
349: Embracing Doubt and Going for “Good-Enough” Work with Simone Stolzoff
11/19/23 • 42 min
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As relationship expert Ester Perel says, “Too many people bring the best of themselves to work, and bring the leftovers home.” This is one of several notions that sparked today’s guest, Simone Stolzoff, to reconsider his relationship to work. We’re talking about his unique approach to researching his new book, The Good Enough Job, interviewing over 100 primarily white-collar workers, but only featuring nine stories in depth. His goal is that you’ll treat this book—and our conversations—less like a textbook and more like a mirror. “I hope [it] prompts you, as writing it did for me, to examine your own relationship to your job.”
More About Simone: Simone Stolzoff is an independent journalist and consultant from San Francisco. A former design lead at the global innovation firm IDEO, he regularly works with leaders—from the Surgeon General of the United States to the Chief Talent Officer at Google—on how to make the workplace more human-centered. His feature writing on the intersection of labor and Silicon Valley has appeared in The Atlantic, WIRED, The San Francisco Chronicle, and numerous other publications. Today we’re talking about his new book, The Good Enough Job: Reclaiming Life from Work.
🌟 3 Key Takeaways
- If all your needs were met, what would you do with your life? How might that inform the work you do to get paid versus the activities that nourish your spirit?
- Michael Norton at HBR asks millionaires two questions: How happy are you on a scale of 1 to 10? And how much more money would you need to get to a 10 out of 10? Regardless of whether people had $1 or $2 or $5 million, respondents all answered the same way: that they’ll be happier when they have two to three times more money than they have now.
- You may still experience grief even if you’re making a decision that can be a better path for you in the future.
✅ Try This Next
Consider how your identity is shaped by the people you are surrounded by. Find communities that can reinforce an identity of yours beyond the commercial value you contribute to the world, beyond your professional life. What group/s can you join where what you do for work doesn’t matter to them at all? (Think intramural sports or even time outside with pets :)
🔗 Resources Mentioned
- Simone on the web, IG, Twitter, LinkedIn
- Simone’s Substack: Simone Stolzoff
- Articles: NYT—Please Don’t Call My Job a Calling
📚 Books Mentioned
- The Good Enough Job: Reclaiming Life from Work by Simone Stolzoff
- The Pathless Path: Imagining a New Story for Work and Life by Paul Millerd
- Free Time: Lose the Busywork, Love Your Business
- Pivot: The Only Move That Matters Is Your Next One
- Life After College
🎧 Related Episodes
- Pivot x RadReads: Conversations with Khe Hy (Spotify Playlist)
- Pivot: 341: Pivoting From Prestigious Consulting Jobs To The Pathless Path With Paul Millerd
- 321: ChatGPT as Universal Intern and Excellent Advice for Living with Kevin Kelly
- Free Time: 203: 🎢 Riding the Emotional Rollercoaster of Launching with Natalie Lue
- 205: Why Paul Millerd Turned Down a $200K Two-Book Traditional Publishing Deal
❤️ Enjoying the show? I'd be grateful for a rating and/or review! Even better?
As relationship expert Ester Perel says, “Too many people bring the best of themselves to work, and bring the leftovers home.” This is one of several notions that sparked today’s guest, Simone Stolzoff, to reconsider his relationship to work. We’re talking about his unique approach to researching his new book, The Good Enough Job, interviewing over 100 primarily white-collar workers, but only featuring nine stories in depth. His goal is that you’ll treat this book—and our conversations—less like a textbook and more like a mirror. “I hope [it] prompts you, as writing it did for me, to examine your own relationship to your job.”
More About Simone: Simone Stolzoff is an independent journalist and consultant from San Francisco. A former design lead at the global innovation firm IDEO, he regularly works with leaders—from the Surgeon General of the United States to the Chief Talent Officer at Google—on how to make the workplace more human-centered. His feature writing on the intersection of labor and Silicon Valley has appeared in The Atlantic, WIRED, The San Francisco Chronicle, and numerous other publications. Today we’re talking about his new book, The Good Enough Job: Reclaiming Life from Work.
🌟 3 Key Takeaways
- If all your needs were met, what would you do with your life? How might that inform the work you do to get paid versus the activities that nourish your spirit?
- Michael Norton at HBR asks millionaires two questions: How happy are you on a scale of 1 to 10? And how much more money would you need to get to a 10 out of 10? Regardless of whether people had $1 or $2 or $5 million, respondents all answered the same way: that they’ll be happier when they have two to three times more money than they have now.
- You may still experience grief even if you’re making a decision that can be a better path for you in the future.
✅ Try This Next
Consider how your identity is shaped by the people you are surrounded by. Find communities that can reinforce an identity of yours beyond the commercial value you contribute to the world, beyond your professional life. What group/s can you join where what you do for work doesn’t matter to them at all? (Think intramural sports or even time outside with pets :)
🔗 Resources Mentioned
- Simone on the web, IG, Twitter, LinkedIn
- Simone’s Substack: Simone Stolzoff
- Articles: NYT—Please Don’t Call My Job a Calling
📚 Books Mentioned
- The Good Enough Job: Reclaiming Life from Work by Simone Stolzoff
- The Pathless Path: Imagining a New Story for Work and Life by Paul Millerd
- Free Time: Lose the Busywork, Love Your Business
- Pivot: The Only Move That Matters Is Your Next One
- Life After College
🎧 Related Episodes
- Pivot x RadReads: Conversations with Khe Hy (Spotify Playlist)
- Pivot: 341: Pivoting From Prestigious Consulting Jobs To The Pathless Path With Paul Millerd
- 321: ChatGPT as Universal Intern and Excellent Advice for Living with Kevin Kelly
- Free Time: 203: 🎢 Riding the Emotional Rollercoaster of Launching with Natalie Lue
- 205: Why Paul Millerd Turned Down a $200K Two-Book Traditional Publishing Deal
❤️ Enjoying the show? I'd be grateful for a rating and/or review! Even better?
Previous Episode

348: How to Experience More Everyday Awe with Dacher Keltner
“The evolution of our species built into our brains and bodies an emotion, our species-defining passion, that enables us to wonder together about the great questions of living.”
That’s just one of many illuminating conclusions that researcher Dr. Dacher Keltner discovered in his scientific studies of awe. In this conversation, you’ll learn about the eight wonders of life, how to experience more everyday awe (and take yourself on awe walks), and what’s behind our current crisis of meaning.
As Dacher writes, “Our experiences of awe hint at faint answers to these perennial questions and move us to wander toward the mysteries and wonders of life.”
More About Dacher: Dr. Dacher Keltner is a professor of psychology at the University of California, Berkeley and the faculty director of the UC Berkeley Greater Good Science Center. A renowned expert in the biological and evolutionary origins of human emotion, Dr. Keltner studies the science of compassion, awe, love, and beauty, and how emotions shape our moral intuition. His research interests also span issues of power, status, inequality, and social class.
He is the author of the best-selling book Born to Be Good: The Science of a Meaningful Life and of The Compassionate Instinct, and today we are talking about his most recent book, AWE: The New Science of Everyday Wonder and How It Can Transform Your Life. Dacher is also the host of the award-winning podcast, The Science of Happiness.
🌟 3 Key Takeaways
- 8 wonders of life: moral beauty (the strength, courage, overcoming, and kindness of others); collective effervescence; nature; music; visual design; mysticism (spiritual and religious); stories of life and death; and epiphanies.
- Everyday awe: In our daily lives, we most frequently feel awe in encounters with moral beauty, and secondarily in nature and in experiences with music, art, and film.
- The big idea of awe: We are part of systems larger than the self. “Awe is about knowing, sensing, seeing and understanding fundamental truths, and leads to epiphanies across the eight wonders of life—transforming how we see the essential nature of the world.”
✅ Try This Next—Go on an Awe Walk:
- Tap into your childlike sense of wonder. Try to approach what you see with fresh eyes, imagining that you're seeing it for the first time. Take a moment in each walk to take in the vastness of things, for example in looking at a panoramic view or up close at the detail of a leaf or flower.
- Go somewhere new. Each week, try to choose a new location. You're more likely to feel awe in a novel environment where the sights and sounds are unexpected and unfamiliar to you. That said, some places never seem to get old, so there's nothing wrong with revisiting your favorite spots if you find that they consistently fill you with awe. The key is to recognize new features of the same old place.
- What’s mysterious around me? What’s the deeper story of what I’m perceiving?
🔗 Resources Mentioned
- Dacher on the web and LinkedIn (No Twitter and IG accounts)
- Video: The Diary of a CEO—The “Happy Life” Scientist (YouTube Video)
- Articles: NYT—How a Bit of Awe Can Improve Your Health
📚 Books Mentioned
- AWE: The New Science of Everyday Wonder and How It Can Transform Your Life
- The Varieties of Religious Experience by William James
- Red-Tails in Love by Marie Winn
- Free Time: Lose the Busywork, Love Your Business
- Pivot: The Only Move That Matters Is Your Next One
- Life After College
🎧 Related Episodes
- Dacher’s podcast:
Next Episode

350: The Simple Yet Powerful Three-Word Phrase that Shifts My Day
A short-and-sweet solo episode for you today on the three little words that instantly shift my mood from heavy obligation toward light, joyful action. Every time I remember to say this phrase, it’s like opening a window in a stuffy room—suddenly, there's space, air, and light.
🌟 3 Key Takeaways
- See tasks as opportunities, not burdens: What within them are you grateful for? What are your reasons for doing them in the first place?
- This phrase helps with three things: stress reduction—viewing tasks as opportunities lowers anxiety; increased motivation—hen we feel fortunate to do something, we're more energized to do it; and a happiness boost, as gratitude is a direct path to joy.
- **If there is no possible way to shift, maybe it is time to stop doing that thing altogether. If certain activities are draining you, dragging you down, say no. If you can’t yet say no—at least not now—find the reasons you are sticking with them, and keep those top of mind.
✅ Try This Next
What’s one thing you’re dreading, procrastinating on, or avoiding this week? What happens when you shift your mindset from “I have to” toward “I get to”? Does anything feel lighter or freer?
🔗 Resources Mentioned
- Articles: ✍️ Connect with me on Substack
📚 Books Mentioned
- Free Time: Lose the Busywork, Love Your Business
- Pivot: The Only Move That Matters Is Your Next One
- Life After College
🎧 Related Episodes
- Pivot: 348: How to Experience More Everyday Awe with Dacher Keltner
- 312: Are You Future-Tripping?
- 316: “Don’t Suffer Twice”
- 154: Two-Month Report from the Puppy (and People!) Training Trenches
- Free Time: 029: Funded By Source with Ksenia Avdulova
- 154: The Hard No
- 174: What Book Marketing has to do with Glass Blowing: Reflecting on Free Time’s 1-Year Bookiversary 🥂
- 120: Transform Your To-Do List into a Results List — Leanne’s Favorite Time-Saving System
- 090: Paying for Consistency and Accountability
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