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“Error is the engine of evolution.”

Stewart Brand

The drugs were killing people.

In April 1989 the safety board stopped the Cardiac Arrhythmia Suppression Trial.

For years, cardiologists prescribed encainide and flecainide to suppress abnormal heartbeats after an attack. The logic seemed airtight: if irregular rhythms trigger sudden death, suppressing the beat should save lives.

The study tested that assumption across more than 1,700 patients.

When the safety board compared the double-blind columns, 56 patients on the active drugs died, compared to 22 on the placebo.

Halting the trial stopped a lethal practice that was quietly killing thousands of people each year.

The stakes in medicine are life and death, but the same rule applies to any system. Testing an assumption exposes you to temporary downside to discover what actually works.

I face a low-stakes version of this tradeoff on the Trends.vc email join page.

The page converts above 20%. Pushing for a higher conversion rate means running split tests.

When a baseline is already high, most new variants perform worse.

Each test routes visitors to an unproven design. Some variants shed subscribers before we restore the original baseline.

The short-term numbers look worse.

Short-term downside risk is the price of testing. Running an experiment means accepting temporary dips to discover what actually works.

When an offer or routine is already working well, your natural instinct is to leave it alone. Testing carries immediate downside risk. Why touch something that works?

In 1973 a biologist named Leigh Van Valen looked at extinction rates across the fossil record. Within any group of organisms, the probability of extinction stays roughly constant regardless of how long a species has already survived. Age buys no safety.

His explanation was simple: competing species keep evolving, so improving only keeps you level.

Major journals rejected the paper.

So Van Valen founded a journal called Evolutionary Theory and made his manuscript the first paper it published.

He named the principle after the Red Queen in Lewis Carroll’s Through the Looking-Glass.

The Red Queen forces Alice to sprint in place: “Now, here, you see, it takes all the running you can do, to keep in the same place.”

Standing still guarantees that entropy and competing operators will overtake you.

Most experiments pay nothing. Most attempts drag your metrics down before you find what works.

Each attempt at better opens a door to worse. You pay the short-term drop to find the rare change that compounds.

⚗️

What working routine will you test to make it better?

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“Extreme people get extreme results.”

Sam Altman

He turned down the extra guns and rode in anyway.

In the summer of 1876, George Custer was offered Gatling guns before marching to the Little Bighorn. He said no.

Captain Edward Godfrey remembered the reasoning. They might hamper the movement at a critical moment.

He was also offered two more cavalry companies. Taking them would have roughly tripled his force to around 2,500.

He declined those too.

At the river he split his command four ways. Reno and Benteen took three companies each, about 120 apiece.

Custer rode north with the rest. Each of the 210 men who followed him died. So did he.

Protecting his speed by refusing artillery and extra troops turned an aggressive move into a reckless one. It wiped out his entire command.

I got back into poker recently and the app I use grades aggression on a scale.

It tracks pre-flop raises, steal attempts and re-raises. Then it slots players into five bands: mouse, passive, balanced, aggressive and maniac.

A mouse checks and calls instead of raising. A maniac bets and raises with almost anything.

The scale struck me because it names a spectrum that applies outside the game.

I started slotting my habits onto it. At this floor, am I a mouse, passive, balanced, aggressive or a maniac?

Courage challenges are the clearest case. My floor is 5 a day. That sits between balanced and aggressive.

Pushing that floor to 13 a day would push me into maniac territory. I would be taking reckless risks just to feed the count.

Sam Altman wrote in 2019 that extreme people get extreme results.

He said nothing about those results being good.

Custer was extreme and got an extreme result. The maniac at a poker table gets an extreme result: they either stack everyone or go broke before the night ends.

The far end of any scale is where the largest outcomes live, in both directions.

My first reaction to the scale was that I didn’t want to be a mouse. Nobody does. It sounds like the worst position on the chart.

The worst position sits off the chart entirely.

A mouse who checks and calls still has a seat, a stack of chips and a shot at the pot. Someone who never sat down holds none of those.

Playing timidly still beats not showing up.

In areas that carry your highest ambitions, a passive setting bleeds opportunity. You have to push the pace.

Where you just need to cover a base or maintain a baseline, a mouse setting does the job. Sizing the habit to the bare minimum keeps the system moving without draining energy from what matters most.

Aggression decides how much you win. Presence makes winning possible at all.

🎛️

What habit are you running on the wrong setting right now?

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“Deciding what not to do is as important as deciding what to do.”

Steve Jobs

I turn off my phone at 10pm each night.

My laptop closes at 9pm. Work finishes by 4pm.

Messaging apps stay closed until 12pm. Coffee stays off the menu, with all caffeine ending by 10am. Meals happen only between 12pm and 10pm.

My diet excludes sugar, rice, fried food, grapes and watermelon. Red meat appears only on Tuesdays and Saturdays. Chess and poker wait until work ends and stop by 8pm.

These 10 rules are anti-habits.

Commitment habits are the actions chosen for execution: meditating for 2.5 hours, running for 13 minutes, doing 21 experiments, finishing 5 courage challenges and reaching out to 5 people a day. Each demands time, energy and working memory.

Standard advice focuses on what to add: morning routines, daily disciplines and habit stacks. But adding more disciplines increases fragility.

The more parts a system has, the more prone it is to breaking. Adding more tasks increases context-switching and makes a daily routine fragile. To keep work reliable, you must put a strict limit on active commitments.

Anti-habits protect capacity by deciding what stays outside.

A refusal requires zero runtime execution, so you can maintain dozens of boundaries without cluttering your day. Turning off a phone at 10pm protects sleep, making the next morning’s schedule far more likely to hold.

Under the Federal Aviation Administration’s Sterile Cockpit Rule, flight crews cannot chat, eat or read non-flight material below 10,000 feet. The policy protects the pilots’ attention so they can execute critical checklists during takeoff and landing.

In surgery, teams maintain a sterile field around the patient. Staff hold their hands above the waist, keep unsterilized tools off the tray and leave unscrubbed visitors outside the perimeter. The barrier stops contamination so the surgeon can finish the operation safely.

When your routine starts to break down, adding more disciplines exhausts the system.

Instead of piling on new tasks, set anti-habits on what you refuse to do.

🛡️

What anti-habit would make your most important commitment habit easier?

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“You never know what is enough unless you know what is more than enough.”

William Blake

I cut my team’s one-on-ones from every 2 weeks to once a month. Stretching the schedule looked like a clean win: fewer calls and more hours back.

Alignment broke instead. Feedback piled up, expectations pulled apart and reconciling the drift took more time than the calls I set out to save. I moved them back to every 2 weeks.

Stretching the time between calls revealed the hurdle rate for team alignment: 2 weeks kept us aligned, 4 weeks fell behind.

Each habit has a hurdle rate: the minimum input the system needs to clear what pushes back on it.

Entropy pushes back on each habit: competition, fatigue, things going wrong, life. Run below the rate and you lose ground, however faithfully you show up.

In 1966, researchers at the University of Texas Southwestern put 5 healthy 20-year-olds on complete bed rest for 3 weeks. 3 weeks of lying still dropped their aerobic capacity by 27 percent.

30 years later, cardiologist Benjamin Levine measured the same 5 men as 50-year-olds. 30 years of natural aging only reduced their fitness by 12 percent.

3 weeks of zero input cost them more conditioning than 30 years of aging.

The Silver Bridge had no regular inspection schedule when it collapsed into the Ohio River in December 1967. 46 people died.

Investigators traced the disaster to a single crack in 1 steel eyebar. In 1971, the federal government established the first national bridge safety standard: every 2 years by a trained inspector.

It took 46 deaths to discover the minimum check a suspension bridge needs to survive.

Pay below the hurdle rate and you lose ground. Pay too far above it and you waste energy on diminishing returns. You find a habit’s hurdle rate by lowering what you put in until progress slips, then returning to the input that held.

📉

Which habit could you trim until you feel the floor?

“He who is too busy doing good finds no time to be good.”

Rabindranath Tagore

He built the biggest jewellery chain in the world. Then he stood up at the Royal Albert Hall and called his products crap.

Gerald Ratner was speaking to 6,000 business leaders at the Institute of Directors on 23 April 1991. Someone asked how his shops sold things so cheaply.

One sherry decanter was priced low “because it’s total crap,” Ratner told the audience. A pair of earrings cost less than a prawn sandwich from Marks and Spencer. The sandwich, he added, would probably last longer.

The room laughed.

Ratners lost around £500 million of its value, the board removed him the next year and the chain was renamed.

One joke cost him the company he spent decades building.

The same trap appears the moment you do something good.

I ate a smash burger recently after sticking to my diet all month. The excuse was that I earned it. My body and brain felt sluggish immediately after.

Sticking to my diet gave me an excuse to cheat.

You finish 4 hours of focused work, complete a hard workout or eat clean all day. Then your brain treats that effort as permission to slack off. The reward wipes out the progress you just made.

Self-sabotage usually wears the costume of a reward.

To protect your progress against self-sabotage:

• Treat good habits as the standard. Sticking to your routine is the baseline rather than a favor that unlocks credit.
• Decide the reward beforehand. Pick how you celebrate before you start the work. Choosing a reward while riding a high leads to bad choices.
• Never reward a habit by breaking it. Do not celebrate a clean diet with junk food or a frugal week with a shopping spree. Reward the habit with things that keep it going.

A good day builds momentum. Spending it as permission is how you give that momentum back.

🧾

What progress have you given yourself permission to erase?

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“The fastest way to still the mind is to move the body.”

Gabrielle Roth

A man who broke rock all day in a prison quarry went back to his cell and ran in place.

Swinging a hammer at limestone all day was how the state planned to wear Prisoner 46664 down.

He added 45 minutes on the spot to the end of it. Then 100 fingertip push-ups, 200 sit-ups and 50 deep knee-bends.

Nelson Mandela ran that routine Monday through Thursday.

His cell on Robben Island was about 7 feet across. He kept the routine for most of the 18 years he spent there.

It came from his boxing years and he later wrote down what it was for.

“Exercise dissipates tension.” He said he “worked better and thought more clearly when I was in good physical condition”.

The training was the one part of his day the state didn’t control.

When I feel down, depressed or hopeless, the things that reliably shift it are physical:

• A run.
• Mobility work.
• A cold shower.
• Hard intervals.
• Strength training.

Each one is voluntary discomfort.

Exercise is an antidepressant.

James Blumenthal’s team at Duke ran the comparison. 202 adults with major depression, 16 weeks.

Remission at 4 months: 45% on supervised exercise, 40% doing it at home, 47% on sertraline, 31% on a sugar pill.

Almost a third of patients improved on a placebo. Exercise added 14 percentage points and matched the prescription drug.

One year later, patients who kept exercising stayed in remission.

Movement is medicine.

Charles Dickens walked at night for years.

In October 1857, he left his house in Tavistock Square at 2am and walked to Gad’s Hill Place near Rochester. 30 miles, in about 7 hours.

He did a version of that often, roaming London from midnight to dawn.

Walking 30 miles in the dark was how he wore out his body to quiet his head.

When you’re stuck you have time on your hands and you spend it making the case for how bad you feel.

A cold shower breaks that loop and forces your attention somewhere else. It gives you distance and shifts your physical state before you return to the problem.

So does a run. You can’t hold an argument with yourself while you’re gasping.

Next time a bad day lands, move first.

Get into your body to get out of your head.

🏃

What movement could clear your head today?

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“No one tests the depth of a river with both feet.”

Ashanti Proverb

I wrote code for 3 hours before work each day. It was 2012 and I was building Shommi, a tool that tracked Twitter to find potential customers for businesses. I told myself a working solution would sell itself.

After 3 months I ran out of things to improve. On a Saturday I drove to a strip of car dealerships on the north side of Atlanta and walked into 3 of them. I told them people in their area were tweeting about buying cars.

They were polite and said “interesting.”

The most interested person at those 3 dealerships wanted to hire me for Ruby on Rails contract work.

3 months of mornings bought 1 Saturday’s worth of information.

Long feedback loops make finding out expensive. Short loops make failure cheap.

Unilever’s mathematicians tried to design a detergent nozzle first. Fluid dynamics and phase transition were their specialty.

The nozzle clogged anyway.

Unilever’s biologists came at it without the theory. They made 10 variants, kept whichever sprayed 1 or 2 percent better, made 10 variants of that one and ran the loop again.

45 generations later, they had a nozzle shaped unlike anything the mathematicians designed.

449 rejects bought a nozzle that sprayed many times better.

13 years after Shommi, I changed the scale of the test. I paid hours instead of months to test the idea that became HeadsUp. I handcrafted Notion documents laying out what each founder’s competitors were doing and sent them to 8 founders.

One offered $300 a quarter before a line of code existed.

Google runs 12,000 split tests a year because each test is cheap to run. In 1 test on 41 shades of blue, a single color shift added $200 million in annual revenue.

Saras Sarasvathy sat 27 expert entrepreneurs down with the same startup problem and had them think out loud. They set what they can afford to lose before they start, then skip forecasting what they might gain. She named it affordable loss.

Size each test so a miss can’t finish you.

📄

What test could you shrink until failure is cheap?

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“Without reflection, we go blindly on our way, creating more unintended consequences, and failing to achieve anything useful.”

Margaret J. Wheatley

I write one number for each day, somewhere between -4 and +4, to score how the day went. I call it my tempo.

Two questions follow each night:

1. If the day was less than 4: What would have made it a 4?
2. If it was 4: What made it great?

I built an app called Apex to correlate my habits against my tempo, sleep and mood.

The habits that add the most points to my tempo:

• Cold showers: +0.7
• No phone after 10pm: +0.7
• No laptop after 9pm: +0.6

On days I take a cold shower, I get to bed 21 minutes earlier.

Reflection is the engine of progress and the number is what gives it something to run on.

Compress a day to one digit to see what actually made the difference.

📊

What number would you give today?

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“If I waited for perfection, I would never write a word.”

Margaret Atwood

I chose the model that writes for Multi off a public ranking and it still gets things wrong.

Arena ranks frontier models on text, code, image, video and search. New entries keep landing near the top.

A research group called METR measures the longest job an AI can finish on software tasks. They size that job in how long the same work would take a person.

The length doubled roughly every 7 months.

A model counts as finishing when it comes out right half the time.

From 2019 to 2025 that adds up to about a thousandfold.

A tool that finishes your work half the time is a coin flip you still have to check. Each better model takes a bigger piece of the work off you.

Launch your product with the best model now and swap in better models as they arrive. Or keep waiting and better models arrive while you still have no product or users.

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What could you launch now, then upgrade as tools improve?

“The opposite of a profound truth may well be another profound truth.”

Niels Bohr

“You don’t want to make money by screwing your investors,” Charlie Munger said. That, he said, is what a lot of venture capitalists do.

Two podcast hosts had him in front of a microphone and asked whether venture capital does its job in society. He said no. The people doing the work inside those businesses often “hate the venture capitalists.”

His complaint was about how the money gets made.

He and Buffett made their money by buying businesses whose customers would want the same thing in 20 years. Buffett wrote the rule down in 2007. Their criterion of “enduring” ruled out companies “in industries prone to rapid and continuous change,” because “a moat that must be continuously rebuilt will eventually be no moat at all.”

Berkshire could buy once and hold for decades.

Betting on what’s changing pays too. Venture investors fund young companies built around a market or a technology that’s moving right now. Nobody can tell which one takes the market.

Paul Graham ran Y Combinator. He put the math in writing: “for each big winner we could pick a thousand companies that returned nothing and still end up 10x ahead.” So they fund many and let the winner show itself.

By the time he wrote that, Dropbox and Airbnb carried about three quarters of everything Y Combinator funded.

In the same interview, Munger said venture capital is “a very legitimate business if you do it right.”

What if you want to do both?

Amazon used the changing market to pick its moment and the unchanging wants to pick where the money went. Amazon’s 1997 shareholder letter described a “window of opportunity” in online commerce and called the moment “Day 1 for the Internet.”

In October 2007 an interviewer asked Bezos how Amazon sets its strategy. People ask him constantly what will change in the next ten years. Nobody asks him what will stay the same.

That second question set where the money went:

• lower prices
• broader selection
• faster delivery

“All the energy you invest in them today will still be paying you dividends ten years from now.”

Both strategies work.

The open question is which one suits you. The same strategy that wins for someone else can lose for you.

🎲

Which approach feels right for you?