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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?

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“Today’s problems come from yesterday’s ‘solutions.’”

Peter Senge

On a run last week I heard Travis Kalanick explain why taking Uber into China was a problem he chose to create.

Kalanick believes a company has to solve problems at least as fast as it creates them.

Around 2013 he took a few of Uber’s earliest employees to China. One person there told him it was the worst idea ever.

He took that as a good sign.

By early 2016 Uber was losing more than $1 billion a year in China. That August it sold its China business to its local rival Didi.

Its problems there piled up faster than it could solve them.

Mike Isaac tells the story in his book Super Pumped.

Since each problem I solve creates new problems, I work in priority order.

When I work on my second or third most important problem, I create the wrong problems. The new problems from those lower priorities pile up and pull me further from my most important problem.

Work on your most important problem first and the new problems you create are the right ones.

🎯

What’s the most important problem for you to solve right now?

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“Spend each day trying to be a little wiser than you were when you woke up.”

Charlie Munger

I spent 3 years trying to find a business idea.

Mobile apps came first, then SaaS ideas. I let each one go.

Then I changed the question. I stopped asking which idea was best and asked what I could see myself working on the longest.

The answer was exploring how businesses and markets work. I could spend years spotting opportunities and finding what links one market to the next. I was already doing it for free.

That became Trends.vc.

Starting a business is like trying a blank key in a door.

It won’t turn the first time. So you go back, reshape the key and try the lock again.

The longer you’re willing to keep reshaping, the more likely the door opens.

In 2003 Niklas Hed and two friends from university started a game company in Finland.

Over the next 6 years they shipped 51 games. By then the company was close to bankruptcy.

They made one more.

Number 52 was Angry Birds.

Your first idea is like the first cut of that key.

Before you ask what the best business idea is, ask what you could see yourself working on the longest.

🔑

What could you start that you could keep doing for decades?

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“Plans are only good intentions unless they immediately degenerate into hard work.”

Peter Drucker

I’ve lost more chess games to the clock than to bad moves.

Each player gets 3 minutes in a game of blitz chess. I used to find good moves and run out of time hunting for better ones.

Hundreds of losses taught me to play good moves instead of waiting for perfect ones.

Last week I sat down for two and a half hours of deep work and spent all of it ranking my to-do list.

The time block ran out before I started the top item. Some items on my list were still unranked.

Planning felt productive.

This was before I separated planning from execution.

What you work on counts far more than how hard you work. Out of a hundred things on a list, the top one can outweigh the rest of the list combined.

Finding it takes real work.

People credit Abraham Lincoln with a saying in defense of preparing first.

Give me six hours to chop down a tree and I’ll spend the first four sharpening the axe.

Sam Hinkie spent three seasons building an NBA team to win later. He took over the Philadelphia 76ers in 2013 and collected draft picks and young players while the team lost.

In 2014 he drafted Joel Embiid. Injuries kept Embiid off the court for the next two seasons.

Hinkie’s teams won 47 games in those three seasons.

In April 2016 the owners moved to hire Bryan Colangelo to run basketball decisions. Hinkie resigned instead.

His resignation letter made the same case: “In the short term, investing in that sort of innovation often doesn’t look like much progress, if any.”

In 2018 Embiid led the 76ers to 52 wins and the playoffs.

Yaron Weitzman tells the story in Tanking to the Top.

Since planning is valuable, I give it a short session before deep work.

Deep work is only for doing, so planning can’t pass for progress.

🪓

What’s the top item you could start before ranking the rest?

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“The years teach much which the days never know.”

Ralph Waldo Emerson

Each day I open a board with my business numbers and ask one question of each: am I above or below my 30-day median?

Above it, I’m doing better than usual.

Numbers jump around, often for reasons that have little to do with what we did. These swings are part of running a business.

What I want to know is whether I’m moving in the right direction.

A programmer named John Walker tells a version of this in The Hacker’s Diet. In January 1988 he set out to go from 215 pounds to 145.

Along the way his weight swung by several pounds from one day to the next, mostly from water. A good week could still end on a higher number.

He called the bathroom scale “a modern instrument of psychological torture, an engine of confusion and despair.”

John started plotting a moving average instead. Each morning’s weight nudged the line a little. He judged his progress by the average.

By November he weighed 145.

A good day can hide a bad month. A bad day can hide a good one.

🔥

What goal could you judge by the month instead of a day?

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“A single conversation across the table with a wise man is better than ten years’ mere study of books.”

Chinese proverb

I learn more from 10 minutes of a podcast than from an hour with most books.

So why would two people talking teach me more than a book someone spent years writing?

Dale Carnegie tested his advice on a classroom before he wrote it down. He taught public speaking at night to people in business. His students needed more than speaking lessons, so he searched for a textbook on getting along with people.

He came up empty and wrote a short talk instead.

Each season he gave the talk and sent the class out to test it. A week later they reported back.

The rules started on a card the size of a postcard, then grew into a leaflet and a series of booklets. Years later, the booklets became How to Win Friends and Influence People.

The book has sold more than 30 million copies.

Yuval Noah Harari’s Sapiens also began as lectures to his history students.

The comedian Jerry Seinfeld tests each joke on a crowd before he keeps it. After his sitcom ended, he retired his old jokes in an HBO special. Then he built a new act from nothing.

He’d show up unannounced at basement comedy clubs and try new jokes one at a time. The documentary Comedian filmed it.

It took him more than a year to build a full hour.

Alone with a page, you can spend an hour trying to sound smart. Across from a listener, you aim to be understood.

🎙️

What could you explain to a friend before writing it?

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“If society can train you, it can train someone else, and replace you.”

Naval Ravikant

Last week I took a 2-hour walk and kept asking myself one question.

What becomes valuable as AI does more of our work?

In February 1968 New York’s sanitation workers wanted a raise of a few hundred dollars a year, so they walked off the job.

The year before, the state passed a law that banned public workers from striking. Their union leader John DeLury led the strike anyway.

About 100,000 tons of garbage piled up on the city’s streets.

A judge sent DeLury to jail. Vincent J. Cannato tells the story in his book The Ungovernable City.

Plenty of other people could learn to drive a garbage truck. But with all the drivers out at once, the city had no one to replace them.

The workers got their raise.

Dockworkers on the East and Gulf Coasts did the same in 2024. They shut the ports for a few days and won a 62% raise over six years.

Holding out together made common work scarce.

A typical nursing assistant in the US earns about $42,000 a year.

An anesthesiologist earns more than $350,000.

Both keep patients alive. Many people can learn to help a patient wash and eat. Few can be trusted to keep a patient unconscious through surgery and wake them up safely afterwards, so hospitals compete to hire anesthesiologists.

You could work harder than anyone on the ward as a nursing assistant and still earn a fraction of an anesthesiologist’s pay.

Companies get paid the same way. Only one company makes the most advanced chip-printing machines: ASML.

In 2025, it kept about 29 cents of profit from each dollar of sales.

Kroger shoppers can buy the same groceries at other stores across the street. The grocery chain keeps less than 2 cents of each dollar.

People and companies earn the most for work many people want done and few can do.

💎

What could you offer that isn’t available anywhere else?

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“Should you find yourself in a chronically leaking boat, energy devoted to changing vessels is likely to be more productive than energy devoted to patching leaks.”

Warren Buffett

A few months ago I wrote about luck versus hard work.

Your position can matter more than both.

In 1994 TLC released CrazySexyCool. It sold over 10 million copies.

T-Boz, Left Eye and Chilli sang the songs, starred in the videos and performed the album on tour.

Their manager, Pebbles, ran a company called Pebbitone. TLC signed their record deal with her company. Pebbitone held the contract with LaFace Records.

Since the cost of studios, videos and tours came out of TLC’s royalties first, little of the album money reached the three women.

TLC got about 20 cents for each album sold, split three ways. Out of an estimated $175 million in album sales, their share was about 1%. That’s roughly $1.75 million.

In July 1995 all three women filed for bankruptcy, with about $3.5 million in debt.

“We’re as broke as broke can be,” Chilli said the next year.

The three women behind an album that sold over 10 million copies ended up in debt.

Alexey Pajitnov built Tetris as a worker at the Soviet Academy of Sciences.

Because he was a state employee, the game belonged to the state.

A Soviet agency called Elorg licensed it to companies in the West. Nintendo bundled it with the Game Boy.

By 1992 Nintendo sold about 7.5 million copies in the United States alone.

Pajitnov earned nothing from those sales. The rights came back to him in the mid-1990s. Only then did he earn his first royalties, about 12 years after he built the game.

Dan Ackerman tells the story in his book The Tetris Effect.

Pajitnov did the work. Elorg collected the license fees.

Hard work from a weak position carries the most risk and keeps the least return.

♟️

How could you put yourself in a position to earn more?