Curiosity Chronicle

In 2021, I left my traditional career track in finance to go all in on writing and creative work.

I assumed that more time inputs would mean more, and better, outputs.

I was wrong.

The writing, once a highlight of my day, had taken on the feel of a job. The passion had become work.

As it turns out, there's real science that helps explain why. It's called the Overjustification Effect: When an expected external incentive decreases a person's intrinsic motivation to engage in an activity they already enjoy.

In this piece, I wrote about how I learned to protect the things I love from the weight of expectations and why I think you need to become a beginner again.

It's a small rebellion in a world that wants you to do everything with some purpose in mind.

You don't have to get good at every single thing you do. You don't need to attach metrics to every pursuit. Not everything has to become something.

Some things can just be.

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

I'm often asked for advice from people just starting out in life.

When I respond, I imagine I'm speaking to my 22-year-old self. Young. Energetic. Highly ambitious. But with little direction. Feeling lost.

There are a handful of things I find myself consistently repeating in these responses, so I thought it would be worthwhile to collect them into a single piece.

But to be clear, in writing (and re-reading it), it's obvious to me that this advice applies to all of us. At any age. On any life path.

So, strap in and buckle up.

Here's my brutally honest advice to my 22-year-old self...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

In an apocryphal story, legendary painter Pablo Picasso was walking through the market when a woman approached him and asked for a drawing.

Picasso quickly drew a small, but beautiful piece of art and handed it back to her.

"That'll be one million dollars," he smiled.

"But Mr. Picasso, it only took you thirty seconds!"

"On the contrary," he replied. "It took me thirty years to draw that masterpiece in thirty seconds."

This story is a perfect example of a modern crisis I'm starting to see in the AI era.

It's called the Locksmith Paradox: We have a tendency to undervalue something because of the low visible input required to create it, despite the output being exactly what we requested.

In this piece, I talk about the science behind this phenomenon, why it penalizes efficiency and rewards general incompetence, and how to fight back as individuals, leaders, and organizations...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

A six week stretch of travel had already reduced my output. Then, I got caught in an earthquake in Panama. And finally, upon returning home on little sleep, I was laid out by a bug my son brought home from school.

This weekend, as I started to think about the week ahead, I noticed a familiar, building sensation. A clenching tension in my jaw and neck. A heavy drop in my shoulders. An elevated heart rate.

It got me thinking about how to find your way out of the land of overwhelm when the pile of work and life debt feels too heavy to even start on.

The body and the mind are intimately connected. Every random object is effectively an open loop. I build momentum on the small and then leverage that momentum to knock out the big.

In this piece, I talk about my five-step Overwhelm Protocol: move the body, clean your room, make a Weekly Win Card, create a snowball, and knock down a wall...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

Last Wednesday, I flew to Panama to deliver two keynotes. I was excited for the trip. I’d been once before as a kid and remembered the beautiful country.

I completed the first talk on Thursday evening and the second on Friday morning. I left feeling energized and headed back to the hotel to take a few calls before heading to the airport.

At 12:56pm local time, I was on the top floor of my hotel when I started to feel a light rumbling sensation in my chair.

But then, chaos. The floor started to shake. The entire building started to sway. Things started falling off the counters and onto the floor.

I would shortly find out that a 7.7 magnitude earthquake was underway. Over the next 30 hours as I tried to find my way home, there were 161 aftershocks, including several 6.0+ magnitude tremors.

In this piece, I share my stream-of-consciousness perspectives from going through a massive earthquake.

How everything got smaller. How I was reminded that shared struggle builds bonds. Why awareness is so very perishable.

And why bad luck may not be so bad...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

Confession: I’ve never been someone who was a natural in social settings.

As something of an introvert, I struggled to build new adult relationships. I often felt others weren’t responding to my social signals. In most cases, I just assumed they didn’t like me and moved on.

But it turns out I was actually falling victim to a damning collision of two psychological phenomena:

• Signal Amplification Bias: Our fear of rejection in social situations tempers our ability to convey social signals, and blinds our ability to recognize that tempering effect.
• The Liking Gap: We assume others like us less than they actually do.

In effect, you send less than you think, and you hear less than they send.

Two people who like each other leave an interaction convinced the other one doesn’t.

In this piece, I share a simple solution that has completely transformed my experience with adult friendships:

Like people out loud...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

When I was 13 years old, a single story changed the course of my life.

But to understand it, I need to take you back in time to a strange experiment from decades ago.

Neuroscientist Michael Gazzaniga was studying patients who had their corpus callosum surgically severed. His experiments led him to hypothesize that the left hemisphere has a specialized system he called The Interpreter, whose responsibility is to find clear cause and effect.

Its job is simple: To take scattered, seemingly random data and facts about the world in front of you and stitch them into a coherent story that feels true.

The problem is that we’d rather have a story that’s wrong than no story at all.

For me, The Interpreter began telling a story when I was young: I wasn’t very smart. My sister was the smart one. I had to be something else.

And then, confirmation bias kicked in. The story determined what “counted” as evidence. Eventually, the story itself constrained my world.

In this piece, I talk about the stories we tell ourselves and the empowering truth that allowed me to confront my own:

You wrote the stories. Which means you can rewrite them.

The most important story in life is the one you tell yourself.

Make sure it’s true.

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

Confession: I'm a routine guy.

I thrive on structure. I think of routines as a way to ensure execution against the daily action that contributes to long-term, compounding progress.

But there's a dark side to routines that nobody talks about.

When your routines become too rigid and complicated, they become a source of stress rather than strength. The routines meant to serve you can start to own you.

This is where my 90-10 Rule comes in:

90% disciplined compliance.
10% open flexibility.

90% of the time, I'm locked in with my structure, but 10% of the time, I give myself the space to let life happen freely.

In this piece, I talk about the Paradox of Routine: The best routine is the one you can break.

The 10% is what enables the 90% to be so effective.

Your routine should serve your life, not own it.

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

In the 3rd century BCE, King Pyrrhus was preparing for an aggressive military campaign in Italy when a trusted advisor named Cineas asked him a simple question:

After conquering Italy, what would they do next? Then Sicily. Then Libya and Carthage. And then?

King Pyrrhus replied, "Then we will live a life of ease. Drink all day and have pleasant conversation with our friends."

Cineas paused and spoke: "But what's stopping us from doing that today?"

The story is one of the oldest documented cases of the Arrival Fallacy: the false assumption that reaching some achievement or goal will create durable feelings of satisfaction and contentment in our lives.

But life is rarely so black and white. Ambition isn't the mortal enemy. And presence isn't the perfect hero.

In this piece, I wrote about choosing the middle path. Rejecting the or and embracing the and.

Remember: You can conquer your Carthage if you want to. Just don't make the wine wait for it.

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

AI is quite clearly the biggest buzzword of the year.

But one thing I don't see anyone talking about is just how much AI is shifting how rewards are earned.

Things are changing so rapidly that the frontier of accurate prediction has been pulled closer and closer to the present.

In this new world, the rewards will be earned by those who are willing to be beginners over and over again. The value seems likely to accrue to those who can combine curiosity and a beginner's mindset with bias for action.

This means that learning has become a core meta-skill. Perhaps even THE core meta-skill.

On Friday, I wrote about the Protégé Effect: the psychological phenomenon where teaching, preparing to teach, or pretending to teach information to someone else helps you learn and retain that information better yourself.

The new world will place an emphasis on adaptation. Rapid iteration. Learning and unlearning.

It sounds scary. It shouldn't.

If you're willing to be a beginner again, the future is brighter than ever...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

Last week I wrote about failing a marathon.

Six days later, at 5am, I drove back to the course alone and ran 26.25 miles in 2:48:47. Not because I needed the official result. Because when I say I'm going to do something, I do it.

In this piece, I talk about seven lessons from that solo marathon that have nothing to do with running — how to stack slow progress, how to stay in the long game, and why showing up through the valley is the whole game...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

In 1865, English economist William Stanley Jevons studied the impact of the increased efficiency of coal use.

The common economic intuition said that as efficiency improved, people would use less coal. Jevons argued that the economic reality was different: As technology improved the efficiency of coal use, demand for coal would increase as people created and justified new uses.

It became known as Jevons Paradox: technological improvements that increase the efficiency of a given resource lead to a rise in the consumption of that resource.

I think the most interesting application of Jevons Paradox is in your life.

When you optimize for efficiency, you may find yourself doing more, not less, of the thing you tried to become more efficient at.

In this piece, I share a simple reminder:

Efficiency is great. But only when it gets you more of what you actually want...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

Last Sunday, I was scheduled to run a marathon with a goal of completing the race in 2:49:59.

I trained all summer for the race, building up to 70+ mile weeks. I tapered. I carb loaded. I meticulously prepared for every detail.

And honestly, I was certain I’d do it.

But…I failed.

After 21.45 miles at a 6:24 average pace, I stopped and walked off the course. I didn’t finish. DNF.

That’s not something you read in newsletters or see on social media every day. It’s all about wins. Successes. Achievements.

On Wednesday, I wrote about why failure is a good thing. It means you had the courage to go all-in. To try. To do something. To step into the arena.

You may not always get it done. But you’ll win at life along the way...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

The engineer took out an axe and slammed it into the brick wall.

It was June 1896. The young man had spent months working in a small brick shed behind his rented house, only to realize, at 4am, that the door wasn't big enough for what he'd built.

His name was Henry Ford. His creation, the Ford Quadricycle.

His atomic insight was simple: He began viewing the factory itself as the product.

While others obsessed over the car, he obsessed over the factory. By the early 1920s, Ford owned an extraordinary 60% of the U.S. automobile market.

But around 1921, the ground began to shift. And while Ford was destroying new prototypes and rejecting changes, Alfred Sloan was building General Motors with adaptation as its core principle.

Sloan had a different atomic insight: He began viewing the company itself as the product. Under Sloan's management, while Ford sputtered, GM's market share doubled, from around 10% at the start of the decade to around 20% by 1925.

The lesson isn't Don't be a Ford or Be a Sloan. Rather, it's Be a Ford, then a Sloan.

In this piece, I explored why the skill set that gets you to your first million isn't the same as the one that gets you from one to ten. And why, above all, adaptability is the key to life...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

Last weekend, my family and I made our annual pilgrimage to a small community in northwest Connecticut.

When I was 18 months old, my parents had rented a house there for the summer, seeking an escape from the New York City heat.

The next year, we went back. The following, we went again.

Soon, the tiny enclave became like a second home. I met my two best friends there. I caught my first fish there. I had my first crush there.

But perhaps most importantly, I played my first game of catch there.

As I remember it, I was probably about five years old. My dad had a softball and a couple of old baseball gloves. And there, in the tall, overgrown grass, we threw the ball back and forth.

We played catch damn near every single day when I was a kid.

But then, as I got older, my baseball career ended. And with it, our game of catch.

Time goes unnoticed, until it's the only thing you notice.

In this piece, I shared what happened last Sunday when I unlocked one of the old cabinets, pulled out two gloves, and asked my dad if he wanted to have a catch...

It was just a game of catch. But it was so much more...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

I first met Tim Cook in 2014.

I was just starting my career in finance and had signed up for a local gym that opened at 5:00am. I started arriving at 4:45am so I could get to the office by 6:30.

Each morning, there was a small handful of others who would congregate outside the doors at that time. Tim happened to be one of the people in that group.

For the first six months, I talked to him almost every day and had exactly zero idea who he was.

As our friendship grew and I came to consider him a mentor, I realized something deeper was going on. A few years later, he was still there. Doing the exact same thing. Every single day.

He became the best example I've seen of an old Zen saying:

What do you do before enlightenment? Chop wood, carry water. What do you do after enlightenment? Chop wood, carry water.

In this piece, I talk about the lesson I learned from seeing it up close: The outcomes may change. The titles may change. The scale may change. But the work doesn't...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

I'm convinced that the market for telling people what they want to hear is much larger than the market for telling people what they need to hear.

That one fact explains a lot of what you see in the world.

But my goal has always been to be real. Even if it's unpopular. Because everything I write is something I hope my son reads someday, and I owe him the truth.

Today, that truth is a few things nobody told you about success.

It may not be what you want to hear. But it's definitely what you need to hear...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

Imagine two different people on the same mid-January day.

One lives in California. He walks outside in shorts and a t-shirt. The warm sun beams down on his face. He puts on his sunglasses, unlocks his car, and turns the AC on full blast.

One lives in New York. He walks outside in a heavy jacket. He grimaces as the cold wind hits his uncovered face. He opens the trunk of his car, takes out a brush, and starts cleaning the snow and ice off his windshield.

Which one do you assume is happier?

You just picked one in your mind. And I probably would have picked the same. Right up until I lived both.

Yes, the truth is, the two people are both me, just one year apart.

And our assumptions about their relative happiness reveal an important cognitive trap everyone needs to understand.

It's called the focusing illusion.

A cognitive bias where people overemphasize the importance of a specific, visible factor when estimating the overall happiness of an individual or group.

In this piece, I explored why what you can see is almost never what matters, and shared a simple question I like to call my Tuesday Test...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

A few weeks ago, I came across a podcast clip of Conan O'Brien talking about why he doesn't pay to fly private. He likes going through the airport, chatting with people at TSA, and "being in the world with other people that are traveling."

It got me thinking about the obsessive pursuit of convenience and the hidden debt it creates in your life.

Money has the ability to reduce the simple stresses, burdens, and inconveniences of adult life. But there's a certain level of inconvenience that's an important part of the human experience.

When you seek convenience, you get a benefit now in the form of ease, but it creates a corresponding liability in the form of reality separation.

In this piece, I talk about the hidden debt of convenience, how to pay it down by embracing friction, and why friction is what makes your life feel real...

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.

In 1628, Sweden's mightiest warship sank less than a mile into its maiden voyage -- not because of an enemy attack, but because a king couldn't stop adding to it. I call it the Vasa Effect: the addition of individual positives can eventually create a catastrophic negative.

In this week's piece, I break down why our bias for addition is holding us back and how creative subtraction might be the fastest way to improve.

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This episode brought to you by:

• DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online.
• Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
• Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
• Lemon - The Al agent that turns your voice instructions into finished tasks.