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“If I could choose one gift for my leprosy patients it would be the gift of pain.”

Paul Brand

For days my HeadsUp landing page was broken.

An AI agent broke it and the board I read each day kept counting visitors while each one landed on the broken page.

Developers keep their code on GitLab. In 2017 one of its engineers meant to wipe a spare copy of the database and typed the command on the live one.

About 300 GB was gone.

The team turned to its five backup systems.

None of them worked.

The daily backup crashed each time it ran and sent a warning email. A mail server rejected every one.

The best copy left was a snapshot an engineer made by hand hours earlier.

GitLab lost about 5,000 projects.

GitLab’s backups warned the team each day. None of the warnings reached a person.

If something broke in your business today, which metric would tell you?

Warnings are one kind of signal. A body also has a signal that pulls it toward what it needs.

In the 1990s, Richard Palmiter’s lab at the University of Washington bred mice that couldn’t make dopamine.

Dopamine drives an animal toward a reward.

At first the mice looked healthy. After about 10 days they slowed down and stopped eating.

Food sat in reach. They could still find it and swallow it.

Within weeks, without help, they starved.

A shot of a drug called L-DOPA gave them enough dopamine for about 10 hours. In those hours they ate.

Their bodies needed food the whole time. Without dopamine, nothing told them it was worth eating.

If nobody reads the metric that shows what’s working in your business, you can miss it too.

Frank Meeks watched what people ate. He owned dozens of Domino’s stores around Washington, DC.

In 1983, late-night orders from the Pentagon jumped. Soon after, the US invaded Grenada.

Meeks took it for a coincidence.

In 1989 the orders jumped again before the US invaded Panama.

On August 1, 1990, he said, the CIA ordered a record 21 pizzas in one night.

The next day Iraq invaded Kuwait.

People order dinner when they work late. They work late when something big is coming.

Meeks had no view inside the Pentagon.

His order count told him something was happening there.

A body runs on signals too. Pain warns it. Hunger and pleasure pull it toward what it needs.

Your metrics are your business’s nervous system.

GitLab’s warnings never reached a person, so nobody knew the backups failed. The mice lost the signal that says eat and starved beside their food. Meeks read his orders and knew something big was coming.

🩺

What metric could you check daily to stay on top of your business?

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“Too much safety seems to yield only danger in the long run.”

Aldo Leopold

For years I believed that the bigger my habits were, the bigger my anti-habits needed to be.

A habit is something I choose to do. An anti-habit is something I choose to avoid. One of my anti-habits was eating only inside a 6-hour window. Another was finishing work by 4pm.

Eating only in that 6-hour window, it felt like my brain started to conserve energy. The quality of my thinking dropped.

The fast was costing me the quality of thought my goals needed.

The 4pm finish worked until my ambitions grew. On the days I wanted to push harder, the work had to stop anyway.

The bigger my goals got, the tighter the rule squeezed my days.

For about a century, the US put out each fire it could reach in Yellowstone.

Small fires used to clear away dead wood and brush. Without them, the dead wood stayed on the forest floor and piled up year after year.

In the dry summer of 1988, fires reached all that fuel and burned about a third of the park.

The rule meant to protect the forest built the fuel that burned it.

Marc Randolph kept a narrower rule. Each Tuesday at 5pm, he left work to spend the evening with his wife.

He kept his Tuesday nights for more than 30 years, through the founding of Netflix. He tells the story in his book That Will Never Work.

His rule was small enough to survive building Netflix.

Each anti-habit guards a goal. Push one far enough and it starts working against that goal.

🔥

What rule could you loosen so it stops blocking your goal?

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“Use poison to fight poison.”

Chinese idiom

I asked how noise canceling headphones work and the answer sent me looking through wildfires, bank runs and computer worms.

Tiny microphones on the headphones pick up the noise around you, like a plane engine. A small computer inside flips that sound wave upside down and plays it through the speakers.

Where the engine pushes the air up, the flipped wave pulls it down by the same amount. The 2 waves cancel out and the engine goes quiet.

That made me wonder where else something gets inverted to cancel something out.

In 1949 Wag Dodge led a crew of firefighters who parachuted into Mann Gulch in Montana. A wildfire raced up the slope at them.

Dodge lit a fire in front of himself and lay down in the burned ground. Since his fire burned the fuel first, the wildfire passed over him. He pressed his face to the dirt to breathe the air near the ground.

He lived.

If a wildfire came at you, you’d likely run.

His crew ran and wouldn’t follow him in. 13 men died. Norman Maclean wrote Young Men and Fire about them.

Dodge fought a fire with a fire. In Uzbekistan, Soviet engineers fought one with a bomb.

A gas well there caught fire in 1963 and burned for nearly 3 years.

Gas kept pushing up out of the ground. The engineers set off a nuclear bomb underground beside the well and the blast pushed the rock in on it. The flame went out in about 23 seconds.

That fire ran on gas. The panic of 1825 ran on fear.

People rushed to pull their money out of British banks.

If you ran a bank that week, you’d want to hold on to each pound you had. The Bank lent instead. A director named Jeremiah Harman later testified that it lent “by every possible means.”

One account says the Bank found a box of about 600,000 old one-pound banknotes and put those into circulation.

The panic faded once people believed they could get their money.

The Bank stopped a run on its money by handing out more money. In 2003 someone tried the same move with a computer worm.

A worm called Blaster was spreading across Windows computers. If your PC caught it, Windows might shut down and restart on its own.

Then someone released a second worm, Welchia, to fight it.

Welchia spread from machine to machine, removed Blaster and installed Microsoft’s patch.

Nobody ever claimed it. Hidden in its code was a note from its writer about loving their wife and baby, plus a promise that the worm would remove itself in 2004. It reads like the work of a vigilante trying to rid computers of Blaster.

A sound wave against a sound wave. A fire against a fire. Money against a run on money. A worm against a worm.

The fix for a problem can be the same thing pointed the other way.

🎧

What problem in your work could you cancel by inverting it?

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“Do one thing every day that scares you.”

Mary Schmich

I know that each time I go running I’ll get a little fitter and a little calmer.

That’s what a farming habit does: you repeat the same action for a return you can count on.

Deep work is my hunting habit. Each morning I give 2.5 hours to whatever matters most that day.

The hours stay fixed. What fills them changes.

Jesse Livermore focused on hunting. He made his living betting on where stock prices would go.

Edwin Lefèvre tells the story of his early years in Reminiscences of a Stock Operator.

When the stock market crashed in 1929, Livermore bet on the fall and made about $100 million.

A few years later he filed for bankruptcy. On Thanksgiving in 1940 he died by suicide in a Manhattan hotel. He left his wife a note that said he was tired of fighting.

Stu Ungar played poker for a living. He won the main event at the World Series of Poker 3 times.

Nolan Dalla and Peter Alson tell his story in One of a Kind.

Over his career he won an estimated $30 million.

He died in a cheap Las Vegas motel room with $800 in his pocket.

Hunting can make you rich and leave you broke a few years later.

Carl Fisher chased one big project after another. He paved a racetrack in Indianapolis with brick and pumped sand out of Biscayne Bay to build Miami Beach.

By the mid-1920s he was worth an estimated $50 million. Then he borrowed against Miami Beach to build a summer resort at Montauk.

It opened just in time for the 1929 crash.

A few years later Fisher was broke, drawing a salary from his old partners to promote the city he built. Mark Foster tells the story in Castles in the Sand.

When your week holds only hunting, a bad stretch can take everything.

Ronald Wayne chose farming over hunting. He worked as a draftsman at Atari.

When Steve Jobs and Steve Wozniak started Apple in 1976, Wayne typed up the agreement himself. It gave him 10% of the company.

Since a partner could be on the hook for the company’s debts, Wayne wanted his savings out of reach.

Days later he took his name off the agreement and stayed at Atari.

He tells the story in Adventures of an Apple Founder. His 10% of Apple went for $800.

You can keep your savings safe and still trade away the upside.

Kenny Chow drove a yellow cab in New York for years. He borrowed about $700,000 to buy a taxi medallion.

Then Uber and Lyft filled the streets with cars.

By the spring of 2018 a medallion sold for about $200,000. That May his body was found in the East River.

Chow kept showing up for each shift. Uber and Lyft still cut his medallion’s value by more than two-thirds.

Alvah Roebuck repaired watches for a living. He went into business with Richard Sears.

The catalog company carried both their names.

Since Sears kept taking big risks with the company’s money, Roebuck asked to be bought out.

He sold his share for about $20,000 and stayed on to run the watch and jewelry department.

By 1916 Sears was the largest retailer in the country.

Roebuck lost much of his money in the 1929 crash. At about 70 he went back to work for Sears as a spokesman, touring stores that still carried his name. Boris Emmet and John Jeuck tell the company’s early years in Catalogues and Counters.

When your week holds only farming, you can miss the upside and still lose what you saved.

Andre Geim farmed and hunted. He spent his weeks on his main physics research and gave Friday nights to experiments that might lead nowhere.

One Friday he poured water into a powerful lab magnet and watched the water float in the air.

Friday nights cost Geim one evening a week.

Most weeks they paid nothing.

Over about 15 years most of those Friday experiments failed. One used Scotch tape to peel graphite into sheets one atom thick.

It won Geim and Konstantin Novoselov a Nobel Prize. He tells the story in his Nobel lecture, Random Walk to Graphene.

Steve Wozniak designed calculators at Hewlett-Packard.

Outside work he built a computer to show off at a hobby club in Palo Alto.

He offered the computer to HP 5 times.

HP turned it down each time, so he kept his job and started Apple with Steve Jobs.

Wozniak left HP once an investor put money into Apple. Wayne sold his share that same year. Wozniak kept his.

He tells the story in iWoz.

Your day job can pay for the hunt.

Sara Blakely sold fax machines door to door. Most doors closed in her face.

She kept the job and put $5,000 of savings into a pair of pantyhose with the feet cut off.

In Dallas she got a meeting with a Neiman Marcus buyer, changed into her prototype in the restroom and walked out with an order.

She quit selling fax machines after Oprah named Spanx one of her favorite things.

In 2012 Forbes named her the youngest self-made female billionaire.

Hunting alone brings booms and busts. Farming alone works until something outside your control hits.

Farm to stay steady. Set aside time each week to hunt.

🏹

How could you free one hour each week for new opportunities?

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“Customers first, employees second, shareholders third.”

Jack Ma

I’ve spent 6 years studying businesses for Trends.vc.

Lately a new kind of customer shows up in the companies I study: the AI agent.

I grade business models by who pays, from a C for consumers to a B for businesses and an A for agents.

Businesses beat consumers on four counts:

• More urgency
• Higher prices
• Bigger budgets
• Fewer cancellations

Paul English co-founded the travel site Kayak. Then he launched a vacation-planning app called Lola. Within its first year his team found 80% of its users were traveling for work.

Business travelers stuck with Lola, so English rebuilt it as a corporate travel tool.

Nick Gray started Museum Hack by giving offbeat museum tours to his friends for free. Then he added weekday team-building tours for companies. They became one of the company’s most successful lines.

The company grew to $2.8M a year and Gray sold it in 2019.

Benjamin Houy grew a French-learning app to $10K a month. Growth stalled after most of his audience bought it.

He felt consumers paid little and canceled fast, so he left the app to build a tool businesses use to track how AI chatbots mention them.

If you sell to consumers today, a business version of the same product can move you up a grade.

Since an agent works in the background, selling to agents beats selling to businesses. Agents search the web and build apps while the people who set them up sleep.

The research firm IDC expects companies to go from about 29 million AI agents in 2025 to over 2 billion by 2030. That’s about 1.2 million new agents a day, more than 3 times the number of babies born each day.

If you sell to agents, your pool of possible customers grows by about a million a day.

Nikita Shamgunov runs a database company called Neon. The coding site Replit plugged Neon in and created about 10 databases a day.

Then Replit launched an AI agent that builds apps for people.

Neon created 13,000 databases in one day. Most of them went to people who never heard of Neon.

Ivan Burazin sold coding setups to engineers at big companies and made a few hundred thousand dollars a year.

In 2025 he rebuilt his company Daytona for AI agents and started over at zero.

Daytona reached a pace of $1M a year in under 50 days. Most customers sign up on their own.

Daytona has grown about 51% a month since then.

Will Bryk built a search engine for machines called Exa. It charges for each search, so it earns more each time an agent runs one. In about 3 years Exa grew to $100M a year.

A typical business software company takes about 9 years to get there.

Investors call it net negative churn when customers who stay spend enough extra to outweigh the money lost to the ones who leave. Since an agent pays more the more it works, charging by use makes net negative churn possible.

If your customer’s agent does twice the work next month, you get paid twice as much without selling anything.

Guillermo Rauch runs a website hosting company called Vercel. Researchers asked the coding agent Claude Code to put a JavaScript app online. It picked Vercel each time.

Coding agents went from under 3% of Vercel’s new business at the start of 2026 to about half by October.

Zeno Rocha built an email service for developers called Resend. In the same tests Claude Code picked Resend about 9 times as often as the older market leader SendGrid.

An agent tends to pick the same tool each time, so the top pick for a job gets most of its customers.

At the search tool company Ahrefs, AI models sent 0.5% of visitors and 12.1% of signups.

Agents are a new kind of customer. They multiply by the million each day, work while their owners sleep and pay for each job they run.

🤖

What could an agent buy from you?

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“A single bracelet does not jingle.”

Congolese proverb

Each day I sit for insight meditation.

I’ve done it for over 15 years.

About a year ago, I started morning pages as well. Writing whatever is in my head the moment I wake.

When I write the pages first, my meditation goes much deeper.

Without morning pages, I spend the first 30 minutes of each session on what I could have written down in five minutes.

Other habits combine the same way.

For the comedian George Carlin, it was notes and files.

He wrote ideas on little memo pads, mostly while watching TV.

When no pad was near, he spoke into a digital recorder.

At 18, a radio boss told him to write down each idea, even the ones he couldn’t use yet. “A good idea is of no use to you unless you can find it.”

So Carlin filed each note in folders within folders. One subject was “The Way We Talk.”

Each time he reread a note to file it, it stuck better.

“The path gets a little richer and deeper,” he said.

When he sat down to write an act, he wrote from the files.

The files let him find each note the day he needed it.

He made 14 HBO specials.

For the saxophonist Sonny Rollins, it was yoga and improvising.

He studied yoga in India.

In 2014 an NPR host asked what it brought to his playing. “It’s the concentration level,” he said.

When he improvised, he tried to reach his subconscious. “You can’t think and play at the same time. Believe me, I’ve tried it.”

He said the contemplative forms of yoga aim for that same state. “When you’re into yoga and when you’re into improvisation, you want to reach that level.”

So the yoga trained the concentration his playing needed.

Aidan Levy tells his story in Saxophone Colossus.

For the surgeon James “Butch” Rosser, it was a video game and surgery.

In 2005 he kept an Xbox, PlayStation 2 and a GameCube a few strides from his operating room.

He did keyhole surgery, where the surgeon works through small cuts with a camera and long tools.

Before an operation he warmed up on a game called Super Monkey Ball.

His study tested the warm-up on other surgeons. Those who played right before a keyhole drill made fewer errors and finished it about 11 seconds faster than those who didn’t.

A game made the surgeons faster and more accurate on the drill.

Economists call this complementarity. The value of one thing rises with what you pair it with.

Two good habits can pay more together than one great habit alone.

🧩

How could two of your habits feed each other?

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“Thinking in bets starts with recognizing that there are exactly two things that determine how our lives turn out: the quality of our decisions and luck.”

Annie Duke

Each day I do a few things that scare me.

Like a sales ask, a hard conversation I’ve been avoiding or a run longer than I’ve tried before.

Before I start one of these courage challenges, I give it a score out of 100 for how hard I expect it to be.

A hundred is the hardest thing I can picture doing.

To pick the number, I have to play the challenge through in my head.

• Where I’ll be
• What I’ll do first
• Where it could go wrong

Amazon has a rule for new products.

Before a team builds anything, it writes the press release.

The press release announces the finished product to customers. Below it, the team answers the questions those customers would ask.

When Amazon started on the Kindle, the team had to picture a reader buying one. That reader wanted to download a book from anywhere and pay only for the book.

Colin Bryar and Bill Carr tell the story in Working Backwards.

Writing the press release raised a question: who pays for the wireless connection?

The team had to answer it before anyone built a device.

Annie Duke played poker for a living for nearly 20 years.

In Thinking in Bets she writes about a question poker players ask when you sound sure of something: Wanna bet?

Now being wrong would cost you money. To decide whether to take the bet, you have to run through how you could be wrong.

Often you get less sure before anyone puts money down.

Putting money on the claim makes you think it through.

Ray Dalio founded the investment firm Bridgewater and made his money trading markets.

In 1982 he told Congress a depression was coming. He was wrong. The market started a long climb instead.

He went broke.

He let his employees go and borrowed $4,000 from his dad to pay his bills.

After that he wrote down his reasons before each trade. When one closed, he could check what he wrote against what happened.

He tells the story in Principles.

Over the years those notes became the rules Bridgewater uses to trade.

Writing the reason made him think before he bought. The pile of notes showed him where his thinking went wrong.

You can do small things that force you to think better before you act.

🧠

What small act could raise the quality of your decisions?

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“Your taste is why your work disappoints you.”

Ira Glass

I’ve written a daily essay for almost 300 days.

Most days what I publish falls short of what I imagined.

Ira Glass hosts This American Life. As a college kid he walked into NPR’s Washington office and offered to work the summer for free. He cut tape, wrote newscasts and filled in wherever they needed him.

By his account he couldn’t write and structure a story well until he was almost 30. Years later he described that stretch in an interview about storytelling:

“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take a while. It’s normal to take a while. You’ve just gotta fight your way through.”

The gap between my taste and my output closed in nine posts so far.

How-I Beats How-To packs a big idea into a short, high-signal post. When knowing how to do something turns into a commodity, the story of how you did it becomes valuable.

Compound Lifts is where everything in my life started to become material for essays, even a 5K I walked on a treadmill during my mastermind calls.

How to Get Lucky in Life looks back on an important stretch of my life through my experiments habit and the rooms it led me to.

Do Less, Get More: The F1 Math was published as I was still trying to understand the power of removal. Each time I explain this essay to someone, my appreciation of the piece deepens.

We Are All Investors was one of my first tries at showing that we invest more important resources than money.

Consistent But No Progress? It’s the Hurdle Rate speaks to how you can be consistent and still fall behind. The idea of hurdle rates is underappreciated. This was an early attempt at getting the concept of minimum effective doses across to people.

Why Mormons Get Rich and Adventists Live to 100 was a great title and I was surprised to see that readers shared my esoteric interest in religious habits.

Habit Banking: What You Can Bank and What You Can’t was the first time I shared how I picture habits as reserves that you can build ahead of time. This became the basis for the habit app I built and use each day.

The Math of Inevitable Success passed on another internal model about how persistence combined with avoiding ruin makes success a question of when. Not if.

Out of almost 300 essays, nine have matched my taste.

More often than not, I miss.

Volume is how you close the gap between your work and your taste.

📚

What commitment could you keep until your work matches your taste?

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“Follow effective action with quiet reflection. From the quiet reflection will come even more effective action.”

Peter Drucker

I look back on a year of my life in about an hour.

Each night I write in a pocket journal what went well, what I could have improved and what surprised me.

On Sundays, I build a weekly review from the daily reviews. The wins that mattered most and the improvements that still matter carry into it.

Each month I build a monthly review from the weeks. Then I build a quarterly review from the months and a yearly review from the quarters.

The Boston surgeon Ernest Codman kept a written record of how each of his surgeries turned out.

For each patient he wrote down what was wrong, what he did and how it went. A year later he checked on the patient and added how they were doing.

Reading those records back, he found 123 mistakes and traced each one to its cause.

Some came from a gap in his skill. Others came from a bad call during surgery, poor equipment or a wrong diagnosis.

In 1916 he published all 123.

Other surgeons shunned him for it. His idea that hospitals should track their results grew into the Joint Commission. That group still inspects American hospitals.

William Mallon tells the story in Ernest Amory Codman: The End Result of a Life in Medicine.

Harvard researchers tested end-of-day writing at a call center in India. New hires there spent weeks in training before they took their first calls.

One group spent the last 15 minutes of each day writing about what they learned. Another group kept working. On the final test, the writers scored 23% higher.

🪞

What question could you answer each night before bed?

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“Sticks in a bundle are unbreakable.”

Kenyan proverb

One of my favorite chess openings hides a bishop behind a knight.

When the knight jumps, the bishop fires across the open lane, so one move makes two threats. In the Arabian mate, a rook and a knight trap a king in the corner. In Alekhine’s Gun, two rooks and a queen line up in one column to hit the same square.

Habits, money and teams have powerful combinations too.

Habits

The coffee nap

In 1997, the sleep researchers Louise Reyner and Jim Horne put sleepy drivers in a car simulator for a two-hour afternoon drive.

Before the drive, each one got a placebo, caffeine or caffeine followed by a nap of under 15 minutes.

Since caffeine takes a while to kick in, the nap fits inside the wait. You doze off and wake as the caffeine lands.

Compared with the placebo, caffeine alone cut driving incidents by about two-thirds. Caffeine with the nap cut them by 91%.

Temptation bundling

The Wharton professor Katy Milkman recruited students and staff at a university gym who wanted to work out more.

Some of them got gripping audiobooks they could only listen to at the gym. To hear the next chapter, they had to show up.

In the first weeks, that group went to the gym 51% more often than the group with no audiobooks.

The story they wanted to finish dragged them to the workout they kept putting off.

Money

The barbell

Investors call one money setup the barbell. Put most of your money somewhere safe and a small slice into bets that could go to zero or multiply.

The safe pile alone barely grows. The wild slice alone can wipe you out.

Together you survive a crash and catch the upside.

Costco

Costco caps its markup at about 14% on brand-name goods. At that margin, the shelves earn a small share of the profit.

Most of the profit comes from the membership card. Shoppers pay a yearly fee to get in the door.

Nearly 90% of them renew.

The low prices sell the membership. The membership pays for the low prices.

Teams

Stockton and Malone

John Stockton and Karl Malone played 18 seasons together for the Utah Jazz.

Their favorite play took two players.

Malone set a screen on Stockton’s defender. If the defense stayed with Stockton, Malone rolled to the basket for the pass. If they chased Malone, Stockton had the shot.

Players call it the pick-and-roll.

Guard one and you leave the other open.

Stockton retired with the most assists in NBA history. Malone retired second only to Kareem Abdul-Jabbar in points. Many of those assists became those points.

Words first, then music

For years, the composer Richard Rodgers wrote Broadway songs with the lyricist Lorenz Hart. Rodgers wrote the tune first. Hart fit words to it.

In 1943, Rodgers teamed up with Oscar Hammerstein and flipped the order. Hammerstein spent weeks on the lyrics. Rodgers set them to music fast.

Oklahoma! opened that year.

It ran for 2,212 performances, a Broadway record at the time.

Combine the right things in the right order and the benefits multiply.

⚙️

What two strengths could you combine to unlock a new one?