman who is chaste, who follows the virginal pathway, receives adulation for it. There are other pathways to adulation. Purity just happens to be the lowest common denominator (for women in a specific slice of society). 

I drastically prefer informed consent. The biggest danger with performance-enhancing drugs — with drugs, period — is the unknown unknowns. You have to know and understand not only the limitations of the drug itself, but the limitations of our knowledge about the drug. We do this poorly as a society, because much of a doctor’s job is to demonstrate confidence and instill calm. They act, one could fairly say, like a con man. The onus is therefore on you the patient to work out the actual epistemology of your circumstance. It is frequently much less certain than any doctor, drug manufacturer, or therapist would have you believe.

External games like purity are other people’s scoreboard. Informed consent is your own: you, the substance, and an honest approximation of uncertainty. To enhance performance, choose the right substances. To choose the substance, know the limits of what’s known.

Today I consented, informed, to one highly-caffeinated pearl tea. Three weeks of avoidance, cleared. Enhanced performance. Fundamentally good.

You’re Excellent at Friendship

To learn what you’re good at, ask other people. Even better, see what people pay you for.

Earlier today, I told a friend he’s excellent at friendship. He was surprised. He’d never thought of himself that way. He asked how I knew.

Here’s how: we’d just been talking about his bachelor party, a roomful of strong, eccentric personalities, every one a distinct weirdo, many of whom would never otherwise share a room. He gets along beautifully with all of them. Holding that many particular people close at once takes real skill. That skill is friendship. He has it without knowing.

This not-knowing is common. The people who are good at a thing are often the last to know it, because unmeasured skills are tough to compare. We can check the scored ones, though even there the ego cooks the books: somehow every poker player says they’re at the 75th percentile. The scoreless skills, friendship among them, keep no count we can read. So we stay blind to our placing within them.

Take the word “driven.” I have found the people who call themselves driven to be, more often than not, the lazy ones, using the word as a permit: “I’m usually such a hard worker, so I’ve earned a little time off.” The genuinely hard worker, meanwhile, tends to grind precisely because they’re convinced they’re too lazy. Their self-image points the opposite way from the truth. The person who repeatedly calls themselves happy is trying to convince someone, either themselves or others.

So most of us don’t know what we’re good at. We learn from outside, from what others reflect back, because the trait is relative and others judge it better than we do. The blindness runs deeper than skill: we can’t see our own traits, and those same traits decide both what we’re good at and what’s good for us.

This distinction gets even tougher when adding internal emotions: I’ve been turning this over today because two companies interviewed me. One piqued my interest immediately. The other, once I learned the details, is the better fit. It’s almost exactly what I’ve already done, less of a stretch. (“I’ve done all these pieces, just not in this precise combination”, I told them.) Being more drawn to the first isn’t evidence that it’s the better place for me. Being drawn to something is how marketing wins. My interest is one ingredient. When running the ikigai exercise, “what do I love?” is one question out of four. Love is helpful. It isn’t the whole answer. Yes, everyone needs passion. But passion can’t buy food. 

Here, what I’m good at aligns with what’s good for me, but they’re disconnected from what I’m drawn to. 

The thing you’re drawn to and the label you claim are stories about who you are, and the story is selling something. Identity has a downside we rarely count.

When choosing between passion and survival; when choosing between love or life, it is the martyr who chooses love. We reward the martyr with fame and acclaim. Pity they cannot spend it.

Score is the Thief of Commerce

“To win, score the most. To score the most, stop keeping score.”

Last week, after three days in my metaphorical writing cave, I hollered to Partner, “I know I haven’t been doing dishes. I owe you.” I caught it immediately: “Actually, I think keeping score is bad practice. I take it back.” She laughed and continued on with her day.

I like scores. Keeping score is a clear and straightforward way to understand and compare performance. But sometimes, keeping score can be actively harmful.

Macro scoring enables comparison between multiple options. Micro-scoring corrodes as it leads you to optimize the wrong things. As my family motto goes (it’s intentionally too long for comedic effect), “Before you hyper-optimize a process, be sure you’re optimizing for what you actually want and not a correlate.”

The Bad (Reflexive Scoring)

Should I owe Partner dishes? I was heads-down on work because I spent the previous three weeks coordinating medical appointments for Partner and renovation work for our apartment.

As Middle East history teaches: if you dig back far enough, you can find huge grievances on all sides. Without touching on rightness or wrongness (as I do not have a sufficiently long stick with which to touch), this process does not seem to form stability. And stability is something I would like in my partnership.

Simply: if Partner feels I’m not doing dishes enough, she will say so. If I feel I’m not washing dishes enough, I should wash more dishes.

Score-keeping as a way of digging yourself out of a hole will often lead to resentment of the scorekeeping mechanism (or participants, which is even worse).

The Good (Reflective Scoring)

I once heard a successful startup founder describe his romantic check-ins. He and his wife divide his work into four categories: money earner, father, lover, friend. Rating each on a 1–10 scale, so long as his overall score achieves more than 25 points, he passes. For this partnership, this calculation may solve a real problem: it recognizes a person’s contributions despite changes over time.

This scoring process is a feedback instrument, driven by deliberate weighing of details — not a reflex prompted by momentary discomfort.

The Bridge (Incentive Alignment)

Hourly work misaligns incentives. This structure causes less efficiency and innovation: working faster costs the worker money!

I realized this structure with my $16/hr marketing internship after my sophomore year of college. I automated all my work, and all the other interns’ work. My superior said, “Sit tight and read.” I arrived to work early and left late because they paid me hourly. I was always there to do work if they wanted to give me work. (Now, I would take a slightly different tack: raising this lack-of-work to my boss’s boss. But at the time, I thought arriving early and staying late to maximize my dollars was the standard way to play the game.)

Even if your boss is your best friend, the hourly contract puts you in opposition. The score isn’t a personality conflict; it’s a contract feature. No amount of scorekeeping can account for misalignment.

The Ugly (Anti-Commerce)

Some work should be 90%–10%. In my partnership, Partner captains cooking 90% of the time; I captain travel logistics and social plans 90% of the time. I’m sufficiently capable to create edible food. Partner is sufficiently capable to book flights and schedule with friends. We simply enjoy it less (and are less skilled).

Micro tit-for-tat prevents specializing and trading, which is the fundamental lesson of commerce. So long as we both share the common knowledge that we’re both helping the team, the score is anti-helpful.

When partners are aligned on what they’re moving toward, the allocation can skew without it mattering. Some weeks she does more; some weeks I do. The “oxygen mask before helping others” frame applies: feeding yourself, whether literal food or via nurturing work, isn’t a withdrawal from the partnership — it’s a contribution to it, because your effectiveness is shared.

The reflex inside an aligned partnership imports structural-scoring logic into a relationship that thrives on more flexibility than scoring provides.

The score is the thief of commerce.

The Reckoning (Trust)

Would you rather employ someone values-aligned and unskilled, or skilled but misaligned? For piecework, I think skilled but misaligned. For a teammate, values-aligned. (That said, I am historically incompetent at working with unskilled people.) But I guess that’s still better than someone who will sabotage, even if they do it unknowingly.

Alignment produces trust. A scorecard substitutes for trust, poorly.

Last night, Partner asked me to do the dishes.

Consistency, Consistency, Consstncy

“Every Day” means Every Day! means ¿Every Day? 

I have a motto: Seven days a week means seven days a week. (Except when it means five.) 

I have three categories of “Every day”: 

1. Religious Commitments 

If lightning struck me and I awoke in the emergency room, I would still write every day. 

The commitment is inflexible. The details are wishy-washy. Sometimes “day” stretches into the early morning hours of the next day. Sometimes “writing” means a scribbled sentence onto a post-it note reading “I don’t want to write today.” When I was writing two pages per day for my first book, many days started with writing “I don’t want to write today… I don’t want to write today…” until I got in the groove and shifted to the topic. Most days, I pen and publish a brief essay. 

When I injured my back, I performed a prenatal core workout as my daily 5 minute abs. 

This “every day” works because the requirement is rigid but the goal very easy

2. When 7 = 6 

    I lift weights every day. 

    (Except for ~2 days per week.) 

    I tell myself I lift weights every day. Sometimes this approach is honest: Over the last two months, some weeks, I lifted 7/7 days. 

    The issue: Weightlifting relies on unpredictable activities. How well will I sleep? How recovered will I be? Sometimes, I need a rest day to prevent injury. 

    7 days per week therefore becomes 6. But if I aimed for 6, 6 becomes 5… and 5 becomes 4…  and very soon I’m watching cartoons with Dorito dust on my chest

    This “every day” works because the requirement is flexible but the goal very intense. 

    3. The Failure of Flossing 

    Jeff Foxworthy’s dentist asks, “Have you been flossing every day?” 

    “Not every day…” Jeff admits. “The last time I flossed… You did it!” 

    Most people don’t floss. I don’t brush my teeth in the morning. (I only brush at night.) 

    Turns out I brush in the morning every day the way most people floss every day. 

    Default to Yes

    I experience a large mental cost oscillating about action. 

    Writing 5 days per week is somehow more difficult than 7. If I give myself an out, I consider and negotiate. Instead, I commit and know my category. 

    Seven days a week means seven days a week.

    (Except for the contexts where it should mean five.)

    (Or zero.)

    (Or negative one.) 

    Working to Win the Lottery

    Sometimes, the safe play is the lottery.

    “I’d rather be working for a paycheck than waiting to win the lottery.”

    —Bright Eyes, “First Day of My Life,” I’m Wide Awake, It’s Morning

    There’s a difference between waiting to win the lottery and working to win the lottery.

    Waiting doesn’t make sense: the lottery is a losing proposition. But working to win the lottery? If you can skew the odds in your favor, you can win.

    Upon graduating from college, I reasoned: “I could get a job at a Big Tech Company that pays $60k/year, this year, or next year, or in ten years.” So I started my own business doing what I wanted to be doing.

    I know of two strategies: working for a paycheck, and working to win the lottery. (By “lottery” I mean asymmetric upside, where one hit pays for many misses.) Most people, Partner included, are wired for the paycheck. I’m wired for the lottery. Both can win.

    Most people think of the lottery as riskier. I disagree.

    Here’s the move that separates my thinking from everyone else’s: the safer path is concentrated. You work for a company; that company goes under, you’re screwed. You find a similar company. But what happens when the whole industry goes under? The skills you’ve built might be useless worldwide.

    The skills I’ve built? Not so much — because I’ve had the ability to choose what skills I build. The employee path is actually a concentrated bet on the need for similar skillsets. My portfolio is which skills to build. That, for me, is diversification.

    The risk actually shows up at the intersection between the operator and the game. For me, this isn’t risky. I have savings discipline, deal flow, and a fitting temperament. For someone without those, it would be. We think of risk as the variance in an activity. On the meta-level, it’s more about being fit for the game and playing enough times to outlast the variance.

    Two Paycheck Jobs

    In my life, I have worked two standard, 9-5, knowledge-work paycheck jobs.

    The first: I interned at a marketing agency in NYC the summer after my sophomore year of college. I automated all of my work, then all of the other interns’ work, then my direct superior’s work. When I asked my superior for more work, he said, “Sit tight and read.” So I played games on my computer, peaking at 120th in the world at a card game I liked.

    The second was at a fintech. $175k cash per year. Predictable.

    My first month working there, my monthly burn was 3x what it was the month before. I had been earning $100–150k with my own business.

    It wasn’t the money. It was the perceived predictability.

    The three most addictive things in the world are:

    1. Methamphetamine
    2. Nicotine
    3. A steady paycheck

    What can I say: I wanted to try the drug. I just got my fix and got out.

    The Math

    I keep my costs low. I don’t get much more value from the $50 Chinese restaurant over the $5 basement dumplings. Most of life’s joy comes from experiences and removing friction. I therefore spend money on travel and life infrastructure.

    I lived in a van while building my first business.

    The math: ten months of San Francisco rent = one van. After ten months of rent, you have nothing. After ten months of van, you have a van. (Also nice that I bought it for $12,500 and sold it 3 years later for $19,500. Taught me a lot about macroeconomic waves, too: the van market went crazy during COVID.)

    While living in the van, I squirreled money into early-stage tech companies.

    Natural aptitude matters. If none of my bets had paid off, I would have switched plans. But four $25k bets is only $100k. Which, if you’re making $150k per year and spending $30k, is only 1 year of work to find out whether you have a skill (in my case, the skill is betting on people).

    Bet on People Who Will Win

    I once asked Ann Miura-Ko (a Midas List member and board member of Lyft) whether there was more to investing than finding competent and trustworthy CEOs. I had a hunch that was the whole game. She agreed: yes. But she added that doing it well is not trivial.

    Fun for her to confirm my approach.

    So that’s been my approach. I haven’t bet on technology or the future. I’ve bet on individual people.

    My company was a ghostwriting business. I spent a lot of time living in experts’ heads. Bylines included:

    • Justin Kan (founder of Twitch)
    • Sam Altman (then of Y-Combinator)
    • Ellen Pao (CEO of Reddit)

    During this investing, I also dabbled with crypto. I took the advice of friends, but those friends didn’t have control over the asset. They were speculators. With a private company, I’m betting on actual leadership. Leadership controls the outcome. They’re responsible for everything.

    The lesson: bet on people who control the outcome. Or bet on no-one (the index). Don’t bet on people without control.

    In a gambling sense: I’ve placed four bets on startups, where variance is high and likelihood is low:

    • 1 failed
    • 1 is planned to IPO this year
    • 1 is going gangbusters
    • 1 (the one that prompted this musing) just received a term sheet at 2.5x what I bought in

    When Partner learned that my ~$15k investment was now worth ~$37.5k, she told me: “You’re like an odd sort of couch.” Apparently, most people find coins in the couch cushions, not tech company stock that they haven’t thought about in months.

    It’s the same way I play poker: I find a spot where I have an edge, and I hammer it over and over and over again. Eventually, if I bet the same amount into ten different companies, and a successful company will more than 10x my money, I need to be right more than 1/10 times. (And, of course, not run out of money.)

    Most people either don’t have the resolve or aren’t right more than 1/10 times.

    Different Risk Profiles

    Graduating university, Partner was saving 75% of her paycheck. She didn’t know many people didn’t save at all, and most financial experts only recommend around 15%. She thought what she was doing seemed logical.

    We are FIRE sort of people, just with different risk profiles. Partner enjoys working for a paycheck. I work to win the lottery.

    These mutually-balanced approaches are part of what makes us a good team. When we need to invent something out of nothing, I’m usually team captain. When a problem needs debugging, she’s in command.

    After reading a draft of this article, Partner had this to say: 

    “I think this last part might warrant slightly more space. You’re hedged in a way most people don’t get to be. 

    It’s one thing to take big bets when you’re young and have no responsibilities. It’s that people tend to get addicted to the paycheck when they set their lives up in ways where they feel the need to have stability. They may miss out on being able to use those skills in big-bet ways as they don’t want to risk a loss. It’s also hard to have the mental space and discipline to self-hedge.

    I’m your hedge so you can chase the upside.” 

    One day, my ship will come in. And if not, we’re still happy.

    Do Fewer

    You win by making the right move. You make the right move by waiting for it.

    Before my jaw surgery in 2018, I made too many moves.

    I underwent a sleep study at a facility that allowed me to sleep on my stomach. Obstructive sleep apnea is positional. Bad medical care.

    A dentist prescribed an oral appliance and lied to me about its potential side effects. I wore it. The side effects were bad. 

    A surgeon told me I’d need to fix my deviated septum, so I might as well do it now. Unnecessary surgery. I’d later have maxillomandibular advancement, which would necessitate a septum fix at that point anyway. I had mis-sequenced, again due to bad advice from doctors.

    Six doctors mis-diagnosed or mis-treated me before I found the world’s expert in obstructive sleep apnea. Not himself a surgeon, he sent me to the only surgeon he liked. I had the surgery. It went wonderfully. 

    One quality move would have saved me ten years and six bad doctors, one bad surgery, and one damaging oral appliance.

    I had an insufficient respect for quality.


    A friend has spent the last decade on a large legal case about a contract violation. Ten years, about ten moves. He says most of his days are spent staring at a wall thinking. The hardest part hasn’t been any single move. It’s been the waiting between them — the part where you’re not doing anything visible. 

    It’s easy to get antsy. But the right move at the wrong time is the wrong move. And the wrong move, just to do something is even worse. 

    That’s not laziness. That’s respect for quality.


    Recently, two optometrists told me I should get corneal crosslinking. The pattern-matching said I needed it. Something didn’t smell right. 

    So I went to the actual experts — the ones who’ve seen thousands of patients who look like me over the past thirty years and done seven hundred-plus surgeries on people with my eyes. 

    At the end of this month, I’m flying to France to install permanent contacts. The pattern-matchers were wrong. The real experts were right. The move they suggested would have been unnecessary.

    Refusing a move is also a move. Sometimes it’s the best move.


    When I started freelancing, I asked everyone for client referrals. I had to. I didn’t know who would say yes, what worked, what my rate was, or who my buyer was. This was the explore phase. More information was better.

    By my third set of clients, the machine started carrying itself. My hourly rate was higher than many lawyers’. Inbound exceeded what I wanted.

    The shift on calls was exponential. I had good pre-call materials. I had good post-call follow-ups. The call itself was mostly listening and repeating back what the client had said.

    One call, I was sitting at a kitchen table on mute, pulling funny faces while my then-partner pointed at the phone whisper-yelling, “Pay attention! Focus!” The client stopped talking. I unmuted. I said five words. I re-muted. The client said, “Wow, you really get it!” Then-partner was floored.

    I would tell early-Julian to keep investing in the process. And not to abandon it when he got tired of it — to keep investing, just in a new way. The work shifts from doing more to doing fewer, better. Respect the elegance. 


    Flailing is not testing.

    When I hired my contractor, I went for volume — got fifteen quotes, narrowed them down. The cost of each one coming by was low — just some of my time — so I figured why not. But I wasn’t systematic. A bit more research upfront — learning how the process works, what the categories of contractor are, what the right questions to ask are — would have produced a faster result with fewer visits. 

    Getting a lot of information systematically is a research strategy. Getting a lot of information randomly is flailing. The two feel similar from inside. They aren’t.


    Closing on this apartment took eight months. The required topics ranged from negotiation to financing to weird legal processes to printing documents at 11 PM in rural France. About ten major moves in total.

    Once the incentives were aligned — me, my broker, the seller’s broker — the rest clicked pretty smoothly. The eight months were spent making the right moves slowly, not many moves quickly. And about half of the key moves were me saying no to other people’s requests. At least two of those would have ruined the deal. 


    It’s not about doing less. It’s about doing fewer, where each one is more elegant. Build the system that reduces the steps. Invest in infrastructure. Make the right move when the right move presents itself.

    If “fewer” ever becomes zero, that’s a different problem. This approach won’t fix that one. But it does need fixing.

    Life is full of games. Games require moves. Don’t do less. Do fewer. 

    What If It Were Easy?

    The goal of the game is to do. You do by removing friction. 

    A few years ago, a shaman watched me explain something I was struggling with. Then he asked, “What if it were easy?”

    The friend with me said, before I could answer: “Julian associates difficulty with value.” 

    He wasn’t wrong. I think most people do. We assume that if something is hard, it must matter; if it’s easy, it can’t be the real thing. Cultures everywhere reinforce this: no pain, no gain; if it burns, it’s working. 

    But sometimes a thing is hard because it’s valuable, and sometimes it’s hard because of friction. Both feel difficult. They’re worlds apart. 

    I notice the difference most clearly with games.

    When I’m playing a game I love, three things happen: 

    1. I pay attention without effort. 
    2. I want to improve. 
    3. When it ends, I want more. 

    This feeling – total absorption, no friction between me and the activity – is rare and precious. Most activities require me to push myself to do them. Games don’t. They grab me by my noggin and suddenly I’m along for the ride. 

    A movie buff once told me he loves movies for the immersion. I experience immersion with movies sometimes. With books and theater, sometimes. With games, almost always. That’s information about me, not about games. Games are my art form.

    This week I made a list of things in my day I find unenjoyable. Except for the entries about physical pain, every entry was a type of friction: either current or future. Some friction is necessary as a means to an end (waiting on hold with a doctor’s office). But some of it is inherited assumptions about how a life is supposed to feel.

    If the shaman asked me again today, I’d answer: I think more of it is supposed to be easy. Not all of it. But more than I’ve been letting it be.

    I’m game. 

    The Surgeon Who Quoted Standard Practice

    You win the game by assembling the right team. In medicine, the right team thinks. 

    Before my sleep apnea surgery, I interviewed surgeons the way you interview contractors. Notebook in my pocket, questions prepared, specific concerns about specific structures, specific tradeoffs, and speculation about areas outside of the medical literature. 

    After ten years of complaining about sleep to at least a half-dozen doctors, I finally met a surgeon who lit up when I pulled out the notebook. We were in a teaching hospital; his students were in the room. He went question-by-question with me. He enjoyed the questions the way an expert juggler enjoys a bowling ball being thrown at his head. I pushed him hard. He juggled the chainsaws. We became friends.

    The second surgeon, at a different and widely respected teaching hospital, wore a very nice lab coat and said things like “the standard practice in this scenario is…” She said it several times. When I pressed on specifics, she returned to standard practice. She was pleasant. She was credentialed. She was a pattern-matcher. She wanted me to use a CPAP for the rest of my life. 

    Doctors are often pattern-matchers. You go in with symptoms, they recognize the pattern, they prescribe the standard response. Most of the time this works, because most symptoms are common. The pattern holds.

    The problem is that pattern-matching is indistinguishable from competence until you’re the edge case. And then it’s catastrophically different.

    A real scientist notices when the pattern doesn’t fit. A pattern-matcher doesn’t notice, because noticing would require understanding the mechanics rather than seeing the pattern. The failure is perceptual, not moral. The pattern-matcher isn’t lying and usually isn’t careless — they don’t understand the mechanics of the machine, so they follow the owner’s manual. 

    This is why “they didn’t intend to be malicious” is such a weak defense of anyone in a professional role. Nobody intends malice. Bullies don’t intend malice — they perceive attacks where there aren’t any. Cruel people don’t intend cruelty — they mis-observe what cruelty is (often by thinking they’re acting righteously). The failure of perception is the failure. 

    Optimism is a specific, dangerous version of this. The optimist sees only what’s going right. If their own work is the problem, they can’t see it — and they can’t hear it when other people raise it, because the pattern in their head is: my work is fine. 

    I don’t want a doctor. I want a scientist who practices medicine. Even better: a philosopher who uses science to practice medicine.

    A test: can you break your surgeon in conversation? If they can be broken – if your uneducated mind can throw questions that cause them to buckle – are you really going to trust them cutting into your unconscious body? If a surgeon can’t handle intensity well, do you really trust them with your surgery? 

    After my first six doctors mis-diagnosed or mis-treated my sleep issue, I now attack the ideas of every doctor who consults on my case. If they can’t hack it, I want a different doctor. I didn’t even go to medical school, and you can’t handle me? 

    I may irk some competent doctors who are unwilling to tolerate my approach. I accept this rate of false negatives, since I am happy to travel the country to find a doctor. If I had limited options, I would behave differently. 

    It’s lonely to keep searching for a new doctor over and over again. For one recent medical topic, I’m on six consults and counting. 

    When it’s not a big deal, I don’t fight this hard. But when it is, I’ll keep attacking your ideas, methodology, and approach until I dismiss you or I trust you. 

    Most people fall into the first category. The second category is how I befriended my surgeon. 

    Game on.