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273: Navigating Time Anxiety, Reducing Inbox Dread, and Creating Ease Loops with Chris Guillebeau

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Apr 15, 2025

Guest

Chris Guillebeau

In this engaging conversation, Chris Guillebeau—best-selling author and world traveler—tackles the intriguing concept of time anxiety. He shares personal insights on productivity patterns and strategies to combat feelings of inadequacy. The discussion encourages evaluating the meaningfulness of daily experiences and setting boundaries to handle inbox anxiety. Chris also reflects on the impact of aging on values and offers ways to navigate comparison in professional settings, promoting a focus on personal journeys and intentional living.

50:18

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Episode notes

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ADVICE

Daily Reflection Question

Ask yourself, "Did today matter?" to measure day effectiveness beyond productivity.
Reflect on meaningful progress, relationships, and self-care to affirm your day had value.

insights

INSIGHT

Two Types of Time Anxiety

Time anxiety has two main types: existential (life running out) and daily routine (not enough time).
These types overlap and shape our distress or discontent around time usage.

volunteer_activism

ADVICE

Gentle, Actionable Writing Approach

Write gently and viscerally, helping overwhelmed people find immediate relief.
Use short chapters and practical sequencing to guide from understanding to action easily.

Get the Snipd Podcast app to discover more snips from this episode

Navigating Time Anxiety

02:11 • 18min

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Evaluating the Meaning of Daily Experiences

19:58 • 3min

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Navigating Inbox Anxiety and Aging Wisdom

22:55 • 14min

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Confronting Time Anxiety and Success Envy

37:05 • 3min

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The Struggle of Comparison and Embracing Ease

40:07 • 8min

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How to Keep House While Drowning

A Gentle Approach to Cleaning and Organizing

KC Davis

This book by KC Davis offers a gentle and compassionate guide to managing home care despite the challenges of anxiety, fatigue, depression, ADHD, or lack of support. Davis shares her personal experiences and practical strategies, such as cleaning in short bursts and using creative shortcuts, to help readers transform their homes into functional and peaceful spaces. The book emphasizes letting go of perfectionism and fostering a healthier relationship between the individual and their home.

The $100 startup

Chris Guillebeau

In this book, Chris Guillebeau shares insights from 1,500 individuals who have built businesses earning $50,000 or more from minimal investments. He focuses on 50 intriguing case studies, highlighting how people with no special skills turned their passions into profitable ventures. The book emphasizes the importance of finding the intersection between your expertise and what others are willing to pay for, and it provides practical advice on starting and growing a business without needing an MBA, a business plan, or employees. Guillebeau stresses key principles such as the importance of action over planning and the value of selling solutions rather than teaching skills.

Free Time

Lose the Busy Work, Love the Business

Daily Rituals: How Artists Work is a book that delves into the daily routines and working habits of more than 161 highly successful and creative individuals. The book, written by Mason Currey, provides insights into how these creatives structured their days to manage their work and personal lives. It includes profiles of famous figures such as Anthony Trollope, Karl Marx, Woody Allen, Agatha Christie, and many others, highlighting their unique routines, habits, and quirks. The book aims to show how grand creative visions are translated into small daily increments and how these routines influence the work itself. It also explores broader themes such as the balance between comfort and creativity, and the importance of forming good habits to free the mind for more interesting fields of action.

Atomic Habits

James Clear

Atomic Habits by James Clear provides a practical and scientifically-backed guide to forming good habits and breaking bad ones. The book introduces the Four Laws of Behavior Change: make it obvious, make it attractive, make it easy, and make it satisfying. It also emphasizes the importance of small, incremental changes (atomic habits) that compound over time to produce significant results. Clear discusses techniques such as habit stacking, optimizing the environment to support desired habits, and focusing on continuous improvement rather than goal fixation. The book is filled with actionable strategies, real-life examples, and stories from various fields, making it a valuable resource for anyone seeking to improve their habits and achieve personal growth.

The Art of Non-Conformity

Set Your Own Rules, Live the Life You Want, and Change the World

Chris Guillebeau

Based on Chris Guillebeau's popular online manifesto 'A Brief Guide to World Domination,' this book encourages readers to challenge conventional norms and live unconventional, remarkable lives. It explores creative self-employment, radical goal-setting, contrarian travel, and embracing life as a constant adventure. The book is organized into three parts: The Remarkable Life, Reclaiming Work, and The Power of Convergence, providing practical advice and inspiring stories to help readers design their own path to success and make a meaningful impact.

Wanting

The Power of Mimetic Desire in Everyday Life

Luke Burgis

In 'Wanting: The Power of Mimetic Desire in Everyday Life,' Luke Burgis delves into the concept of mimetic desire, which is the tendency to imitate the desires of others. Drawing on the work of René Girard, Burgis explains how our desires are mediated by models and how this can lead to rivalry, conflict, and unfulfilling pursuits. The book distinguishes between 'thin' desires, which are superficial and mimetic, and 'thick' desires, which are deeper and more lasting. Burgis provides tactics for identifying and transforming these desires, such as creating a hierarchy of values, finding sources of wisdom that withstand mimesis, and practicing empathy. The book aims to help readers gain control over their desires and find more meaning in their lives by making intentional choices rather than blindly following mimetic forces.

Time Anxiety

The Illusion of Urgency and a Better Way to Live

Chris Guillebeau

Side hustle

From Idea to Income in 27 Days

Chris Guillebeau

This book provides a detailed roadmap for creating an additional stream of income without quitting your day job. It guides readers through brainstorming ideas, selecting the best concept, launching, and refining their side hustle to generate income quickly. The book emphasizes that anyone can start a side hustle without needing extensive entrepreneurial experience or resources.

The Pursuit of Happiness

How Classical Writers on Virtue Inspired the Lives of the Founders and Defined America

Jeffrey Rosen

Laziness Does Not Exist

Devin Price

👋 Hello Free Timers! While we’re still not resuming the podcast’s regular publishing schedule, I’m popping into your feed today to share a fun conversation with my friendtor of over fifteen years, Chris Guillebeau. We’re discussing his new book, Time Anxiety: The Illusion of Urgency and a Better Way to Live — it was too aligned with Free Time not to share!

📝 View full show notes with all resources mentioned at http://itsfreetime.com/episodes/273.

More about Chris: Chris is the author of several other bestselling books to help you live an unconventional life, think for yourself, see the world, and earn extra money, including The Money Tree, The $100 Startup (a global bestseller), and The Art of Non-Conformity, which was translated into 30+ languages. During a lifetime of self-employment that included a four-year commitment as a volunteer executive in West Africa, he visited every country in the world (193 in total) before his 35th birthday. Every day since January 1, 2017, his podcast, Side Hustle School, has offered a new idea, tip, or short story to help listeners create a new source of income without quitting their jobs.

Learn more about your ad choices. Visit megaphone.fm/adchoices

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