Writing By Category

Books & Reading | Creativity & The Creator Economy | Freelancing | Leisure, Rest & Non-Doing | Modern Careers | Organizations & Culture | Reflections & Personal Essays | Travel | Wisdom, Success & Philosophy | Work Beliefs & History of Work | Latest

Modern Careers|Top

Leap Capital: The Financial Resources You Need To Quit Your Job
How to answer “what do you do?” on a pathless path
The Case For Quiet Quitting (and the dangers of slacking at work)
The Inspiration Deficit – Or Why So Many Young People Still Crave More Challenging Work
Accidental Meaning: How The Baby Boomers Misled Us About What Leads To A Happy Life
How Obsession With Work Killed Our Connection With Leisure
The Inevitable Decline Of The Elite Full-Time MBA
Don’t Follow Your Passion, Work In The Corporate World First
The Knowledge Worker Mind & The Birth Of Careerism
Spaceship You: How To Understand Who You Are as a Remote Worker
The best advice on working remotely your boss doesn’t want you to see
Questions About The Future Of Work
Hamsternomics: Printing Money, The Economy & Work Beliefs
Dear Leaders, It’s Time To Wake The F*ck Up
Rethinking Meetings In A Remote World
Virtual Spaces: How To Teach & Engage With Virtual Communities
Work From Home
The Reality of The New Economy: Go Tech, Go Solo Or You’re SOL
The Boomer Blockade: How One Generation Reshaped the Workforce and Left Everyone Behind
The Big Law Trap | Guest Essay by Ranjit Saimbi
The best career and life advice from Scott Adams, Debbie Millman, Hunter Thompson & Others
Hunter S. Thompson’s Life Advice To A Friend Is Priceless
It’s Time We Bury The Idea Of A “Good Career Trajectory”
Reinvention Is The Most Important “Skill” You Need To Have In Today’s World
The Future Of The Prestige Economy: Who Gets Status?

Leisure, Rest & Non-Doing|Top

How To Take A Sabbatical: Stories From Five People Who Took Them
The Ultimate Guide & Reasons To Take A Sabbatical
The Magic of Non-Doing
The Other Side Of Rest: Taking Time Off In An Age Of Anxiety
Vacation is a poor substitute for leisure: Rethinking the role of rest in the modern world

Latest Essays|Top

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Unhinged Habits Book Review: Why You Don’t Need More Productivity

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Ambition Without Trying: Overcoming The Golden Algorithm and What I Learned From Joe Hudson

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Leap Capital: The Financial Resources You Need To Quit Your Job

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Paycheck Envy: Why Self-Employed People Love Recurring Revenue

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Book Review: The Ghost Map – From Miasmas to Germ Theory

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The Long 2024: A Year of Change, Creativity, and Letting Go

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Book Review: “The Organization Man” – How the 1950s Shaped Our Work, Lives, and Aspirations

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Hacking US Healthcare: A Guide to US Healthcare for Self-Employed People

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What if everyone followed The Pathless Path?

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Rethinking Wealth: Four Insights from “Just Keep Buying”

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Question People and Answer People

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Thanks for purchasing the Black Friday deal!

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How to answer “what do you do?” on a pathless path

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The Case For Quiet Quitting (and the dangers of slacking at work)

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Escape Shouldandia!

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Solopreneur & Creator Week-In-The-Life (as a parent)

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Seven Reflections on Seven Years Of Self-Employment

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How Do You Leave Money On The Table?

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New Additions, New Heights & Open Questions | 2023 Annual Review

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How To Take A Sabbatical: Stories From Five People Who Took Them

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Die With Zero: Why Too Many Save Too Much for Too Late In Their Lives (Book Review)

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The Way of Mediocre Man

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A Pebble In My Shoe (Excerpt From The Pathless Path)

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Leaning Into Ambition & Deeper Commitments: (Still) Enjoying The Journey | 2022 Annual Review

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The “Wild Problem” Of A Life Well Lived: A Book Review of Russ Roberts’ Wild Problems

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Selling My Time Too Cheap: How Full-Time Year-Round Work Blinds Us To The Joys of Life

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The Inspiration Deficit – Or Why So Many Young People Still Crave More Challenging Work

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Too Big To Think: Why Prestigious Institutions Stopped Generating Good Ideas

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Don’t Find A Niche, Find A Mode

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Ship, Quit & Learn – A Framework for Finding Work Worth Doing

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My “Creative Engine”: A Curiosity-First Second Brain Approach For Creating Online

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Finishing My Book, From Mexico to Taiwan to the US | 2021 Annual Review

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Do We Really Want Happiness? Lessons from Socrates, Kahneman & Maslow

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Designing Your Own Infinite Game In The Creator Economy

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“Ambition Is Frozen Desire” – Excerpt From David Whyte’s Consolations