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

Free Time with Jenny Blake

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

❤️ Jenny Blake

and

Chris Guillebeau

Apr 15, 2025

Transcript

👋 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. 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.”):