Many of us feel like we’re drowning in invisible complexity. So I wanted to hit pause and ask a simple question: What are 1-3 decisions that could dramatically simplify my life in 2026? To explore that, I invited five long-time listener favorites: Maria Popova, Morgan Housel, Cal Newport, Craig Mod, and Debbie Millman.
More about today’s guests:
Maria Popova (@mariapopova) thinks and writes about our search for meaning, lensed sometimes through science and philosophy, sometimes through poetry and children’s books, always through wonder. She is the creator of The Marginalian (born in 2006 under the name Brain Pickings), which is included in the Library of Congress permanent digital archive of culturally valuable materials. Her books and projects include Traversal, The Universe in Verse, Figuring, The Coziest Place on the Moon, and An Almanac of Birds: 100 Divinations for Uncertain Days.
Morgan Housel (@morganhousel) is a partner at The Collaborative Fund. His book The Psychology of Money has sold more than three million copies and has been translated into 53 languages. Morgan is also the author of Same As Ever: A Guide to What Never Changes and The Art of Spending Money.
Cal Newport is a professor of computer science at Georgetown University, where he is also a founding member of the Center for Digital Ethics. In addition to his academic work, Newport is a New York Times bestselling author who writes for a general audience about the intersection of technology, productivity, and culture. His books have sold millions of copies and been translated into over forty languages. He is also a contributor to The New Yorker and hosts the popular Deep Questions podcast. His latest book is Slow Productivity: The Lost Art of Accomplishment Without Burnout.
Craig Mod (@craigmod) is a writer, photographer, and walker living in Tokyo and Kamakura, Japan. He is the author of Things Become Other Things and Kissa by Kissa. He also writes the newsletters Roden and Ridgeline and has contributed to The New York Times, The Atlantic, Wired, and more.
Debbie Millman (@debbiemillman) has been named one of the most creative people in business by Fast Company and one of the most influential designers working today by Graphic Design USA. She is the host of Design Matters—a great show and one of the world’s longest-running podcasts. She is also chair of the Masters in Branding Program at the School of Visual Arts in New York City, editorial director of Print magazine, a Harvard Business School Case Study, and a member of the board of directors at the Joyful Heart Foundation.
Please enjoy!
This episode is brought to you by:
- Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business: Shopify.com/tim
- Helix Sleep premium mattresses: HelixSleep.com/Tim
Additional podcast platforms
Listen to this episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.
Transcripts
- This episode (coming soon)
- All episodes
SELECTED LINKS FROM THE EPISODE
Books
- The Psychology of Money — Morgan Housel
- Same As Ever — Morgan Housel
- The Art of Spending Money — Morgan Housel
- 11/22/63 — Stephen King
- Deep Work — Cal Newport
- Digital Minimalism — Cal Newport
- A World Without Email — Cal Newport
- Things Become Other Things — Craig Mod
- Kissa by Kissa — Craig Mod
- The Writing Life — Annie Dillard
Films & TV
- Sinners (2025, dir. Ryan Coogler)
People
- Maria Popova
- Morgan Housel
- Cal Newport
- Craig Mod
- Debbie Millman
- Annie Dillard
- Nancy Lynch
- Ryan Coogler
Podcasts & Media
- Cal Newport’s Masterclass
- Design Matters podcast
- Deep Questions podcast
Want to hear another episode with someone committed to the disciplined pursuit of less? Listen to my conversation with Greg McKeown, author of Essentialism and Effortless, in which we discussed how Gandhi would sum up Essentialism, the joys of simplicity, the difference between effortless action and effortless results, questions to cope with pet peeves, actionable gratitude, and much more.
Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)