273: Navigating Time Anxiety, Reducing Inbox Dread, and Creating Ease Loops with Chris Guillebeau
👋 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!
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.
🌟 3 Key Takeaways
There are two main forms of time anxiety: EXISTENTIAL—”Time is running out in my life,” and DAILY ROUTINE—”There is not enough time in the day.”
On the Inbox of Shame: “When you’re drowning, you can’t just swim faster.” A few tips that might help assuage guilt and stress: send shorter replies, use delayed send, and recognize the power of doing what you can.
Make free time more memorable by planning a mini-adventure for an upcoming weekend: Having an adventure is an exciting or unusual experience that is often associated with novelty, challenge, and exploration.
📝 Permission
Drop the belief that you’re too late, or that you have missed your chance.
✅ Do (or Delegate) This Next
The next time you’re feeling overwhelmed, try this quick end of day checklist (“no affirmations, no scientific review, no detailed procedural to plan the next day. I just asked myself what would be enough, and when the feelings of overwhelm crept in later, I tried to remember the answers.”):
Did I create something?
Did I help someone?
Did I take some amount of time for myself?
or just one question: Did today matter?
🔗 Resources Mentioned
Articles: Time Anxiety Is the Most Pressing Problem of Our Age ⌛️
People: Emily McDowell (Web, Substack), Laura Vanderkam, ADHD Coach Nicole Bulsara, Brad Montague
Rolling in Doh:
📚 Books Mentioned
Time Anxiety: The Illusion of Urgency and a Better Way to Live by Chris Guillebeau
Chris’s earlier books to help you live an unconventional life: ****Gonzo Capitalism, The Money Tree, The $100 Startup, and The Art of Non-Conformity
How to Keep House While Drowning by K.C. Davis
Laziness Does Not Exist by Devon Price
The Executive Functioning Workbook (get 20% off with promo code EXECUTIVE20)
Daily Rituals: How Artists Work and Daily Rituals: Women at Work by Mason Currey
Storyworthy by Matthew Dicks
Wanting by Luke Burgis
🎧 Related Episodes
Chris’ podcast: Side Hustle School
Emily McDowell’s podcast: Quitted
Pivot: 023: Happiness for People Who Can't Stand Positive Thinking with Oliver Burkeman
305: Is What You’re Wanting Actually What’s Best For You? With Luke Burgis
Free Time: 002: Eliminate Email with Cal Newport
046: Time Margin—Are You Drowning, Treading Water, or Gliding?
141: Process, Permission Slips, and Business Pivots with Tara McMullin
143: Exploring Time, Money, and Energy Capacity with Tara McMullin and Charlie Gilkey
199: Creating Happier Hours and the Diminishing Returns of Too Much Free Time With Cassie Holmes
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✍️ Check out Jenny’s personal business essays on Substack, Rolling in D🤦🏻♀️h
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