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“Please Note: I will not engage in work emails after 7pm or on weekends.”

Shonda Rhimes

I’m in the middle of a big habit push.

Each day I reach out to 13 people. It might be my best friend, a family member, someone I heard on a podcast, someone whose tweet I reply to or someone I’m asking on a date.

I do 8 courage challenges, up from 5 in August. A courage challenge is a hard thing I pick when nothing is making me do it.

Running went from 13 minutes to 34.

An anti-habit is a rule about what I won’t do.

As my habits got bigger, I tightened my anti-habits:

1. Fasting runs until 2pm. It used to end at noon.

2. Eating stops at 8pm instead of 10pm, so dinner is digested before bed. Sleep comes faster and goes deeper.

3. Messaging and social apps stay closed until 2pm. They used to open at noon.

4. Chess stops at 8pm, with 5 games as my daily max.

Haruki Murakami ran a jazz bar in Tokyo and smoked 60 cigarettes a day before he wrote novels full time. When he made the switch, he and his wife started going to bed soon after dark. He quit smoking.

In writing mode he wakes at 4am, writes for 5 to 6 hours, runs 10 kilometers in the afternoon and goes to bed at 9pm.

Going to bed at 9pm buys him the 4am start.

A Formula 1 car can go from 300 km/h to a full stop in under 4 seconds. Brakes that strong let a driver stay at full speed longer before each corner.

The more aggressive your habits are, the more aggressive your anti-habits need to be. They’re the boundaries that protect the time, energy and attention the aggressive habits run on.

What anti-habit can you set before you push a habit harder?

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“In times of extreme stress, the whole concept of fitness, at least in a Darwinian sense, loses its meaning.”

Elizabeth Kolbert

I’ve watched a lot of markets come and go in 6 years of building Trends.vc.

Partway through, ChatGPT arrived and intelligence got cheap.

Some markets vanished. Others grew.

Evolution can explain why one market dies and another grows.

Ecologists study how environments change. When a drought or an ice age hits, some species go extinct and some hang on in a smaller range.

Other species carry on almost unchanged, because the disruption never touched what they depend on.

Others thrive, because the disruption cleared their competition or fed them directly.

New species appear where nothing lived before.

Markets take the same routes.

Route	What it looks like in a market
Gone	The thing you sold is what the disruption replaced
Hurt	The market survives, the margin leaves
Unchanged	The market never depended on what changed
Thriving	Demand rises because of the disruption
New	A market that had no name before

1) Gone. Chegg sold intelligence, packaged as homework answers.

When ChatGPT gave the same answers away free, students stopped paying for them.

Chegg has lost about 99% of its market value since its 2021 peak near $14.7 billion.

2) Hurt. Bill negotiators phone a cable company and argue the price down. Billshark takes 40% of what it saves you. BillCutterz, running since 2009, takes 50%.

A machine makes that phone call now. Pine AI says 150,000 people have used it.

Kudos, a wallet app, sells a flat subscription instead of taking a cut.

3) Unchanged. Barbers kept cutting hair.

Machines learned to write essays before they learned to wield scissors.

4) Thriving. Electricians are in more demand because intelligence got cheap.

Each data center is a building somebody has to wire.

The Bureau of Labor Statistics projects 9% growth for electricians from 2025 to 2035, against 3.5% for all occupations.

5) New. Mercor sells expert training data for AI models.

It reached a $10 billion valuation by October 2025 recruiting ex-Goldman, ex-McKinsey and elite-law-firm people.

Take a disruption you can see coming, run a market through it and ask which of the five routes it lands in.

🧬

What could you offer that cheap intelligence makes scarce?

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“It is easier to resist at the beginning than at the end.”

Leonardo da Vinci

10 years back, my interior designer wanted to put a bar cart in my house.

Put liquor in plain sight and you’re subconsciously primed.

Move it out of sight and the thought doesn’t form.

I didn’t want bottles on display.

They went in a cabinet with closed doors instead.

In Google’s Manhattan office the candy sat out in the open, in full view of anyone walking past. Google moved the M&Ms into opaque jars and put the dried figs and pistachios into glass ones.

Over seven weeks the staff ate 3.1 million fewer calories in M&Ms.

The M&Ms were still there. Friction affected their decisions.

Shape your environment. Then it shapes you.

How can you change your environment to delete a daily decision?

“Water that is too clear has no fish.”

Dongfang Shuo

I read a memoir called Heavy a few months ago and one passage has stayed with me since.

Kiese Laymon weighed 319 pounds in college. By 26 he was running 11 miles a day, playing two hours of basketball and eating 800 calories.

He ran at least six miles a day for 2,564 days straight.

During that stretch he passed out in a grocery checkout line.

Then his mother gambled away the money he had lent her and asked him for more. They fought about it.

He ran over 20 miles that night.

He came home and stepped on the scale. Just under 160 pounds for the first time in his life.

Then his body broke. Arthritis got bad enough that he couldn’t make a stride.

He gained it all back.

With most good things, more of them does less each time. The tenth hour of study teaches less than the second did.

With a few good things, more of them starts to cost you. Six liters of water inside three hours killed a healthy woman in a radio contest.

Past a point, a good thing starts producing the harm it was protecting you from.

Where could you stop before the good turns bad?

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“Stay far from timid.”

Biggie Smalls

I read a few lines in Cory Doctorow’s Red Team Blues and put the book down. Blue team defends a system. Red team breaks in.

“That’s the problem with blue teaming it—you need to be perfect, while—”

“The red team only has to find a single error,” Cory Doctorow, Red Team Blues

Aggression has value at the poker table apart from your cards. A bet can win the pot outright whatever you hold.

The winning style has a name, tight-aggressive.

Fold most hands. Bet hard on the few you play.

The passive player is the defender, playing not to lose.

The defender can only win at showdown. The aggressor can win at showdown too or take the pot whenever the defender folds.

Each fold bleeds chips. When a timid player finally bets, opponents step aside because the raise screams strength. Chips leak on defense and the rare big hand pays almost nothing.

In chess the threat is stronger than its execution. A standing threat forces the defender to answer it on each move while the attacker keeps his options open.

Answer each move correctly and you have still spent the game solving problems someone else set.

Back at the poker table, both errors have a name.

One player only plays the top ten starting hands and folds when anyone pushes back. Phil Hellmuth named him the mouse in Play Poker Like the Pros.

Another pushes money in with any two cards and never looks at who he is up against.

The table calls him the maniac.

Good players make money off the maniac. They stop bluffing him with weak cards and let him do the betting when they are strong.

The maniac attacks everyone equally. That is the same as aiming at nobody.

In chess, overextending an attack leaves pieces exposed. You create targets instead of threats.

Unaimed aggression hands the advantage back.

Timid loses slowly. Maniac loses fast. Aim your aggression and you choose when the fight happens.

⚔️

What opportunity could you create instead of waiting for one?

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“Big doors swing on little hinges.”

W. Clement Stone

I turned off face recognition on my phone.

Unlocking by face is instant. I can be scrolling before I’ve consciously decided to pick the phone up.

A passcode adds a few seconds of friction. In those seconds I decide whether to keep going. Sometimes I type the first digit, notice I had no reason to pick it up and put it back down.

The passcode was the first.

• Red light mode. The display turns red on a schedule each evening. A red screen is ugly to scroll and better for sleep than blue or white light. That is the feature.

• No notifications. Uptime alerts break through. Everything else stays silent until I swipe down to check.

• App blockers, stacked. The first app forces a deep breath before opening. The second adds a delay and a daily limit on top. One blocker can be dismissed on a weak night, so two run together.

• Computer downtime at 9pm. Scheduled Downtime locks apps each evening. When the limit screen appears, work is done for the night.

• White noise to bed. The same sound each night masks sudden noises nearby, so fewer of them wake me. The body learns the cue too.

• All meetings and email on Monday. That buys deep work for the rest of the week.

I made each of these decisions once.

Willpower runs out. A single rule made in advance protects the day.

🔴

What boundary could you put on autopilot?

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“Nothing is so permanent as a temporary government program.”

Milton Friedman

I ran a daily standup for 2,000 days.

In 2020 I asked Trends Pro Members to post status updates with three questions:

• What did you ship yesterday?
• What will you do today?
• Where are you stuck?

Hundreds of founders joined and they logged 44,110 standups.

By the end, two or three people posted each day.

I ended the standup on day 2,000 and shipped a book built from the standups the same week.

The book took a week. Ending the standup took years.

Run an experiment. It shows a spark of demand. People start using it, so now you have to keep it working for them. Run eight experiments that each get a little traction and you’re running eight projects you decided to keep by default.

Shipping 12 startups in 12 months sounds great to me. I want to try a lot of ideas and find the few that stick.

The experiments that kinda work are the trap.

A call option gives you the right to buy something later without the obligation to buy it. I want an experiment to work the same way. Upside if it lands. Room to walk away if I’d rather spend the week elsewhere.

I ended the standup, but it took 2,000 days. Walking away sooner takes practice.

Some moves I’m considering to keep experiments optional:

• Ship the experiment with an end date. Let the people using it buy the extension.
• Hand it to someone to run it. The experiment keeps running and I stop being the one asked.
• Presell it against a number. Take orders until a count is hit. Miss the count and the experiment never starts.
• Sell the experiment. Get good enough at selling a small business that handing it over is a move I can make in a week.

A thing that works is harder to end than a thing that fails.

🧪

What rule keeps your next experiment from becoming a commitment?

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“Be regular and orderly in your life, so that you may be violent and original in your work.”

Gustave Flaubert

I was on a Trends.vc Masterminds call when the host opened with a question for the room.

“What’s the latest move you made where the payoff wildly outran what it cost you?”

Curfew was my answer, a small app I built that blocks YouTube on my laptop until 4pm.

For months I watched YouTube, at times up to 5am.

In Curfew, I set one boundary, a window that blocks YouTube outside of 4pm to 9pm. That boundary gave me back at least 15 hours a week.

The novelist Jonathan Franzen believed he couldn’t write serious fiction on a computer that could reach the internet, so he pulled the wireless card out of an old Dell laptop. That left the ethernet port.

“What you have to do is you plug in an Ethernet cable with superglue, and then you saw off the little head of it.”

That permanently blocked internet access on his machine.

Automate the boundary and you decide once. Leave it to willpower and you decide again each day.

⛔

What are you re-deciding daily that you could automate once?

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“I have to write to discover what I am doing.”

Flannery O’Connor

I run most days and listen to health podcasts. A few weeks ago I heard something I had to rewind: strength and muscle are correlated but they are different things.

Until then I thought bigger muscle just meant more strength.

Muscle is the capacity to produce force.

Strength is how much of that force your nervous system can fire at once.

You can grow a lot of muscle and still only use part of it. A lifter can also get much stronger while the muscle barely changes size.

For the first few weeks of lifting, most of the strength gain comes from your nervous system learning to fire what you already have. After three to five weeks, more of the gain comes from the muscle getting bigger.

Dickie Bush tells a story about two fishermen who had never cast a line.

The first fisherman went straight to the marina.

He bought a boat and specced a carbon-fiber rod.

He read books on casting, baiting and reeling.

He watched the fishing channel each night for months.

When he finally felt ready, he took it out.

Six hours later he had not had a single nibble.

The second grabbed a shitty rod, sliced up a hot dog and went to the lake on day one.

For a week he caught nothing.

On the eighth day he got his first nibble.

He moved spots and changed bait.

By the time the first fisherman showed up, the second had already been iterating on the water for weeks.

The first fisherman spent months gathering gear while the lake was being learned by someone else.

Make progress first. Then you can optimize later. They are different things and that is worth knowing.

Early on it barely matters which lever you pull. A beginner improves on almost any work.

Muscle and strength both climb inside the first couple of months.

The mistake is arguing about which one to train before you have trained either.

💪

What could you start before you know the best way?

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“The most common way people give up their power is by thinking they don’t have any.”

Alice Walker

I tried to learn Spanish for years and never consistently found the time. Any hour I gave it came straight out of something else I needed to do.

So I started studying Spanish while I run.

The course is Language Transfer, an audio method where a teacher asks you to build the sentence yourself before he gives it to you.

A 2013 paper in PLOS ONE found that young women who exercised while learning vocabulary recalled more of it than those who sat still through the lesson.

Breakout is an arcade game where a paddle keeps a ball alive against a wall of bricks. Track the ball better and you break more bricks. One miss costs a life.

An AI learning the game refused that trade. It opened a gap up one side, sent the ball above the bricks and let it ricochet until the wall was gone. The paddle barely moved.

Tunneling is finding out that a trade-off you thought was mandatory was optional all along.

For years the novelist Kevin J. Anderson had to pick between a day of writing and a day of hiking.

Then he started carrying a voice recorder up the trail and dictating chapters as he walked, one chapter out and one back, since he had to walk back anyway.

In 2010 he counted nearly 50 novels dictated into a recorder.

One week he hiked 50 miles and wrote 168 pages.

For the management thinker Nilofer Merchant, taking care of her body and being productive were in conflict. Then she started taking her one-on-ones as walks.

By 2013 she was walking 20 to 30 miles a week inside meetings she was going to have anyway. Then she got on the TED stage and told everyone else to try it.

Stacking a second activity onto one you already do is one route through.

Test trade-offs before you accept them.

🏃

Which trade-off could you try to tunnel through?