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“Almost everything will work again if you unplug it for a few minutes, including you.”

Anne Lamott

I made the case for cutting rest days. Reactivation energy, I called it: each gap in a habit charges a re-entry fee, so the cheapest schedule keeps each thread warm with daily work. I cut my days off and went daily across the board.

Then the binges started. Every two weeks or so a Thursday ended at 3am, deep in online chess or a show. The binge ate Friday and bled into Saturday.

For a long time I read those nights as discipline failures. Then I caught the timing. Each collapse landed right after my most disciplined weeks:

• Earlier bedtimes
• Longer meditation
• More running
• More work done

My first fix was blocking. I deleted the chess app. I blocked the site. With chess gone, a show filled the slot. The urge was for release and chess was the nearest exit.

Strength training runs on a cycle: stress, recover, adapt. The lift tears the muscle down and the rest rebuilds it stronger, which is why serious programs schedule rest days with the same care as sets and reps.

A runner who pushes past the pace oxygen can fund starts borrowing. The debt accumulates stride by stride. The pace holds for a few minutes. Then the body calls the loan and the legs slow on their own.

The brain collects the same kind of debt on a longer clock. Overextend for weeks instead of minutes and the stop arrives as distraction, procrastination or a show at 3am. My week ran the stress step on repeat: a publishing target every day, a habit list every day, seven days a week. The binge was my brain forcing the rest I kept refusing to schedule.

The binges flipped my reactivation argument. A scheduled Saturday off costs one small, known re-entry on Sunday. A binge that starts Thursday night and runs through Saturday leaves every thread cold at once and costs days of catching up. Rest looks like waste until you price the binge, the same way a backup server looks like waste until the hour it carries the whole site. I optimized away the small cost and took on the big one.

So I scheduled the rest instead. One Saturday went light:

• Marketing off
• Run off
• Deep work off

The day felt lighter before I did anything with it.

Now Tuesdays and Saturdays are off. Some weeks I feel ready to skip one. I take the day anyway. The need builds whether I feel it or not. Skipped rest comes back as another 3am Thursday.

Take the rest or your body and brain take it for you, on their schedule and at their price.

🧾

Which form of rest restores you most?

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“The way to get startup ideas is not to try to think of startup ideas. It’s to look for problems, preferably problems you have yourself.”

Paul Graham

Each day I publish a short post like this one. I started the habit with no plan to make money from it.

I wanted each post on YouTube as a video essay too. So I built Multi, a product that turns a written post into a narrated video. Now each video essay I publish is also an ad for Multi.

Problems work like nesting dolls, except the one inside can be bigger than the one you opened. Start solving any problem and you’ll keep finding new problems worth solving. Each one gives you two options:

• Take the good enough answer. Someone already built a tool that solves it. Pay up and keep moving.
• Build the answer yourself. The market has no good answer. That’s your next business idea.

Founders tell me they’re waiting for a “great” idea.

The great idea shows up after you start.

Pick the “dumb” idea, the “crazy” one. Start building it.

Marc Lou runs a portfolio of small internet products. In 2023 he noticed Stripe charged him about $1,600 in fees just to generate invoices. He went looking for a cheaper tool, came up empty and built his own in about 30 hours. He named it ZenVoice and sold it to founders with the same problem. The invoice problem only existed because the portfolio did.

Sometimes the problem you trip over is bigger than the idea you started with. When it is, switch. Slack began as the internal chat tool of a game studio whose game failed. Shopify began as store software a snowboard seller built because the options on the market frustrated him.

Start building anything and you’ll run into problems. Most come with good enough answers someone else already built. The ones with no good answer are the ideas you were waiting for.

🪆

Which problem in your daily work has no good tool yet?

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“Security is mostly a superstition… Avoiding danger is no safer in the long run than outright exposure.”

Helen Keller

One day the turkey wakes up and it’s Thanksgiving.

I left a stable consulting job in 2017. The pay was good. The work was fine. That was the problem. I was getting too comfortable. I could have stayed and pushed further there, but I wanted to spend my time learning and exploring.

Nassim Taleb uses the turkey to explain how risk accumulates. The turkey gets fed each day. Each day confirms the belief that life is good. Confidence builds. Then, without warning, the pattern breaks.

Risk doesn’t announce itself. It piles up quietly, grain by grain, then hits all at once.

We tend to think that “avoiding risk” keeps us safe. Risk is always there. Skip the small, survivable doses and it piles up into one hit that takes you out.

So dance with it. Take small risks often. Two steps up and a jump beats ten stories and a fall. Each small fall builds the skill to survive a catastrophic fall. Skip the small falls and the catastrophic fall finds you with no skill at all.

The snow is piling up on knowledge workers right now. AI handles more of the work each quarter. The role still exists. The paycheck still clears. Each month confirms the belief that things are fine. The turkey is getting fatter.

• Travel agents booked everyone’s flights and hotels until the internet let people do it themselves.
• Video store clerks ran packed Friday nights until streaming arrived and the storefronts went dark.
• A New York taxi medallion, the license to put a cab on the road, cost more than a house until ride-hailing apps made it nearly worthless.

The jobs looked stable to the last day. The ground had already moved.

Survival of the fittest leaves off the part that matters: fittest to the environment. The environment keeps moving. Stand still and the gap between you and your environment grows quietly.

Our relationships, careers, health and skills work the same way. A small discomfort now keeps you in step. Skip it and the gap widens until it breaks.

• Relationships: the weekly check-in where you say the hard thing. Avoid it and you’re signing divorce papers at year ten.
• Career: the biweekly one-on-one where the tension gets aired. Duck it and your best teammate quits before you see it coming.
• Health: the daily run or the 10,000 steps, even when it’s raining. Put it off and the heart attack arrives without warning.
• Skills: the hours each week on a new language, an improv class or a portfolio piece you ship on LinkedIn. Skip them and the next layoff has your name on it.

The turkey never sees Thanksgiving coming. Dance with risk or wait for it to hit all at once.

🦃

Where is risk accumulating in your life right now?

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“Some things are in our control and others not. Things in our control are opinion, pursuit, desire, aversion, and, in a word, whatever are our own actions.”

Epictetus

You want to start a business. Or apply for a job. Each time, you feel you should know more first.

A subscriber wrote to me after Consistent But No Progress? It’s the Hurdle Rate, looking for the hurdle rate that gets them there. The catch is small and easy to miss. A goal doesn’t have a hurdle rate.

The goal is the wrong place to look. “Start a business” and “get the job” are outcomes. They sit outside your control. You can do everything right and the business still folds. You can be the best candidate and still lose the role. You can’t put a hurdle rate on any of that. So bring it into your control. Break the goal into the habits that move you toward it.

Say the goal is the new job. The habits that feed it might be:

• Ship one portfolio piece a week
• Run one mock interview a week
• Send three cold intros a week

Each habit has a minimum input it needs to clear the entropy working against it. Below that line, you lose ground. Above it, the habit compounds. That line is its hurdle rate. And unlike the goal, that’s a rate you can clear.

One habit works for almost any goal: running experiments. It matters most when the destination is uncertain, like building a business. You can’t know in advance whether the business works. So you make running experiments a daily habit and pathfind your way there. Two a day. Three. Read the long version in the Experiments book.

Each experiment is an attempt. The attempt is yours even when the result belongs to chance. Whether you try is in your control. Whether it works out is not. So you stop staking your readiness on the outcome and start staking it on the attempts. You run enough experiments that applying is just the next one.

One more thing about a habit’s hurdle rate. It can move. The minimum input can rise. AI is one example. It can open a field to more people. When the crowd grows, the bar to stand out climbs. Where you sit decides how much. A bigger city can raise it. A bigger ambition can raise it. The three cold intros a week that cleared the line last year might take ten this year, because more people are sending them now. So you re-check the number now and then and keep paying above it.

A goal has no hurdle rate. Only habits do. So find the habits beneath your goal and clear their rates. For a destination as uncertain as a business, make experimenting one of them.

🧪

Which habits move you closer to your goal?

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“In this business, if you’re good, you’re right six times out of ten. You’re never going to be right nine times out of ten.”

Peter Lynch. One Up on Wall Street, Simon & Schuster, 1989.

I wrote a Trends Report on indie hackers.

One pattern came up again and again. They launch a lot. Most launches go nowhere. About 1 in 20 sticks around and turns into something real. They call it the 5% rule.

I see the same pattern in my own work at a smaller scale. My unit isn’t a launched business. It’s an experiment: anything I try that’s uncertain or uncomfortable. Track which ones become material wins. The rate rhymes. Roughly 1 in 20.

A material win is the rare one that keeps paying after it lands:

• Opens a door
• Becomes a tool I reuse
• Starts a trajectory I’m still on

Most experiments miss. That’s fine. A few keep paying.

So 20 is my hurdle rate: the floor I run above so the work keeps compounding instead of drifting. I’ve used the same idea on habits, where the hurdle rate is the minimum a habit needs to clear the entropy working against it.

You don’t know which experiment pays before you run it. So run more.

🎯

How does your experimentation rate set you up for regular wins?

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“There is no satisfying the senses, even with a rain of gold coins.”

The Dhammapada

Win the belt and a new belt appears. Hit the rating and the rating you want jumps higher. The finish line was never fixed.

More money, more status, more wins reset the baseline. Then you want more at the new level. Running hard keeps you in place. That’s the hedonic treadmill. In chess I want a higher rating. In jiu-jitsu I want the next belt. Both feel like destinations. Both are the same treadmill in a different outfit.

The tell comes after you reach your goal. Then the target quietly moves. The number you chased becomes the number you’re scared to lose. The belt you earned becomes the floor. You already want the next stripe. The good feeling fades.

This is wired into us. Reach a goal and you want the next one. One option is for you to see the game for what it is while you’re still playing.

Seeing the game won’t stop you from wanting more. A higher rating and a new belt reset the day you reach them.

So I spend effort where the payoff repeats. Cut one thing I hate doing and every day after it gets better. A higher rating feels good once, then the target moves.

Gratitude does the same. Each day I write down a few things I’m grateful for. You stop noticing good things once they become routine.

🎢

What are you chasing that moves the moment you arrive?

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“Plans are worthless, but planning is everything.”

Dwight D. Eisenhower

The first time I tried to make money from Trends.vc, I pre-sold the next report. Seven thousand people on the list. I figured some slice would pay up front. Zero of them did.

Ash, from my mastermind, cut in before I could spend a week regrouping. He asked why I was waiting to try again. “It didn’t work. You already have your information.” Then he pushed past my comfort: tell people it flopped. Be vulnerable about it.

That wasn’t how I operated. I did it anyway. I scrapped the report, picked a new topic and wrote a post about the pre-sell falling flat. The model changed with it. The report goes out free. You see half. The full version sits behind an upgrade.

People bought. They replied. They empathized.

I made my first hundred dollars in two hours. I went three years without a dollar from my own work. That two hours ended the streak. Within weeks the income was steady enough that going back to a job left the table.

I went in chasing one number: pre-sell revenue. I missed it. What I walked away with was the model that became the business. The target I aimed at was smaller than the thing the miss handed me.

Readers wanted more than the next report. They wanted a new one each week. So I put the reports on a subscription. The pre-sell I chased would have paid once. The subscription kept paying.

The plan failed. Running it was critical.

You aim at a target and miss. The miss drops you somewhere you couldn’t see from the start.

Your best outcome may be one you can’t name yet. You find it by running the thing that might miss.

♻️

What would you try if a miss could hand you something better?

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“Wanna fly, you got to give up the shit that weighs you down.”

Toni Morrison

I flew in and pulled cash from an airport ATM. By morning, a fraud alert lit up my phone. Overnight someone tried a second withdrawal on my card. The bank caught it and froze the card. My money was safe. My only debit card was dead.

My first instinct was to make a rule. Avoid airport ATMs. I keep a short list of rules and rewrite them regularly, so this one would ride along for the rest of my life.

Then I stopped.

This happened once. Even if it happens a few more times this decade, is that rule worth carrying for good?

This is how trauma gets hard-coded. Something bad happens. The fear stays long after the threat is gone. You live by a rule no one wrote.

I’ve written about using pain as signal. Reflect on your losses. Pull the lesson. That part holds. This is the other side. The lesson hardens into a permanent rule whose cost outgrows the rare loss it guards against.

Fear-based rules are sticky. They feel necessary. You carry them because the memory is vivid, not because the risk is high.

The better fix was a second debit card. One dies, the other works. No rule required.

Some risks earn a permanent rule, the ones that could wipe you out. Most don’t. Lock in a rule for each bad thing that happens and you become the person with 47 rules about restaurants because of one bad meal. Keep your rules lean.

🪨

What rule are you carrying that was written by a single bad experience?

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“The reasonable man adapts himself to the world: the unreasonable one persists in trying to adapt the world to himself. Therefore all progress depends on the unreasonable man.”

George Bernard Shaw

I went from two operations days a week to one. That gave me six days a week of unbroken focus. Email, support requests and coordination all get handled on the one operations day. Cut the admin time in half and everything I handle should get slower.

Email and coordination did get slower. Support requests got faster.

When I made the cut, I switched support requests from something I check to something that reaches me on its own. A notification lands the second a request comes in, instead of waiting in a queue I open on my operations day.

Most trade-offs are real. You can’t be in two places at once. You can’t spend the same dollar twice. Those are laws. You pay one thing to get another and there’s no way around it.

Some trade-offs only look real. They’re conventions everyone agreed to and then forgot were optional. The wall everyone walks up to and turns around at has a way through it. I call that way a tunnel: a route through a trade-off most people treat as a solid wall.

The best opportunities hide in the fake trade-offs. Everyone treats the wall as solid, so no one looks for the tunnel.

Here’s a tunnel you might already use. You want to read more. Books take hours you don’t have, so the reading never happens. Your commute is an hour of dead time anyway. An audiobook makes the drive your reading time.

With a real trade-off, you pay no matter what you do. With a fake one, you pay only until you find the tunnel.

🧠

Which wall could you walk through instead of around?

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“The cost of a thing is the amount of what I will call life which is required to be exchanged for it, immediately or in the long run.”

Henry David Thoreau

There are two ways to be careful with money.

One group fixates on the price tag. They compare options, hunt for deals and feel a pang when they spend. The metric is: how much did I pay?

The other group weighs the price against what it gives back. The metric is: what did I get for it?

Both are cost-conscious. One builds wealth. The other saves on every purchase and still falls behind.

I just upgraded my Kindle. It wasn’t cheap. But the old one was costing me thirty-plus minutes of deep sleep onset each night because of the screen’s melatonin suppression. “Free” was the most expensive option I had.

Cost awareness is how you get ahead. The trap is watching the wrong part of the equation. Track only the price and you’ll pass on the things that pay you back.

💸

Are you tracking what you spend or what you get back?