Charlie Boluk

I spent 25 years being useful. Then I wasn't. Turns out that's where the interesting questions live.

Executive Life

One Island Learned to Live Together. A Continent Kept Dancing.

Oct 20, 2026

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6 min read

One Island Learned to Live Together. A Continent Kept Dancing.

Malta on one eye, France on the other, and a basketball documentary in between.

Charlie Boluk

Depression

Oct 13, 2026

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6 min read

The Art of Doing NOTHING

& The Beauty Of Not Finishing

Charlie Boluk

Corporate Life

The Game Was Real. I Just Didn't Know I Was Playing It.

Oct 8, 2026

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5 min read

The Game Was Real. I Just Didn't Know I Was Playing It.

Charlie Boluk

Personal Growth

If You're Evil, You're At Least Competent.

Oct 1, 2026

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5 min read

If You're Evil, You're At Least Competent.

On Peter Thiel, Rome, the school system, and the third option nobody talks about.

Charlie Boluk

Happiness

The Twenty Minutes That Nobody Can Take From You

Sep 29, 2026

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4 min read

The Twenty Minutes That Nobody Can Take From You

On morning walks, curious questions, the four idols everyone chases, and what you will actually remember.

Charlie Boluk

Happiness

Four Thousand Weeks — And What You Put in the Dots

Sep 24, 2026

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4 min read

Four Thousand Weeks — And What You Put in the Dots

At 50 I counted the dots I had left. The first feeling was regret. Then something shifted.

Charlie Boluk

Corporate Life

The Word Entrepreneur Has Been Stolen. Here Is What It Actually Means.

Sep 22, 2026

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5 min read

The Word Entrepreneur Has Been Stolen. Here Is What It Actually Means.

On tech bros, corporate innovation theatre, skin in the game, and why the craft is coming back.

Charlie Boluk

Mindfulness

Sep 17, 2026

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5 min read

My Grandmother's Wardrobe

On unread books, unlearned languages, and the version of yourself still waiting in a drawer.

Charlie Boluk

Personal Growth

Sep 15, 2026

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5 min read

May You Live in Interesting Times

Is civilisation collapsing or am I just an anxious middle-aged person? Six years of evidence either way.

Charlie Boluk

Success

Sep 8, 2026

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7 min read

What the Moleskine Taught Me About Luck

On the things we planned, the things that arrived differently, and why gratitude is accurate accounting.

Charlie Boluk

Personal Growth

Sep 3, 2026

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5 min read

The Performance of Okayness

Life is the sum of choices we made and regret, and choices we never made and wonder about. The wondering is usually worse

Charlie Boluk

Corporate Life

Same Bean. Different Roast. What Coffee Revealed About Every Person I Ever Hired.

Sep 1, 2026

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4 min read

Same Bean. Different Roast. What Coffee Revealed About Every Person I Ever Hired.

What selecting, roasting and brewing coffee taught me about hiring, managing and losing good people.

Charlie Boluk

why can't I start anything.

Motivation Is Not a Feeling You Wait For. It Is a Formula You Can Adjust.

Aug 30, 2026

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2 min read

Motivation Is Not a Feeling You Wait For. It Is a Formula You Can Adjust.

Why your brain always picks YouTube over the gym — and what to do about it.

Charlie Boluk

Depression

I Am Not Naturally a Happy Person. My Humble Advice on What Actually Helps

Aug 30, 2026

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2 min read

I Am Not Naturally a Happy Person. My Humble Advice on What Actually Helps

What I shared on Reddit that reached 550,000 people in 48 hours.

Charlie Boluk

Happiness

50 Years Old, Procrastinating Since 17. My Humble Advice.

Aug 30, 2026

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2 min read

50 Years Old, Procrastinating Since 17. My Humble Advice.

Stop beating yourself up. A surgeon who can't start their tax return isn't lazy. Neither are you.

Charlie Boluk

Corporate Life

Aug 27, 2026

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5 min read

The Last Generation That Will Retire

The broken promise, the rising age, and one way out — even if you cannot swim.

Charlie Boluk

Happiness

The Only Test That Actually Matters for a Friendship

Aug 25, 2026

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4 min read

The Only Test That Actually Matters for a Friendship

My daughter's birthday party, a prominent man's funeral, and what the silence after leaving taught me about who is actually there.

Charlie Boluk

Corporate Life

Which Animal Are You? What Nobody Tells You About the Corporate Forest

Aug 20, 2026

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6 min read

Which Animal Are You? What Nobody Tells You About the Corporate Forest

The monkey kings, the snakes, the jackals — and why the lions are rarely at the top.

Charlie Boluk

Mindfulness

Aug 18, 2026

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5 min read

Me, Myself and My Biases

Six cognitive patterns I keep finding in my trading account, my career, and my closest relationships.

Charlie Boluk

Happiness

What Does a World of Warcraft Player, a Surgeon, and a Corporate Executive Have in Common?

Aug 13, 2026

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6 min read

What Does a World of Warcraft Player, a Surgeon, and a Corporate Executive Have in Common?

More than you think — and it explains why smart people struggle with the wrong kind of problem.

Charlie Boluk

Depression

The Sandwich Generation — You Are Not Failing. The Architecture Is.

Aug 11, 2026

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6 min read

The Sandwich Generation — You Are Not Failing. The Architecture Is.

On carrying more than one person should, the impossible arithmetic of middle age, and what actually helps.

Charlie Boluk

Layoff

AI Is Not Taking Your Job. It Is Taking Your Identity — And Keeping the Profit.

Aug 7, 2026

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7 min read

AI Is Not Taking Your Job. It Is Taking Your Identity — And Keeping the Profit.

The economists know it. The Pope is worried about it. And my almost-six-year-old has no idea yet.

Charlie Boluk

Success

Aug 4, 2026

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5 min read

Success and Failure Are Both Illusions. So What Are You Actually Comparing?

Agassi was more alive at 140th than at number one. Where are you today?

Charlie Boluk

FIRE

Financial Independence Is Not a Number. It Is Permission.

Jul 31, 2026

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4 min read

Financial Independence Is Not a Number. It Is Permission.

What losing a friend at 49 taught me about money, time, and what we are actually saving for.

Charlie Boluk

Fear of

The White Monster — What Fear Actually Is and How to Break the Loop

Jul 28, 2026

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6 min read

The White Monster — What Fear Actually Is and How to Break the Loop

What my almost-six-year-old daughter taught me about fear — and what tiny experiments actually do about it.

Charlie Boluk