Greg McKeown and Diana Chapman (#740)

This episode is a two-for-one, and that’s because the podcast recently hit its 10-year anniversary and passed one billion downloads. To celebrate, I’ve curated some of the best of the best—some of my favorites—from more than 700 episodes over the last decade. I could not be more excited. The episode features segments from episode #355 “Greg McKeown — How to Master Essentialism” and episode #536 “Diana Chapman — How to Get Unstuck, Do “The Work,” Take Radical Responsibility, and Reduce Drama in Your Life.”

Please enjoy!

Bios of guests may be found at tim.blog/combo.

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

Brought to you by Momentous high-quality supplements; Wealthfront high-yield savings account; and Helix Sleep premium mattresses.

Transcript of the full Greg McKeown episode | Transcript of the full Diana Chapman episode | Transcripts of all episodes

Listen onApple Podcasts

Listen onSpotify

Listen onOvercast

#740: Greg McKeown and Diana Chapman

This episode is brought to you by Momentous Fiber+. Most Americans (~95%!) do not meet the recommended fiber intake. Fiber isn’t just about “staying regular”; it’s one of the most overlooked meta-nutrients for everyday health and fitness. It supports digestion, helps keep blood sugar stable, and feeds critical gut bacteria that affect nearly every aspect of life. I focus on whole foods first, but I also take quality supplements as cheap insurance for chaotic days, travel, and more. Momentous Fiber+ makes it easy. It supports your gut from multiple angles as a three-source blend: soluble fiber, insoluble fiber, and resistant starch. It mixes smoothly into water, smoothies, oatmeal, or yogurt, and it comes unflavored or in a natural cinnamon. Fiber+ is NSF Certified for Sport®, which means it’s independently tested. So what’s on the label is what’s in the product. If you’re dialing in your nutrition but lacking fiber, this is a simple fix. Get 35% off your first subscription with code TIM at LiveMomentous.com/Tim.

This episode is brought to you by Helix Sleep! Helix was selected as the best overall mattress of 2025 by Forbes and Wired magazines and best in category by Good Housekeeping, GQ, and many others. With Helix, there’s a specific mattress to meet each and every body’s unique comfort needs. Just take their quiz—only two minutes to complete—that matches your body type and sleep preferences to the perfect mattress for you. They have a 10-year warranty, and you get to try it out for a hundred nights, risk-free. They’ll even pick it up from you if you don’t love it. And now, Helix is offering listeners 27% off all mattress orders for a limited time at HelixSleep.com/Tim.

This episode is brought to you by Wealthfront! Wealthfront is a financial services platform that offers services to help you save and invest your money. Right now, your cash can earn 3.30% APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account from its network of program banks. That’s 8 times more interest than a typical savings account at a bank, according to FDIC.gov as of 1/22/2026 (Wealthfront’s 3.30% APY vs. 0.39% average savings rate). Right now, for a limited time, Wealthfront is offering new clients that use my sign-up link an additional 0.75% boost over the base rate for three months, meaning you can get up to 4.05% APY, limited to $150,000 in deposits. Terms & Conditions apply. Visit Wealthfront.com/Tim to get started.

The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC (“WFB”), member FINRA/SIPC. Wealthfront Brokerage is not a bank. The 3.30% Base APY on cash deposits is as of January 30, 2026, is representative, subject to change, and requires no minimum balance. The overall boosted rate is subject to change if the base rate decreases during the three-month promotional period. Tim Ferriss, who’s not a client, receives cash compensation from Wealthfront Brokerage LLC for advertising and holds a non-controlling equity interest in the corporate parent of Wealthfront Brokerage LLC, which creates an incentive that results in a conflict of interest. Tim expresses his own opinions and Wealthfront does not endorse, sponsor, or promote them. This ad may not reflect the experience of other Cash Account clients, and similar outcomes are not guaranteed. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Securities investments: not bank deposits, not bank-guaranteed or FDIC-insured, and may lose value. See full disclosures here.

What was your favorite quote or lesson from this episode? Please let me know in the comments.

SHOW NOTES

[05:26] Notes about this supercombo format.
[06:28] Enter Greg McKeown.
[06:49] What is non-essential?
[07:46] Overcoming the planning fallacy.
[13:30] The problem with taking ownership of someone else’s problems.
[15:44] How to avoid committing to the unsustainable.
[21:26] Three rules.
[25:28] The personal quarterly offsite.
[33:05] Enter Diana Chapman.
[33:22] A transformative gift.
[36:56] The Drama Triangle.
[43:36] The whole-body yes (or no) and how it can serve us.
[46:06] Diana guides an experience to help pay better attention to our whole-body yes (or no).
[54:36] Observations made during the exercise and how Diana recommends using this inventory.
[1:01:39] Fostering playfulness for those who mute their desire to celebrate.
[1:08:28] Diana’s “black belt in practicing candor.”
[1:09:37] Diana’s thoughts on loving pressure and how to bring it into a relationship.
[1:13:24] Applying loving pressure to people you don’t know well.
[1:15:08] Diana’s guidance on introspection leading to perspective shifts; using Byron Katie’s “turnarounds.”
[1:17:48] Diana guides me through a turnaround.
[1:23:58] A turnaround’s purpose is to identify and embrace alternatives, not invalidate the inspected belief.
[1:29:06] The importance of introducing the somatic into the process; suggestions for difficulty with this step.
[1:31:47] The role of the witness in this process.
[1:33:54] Walking the line.
[1:35:40] Welcoming the opportunity to learn from the experience, even if it’s not preferred.
[1:37:35] Alternative tools for dysregulation in the moment.
[1:39:31] Risks Diana and her husband Matt took to keep their relationship vital; who initiated the first difficult conversation.
[1:45:11] How Diana figured out who she needed to be during this time.
[1:47:11] Navigating decision points together as a couple.
[1:49:42] Examples of commitments from The 15 Commitments of Conscious Leadership.
[1:53:22] The Mind Jogger app and how Diana uses it with the commitments.
[1:55:55] Assessing self-awareness in hiring interviews applied to non-job situations.
[1:57:53] Books most gifted.
[1:59:35] Parting thoughts.

SELECTED LINKS FROM THE EPISODE

Connect with Greg McKeown:

Website | Twitter | Facebook | Instagram

Connect with Diana Chapman and the Conscious Leadership Group:

Website | Twitter | Facebook | YouTube

PEOPLE MENTIONED

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.)

3 Comments

Inline Feedbacks

View all comments

Asad

1 year ago

Great Its much helpfull

Kathleen Anderson

Both of these podcasts were super helpful and applicable when they first came out and have implemented some concepts from Greg’s rules for preventing overcommitting ever since hearing this episode back when it came out. From this second listen, I want to implement the quarterly offsite for life planning.
From Diana’s episode, on this second listen I am struck by her permission to interpret an absence of a somatic no as a yes. I completely missed that the first time around, and have been frustrated that I don’t feel a somatic yes or no for many of the un-extreme things that come up.
Happy Memorial Day!

Edi

Since listening to this episode when it originally aired, I’ve put some of the ideas from Greg’s guidelines for avoiding overcommitting into practice. Both of these podcasts were incredibly beneficial and applicable when they first came out.