336: Letting Go of Productivity Guilt with Madeleine Dore (Free Time Crossover)

“You have to live spherically—in many directions. Never lose your childish enthusiasm—and things will come your way.” —Federico Fellini

This week’s delightful guest, Madeleine Dore, reminded me of this wonderful quote while reading her book, one that I know you will love as much as I did: I Didn’t Do The Thing Today: Letting Go of Productivity Guilt.

We talk about widening the measure and meaning of a day beyond our to-do lists, discovering the call of a new topic, shaping a big idea “blob of clay,” how she collects all the great quotes and stories for her book, why she sees herself as more of a guinea pig than an expert (and freelancer valuing independence even more than business owner), and how she decides when to sunset a project, rather than “maintaining something at all costs.”

This crossover episode originally aired on the Free Time podcast on April 25, 2023.

More About Madeleine: Madeleine Dore is a writer and interviewer exploring how we can broaden the definition of a day well spent. As a labor of love, Madeleine spent over five years asking creative thinkers how they navigate their days on her popular blog Extraordinary Routines and podcast Routines & Ruts. The lessons culminated in her first book, I Didn’t Do The Thing Today: Letting Go of Productivity Guilt. Madeleine continues to write, speak and ask questions—but mostly tries to hold things lightly.

🌟 3 Key Takeaways

• We all go through creative phases of being a sponge vs. squeezing it: the former is a time to absorb the world and take in inspiration, even if it might look from the outside like we’re not doing anything.
• When caught in a deflating comparison spiral: Get up close, use it as a guide, return to what you want to do, and do it!
• Identify what is most important to you, and change the questions you ask as a result. For example, Madeleine’s decision to favor more time over more money means when considering a new project or direction, asking not “How much will this earn?” but “How much [free] time will this enable?”

📝 Permission: Stop measuring the day by how productive you were. Be curious and expansive when reviewing your day, including your internal accomplishments, moments of connection, or even moments of idleness. Instead of trying to optimize your day only through the lens of productivity, occupy and embrace your day for what it wants to be.

✅ Do (or Delegate) This Next: Identify one area of your business or creative projects that may be languishing. What would happen if you gave yourself permission to close it out completely to create space for what’s next?

🔗 Resources Mentioned

• Madeleine on the web, Instagram: @madeline_dore, Facebook
• Substack: On Things
• Madeleine’s podcast: Routines & Ruts

📚 Books Mentioned

• Madeleine’s book: I Didn’t Do The Thing Today: Letting Go of Productivity Guilt
• Free Time: Lose the Busywork, Love Your Business
• Pivot: The Only Move That Matters Is Your Next One

🎧 Related Episodes

• 2 Pages with MBS: How to Be Alive: Madeleine Dore [reads] Encyclopedia of an Ordinary Life
• Free Time: 170: 🌈 “Imagine a World of Abundance” ✨, 169: Running a Goal-Free Business with Stephen Shapiro, 057: You+ vs. You 2.0 with MBS, 036: Shaping Big Ideas — Notion Walkthrough #2
• Pivot: 287: Solving Pivot Puzzles with A.J. Jacobs, 305: Is What You Are Wanting Actually What’s Best For You? With Luke Burgis

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