​read time 11 minutes

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The 4 Types of Professional Time

A few years ago, I noticed a struggle in my professional life:

I’d end the day drained, but when I looked back, I was unable to point to a single thing that I’d meaningfully moved forward.

I started convincing myself that I wasn’t working enough. I needed to work harder. Do more. Grind.

But that got me nowhere, because it turns out, it was entirely wrong.

The problem wasn’t how much I was working. It was the type of work that filled the day.

To solve that problem, I created a simple model that changed the way I work:

Deconstructing Professional Time

I believe there are four types of professional time:

1. Management

2. Creation

3. Consumption

4. Ideation

I’ll walk through each to explain it more clearly.

1. Management Time

Most people spend the majority of their professional lives here.

Typical activities include:

• Meetings

• Calls

• Presentations

• Email processing

• Team and people management

• General coordination

It looks (and feels) like productivity. And it matters, because things tend to fall apart without it.

But it also has a tendency to expand and consume all of your time. Bleeding into every open space on your calendar.

Management Time can quietly shift from real productivity into performative productivity. A focus on movement over progress.

2. Creation Time

The second most common type of professional time. It’s usually what you scramble to jam into the gaps between Management Time blocks.

Typical activities include:

• Writing

• Coding

• Building

• Designing

• Analyzing

This is where real progress is unlocked, but it’s usually the first thing that gets crowded out, relegated to the thin windows that remain after Management Time.

3. Consumption Time

The first of two forgotten types of professional time. It’s often forgotten because it’s about input, not output, so it’s easy to cut when the calendar gets tight.

Typical activities include:

• Reading

• Listening

• Studying

The things you create are a natural byproduct of the things you consume.

Your consumption “diet” establishes your creation capacity. Garbage in, garbage out. Quality in, quality out.

4. Ideation Time

“All of humanity’s problems stem from man’s inability to sit quietly in a room alone.” - Blaise Pascal

Ideation is the second of two forgotten types of professional time. It’s often forgotten because it has no input and no output. It’s just thinking.

Typical activities include:

• Brainstorming

• Journaling

• Walking

• Reflecting

Most of us have zero room for stillness in our working lives. We’re too busy producing to think.

The hard work may create linear progress, but non-linear outcomes are a result of slowing down. The non-obvious idea, the better question, the a-ha moment. All of the 10x opportunities sit on the other side of the stillness you’re avoiding.

Establishing Your Baseline

Before you can improve your balance of professional time, you need to understand your starting point.

Here’s the simple exercise I built to map my own:

For one week, at the end of each day, color-code every block on your calendar according to its dominant type:

• Management: Red

• Creation: Green

• Consumption: Blue

• Ideation: Yellow

An example illustrative calendar might look like this:

At the end of the week, step back and look at the big picture:

• What color dominates your calendar?

• Are there any real windows for Creation?

• What about for Consumption or Ideation?

• Is there a clear rhythm to the days or is it randomly scattered?

Most people are stunned by how much red they see, and by how little space they have for everything else.

With your baseline in hand, here are a few steps to improve it...

3 Steps for an Optimal Balance

Step 1: Batch Management Time

Parkinson’s Law is an idea that work expands to fill the time allotted for its completion.

It was first proposed by British naval historian Cyril Northcote Parkinson in a satirical essay in The Economist in 1955.

While originally intended as a humorous critique of bureaucratic inefficiency, the principle rings true:

• Have all day to process email, you end up emailing for the entire day. Have 30 minutes to process email, you crank through your entire inbox in a flash.

• Have months to complete an assignment, you procrastinate and it takes months. Have two days to complete an assignment, you work efficiently and get it done.

Management Time is a clear Parkinson’s Law risk. It has a tendency to bleed out and dominate your days.

But that same risk can become an opportunity: You can leverage Parkinson’s Law to your advantage.

Work towards a “batched” Management Time schedule:

Create discrete blocks of time each day when you’ll handle major Management Time activities, like email, meetings, and general processing.

• 1-3 email processing blocks per day

• 1-3 call and meeting blocks per day

The goal here is to avoid a schedule where Management Time bleeds into every open space on your calendar. We’re trying to keep the Management Time windows as discrete as possible to create space for the other types of time.

So, an illustrative calendar after adding Management Time blocks might look like this:

Note: Your ability to do this will scale with your career progress. If you’re early, small batching wins count; if you’re senior, you can be more ruthless.

Every hour of Management Time you contain will free you up for impactful work that actually moves you forward.

Which is where the next step comes in.

Step 2: Increase Creation Time

You just freed up space by batching Management Time. This is the primary place where that new space is invested.

To do this most effectively, aim to carve out distinct Creation Time windows on your calendar that are aligned to your energy.

The energy point is significant:

Trying to create at the very end of a long, tiring day may not be particularly conducive to robust, thoughtful output. Conversely, carving out Creation Time blocks in the morning or after a short afternoon walk is more likely to spark meaningful results.

Aim to block 1-2 discrete windows per day for Creation Time, ideally during periods when your energy is likely to be high.

Continuing to build on the same illustrative calendar, the addition of Creation Time in the early and mid-afternoon might look like this:

And once you have the block, protect it. No email, no Slack, no “quick checks” on other things. Creation Time is only as powerful as your ability to protect it from Management Time intrusions.

Step 3: Create Space for Consumption & Ideation Time

Both Consumption and Ideation are non-producing time, which means they’re often the hardest to justify when your days get busy.

That said, they’re both essential for generating the consistent, non-linear outcomes we’re all after, so they need to be blocked and protected.

Aim to block one discrete short window per day for each of consumption and ideation.

Adding in our Consumption and Ideation blocks, the complete illustrative calendar looks like this:

Note: This calendar is an idealized version with one short window per day for each of Consumption and Ideation. If that feels impossible, start small by scheduling one short block per week for each.

Now, each day has a balance across the four types of professional time:

• Batched Management Time

• Protected Creation Time

• Short, discrete windows for Consumption and Ideation Time

This is a calendar designed for real progress, not just movement. The goal is meaningful output, not impressive input.

If you feel stuck in your professional life, this model will help. Work through the calendar baseline exercise and three steps.

Identify your current mix of professional time. Then fix it.

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The Goal Gradient Hypothesis

105.5.

That’s how many laps you have to run around the first lane of a regulation outdoor track to cover the 26.2 miles of a marathon.

And, when I arrived at my local high school track last Friday at 4:45am, that was exactly what I planned to do.

I wish I had a thoughtful answer to the obvious “um, why?“ this opener no doubt sparks in your mind.

The truth is that every now and then, I like to remind myself that I’ve still got that edge—that “dog” inside me. That I can take on something intimidating and get it done.

Plus, I talk a lot about discipline, grit, and consistency around here. But my rule is that you can’t talk about it if you’re not going to be about it.

If there’s one thing you can always trust with me, it’s this: If I say something, I’ve got receipts to prove that I live by it.

So, there I was, standing alone on the track, in the pre-dawn darkness, with 105.5 laps to go.

I hadn’t told anyone I was doing it, not even my wife. That was by design. It made it more challenging. No one would know if I quit. Just me against me. A mental and physical battle, just the way I drew it up.

I pressed start on my watch and broke into stride for Lap 1.

If you’ve ever taken on a big, scary, ambitious goal, you know how those first few laps felt.

It’s exciting. You’re bubbling with anticipation at the challenge ahead. Motivated. Energized. Enthusiastic. Fresh.

But by Lap 8, that starting high had worn off and the reality of the undertaking set in.

The inner voice started getting louder:

It’s cold. Why is my heart rate already 160? Am I running too fast? My legs don’t feel great. This is stupid. I shouldn’t do this. What if I get hurt?

I had 97 laps to go. I was nowhere close to the finish. I wasn’t even close to being close to being close to the finish. Just a vast oval expanse of monotony and nothingness ahead.

Fortunately, I’ve researched goal-setting and achievement for many years, and as it turns out, there’s real science behind this dark experience.

In 1932, a psychologist named Clark Hull designed an experiment with a group of rats that he placed in a maze with food at the end.

He noticed something interesting:

The closer they got to the end, the faster they ran.

He called it the Goal Gradient Hypothesis. It says that our effort increases as we get closer to achieving a goal. The incentive of the reward grows stronger as we approach it, so we push harder as we near the finish.

You’ve probably experienced this in your own life. You get a burst of energy as the “finish line” comes into view (whether it’s in a marathon, a big project at work, or anything in between).

That’s the Goal Gradient Hypothesis at work.

But the hypothesis also explains why the vast middle “valley” of these endeavors is so challenging to navigate. Without the reward of the finish in sight, there is a notable absence of motivation and willpower.

This is where I’ve found you can leverage the science to your advantage...

If I were to map my likely motivation during the course of my track marathon, it would look something like this:

That’s a serious problem. With that pattern, it would be very difficult to stay engaged, keep the pace I was hoping to hit, and finish the race.

So, as soon as I felt that Lap 8 valley darkness setting in, I changed the narrative:

I’m two miles in. At Mile 5, I’ve got my first gel. I like that mixed berry one I brought. It has 100mg of caffeine too, so that’ll be a nice boost. I’m looking forward to taking that.

Hitting Mile 5 became my goal. Sure, I still had the distant marathon goal in mind, but Mile 5 was now the focus with the reward.

When I hit Mile 9, the same valley darkness was creeping back in, but again, I reset the focus:

I’m nine miles in. At Mile 13, I’m halfway there. That’s going to feel so good, because then every step is taking me home. It’s just a countdown from there.

Hitting the half marathon mark became my goal. It consumed my attention.

For the final 13 miles, I just kept creating (and reeling in) micro-goals:

At Mile 18, I only had two more miles to get to my final gel. At Mile 21, I only had 20 laps to go, so I focused on getting to 10. At 10 laps to go, the real finish line beckoned and I felt the final surge.

The new map of my actual motivation during the course of my track marathon looked like this:

The point here is simple:

When your mind drifts into the darkness of the enormity of the task ahead, change the narrative. Create a new micro-goal. Something to look forward to. A game within a game.

The mantra I repeat in my head:

Stay plugged in.

Not plugged into the finish 90+ laps away. Because no mind is strong enough to do that.

Stay plugged in to the lap ahead of you. Stay plugged in to this straightaway. Stay plugged in to this breath.

I did.

I finished my track marathon in a final time of 2:56:16. My average pace per mile was 6:42. I didn’t stop. I didn’t change directions. I didn’t take any breaks. It was hard. Mental torture. But I was prepared for it.

Every meaningful goal in life follows the same shape as my track marathon.

The start is exciting. The end has momentum. But the long, unglamorous middle is where the failure occurs.

The business that folds after a few months. The fitness goal that fades by February. The book that falls apart in Chapter 6.

The valley of the middle is where goals go to die. The Goal Gradient Hypothesis teaches us why—and gives us the tool to fight back.

So, the next time you’re staring into the abyss, remember:

Stay plugged in.

​read time 7 minutes

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The ABC Goal System

“Just be consistent.”

By now, you’ve undoubtedly heard this advice countless times. So much so that it may even induce an eye roll or sigh.

Yes, it’s true, consistency is the difference maker. The common thread behind every major success story.

Everyone tells you to be consistent, but no one ever tells you how to be consistent.

And let’s be honest, it’s (much) easier said than done. Life gets chaotic. Motivation fades. Discipline wavers. Consistency breaks.

I’ve personally spent thousands of hours wrestling with this exact problem—and I’ve developed my own ultra-simple approach that works:

I call it my ABC Goal System…

The Origins of the System

The seed of the idea was planted in my head during a conversation with a legendary American marathoner in 2023.

I had just started running and was a few days away from my first marathon. When I asked him for advice, he inquired about my time goals for the race.

I told him I wanted to run a sub-3 hour marathon (an aggressive target for a brand new runner).

His response:

“For a marathon, you need three goals: A, B, and C.”

What he meant, in the context of the marathon:

• A Goal: Your optimal time goal.

• B Goal: Your baseline time goal.

• C Goal: Your downside time goal (for a first timer, just finish).

The idea was simple, but surprisingly powerful:

From the start, you focus on the baseline (the “B Goal”). Run the race to achieve it. Be conservative in your early approach. If you feel strong as the race wears on, start to push towards the optimal (the “A Goal”). If you feel weak and start to slip, just aim to hit the downside (the “C Goal”).

Runners who only have the singular time goal (like me before the advice) are likely to be completely derailed if they start to slip. Once their only goal is out of sight, they have nothing to drive them forward.

The new approach is designed to keep you in the moment—in the fight—no matter what you’re feeling. You always have something to focus on.

I took the advice and it worked, running a 2:57:31 in that first marathon in September 2023.

But soon after the race, I realized that the core principle behind the system applied well-beyond running.

It was a cheat code for maintaining consistency across my days.

Here’s how to use it…

My Cheat Code For Consistency

For every daily system in your life, create three goals:

• A Goal: Your most ambitious, perfect case.

• B Goal: Your middle ground, baseline case.

• C Goal: Your minimum viable level, downside case.

On days when you feel great, you hit your A Goal. On days when you feel ok, you hit your B Goal. On days when you feel bad, you hit your C Goal.

The reason this is so incredibly effective for building consistency is because it circumvents a common struggle of highly ambitious people:

The tendency to allow the optimal to get in the way of the beneficial.

We constantly say things like:

• I don’t have an hour to work out, so I’m just not going to work out.

• I don’t have two hours for deep work, so I’m just going to send a few emails.

• I don’t have an hour to call my friend, so I’m not even going to send a text.

But here’s the truth:

Anything above zero compounds.

Consistency isn’t about perfect daily performances. It’s about showing up, however imperfectly, and getting it done.

A 15-minute walk is infinitely better than sitting on the couch. 15 minutes of deep work is infinitely better than zero. Sending the text is infinitely better than nothing.

Anything above zero compounds.

To illustrate how this works, let’s use the simple example of daily exercise. Say I want to build consistency around an exercise habit, but I’ve been struggling to make it happen.

So, I create three goals:

• A Goal: 60 minutes in the gym.

• B Goal: 30 minutes of movement (gym, bike, walk, etc.)

• C Goal: 15 minute walk.

Note: The C Goal should feel almost embarrassingly easy to achieve. Trust me, that’s the point.

My baseline is always 30 minutes of movement. But if I slept great and feel ready, I hit that A Goal of 60 minutes in the gym. Alternatively, if my kid kept me up all night, I’m a bit under the weather, or I’m traveling, I hit that C Goal of a 15 minute walk.

No matter what, I have a focus—and whether I hit my A, B, or C Goal for the day, I know I’m making forward progress.

It doesn’t have to be optimal for it to be beneficial.

Anything above zero compounds.

And the best part is that you can apply this idea to any area of your life where you’re trying to build consistency and make progress.

In your work, it could look like this:

• A Goal: Two long deep work blocks. Batched calls/email time.

• B Goal: One long deep work block. Batched calls/email time.

• C Goal: One short deep work sprint.

In your romantic relationship, it could look like this:

• A Goal: Long walk or date.

• B Goal: Short walk or present conversation.

• C Goal: One call or FaceTime chat.

In your mental health, it could look like this:

• A Goal: 30 minute technology-free walk.

• B Goal: 15-minute technology-free walk.

• C Goal: 5-minute breathing break.

The ABC Goal System removes any intimidation or guilt in your pursuit of consistency and progress.

The system prevents optimal (A Goal) from getting in the way of beneficial (C Goal) and gives you the flexibility to make progress while allowing grace for the inevitable vagaries of life to enter.

You can hold yourself to the fire when it comes to the act, but give yourself grace when it comes to the amount.

In other words, make sure you do the thing, but don’t worry about how much of the thing you do.

Creating Your ABC Goals

To get started with your ABC Goal System, choose an area of life where you find yourself struggling with consistency.

Establish your ABC Goals. Write them down. Track which goal you hit on a daily basis.

My ABC Goal System is designed to help you show up every single day and build the momentum that comes from doing so.

Stop allowing optimal to get in the way of beneficial.

Remember: Small things become big things. Anything above zero compounds.

​read time 7 minutes

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The Pratfall Effect

In 1966, a University of Texas psychologist named Elliot Aronson ran an experiment to examine the role of imperfection on human connection.

Aronson recruited 48 college students and had them listen to an audio recording of a candidate supposedly auditioning to be on a “College Quiz Bowl” team (a popular TV format at the time).

The recordings were, in fact, staged. The candidate was just an actor working from a script. But the participants believed they were real and that they would be helping evaluate the candidate.

The participants were played one of four recordings:

1. Superior Candidate, No Blunder: Answers 92% of the difficult questions correctly. Sounds impressive. Modestly mentions an impressive resume.

2. Superior Candidate, Blunder: Similarly brilliant performance, but spills a coffee all over himself during the recording and exclaims, “Oh my goodness, I’ve spilled coffee all over my new suit!”

3. Average Candidate, No Blunder: Answers only 30% correctly, modestly mentions average resume.

4. Average Candidate, Blunder: Similarly mediocre performance, but spills coffee all over himself with similar exclamation.

They were then asked to rate the candidates on their overall likability for the quiz bowl team.

The findings were fascinating:

The superior candidate with the coffee blunder was rated the most likable of the four. The average candidate with the coffee blunder was rated the least likable.

The staged blunder had helped the competent person and hurt the mediocre one.

The researchers coined the term Pratfall Effect—theatrical slang for a sudden fall on the buttocks—to characterize a counterintuitive truth:

Competent people become more likable when they reveal small, harmless flaws.

They offered a simple explanation:

“A superior person may be viewed as superhuman and, therefore, distant; a blunder tends to humanize him and, consequently, increases his attractiveness.”

Now, that line was written in 1966, but it feels particularly relevant for the current cultural moment.

I assume I’m not alone in this experience, but my feed and inbox feels increasingly dominated by AI-generated content.

It’s clean. Technically perfect.

It’s also hollow. Like a sort-of grayscale version of perfection. It lacks depth, texture, and humanity.

The “AI slop” of the present moment isn’t riddled with mistakes. It’s actually the opposite. It’s devoid of the mistakes that make it feel real.

For most of human history, polish was the signal of competence. Polished work was how anyone could indicate they were credible. But now, polish is free. Anyone can produce something that appears flawless in mere seconds, even if they don’t have the earned competency behind it.

Accordingly, polish has, in some sense, lost its value as a signal.

The new signal is texture.

Texture is the mark of a human being who actually showed up, sat down, and did the work. The imperfection is your proof of humanity.

But it’s important to remember something here from the study itself:

The Pratfall Effect didn’t work for everyone. The mediocre candidate who spilled the coffee became the least likable of the entire group. The same blunder that humanized the competent candidate had hampered the average one.

The lesson: Competence first, pratfall later.

The company’s successful “ugly ad” works because the product is genuinely valuable. The leader’s admission of an error builds trust because most of their calls have been correct. The writer’s typo creates connection because their work is so powerful.

Imagine a master carpenter creating a beautiful wooden table. He cuts the enormous block from a beautiful tree. Shapes it through meticulous effort. Sands away the knots. But he doesn’t apply a finish. He doesn’t smooth every edge. The natural grain gives the table character. Proof of life.

Your task ahead is no different.

Work hard to earn your competence. Build an irrefutable base of understanding and credibility. Then resist the temptation to smooth every edge.

I try to stick to three core principles:

1. Earn your competence.

You can’t skip the work. Build competence. Create evidence. Through reps. Stacked days over a long period of time. There are no shortcuts here. Quiet progress creates loud results.

2. Don’t sand all the texture away.

Once you’ve earned the competence, allow your humanity to shine through the cracks. Hit send on the unpolished post if it feels right. Turn your phone on and press record without doing five practice takes. Fire off the quick memo to the team at the end of the week. The texture is the way.

3. Never over-engineer a spill.

Fake, engineered coffee spills are easily spotted. People see through them much more often than you think. The whole point is that the humanity is real.

In a future flooded with faux perfection, the rarest, most beautiful thing you can be is human.

A ruthlessly competent, yet perfectly imperfect, you.

Embrace the Pratfall Effect. Every now and then, it’s good to spill the coffee.

​read time 10 minutes

Welcome to The Curiosity Chronicle, a newsletter where I provide actionable ideas to help you build a high-performing, healthy, wealthy life.

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5 Life Learnings From 5 Years of The Curiosity Chronicle

A few days ago, I was reminded by a reader that May 14 was the five year anniversary of my first Curiosity Chronicle newsletter.

Sending that first newsletter, which went out to a few thousand people who had been receiving my tweet threads in email format each week, felt like something of a leap of faith at the time.

Fast forward five years and what started with that tiny leap of faith has compounded into something beautiful.

I began reflecting on what I’ve learned through the five years of writing The Curiosity Chronicle and quickly realized that all of it applies well-beyond the bounds of creative pursuits and into any meaningful endeavor in life.

I hope these life learnings help you turn your tiny leap of faith into something beautiful...

1. Start ugly.

My favorite quote is from the ancient poet Rumi:

“As you start to walk on the way, the way appears.”

It’s a reminder that you can’t plan your way into clarity. You have to act your way into it.

When I sat down to write my first newsletter, I was lost. I was 30 years old, living far from my family, with no idea what I was doing with my life. It’s easy to look back and wind some impressive narrative on how I got from there to here, but that would do a disservice to the lived reality.

There was no strategy. No path. No vision.

But the good news? You don’t need one.

You just need to start.

Because anything beautiful in this world started out ugly. And the only people who create beautiful things are those willing to do the ugly version first.

You won’t be able to see the beautiful version yet. You won’t even know what it could become. You just need to supply enough faith to get started.

Just start. Ugly.

2. Violent consistency is the only path to quality.

I recently came across a story in Art & Fear that I love:

A ceramics teacher split a class into two groups. One would be graded on the quantity of their output, the other would be graded on the quality of their output. On the final day, the first group would have their total output of pots weighed, while the second group would have one pot judged.

When grading day arrived, something fascinating happened:

“The works of highest quality were all produced by the group being graded for quantity. It seems that while the ‘quantity’ group was busily churning out piles of work—and learning from their mistakes—the ‘quality’ group had sat theorizing about perfection, and in the end had little more to show for their efforts than grandiose theories and a pile of dead clay.”

Quantity is a necessary precursor to quality. You cannot create once and hope for it to be perfect. You have to create a lot. Every single day.

I think of it as violent consistency.

In the five years since I started this newsletter, I haven’t missed a single issue. Two sends per week, every single week, for five years. I was violently consistent for a long time—and quality followed that consistency.

It’s not going to be pretty. It’s not going to draw oohs and aahs from the crowd. Because it looks messy in the days. It’s getting out of bed when you don’t want to. It’s sitting down at your desk when you’re tired. It’s pounding your head into a wall one more time. It’s ugly. It’s unimpressive.

But it works.

Quality is a byproduct of quantity.

Violent consistency. That’s the real recipe.

3. Think in decades (even while you act in days).

Here’s the trap nobody warns you about: Violent consistency can quietly betray you.

Daily discipline without long-term direction is dangerous. You get so focused on moving that you stop asking what you’re moving toward. You chase good instead of right. You optimize for the days and forget the decades.

And slowly, without realizing it, you drift away from what you were actually trying to build.

There’s a question I started asking myself early on:

How would you approach what you’re doing right now if you knew you’d be doing it for the next ten years?

The question helps you avoid the short-term traps that plague every endeavor. Chasing trends at the expense of authenticity. Chasing value extraction at the expense of value creation. Chasing monetization at the expense of energy and passion.

Every time I felt myself pulled into the short-term game, I reset my focus to the long-term one.

The question can be applied to every area of life:

How would you approach this relationship if you knew you’d be in it for the next ten years? You certainly wouldn’t approach it as a transaction, with your hand out, looking to extract value.

How would you approach this workout if you knew you’d be training for the next ten years? You certainly wouldn’t push yourself to injury chasing a single session.

How would you approach this work if you knew you’d be doing it for the next ten years? You certainly wouldn’t cut corners to hit an arbitrary quarterly result.

Think long. Act now.

4. Trust is the atomic variable of all meaningful pursuits.

The world wants you to focus on the wrong thing.

When I first started writing, I remember being drawn by the vanity metrics that everyone seems to tout on social media. Views, likes, reshares, etc.

The problem with these metrics is that they are often misaligned with the most important thing:

Trust.

Everything is built on top of trust.

Fifty years ago. trust was centralized. Companies like P&G and Sears, Roebuck & Co had an iron grip on the airwaves. They dominated advertising across radio, television, magazines, and newspapers. They built trust—and commerce was layered on top of that trust.

Now, fast forward to today. Trust is rapidly decentralizing. You can build a trust node through the things you put out into the world—and commerce can be layered on top of that.

Trust is the atomic variable. Without it, you have nothing. With it, the rest takes care of itself.

But trust isn’t built through views, likes, and reshares. It’s built through value. Consistently creating value for people. With authenticity. With real connection. With unscalable actions.

It’s harder to build, but you know it when you see it.

5. The world is permissionless.

I often wonder how many extraordinary people waste their entire lives waiting for permission from some invisible arbiter that doesn’t even exist.

Misery loves those who wait. Those who look around waiting for someone to come tap them in. To give them permission to do the things they want to do.

I spent most of my life waiting for permission. Permission to live differently. Permission to pursue my weird interests. Permission to share things with the world.

But the truth is that we live in an increasingly permissionless world.

In the last 15 months, what started with that single newsletter has become the foundation of a New York Times bestselling book that’s sold 400,000 copies and a natural skincare business that’s reached a multi-million dollar run rate.

I don’t say that to brag. I say it because there’s nothing particularly special about me. Nobody told me I could do that. I just wanted to do it. So, I did it.

Technology has cracked the walls of credentialism.

Opportunity is more freely accessible than ever before. You don’t need a stamp of approval. You just need to create things of value. You just need to go do things.

Your entire life will change when you stop waiting for permission to live the life you want. Good things don’t come to those who wait. Good things come to those who tap themselves in.

The life you want is on the other side of the permission you give yourself to live it.

Five years ago, I hit send on a newsletter that I was almost embarrassed to put my name on.

Today, it’s something I’m proud to call my own.

Wherever you are right now, your five years starts today. If it looks ugly, good. Ugly is fine. Ugly is the whole point.

Allow Rumi’s words to echo in your head (as they echo in mine).

“As you start to walk on the way, the way appears.”

That’s all for now. I’ll see you on the way.

​read time 7 minutes

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The Eject Button Mentality

In 2002, Harvard psychologists Daniel Gilbert and Jane Ebert designed a series of studies to test the role of optionality on happiness and human satisfaction.

In the first study, the students in a Harvard photography class were asked to make prints of their two favorite photos from the semester.

After creating the two prints, they were told to select one that they would get to keep, while the other would be filed in the department archives.

But at this stage, the students were split into two groups:

• The first group was told that the decision was final. Whichever print they selected was their print and they couldn’t change their mind.

• The second group was told that the decision was reversible. They could change their mind and swap prints in the next few days.

In the days that followed, the two groups of students were asked how satisfied they were with their selection, both during the swap window and after it had passed.

The findings were counterintuitive:

The final decision group had significantly higher satisfaction with their choice than the reversible group—and the gap persisted 11+ days later, long after the swap window had expired.

The researchers concluded that the brain functions differently with final decisions versus reversible ones.

After a final decision, your mind goes to work on supporting your decision, surfacing positives on the chosen path and negatives on the rejected one.

They called this a psychological immune system: A mechanism that silently works to maintain your emotional well-being.

But in the case of reversible decisions, the psychological immune system doesn’t seem to activate. Your mind remains alert to the alternatives, surfacing negatives on the chosen path and positives on the rejected one.

The most damning finding came in a follow-up, when the researchers asked the students which condition—final or reversible—they would prefer to be in.

The overwhelming majority chose the reversible path. They wanted the option to change their mind, even though that option was the very thing making them unhappy.

The insight:

We systematically choose the conditions that make us less happy because we mistake optionality for freedom.

This study isn’t just about photographs. It’s about your life. It’s a small, controlled version of a psychological and cultural moment most of us are living through every single day.

In the pre-social media age, your sphere of awareness was small. The partners, jobs, comparison set, and general information you could see was effectively confined to what was within your immediate vicinity.

Now, the devices and apps that consume every hour of your days have shattered the boundaries of that sphere. It’s grown exponentially, with no real natural limit.

The pool of potential partners is everyone on the dating apps. The pool of potential jobs and careers is every posting on LinkedIn. The pool of potential health protocols is infinite. The pool of potential comparisons is everyone on Instagram.

Optionality is at an all-time high, both in terms of quantity and accessibility.

But here’s the twist:

The reversibility baked into every path was sold to us as a feature. It’s actually a bug.

I’ve started calling it the Eject Button Mentality.

Here’s how it works:

Every meaningful thing you take on in life has a honeymoon period. It’s the early window where everything feels easy. Progress comes quickly. You’re in sync. Flow.

You feel it in new romantic relationships, friendships, projects, jobs, health pursuits, literally everything.

But after a little while, the honeymoon inevitably ends.

In your relationships, it might be when that first hard conversation appears. In your work, it might be when the progress slows and the learning curve flattens. In your health, it might be when the effort that felt exciting suddenly feels boring.

And when that happens, in a world where you’ve been wired to focus on optionality, you already have your finger hovering, ready to press the eject button.

Here’s the thing most people miss: The moment the honeymoon ends isn’t a definitive signal that you chose wrong. It’s a signal that the real work, and the real reward, is just getting started.

A few decades ago, that was well understood. But now, the eject button beckons.

The mistake isn’t leaving. The mistake is in misreading the difficulty. Difficulty isn’t a sign you chose wrong. It’s the cost of entry for the thing you want.

Every single thing you want in life is on the other side of something you don’t want to do.

And the cruel twist: Even if you don’t press the eject button, the awareness that you could is enough to poison the staying.

Remember the Harvard study: The simple knowledge that you could swap was enough to lower satisfaction, regardless of which photo you picked.

The danger of the eject button isn’t really about leaving. It’s about never fully arriving in the first place.

Now, this isn’t about gritting your teeth and blindly staying in every bad situation.

Sometimes the right call is to eject. Sometimes the relationship is wrong, the job is toxic, the program is broken.

The rule isn’t “never eject.” The rule is “never eject on a bad day.” Make the decision on a good day, with a clear head, based on the actual situation in front of you, not in the middle of the inevitable post-honeymoon hard patch with your brain primed by optionality to catastrophize on the future.

Learn to recognize the difficulty for what it may be: The cost of entry for the thing you want.

The eject button is meant to save your life when the plane is going down, not to be pressed the second the ride gets a little bit bumpy.

Sit in the uncertainty. Stick around for just a few more beats.

You may just find bright blue skies ahead.

​read time 11 minutes

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The Most Powerful Decision Making Razors

A razor is a rule of thumb that simplifies decision making.

The term comes from philosophy. A principle that let you quickly cut away unlikely explanations or unnecessary steps was called a razor.

Razors aren’t perfect. They’re shortcuts. But used well, they can be the highest-leverage tools you carry through life. In an age of infinite information, razors can help you stop overthinking and start moving.

Here are the most powerful razors I’ve found...

The Newspaper Test

When making a decision, ask yourself whether you’d be comfortable with the decision being published on the front page of your local newspaper.

Would you be happy to have your neighbors, family, friends, and children read about the decision you made?

If not, don’t make it.

The Duck Test

“When someone shows you who they are, believe them the first time.” - Maya Angelou

If it looks like a duck, swims like a duck, and quacks like a duck, it’s probably a duck.

You can determine a lot about a person by observing their habitual actions.

Trust actions over stated intentions.

The Feynman Razor

If you can’t explain it to a 5-year-old, you don’t really understand it.

Complexity and jargon are often used to mask a lack of deep understanding.

If someone uses a lot of either to explain something to you, they probably don’t understand it.

The Pygmalion Razor

When choosing who to spend time with, default to people who have high expectations for you.

The Pygmalion Effect is a behavioral phenomenon that says we rise to the level of expectations that others have for us.

So, if you surround yourself with people who believe you are capable of more, who encourage you to think bigger, you will rise to the level of those expectations.

It will be uncomfortable. That discomfort is the cost of entry for growth.

The Boredom Razor

“All of humanity’s problems stem from man’s inability to sit quietly in a room alone.” ― Blaise Pascal

If you feel stuck on a hard problem, step away and make yourself bored.

Go for a walk without your phone. Drive in silence. Take a shower.

Your most creative breakthroughs come from periods of intense boredom.

The modern world has trained us out of boredom. The person who can sit alone with their thoughts has a permanent edge over the one who can’t.

The Luck Razor

When choosing between two paths, always choose the path that has the larger luck surface area.

Most of what we call “luck” is the macro result of thousands of micro actions. Your daily habits put you in a position where “luck” is more likely to strike.

It’s hard to get lucky watching TV at home. It’s easy to get lucky when you’re creating motion, meeting people, engaging, and learning.

Sahil Note: Luck has been a personal obsession of mine for over a decade. So much so that it’s the topic of my second book with Penguin Random House. Still a ways off, but I’ll have a lot more to say on this one.

Occam’s Razor

When weighing alternative explanations, the one with the fewest necessary assumptions is usually the right one.

Put simply, the simplest explanation is often the best one.

If you have to believe a complex, intertwined series of assumptions in order to reach one specific conclusion, always ask whether there’s a simple alternative that fits.

Simple is beautiful.

The 80-10 Test

Make decisions that both your 80-year-old and 10-year-old self would be proud of.

Your 80-year-old self would have you prioritize the long-term compounding of the actions you take today. Your 10-year-old self would remind you to have a little bit of fun along the way.

The recipe for a productive, joy-filled life.

The Braggers Razor

“The loudest one in the room is the weakest one in the room.” - Denzel Washington, American Gangster

Successful people rarely feel the need to brag about their success.

If someone regularly brags about their income, wealth, or success, it’s fair to assume the reality is a small fraction of what they claim.

Conversely, if someone consistently underplays their success, it’s fair to assume the reality is a multiple of what they claim.

The Thrive Rule

Investor Josh Kushner once wrote, “The goal of life is to be excited to go to work and excited to go home.”

Deceptively simple, but cuts through almost every career and life decision.

Most people optimize one side at the expense of the other. Optimize for both. Refuse the false tradeoff.

The Optimist Razor

Spend more time around optimists.

Pessimists see the closed doors. Optimists see the open doors. And probably kick down a few closed doors along the way.

Pessimists sound smart, optimists get rich.

The Smart Friends Razor

“What the smartest people do on the weekend is what everyone else will do during the week in ten years.” - Chris Dixon

If your smartest friends are all interested in something, it’s worth paying attention to.

If that something seems crazy or weird, it’s worth paying a lot of attention to.

Sahil Note: My personal rule is that when three smart friends bring something up independently, I make a small investment in the area. Just enough to make me pay attention. The asymmetric upside of being early is worth the small cost of being wrong.

The Opinion Razor

“I never allow myself to hold an opinion on anything that I don’t know the other side’s argument better than they do.” - Charlie Munger

Learn to treat opinions as earned, not owed.

It’s perfectly reasonable to have no opinion on something that you haven’t done the work to understand.

Normalize “I don’t know enough to have a view” as a sign of strength, not weakness.

The Regret Minimization Test

“I wanted to project myself forward to age 80 and say, ‘Now I’m looking back on my life. I want to have minimized the number of regrets I have.’” - Jeff Bezos

Your goal is to minimize the number of regrets you have in life.

When faced with a difficult decision, project yourself into the future, look back on the decision, and ask yourself which path minimizes the odds of regret.

Choose accordingly.

Hanlon’s Razor

Never attribute to malice that which can be adequately explained by stupidity.

In assessing someone’s actions, do not assume negative intent if there’s a viable alternative explanation, such as different beliefs, lack of intelligence, incompetence, or ignorance.

Applies to politics, relationships, and general online discourse...

Most people aren’t out to get you. They just aren’t thinking about you at all.

The Room Razor

If you have a choice between entering two rooms, choose the one where you’re more likely to be the dumbest person in the room.

Once you’re in the room, talk less and listen more.

Bad for your ego. Extraordinary for your growth.

Hitchens’ Razor

Anything asserted without evidence can be dismissed without evidence.

The burden of proof is always on the person making the claim. You don’t have to disprove something that lacks evidentiary substance to begin with.

Closely related to Sagan’s Standard (extraordinary claims require extraordinary evidence) and Newton’s Flaming Laser Sword (if something can’t be settled by reasonable experiment or observation, it’s not worth debating).

The New Opportunity Razor

When assessing a new opportunity, ask yourself two questions:

1. Do I like the winning version of this thing?

2. Am I willing to do the losing version of this thing for a long time?

The first question asks whether you actually want the view from the summit. The second question asks whether you’re willing to embrace the mud in order to get there.

The best opportunities for your life pass this test. You’ll love the summit and the mud.

The Tonight Test

If you’re invited to something weeks or months in the future, ask yourself whether you’d want to do it tonight.

Humans are notoriously bad at predicting their future bandwidth. We say yes assuming we’ll have more time later. Then later arrives and we kick ourselves.

If you wouldn’t want to do it tonight, you won’t want to do it in a month.

The Time Test

Time is either invested or spent.

Invested time is put toward things that create value in the future. Experiences. Health. Careers. Relationships. Learning. Mindfulness.

Spent time is put toward things that don’t.

Always seek to maximize your ratio of invested to spent time.

The Bloom Rule

Build a life where you’re energized in the morning and exhausted at night.

Energized in the morning means you’re excited about the things you get to work on and the people you get to work on them with.

Exhausted at night means you gave your all to those things and people.

Your best life is built in that collision.

Those are the most powerful razors I’ve found.

None of them will make a decision for you. But used appropriately, they cut through the noise, so you can stop overthinking and start moving.

And ultimately, that’s the key to this whole game we call life.

​read time 7 minutes

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The Powerful Art of Negative Capability

In 1902, a 19-year-old cadet in an Austrian military academy was silently becoming a bystander in his own life.

Franz Xaver Kappus felt trapped. On the track for a life as a military officer, but unsure if he wanted it in the first place. His heart felt pulled in a very different direction.

To poetry.

When Kappus learned that one of his teachers had taught the famed poet Rainer Maria Rilke when he was a young man attending the same academy, he decided to act. Kappus sent a set of his poems to Rilke, asking for an honest assessment and guidance on his life ahead.

From 1903 to 1908, Rilke wrote a series of ten letters to Kappus, on solitude, love, doubt, and the question of how to live when you don’t yet know who you really are.

Kappus never did publish his own poems, but in 1929, three years after Rilke’s death, he published the letters in a single anthology, Letters to a Young Poet.

In the fourth letter, Rilke wrote this:

“Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps you will then gradually, without noticing it, live along some distant day into the answer.”

When I first read that beautiful passage, it immediately struck me as an echo.

Nearly a century earlier, another poet had given the same advice—also in a letter—and given it a name.

In late December 1817, the 22-year-old English poet John Keats penned a letter to his brothers, George and Tom.

In the letter, Keats wrote:

“Several things dovetailed in my mind, & at once it struck me, what quality went to form a Man of Achievement especially in Literature & which Shakespeare possessed so enormously — I mean Negative Capability, that is when man is capable of being in uncertainties, mysteries, doubts, without any irritable reaching after fact & reason.”

Negative Capability is the unique discipline of embracing, rather than running from, uncertainty, doubt, and mystery.

Both Keats and Rilke understood the immense power of sitting in that state of unknowing.

This idea is of the utmost importance in the modern era.

The future feels more uncertain than ever before. AI is rewriting the rules of work. Previously safe tracks appear ripe for disruption. The conversations on fundamental societal change have subtly shifted from if to when.

But at the same time, our tolerance for that uncertainty has steadily declined. We carry the entire world’s knowledge base in our pockets. Any question can be answered in mere seconds. Any doubt can be checked with a quick command. Any uncertainty can be neutralized.

And the byproduct of that unique combination is dire:

A 2018 meta-analysis of 52 studies found that intolerance of uncertainty has been increasing for decades. The researchers propose that a dependency has formed: The more we reach for certainty through our devices, the less capable we become of living without it.

The reassurance-seeking behavior meant to calm us is exactly what’s silently reinforcing an inability to bear the discomfort of not knowing in the first place.

In short, uncertainty is rising, tolerance for it is declining, and the downstream effects show up in ways we’re only beginning to understand, including, many researchers argue, the rise in anxiety, polarization, and loneliness.

In his wonderful new book, How to Not Know, author Simone Stolzoff breaks down three certainty traps that we all fall into:

• Comfort: The desire to stay where it’s safe.

• Hubris: The belief that we know best.

• Control: The obsession with planning to perfection.

The traps will feel familiar. What’s harder is the work of building your Negative Capability to escape them.

The book offers a how-to guide for doing just that:

“Embracing discomfort allows us to transform anxiety into openness. Admitting what we don’t know transforms hubris into humility. And relinquishing control transforms rigidity into acceptance.”

In my own life, I’ve found that the most useful way to develop this muscle is to keep a few questions close at hand.

Whenever I find myself leaping for certainty, falling into one of the three traps, I ask myself:

• What are you trying to escape by answering this right now? The rush for certainty is often just a rush away from your fear of uncertainty.

• What might arrive if you sat with this for one more day? Sometimes the greatest breakthroughs come from just sitting in the discomfort a little bit longer.

• What would change if you stopped trying to figure this out? You don’t have to figure everything out. Some things aren’t meant to be figured. It’s perfectly reasonable to let things remain a mystery.

With all of these, I try to remind myself of an important truth:

The one who can embrace the most uncertainty is the one who will eventually win.

As author George Saunders once wrote:

“In a world full of people who seem to know everything, passionately, based on little (often slanted) information, where certainty is often mistaken for power, what a relief it is to be in the company of someone confident enough to stay unsure (that is, perpetually curious).”

Love the questions. Grow your Negative Capability.

Be the relief you want to see in the world.

P.S. How to Not Know is a great read. I am enjoying it. I think you will, too.

​read time 7 minutes

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Dear Son - A Letter to My Son on His 4th Birthday

My son turns four years old this week.

And if I’m being honest, I don’t know where the time went.

Everyone says this, and I spent most of my life rolling my eyes at it, but my goodness, it goes by fast. With parenting, perhaps more so than most things in life, the days are very long but the years are painfully short.

Last year, I started a practice of writing him a letter each year on his birthday.

He can’t read them (yet), but my hope is that they serve as something of a compass for his journey. Whether I’m here or gone, I hope that they guide him in the direction of a fulfilling life.

I know I can’t walk the path for him, but maybe I can shine a bit of light to give him confidence along the way.

Here is my open letter to my son on his 4th birthday...

To my dearest son Roman,

Today, I want to tell you three stories about your life.

The first story is about struggle.

You don’t know this, but your mother and I weren’t sure we would be able to have you. We struggled, for two years, to bring you into this world. It was a quiet, lonely, painful period.

It came at a time in my life when I really wasn’t sure what the path looked like.

By early 2021, I had made the decision to leave my investing job so that we could move back east to live closer to our families. I figured I’d be able to get a new job in the industry closer to home. But after a string of rejections and failed interviews, I woke up one morning with a terrible feeling of dread.

I’d made a mistake. I’d taken the leap from a good path, but now, I saw nothing but emptiness before me. Between my career, our move, and our failed attempts to bring a new life into the world, there was so much uncertainty. Just a complete lack of clarity.

In the darkness of that moment, I remembered a lesson from an old baseball coach. When you’d find yourself in a tough spot in a game, he’d always call out a simple saying:

“You’re one pitch away!”

So, I focused on the next pitch. I kept waking up. Showing up. Doing something.

The wall broke through. Clarity came shining through. We made the move to the east coast. I defined a new path.

And most importantly, two weeks after getting into our new home, we found out that your Mama was pregnant with you, our son.

When I reflect on those dark months, I’m grateful for them. Because they taught me that the most meaningful things in life exist on the other side of some painful struggle.

That’s precisely what makes them so meaningful in the end. You know what you had to endure to bring them to life. In our case, quite literally.

Don’t shy away from the struggle. Don’t try to avoid it. Lean into it.

The struggle of the dark amplifies the joy of the light.

The second story is about success.

Most of my life, I measured success the way the world told me to.

Money. Achievement. Status. Fancy things. Whatever.

It was a default definition that was never my own, but I chased it nonetheless. All the while convincing myself that my fulfillment, my feeling of enoughness was on the other side of some thing.

I’d get those things and wonder why I never felt successful.

It all came together during a single moment on my book tour.

My Dad, your grandfather, sat in the front row at all of the events. At one event, he was asked how he felt seeing me up on stage.

His response:

“I’m proud that he’s becoming the man he wants to be.”

The power in those words stopped me in my tracks. Not the man that he wants me to be, but the man that I want to be.

This was the moment I learned a truth:

Real success isn’t being the person someone else thinks you should be. Real success is becoming the person you want to be.

That path is yours. It won’t always be well lit. But you won’t walk it alone.

My father believed in me before I believed in myself. That belief silently gave me permission to become the person I wanted to be. It’s the greatest gift I have ever received—and one I promise I’ll pass down to you.

There’s an old African proverb I love:

“Walk like you have 4,000 ancestors behind you.”

Stand tall, Roman. You have an army at your back.

The last story is about love.

For the first 31 years of my life, I didn’t really know what that word meant. I thought I did. I mean, I loved people. First, my parents and my sister, then my best friends, and eventually, my wife. And I felt loved by them.

But the day you were born, I realized how little I really understood about that word. It was like the love I knew was a black and white movie from the past. And suddenly, an explosion of color entered the frame. Rich. Deep. Textured. Something so pure. So vibrant. So, different.

Holding you for the first time, I had a profound sensation:

I spent the first 31 years of my life trying to find the meaning of all of this.

And now, it was staring right back at me.

But my story about love isn’t about me or my love for you (which you will never have to question). My story about love is about your mother, or Mama to you, who loves you more than anyone else in the entire world.

I first noticed it in the hospital after you were born. The way she would adjust you ever so gently to make sure you were comfortable. I’ve seen it every single day of your life since. It takes many forms. As patience. As energy. As touch. As selflessness. It’s almost imperceptible at times. Abundantly clear at others.

But always, always there.

It was her love for you that taught me about love. What it really means. What it really looks like. In some ways, it gave me permission to give and receive love with that same depth.

So, without you, I would never have known real love.

There is nothing like a mother’s love. It’s a love you may never understand, but one you have a duty to respect.

There may come a time when I’m not here. If that ever happens, I need you to take care of your Mama. I need you to cherish her, just as she cherishes you.

If you keep her close to your heart, you’ll always be ok.

I’ll close with a confession:

I spent most of my 20s thinking I didn’t want kids. I thought it was a distraction.

Well, last month, I was tucking you into bed when you looked at me, with zero hesitation, and said, “Dada, you’re my hero.”

I’m not exaggerating when I say it was the best moment of my life. One I’ll think about until my dying day. Not the books. Not the businesses. Not the investments. That.

I’m glad my definition of success changed. This version is so much better.

I love you, Roman. Happy Birthday.

Your Dada

​read time 6 minutes

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The Styrofoam Cup Theory

”Your mistake was thinking any of this was ever truly yours.” - Friends & Neighbors, Season 1

Last weekend, I had the joy of catching up for a quiet dinner in Omaha with a mentor and friend, Apple CEO Tim Cook.

He recently announced that he would be transitioning out of the CEO role at the company after a 15 year tenure.

When the news first broke of his announcement, several people asked me how I thought he would handle the major life change and identity shift.

My answer was a story from a dinner we shared several years ago—one specific interaction that I’ll never forget.

I had recently seen an article that listed Tim alongside the likes of Kim Kardashian, Justin Bieber, and Leonardo DiCaprio as an “A-List” celebrity.

When I mentioned it to him, he broke into laughter at the comparison.

But I was curious, so I asked how he had managed to maintain such a low ego despite his rapidly growing fame since assuming the role of CEO.

He had gone from a relative unknown taking over for Apple’s legendary founder to a household name widely considered one of the greatest CEOs in the world.

His response:

“Well, all of that, it’s not about me. It’s about the role.”

The wisdom in his answer didn’t hit me until much later.

He had managed to separate his identity from the success and title.

Even in the midst of a historic run, he had the awareness to maintain an identity distinct from the role.

The most common identity trap I’ve observed, after years of spending time with people at every stage of life and success, is the opposite:

The rigid attachment of identity to fleeting, external things.

In some ways, his perspective mirrored the famous Patek Philippe ad campaign:

“You never actually own a Patek Philippe. You merely look after it for the next generation.”

Tim was merely looking after the company for the next generation.

As I shared that perspective at our dinner last weekend, it reminded me of a powerful story from author Simon Sinek in Leaders Eat Last:​

A former Under Secretary of Defense was speaking at a conference and told the audience about his experience attending the same conference in prior years.

In the past, when he was the acting Under Secretary of Defense, he had been flown to the event first class, put up in a nice hotel, shuttled around by drivers, and given coffee in a nice, ceramic cup.

This year, now the former Under Secretary of Defense, he had flown coach, found his own way to the venue, and when he asked for a coffee, was directed to the coffee machine with a styrofoam cup.

The lesson was clear:

“The ceramic cup they gave me last year...it was never meant for me at all. It was meant for the position I held. I deserve a Styrofoam cup...All the perks, all the benefits and advantages you may get for the rank or position you hold, they aren’t meant for you. They are meant for the role you fill. And when you leave your role, which eventually you will, they will give the ceramic cup to the person who replaces you. Because you only ever deserved a Styrofoam cup.”

I’ve come to think of this as the Styrofoam Cup Theory:

Your identity should never be attached to the roles you occupy in the world.

All of the professional titles, bonuses, accolades, and accomplishments are fleeting.

They aren’t truly yours.

They’re here today, gone tomorrow.

And if you allow yourself to be defined by them, you’ll be painfully surprised when they are inevitably taken away from you.

The wisdom is found in maintaining two minds at once:

Embrace the joy and responsibility you’ve earned in the present season. Enjoy the ceramic cup. But never forget that you’re merely looking after it for the next generation.

Because remember: None of this was ever truly yours.

​read time 11 minutes

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How to Be More Magnetic

Over the weekend, I made what has become an annual pilgrimage to Omaha, Nebraska to attend the Berkshire Hathaway Annual Meeting.

The event, which is nominally a business update on Warren Buffett’s famed holding company, has become a staple in my annual calendar, mostly due to the incredible density of deep thinkers who drop into the midwestern city for a short window of time.

Every year, I seem to find myself in a few rooms that set off my imposter syndrome alarm bells.

But one thing I’ve learned:

Good things happen when you put yourself in rooms where you don’t feel like you belong.

The real secret isn’t getting into the rooms, though. It’s what you do once you’re in them.

For many years, I struggled to thrive in those situations. I’d feel my pulse quicken with a mix of fear and social anxiety, shy away from conversations, or try to insert myself too forcefully into others.

To solve my own struggle, I became a student, paying close attention to the people who seemed to move with ease, talk to anyone, and make everyone feel seen.

Interestingly, they weren’t the smartest, wealthiest, or most credentialed in the room. They had something else.

Energy.

In my annual birthday reflection, I wrote about energy:

Energy is the most attractive human trait. Not looks, wealth, or status. Energy. Walk into rooms with genuine enthusiasm, curiosity, and interest. You’ll become a magnet for the highest quality people. Energy is contagious. Spread the kind you’d want to catch.

The idea, which has since gone viral on every major social platform, is an important one, but it’s also prompted a very good question from many readers:

How do you build that trait? How do you become magnetic?

Here’s what I’ve learned:

Default to praise of people who aren’t there.

The way you talk about someone who isn’t in the room is one of the loudest signals about the energy you carry.

An observation about the most impressive, magnetic people I’ve been around:

They never speak badly about people who aren’t there. They never use underhanded or discrediting comments.

They glow about them, or they say nothing.

If everyone is speaking negatively about someone, it’s perfectly reasonable to opt out and say nothing. It shifts the entire power balance of the conversation in your favor. It shows a level of stoic awareness and calm that stands out.

We all silently catalogue how others speak about people who aren’t in the room, because we know that we may be the topic of that conversation as soon as we leave.

Those who default to praise command the room and silently set a standard of safety that everyone else can feed off of.

Be the most interested person in the room.

Everyone tries to be the most interesting person in the room. The most compelling stories. The funniest lines. The most impressive credentials. The most names dropped.

Don’t be everyone.

It backfires. It feels painfully forced. It reads as insecure.

Instead, focus on being interested, not interesting.

Turn outward, not inward. Take a genuine interest in others. Not as a means to an end, but because you actually want to learn about who they are as a person, beneath the surface.

When you open up to people, they can feel it. They reciprocate and open up to you.

So, how do you actually do this?

Be visibly happy to see people. Smile at people. Say “great to see you” as a default introduction (it also avoids making a “nice to meet you” mistake where you’ve already met the person but forgot!).

Ask high-quality questions. What are you most excited about right now? What’s creating the most energy in your life at the moment? What’s lighting you up outside of work? All of these questions invite the other person to talk about something they’re excited about.

Focus on doorknobs, not stoplights. Stoplight questions invite a simple response that cuts off momentum. Doorknobs invite the person to walk through and tell a story. Where did you get married? is a stoplight. How did you choose your wedding location? is the same question, but framed as a doorknob. It creates conversational momentum that you can feed off of.

Ask follow-up questions. Be glowing about what other people are doing. Not fake or disingenuous, but genuinely excited about what they’re excited about. Lighting up for others makes them light up for you.

Being interested is how you become interesting.

Actually listen when people speak.

While this sounds obvious, it’s the rarest thing.

Think about how many times you’ve had these two experiences:

• You’re in a conversation with someone and you can see them glancing around the room. Their eyes are darting around, unfocused, searching for something better to do or someone else to talk to. You start losing confidence in yourself because they clearly aren’t interested in you.

• You’re in a conversation with someone, they’re speaking, and you’re just thinking about your next response. You’re not hearing them, you’re just waiting for them to finish so you can say your next line.

In both of these situations, the listener is exhibiting anti-magnetic behavior.

Inverting them, you unlock the recipe for real listening.

Don’t be a conversational narcissist. When someone else is talking give them the full spotlight of the moment. Really listen to what they’re saying. Hear it. Understand it. Contextualize it.

Never look around the room while the other person is speaking. Look at them. Make them feel like the only person in the room.

In a world full of half-listeners, full attention is the rarest gift you can give.

Don’t complain, ever.

Nobody likes a complainer.

They drain the energy of everyone around them. It’s exhausting spending time around someone who constantly complains about things outside their control.

As a rule:

If it’s within your control, go do something about it. If it’s not, you’re just wasting energy thinking about it.

Complaining gives too much power to the thing. Take back that power.

Give honest, full-hearted compliments.

Easily overlooked and massively underrated.

If you think something nice about someone, tell them. No matter how small or inconsequential.

If I like someone’s jacket, boots, or shirt, I tell them. If I thought they articulated something well, I tell them. If I appreciate something about them, I tell them.

It can feel a bit embarrassing, but that’s ok. Be unapologetic in your appreciation for the people around you.

Almost no one will take offense to a true, well-intentioned compliment grounded in reality.

This should generally stop short of feeling like flattery. Flattery is a fake compliment wielded for an angle. The full-hearted version is grounded in truth and honesty.

And when it comes to deeper admiration: Be specific, not general.

It’s not particularly impactful to tell a CEO that you admire their work as a CEO. They hear that all day. It’s generic.

Mention your appreciation for a niche philanthropic cause they care about. A small personal detail about them. Show care for them as a human, separate from the identity the world knows.

People remember being seen for who they are far longer than being praised for what they do.

Take yourself seriously.

This is a subtle but important lesson from my grandmother:

You can’t expect other people to be drawn to you if you aren’t drawn to yourself.

Do the little things to show up as the best version of yourself. Move your body daily. Eat real foods. Get good sleep. Buy a few outfits that fit. Maintain good hygiene rituals.

None of that needs to be expensive, but not doing it will be.

Stop showing up like it was an accident.

Move slowly and deliberately. Head tall. Use open body language. Never cross your arms in front of you. No more scrambling around with your face down in your phone.

The way the world treats you is a simple reflection of the way you treat yourself. Always carry yourself like your life matters. Because it does.

If you do that, the world will start bending to your reality.

Make people feel remembered.

Dale Carnegie’s How to Win Friends & Influence People made saying people’s names back to them a common strategy.

To be perfectly honest, I’m not a big fan of it.

In my experience, when people do this, it comes across as salesy or over-engineered.

My trick is to repeat a name in my head after someone says it. If I have a notebook, I’ll occasionally jot down a quick note to cement it. I also do my best to log a specific detail next to the name (perhaps something about their interests).

The magic isn’t in the initial moment, but in the next time you see them.

Never brag.

Insecurity is the opposite of magnetism.

There are few things more off-putting than constant bragging in a conversation. It’s transparent and a clear sign of internal discomfort.

It only attracts the wrong kind of people into your circle. Yes-men and women who tell you what you want to hear and quietly chip away at your full potential.

If your credibility markers are a natural byproduct of a story or conversation, that’s great, but you don’t need to recite your resume.

It stands out when someone doesn’t brag, simply because of how rare it feels.

Don’t try to prove yourself. The trying is the tell.

That list is the one I wish I had when I was struggling to find my way through these rooms.

It’s a field guide for anyone to be the most magnetic version of themselves.

And most importantly, none of the items on the list require you to be wildly extroverted, impressive, successful, or attractive.

Anyone can take this list and improve the way they show up in the world.

I hope you found it valuable.

Now, go spread the kind of energy you’d want to catch.

​read time 4 minutes

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The Streetlight Effect: Why Smart People Look In The Wrong Places

A man is crawling on the ground under a streetlight when a passerby approaches.

“What are you doing?” he asks.

“I’m looking for my keys,” replies the man.

“Did you lose them right here?”

“No, but this is where the light is.”

This old story—one of my personal favorites—forms the basis for something called The Streetlight Effect:

It’s the tendency to look where there’s light, rather than where there’s truth.

To measure the things that are easy, rather than the things that are meaningful.

To cling to routines we know, rather than adapt new ones that work.

To ask the questions we can answer, rather than the ones we’re avoiding.

I’ve found it too easy to fall into this trap in my own life.

In my early career years, I obsessed over the number of hours I worked rather than the work that actually mattered.

I’d glamorize long hours and forget that many of them were spent scrolling on the internet, managing a productivity system, or processing emails.

I’d cling to my hours worked as a sign of my importance and value, but ignore the harder questions about the work I was really doing.

It popped up in my early writing and content.

I focused on the easy metrics like subscribers, views, and likes, but ignored the (much) more important, yet difficult to measure things, like trust, audience connection, and authenticity.

It even appeared in my relationships.

After my son was born, I kept measuring myself on whether I was showing up for the rituals we’d built when it was just the two of us. The real question wasn’t whether I was doing the old things; it was whether my wife actually felt seen, supported, and partnered with in this new season of life.

That was harder to look at. So for a while, I didn’t.

Fortunately, I realized the mistakes I was making quickly enough to fix them.

Three questions helped dramatically alter my approach:

1. What are you doing simply because it’s the easy thing to do? So often in life we fall into patterns of what I think of as “bad momentum”—we just continue doing things because it’s the way we’ve always done them. Because it’s easy to keep doing it the same way and avoid digging deeper. This question chips away at that tendency.

2. What actually matters here that you can’t easily see? We are very good at convincing ourselves that the thing that we can see is the thing that really matters. But the truth is often more complicated than that. Sometimes it just takes peeling back the layers a little bit for you to realize that you were ignoring the thing you should have been focusing on all along.

3. If the light moved, would you still be looking in the same place? This brings the metaphor all the way through. If the light shifted, would this current thing still be the thing you were focused on? If not, you’re just the man stumbling around under the streetlight.

The keys may not be where the light shines.

Sometimes you have to be willing to walk through the dark to find them.

Because here’s the truth you rarely want to admit:

The answers you seek are found in the questions you avoid.

​read time 8 minutes

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The High Shoulders Theory

When I was 12 years old, I tried out for a baseball all-star team in our area.

I really wanted to make this team. The tryouts were my first adventure beyond the confines of my small town. An opportunity to see how I stacked up against kids from all around the state.

When the results came out, the coaches called my house.

They were taking 16 players for the team...and I was the 17th on the list.

(Note: I later found out that this is what they say to everyone who doesn’t make the team, but the “just missed” feeling made the sting even worse.)

I was devastated.

It was my first real experience with failure. Something I wanted, worked towards, and came up short. I went into my room, sat on my bed, and cried.

A few minutes later, my dad walked in. He sat down on the bed next to me. After a few minutes of silence, he offered a few words:

“I know you’re upset. I understand. It sucks. But here are the three things the coaches said you needed to work on. Let’s go out every day this summer and work on them. Together.”

And we did.

I’d patiently wait for him to get home from work, holding our gloves, a bucket of balls, and a bat. He took me to the local field damn near every single day that summer. I’m sure there were days when he didn’t want to. When he was exhausted from work or travel, but it never showed.

And I came back the next year a completely different player.

Years later, when I got a scholarship to play baseball at Stanford, I still thought back to that one summer as the turning point.

But it was more than the practice that was the real turning point.

It was what my dad said in those moments as we sat on my bed, with tears streaming down my face—and how he followed through on it every day that followed.

He had two options when he walked into my room and sat next to me.

• Option 1: Tell me the coaches were idiots. I was the best player. They had made a mistake. They didn’t know what they were doing.

• Option 2: Acknowledge the pain. Tell the truth about the opportunity in the failure. And be there to support the work to meet that opportunity.

Honestly, in that moment, I probably wanted Option 1. It would have made me feel better. It would have told me that the world was the problem. That an external thing was to blame. That I was great.

Option 2 was the tough pill to swallow. But also the right one.

What my dad gave me in that room that day—and on the field every day that followed—was a foundational principle that I’ve never been able to forget. One that I’ve come to believe sits at the core of every strong relationship in life.

I call it the High Shoulders Theory…

The Two Pillars of Strong Relationships

I believe that the strongest relationships in life stand on two pillars:

• The first is high expectations. The belief that the other person is capable of excellence. That their potential is only limited by their own views. The willingness to tell the truth about that opportunity and the work required to meet it.

• The second is high support. The ability and willingness to provide the love, support, and engagement to help the other person meet those high expectations.

A lot of relationships fall short of this standard. They hit one pillar, but miss on the other.

You might imagine a 2x2 matrix with expectations on the X-axis (from low to high) and support on the Y-axis (from low to high):

In the bottom-left quadrant, you have low expectations and low support. This is the dead zone. The drift. No one holding a standard. No one walking the path.

In the top-left quadrant, low expectations and high support. These relationships provide comfort, but no growth. They don’t challenge you. They don’t push you. They don’t lift you. You feel loved, but you slowly erode in your belief of your true potential.

In the bottom-right quadrant, high expectations and low support. These relationships may spark short-term growth, but they breed long-term resentment. The pressure builds. It’s the boss who demands more but never shows up in your corner. The parent who pushes but isn’t there in the moment of need. The friend who tells you to take the leap but disappears when you’re in the darkness. You may learn to perform, but you struggle to truly, durably grow.

In the top-right quadrant, you have your most meaningful relationships. Those people who combine high expectations and high support. Someone who tells you the truth about who you could become, and then walks that path alongside you. These are the people who change your life.

The most powerful relationships are almost always in the top-right corner of that top-right quadrant.

The Shoulders of Giants

Sir Isaac Newton famously said:

“If I have seen further than others, it is by standing on the shoulders of giants.”

It’s a beautiful line, but I think it leaves out the part that matters most.

The giants had to bend down. They had to choose to provide energy to lift him.

Their shoulders had to be high enough to see far from, but also be offered with energy and enthusiasm.

That’s the basis of my High Shoulders Theory of relationships:

The people who change your life have high shoulders. They can see the truth of your capability and potential. They believe you’re capable of realizing it. And they’re willing to lift you up onto their shoulders so you can.

High expectations and high support.

That’s exactly what my dad did the night I didn’t make that all-star team. He didn’t lower his shoulders to the level of my disappointment. He didn’t tell me the high heights didn’t matter.

He told me that I was capable of the climb—and then he gifted me with his attention and energy to help complete it.

I think about this constantly now.

It’s easy to drift into the realm of low expectations or low support. It’s easy to tell people only what they want to hear. To create an environment where people are afraid to tell you the truth. To be inconsistent in your presence.

But the strongest, most impactful relationships are built on embracing the challenge of holding the line.

This, to me, is the highest calling in our relationships:

To create an environment of high expectations with those we love and show up to support them to meet (and exceed) those expectations we’ve set.

That’s what a High Shoulders relationship means to me. It’s what I seek in those I surround myself with. And what I strive to be to those I love.

Who are the High Shoulders relationships in your life today?

If you have one, tell them. They are rare. Probably responsible for more of who you are than you realize.

And if you want to be one, the work is simple—even if it isn’t easy.

Stand tall. Bend down. Lift. Repeat.

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The Michelangelo Phenomenon

The most famous sculpture in history was almost never created…

In 1464, the Opera del Duomo—the committee overseeing the cathedral in Florence—commissioned a massive statue to adorn the cathedral’s roofline.

They sourced a single, 17-foot block of marble from the quarries in Carrara, Italy.

A sculptor named Agostino di Duccio began work on the project, but after a short stint, he backed out.

A decade later, in 1476, a second sculptor named Antonio Rossellino was hired, but almost immediately walked away, citing the poor quality of the marble block that had been sourced.

It was brittle, difficult to carve, and structurally flawed—too narrow and tall for a full-sized statue to be created.

And so it was that a 17-foot block of (nearly) untouched marble came to rest in an open courtyard in Florence.

A year passed. Then five. Then ten. Then twenty.

That is, until 1501, a full 37 years since the original commission and 26 years since it had last been touched, when the committee gave the long-rejected slab of marble to a 26-year-old artist, offering him the job and two years to complete it.

His name was Michelangelo.

The sculpture, as you’ve probably now guessed, was David.

The story of how the commission came to him is an interesting one, but it’s the story of how he brought it to life that carries a deep, science-backed lesson I’ve never been able to forget.

Freeing the Angel Within

Michelangelo inherited something of a disaster.

Two separate sculptors had rejected the project. The marble was brittle, narrow, and weathered from the 25 years of exposure to the elements.

But despite all of this, he saw something others had missed. He had a vision for what the big, unhewn block could become.

So, he began chipping away, little by little, to reveal a truth that only he could see.

And on September 8, 1504, that truth was revealed to the world. The colossal statue of David was immediately lauded as a masterpiece.

In a quote widely attributed to Michelangelo, the artist described his process, saying:

“I saw the angel in the marble and carved until I set him free.”

Centuries later, Michelangelo’s process—seeing the ideal form hidden in the raw stone and chipping away to reveal it—inspired a group of psychologists to ask a fascinating question:

What if our deepest relationships work the same way?

In a 1999 paper, appropriately titled Close Partner as Sculptor of the Ideal Self, the psychologists found that when your partner sees you as the person you’re trying to become, they act in ways that support that vision and you actually move closer to that ideal self over time.

They called it the Michelangelo Phenomenon, a reference to the sculptor, who chipped away until he freed the angel within.

In a 2009 follow-up, the researchers further explained the nature of this finding.

Most importantly, they determined that it was not conscious:

Your partner doesn’t sit down and create a personal mandate to help you make this transformation. Rather, they just naturally create conditions that help promote the growth and development you’re focused on.

For example, they don’t say, “I’m going to help make you become a disciplined go-getter.”

Instead, they might do things like:

• Tackle some household duties to protect your morning workout time.

• Pick up an extra shift to encourage you to take the professional leap.

• Treat you like the person you’re becoming rather than the person you’ve been.

This creates a virtuous cycle in the relationship, where both individuals are sculpting each other through supportive actions, not words.

It is perhaps no surprise that the effect can also work in reverse. When a close partner acts indifferently towards your goals and aspirations, creating conditions that are reinforcing of the status quo (or worse), they can sculpt you away from that ideal version of yourself.

They roll their eyes when you mention your business idea. They tell you to be realistic about your ambitious goal. They never sacrifice their own well-being to create space for you to pursue yours.

The chisel cuts both ways, as it were.

The Michelangelo Phenomenon extends beyond romantic partnerships and into any close relationships, with friends, family, or mentors.

The most important realization:

Every single person in your inner circle is a sculptor of your future, whether or not they know it.

Someone is either helping create your ideal self, or pushing you further away from it.

There is no in between.

So, this weekend, I’d love for you to take stock of the closest relationships in your life.

Who are the Michelangelos?

Who sees the truth about your ideal self that nobody else can?

Who creates the conditions that allow you to become that person?

Two sculptors looked at a block of marble and saw something broken. Michelangelo looked at it and saw David.

The people in your life are looking at you right now. What they see matters more than you think.

Find your Michelangelos. Be one to someone else.

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The New Opportunity Razor

A few weeks ago, I had the unique opportunity to attend a small author’s retreat hosted by Atomic Habits author James Clear.

To be honest, it was a bit of a ”pinch-me” moment.

I was in a room with a group of 15 authors I’ve long admired, who had collectively sold tens of millions of books and left an indelible mark on the world with their ideas and insights.

We were each asked to share something that had been working for us, and once I shook off the feeling of imposter syndrome, the thing I decided to share was my framework on opportunity selection.

It sparked a deep dialogue and clearly resonated with the group—so I want to share it with all of you today.

The Two Question Test

In a general sense, I think there are two phases of your professional life:

• Phase 1: The “Yes” Phase. You want to say yes to every opportunity that comes your way. Saying yes exposes you to new things. You learn and grow at an accelerated rate. You figure things out. You try a lot of things until you find your thing.

• Phase 2: The “No” Phase. You want to say no to most things. Once you’ve identified your primary energy creators (your things), saying no allows you to focus your energy and attention on those few things that really matter. It allows you to go deep. To mine the gold.

You know you’ve entered Phase 2 when you have clarity on the few things that genuinely energize you.

The main challenge shifts from finding opportunities to filtering for the right ones that will compound most meaningfully in your life.

But navigating this new terrain requires an entirely different operating system.

So, you can thrive in Phase 1 but suddenly find yourself overwhelmed and stagnant in Phase 2.

A lot of people become patterned to say yes to too many things. They chase every new opportunity and end up stretched thin—an inch deep and a mile wide.

That challenge is further amplified by the fact that opportunity accelerates with success. As you progress in Phase 1, you actually have more opportunities coming your way, and you keep chasing all of them, slowly digging yourself into a deeper hole.

I experienced this struggle painfully in my early 30s.

I spent my 20s saying yes to everything—a successful Phase 1—but even as my view on my primary energy creators developed, I failed in my transition into Phase 2.

I chased after a bunch of shiny objects. Business ideas, media opportunities, networking events, and everything in between. It left me drained and a bit discouraged, as most of the opportunities failed due to the lack of energy that I had to put toward them.

The truth was that I didn’t really care about any of them. I didn’t have true energy for them. I just liked the idea of them.

And if there’s one thing I’ve learned, it’s this:

If you’re half in, you’re actually all out. Even 90% in gets you nowhere. There’s something magical in that last little bit, simply because so few are willing to do it. That’s where you unlock new levels to the game. And it doesn’t take talent, just courage to be all-in.

So, to fix this struggle, I wanted to develop a simple test for deciding when to take on (or pass on) new opportunities.

A “razor” is a rule of thumb that simplifies decision making.

I call this test my New Opportunity Razor…

Here are the two questions to assess any new opportunity:

1. Do I like the winning version of this thing?

2. Am I willing to do the losing version of this thing for a long time?

Let me walk through each one to explain how it works:

1. Do I like the winning version of this thing?

Imagine yourself five years in the future. This new thing you’ve taken on is crushing it. You’re up there with the best at it.

Do you like what that looks like as it relates to your life, time, and energy?

In other words, if you make it to the top, are you going to like the view from the summit?

This is a critical first step, because too often in life we climb a mountain for years, get to the top, and realize that we never really wanted the view in the first place.

If you don’t like the life of the person in the corner office, you may want to think about that before you sacrifice 20 years grinding away to get it (or figure out how you’re going to do it differently, at least).

If the answer is no, stop here and say no to the opportunity.

If the answer is yes, proceed to the second question…

2. Am I willing to do the losing version of this thing for a long time?

To earn anything meaningful in life, it’s going to take a long, long time. Probably much longer than even your most optimistic initial assumptions.

An American computer scientist named Douglas Hofstadter once coined the self-referential adage, Hofstadter’s Law, which states:

“It always takes longer than you expect, even when you take into account Hofstadter’s Law.”

So, knowing this, do you have energy to do the losing, bad, ugly version of this thing for a long time in order to earn the winning version that you like?

You may dive into something because of the appeal of the summit, but you’ll never make it there if you don’t embrace the mud you have to crawl through on the climb.

The people who have reached those summits have one common trait:

They loved the mud. They obsessed over the details. They had real energy for it.

When asked about how he had sustained his high level play for so long, tennis legend Novak Djokovic had a simple response:

“I can carry on playing at this level because I like hitting the tennis ball.”

The summit is the grand slam championships. Standing on center court, holding the trophy high in the air. Everyone likes that version.

But the way you earn it is through thousands upon thousands of hours of hitting the ball. In the cold. In the dark. In the rain. When nobody’s watching. When nobody’s cheering. When nobody cares.

The losing version is the cost of entry for the winning version.

The Summit AND The Mud

The New Opportunity Razor has been a major life cheat code.

I’ve said no to more opportunities in the last year than in the previous five combined. And every no got easier, because the two questions made the answer feel obvious.

As a result, I’m more focused and energized than ever before.

I finally feel like I’m in true flow.

The best opportunities for your life will pass this test. You’ll love the summit and the mud you have to navigate to get there.

When you find those things, go all in. Say no to everything else.

P.S. I’m working on a full piece on all of my favorite decision-making razors. If you’re interested in seeing that, just reply YES to this email!

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The Tinkerer’s Mindset: How to Win More

A group of kindergarteners outperformed the CEOs, lawyers, and MBAs.

The way they did it has a lesson I’ve never been able to forget...

While in college over a decade ago, I watched a TED Talk by a famed designer named Peter Skillman about an experiment he conducted in which groups of participants were given a challenge.

They were asked to build the tallest tower possible with the following items:

• 20 pieces of dry spaghetti

• 1 yard of string

• 1 yard of tape

• 1 marshmallow (which had to end up on top)

There were a variety of groups who went through this challenge:

• CEOs

• Lawyers

• MBA students

• and…Kindergarteners

The results were rather shocking:

Kindergartners outperformed all of them (and by a significant margin).

CEOs came in next, lawyers behind them, and the MBA students in last, often failing to create a structure that could withstand the weight of the marshmallow at the top.

So, the big question is why had this happened?

Well, in a later presentation, Tom Wujec, a friend of Skillman who ran the same experiment in workshops around the world, highlighted the differences in how the various groups approached the problem:

So, normally, most people begin by orienting themselves to the task. They talk about it, they figure out what it’s going to look like, they jockey for power.

Then they spend some time planning, organizing, they sketch and they lay out spaghetti...And then finally, just as they’re running out of time, someone takes out the marshmallow, and then they gingerly put it on top...

What kindergarteners do differently is that they start with the marshmallow, and they build prototypes, successive prototypes...so they have multiple times to fix when they build prototypes along the way...

And with each version, kids get instant feedback about what works and what doesn’t work.

Interestingly, in follow-up experiments, architects and engineers performed similar or better than the kindergartners, which further reinforced the understanding of how quality results are created.

The lesson here is quite simple:

Thinking, planning, strategizing, and organizing often get in the way of doing.

This lesson hits me hard, because honestly, I see a lot of myself in the CEOs, lawyers, and yes, even the MBA students.

For most of my life, I was a big planner. When I’d decide to dive into something new, I’d spend days, weeks, and often months gathering information before I really got started.

I basically assumed life looked like this:

If you buy into that version of reality, you place extraordinary emphasis on the upfront work (before the graph even starts), because you believe the pre-start clarity will have to carry you through.

But it’s a trap. Because while you read, research, and build business plans, you’re just engaged in a dressed up version of procrastination.

As the old saying goes, you can dress up a pig in a tuxedo, but it’s still a pig.

I learned it the hard way:

You can dress up procrastination however you’d like, give it some fancy names, hide behind the illusion of progress, but it’s still procrastination.

The truth is that most things in life actually look like this:

The more things you try, the more clarity you gain.

And importantly, that clarity compounds...fast.

At first, it’ll feel like you’re stuck and going nowhere. Then suddenly, the clarity gains in a day will surpass what you had previously been able to achieve in a month.

Clarity comes gradually, then suddenly—but only if it finds you doing.

I think of it as embracing a Tinkerer’s Mindset. Try stuff. Fail quickly. Learn from each failure. Try more stuff. The cost of failure is much lower than you think. Nobody’s judging you. Nobody cares.

The kindergartners weren’t worried about what other people would think if their tower fell down. They weren’t worried about looking or sounding smarter than anyone else in the room.

They tinkered.

We can all learn from that story:

Tinker more. Win more.

​read time 7 minutes

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The Real Price of Success

My entire life changed when I realized that I would never want to trade lives with the people I read books about.

Allow me to explain with a story about the richest man who ever lived...

In the early 1500s, an enterprising German financier named Jakob Fugger rose to prominence on the European continent.

From humble beginnings as the tenth of eleven children, he had risen through the ranks of his family’s burgeoning trading firm, leveraging a rare combination of a healthy risk appetite and a keen eye for an attractive deal to accumulate immense influence and power.

His dealings went far beyond the boardroom. He financed emperors, bankrolled wars, held a near-monopoly on European copper, and owned silver mines all across the continent. He personally funded the election of the Holy Roman Emperor and was the financial backer behind Ferdinand Magellan’s circumnavigation of the globe.

His loan to Pope Leo X to finance the building of St. Peter’s Basilica unknowingly sparked a ground-shaking chain of events when its repayment required a massive sale of indulgences (a kind of sin-forgiveness ticket) that drew the ire of a man named Martin Luther who would lead the Protestant Reformation.

Jakob Fugger’s money—and, by extension, his influence—dramatically influenced the course of world history.

By the time of his death, he had an estimated fortune equal to $400 billion in today’s money.

His success was extraordinary, and by any objective financial measure, Jakob Fugger won the game, but there’s more to this story than meets the eye.

In his comprehensive book on Fugger, appropriately titled The Richest Man Who Ever Lived, author Greg Steinmetz wrote:

“He had few friends, only business associates. His only child was illegitimate. His nephews, to whom he relinquished his empire, disappointed him. While on his deathbed, with no one at his side other than paid assistants, his wife was with her lover. But he succeeded on his own terms. His objective was neither comfort nor happiness. It was to stack up money until the end.”

His thirst for financial success was absolute. The relentless pursuit enabled him to achieve unprecedented things in that domain.

But whenever I read these stories, I’m always left to wonder:

What was the real price of that success?

List Price vs. Real Price

Our lives are shaped by two factors:

1. The things we want.

2. The price we have to pay to get those things.

But the truth is that most of us spend all of our time on the former and very little on the latter.

We think about all the things we want, but very rarely consider the price to get those things.

In truth, life is a little bit like a superstore.

You walk in and there’s an infinite variety of things in front of you. And just like in a store, every single item has a price tag.

There’s a price to pay for anything you want to achieve in life.

The key difference between life and the superstore is that in life, the price tag can lie.

There’s the List Price you see and the Real Price you don’t:

The List Price is the surface level price you pay for the thing you want. It’s the obvious. The effort, hard work, discipline, and energy required to buy or earn that thing.

The Real Price is beneath the surface. It’s hidden. Indirect. Often paid in the form of tradeoffs, opportunity cost, and regrets. It’s all the things you said no to by saying yes to this one thing.

If there’s one thing I’ve come to understand, it’s this:

A lot of things in life look like a great deal on the List Price, but feel like a ripoff on the Real Price.

A Few Questions To Ask Yourself

So, what do we do with this information?

Well, I can tell you what I’m doing, which is asking better questions about the things I want before I take them on.

The questions are focused on helping me deeply consider the Real Price before I’ve had to pay it.

Here are the questions I’m focusing on (which you can steal):

1. What am I saying no to by saying yes to this?

Every yes carries an invisible no.

That promotion you’re chasing means less time for your health or hobbies. That new business venture means less time for your family or sleep.

It’s easy to name the thing you get; it’s harder to name the thing you’re implicitly giving up.

I was recently offered an interesting opportunity with a meaningful financial reward. It seemed compelling on the surface. But it would have meant saying no to a lot of spring and summer evenings with my son while I was on the road chasing the new opportunity.

The Real Price was more expensive than what I was willing to pay.

2. Are the most painful tradeoffs seasonal or permanent?

Sometimes you may face a painfully high Real Price, but one that’s seasonal, rather than permanent.

In other words, it has an expiration date. You know you’ll have to make a lot of painful tradeoffs, but for a defined window of time.

These seasonal tradeoffs are common in your early career years as you build your professional and financial compounding engine.

It may make sense to take on that challenging new role that’ll necessitate a lot of late nights and travel if there’s a clear end date and a significant benefit to your family and stability.

But beware the trap of seasonal tradeoffs that become permanent when the action itself becomes a part of your identity. Too many people dive into the late nights thinking it’ll be a season, but then find themselves enmeshed in the identity of a person who always works late.

3. Would I trade lives with the person who has the thing I want?

This is the question that brings it all together for me (and comes full circle to the opening line of this piece).

It’s not do I want what they have? It’s would I want their whole life to get it?

Jakob Fugger had $400 billion, was the richest man in the world, but died alone.

That’s the problem with comparison. It’s easy to compare on a single plane but lose sight of the full, three-dimensional picture.

If you wouldn’t want the 3D version, you shouldn’t chase their path towards the 2D one.

The Price You’re Willing to Pay

I spent the first 30 years of my life thinking that I had to build something enormous, be extraordinarily rich or famous, or have some large buildings named after me.

But while the world certainly needs some people to continue thinking like that, as I’ve gotten older, I’ve realized that the Real Price of those things is not one that I’m willing to pay (at least not in this season of my life).

Because I feel the richest when I’m able to take my son to the carousel at 1pm on a Tuesday.

And that’s just not something I’m willing to give up.

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P.S. If you enjoyed this, I wrote a NYT bestselling book that goes deeper on these topics to help you build a life you love. you can order it here!

​read time 6 minutes

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Black Coffee Theory

A few weeks ago, I shared a piece on my Anti-To-Do List and the general merits of using inversion to improve your life.

The idea was straightforward:

1. Write down what you want to avoid doing.

2. Avoid doing those things.

I’ve gotten a lot of value from using inversion like this as a tool to provide clarity on my actions and avoid painful mistakes.

As the late Charlie Munger famously said, “All I want to know is where I’m going to die, so I’ll never go there.”

But a few readers replied with an interesting question:

Doesn’t focusing on what you don’t want make you more likely to get it?

This raises an important point that I’ve never addressed directly:

Inversion is merely a lens in your life toolkit.

You look through it briefly to see the world differently, but then you have to remove it to see the world as it is.

If you leave the negative, inverted lens on for too long, you may fall victim to a science-backed life trap that we all need to avoid...

There’s an idea called Black Coffee Theory that illustrates the trap:

Imagine you walk you into a coffee shop.

When it’s your turn to order, the barista asks you what you want.

“I don’t know. But I definitely don’t want black coffee,” you say.

The barista looks confused, “Ok...but what do you want?”

“I’m not sure. All I know is I just really don’t want black coffee. I can’t stand black coffee. I won’t drink black coffee. Anything but black coffee.”

The barista shrugs, takes your payment, and tells you it’ll be a few minutes.

After handling several other customers, the barista walks over to the drink station to make your coffee, but forgets what you ordered.

“Hmmm, what was it?” they think to themselves. “I remember they kept saying black coffee. Black coffee...that’s right.”

And after five minutes, you’re handed a beautiful, bitter, piping hot cup of exactly what you didn’t want.

Black Coffee Theory says that the world will deliver what you focus your energy towards.

Focus on what you don’t want (the black coffee) and the world will deliver just that. Focus on what you do want (perhaps a cappuccino) and the world will deliver that instead.

It may sound like a mystical manifestation concept, but in fact, this general idea is substantiated by science:

In 1987, a Harvard researcher named Daniel Wegner conducted an experiment where he asked participants to verbalize their stream of consciousness for five minutes, saying whatever came to mind.

One group of participants was told to explicitly avoid thinking about a white bear. They were given a bell to ring each time the thought of a white bear crept into their thoughts.

The result: They rang the bell constantly, unable to avoid the white bear creeping into their consciousness.

In a follow-up, all of the participants were told to actively think about a white bear. Interestingly, the group who had initially suppressed the thoughts of the white bear found themselves thinking about it more often than the group who didn’t.

This effect became known as Ironic Process Theory, which says that the deliberate attempt to suppress a thought may unintentionally amplify it.

The implications of this are significant because your thoughts are the first domino in a chain that quickly cascades into your reality.

The ancient philosopher Lao Tzu captured this well:

“Watch your thoughts, they become your words; watch your words, they become your actions; watch your actions, they become your habits; watch your habits, they become your character; watch your character, it becomes your destiny.”

If you give too much energy to the negative—what you want to avoid—your entire identity can slowly start to become organized around that thing.

Your words, actions, habits, and character become enmeshed in that thing.

And as Lao Tzu pointed out thousands of years ago, your destiny follows.

You say things like...

• “I never want to be broke”

• “I never want to be in another relationship like my last one”

• “I don’t want to end up like my parents”

• “I don’t want to work in a job I hate”

But...

• You don’t have a clear vision of what abundance looks like to you.

• You can’t articulate what an energizing relationship feels like.

• You don’t focus on how you do want to end up.

• You can’t paint a clear picture of a job you love.

A life built entirely around what you don’t want is a life controlled by it.

The antidote is simple (and leverages the science in your favor):

Create a vivid image of what you do want.

• “I never want to be broke” becomes “I want to build a life where money is a tool for creating impact and experiences.”

• “I never want to be in another relationship like my last one” becomes “I want a partner who makes me feel calm, respected, and energized.”

• “I don’t want to end up like my parents” becomes “I want to be the type of parent my kids will want to hang out with when they’re adults.”

• “I don’t want to work in a job I hate” becomes “I want to be excited to go to work on Monday morning.”

When you define what you actually want with clarity, your brain’s monitoring system starts scanning for that. You’ll notice opportunities you previously missed. You’ll meet people you would have glanced by. You’ll make decisions from a position of strength rather than weakness. You’ll operate from a confident footing instead of a fearful one.

Your words, actions, habits, and character will start organizing around the life you want, not the one you’re avoiding.

If you hate black coffee, stop ordering it.

Your thoughts are your order to the universe. Treat them accordingly and you’ll make sure you get the coffee you actually want.

​read time 6 minutes

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Just Make the Coffee

A few years ago, I came across a beautiful story written by a woman named Pam Kearney in a local newspaper.

I set a calendar reminder to re-read this every single year:

I visited Matthew, the owner of Lucy’s Flour Shop a little while back. As I nibbled on an enormous chocolate chip cookie I began to tell him a story.
​
A few years back on a bitterly cold December evening, there was a visitation at the funeral home across the street from his bakery.
​
The people, bundled up in coats, scarves, and blankets were lined up around the building waiting to hug the family of the deceased.
​
Seemingly out of nowhere, a man showed up and began giving away hot coffee to the people outside. People who entered the funeral home with coffee in their hands whispered of a mysterious man handing out free coffee, and how much they appreciated it.
​
I looked at Matthew and said, “I have a suspicion that you were that man. Is that right?”
​
Matthew very humbly replied, “Yes, I felt so bad for them and wanted to do something, but all I could do was make coffee, so I made coffee.”
​
I responded that he blessed so many people that night by helping them warm up and by showing there’s good in the world. He added a positive note to a devastating situation.
​
I paused, then added, “That visitation was for my sixteen-year-old son. Thank you for being so kind.”
​
That conversation has stuck in my head since then:​
​
“All I could do was make coffee, so I made coffee.”

I want you to read that final line again...

“All I could do was make coffee, so I made coffee.”

You can imagine Matthew, standing in his shop, looking out at the line of people standing in the cold on that December evening.

In that moment, I’m sure he felt rather helpless, even paralyzed. He wanted to do something to help, but the imperfection of his options weighed on him.

He couldn’t change the weather. He couldn’t reverse their loss. He couldn’t take away their sadness or suffering.

All he could do was make coffee, so he made coffee.

The Most Important Decision in Life

Every single day, we face our own version of this situation.

Different circumstances, yes, but the same general experience:

We feel stuck. Completely frozen. Not because of the lack of options, but because none of the options are perfect. None of the options feel big enough. None will solve the entire problem or fix the entire issue.

So, most of the time, we do nothing.

But nothing is the one option that’s guaranteed to change nothing.

Since starting this newsletter five years ago, I’ve shared over 500 pieces and 1,000,000 words.

If I could synthesize the lessons down to one single statement, it would be the following:

Do the thing.

Take the action. Just start. Show up. Make the move. Walk the path.

Because the change you want to see doesn’t happen unless you create it. The new life you want doesn’t magically appear. It’s built through action. New habits. New mindsets. New standards. New boundaries.

Action, however imperfect, is always the cost of entry.

I might think of it as the Paradox of Imperfection:

The most perfect outcomes are often just a byproduct of a large volume of imperfect actions.

In the immortal words of Teddy Roosevelt:

“Do what you can, with what you have, where you are.”

As you continue on this crazy adventure we call life, you will face daily moments that conspire to make you feel completely helpless. You’ll feel paralyzed. Unable to see a clear path to create momentum or improve the situation.

In these moments, you have a decision to make:

• You can freeze, paralyzed by the imperfection of your options...or

• You can act. You can do what you can, with what you have, where you are. You can make the coffee.

This is the single most important decision of your life.

Reflect on the moments where you or someone you know “made the coffee” and changed everything.

When my childhood home burned down in 2014, our friends couldn’t rebuild the house, help with the insurance, save the lost items, or do anything to turn back time.

But they showed up: They brought my parents home-cooked meals, bought them fresh underwear, and sat with them for hours.

They made the coffee.

When an old college friend was in a dark place in his life, battling alcohol abuse, our friend group was spread across the country. We couldn’t give him any meaningful advice or stage an intervention.

But we showed up: We organized group FaceTime calls to be with him, to let him know he was loved.

We made the coffee.

When I found myself in a terrible rut in 2021, living far away from my parents, lost and uncertain about the future, I couldn’t snap my fingers and change everything. I couldn’t change my life in a day.

But I showed up: I started writing every morning, following my energy, and opened a conversation with my wife about a move.

I made the coffee.

Making the coffee isn’t just for the moments of turmoil or crisis. It’s for the ordinary Tuesday when you dread getting out of your warm bed. It’s for the business idea that’s been sitting in your head for two years. It’s for the hard conversation you’ve been avoiding. It’s for the workout you want to skip on the day when everything fell into chaos. It’s for the dream that feels too big to begin.

The moments themselves can be big or small, but the lesson is clear:

Action doesn’t have to be perfect for it to be right.

So, the next time you face a situation and start to feel helpless, remember:

Just make the coffee.

​read time 7 minutes

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The Spotlight Effect

For the last decade, I’ve had a recurring nightmare that I can trace back to my days as a Division 1 baseball player at Stanford...

I’m on the mound in a critical situation. All eyes are on me. The entire stadium waits for my pitch.

But as I start my motion, I realize I’ve completely forgotten how to throw the ball. My body moves like it’s stuck in mud. Completely paralyzed.

Inevitably, I wake up in a cold sweat—thankful that it was just a dream.

While specific to my prior endeavors, as it turns out, this type of dream is a rather common one.

In fact, I’d be willing to bet that most of you have experienced some variation of it in the last few months.

All eyes on you in a big moment. And suddenly, you’re completely paralyzed. Unable to perform.

It’s the byproduct of a very common (and damning!) psychological phenomenon—one that has a tangible impact on the way we show up in every area of life.

It’s called The Spotlight Effect...

Nobody Is Thinking About You

The Spotlight Effect is a psychological phenomenon where we dramatically overestimate the degree to which other people are noticing or observing our actions, behaviors, appearance, or outcomes.

The term was coined by a group of researchers in a 2000 paper after conducting a series of now-famous experiments in which they had students walk into a classroom wearing an embarrassing outfit.

The students, forced to don a t-shirt with a huge picture of Barry Manilow on the front, were asked to estimate how many of their classmates noticed their outfit.

The researchers found that the students systematically overestimated the percentage of their classmates who had noticed or recalled their appearance.

They estimated 50%, when in fact, only 25% did.

In a follow-up experiment, students were asked to track their classmates’ appearance changes throughout a semester.

The result: People had dramatically less awareness of changes in others than they assumed others had of them.

The Spotlight Effect basically says that we think everyone else is noticing and judging us, but they aren’t. Even if they are, they quickly forget about it.

The root cause is egocentric bias: Our tendency to see everything through our own “Player 1” lens.

We’re the main character of our own movie, so we assume everyone else is watching it too. But they aren’t, because they’re too busy starring in their own.

Here’s the harsh truth the Spotlight Effect reveals:

You aren’t afraid of failure.

You’re afraid of other people seeing you fail. You’re afraid of what other people will think of you if you fail.

It’s the fear of the judgment. The fear of the embarrassment. The fear of the scrutiny. The fear of the whispers. The fear of the silence. The fear of what they might say or what they might think.

This type of fear has a damning impact on your life:

• You don’t take the leap to start that new business

• You don’t hit send on the content you created

• You shy away from sharing your new ideas in the meeting

• You wait to start until you have the perfect plan

• You don’t tell the story your energy is calling you to tell

• You do the things that will impress others, rather than the things that you actually want to do

Every single one of these things represents a road not taken simply because of the crippling fear of an audience that doesn’t even exist.

I often wonder how many extraordinary people waste their entire lives fearing the judgement of people who were never even thinking about them in the first place. Fearing a spotlight that was never even on.

Here are three ways we can all fight back:

1. Climb The “So What?” Ladder

When you feel the spotlight holding you back, trace the fear all the way to the end.

I call it climbing the “So What?” Ladder:

I might stumble over my words in my presentation.

So what?

People might think I’m unprepared.

But you are prepared. So what?

Well, they might think I’m an imposter.

But you’re credible. So what?

They might not hire me again.

There are more opportunities. So what?​

That’s it. Life goes on. Your family still loves you. You’re fine.

The Stoic philosopher Seneca once wrote, “We suffer more often in imagination than in reality.”

The idea with the “So What?” Ladder is to uncover the fact that the worst case isn’t nearly as bad as we think. If you’ve done the work, if you’ve shown up, you’re ready.

2. Be Interested, Not Interesting

Most people walk into social situations trying to be interesting. Trying to impress with the perfect story, the sharp insight, the right take.

That places a lot of unnecessary pressure on yourself—a sort of self-induced spotlight, if you will.

So, flip it on its head:

Aim to be the most interested person in the room, not the most interesting. Ask questions. Listen. Engage with curiosity rather than performance.

Something remarkable happens when you do so: Your tension dissolves. People open up. You leave interactions with more confidence and energy.

3. Follow The 18-40-60 Rule

There’s a saying I love:

• At 18, you worry about what people think of you.

• At 40, you stop caring what people think of you.

• At 60, you realize nobody was thinking about you at all.

Hint: You don’t have to wait until 60 to learn this lesson. You can learn it right now.

Go Do The Damn Thing

There are two big mistakes in life:

1. Worrying about what other people think about you

2. Believing that other people think about you in the first place

Here’s the truth:

Nobody is thinking about you. Everybody is too busy thinking about themselves.

That thing you’ve always wanted to do?

• That idea you’ve always wanted to pursue

• That story you’ve always wanted to tell

• That person you’ve always wanted to talk to

• That weird hobby you’ve always wanted to try

• That leap of faith you’ve always wanted to take

Go do the damn thing.