The ONE Thing

If you've ever taken a new job or a new title and kept feeling like the old you, Shannon Anderson-Finch has a name for it: the gap between a change and a transition. Most people try to skip it.

Shannon spent 15 years at Google and Deloitte, where she was named Coach of the Year, before starting her own practice. She now coaches new VPs at a large retailer and a first-time hospital president through that same gap.

Her model runs in the wrong order: an ending, then a messy middle where you're neither here nor there, and only then a beginning. The middle is where she watches high achievers get impatient, and it's where she does most of her coaching. Jay tells a story in here about the morning his own affirmation changed one word on its own, and it gave Shannon goosebumps.

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In this episode, you’ll learn:

-How to tell the difference between a minor change and a major transition

-Why big transitions often require an identity shift

-How to navigate the messy middle without rushing through it

-Why strengths, feedback, and core values can help you grow into a new role

-How experimenting with a new identity can make it start to feel natural

Chapters:

[00:00] When Change Requires a New Identity

[08:38] The End Comes Before the Beginning

[12:00] The Strengths That Move With You

[19:24] Don’t Rush the Messy Middle

[27:09] Becoming Who the New Role Requires

[34:59] The Challenge: Try On Your New Identity

Links & Tools from This Episode:

• The ONE Thing Operating System

• Anderson Finch Coaching

• Free Resources

Produced by NOVA

We spend a lot of energy trying to make life faster, easier, and more convenient. But what might we lose when we remove too much of the hard?

Jay breaks down the “fun scale,” from Type One Fun that feels good in the moment to Type Two Fun that feels difficult while you’re doing it but becomes meaningful in retrospect. Then there’s Type Three Fun: hard experiences that never seem worth it.

The difference often comes down to three things: choice, completion, and connection. Did you choose the challenge? Can you see a finish line? Is the struggle connected to something meaningful?

Jay also explores what calculators, GPS, AI, and other conveniences can quietly take away when we stop exercising skills ourselves, and why leaders should help their teams “do hard better” instead of trying to remove every challenge.

Know someone who may find this episode helpful? Share it with them:

https://the1thing.com/podcast-episode/type-2-work-and-the-hidden-cost-of-convenience

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In this episode, you’ll learn:

-What Type 1, Type 2, and Type 3 experiences look like

-Why some hard experiences become your most meaningful memories

-How choice, completion, and connection help you decide if hard work is worth it

-Why making everything easier can weaken skills you still need

-How to help yourself and your team “do hard better”

Chapters:

[00:00] Why We Need More Type 2 Experiences

[03:51] What Convenience Is Costing Us

[06:43] The 3 Tests for Hard Things

[07:29] Why Hard Needs a Finish Line

[11:16] How to Do Hard Better

[14:48] The Challenge: Test One Hard Thing

Links & Tools from This Episode:

• The ONE Thing Operating System

• Oliver Burkeman and his previous conversation with Jay

• Free Resources

Produced by NOVA

Mallory Rowan was building a successful powerlifting apparel company, competing at a high level, and finishing university when her body finally forced her to stop. A routine doctor’s visit revealed that she had been living with pneumonia, but the warning signs had appeared long before: irritability, emotional exhaustion, unexplained health issues, and the growing feeling that she was no longer herself.

Mallory joins Jay to share what it took to recover, ask for support, and separate her identity from her work. She explains how burnout changed the way she builds businesses, from creating stronger boundaries to designing for her personality, interests, and changing seasons of life.

They also explore Mallory’s “toddler test” for uncovering what you truly want, why financial security can give entrepreneurs more freedom to take meaningful risks, and how expanding your options can protect both your health and your ambition.

Know someone who may find this episode helpful? Share it with them: https://the1thing.com/podcast-episode/building-a-burnout-proof-business-with-mallory-rowan/

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In this episode, you’ll learn:- How to recognize the emotional and physical signs of burnout- Why separating your identity from your work matters- How to design a business around your strengths and season of life- How the “toddler test” reveals what you actually want- Why financial security creates more freedom to take meaningful risks

Chapters:

[00:00] The Burnout Wake-Up Call

[05:37] When Pushing Through Stops Working

[13:38] You Are More Than Your Work

[19:18] What Do You Really Want?

[25:54] Making Work Optional

[33:12] Sustainable Ambition

[37:07] The Challenge: Find Six Solutions

Links & Tools from This Episode:

• The ONE Thing Operating System

• Check out FundClub here

• Mallory Rowan’s Website

• Follow Mallory Rowan on Instagram

• Free Resources

Produced by NOVA

Simone Stolzoff, author of How to Not Know, joins Jay to explore why our search for certainty often leads us into three traps: comfort, hubris, and control. They discuss how replacing those instincts with growth, humility, and acceptance can help us move forward without having every answer.

Simone shares practical ways to build your tolerance for uncertainty, including introducing small doses of randomness into your routine, looking to your past for evidence that you can handle difficult situations, and trusting your future self to solve future problems.

They also break down four questions that can bring clarity during a crisis: What is really happening? What are the trade-offs? What are your priorities? What is the next right action?

Know someone who may find this episode helpful? Share it with them:

https://the1thing.com/podcast-episode/how-not-to-know-the-science-of-uncertainty-with-simone-stolzoff/

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We talk about:

[00:00] Why Uncertainty Makes Us So Uncomfortable

[01:34] The Three Traps of Certainty

[06:53] How to Get Better at Not Knowing

[11:36] What Happens When You Randomize Your Life

[20:58] Four Questions for Navigating a Crisis

[34:06] Let Go of the Life You Didn’t Choose

[38:52] The Challenge: Choose Who You Want to Become

Links & Tools from This Episode:

• The ONE Thing Operating System

• How to Not Know by Simone Stolzoff

• The Good Enough Job by Simone Stolzoff

• Follow Simone Stolzoff on Instagram: @thepizza_bagel

• Free Resources

Produced by NOVA

There is no such thing as the perfect productivity system. No matter how optimized your day is, or how many AI agents you have running 24/7, the harsh reality is that you’ll never truly be caught up. And that’s good news.

Oliver Burkeman wrote The Guardian's psychology column "This Column Will Change Your Life" for years before his four books on time and ambition. Four Thousand Weeks was an instant New York Times and Sunday Times bestseller, and his follow-up, Meditations for Mortals, is one of Jay's favorite reads of the last two years.

Jay and Oliver take apart the fantasy underneath every productivity system: the day you're finally on top of everything. The more you optimize, the more work floods in to fill the space. It's the same reason widening a freeway attracts more cars. Burkeman, a self-described "old man yells at cloud" AI skeptic, has watched people feel guilty at family dinner because their AI agents are sitting idle. And the skill he says this all comes down to is one nobody teaches: "the tolerance of the anxiety of letting all the other things go undone for now."

In this episode, you'll learn:

- What to do if you're an anxious, insecure overachiever

- Why it's so uncomfortable to do nothing

- Whether to-do lists actually help

- Why you'll have to say no to things you genuinely want

- How much of your day you should plan in advance

Chapters:

(00:00) Introduction

(01:02) Waiting for Real Life to Start

(12:48) The Jevons Paradox

(17:33) The Discomfort of Doing Nothing

(20:57) The Productivity Paradox

(30:03) Jay vs. Oliver on Time Blocking

(33:58) Time Surfing: A Day With No Plan

(39:19) Just Actually Do It

Know someone who may find this episode helpful? Share it with them: https://the1thing.com/podcast-episode/youll-never-get-on-top-of-everything-and-thats-okay-with-oliver-burkeman/

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Links & Resources:

• Four Thousand Weeks by Oliver Burkeman

• Meditations for Mortals by Oliver Burkeman

• Follow Oliver Burkeman on X

• Free Resources

Produced by NOVA