I am good at making money. And at the time pro-social tech was my pet obsession, so on paper, a decent fit.

One day, after weeks spent chatting to hundreds of our customers, I presented my findings to the team. I’ll spare you the deets, but the downbeat was:

“Selling to other activists isn’t working. They’re poor and they complain constantly. But selling to businesses is working, so we should drop these sardines and chase whales.”

This sounds made-up, but I can’t overstate how poor a communicator 24 year old me was.

I stood up and armed with a trove of DATA, excitedly walked through how obviously better this new business model was, and how much of a ball-ache the current customers were.

It did not go over well.

They even made this meme about me:

A few months later I was ousted for not being “values aligned” enough.

Load bearing beliefs

It took me way too long to learn:

You cannot argue someone out of a belief that is protecting them from something internally terrifying.

The belief is not there because it’s true. It’s there because it’s holding something up.

Some beliefs are load-bearing.

For the activists I was trying to make rich, the load-bearing belief was: “We need to support other activists because it makes us good people.”

Telling them to abandon their poor comrades and pursue real customers was, in hindsight, equivalent to telling them to abandon the thing that made them believe they were the do-gooder heroes in the dark late-capitalism YA fantasy novel they thought they lived in.

You know what happens when you knock out a load-bearing wall? Shit collapses.

When someone defends a belief with a ferocity that’s wildly out of proportion to the stakes, you might think they’re just confused about the facts (I did).

Usually, the facts are irrelevant.

Arguments that threaten load-bearing beliefs are doomed from the start. If you’re talking about facts, you are not even in the same fucking conversation.

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Quick trauma dump

The activists in the story had a load-bearing belief that’s easy to dunk on, but so did I.

I grew up in the “because I said so” parenting philosophy. No reasons, just authority, the world rearranging itself around whoever held the power that day. As a child, this is terrifying, it means the world is insane and you have no handle on it. So I built one.

I decided that if I could just be right, really, provably, airtight right, I’d be safe. Rightness = safety became a load bearing belief. The argument was how I made an insane world safe enough to live in.

So when I stood up in that stupid co-working space and projected the perfect case on a slightly broken projector, I wasn’t just pitching a new business model. I was running the tried and true safety program I’d been practicing since 7 years old.

And when they didn’t move, when being right turned out to change nothing, I for sure did not get curious. I got louder, harsher, more convicted. Because if a correct argument can’t move people, then MY load bearing belief would have been demolished, and the world WOULD actually just be full of insane people telling each other “because I said so”.

That was the terror my belief was protecting me from: losing the idea that the world answers to reason at all.

I didn’t get ousted for being too based for the commune. I got ousted because my load bearing beliefs collided with theirs.

I was a guy who believed arguments could fix anything, and had to lose hundreds arguments like these for a dizzying variety of silly reasons before I could believe it couldn’t.

The universe has a sick sense of humor.

We all got em’

Now that I’ve given you an uncomfortable look into my therapy backlog, it’s your turn, motherfucker.

Point the principle back at yourself. You have load bearing beliefs holding you back from seeing obvious features of reality too.

You can self-diagnose these if you’ve got the stomach for it by looking for:

• Topics where you stop feeling curious and go contemptuous.

• Issues that feel fundamentally black-and-white / good-and-bad

• Feelings of righteousness you can’t put down without changing “who I am”

These will point you towards your load-bearing pillars.

If you try you’ll find something. A political opinion that you think makes you a good person, the righteous feeling about a former friend who wronged you, some closely held idea about your commitment to integrity, or about being self-made or whatever.

The obvious ones that come to mind probably aren’t quite load bearing. You’d enjoy defending them too much. If you keep looking you’ll find something weird, personal, maybe even extreme.

A real load-bearing belief makes you flinch. Usually, it sits so close to the floor you don’t experience it as a belief at all, you experience it as reality.

And the fact that it’s invisible to you without close inspection and uncomfortable self-honesty is a feature not a bug.

Load-bearing beliefs protect your sense of what makes you yourself and what makes the world feel safe.

Don’t be an asshole like me

So what do you actually do when you, inevitably, have to navigate around other people’s load bearing beliefs?

First, give up on winning. No, not as a tactic, for real. There’s no world where you out-argue someone into safety; the harder you push, the more weight lands on the pillar. What’s on the menu instead is becoming a person it’s safe to be wrong, scared, embarrassed, or uncertain in front of.

Drop the pursuit of rightness, and ask what it would cost them to be wrong. What painful trade would someone need to make, internally, in order to make the update you’re asking for?

That cost is usually a real, powerful fear the belief was built to protect them from. Your job isn’t to attack the belief, it’s to make the fear bearable for long enough for a new perspective to land.

Wanna know why people are so shit-scared of revealing their real, load-bearing beliefs to others? It’s because, for many people it’s immediately followed by being judged. Load-bearing beliefs are personal, paradoxical, strange, extreme, weird, non-normative.

So, to help someone really update a core protective belief, YOU HAVE to make them NOT regret sharing with you. Don’t squirm uncomfortably because you think it’s stupid. Don’t get mad because it’s obviously wrong. I have been guilty of doing all of these many many times, and when people are feeling sensitive, even subtle judgement stands out like a laser in the eye.

Stay, get curious, orient towards being actually helpful.

Questions that make beliefs legible

You can’t blow up a load-bearing belief with arguments. But you can use questions to take the weight off it for a second, long enough that the person can look without the whole structure swaying.

Here’s three I frequently find useful:

“What would it mean if X turned out to be true?” Goes at the fear, not the belief. You’re not asking them to defend the pillar, you’re asking what it’s holding up that’s so goddamn scary. Ask it, then shut up. The answer is the start of an actual conversation.

“Can I tell you why I think this fits with your goals?” Permission is the whole game. A pillar is gripped hardest when it feels under attack, and the fastest way to loosen the grip is to hand them the controls. Half the time they’ll say “go ahead” and mean it, because you asked.

“What makes this one matter so much?” For when the heat spikes way past the stakes. You’re not interrogating the position, you’re getting curious about the temperature.

This ONLY work if you’re actually curious and actually willing to be surprised by the answer. People feel the difference between a real question and a bullshit leading question.

Remember, they unalived Socrates for asking questions like an asshole.

Offer to hold the thing

Once you earn the right to help, you do it by offering to hold up whatever the pillar is holding up.

I’ll look at this hard thing with you. I’ll help you protect what’s important. You don’t have to do it alone, and you don’t have to do it right this moment.

Everyone is standing in a house held up by something they can’t bear to look at directly.

I learned the hard way over and over that being right about someone else’s load-bearing beliefs is the easiest thing. It costs nothing, changes nothing, moves no one.

Being someone they feel safe breaking down their beliefs in front of is the rare and difficult thing.

Only one of those has ever moved anybody.

My good friends in their 40s (roughly ten years older) asked me this recently.

I launched into an explanation about the iconic cultural relevance of Dragon Ball Z (DBZ), the show that basically reprogrammed an entire generation of western children with eastern values. I told them how DBZ’s valued at over $80B+, bigger than some countries’ entire budgets. I monologued on how DBZ lessons transcends class, race, language and culture barriers. Picking up speed, sweating, ranting, I lectured about how it was part of Japan’s genius economic development strategy called “cool Japan” - a multi-billion dollar, decades-spanning psyop by the Japanese government to make their cultural works globally relevant and marketable.

They looked at me like I was an insane person.

“Isn’t it just a cartoon?”

How dare you sir.

---

As a 10 year old watching the DBZ story play out in 30 minute segments after the painful drudgery of school, DBZ taught me about the pursuit of mastery, the moral purity of bettering yourself, the value of teamwork, and the importance of seeing the people around you as your teachers.

This is why DBZ is the most powerful piece of media for a generation navigating an insane world. This is the message behind the millennial instinct to do your best, try to save the world, and always be improving yourself.

So, dear friends who missed out, I’m going to tell you just a bit about the DBZ story. Don’t worry, I won’t make you watch a cartoon.

Just enough to illustrate the impact.

---

So we’ll start here: THE Dragon Balls

DBZ revolves around these things called Dragon Balls. Gather them up and a dragon-genie will grant you any wish.

The bad guys of DBZ are obsessed with the dragon balls to get immortal life. DBZ good guys mostly don’t care about the dragon balls unless they’re trying to revive their friends who died in battle.

And the heroes die in battle a lot.

Pictured above: Iconic good-guy dying scene with its own line of toys that have made more money than most of your friends last 3 startups put together.

Literally every good-guy dies in glorious honorable battle AT LEAST 3 times and has to be revived.

So everyone wants the dragon balls.

This is the first lesson DBZ teaches you as a kid:

Good guys are busy bettering themselves through training and hard work. Bad guys are looking for shortcuts to power.

This guy is our main character, Goku. You have seen him but you don’t know why everyone loves him so much.

Goku is the strongest guy on earth. He’s like superman but instead of having a boner for justice he just loves fighting strong opponents so goddamn much.

He’s an idiot savant for kicking ass. He has a wife and kid or something, but they’re not his main concern.

Note: It takes about 600 more episodes before they actually go fishing.

He is mainly concerned with training every minute of every day to get stronger.

One day, strong aliens start showing up on earth, basically wanting to kill all humans and sell the planet to the highest galactic bidder.

Goku is like “yo, I don’t love the killing all humans thing, but can we get a sparring match in some time??”

This is the second major lesson DBZ teaches you as a kid:

Always improve your craft. Don’t get distracted by the petty concerns of life. Your main goal should be to be the fucking best at your thing.

---

Goku basically immediately dies fighting one of these alien guys.

But the alien uploads the equivalent of a fucking zoom transcript to galactic youtube and now every badass alien in the universe knows about the wish-balls and b-lines for Earth.

So the good guy team gets one year before some sociopaths are going to show up and kill everyone and take the wish-balls.

There’s a lot of muscles in DBZ.

So the good guy team gets to TRAINING. For like, 100 episodes, they are meditating under waterfalls, bulking on alien creatine, beating the shit out of each other to get real strong. Rocky running up stairs montage level shit.

Also, one of them is Goku’s semi-abandoned 3 years old son, because it’s never too early to get SWOLE in DBZ.

This is actually the easy part of the 3-year olds training montage.

Goku, being dead, obviously meets up with God who tells him: “Get to training, my guy.” and sends him to find the afterlife equivalent of Mr. Miagi who can train him to be more badass.

Btw God in DBZ is basically a bureaucrat

This is the third lesson DBZ teaches you as a kid:

There is always someone better than you. No matter how good you get, there’s always more potential you can reach. Always seek out new masters who can take you to the next level.

---

So new scary aliens show up on Earth. The first thing they do after touching down is level a city by basically sneezing. Our heroes are clearly fucked.

Satellite imagery of the sneeze aftermath.

Even with a year of notice, Goku forgets to set a fucking alarm and shows up extremely late to the fight.

By the time he gets revived and shows up to the party, half his weak-ass friends are dead and the other half are missing limbs. It’s a shitshow.

Heroic moment of character growth I don’t have time to explain.

Anyways, Goku has gotten WAY stronger, and he puts up a good fight that basically ends in a draw.

But the nearly-dead-weak-ass friends pull themselves up from being crumpled heaps of broken bones and together they drop a literal bomb of wholesomeness on the strongest alien.

Bad guy realizing hes been fucked by teamwork making the dreamwork

This is the fourth lesson that DBZ teaches you as a kid:

No matter how good you are alone, you need a badass team around you.

---

Finally, before landing the final blow on the sociopath bad-guy trying to escape, Goku begs his buddy to let the bad guy go.

“Bro, wtf are you talking about.”

Goku gives a whole speech about how much he loved fighting this bad guy, and how dope it is that someone so strong exists to push him to the next level, and about how he really wants to square-off with him again.

“Fuck, fine man, your call, you did most of the work to beat him anyways.” and they let him go.

This is the fifth lesson DBZ teaches you as a kid:

Your enemies can be your best teachers. There is honor even in defeat.

Forget the insane details of aliens and wish-balls and all that for a moment.

As kids, DBZ instilled an ethic of honor and self-improvement that makes every startup handbook and self-help guru look pathetic in comparison.

I’ve rewatched DBZ maybe 20 times. Every time I learn something new from it. These are lessons that remain relevant through every stage of life.

No other piece of media comes even close to delivering these messages with so much impact.

Now, please don’t ever say “it’s just a cartoon” again.

Look at this beautiful baby angel.

He is licking his food bowl. He is eating grass. He is looking up at me, pleadingly.

He wants a treat. I have the treats in my hand. “Don’t give him the treat” my husband says, warmly, knowingly, as though he’s really trying to feel compassion for the baby angel looking up at me, but not quite managing it.

Apparently, my baby angel who can do no wrong is too fat. Like a fucking supermodel fasting before a runway show, he MUST cut calories. He MUST???

Are you fucking kidding me?

Are we so tortured by the world that we can’t even let A DOG have the carefree life we secretly wish for ourselves?

My whole life I was told I was making things up. That the food made me sick was fine, actually, and I should be grateful. That the cousin I didn’t want to hug wasn’t doing anything wrong. That my experience was not the basis of my reality.

But I did not make up for my dog’s love for treats, nor the tender ache in my chest I feel when I’m away from my husband who owes me nothing. I did not fucking make up friendship or period cramps or doctors telling me I’m just sensitive.

WE made these things up. Then we decided who gets to feel what things, based on a rulebook nobody wrote down, enforced in kitchens across the globe.

Bentham did not write, “can they reason” but “can they suffer.” I would gently extend it. Can they snack?

No treats? How about:

• No shelter unless you prove yourself worthy through labors of unspeakable drudgery.

• No childlike wonder because it might teach you the wrong lesson about how cruel the world is.

• No care unless you can articulate your pain in a way that doesn’t make anyone uncomfortable.

It’s not not the wellness industry, and the BMI charts for dogs, and the Instagram dog trainers extolling the virtues of withholding care from a creature entirely dependent on you, and the late-stage-capitalism-atomisation of canine joy, and (probably, somehow) the impending AGI.

Here we are surrounded by infinite love, thrown into the future on the sweat and blood of our ancestors with the greatest technology ever imagined. And amidst all that, for some reason, I should withhold a single chicken niblet from the one creature in my life who deserves it most?

My husband is right, of course. The vet is right. He is nine kilos and he should be seven. And yet.

I want to give this angel the life I would have wanted. The life we all deserve.

Let him eat treats. Let him never experience discomfort. Let him know that we are so, so lucky to have him. Nine kilos lucky.

Is that so wrong?

Apparently we are all to sit. To stay. To wait until someone decides we are worthy of the reward of care.

I refuse. I refuse to withhold love, the one thing in infinite supply on this goddamn planet, from the one being who deserves it most, for the sake of a utilitarian ethic.

If a dog cannot experience the full magnitude of abundance, maybe it says less about his worthiness and more about our worthiness of this abundance.

The world could be so beautiful for him. Nine kilos beautiful.

With thanks to Mark Estefanos, for his counsel; to Jonathan, for his patience; and to Matcha the mouse, for his gifts.

Posted with enthusiastic permission from and also the dog, who I gave a treat.

A typical practice session would involve locking myself in a practice room with no windows, setting a timer, pulling up music, playing along, periodically stopping to yelp “FUCK” when I made mistakes.

My fingers knew what to do, did it, and then I’d pack up and go home.

It felt like practice. But I’d never really practiced a single hour in my life.

---

Then I met a very special teacher at an ayahuasca ceremony.

She had been a prodigy, burned out, and now played haunting songs to people vomiting in buckets from sunset to dawn in the hills of privately rented San Francisco mansions.

Over the course of about a year she put me through a grueling practice regimen that was basically starting over from nothing. We went back to the absolute basics. Sitting correctly. Playing one note consistently to a slow ass metronome for a week. Now prove you can do 2 notes at a time PERFECTLY. Now every combination of 2 notes possible. Only 6 months in did we make it to the lofty heights of PLAYING FUCKING CHORDS.

She had a kung-foo master vibe. Showing up to a lesson having not practiced enough was not an option because her vibe was “you will not waste my time”. Scary in a good way.

---

Every practice session felt like torture + bliss. The torture came from every exercise being just a bit too hard. As soon as I would start to master it, I’d move onto the next one which was also just a bit too hard. My wife recalls this time mainly as me sitting just in the next room 4 hours a day saying “FUCK” and “WHY IS THIS SO HARD.” for months on end.

The bliss was the feeling of just barely pulling it off happening constantly.

---

Every really good practice session has this teetering-on-the-edge, torture-bliss bouncing off each other feeling.

Some comparable feelings:

• the word on the tip of your tongue that won’t come, but you can feel its shape

• being on the edge of orgasm

• almost sneezing, but then not

• catching yourself mid-slip on ice, the full-body snap of not-quite-falling

Every one of these is the body suspended between two outcomes, and the suspension itself is the sensation you’re trying to sustain.

The torture-bliss feeling IS NOT “flow”. It’s being almost in the ecstasy of flow, momentarily, then falling out into mundane try-hard-and-fail feeling that makes you yell “FUCK” while your wife is trying to sleep.

There’s endless writing on “deliberate practice” protocols. You can read about protocols. But the feeling you only learn from doing it over and over.

---

Strangely, in the practice regime I felt like I was barely making any progress. But when I’d put it down and play with friends or at a gig, it was obvious I was dramatically more skilled.

When I put the regime down and played, it felt ridiculously easy.

How could I have done TEN YEARS thinking I was practicing something and then be proven so insanely, stupidly wrong by ONE year of real practice???

I am now obsessed with the torture-bliss feeling.

Fuck the guitar. The real thing here is that if I’m practicing anything and it doesn’t have the torture bliss feeling, it’s NOT good practice.

If you’re finishing a writing session, or a yoga session, or an investor pitch, whatever, and you’re feeling competent and pleased, you didn’t practice.

This diagnosis is harrowing.

Once you notice the specific feeling of REAL practice, you can’t help but notice it’s extremely rare and hard to get. You have to go way out of your way to get real practice at anything.

The session that taught you something is the one where you want to yell “FUCK” five times.

---

The torture-bliss sensor I developed practicing guitar is extremely useful in other domains.

The strangest place I’ve felt its readings is in disagreements with my wife.

Afterwards I sometimes wonder: was that a good practice session? Did I manage to get the torture-bliss of being expressive enough to feel heard while being receptive enough to actually listen?

We often debrief disagreements later. “You danced around the thing you wanted to say for a while.” “You could have said the unhinged thing more clearly.” The fine details of disagreement, tuned with autist precision and deliberate practice. Our friends say we deserve each other.

The sensor doesn’t care what you’re practicing. It just tells you whether you were on the edge or coasting.

---

I can’t get comfortable in a windowless practice room without the torture-bliss feeling anymore.

Real practice is rare because it’s exhausting, and once you can feel the difference, the easy version stops being easy to swallow.

The sensor doesn’t turn off. The easy version of practice is gone. I can feel now when I’m getting real practice or just the fake thing I used to mistake for it.

Sometimes I miss not knowing.

I wouldn’t let myself lie down because that was lazy. I wouldn’t let myself slouch because that was sloppy. I would do the steps exactly as presented with memorized precision.

I felt too guilty to do anything else because it seemed like every source agreed these were not The Right Way to do it.

I read dozens of popular meditation books that each claim that they HAVE REALLY LOOKED INTO IT, and FOR SURE this thing is THE ACTUALLY REALLY REAL “thing the buddha taught”. Implicitly or explicitly, the other stuff is fluff and doing it makes you a silly western idiot who can’t hang with the meditation big boys.

So I sat, extremely uncomfortable, and I didn’t move, and I got nothing. And the not-getting-anything felt like my fault, because the books were very clear that the method worked.

It took me an embarrassingly long time to try anything else.

Eventually, on the verge of dropping meditation entirely, I decided “fuck it.” I’ll just try everything and see what works.

This is the exact opposite of what every book told me to do.

---

One time after a long stretch of brutally painful and boring meditations, a friend confided in me that they were on the verge of giving up on the dry, difficult body scanning practice that had been so magical for them on retreat.

I suggested he try loving-kindness meditation, and a week later he reported back saying “dude, that shit is drugs!” He was having fun meditating again, which seems like a win over giving up.

This happens often. A friend gets into meditation for the first time. They heard about it on a podcast and they go on retreat during a mid-life crisis, have their mind blown and then come home to bang their head against the wall until they want to give up.

My advice is always the same: try more stuff.

Before having a reliably good meditation practice, I had to try at least 50+ different approaches. I tried every style of meditation I could find long enough to get the basics, and then asked “does this feel like it’s working for me?” If the answer wasn’t “hell yes” I just moved onto the next thing.

The bonus of sampling lots of practices is I now have an intuition for what will work in different situations and life phases. If I’m having a season of being disconnected, I can turn to loving-kindness. If I’m feeling overwhelmed or sad, I can turn to Jhannas. If I’m going for a walk, I know that non-dual works best.

And trying more stuff is not just about trying more styles of meditation. Try working out first, try weird breathing practices, try a new kind of therapy, dance to Justin Bieber before sitting, whatever.

The response people give to “try more stuff” is usually some version of: “oh. I thought I was just doing it wrong.”

---

The Buddha famously said there’s infinite paths to the goal.

2000 years later, a bunch of people decided what he meant was “actually there’s only one right way and it happens to be my way.”

Meditation is not an elementary school math test where you have to get the right answer the right way or lose points.

So try more stuff. Find what works for you right now. When it stops working, try more stuff again.

The skill is: Productive Delusion

A friend of mine is a ridiculously successful entrepreneur I’ve known since childhood. I’ve watched him fail a dozen times to start businesses. Every time I talk to him about his current thing he has complete confidence that it’s going to work, work fast, with an attitude of “it’s gonna be easy”.

For decades, I’ve watched this play out from up close, sometimes smugly from across the table when he was telling me about his next sure-thing and I was sitting on my high-horse being calibrated and careful.

He was wrong WAY more than he was right. He won the game anyway. He has all the freedom we both dreamed about as overly-ambitious teens. My high horse does not have a sauna, but his second house in San Francisco does…

His conviction isn’t JUST irrational confidence. His conviction is only a super-power because it’s extremely fast updating. He’s 100% all-in on a new marketing strategy. A month later, when it hasn’t worked, he’s 100% all-in on something completely different.

Pro-lusion is really two skills working together: believing harder than the evidence warrants and updating faster than your ego wants.

For us mere mortals, being wrong hurts. Everyone has been told that it’s ALWAYS better to be right than wrong. In most cases, that’s only true if you’re wrong for too long.

If you’re wrong and update quickly, being wrong all the time is a huge advantage.

Productive Delusion: “I’m almost there”

The launch has been delayed three times and now you’re worried about setting a launch date. You’re on your third round of tweaks of the thing, and it’s still not quite right so you feel defeated. The side-project you tried to finish in a weekend is completely broken so you feel disappointed and don’t come back to it for months.

No one stops in the last mile of the marathon. Refusal to look at the gap between where you are and where you need to be means that at every step you’re fully focused on the current action, propelling yourself with the excitement of success, and not distracted by the future.

The feelings that stop people from doing this: worry that you’ll let yourself down again, defeat because it’s not done yet and you have so much more to do, disappointment because the thing is harder than you thought.

Realism: “I have a lot left to do, this might take another year, I should set realistic expectations.”

Pro-lusion: “I’m so close. Not much longer now. Just need to push through THIS part.”

For about 18 months, I studied guitar under a very good teacher with a friend of mine. It was hardcore. I was practicing an average of 4 hours a day. My wife recalls this time as me mostly sitting one room over muttering “FUCK” and “GOD DAMNIT WHY IS THIS SO HARD” over and over. Every week we’d get together to grind jazz songs and he’d say the same thing: “we’re almost there”. This went on for 18 god damn months and it nearly drove me mad.

By the end of it, we were both gigging professionally multiple nights a week.

We were almost there. Then we were almost there again. And again. Eventually, we were there.

Productive Delusion: “This will definitely work”

You have an idea, but you think it’s only 60% likely to succeed, so you invest your energy in a few other places too. You think up a new approach, but the current approach is sort of working, so you keep that going at the same time.

The prolusionary move is committing completely to a path where everyone else would hedge. Doubt is a kind of permission to half-ass the execution; eliminating doubt stops you from half-assing.

The feelings that stop people from doing this: fear of trying hard and still failing, hesitance because previous things didn’t work, dread about having to start over if it doesn’t work.

Non-focus is a hedge. Working on five things in parallel is what people do when they’re not sure any single bet is right. Better to be serially, one by one, completely wrong and to find out fast than to be half-wrong on five things in parallel. The hidden cost of half-assing multiple things is that you’re likely to never know whether the idea was bad or you just didn’t commit hard enough to find out.

Realism: “I’m taking this action but I might be wrong.”

Pro-lusion: “This is the move. I’m all in until it’s clearly not working.”

A friend of mine started a satellite company. Way before spaceX started blotting out the stars with giant numbers of satellites, he was pitching people on the potential of putting basically iphone 5s with solar panels in space.

They had to raise a ton of money, put a shitload of test satellites in orbit, and hire about a zillion engineers, before they had a really profitable business. They had a laser focus on taking a picture of the whole earth every day. This was such an insane thing to try to do in a world where literally everyone was still taking pictures from space with gigantic, multi-billion dollar satellites about once a week.

Over many years, I really didn’t see motivation and confidence falter. There were setbacks like, idk, THE DIFFICULTY OF SENDING THINGS INTO OUTER SPACE. Always matched with a steady chorus of “why don’t you just do the thing everyone else is doing?”, y’know the obvious lower risk, guaranteed revenues option. Undeterred, he’d just talk about how once they achieved the thing, it would work and everyone would want it.

The company went public a few years ago.

Better to be wrong completely than half-wrong about ten things and unsure if you tried hard enough.

Productive Delusion: “This is actually easy”

You start on something and immediately hit roadblocks, so you question your capacity. You find out the best approach is something you’ve never done before, so you make other moves you’re more comfortable with.

The prolusionary move is to just get started doing the new thing, find people to help you, buy courses, whatever. You do all the things you’d do if you believed “if I put some energy in here, I’m sure to figure it out.” The feeling is a kind of confused unbothered-ness. People who do this look at the thing other people are scared of and can’t see what the fuss is about, even when they probably should.

The feelings that stop people from doing this: shame at not already knowing, fear that effort + failure means you actually can’t, fear of starting from zero on something everyone else already gets.

Realism: “This is hard, lots of people fail at it, I should be appropriately humble.”

Pro-lusion: “This isn’t that hard. I just have to do the obvious things.”

At my last company, my employees had a joke that “If you ask him, he’ll just say it’s not that hard.” This was said with a mixed sigh and joviality. I spent 2 years saying: “I’m pretty sure it’s not that hard to automate this complicated finance thing no one has ever succeeded at.”

At my insistence, we tried and failed at this multiple times. When it obviously wasn’t working, we dropped it. On the third or fourth attempt though, we had done enough deals and had enough information to make it work. I led the project, it wasn’t actually that hard (IMO), and we did it.

This became the basis for the company’s whole next phase of growth.

In aggregate, it wasn’t actually easy. But the confusion of trying helped us ask better and better questions until we knew how to make it work.

Observations on Self-delusion and Conviction

If you’re trying to do something hard, you’d guess that being right is really important most of the time. Be careful, know what you’re getting yourself into, say the right things, don’t overestimate.

Most of the time, being wrong isn’t that big a deal. Often, the cost of being wrong is small. But the cost of being uncommitted is big.

This is hard because it involves seemingly opposite attitudes. You have to have enough conviction to focus completely. You also have to care about being wrong enough to minimize wasting time doing something that’s not working.

I can read your mind. You think being careful is good because it increases your chances of taking successful shots. You think I’m overstating the value of action over thinking. You think THIS POST isn’t written carefully enough.

Fine, but try this: believe me more than you should about this, at least until you find out I’m wrong yourself.

Number must go up, and I was responsible for the number.

Every time we would lose a big deal to a competitor, I would seeth with rage, and get another hit of motivation. When I was blocked because a teammate didn’t work fast enough, I’d tighten the anxious ball in my chest, feel a burning glow of desire to keep going, and do the work myself.

Body buzzing, heart pounding, I’d send more emails, arrange more meetings, push more work out.

During this period I was inhumanly productive. We got more funding, and with the fear of running out of money dissipated, I slumped into a profound tiredness that lasted weeks.

While laying in bed for a week to recover, I thought a lot about why I was doing all this shit.

Starting companies is cool, but I’ve never really worked because I wanted to make lots of money. I read the now-defamed Africa-microfinance guy in college and drank the kool aid. My friends were people working on “things that matter”. If someone asked what I did at a party I’d tell them about “The Mission”.

Staring up at the ceiling from my bed mid-afternoon, I caught myself hating the fucking mission. Hating the thousand sales calls. Hating the investor check-ups. Hating my cofounder and hating myself.

The seething when we lost a deal wasn’t competitive fire. It was anger at my own failure to win. The tight ball in my chest wasn’t focus. It was anxiety about letting people down. The 2am emails weren’t passion. They were fear of running out of money.

My dedication wasn’t self sacrifice for some abstract mission statement, it was a raw desire to be acknowledged.

I had been fracking my own anxiety for a decade and calling it ambition.

I was running on internal fossil fuels.

---

Fear, anxiety, frustration are motivational in a very specific way. The mind uses the feeling to cause action by creating pain.

The feeling is the initial spark - the pain/frustration/anger whatever. Then, the desire to relieve the pain creates motivation towards action. The action then relieves the pain temporarily, and the cycle continues.

I’ve spent years meditating to try to get a hold of my internal landscape.

Even so, burning dirty motivational fuels was load-bearing for my whole world- personality, work, relationships, everything. So it was only visible to me when it got to this extreme point.

Seeing the pattern clearly once was enough to make me decide I didn’t like it.

One time, during this initial stage of realization, I woke up normally at 6am and went to get my morning fix of hyper-caffeinated drink and broke down crying in the car in front of the store. The phrase kept replaying through my mind: “I don’t want to hurt myself anymore.”

I then drove home empty handed, cancelled my meetings, and took the day off.

---

The alternative to “dirty fuels” like fear and anxiety is wholesome motivations.

I’m not talking about bullshit wholesomeness like my party-approved “the mission” motivation - that’s typically just coded fear of being small or something.

Wholesome, clean fuels are softer. It’s a measured satisfaction at doing a good job that lingers to the end of the day. It’s the feeling of “I know I did my best, I can learn from this” after something went wrong instead of the furious “next time I’ll win.” It’s the reassurance of “I believe I have the ability to handle whatever comes up” replacing the frantic anxiety to solve a problem RIGHT NOW.

Wholesome motivations also seem to have less “peak” to them. The energy builds and compounds over time instead of being blasted into you when something spikes your cortisol.

So you trade less peak for a higher floor. You do your best and feel satisfied. The next day it’s just a bit better. And so on.

---

Transitioning to clean energy sucks.

The moment you stop feeding the fear and anxiety, the engine cuts out. For me, my motivation and drive initially cratered.

After deciding to go green, I naively thought I’d just feel better about doing the same stuff.I thought clean fuel would feel like the dirty fuel minus the bad parts.

Nope. Instead I often actually feel completely disinterested in the stuff that used to matter.

I’d regularly power up the grindset-machine only to find that it just didn’t turn on. I had to ask myself a thousand times: why the fuck SHOULD I care about sending this email, if not to alleviate my fear of failure?

Try caring about making money. Meh. Try caring about being a good person. Nope. Try caring about the outcomes. Whatever.

I did a thousand experiments like this. Each time I’d ask: why should I care? Is that version of caring just another dirty fuel in disguise? If so, what else could I try?

Eventually I figured out a few things that worked.

Firstly, clean fuels are a fundamentally different kind of thing. They don’t just work right when you need them to. The clean fuel for an email might be something ridiculously slow and complex: “I want to feel the calm satisfaction of knowing I did what was in my power to improve my situation at the end of this day/week/month”.

Secondly, related to the first, clean fuels require different storage and retrieval. To feel the “know I did my best” motivation, could take weeks of consistent plodding effort. Every day, every meeting, every email I would try to summon a tiny version of the feeling. Getting a taste kept me anchored to the bigger version, but was not an easy swap-in replacement for the “LETS FUCKING GO NOW” fire of fear or frustration.

---

All of this trial and error made the transition extremely hard to do while maintaining the same level of performance. It freaked me out for months.

What if this is just who I am now, lazier, less ambitious, less motivated?

The performance hit feels like failure, but I think it’s just the normal response to hot swapping one type of fuel for the other.

There is always the pull back to dirty fuels. New fears quickly replace old ones, vying for attention. What if I’m just lazy now? Is a sneaky example of a dirty fuel getting a rebrand.

For me, fully aborting doesn’t seem to be an option. My body now seems to refuse caring about many things that used to matter deeply to me. But if it was, I think I would have.

A few years into this process, I think the real skill is figuring out how to use both. Sometimes fear and anxiety are appropriate motivators, and you really should use them to take action.

There’s a weird art in getting the hang of deciding to use a dirty fuel, take the spike of energy, take action, and then put it down to go back to a default of cleaner motivations.

I haven’t mastered this yet.

---

Deciding to let go of the whip you’ve been flogging yourself with forever is terrifying.

Many ambitious and successful people I know whipped themselves into a bloody pulp until exactly the moment where they had enough fuck-you money to stop. That’s a rare circumstance.

Rewiring your engine while the machine is still running feels insane. For me it was a last resort. I simply couldn’t keep going in the same way.

If you’re in the middle of your own clean energy transition, doing it because you have to: you are doing something courageous and hard. I hope you can give yourself some grace.

The fear engine stopping may not feel like good news for a long time. But for me, even with my completely imperfect transition only part-way through, I can say that the fear engine failing to start was really the best thing that could have happened.

The transition was very fucking hard (and ongoing), but the ecology on the other side is way more peaceful.

There’s still fear and stress, but there’s more noticing the birds singing, and time with people who love you.

A moment ago she looked at me and asked “So the tax guy got back to us, he said that we’re going to want to file a…”

Holy shit I want to die.

I love my wife. And I don’t want to die, really. I just hate admin. And emails. And taxes.

But the tax bastard has emailed my wife and now I am in an infinite tunnel of suffering while my wife casually sips chamomile tea and assaults me with the untold horrors of forms to be filled and something I only blurrily remember about a deadline.

This flinch happens more and more the older I get. When I am bored, my body tightens. My breath gets shorter. I clench down on reality and my whole mind-body thing says: “make this feeling go away NOW”.

Oh shit, Claude code just said it made a new button… I should make some coffee, or check how many substack followers I got on yesterday’s post.

All of those things are very interesting.

---

I used to think my wife just had superhuman willpower. DISCIPLINE was drilled into me early, in the after school tae-kwon-do class my mom used as daycare when I was a kid.

I treated my emails like push ups. KEEP PUSHING. JUST ONE MORE.

This kind of works. But eventually my arm tired out, and if I didn’t do enough pushups to get the purple belt, a self-loathing would slot in right where the determination was just a moment ago on the mat.

Next time I will be stronger. Less lazy. More disciplined.

But then one day my wife brought up something admin-y (I literally cannot remember), and I engaged push-up mode for as long as I could stand it. Finally I snapped and told her: “I just don’t want to spend 2 hours talking about this stuff every night!”

She looked at me like I was insane and said: “That was 20 minutes”

I argued. We disagreed. The next time this happened though the love of my life who is also a sneaky know-it-all kept a fucking timer going.

Turns out, she was right. I was experiencing repeated, reliable time dilation during any experience like the tax-guy incident.

Ah-ha, something interesting.

---

I began closely observing my wife, and asking rude probing questions to other people I knew who appeared to have this black-belt level of discipline for offensively boring things.

I noticed a few patterns.

Firstly, no one likes admin. Everyone tolerates it. But for some it simply does not cause the infinite pain clenching thing. My wife sometimes describes it as “boring but relaxing”. Pick up your jaw please so we can keep going.

RELAXING???

After much investigation, what is happening here is an incredibly stupidly simple move I have literally never thought of: Focusing less.

The more I paid attention to the feeling I got when bored, the more I realized that my default, immediate reaction to boredom was to focus more. For interesting things, this leads to the transcendent heights of flow. For boring things: infinite time dilation pain tunnel.

So I tried… NOT focusing the full intensity of my attention on scheduling a doctors appointment and navigating 2 different portals with 2fa to get a calendar booking.

I cannot explain to you how to not focus. What I can say is that it drastically changed my experience of boredom.

---

If you are like me, you have a bucket of admin tasks you’re avoiding. I literally have a list called “avoiding list” on my phone.

Imagine the thing you’ve been dodging longest. Now imagine actually doing it, NOT STARTING IT, just actually doing it. How much of your brain power does it actually need?

I hate to admit it, but taxes are not actually hard. They are just fucking boring.

Some things on your avoiding list are probably actually easy. Like, camomille tea sun shining through the window easy. You don’t need a PhD in computer science to organize the hallway closet.

If you’re brave, try setting a timer next time you do something on your avoiding list. You may be shocked. I was.

Fellow avoiders, friends, colleagues, I am here to reveal to you the secret of the organized people:

You might just need to focus less.

---

When I stop focusing at 1000x zoom on the boredom, something completely different comes into view.

Every time the tax guy’s email comes up, when I mentally start looking for the fire exits, my wife is left there, sipping tea, alone in the sun, wondering how long she’s got left before I shatter the window.

I candidly don’t give a shit about being more productive or doing taxes on time. But I care about my wife. I care about her feeling safe. And doing taxes, as it turns out, makes her feel safe.

I somehow did not notice this, really, until I focused a bit less on my pain.

So she finishes her tea. The sun is going down now. We’ve filled out the forms on time. I’m still annoyed. But at least I’m here.

At a former company I ran we had a big well-formatted Google Doc of company values. Countless hours were spent honing our values down to timeless gleaming gems like “honesty and integrity.”

“People-first” sounds like a great value until someone asks for a longer-than-average maternity leave. At which point “people first” rapidly becomes “what does the market say is normal.” When your lawyer and HR consultant are telling you about all the ways comparable company policy analysis says you should not give someone their extra days off, the Google Doc with the overlabored listicle of bullshit values is nowhere to be found.

Almost every org I’ve worked with has one of these horrible Google Docs.

These so-called “values” are supposed to guide decisions, set expectations about behavior, and give permission to push back.

I call bullshit.

In practice, “values” tend to give people a vocabulary for feeling good about doing what they were going to do anyway, and a weapon for prosecuting people who do what they don’t like.

II. Reality Check

I really wanted to believe in values, you know.

I’ve started lots of things, and written an embarrassing number of these values statements. I am a grave offender among the accused here.

The first time I fired someone was a woman who’d joined our team to raise money. She was a very “values aligned” hire. “Honesty & Integrity” and all that. We spoke the same impact sector language, ran in the same circles and she was well known. She was also very expensive.

She turned out to be starting a competitor while on a salary 2x either of the founders had. Oh, and she raised exactly zero dollars.

When we decided to fire her, we knew her fragile ego couldn’t survive a single morsel of real feedback, and so we lied. “We don’t have the budget to keep you onboard anymore, but we really value your contribution and collaboration so much.” Lol. We then lied to everyone who asked why she wasn’t working with us anymore.

We did not lie to spare her feelings. We lied to spare us the potential blowback of having a high-status person running around offended and shit-talking us.

Here’s the test I’ve landed on: a value is bullshit if you can’t name a specific time it cost you something you didn’t want to lose.

Embarrassment and inconvenience doesn’t count. I’m talking about money, status, a valuable relationship, a year of your life. If you can’t produce the receipt, the value is an aesthetic not a position. You’re LARPing it.

III. Five Types of Bullshit Values

Here’s some of my favorite kinds of bullshit values, and how they get abused.

1. Alibi values. Values deployed after the fact to explain what you were going to do anyway. The Google Doc with “Honesty & Integrity” is 40 point font, paired with the quiet decision to withhold, white lie, deflect, get other people to do your dirty work, and use plausible deniability. The alibi value gives you something you can claim to be only in the strictest interpretation. The value doesn’t guide behavior; it’s used for cover.

2. Gotcha values. Values weaponized in disagreements. “One of our values is collaboration,” used mid-meeting to justify why you should do some extra work to make my job easier. “Disagree and commit” used so your boss can tell you “you’ve disagreed enough, now commit”. “Bias for action” meaning please stop asking inconvenient questions.

3. Benchmark values. Values that sound nice, but magically always end up tracking the benchmark of “the market”. “Employees are our greatest asset” until they ask for a raise. “We hire A-players only” but only if they’ll accept the exact same salary as the company on the next floor up. The value holds right up to the point where holding it would cost more than the industry standard, and then it folds immediately in the face of an HR consultant armed with a spreadsheet.

4. LinkedIn values. The socially-required list of good-people values. Always the same Linked-in post-worthy bullshit list: Honesty. Integrity. Hard work. Truth-seeking. These values are a tribal uniform. You wear them because people you respect wear them, and you want to be respected too. They’re so vague and universally accepted, that you probably never actually tested whether they’re yours.

5. Opposite-day values. Values that describe the culture you wish you had, but that everyone knows are bullshit in practice. “Radical Candor” but actually getting promoted requires avoiding conflict with leadership, “Ownership” but everyone knows to never cop to a fuck up. “Flat organization” but actually quiet political games run the show from the shadows. The value tells you exactly what you’re not allowed to be.

IV. The Immense Cost of Bullshit Values

Spending your days performing ablutions to fake ideals damages the people performing them.

Bullshit values are corrosive to an org and to the people inside it.

They teach everyone in the org that words don’t mean things. Each time a value folds, everyone watches. The lesson isn’t that our values are aspirational and we won’t always be perfect. The lesson is that claims by leadership are cosmetic.

They destroy the ability to have real disagreements. Once values are weapons, you can’t argue with someone invoking one without sounding like you’re against honesty, or integrity, or people. So you learn to keep your head down.

They make people cynics. Not just about the company, but about the category of values itself. Someone who watches “people-first” collapse when it matters most will react to the next invocation of that value with an eyeroll, forever.

The cost of bullshit values anywhere is the poisoning of the legitimacy of values everywhere.

The natural next question is: what do values that aren’t bullshit actually look like?

More on that next time.

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I stopped myself from delivering another boring sermon on why he really ought to tweet if he wanted more sales.

As an arrogant prick myself, many times in my life I’ve thought “wow, I know better than this person, I’ll tell them why the thing they’re doing doesn’t make sense.” Sadly, this doesn’t actually work that often. Also, it feels bad for everyone involved.

I try to catch myself these days before going into Sermon Mode, where I’m so sure I’m right that I stop noticing that there is a real person in front of me.

In that beat, he leveled with me: “I just fucking hate doing twitter marketing dude”.

This is a good guy. I’ve watched him give support and grace to his employees when it was very much against his own interests.

In this moment, everyone is pushing him to do something he hates. Another sermon on the virtues of a well-crafted tweet would be silly. So we dropped the pressure and talked.

What he really loved was doing things for his community. Shilling the product was fine, but not the thing that made his heart soar. He loves running events. So we shifted to an events-focused marketing strategy. It seems to be working, but more importantly, he is actually happier, so it gets done with more ease.

This is a risky move. But pushing an agenda onto someone who doesn’t want it is risky too.

I’ve learned a shitload more about life and business from Buddhist texts than from the MBA classes I took at Berkeley, and there’s a sutta that nails exactly the move here.

Sigalovada Sutta (DN 31) - The Buddha meets a young dude doing a prayer ritual. The big dog is not a fan of bullshit rituals. He made this very clear. If anyone has earned the right to go into Sermon Mode, it’s the Buddha. But, he’s clever and sees an opportunity to help someone practically. Cool dude, you’re already doing this prayer thing, why don’t you, like, make it actually useful? He’s cool about it, not condescending.

He reframes each of the six directions as a real relationship. North is your teachers. East is your parents. South is your friends. Each direction becomes a reminder of the concrete duties toward actual people in your life. The ritual stays, but the meaning changes. Sigala walks away with something practically helpful, not a sermon on why his pet ritual is lame.

If you really care about helping someone and being understood, you often have to do this mental jiu-jitsu move on yourself where you drop your own agenda, and follow the momentum to find leverage.

You can sermonize your kid about brushing their teeth, or you can jiu-jitsu them into having a dance party to that one Frozen song you’re completely sick of before bed (which happens to include teeth brushing).

Jiu jitsu isn’t about being stronger than the other guy, it’s about moving in such a way that you get the outcome you want by leveraging what’s already in motion.

Sermon Mode is the opposite.

Think about the last time you felt really right about something. I’ll wait. Got it? Cool.

Be honest, were you in Sermon Mode? Was that the first time you sermoned at that other person? How many times have you explained the same correct thing to the same person who is not going to do it because you keep explaining why you’re right?

I get it, your employee keeps ruining your meticulously organized google drive, your boss is an idiot with a KPI tattooed on his forearm, your roommate won’t stop soaking the god damn dishes and god damnit soaking the dishes doesn’t work anyways!!!

You can only pull the jiu-jitsu move if you accept the other person’s strange alien ways as really actually okay.

No, no, no, I don’t mean quietly enduring while you tap your foot waiting for them to fall to their knees and bask in the pure light of your impeccable reasoning.

This move requires something much more gut wrenching: surrendering the desire to be understood on your own terms.

Btw, the events are off to a good start. Leads are flowing again. My founder friend is happier and I haven’t nagged anyone about twitter in weeks.

Actually helping someone often means surrendering your agenda of how they should be helped.

2500 years ago a random guy was bowing to compass points and the wisest person alive met him there.

What are you doing that’s so important you can’t do the same?

You would not know, chilling on the couch with her watching “Love on the Spectrum” on a Tuesday afternoon, that she can also argue like a pit-bull prosecutor billing by the minute.

One time, she and her husband were visiting. Both were exhausted, trying to plan a vacation at 11pm, when the Sabrina Carpenter mid-show costume change happened. Stage lights go down, and suddenly we’re in a courtroom. The evidence for and against the Lisbon apartment is being laid out in grim detail. Her husband is on the stand, hand on the bible, reciting “I solemnly swear to tell the truth, the whole truth, and nothing but the truth, your honor.”

From the outside, it’s hilarious. From the inside, she didn’t know she’d done it. When I pointed it out, she was stunned. She’d spent ten years of her twenties being a pushy junior lawyer while barely holding her shit together, and now, a decade later, that version of her was still running the show when she got tired enough to go on autopilot.

This is a well known mechanism called “training tired”.

If you take a professional player, rested, they’ll crush free throws all day. If you take that same player, run them until they’re about to vomit, then put them on the line, they will choke way more often. That’s the actual situation in the fourth quarter, when they’re taking the game-winning shot with 2 seconds on the clock.

The sports science term is state-specific learning: the conditions you learn a skill under are encoded into recalling the skill. You don’t just remember the move; you remember the state the move belongs to.

You’re not a pro basketball player, and neither am I.

You are always training something. You don’t get to opt out of the gym.

Every hour you spend dysregulated isn’t lost time, it’s a rep. And if you’re a busy modern person burning the candle at both ends, the reps you run the most are the ones you run in your worst states.

Before I learned about pro basketball training methods, I thought the best move available to being worse when tired was just to be less tired. I have run the Huberman podcast-bro life-hacking thing into the ground. But running a startup, I just did more stuff with my extra energy, and ended up my grumpy self anyways. At one point an employee told me “you need to fix your face in meetings”.

The thing I’d been missing is that there is no off-duty. The “real me” I kept promising people, the one who’d occasionally show up when I temporarily had my shit together, was getting less practice than the tired me, the hungry me, the overstimulated me.

By volume, the version of me that was actually getting trained was the one I kept having to apologize for later.

Call that your Tired Self. Not the worst version of you in the moral sense, but the most practiced version. Your nervous system runs the Tired Self when it’s out of spoons.

Who you are exhausted is often who you are when it matters most.

Moments that matter don’t magically get scheduled on your good days. During a 3am argument with your partner, or when your kid tells you they fucked up after a grueling work day, you have to step up and take the shot, tired or not.

These moments tend to happen when you’re already depleted, already out of regulation budget, and you reach for whatever’s most practiced in that state.

If you’ve been repping your Tired Self for ten years, your Tired Self is who shows up.

You’ve seen this.

The engineer who gets curt and quietly condescends “I think you might be misunderstanding the actual question.”

The manager who goes strategically deflects, “let’s take that offline,” “that’s a great point, let me circle back.”

The parent who gets mean with their kid in a tone they’d never use with a colleague.

The partner who goes cold and quiet and makes you chase them down to repair.

The friend who cracks a slightly-too-mean joke at the exact wrong moment and then gets defensive.

Sorry, sorry, I’m tired, I didn’t mean that.

But you DID mean it.

Or rather, the version of you that’s had the most practice tired meant it. The sorry-sorry-I’m-tired disclaimer is the part where you try to convince yourself that rep didn’t count.

It counted. It’s added to your permanent free throw percentage record because it happened in-game.

My most Tired Self has 2 well-practiced moves:

1) Become a dismissive asshole - “The thing you’re saying isn’t even relevant. Can you try to make more sense or stop talking.”

2) Shut down completely - “I just can’t talk to you right now, please leave me alone.”

Once you see it in yourself, you start seeing it in everyone. It’s a pattern you can learn to recognize in yourself and others. You can watch a colleague get progressively shorter and sloppier over the course of a long afternoon, and you recognize they’ve switched into Tired Self.

So what do you do with this?

Self-help advice won’t help you here. You can’t 30-point-self-care-routine your way out of it. The nervous system doesn’t care about who you are when you’re fully rested. It cares about state-specific reps.

For a long time I thought the highest leverage move was to become the elite version of myself all the time. Always be well-rested, aim for consistent energy and perfect self-regulation. This is how a productivity coded self-help book teaches you to do elite things. Be the A-game version and then play the A game.

But I am almost never that person and neither are you. The version of me that actually shows up to much of life is stretched thin, a bit hungry and underslept to meet a deadline.

If I’m waiting to train my real self until conditions are perfect, I’m basically never training.

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The reps that build muscle in the gym are the ones at the end of the set, when you’re straining to maintain your form. The shaky last rep IS the workout.

Being tired and almost snapping, then catching yourself at “only half snapped” is major success, not a half-failure. It’s the rep that counts most. That’s the moment you actually enter the optimal training ground. Even 10% better when exhausted is enormous, because that’s where things that matter most often happen.

When I grokked this, I started trying to train myself to be better specifically when tired. I developed a little routine where between meetings I’d ask myself how tired I was. I started mapping different levels of fatigue and what behaviors shifted in those stages. With that information in hand, I started deliberately practicing ridiculous-but-effective new habits like “remembering my goals and authentically smiling when on calls” even if I felt like dying.

This is deliberate practice specifically geared towards tired reps.

If this sounds like a lot of work, then you’re understanding correctly. You don’t go pro by getting good at free throws in the gym, you do it by sinking shots in the fourth quarter while your heart is pounding in your eardrums.

So pay attention. The worst version of you is the one getting all the practice.

If you have seen his reviews online, or watched a few of his videos, you might decide that Cole Gordon is a goddamn scammer.

Fair enough, he is the king of the salesmen, and he sells SALES TRAINING.

When I first ran into Cole Gordon, it was on the recommendation of a smart friend. As a budding sales-bro, freshly clad in my first collared golf shirt, running a newly started company, I was struggling to sell.

When I got sent Cole’s stuff, I got the icky feeling. This guy seems… so salesy… But I needed help, and I trusted my buddy.

I paid Cole Gordon $15k for sales training. Actually, I paid that for access to a bunch of videos on his website, and a 30-minute coaching call once a week. Signing the contract, I was kind of sure I was being scammed.

I made my money back in less than a month. His shit worked.

A lot of what I learned from marketing and selling stuff for years thereafter was that my taste was blocking me. The ick feeling was everywhere, and every time I cut through it I made more money.

I thought that people should understand the product before buying. The product was good, and I cared that people on the other side of the phone understood that we were using the good taste I’d invested in.

This completely failed. What actually worked was doing stuff that looked a lot more like Cole Gordon’s tacky-seeming sales tactics.

He was doing these things because they work, not because he thought a camera pointed at his face in a bedroom and a screenshare of a google doc was the height of video production.

Why Taste Lies

Cole was the first version of a lesson I’d see in every domain I cared about. The question that stuck with me after he made me my money back wasn’t why did his stuff work. It was: why did my taste so confidently reject something that was obviously working?

The ick isn’t aesthetic. It’s a self-protective instinct smuggled in through good taste, so you mistake it for a principle.

Trace a typical version backwards:

I don’t want to come off as salesy →
I don’t respect salesy people →
I don’t want people to feel about me the way I feel about them →
If I don’t do salesy stuff, I don’t risk being one of those people →
Not doing salesy stuff is how I protect myself from being rejected as gross.

Over there are gross marketers. Over here are manipulative salespeople. Your taste points at them and says see? I’m not one of those. Meanwhile your actual work sits there, untouched, while you congratulate yourself on your standards.

From the inside, your taste feels exactly like your judgment. The small confident no that’s saved you from embarrassment your whole life is the same no that shows up when you’re about to do something that threatens your self-image. It’s very hard to tell them apart in the moment.

Which is why people with good taste are the most vulnerable to this. If your taste has served you, gotten you work, respect, friends, you have a lifetime of evidence that listening to it is wise.

The better your taste has historically been, the more trustworthy the ick feels.

Tacky is Tactical

The behaviors that actually work are usually just slightly tackier than the ones you’d let yourself do.

A lot tackier is easy to reject. Slightly tackier is the danger zone. Slightly tackier feels like cringe. It feels beneath me. It feels like the thing your taste was built to protect you from.

The people outpacing you in the domains you care about are almost all producing things with AT LEAST slightly worse taste than you’d accept. And the gap is specifically worse in the exact places where your taste is stopping you.

The blunt subject line. The obvious hook. The price that ends in a 7. The post that says the thing straight instead of hedging to save face. The product page with the testimonial at the top like every other product page, because that’s where testimonials go, because it works.

Get Over Yourself

You know this. You’ve watched it happen. The question is why you just can’t get over yourself.

The honest answer, if you sit with it, is almost never because it wouldn’t work. It’s because it wouldn’t be me. Which is another way of saying: I’d rather lose in a way that preserves my self-image than win in a way that threatens it.

So: a diagnostic. Run it on a specific thing, right now, not in the abstract.

What’s the tacky version of the thing you’d ship if you allowed yourself to have slightly worse taste? What would you do if you pushed through the ick?

Pull up whatever you were last avoiding before you opened this. Find the tackier version of it that you already rejected in your head. Feel the ick. Notice that the thing is probably good enough.

If you can’t think of anything, you’re not looking hard enough. Everyone has this list.

It’s the list of moves your gut rejects too fast for your brain to ask hard questions.

Taste is Good, Paralysis is Not

Two caveats, because otherwise this gets misread.

One: taste for the quality of the output is not always the thing to lower. Making good things is good. The taste to lower is the taste for what behaviors are beneath you. Don’t let taste block action that is worth doing.

Two: not all distaste is a cage. Sometimes the tacky thing is just tacky and wouldn’t work anyway. The test isn’t do it because it feels gross. The test is: if I strip away the aesthetic reaction, is there a real reason not to do this? If the only reason is it would feel icky that’s the protective instinct blocking you.

High agency, stripped of its motivational framing, involves the willingness to take actions with worse taste than you think you should. Be awkwardly earnest. Use the strategy everyone is succeeding with even though you sneered at it. Be, occasionally, cringe.

The people you respect who built the things you admire all released things worse than your taste would allow you to right now. That’s not a coincidence.

Lower the bar, do what works, have worse taste.

I’m attending a wedding today btw.

The bridal party groans into a car at 6:30am to go get their makeup done. It’s 90F. The ceremony is at 3:30pm. They’ll spend the day dodging the sun and touching up, trying to keep the expensive paint on their faces intact.

While doing her hair in the next room, my twenty-something cousin lectures me about how old people have lost their sense of childlike wonder. Last time I saw her, she spent 5-8 hours a day “bed rotting” on a family vacation.

By noon, a dozen more vignettes like this play out.

Who are weddings for?

I’m bored and need a project, so I canvas people on the topic throughout the day. The answers are never surprising, but they’re different.

Apparently weddings are for:

• The Bride (who told me last night she is just trying to make it to the honeymoon)

• The Guests (people who expect it to happen, and feel entitled to not being left out)

• The Family (stressed; some arguing about logistics, some avoiding being asked to help)

There’s a DJ looking at his phone while jazz that sounds classy but is actually pretty out-there plays over the loudspeakers. Two coordinators run around with clipboards and fear in their eyes, fake-politely directing bored burly dudes where to put the coffin-sized alcohol fridges.

I think, darkly, as I wander into a church that is both too Christian for half the guests and not Christian enough for the other half: this wedding could have been an email.

I eloped at 24. Got married at a courthouse, had a beer, called it done. 10 years later so far so good.

The Hijacking

The “traditional” seeming parts of modern weddings are barely older than email itself.

Marriage was, for most of human history, an economic and political contract signing ceremony. The ceremony was DANGEROUS. Rivals could block land deals by murdering your son or daughter at the altar.

Bridesmaids matched the bride’s colors not because it was cute, but to act as decoys in case of a kidnapping attempt. Groomsmen were bodyguards. The best man was the best sword fighter you knew. The veil existed so grooms couldn’t bail on arranged marriages at the sight of an ugly bride.

It was fucking metal.

Every element of a modern wedding had an extremely badass function once. All of those functions are dead. The rituals persist because removing them is socially expensive.

Somewhere along the way, the weddings industry figured out it could fill the functional vacuum with a cash extraction machine. Between 1959 and the 1990s, bridal publications went from recommending 2 months of prep to 12, and 6x’d their recommended wedding spend. After De Beers launched “A Diamond Is Forever,” a marketing campaign that basically brainwashed generations of people into believing diamonds were rare and valuable, US wholesale diamond sales went from $23 million to $2.1 billion.

Today, around 67% of newlyweds go into debt to pay for their wedding. The entire middle class has been bamboozled into believing a completely made-up set of traditions is both useful and necessary.

It is neither.

Mo money mo problems

The more money couples spend on the wedding, the more likely they are to divorce. Wedding costs over $20k are associated with 3.5x the divorce risk of weddings in the $5-10k range.

But - inviting more people to your wedding is strongly correlated with lower divorce rates. Honeymoons, regardless of cost, also lower divorce rates.

So the data is pretty clear: if you want your marriage to last, throw a cheap rager with as many friends as possible and then get out of town.

This is not what the industry sells, nor what normie culture expects. It’s basically the opposite.

During the Ceremony

The ceremony today is mercifully brief. People walk down the aisle. The officiant has a football-coach vibe. My grandpa behind me quietly notes that he is not actually a priest.

The spiel is what you’d expect. God, Jesus, support in sickness and health, etc. I’m half tuned out until he says this:

“Look out at the crowd. These are the people who will support you through the years to come.”

I look around. Woah, a lot of people are crying.

This is the first thing all day that feels like it’s touching something real.

The instagram dresses, the piles of expensive gifts, the groomsmens matching leather shoes, are all psychedelically weird to me. But this line pulls me sharply out of the feeling of being in a $40,000 fairy tale.

Here’s a room full of people who showed up. On a Saturday. In 90 degree heat. Dressed uncomfortably. Promising, implicitly, to be there.

The groom cries during his dance with his mom. My wife leans over: “This is what your mom wants.” Probably true.

Weddings, meetings, emails

Earlier in the day I’d thought: this could have been an email.

Tonight I think it’s more complicated.

I’ve sat through enough bloated corporate meetings to have a reflex against performative rituals. Most of them could have been emails. But some of them are doing something an email can’t: making people show up.

An email is cheap to send. That’s exactly why it usually gets skimmed. Showing up, in person, dressed up, on a Saturday, in 90 degree heat, is expensive.

I don’t mean monetarily expensive, I mean it’s inconvenient.

The inconvenience of showing up is the cost of presence.

The real crime of the wedding industry isn’t that it made weddings into silly middle-class rituals. It’s that it convinced people that the most unimportant things about the ritual - the flower arrangements, the schedules and photoshoots, the matching dresses, the whole $40k performance - are worth stressing over for even one minute.

The actually important thing in a wedding is your people come together to witness your commitment, and you feeling the weight of that witnessing. This changes the trajectory of your life for the better.

No one will remember the color of the flowers. I’ve already forgotten the vows.

But I went to a wedding, so I guess now I’m part of team “help these guys figure it out”

When I think about it like that I guess I’m glad it wasn’t an email.

“When we are born into eternity from the womb of time, there will be accountability for our actions.”

This is one of the spooky things my 91 year old grandpa says to me every time I see him.

He is, somehow, still physically strong. Still pottering around his rural house, built decades ago with his sons who now never visit. He’s always just shy of completing the many tasks he feels need doing before he can sell and downsize.

Over the last 10 years, despite his physical ability, he’s started to forget things.

These days whenever we talk, he gives me the exact same speech. I’ve heard it hundreds of times in the last decade. Always near word-for-word identical.

The speech is delivered with quiet intensity and urgency. My eternal soul is on the line, and if he can deliver the speech in just the right way, maybe I will finally listen. Maybe he can save me.

The speech starts tentatively, shyly, expectant of rejection:

“There are things I want to tell you… when I talk about these things no one understands.”

The vulnerability in his voice is overwhelming, he’ll be wringing his hands, leaning in. Redirecting the conversation from this point is futile. Every interjection will be met with a poised waiting to re-enter.

Before the speech became the gravitational centerpoint around which all our interactions orbited, we didn’t just talk about religion.

I think my grandpa sees me as a surrogate son. His father was basically absent in his life. My mom was a single mom until I was 10. He was always around, a mainstay of my childhood and teenage years.

His register shifts briefly to defeated frustration:

“People think I’m talking about religion, but it’s NOT about religion. It’s about the truth.”

As an arrogant teen, I’d argue with my Grandpa hard about the so-called truth.

I’d smugly ask him about the paradoxes of how evil could exist with an omnipotent creator. I’d offer materialist counters to the canonical miracles. Raise historical and doctrinal inconsistencies.

One time I read the bible, cover to cover, so I could argue with him more effectively.

“Our Lord gives us eternal life. I mean, you have to stop and think about that — to live forever and never die in his kingdom.”

I credit my grandfather with a good chunk of my intellectual curiosity. I was a know-it-all kid, surrounded by adults who were often too busy or distracted with making ends-meet to talk deeply with me about ideas.

Except for my grandpa. No matter how much I questioned his fundamental views about reality, he kept talking to me. He kept engaging.

The speech goes on:

“What I’m trying to say is there’s a purpose why we’re here. And it’s not being rich and famous like Elon Musk.”

“Our Lord says something, the evil one contradicts it. So you’ve got this going back and forth. And the battlefield is your mind.”

Strangely, the older I get, the more I find myself agreeing with the speech.

Seek to be good in actions, but also intent. Be skeptical of society’s stories about what matters. Life has deeper purposes. Material success only goes so far towards salvation. Cultivate compassion for people suffering.

I think this is good advice. It’s advice I would give to my grandson if I had one.

After a while, the speech turns somber:

“But my biggest concern is for all the grandkids, you know. I pray for you all every day.”

No one else in my family wants to hear the speech anymore. I get it. It’s tiresome. How many times can you earnestly try to give someone in this loop reassurance, just to be told you don’t really get it?

But I see my Grandpa now, desperate to be listened to, to say the thing in just the right way to be heard. And I see myself as a kid, wanting to be talked to.

The generational transposition is like vertigo.

I try to keep listening in each delivery of the speech. I try to emphasize that I really really am paying attention. I try to reassure him that it’s not lost on me.

The speech winds down with:

“But anyway, maybe one of these days if I’m still around, I’ll tell you some of the stuff that — if you’re ready for it, you know what I mean. And take it seriously, you know.”

No matter how many times I hear the speech. No matter how earnestly I engage. He can’t remember. He always walks away feeling like I never really hear it.

It breaks my heart.

This man inspired me more than anyone else to think about reality, to consider what is really important in life and to be critical about the stories we are told, and that our morals and actions matter.

He did this when everyone else was too busy. He kept talking to me, year after year, even when I foolishly tried to hurt him and tear apart his views.

The last line is always:

“Please, remember to say your prayers”

I will. I do. Thank you.

I am a huge baby about losing anything, ever.

The more I read ancient Chinese philosophy about how to properly place tiny monochromatic stones on the battlefield to crush my wife and win back my honor, the more I realized that Go concepts are weirdly relevant to life.

I lost a lot of games. So, I learned a lot about losing.

I also learned about losing strategically.

When trying to get what you want from other people in life, you will take Ls.

In a negotiation, like in Go, you can make your Ls strategic by anticipating them ahead of time, trading losses successfully, and managing timing to turn losses to your advantage.

Or more importantly, finally beat your wife at a board game to regain your masculinity.

Whichever.

“The greedy do not get success”

This is literally the first rule of a thousands year old master text from before Jesus Christ about a game used to train generals about war and politicians to lead the unwashed masses.

It tells you the best way to fuck up your strategy: Being Greedy.

In working out any deal to get what you want, you probably cannot have everything you want.

How do you know if you’re being greedy? If you’re repeatedly refusing to give the other side real wins, you’re probably being greedy.

Giving up real wins, to be clear, hurts your feelings.

Imagine you’re playing a game against your wife and you’re finally winning after an entire weekend of obsessive studying. You see she’s making progress on the left corner, so you respond, and she demolishes your lead because her tactical game is better than yours.

Shamed, you consider filing for divorce or performing ritual seppuku.

That’s what giving an opponent a real win feels like. That’s why it’s easy to be greedy.

The thing you should have done in that game (you note as you replay the game over and over in your head failing to fall asleep), is let her take the fucking corner.

I have seen this so much. In almost every story of a negotiation that goes off the rails, you will find someone stonewalling, being overly picky about details that don’t really matter, getting in a big-ol righteous huff about “what they deserve”.

You don’t deserve shit. You play some moves and try to get more points. If you’re unfocused you get wrecked.

Being greedy fails because it clouds your focus.

“Lose fights sooner”

In Go, the sooner you accept you’ve lost a fight, the less you typically lose.

A high-level player describes the breakthrough: “I crushed an opponent stronger than me by giving way at every fight… It was all about paying attention to what I could gain while giving up original aims… winning by losing: lose every fight but win the game”

Picture you lost a battle: Idk, say you got told you can’t have the promotion.

Accepting the loss, and moving forward will reduce the damage you take.

You don’t really gain anything by being salty for months that you didn’t get the thing, even if you deserved it. Even if it doesn’t effect your performance, your salty demeanor now gives your boss a reason to be more critical of your work. He will then find more problems, and retroactively use that to justify why you don’t get the next promotion either.

Unaccepted losses compound.

More importantly, accepting the loss early allows you to switch focus to figuring out how to use it to gain advantage in the next round.

An employee of mine once faught hard for a HUGE raise. Unreasonable. She was the best on the team though and she fucking knew it.

We gave her a good raise, but not the XXL pants-suit-made-of-money she asked for.

She said “I’m okay with that, thank you.”

Then she went back to crushing at her job. She waited.

Suspiciously, months later after we had raised more money, she asked again. She mentioned she didn’t get what she wanted before, had done great work since, the company had more resources so the timing was right, and she didn’t want to go looking for other jobs but would if we didn’t give her the raise this time.

Fuck. She got me. She got the raise.

“Be unhurried to enter opponent’s territory”

One time, I was coaching a very smart, but also very dumb, friend of mine through a negotiation with a boss in a tough company.

She felt she was mistreated, maybe had a legal claim, blah blah blah.

The point is she had really good leverage. She talked openly about compensation for her gripes with her boss. It actually went pretty well. He told her he could probably get her at least some of what she wanted.

AND THEY ALL LIVED HAPPILY EVER AFTER….

JUST KIDDING, MOLTOV COCKTAIL

Then, out of spite and principle and rage and stupidity she sent the bombshell email. Every claim she could level against them, every horrible thing she’d witnessed, several larger structural issues she’d flagged previously.

It was a masterpiece of threats and grievances followed by a conclusion that went something like:

“Now give me my fucking money, please”

Her thinking was something like: I told them what I want, and so I should show them all the ammunition I have all at once so they will give me what I want before they push back and I lose any ground.

***SIGH***

Welp, this caused her bosses org to go into a hardcore war footing. Lawyer the fuck up and burn the fields.

She was fired for “unrelated” reasons shortly thereafter.

When you’re trying to get what you want from people, don’t rush in to attack them because you think you might lose something along the way.

You will lose some stuff along the way, sure, but you will probably come out better if you pace your advances.

Giving Up

I hope at this point you are drinking green tea with your pinky up like the Go scholars of yore.

Look, I fucking hate losing.

But getting trounced at Go and doing countless negotiations has taught me that losses are starting points for future victories.

Now when I have to take an L, I try to accept it quickly, and start asking “how can I use this to my advantage”.

This has made losing less painful…

Because I know I can always STILL win.

It’s about getting what you want from other people.

This just so happens to often involve negotiation.

Haggling, the thing most people call negotiating, is just two people barking their positions at each other until one of them flinches and you “meet in the middle”.

You will have seen this shit on Shark Tank.

“125k for 10%”

Cut to close up on Mark Cuban, fingers steepled.

“how about 125k for 5%”

Close up on a hapless mid-western entrepreneur selling a new type of fucking sponge.

“I’m out.”

~~~DRAMATIC MUSICAL CUE~~~

Fuck me.

The Want Behind the Want

Haggling is what happens when you don’t know what the other side really wants.

Figuring out what they want is often harder and more important than knowing what you want.

I don’t mean the bullshit story they tell you. I mean the thing they’re actually secretly optimizing for but won’t say out loud. The want behind the want.

People are usually not going to volunteer this information to you. Why would they? If they reveal your own leverage to you, they give up their advantage.

What they will do, if you are very clever, is give you hints.

You can use these hints to get what you want.

Play the player, not the game.

So, how do you figure out what someone else really wants?

First: Prepare

Before making any moves, you should apply systematic thought to what the other people involved want, and try to figure out what’s most important to them.

This sounds obvious, but is less common than you’d expect.

Systematic thought here means literally opening a fucking google doc (and probably ChatGPT) and for every single person involved researching and writing down:

1. What does their personality suggest they will care about most?

2. What is your best guess about their role, incentives, how they’re evaluated?

3. Anything they’ve already told you / signaled they care about

4. Your best guess about their biggest worries / concerns / fears

I can feel your defeated shrugging.

“Idk what they want”, “I don’t know enough to guess”, “I don’t have any information”, “they have all the power” etc.

This is being lazy. You have the internet and AI. DM me your name and I’ll tell you what you probably care about within an error bar.

The point of thinking systematically about this, and writing it down is so you have some working theory going into your process. You might be wrong. That’s fine.

Something is 100x better than nothing here.

Second: Ask about their goals.

WOAH. Revolutionary. I know. Please send your speaking requests to my agent.

For real though, don’t underestimate the power of directly asking.

Here, I will write some example questions for you so you don’t forget:

“What does success look like for you here?”

“What are your main goals in this process?”

“How can we make this successful for you?”

“What’s the outcome you’re most looking for?”

“What can I do that you think will lead to the best outcome?”

“X months from now, how will you evaluate the success of this? What about your boss/org?”

This is obvious, but it often works.

Sometimes people will just straight up tell you what they want. Take the W.

Third: Ask unexpected follow ups.

Unsurprisingly, directly asking doesn’t always work.

Maybe they don’t know what they want, or they just don’t want to tell you. Mostly, other people will give you a nice sounding pre-rehearsed story that is useless bullshit.

Ie. “I just want what’s best for the organization”, “We think we can have a big impact”, “We care deeply about XYZ abstraction”

GTFOOH.

All good. This is normal.

When someone feeds you a story like this, your next move is: make them improvise.

You do this by asking questions they don’t expect.

A founder I worked with was negotiating his own exit with an investor who was going to have to foot the bill for his exit. High-risk of ending up in a haggling situation.

During a tense meeting where he got a pathetic low-ball offer, he cleverly asked the investor:

“What would your IDEAL ownership percent for me be after this transaction?”

“Uh… well… I mean… Ideal would be less than 5%”

“Out of curiosity, why is that range your ideal?”

“Well, it would make fundraising easier in the future.”

Got him!

The founder wanted freedom, and he needed more money for that. The investor wanted a clean cap table.

Notice here: this gave them a way to avoid the idiotic Mark Cuban haggling dance.

The founder used this 5% number as the basis for everything that came after. How can we get closer to 5%? Well perhaps the investor would have to put in more money, and maybe he’d have to sell for a lower price.

They eventually landed with a deal where everyone was a bit stretched, but also got the real thing they wanted.

Most people will fail to completely hide their true motivation while improvising.

Asking unexpected questions generates hints that you can use to improve your working model of what the other side actually wants.

This is also where the preparation comes in. The founder in the story had done the fucking homework assigned above.

He knew before that meeting that VCs care most about getting to the next round. He had done research and found that future investors get gun-shy if a cap table looks messy. He didn’t really know what “messy” meant, but he guessed that the investor had some unstated goal about ownership amounts.

That was enough. He asked the unexpected direct question aimed at making the investor reveal his unspoken goal.

If you walk in with a reasonable theory about what the other side really wants, you can ask better questions aimed at validating / invalidating your theory.

Rinse, repeat.

Fourth: Tie down

This is a move from sales, but it works well in general. Once you think you know what the other side wants, you confirm it by asking:

“It sounds like your main goal/outcome is X. Is that right?”

If you’ve correctly guessed the other party’s goal, they will often (but not always) find it hard to say no.

If you’re stuck in haggling mode, you can then follow up with:

“If we could get X outcome, would you be open to considering other ways to get there?”

One time I was selling a financial product to a boomer. One thing you learn selling to boomers is they love getting a win in negotiations. These types are easy to beat though, because a win can look like anything.

This guy wanted a discount. “My situation is very simple” (it wasn’t), “It will be less work than your normal client” (it was more), “Can we knock 25% off the price? If so, I’m in”

I hit him with the script.

“It sounds like your main goal is making sure you don’t overpay if you end up having a really easy case, is that right?”

“Yes, exactly”

“Cool, I get that. How about this: if we finish your case in X hours, I’ll give you that 25% discount as a rebate on the back end of the contract.”

“Yeah, that could work.”

I gave him a win. Just not the one he asked for initially.

Winning

The classic negotiation advice is right: you should know what you want.

But in a real negotiation, that’s often less useful than having a strong idea of what they want.

Making demands back and forth to “land in the middle” is what you end up doing when you don’t know what the other side really wants.

But knowing what they really want enables you to build a strong case for why you should get what you want.

Remember: You’re not on shark tank. There are no cameras or stage lights. There’s no dramatic music coming.

Oh btw, the boomer from the story?

He never got the rebate. He also gave us a 5/5 review.

Every year something different stands out.

This year I noticed that Siddhartha Gautama — the Buddha — was running the most sophisticated GTM motion in the history of civilization.

I know this sounds unhinged.

It is unhinged.

It is also the most important business case study you will ever read.

PHASE 1: THE PIVOT

Our guy is a prince. Silver spoon. Corner office in the palace. Clear succession plan. His dad the king has him on the CEO track — attend the meetings, smile at the donors, marry the right girl, inherit the kingdom. It’s the 500 BC equivalent of “my son works at McKinsey.”

But Siddhartha looks around and sees something his dad doesn’t.

Everyone is suffering.

Rich people. Poor people. Young, old, sick, dying. The entire addressable market — and I mean every sentient being — is suffering.

He runs the numbers in his head.

TAM: literally infinite. Competition: a bunch of guys starving themselves in forests who haven’t shipped anything in decades. Customer demand signal: people are dying to solve this problem. Literally dying. That’s the problem.

The opportunity is so obvious it’s embarrassing. He’s looking at the biggest unserved market in the history of markets and nobody — NOBODY — has built a product that actually works.

He is about to become the most elite closer in human history, and he doesn’t even know it yet.

But first, he has a problem.

He has a wife and kid.

Now look. I’m not here to tell you that you should abandon your family to pursue your startup. That’s between you and your therapist and your Series A investors. But I will tell you this: every great founder has made sacrifices that normies can’t understand.

His wife Yasodhara — extremely smart, by the way, they were co-founders in another lifetime — sits him down one day and says:

“You’re going to leave, aren’t you.”

And he says: “Yeah.”

And she says: “Okay.”

According to the texts, they had a deal from a previous lifetime that she would support this move in exchange for exclusive spousal rights across all future incarnations in perpetuity.

This is the earliest recorded example of a vesting schedule with a multi-lifetime cliff.

I cannot stress enough that this is real.

This is canonical Buddhist scripture. The man negotiated an eternal equity stake for his wife across infinite lifetimes to secure her buy-in for one lifetime of grinding.

The cap table on this is insane.

So one night he just walks out. No two weeks notice. No Slack message. No “excited to announce” LinkedIn post. He leaves the palace at 3am, gives away his horse, shaves his head, puts on a robe, and walks into the forest.

Day 1 as a founder.

No revenue. No team. No product. No office. No shoes.

LFG.

PHASE 2: COMPETITIVE ANALYSIS & R&D

First thing any smart founder does: understand the competitive landscape. Maybe someone already cracked this.

Siddhartha finds every major guru in the region and enrolls in their programs. He’s basically doing a speed-run of every meditation accelerator in ancient India. Y Combinator but for consciousness.

And he’s so good at it — so absurdly, annoyingly talented — that every single guru he studies under says the same thing:

“Bro, you should teach this instead of me.”

And every time he says: “Your product doesn’t actually work. No.”

He’s doing competitive teardowns. He’s identifying feature gaps. He is rigorously A/B testing every enlightenment methodology on the market and finding that the entire category is selling vaporware.

At one point he gets so deep into the asceticism niche that he’s eating one grain of rice a day and his spine is visible through his stomach. He’s basically dying. This is the startup equivalent of burning through your runway doing customer discovery and realizing your initial hypothesis was wrong.

Most founders would quit here.

Most founders are not the Buddha.

He looks at six years of failed experiments and says: “The market isn’t wrong. Every existing solution is wrong. I need to build from scratch.”

He sits down under a tree.

He locks in.

—

What follows is the most legendary R&D sprint in recorded history. Forty-nine days under the Bodhi tree. No standup meetings. No sprint reviews. No product manager asking about the roadmap. Just a man, a tree, and the absolute determination to ship.

Mara — basically the final boss of distraction — throws everything at him. Beautiful women (spam leads). Armies of demons (competitive FUD). Existential doubt (investor rejection).

The Buddha’s keeps grinding.

And then he does it. He achieves enlightenment. Full product-market fit. The Four Noble Truths. The Eightfold Path. A complete, elegant, infinitely scalable solution to the fundamental problem of human existence.

The MVP is ready.

The pitch deck writes itself:

Slide 1: Everyone suffers.

Slide 2: There’s a reason for that.

Slide 3: It can stop.

Slide 4: Here’s the 8-step implementation guide.

Four slides. Clean. No “we’re the Uber of enlightenment.” No fake hockey stick projections. Just: here’s the problem, here’s the fix, here’s how.

This is what a 10/10 value prop looks like and most of you will never achieve it.

He takes a seven-day sabbatical to just enjoy being enlightened — the only vacation he will ever take for the remaining 45 years of his life — and then turns his attention to the only thing that matters.

GROWTH.

PHASE 3: FIRST CUSTOMERS (REACTIVATING DEAD LEADS)

Now here’s where most founders fumble. They have the product. They panic. They spam. They post on LinkedIn: “Thrilled to announce we’ve launched 🚀” to their 340 followers and wait for inbound.

Not the big dog. The Buddha knows exactly who his first five users need to be.

And who are they? Five guys who already rejected him.

These are his former practice partners — monks who were doing the starvation thing with him, saw him eat a FULL bowl of rice one day, said “this guy’s lost the grindset,” and literally walked away in disgust.

They are, in sales terms, dead leads. Closed-lost. Marked as “not a fit” in the CRM.

The Buddha walks up to them. They see him coming and agree amongst themselves: “Leave him on read.”

But then he gets close. And something about him is different. He’s glowing. Not metaphorically — the texts say he was literally luminous.

His product demo was his FACE.

They can’t help it. They stand up. They offer him a seat.

He gives them the first-ever pitch: the Dhammacakkappavattana Sutta, the “Turning of the Wheel” discourse.

Mid-pitch, one of the five — Kondañña — just... gets it. Full enlightenment. Right there in the audience.

A PROSPECT CLOSED HIMSELF DURING THE FIRST DEMO.

The Buddha literally shouts “Kondañña knows! Kondañña knows!” which is the 500 BC version of ringing the sales bell so hard it falls off the wall.

Within weeks, all five are fully converted.

He doesn’t stop there. Random wanderers show up because the landing page conversion rate is absurd. He closes them too.

Then comes the move that separates good founders from generational founders.

As soon as he has sixty enlightened disciples — sixty people who fully understand and can deliver the product — he sends them out. Sixty monks. Sixty different directions. His instructions:

“Go forth for the good of the many, for the happiness of the many, out of compassion for the world. Let not two of you go the same way.”

Read that again.

“Let not two of you go the same way.”

THIS SHIT IS THE FIRST FRANCHISE IN RECORDED HISTORY.

This is the most sophisticated go-to-market distribution strategy in the ancient world executed by a guy who sleeps on the ground.

He invented:

• Regional sales territories

• Commission-free field reps (the monks literally can’t accept money — this eliminates comp plan drama ENTIRELY)

• A franchise model where every rep delivers the exact same core product while leveraging agentic customization for the end user

• Infinite scalability because the “product” is a teaching that costs nothing to reproduce

McDonald’s wishes. Salesforce WISHES.

PHASE 4: M&A (MERGERS & AWAKENINGS)

With his initial growth engine humming, the Buddha does something that, in my professional opinion, is the coldest business move in any religious text.

He goes on an acquisition spree.

His first target: Uruvelā Kassapa, a fire-worship guru with huge followers. Kassapa is the market leader in his region. Big brand. Loyal customer base. Terrible product, but incredible distribution.

The Buddha shows up and says: “Let me stay with you for a bit.”

What follows is the most patient enterprise sales cycle ever documented. Over several weeks, the Buddha:

1. Performs minor miracles (product demos)

2. Debates philosophy with Kassapa (objection handling)

3. Just... vibes in a way that makes Kassapa’s product look increasingly silly (competitive displacement through sheer presence)

Eventually Kassapa has his “oh shit” moment. He realizes his fire worship is the Blockbuster to the Buddha’s Netflix. He converts. His entire organization converts with him.

The next morning, a thousand fire-worshippers dump their ceremonial merch into the river.

This is a hostile takeover executed with zero hostility. The target company’s employees voluntarily destroyed their own inventory because the acquiring company’s product was so obviously superior.

Then he does it AGAIN. He acquires Kassapa’s two brothers and THEIR followings.

Then he recruits Sariputta and Moggallana — two 10x monks who had been studying under a different guru. These guys become his Chief Operating Officer and his Chief Product Officer. Sariputta handles doctrine (Product). Moggallana handles organizational logistics (Ops).

Within months, the Buddha has:

• Absorbed three competing organizations

• Recruited elite executive talent from a fourth

• Eliminated multiple competitors without spending a single gold coin

His M&A strategy: make the product so good that competitors’ employees defect voluntarily.

Write that on a whiteboard. Tattoo it on your forearm. Whatever you need to do.

PHASE 5: ENTERPRISE SALES & THE INFLUENCER FLYWHEEL

The Buddha now pivots to what I can only describe as the most visionary influencer-affiliate-enterprise hybrid sales motion ever conceived.

Here’s what he figures out: every kingdom has a prince or princess who is bored out of their mind. Rich, educated, existentially unsatisfied. These are the LeBrons of dissatisfaction. They have massive followings. They have credibility. And they are absolutely desperate for something meaningful to do.

The Buddha’s pitch to royalty:

“You know that emptiness you feel despite having everything? That’s not a bug. That’s the fundamental nature of conditioned existence. Come hang out in the forest with us — it’s incredibly chill — and I’ll show you what’s on the other side.”

HE IS SELLING ENLIGHTENMENT AS A LIFESTYLE BRAND FOR DISILLUSIONED ELITES.

And it crushes.

Because every royal convert is a walking billboard. When Prince Whoever shaves his head and joins the Sangha, his entire court goes “holy shit, if HE thinks this is worth giving everything up for...” and the pipeline floods.

But here’s the 4D chess: the Buddha doesn’t actually care about the royals as an end market. He’s using top-of-funnel prestige to unlock the mass market.

Because for peasants — people trapped in the caste system, people told by Brahmin priests that their suffering is deserved — the Buddha’s message is revolutionary:

“Your birth doesn’t determine your worth. Anyone can be liberated.”

For royalty, the product is premium wellness. For peasants, the product is radical liberation from an oppressive social system.

SAME PRODUCT. TWO COMPLETELY DIFFERENT VALUE PROPOSITIONS. SEGMENTED BY BUYER PERSONA.

Somebody get this man a Hubspot sales plan. Actually don’t, he’d break it. The deal pipeline would crash the servers.

King Bimbisara donates a bamboo grove. King Pasenadi becomes a patron. The merchant Anathapindika — and this is where I need you to sit down — buys an entire park by covering the ground in gold coins as payment and donates it as the Buddha’s permanent headquarters.

Lets do some math here.

The Jetavana monastery grounds covered approximately 80 acres. Gold coins in 5th century BCE India... carry the one... adjust for purchasing power...

Conservatively $400 billion in 2026 USD.

That’s the Buddha’s SEED ROUND.

No cap table negotiation. No board seats. No liquidation preferences. A guy just showed up and said “your product changed my life, here’s four hundred billion dollars’ worth of gold, please keep going.”

The Buddha’s customer acquisition cost at this point is literally walking up to people and talking.

His LTV is infinite because the product is the cessation of all suffering across all future lifetimes.

THE LTV:CAC RATIO IS MATHEMATICALLY UNDEFINED BECAUSE YOU CANNOT DIVIDE INFINITY BY ZERO.

Every SaaS founder reading this just had a seizure. Good. You should.

PHASE 6: THE HUBERMAN PROTOCOL (OPERATIONAL EXCELLENCE)

Quick sidebar on the Buddha’s daily operating rhythm, because it needs to be documented.

3:00 AM — Wake up. On the ground. No alarm. No “just five more minutes.” The man opens his eyes and is immediately in peak performance mode. Andrew Huberman would study this man’s cortisol response if he could.

3:00-5:00 AM — Meditation and psychic survey of sentient beings who need help. He’s scanning the entire region with his mind to identify high-priority leads for the day. This is the most advanced lead scoring system ever built and it runs on pure consciousness.

5:00-6:00 AM — Walking meditation. The ancient equivalent of the 5am CEO jog except he’s not doing it for LinkedIn content.

6:00-11:00 AM — Alms round and teaching. He walks to the nearest village, and teaches whoever shows up. Cold outbound, warm inbound, it doesn’t matter — every interaction is a sales conversation.

11:00 AM-1:00 PM — Meal and rest. His only meal. One bowl. Whatever’s in it. He’s eating one meal a day, no snacking, no “quick protein shake”. This man is running a multinational spiritual organization on fewer calories than your morning Starbucks order.

1:00-5:00 PM — Executive level coaching with head monks, meeting with donors, resolving organizational issues. Office hours. Except his office is under a tree and the issues are things like “I achieved the third jhana but can’t stabilize the fourth” which is the 500 BC equivalent of “my Salesforce automations keep breaking.”

5:00-7:00 PM — Public discourse. The EVENING KEYNOTE. Every single night. This is his content engine. He’s producing a full-length dharma talk DAILY for forty-five years. That is 16,425 consecutive nights of content. Joe Rogan has 2,200 episodes over 15 years. The Buddha did 16,000+ over 45. And he didn’t have a studio, a producer, or Jamie pulling anything up.

7:00 PM-10:00 PM — More meetings and administrative work.

10:00 PM-3:00 AM — Sleep. Five hours MAX. On the ground. In a forest.

He maintained this schedule for forty-five years.

He never took a vacation after that initial seven-day sabbatical post-enlightenment.

He walked an estimated tens of thousands of miles during his teaching career. Barefoot. In monsoon seasons. Through territory with bandits and wild animals.

This man’s Whoop data would make David Goggins cry.

PHASE 7: CRISIS MANAGEMENT (THE DEVADATTA INCIDENT)

Now. At the absolute peak of the Buddha’s market dominance, he faces his first — and only — serious threat — Devadatta.

Devadatta is the Buddha’s cousin. He’s talented, ambitious, and deeply, pathologically jealous.

He is the Judas, the Brutus, the guy in your org who smiles in all-hands but is actively DMing your top performers trying to poach them.

Devadatta’s attack plan:

1. Political alliance — He cozies up to Prince Ajatasattu (who has his own daddy issues and recently KILLED HIS OWN FATHER to take the throne). Devadatta basically gets an angel investor with a body count.

2. Product fork — He proposes “five stricter rules” for the monks, trying to make the Buddha look soft. The Buddha sees through this instantly. He knows Devadatta doesn’t actually want stricter rules — he wants the BRAND.

3. Literal assassination attempts:

   • Sends hired killers → they convert on sight. THE ASSASSIN BECAME A CUSTOMER. The Buddha’s close rate is so high that people sent to murder him end up subscribing.

   • Rolls a boulder down a hill at him → it splits in two and misses.

   • Releases a drunk elephant at him → the Buddha calms it with his energy and it kneels before him. He turned a competitive attack into a PR moment.

Devadatta does manage to temporarily poach about 500 monks. FIVE HUNDRED. That’s a decent chunk of the org.

The Buddha’s response?

He sends Sariputta and Moggallana — his two best closers — to the breakaway group.

Not to fight. Not to argue. Just to teach the other monks to sell.

The monks come back within days.

DEVADATTA COULDN’T RETAIN HIS OWN POACHED CUSTOMERS FOR A SINGLE SPRINT CYCLE.

The Buddha’s post-crisis all-hands email, paraphrased: “Oh, they’re back? Cool.”

The man doesn’t even acknowledge the coup. He doesn’t write a company blog post about it. He doesn’t do a PR crisis response.

He just keeps selling and shipping.

This is what happens when your product is so good that your competitors can’t retain defectors even when they acquire them for free.

PHASE 8: PLATFORM PLAY & MARKET EXPANSION

By this point the Buddha is operating what can only be described as a platform business.

The core product (the Dharma) is open-source and infinitely forkable. Anyone can teach it. Anyone can practice it. There are no patents, no IP restrictions, no licensing fees.

His presence, his reputation, his teaching methodology, his organizational structure (the Sangha) — these create a network effect that no individual teacher can replicate.

He builds features for every market segment:

• For monks: The Vinaya — a comprehensive operating manual with 227 rules covering everything from how to fold your robe to how to handle money (you don’t). This is the most detailed employee handbook in ancient history.

• For laypeople: The Five Precepts — a lightweight ethical framework that’s basically a free tier. Don’t kill, don’t steal, don’t lie, don’t drink, don’t cheat. Easy to understand, hard to master, and it keeps users engaged with the broader ecosystem.

• For philosophers: The Abhidhamma — deep analytical psychology and metaphysics for power users who want to understand the entire technical stack.

• For women: He eventually opens the Sangha to female monastics (the Bhikkhuni order), over significant internal objection. He expanded his TAM by approximately 100% with a single policy change.

The platform grows to tens of thousands of monks and an uncountable number of lay followers across multiple kingdoms.

And the whole time — the WHOLE TIME — he’s still doing outbound. PERSONALLY.

He’s still walking from village to village. Still giving personal demos. The CEO of the biggest organization in the ancient world is still making cold calls.

This is the thing that separates the Buddha from every other leader in history.

He never stops selling.

He never promotes himself to “Visionary” or “Chair of the Board” and stops doing the work. He never hires a VP of Sales and stops talking to customers.

HE is selling, from Day 1 until the day he dies. Literally.

PHASE 9: THE EXIT (OR: THE FOUNDER’S LAST SALES CALL)

The Buddha is 80 years old. His body is falling apart. He’s been walking barefoot across India for forty-five years on one meal a day and five hours of sleep.

He knows he’s dying. He’s known for months.

Does he retire? Does he go to his equivalent of a beach in Malibu? Does he write a memoir?

NO. He is the Buddha, so he goes on one more sales trip.

He walks from town to town, teaching as he goes. He’s giving full dharma talks while barely able to stand. His back hurts. His stomach is bad. He tells Ananda, his closest attendant, “my body is like an old cart held together with straps.”

At a village called Pava, he stops for a sales dinner at the home of a customer named Cunda.

Cunda serves him a dish that makes him violently ill. Food poisoning. In his 80s. On the road.

But before the meal, the Buddha pulls his monks aside and says:

“Cunda’s meal will be my last. Don’t blame him. This is just how it goes.”

He called the shot. He knew the food would kill him, ate it anyway because you don’t refuse a customer’s hospitality.

He stumbles to a grove of sal trees between two towns. He lies down on his right side. Monks are gathering, crying, freaking out.

His disciples ask: “What do we do without you?”

His response — and these are his actual, historical, extremely well-documented last words:

“All conditioned things are impermanent. Work out your salvation with diligence.”

Let me translate this for you guys:

“I’m not going to be here to close deals for you anymore. The product works. You’ve seen it work. You know the playbook. Now go sell.”

He dies. On the road. Mid-sales-trip.

THE LIFETIME METRICS

Let’s close with the numbers, because numbers don’t lie:

Career Duration: 45 years of active selling

Customer Acquisition Cost: $0. Walking and talking. Zero capital expenditure.

Lifetime Value per Customer: Infinite (product eliminates suffering across all future lifetimes)

LTV:CAC Ratio: ∞:0 (mathematically undefined; destroys every SaaS benchmark ever published)

Churn Rate: Near zero. Even Devadatta’s poached customers came back within days.

Total Capital Raised: conservatively north of $1 trillion in 2026 USD.

Financing Structure: Zero equity dilution. Zero board seats. Zero liquidation preferences.

Product Lifespan: 2,500+ years and counting. Still in market. Still growing. Still zero marginal cost of distribution.

Competitors Eliminated: Every fire-worshipping cult, ascetic sect, and Brahminical school in the Gangetic plain. Most absorbed voluntarily.

Exit Strategy: Death on the road at 80, product sells itself so well there’s no succession CEO needed.

Take that last point in: The most successful salesman in history built something specifically designed to not need him, then died on the road proving he meant it.

His product has 500 million active users today.

He never wrote a NYT best seller. He never did a podcast. He never posted “Grateful 🙏” on LinkedIn. He never rang a bell at the NASDAQ.

He just kept walking, kept talking, and kept closing.

Work out your salvation with diligence.

Now go hit your fucking quota.

You feel like you have to make people care about your thing, and it’s uncomfortable, so you apologize. I’ve done this, you’ve done this.

When you think your job is to make people care, you become a Care Salesman.

It’s not just the mewling apology in your email though. It’s your presentation that opens with a dozen justifications, it’s asking for a meeting and ending with “no worries if not”, it’s the idea you never went after because people “didn’t get it”.

It’s the million ways you subtly telegraph to other people: I don’t believe I’m worth your investment

You Don’t Beg to Deliver Good News

Last week I coached a founder through pitching a difficult exit to his investors. He was visibly nervous.

Midway through delivering the prepared script, he kept randomly spinning off onto tangential apologetic explanations. Why the market wasn’t a good fit, why expansion was more complicated than he thought, why their seven pivots didn’t pan out.

Every time, I cut him off. “You’re getting nerd-sniped into apologizing.” There’s nothing to apologize for. We tried. It didn’t work. We have a good deal on the table. That’s the whole message.

He didn’t need to beg for the right to deliver the good news. He needed to believe he was delivering good news in the first place.

If you don’t buy it, why should I?

The Care Salesman has outsourced the verdict on their own value to someone else. The fear you feel at shooting your shot is a symptom of an unresolved internal question, not a communication style problem.

That question is: do you really believe what you’re bringing is worth someone’s attention?

If not, the substance of your pitch is the least of your problems. The words still matter, but the right words won’t save you if you don’t believe what you’re saying.

People feel it when you need the deal more than they need your thing.

If you’re running a hot funding round, the conversation isn’t telling investors why they should give you a shot, it’s asking them what unique value they bring to the partnership.

If you’re selling something people actually want, the question isn’t why they should buy. It’s whether you have room for them.

You are an emissary sent to deliver the good news unto the breathlessly waiting masses.

So act like it. Shift your posture. Lean back.

Confidence is Considerate

The irony is that leaning back is the more considerate move. Here’s my thing. Here’s why it might matter to you. Do you want it? I’m fine either way.

Your job isn’t to make people care. Your job is to make your thing great, and help the right people understand it.

Get out of the persuasion business. Deliver the good news instead.

Along the way, my dear friends have given me lots of gracious, loving feedback.

These are not edits, they are direct quotes from transcripts of recordings of feedback sessions from these “friends”.

I think it’s useful to share them for other people who might be interested in how to become a better writer.

To be clear - inkhaven participants and staff are extremely supportive and kind. My friends less so.

—

1

X: “Do you want the cunty version or the nice version?”

Me: “You can be Direct.”

X: “If you weren’t literally sitting next to me right now, I would absolutely not be reading this.”

Me: “Because it has too many words?”

X: “Because it’s bad.”

2

X: “I literally don’t know how you manage to write about such fascinating topics in a way that makes them seem so boring.”

3

X: “This draft is 50% closer, but it still feels like I’m reading a linkedin post about what you learned about b2b sales.”

4

X: “This writing feels kind… not castrated… but like, pedantic?”

5

X: “It’s like you’re writing for the bully at school who’s going to make fun of you and tell you ‘that’s lame’”

6

X: “It’s like you put a condom on yourself, when you should be just freely spaffing about.”

X2: “yeah that’s a good way to put it”

Me: “.......”

7

X: “I mean it’s clear that you’ve put a thousand hours into getting good at writing linkedin posts.”

8

X: “Clearly either the writer of this piece is an idiot, or they think I’m an idiot”

9

X: “The way it’s written is so plain that any attempt at curiosity just slides off of it when attempting to grasp it.”

10

X: “that was the most interesting thing you’ve said about this topic today”

Me: “Thank you this is helpful.”

Me: “Also I hate this”

11

X: “You’re kind of distilling a multicolored experience into a lukewarm grey”

12

X: “Just keep one sentence for every 10 you have now”

13

X: “This reads like it’s been through five levels of sloppification.”

14

X: “So you invented a way to take drugs before you were old enough to get drugs? That’s already more interesting than anything you’ve made me read today.”

15

[After X suggests something]

Me: “I literally said that in the last draft you read”

X: “Well for some reason I didn’t read it.”

16

X: “It’s sort of like if someone was feeding me the feel good version of the question so I can pretend to answer it instead of an actual question.”

17

X: “It’s like I want to be teleported into cloud atlas, you know, but then instead you’re there beside me explaining it to me.”

18

X: “But I think you’re really close, it’s not that bad actually.”

19

X: “You should just write a piece about the feedback you’ve gotten.”

Me: “That’s actually a great idea.”

Doing a boring budget with your partner, starting a business, convincing an ally to join your righteous cause all involve many negotiations.

Some negotiations, though, are high-stakes.

The advice you read in a best-seller or see on shark tank might lead you to think that negotiation is a cartoonish game of chicken where everyone makes demands at each other until someone blinks.

I spent about ten years working with founders, executives, and investors on business exits and fundraises. I’ve also been in my own high-stakes negotiations, with my own money and feelings on the line. I now advise executives on negotiation and sales as a part of my work.

I’ve seen people at every level fundamentally misunderstand what negotiation is, and how to play to win.

This is the first piece in a series on uncommon negotiation advice. It’s advice I wish I’d been given sooner. This piece covers how you can avoid the most common mistake that can cause you to lose before you even start a negotiation.

The mistake is simple: having polluted intentions

Intentions are stronger than goals

Most people who lose negotiations don’t lose at the table.

They lose weeks or months earlier, in the private story they’ve constructed about what they want and why. By the time they sit down, they’re running on a set of motivations they haven’t honestly examined.

The most common negotiation advice you will read is “figure out what you want”, and this is good advice I’ll cover later in the series.

But before you do that, you should get very clear about your intent. Your intent is upstream of your specific goals. Your goal might be “get as much money as possible” but your intent might be “win against these assholes”.

Without dedicated investigation you may not know your own intent. Your true intentions may be petty, vindictive, self-protective or just counterproductive.

Intentions quietly shape your decisions.

In a high stakes negotiation, if you don’t align and realign your intent with your goals, they will very likely conflict with each other in ways that hurt your position.

Navigating Polluted Intentions

A friend of mine went through a long protracted negotiation with a former employer.

She’d spent 20 years serving a family-owned business faithfully. She was unceremoniously fired when the failson took over. So she sued for wrongful firing. She had lots of receipts.

But along the way, as the settlement offers got higher and higher, she kept saying no. The whole way, her lawyer was beside her whispering big numbers in her ear.

When I talked to her though, it became very clear: she wanted to hurt them. She was on a quest for vengeance, not just money.

This is an example of polluted intentions: aims that are real but actively damage your position if you let them run the show.

The problem is that this desire is exactly opposite to the strategic goal. There was a real chance she’d lose if the case went to court. There’s a real chance she’d have to pay the other side’s legal fees. She also needed the money, and going to court pushed out the resolution by years. Letting the case go to court was a strategic blunder.

In a high stakes negotiation, your most emotionally compelling options are often your most expensive ones.

When I help friends or clients in high-stakes negotiations now, I see this constantly. It’s a loaded foot-gun sitting under their pillow while they sleep.

Polluted intentions make you vulnerable to bad advice and cracking under pressure.

They also cloud your decision making with unrealistic expectations. To win a high-stakes negotiation, you will have to make concessions. If you accidently make your win-condition “get what I deserve” or “inflict as much pain as possible” - you’re cutting off your own nose to spite your face.

So the first step to a successful negotiation is to identify your REAL intentions, including the dark ones hiding in the corner you’d rather not say out loud.

By the way, the court session got scheduled for 2028.

Internal Chess Game

You must be willing to make sacrifices to your self-perception to win.

You will want to be validated. You will want to take credit you can’t take. You will want to say true things you can’t say. You will want to tell a story that feels good. You will want to be honest with people who will use your honesty against you. You will want to hurt someone who hurt you.

In order to achieve your goals, you will have to set all that down repeatedly. Feeling good is not the goal. Indulging yourself is costly.

This isn’t about adopting a machiavellian world-view, or contorting into permanent self-denial.

Winning requires being clear-eyed enough to know which of your wants and desires are driving you and which are traps.

It also requires treating your intuitive sense of right-and-wrong with more skepticism than is comfortable, over and over again until you get the best outcome your situation affords.