THE SHOW
Chris Guillebeau, bestselling author of nine books including The Art of Non-Conformity and his latest Time Anxiety, unpacked big ideas that solve the modern epidemic of feeling simultaneously rushed and directionless. He reveals how our optimization culture created the very problem it claims to solve and why traditional productivity advice fails to address time anxiety. Chris shares insights from his unconventional path from juvenile delinquent to aid worker to bestselling author, discusses his recent ADHD diagnosis and how it shaped his understanding of time, and offers a counterintuitive approach to managing the psychological whiplash between urgency and aimlessness. The conversation covers everything from the myth of perfect time management to why thinking about death daily can actually reduce anxiety. Consider it a modern meditation on living well on your own terms.
Behind His Brilliance: Curiosity and not taking no for an answer
THE GUEST
CHRIS GUILLEBEAU | BESTSELLING AUTHOR + ENTREPRENEUR
Chris Guillebeau is the author of nine books including the New York Times bestsellers The $100 Startup and The Happiness of Pursuit, and the Wall Street Journal bestseller Born for This. His latest book is Time Anxiety: The Illusion of Urgency and a Better Way to Live, released in April 2025.
Guillebeau dropped out of high school as a teenager but began attending college classes at age 16, ultimately graduating with a bachelor’s degree from Athens State University in two and a half years. He spent four years working as an aid worker in West Africa in his early twenties.
In 2008, he founded the blog The Art of Non-Conformity, which discusses entrepreneurship, self-employment, and travel. He completed a personal goal of visiting all 193 countries in the world by his 35th birthday in April 2013.
From 2011 to 2022, he organized the annual World Domination Summit in Portland, Oregon, which attracted notable speakers including Brené Brown, Scott Harrison, and Gretchen Rubin. He has hosted the daily podcast Side Hustle School since January 2017, producing nearly 3,000 episodes.
Guillebeau has written for numerous publications including The New York Times, BusinessWeek, and The Oregonian, and has spoken at companies and events including Google, Facebook, and SXSW.
TOPICS COVERED
- The difference between traditional anxiety and time anxiety
- Why having more choices creates its own form of paralysis
- The two types of time anxiety: existential panic and decision overwhelm
- How ADHD diagnosis changed his relationship with productivity
- Why working for yourself is actually the conservative choice
- The myth that independent work is inherently risky
- Moving from “you can be anything” liberation to burden
- Why curiosity without follow-through is just floating ideas
- The seasonality of creative work and energy cycles
- How to measure success by what you control vs external outcomes
- The power of asking “Did today matter?” over productivity metrics
- Why leaving things undone is a radical act in completion culture
- The difference between hard work and passionate engagement
- How to use death as a clarity tool rather than anxiety trigger
- Platform agnosticism and the creator economy evolution
- The accountability structures that support independent creators
- Why caring about your work trumps optimization systems
- Moving from rules-based to values-based decision making
- The future self trap and why motivation doesn’t transfer
- How to create enough-ness in a never-enough culture
THINGS MENTIONED IN THIS EPISODE
- Chris Guillebeau
- A Year of Mental Health (Chris’s Substack)
- The Art of Nonconformity by Chris Guillebeau
- The $100 Startup by Chris Guillebeau
- Side Hustle by Chris Guillebeau
- Time Anxiety (Chris’s newest book)
- Your First Million by Arlan Hamilton
- Wishcraft by Barbara Sher
- Gretchen Rubin and The Happiness Project
- Derek Sivers’ Hell Yes or No
- Memento Mori (stoic practice of remembering death)
