How to Simplify Your Life in 2026 — New Tips from Maria Popova, Morgan Housel, Cal Newport, Craig Mod, and Debbie Millman (#857)

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
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Transcripts

• This episode
• All episodes

SELECTED LINKS FROM THE EPISODE

• Connect with Maria Popova:

The Marginalian | Twitter | Instagram | Threads | Bluesky | Facebook

• Connect with Morgan Housel:

Website | Twitter | The Morgan Housel Podcast

• Connect with Cal Newport:

Website | Blog | YouTube | Deep Questions Podcast

• Connect with Craig Mod:

Website | Instagram | Threads | Bluesky | On Margins Podcast | SW945 Podcast
Roden (Monthly Newsletter) | Ridgeline (Weekly Newsletter)

• Connect with Debbie Millman:

Website | Twitter | Instagram | Threads | Bluesky | Facebook | Design Matters Podcast

Books

• The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness by Morgan Housel
• Same as Ever: A Guide to What Never Changes by Morgan Housel
• The Art of Spending Money: And Other Simple Choices That Lead to a Rich Life by Morgan Housel
• 11/22/63 by Stephen King
• Deep Work: Rules for Focused Success in a Distracted World by Cal Newport
• Digital Minimalism: Choosing a Focused Life in a Noisy World by Cal Newport
• A World Without Email: Reimagining Work in an Age of Communication Overload by Cal Newport
• Things Become Other Things: A Memoir of Walking Japan by Craig Mod
• Kissa by Kissa: How to Walk Japan by Craig Mod
• Books by Debbie Millman
• The Writing Life by Annie Dillard

Films & TV

• 11.22.63
• Mad Max
• Sinners

People

• Maria Popova
• Morgan Housel
• Cal Newport
• Craig Mod
• Debbie Millman
• Annie Dillard
• Stephen King
• John F. Kennedy
• Kelly Hayes
• Nancy Lynch
• Ryan Coogler

Podcasts & Media

• The Morgan Housel Podcast
• Deep Questions
• Cal Newport’s Masterclass
• On Margins
• SW945
• Design Matters

Recommended Reading

• Annie Dillard on Unselfconsciousness by Maria Popova | The Marginalian
• Too Many People Make These Long-Term Investing Mistakes by Morgan Housel | Inc.
• Engaging With History by Morgan Housel | Collaborative Fund
• The Neuroscience of Busyness by Cal Newport | Study Hacks Blog
• What I Learned from MasterClass by Cal Newport | Study Hacks Blog
• How I Learned to Concentrate by Cal Newport | The New Yorker
• Do You Drink? by Craig Mod | Ridgeline
• Tokyo Walk, TBOT Cover, Aloneness by Craig Mod | Roden
• Memberships Work by Craig Mod | Special Projects
• Debbie Millman on the Power of Courage over Confidence, Embracing Criticism, and Overcoming Fear | Creative Boom

TIMESTAMPS

• [00:00:00] Start.
• [00:01:49] Maria Popova: Writer, cherisher, boundary architect.
• [00:02:04] The Cherish Quotient: Stop giving hours to people who rank as “fine.”
• [00:03:15] When you apologize for your priorities, you’re apologizing for your life. Stop!
• [00:04:41] Morgan Housel: Author of three books, evangelist of doing nothing.
• [00:04:50] The do-nothing thesis: Be average long enough and you’ll end up in the top 1%.
• [00:08:42] Read more history, fewer forecasts — and watch the news lose its power over you.
• [00:09:32] How Stephen King’s 11/22/63 illustrates the futility of prediction.
• [00:12:21] Cal Newport: Computer science professor whose body rejects busyness.
• [00:12:36] What deserves a “yes” when the default is “no?”
• [00:16:38] Deep Work sells two million copies and creates a schizophrenic double life.
• [00:19:07] The unifying insight: Both careers were always about technology and human flourishing.
• [00:24:07] Craig Mod: Writer, photographer, long-haul walker, full-time resident of Japan.
• [00:24:46] How quitting alcohol has been Craig’s highest-ROI decision.
• [00:27:13] Therapy after a decade of sobriety: The cliché that actually cleared the water.
• [00:30:27] The compounding interest that comes from committing to one craft.
• [00:33:09] Debbie Millman: Designer whose four-month decision changed the course of her life.
• [00:34:30] How being offered the CEO seat at her company led to four months of paralysis.
• [00:36:10] The sentence that broke the spell: “If it takes four months, you probably don’t want it.”
• [00:37:38] Ambition changes shape: Validation isn’t fulfillment, and power isn’t purpose.

QUOTES FROM THE EPISODE

“The moment you begin apologizing for how you manage your time, you are essentially apologizing for your priorities, which means apologizing for your life.”

— Maria Popova

“The fewer decisions [we] have to make, the better we’re going to do.”

— Morgan Housel

“What I need in my life is autonomy and space to work on my own terms, to produce cool things over a long amount of time, not to do a lot of stuff in the short term.”

— Cal Newport

“Easily the lowest energy in/biggest impact out simplification of my life has been to drop alcohol by the side of the road like a sack of stinky, dead cats.”

— Craig Mod

“There’s a particular kind of simplicity that comes not from doing less, but from doing what feels really true. Simplicity isn’t only about minimalism. I think it’s also about coherence.”

— Debbie Millman

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Want to hear even more strategies for cutting the noise? Check out the last “How to Simplify Your Life” episode, featuring Derek Sivers, Seth Godin, and Martha Beck, in which they discussed radical first-principles for living, why simplifying is hard work, making “no” your default answer, building a life around deep peace rather than dopamine, and much more.

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.