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“A chain is no stronger than its weakest link.”

Thomas Reid

I tried more than 20 businesses before one of them worked.

One or two made a little money. None of them got big.

I worked hard on each one.

These days I split my focus across five areas. Physical health, mental health, social life, wealth and wisdom.

Looking across those five areas revealed the problem. I spent those early years working in isolation.

I am introverted, so social connection was the hardest area for me.

In 2019 I joined a mastermind called Zero to One.

Those founders inspired me and held me to what I said I would do.

Trends.vc came out of that room.

I spent years taking care of health, mindset, learning and money. Trends.vc would not have worked if I stayed in isolation.

Think about an investment portfolio.

You can hold thousands of stocks. But if they all sit in one category, you are underdiversified.

Picking best-in-class assets across four sectors does not protect you when a market downturn hits all four at once. You focused on picking winners, but you left the fifth category empty. Without an uncorrelated asset to balance the drop, a broad decline in your main holdings can wipe out the entire fund.

Survival is not about how many assets you own, but whether you covered critical categories.

The same imbalance shows up in the gym. We all know the guy with a massive chest and arms who skips leg day. He looks formidable until someone glances down.

You cannot outwork a blind spot by doubling down on your strengths.

If a critical area is empty, that single gap can still take you out.

🛢️

How could you cover an underdeveloped area of your life?

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“Now the general who wins a battle makes many calculations in his temple ere the battle is fought.”

Sun Tzu

Each day I ask one question.

What’s the one thing I can do that makes everything else easier or unnecessary?

Lately I’ve started putting a time estimate next to the answer.

Estimating the work forces a simulation.

To set the number, you picture the steps. You see where to begin, what you need on hand and what finished looks like.

That mental walkthrough is priming.

Hospitals treating a blocked artery run against a deadline of 90 minutes.

Door to balloon, they call it. The clock runs from the front entrance to the moment a catheter opens the artery. In 2005 fewer than half of American patients beat it.

A 90-minute deadline leaves no time to coordinate after arrival.

Hospitals started the sequence before the patient reached the door. A paramedic sent the heart tracing ahead from the ambulance. One call activated the lab.

By 2010 the national median fell from 96 minutes to 64. The share of patients inside the window went from 44% to 91%.

An estimate is a rehearsal. You walk the path before you start the clock.

⏱️

Which project would you estimate to start moving?

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“A story is a way to say something that can’t be said any other way.”

Flannery O’Connor

When I wrote my first Trends.vc reports, I focused on density. Each report was raw research, clear data, judgment and conclusions.

Each good piece of content does one of two things.

It makes you afraid to stop consuming. Or it makes you unable to stop consuming.

Same outcome, different mechanism.

The first path is signal-to-noise. The reader stays because each sentence delivers value.

“What will I miss if I leave?”

The Economist does this. Trends.vc reports do this.

Dense research where skipping a paragraph might cost you an insight worth thousands of dollars.

The reader gets smarter by the minute.

The second path is escapism. The viewer stays because the story won’t let them go.

“I can’t walk away.”

Netflix does this. Serialized storytelling does this.

The viewer gets so deep in the world that leaving feels like withdrawal.

Great comedians and edutainment pull off both.

Each piece needs at least one.

Without signal, there is nothing to learn. Without story, there is no reason to stay.

📡

What will your next piece optimize for: signal or story?

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“Stability is destabilizing.”

Hyman Minsky

I’ve tracked my habits for 15 years. When I hit them consistently for a stretch, I add more on the strength of that momentum.

Each time the list grew too long, the routine fell apart and habits went uncompleted.

During my mini-retirement I was biking around Atlanta listening to the Indie Hackers podcast. I heard Courtland Allen describe how his habit tracking kept collapsing.

Capping the list stopped the collapses for me.

Over Christmas 2022, Southwest Airlines lost track of where its pilots and flight attendants were. Michael Santoro, vice president of the pilots’ union, told CBS News the airline saw a meltdown once or twice a year. The scheduling software couldn’t keep up with changes across the network.

Crews sat waiting to be told where to go. Lyn Montgomery, leader of the flight attendants’ union, said hold times ran anywhere from three to 17 hours.

Southwest cancelled 16,900 flights over the holiday and went back to matching crews to planes by hand. In December 2023 the Department of Transportation fined it $140 million.

I’ve never run an airline.

I’ve run a list of habits past what it could carry.

Sweden started building the Vasa in 1626. On top went a deck structure built heavier than the guns called for, 64 cannons, 120 tonnes of ballast and close to 500 sculptures across the stern.

Before she sailed, 30 men ran back and forth across her upper deck to see how she rolled. Vice Admiral Klas Fleming stopped them after three passes, worried she would go over at the quay. She sailed anyway.

On 10 August 1628 the Vasa traveled 1,300 meters, caught a gust and went down in sight of the yard that built her.

Somewhere between 30 and 50 people drowned that afternoon.

No single cannon capsized her. The additions simply ran out of hull to carry them.

I’ve added habits until the day had no room left.

Joseph Tainter’s answer for why complex societies end is that they accumulate their way there. Each layer a society adds to solve a problem returns less than the layer before it, while costing the same or more to keep running.

Systems rarely collapse from a catastrophic failure. They collapse under the weight of too many reasonable additions.

🏛️

What protective limit could you set while things are calm?

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“There are no solutions, only trade-offs.”

Thomas Sowell

All of my meetings are on Mondays.

Masterminds, team calls, one-on-ones and email run back to back without a break.

By evening I am out of words.

The other six days my team is the filter. A real fire reaches me. A small one waits until Monday.

That subtraction costs me speed. Send me something on Tuesday and you hear back the following Monday. But it buys six days of unbroken focus.

Each strength is funded by a deliberate weakness.

Costco chose to sacrifice markup and selection. It caps markup on branded products at 14% over cost. Kirkland Signature, its own label, gets 15%. Most retailers work on 25% to 50%.

Costco stocks around 4,000 items.

A typical supermarket carries 30,000.

Stock 30,000 items and you buy less of each one. Smaller orders cost more.

By capping markup and limiting items, Costco bought massive volume. The membership fee carries about half the operating profit, paying for low prices all along.

Southwest Airlines cut comfort to buy turnaround speed.

It built its operation around a single aircraft type, the Boeing 737.

• One set of spare parts
• One training course for pilots and mechanics
• Crews that move between aircraft with far less retraining

The airline also skipped assigned seats and meals. Flights ran point-to-point rather than routing everyone through hubs.

Those subtractions bought faster turnarounds, more flights per aircraft each day and lower fares. Assigned seating finally arrived in January 2026.

Both companies protect what they actually sell.

Costco sells trust that the price is the lowest available. It can keep margins tiny, but it cannot lose buying power.

Southwest promises cheap seats that leave on time.

Meals and comfort are easy to cut. Turnaround speed is not.

Costco gave up margin. Southwest gave up comfort. I give up response speed.

Pick what you will be worst at, then earn it by being extreme elsewhere.

🐢

What could you neglect to buy room for your biggest strength?

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“Divide each difficulty into as many parts as is feasible and necessary to resolve it.”

René Descartes

Each day I read one of my rules: “Resistance is a sign that the step is too steep.”

When you procrastinate on a project, the instinct is to blame your discipline. But avoiding the work does not mean you are lazy. It means the step in front of you is too steep.

In 1951, John Steinbeck sat down to write East of Eden. The scale of the book terrified him. He delayed starting, paralyzed by the mountain of work ahead.

Whenever he thought about writing an epic novel, a sick sense of failure stopped him cold.

If you have ever stared at a blank screen, you know that stall.

His breakthrough was shrinking the step until it was impossible to avoid. He knew that looking at the whole mountain makes you freeze:

“Write just one page a day, that is all. Be aware of it only as a single page.”

Chopping the monolith into a single daily slice dissolved the dread.

The book was finished in a year.

When a project feels overwhelming, you back away. The resistance is not a character flaw. It is a measurement problem.

Your brain stalls when an large outcome pretends to be a single task.

Monoliths invite avoidance because they offer nowhere to start.

Separate preparation from execution. Shrink the first move until starting takes less effort than putting it off.

Once an outcome turns into an atomic sequence, the resistance disappears.

📄

What stalled task could you split into two startable steps?

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“They’re hands you can lose a lot of money with.”

Doyle Brunson

I looked down at a king and a nine on my phone. In my headphones, Maria Konnikova was recounting her lessons from Erik Seidel in The Biggest Bluff.

Seidel warned her that king-nine is an expensive trap. Amateurs see a face card and stay in the hand.

He tends to fold it because a weak side card leaves you drawing to second-best.

The obviously terrible hands are easy. You throw them away in half a second and wait for the next deal.

Those hands don’t drain your stack because folding them takes no thought.

Holding a king looks playable. At a table with fewer opponents, it looks even better.

When the flop pairs your king, you think you’re ahead.

Someone else often holds a king with an ace beside it.

If an opponent is behind, they fold early, so you win a small pot. If they hold ace-king, they call each bet and take your whole stack.

Doyle Brunson called cards like king-nine trouble hands for a reason.

They keep you around long enough to lose your chips.

You see the same dynamic in business.

In 1962 Warren Buffett started buying Berkshire Hathaway stock, a declining textile mill that looked like a bargain at $7.50 a share. It was a classic borderline trade: a cigar butt with one free puff left.

Two years later the mill’s president agreed to buy Buffett’s shares back at $11.50 each. The written offer came in at $11.375. Buffett was angry enough over 12.5 cents that he bought up the rest of the stock, took control of the mill and fired him.

If you have ever doubled down on a mediocre hand instead of walking away, you know how that goes.

For the next 20 years, Buffett poured money into new looms and equipment, trying to turn around a business bleeding to foreign competition. Each improvement was matched by competitors.

By 1985 he closed the mills, calculating the distraction cost over $200 billion in compounding gains.

It was his worst trade: you can pour a fortune into new looms, but a dying business never becomes a winner.

Charlie Munger later explained the fix. On their desks sat a wooden box labeled “Too Hard.”

If you bring them an opportunity that is complicated, borderline or requires heroic effort, they toss it into the box and wait for an obvious pitch.

Derek Sivers framed the same filter as a choice between hell yeah or no. Unless you feel an immediate yes, the answer is no.

Terrible ideas are easy to reject. Nobody struggles to turn down an offer they hate.

The rule exists for the 7 out of 10.

The client who pays okay but drains your weekend. The project that works only if conditions stay perfect.

When an opportunity sits on the edge, we negotiate with ourselves. We look at the face card and ignore the weak kicker.

Passing on borderline ideas protects your time for the rare opportunities that are an obvious yes.

♠️

What borderline project should you fold today to protect your time?

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“It is by teaching that we teach ourselves, by relating that we observe, by affirming that we examine, by showing that we look, by writing that we think.”

Henri Frédéric Amiel

I gave up daily writing in my early 20s. Life got chaotic and the habit felt expendable.

The next week, my life felt the same.

The cost had a delayed effect.

By the time my learning and clarity slowed down, I stopped connecting the slump to the habit I dropped.

Writing organized my thinking and taught me how to tell a story. The practice created a public record of lessons, making me less likely to repeat the same mistakes. It built discipline and helped me scale myself.

To explain an idea in public, I had to see where my understanding was weak. Half of what I learned came from making ideas make sense to strangers.

Writing looks solitary, but it put more people in my life than any conference.

When you drop a habit, the damage is rarely immediate.

✍️

What did you figure out recently that you could share?

“As debt increases, you narrow the range of outcomes you can endure in life.”

Morgan Housel

I plan to put my phone down at 10 each night. If nothing is due tomorrow, 10 turns into midnight.

Without a deadline tomorrow, I take tonight less seriously and stay up late.

In 1955 British historian Cyril Northcote Parkinson wrote that work expands to fill the time available for its completion.

The same rule governs evenings. Give a task a week and it takes the week. Give a night no reason to end and it stretches to midnight.

On Mondays I stack four or more calls: two masterminds, a team call and a one-on-one. Back-to-back conversations leave no buffer. By afternoon my energy drops.

A packed schedule works only when nothing goes wrong.

One late call or one small fire and the rest of the schedule collapses.

Morgan Housel describes debt the same way. The more of it a company carries, the fewer scenarios it survives.

A company with no loans can sit through a recession. A leveraged one dies in the downturn.

Calendar commitments work like financial debt.

Stack too many and one surprise wipes out the day.

An empty schedule fails from underuse. With nothing to push against, simple tasks expand to fill the whole day.

Housel runs his days at 80 or 90 percent of capacity for the same reason.

“I’m not interested in anything that’s not sustainable. Friendships, investing, careers, podcasts, reading habits, exercise habits.”

I want enough due tomorrow that tonight ends on time and enough slack that a surprise costs an hour instead of the day.

A packed day breaks from overuse. An empty day atrophies from underuse.

⚖️

What could you drop from your fullest day so one surprise can’t sink it?

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“Dig a well before you are thirsty.”

Chinese proverb

I can skip a day of marketing now and the streak holds.

Marketing takes 34 minutes. For months, missing one day broke the chain.

I built an app that lets me bank ahead: do tomorrow’s block today and the credit carries forward.

Right now I have a few days sitting in the bank. I don’t have to touch the work today to keep the streak.

And yet I did today’s block.

Researchers found something close to this in a sugarcane field.

Sugarcane farmers in India get paid once a year, in a lump at harvest. The same man is broke the month before and flush the month after. The researchers tested more than 400 of them on the same puzzles before the payout and again after.

Afterward, with money in hand, they scored much higher. Same farmer, same brain, richer by one crop.

That score gap matched a lost night of sleep or 13 IQ points.

When I read that, I saw my mornings in it. The shortage left the farmers with less attention for planning ahead and staying steady.

They called it a tax on bandwidth.

Take the shortage away and the tax disappears.

Habit banking gave me that bandwidth back. The real burden was the daily worry of missing a day.

A rough day spends savings instead of breaking the chain. The panic drains out.

Habit banking helps most where the deadline creates the pressure.

A reserve removes the risk of snapping the streak and the stress about it.

You still do the work, but the dread is gone.

🏦

Which daily habit could you get one day ahead of?