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In this episode, Simone Stolzoff explores why the need for certainty is holding you back and how learning to live with uncertainty can lead to greater resilience, better decisions, deeper relationships, and a more meaningful life. Drawing from psychology, neuroscience, philosophy, and his own deeply personal experiences, Simone explains why our brains crave certainty, why that instinct often fuels anxiety and overthinking, and how embracing the unknown can become a source of growth rather than fear. If you've ever found yourself stuck waiting for the “right” answer before moving forward, this conversation offers a wiser—and more freeing—way to navigate life's inevitable uncertainty. Free Guide: Outsmart the Hidden Saboteurs of Self-Control. What's been holding you back lately? In this free guide, Eric shares the six common saboteurs that quietly derail our best intentions—like autopilot behavior, self-doubt, and emotional escapism—and offers practical strategies to help you regain control and move forward. Download your free copy at oneyoufeed.net/ebook. Key Takeaways: The concept of uncertainty and its discomfort in a world that demands quick answers. The parable of the two wolves and its relation to embracing uncertainty. Biological and evolutionary reasons for the discomfort associated with uncertainty. The impact of technology and instant answers on our tolerance for uncertainty. Psychological traps related to certainty: comfort, hubris, and control. The importance of reframing uncertainty as a source of possibility and growth. Decision-making strategies and insights from experts on navigating uncertainty. The role of doubt as a positive force in decision-making and personal growth. The balance between exploration and exploitation in life choices. Personal experiences with uncertainty and their impact on life perspectives. For full show notes, click here! If you enjoyed this conversation with Simone Stolzoff, check out these other episodes: Embracing Uncertainty: The Key to True Intimacy and Connection in a Chaotic World with Prince EA How to Embrace Change for an Authentic Life with Najwa Zebian This episode is sponsored by: Quince: Refresh your wardrobe with Quince by going to Quince.com/feed for free shipping and 365-day returns. Now available in Canada, too. Shopify – The commerce platform that helps you build, grow, and manage your business all in one place. Start your $1/month trial at shopify.com/feed. David Protein bars deliver up to 28g of protein for just 150 calories—without sacrificing taste! For a limited time, our listeners can receive this special deal: buy 4 cartons and get the 5th free when you go to www.davidprotein.com/FEED Alma has a directory of 20,000 therapists with different specialities, life experiences, and identities, and 99% of them take insurance. Visit helloalma.com to learn more! Talkiatry connects you with licensed psychiatrists for personalized, evidence-based mental health care, all online and covered by most major insurance plans. To get matched with an in-network psychiatrist in just a few minutes, visit Talkiatry.com/FEED. Tiny Health‘s at-home gut health test provides science-backed insights into your microbiome, along with personalized recommendations to help you improve your digestion, energy, and overall well-being. Get $50 off your first test kit at tinyhealth.com/FEED Learn more about your ad choices. Visit megaphone.fm/adchoices
Think about the last time you couldn't make up your mind about a big decision. Maybe you made a pro-and-con list, read every review, and talked it through with other people — and still couldn't decide. We tell ourselves that just a little more information will finally bring the certainty we need to choose. But my guest today says more research can fuel your anxiety and the certainty we're chasing doesn't actually exist. If you're indecisive, you overthink every choice, or you freeze up for fear of making the wrong decision, this episode is for you. My guest is Simone Stolzoff, a journalist and the author of The Good Enough Job. His new book, How to Not Know, is all about making hard decisions and learning to tolerate uncertainty. In this episode on decision-making and uncertainty, we discuss: Why our tolerance for uncertainty is shrinking at the exact moment the world is becoming more uncertain The two surprising ways people dodge hard decisions — and why impulsive decision-makers may be just as avoidant as obsessive researchers The study that showed we'd rather face a guaranteed painful event than sit with the uncertainty of one Why the best leaders aren't "know-it-alls" but "learn-it-alls" The Only Option Test — a fast way to break a stuck decision when both choices look equally good The Chinese farmer parable, and why "maybe yes, maybe no" is one of the most freeing things you can tell yourself The line from an oncology doctor that can change how you face anything uncertain in your future The Therapist's Take: my top three strategies for making decisions and living with uncertainty, starting today Related Episodes 60 — Face Fear and Embrace Uncertainty So You Can Live a Good Life with Best-Selling Author Jonathan Fields 321 — How to Use Constraints to Spark Better Ideas, Make Faster Decisions, and Live With Less Regret With Bestselling Author David Epstein Links & Resources How to Not Know Connect with the Show Buy a copy of 13 Things Mentally Strong People Don't Do Connect with Amy on Instagram — @AmyMorinAuthor Visit my website — AmyMorinLCSW.com Sponsors Helix Sleep —Go to helixsleep.com/STRONGER to get 20% off sitewide AirDoctor — Head to AirDoctorPro.com and use promo code STRONGER to get UP TO $300 off today! One Skin — Go to oneskin.co/STRONGER and use code stronger to get up to 30% off your first 3 subscription orders Quince — Go to Quince.com/stronger for free shipping on your order and 365 day returns! Flamingo — Get a $7 starter set at ShopFlamingo.com/STRONGER Subscribe to Mentally Stronger Premium for exclusive content like weekly bonus episodes, mental strength challenges, and office hours with me. Learn more about your ad choices. Visit megaphone.fm/adchoices
HOW TO NOT KNOW: The Value of Uncertainty In A World That Demands Answers, by journalist and teacher Simone Stolzoff, looks at the biases that we lean on to predict the future and the unexpected benefits of surrendering control. A former design lead at the global innovation firm IDEO, Simone Stolzoff’s work has been featured in The New York Times, The Atlantic, National Geographic and many others.See omnystudio.com/listener for privacy information.
From betting apps to AI models, prediction has become big business. This hour, why we're so drawn to certainty, and what happens when we mistake forecasts for facts. Guests include professor Brendan Dwyer, philosopher Carissa Véliz, and journalist Simone Stolzoff.TED Radio Hour+ listeners now get access to bonus episodes, with more ideas from TED speakers and deeper conversations with Manoush. By signing up for Plus, you directly support our work and public media, so all your episodes (like this one!) come to you without sponsor breaks. Learn more at plus.npr.org/ted.See pcm.adswizz.com for information about our collection and use of personal data for sponsorship and to manage your podcast sponsorship preferences.NPR Privacy Policy
Today on The Gist, President Trump says he “couldn't care less” whether Iran negotiations are over because, frankly, they've gotten “a little boring.” Mike takes him at his word, which is exactly the problem: when the Strait of Hormuz, gas prices, and the possibility of war are on the table, boredom is not a diplomatic strategy. Then, journalist Simone Stolzoff joins to discuss his new book, How Not to Know: The Value of Uncertainty in a World That Demands Answers. Stolzoff explains why human brains crave prediction, why the internet has made us worse at sitting with ambiguity, and why certainty can become a trap, whether it comes from cults, algorithms, productivity culture, or the false promise that every answer is just one search away. Mike presses him on whether learning to “let go” is a problem of abundance, and whether books about work, anxiety, and uncertainty mostly speak to people whose material problems have already been solved. Produced by Corey Wara Edited by Geoff Craig Do you have questions or comments, or just want to say hello? Email us at thegist@mikepesca.com For full Pesca content and updates, check out our website at https://www.mikepesca.com/ For ad-free content or to become a Pesca Plus subscriber, check out https://subscribe.mikepesca.com/ For Mike's daily takes on Substack, subscribe to The Gist List https://mikepesca.substack.com/ Follow us on Social Media: YouTube https://www.youtube.com/channel/UC4_bh0wHgk2YfpKf4rg40_g Instagram https://www.instagram.com/pescagist/ X https://x.com/pescami TikTok https://www.tiktok.com/@pescagist To advertise on the show, contact sales@amplitudemediapartners.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
Most of the financial decisions keeping you up at night are two-way doors. You can change them. You can undo them. The real one-way doors -- the decisions that actually lock you in -- are rarer than you think, and the problem is we're spending the same emotional energy on both. Joe, OG, Paula Pant, and Jesse Cramer take Simone Stolzoff's uncertainty framework from Wednesday and run it straight through real financial life: career changes, portfolio risk, entrepreneurial pivots, and the moment you finally flip the kill switch on something that isn't working.What You'll Walk Away WithThe one-way door versus two-way door framework applied to real decisions -- and why automating your savings contributions is the most underrated version of this ideaJesse's anchor: why life insurance changed everything about how he sleeps at night now that there are passengers in the car with himPaula's anchor: why avoiding debt entirely is the entrepreneurial version of keeping your burn rate survivable when revenue gets unpredictableOG's anchor: long-term belief in human ingenuity as a financial strategy -- and why short-term geopolitical noise is actually an opportunity for investors who aren't panickingWhy selling assets in a taxable brokerage account to cover business payroll is a two-way door -- until enough time passes and it quietly becomes a one-way doorThe kill criteria conversation: how Jesse built an 18-to-24-month runway into his career change before he ever made the leapWhy the Everest turnaround time is the most important financial planning concept most people have never applied to their own goalsOG's client story: when the right risk tolerance isn't the mathematically correct one -- it's the one that lets you sleep at night without calling your advisorPaula on the pivot strategy: keep iterating the broad direction until you find the product-market fit, because the version that works might look nothing like what you started withWhy a career shift becomes more of a one-way door the longer you wait -- and what Rocky Mark's electrical engineer to content creator question reveals about timingWhy This Matters NowThe worst financial decisions happen when people treat reversible choices as permanent ones and freeze -- or treat permanent choices as reversible and act too fast. This episode gives you a framework for telling the difference before the emotion hits, which is the only time it actually helps.From the BasementJoe, OG, Paula Pant, and Jesse Cramer take Simone Stolzoff's Wednesday framework and apply it to the messy real world of careers, portfolios, entrepreneurship, and retirement identity. The trivia competition takes a dramatic turn when OG margin calls Jesse on a Mount Everest question -- and the full margin call rule set gets read aloud for the first time in recorded history after Dottie in Wichita makes a call nobody wanted to receive. Jesse wins the point. OG loses one. The coalition closes the gap.Resources MentionedAfford Anything podcast -- Paula Pant; Joe joins most Tuesdays for listener Q&A; youtube.com/affordanythingPersonal Finance for Long-Term Investors -- Jesse Cramer's podcast; current series: 14 biggest risks in retirement, Charlie Munger-inspired inversion frameworkStacking Benjamins Wednesday episode -- "Why Uncertainty Is an Opportunity" with Simone Stolzoff; stackingbenjamins.comStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201OG financial planning calendar -- stackingbenjamins.com/ogStacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
The five highest global uncertainty readings since the 1980s have all occurred in the last five years. And yet the answer Wall Street keeps selling -- products that promise upside without downside -- is mathematically impossible and provably underperforms over time. Simone Stolzoff, author of How to Not Know, spent years studying how people, companies, and investors navigate uncertainty well. His findings are the opposite of what the financial industry is selling you right now.What You'll Walk Away WithWhy our tolerance for uncertainty is declining -- and the specific role smartphones and real-time data have played in making investors more anxious and worse at decision-makingThe anchor framework: how certainty in some areas of your life makes it dramatically easier to hold uncertainty in others -- and what that means for how you build a financial planThe Slack origin story -- how a gaming company at the peak of its success chose to shut down and pivot into the unknown, and what that teaches about staying open to what might emergeWhy Warren Buffett and the best venture capitalists actively seek uncertainty -- and how confusion between uncertainty and danger costs most investors real moneyThe kill criteria concept borrowed from mountain climbing -- and how pre-committing to rules before the emotion hits is the only reliable way to prevent catastrophic decisionsOne-way doors versus two-way doors: the Jeff Bezos framework for knowing when to agonize over a decision and when to just actWhy buffer ETFs are mathematically required to underperform broad index funds over time -- and the one question that exposes every "downside protection" pitch instantlyOG's case for looking at your portfolio as rarely as possible -- and the surprising thing that happened when he checked his mortgage balance after months awayWhy building a financial plan around your actual goals makes the daily market headlines genuinely irrelevant -- not as a coping strategy, but as a logical outcomeKathy's story: what a special education teacher who maxed her Roth IRA every year from 1998 to 2024 has in her account todayWhy This Matters NowMarkets will always be uncertain. Headlines will always be alarming. The question isn't how to make that stop -- it's how to build a life and a plan sturdy enough that it doesn't matter. This episode is the clearest case we've made for why your financial plan is more important than your portfolio, and why the two are not the same thing.From the BasementSimone Stolzoff joins Joe and OG to unpack the psychology of uncertainty -- including a couple who took a year apart to figure out if they wanted to stay married, a software engineer who programmed an app to make all his life decisions, and the monk who said not knowing is the most intimate thing of all. The Investment News headline about clients wanting "headline-proof portfolios" gives OG a full platform to explain why buffer ETFs are a product designed for the advisor's book of business, not your retirement. Doug arrives with Wild Bill Hickok trivia. Kathy from the community sends a note that should be required reading for every Gen X stacker who thinks they're behind.Resources MentionedHow to Not Know: The Value of Uncertainty in a World That Demands Answers by Simone Stolzoff -- available wherever books are sold; early readers receive an invitation to an exclusive event with Michael LewisSimone Stolzoff -- simonestolzoff.comInvestment News -- "Advisors say more clients are seeking to headline-proof their portfolios" by Greg Greenberg; linked at stackingbenjamins.comStacking Benjamins Episode 1840 -- "Why 67% of Americans Fear Running Out of Money More Than Dying"; stackingbenjamins.comStacking Benjamins Vault -- stackingbenjamins.com/vaultStacking Benjamins Newsletter (The 201) -- stackingbenjamins.com/201Stacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
If one things for certain, there's a lot of uncertainty in dating, relationships, and the world right now. We're joined by journalist and author Simone Stolzoff to talk about why people struggle so much with uncertainty and how this shows up in our romantic relationships. We're discussing the three traps that make us believe there's certainty even when there isn't, ways to build an uncertainty tolerance to apply to dating situations and relationships, and how to reframe 'not knowing' as something positive that sets us up for discovery to find the types of relationships and opportunities beyond what we thought was even possible. To learn more about Simone Stolzofff go to https://simonestolzoff.com. Get his new book 'How To Not Know: The Value of Uncertainty in a World that Demands Answers' wherever books are sold.----Take our Dating Archetypes quiz: https://howtobedateable.com/Read our book: How To Be Dateable: The Essential Guide To Finding Your Person and Falling in Love: https://howtobedateable.com/Try the Dateable AI Dating Coach: Get personalized advice trained on our years of podcast episodes, courses and frameworks: https://studio.com/dateableFollow us @dateablepodcast, @juliekrafchick and @nonplatonic. Check out our website for more content. Also listen to our other podcasts The Psychology of Relationships and Exit Interview available on Apple Podcasts, Spotify, or wherever you get your podcasts.WE WROTE A BOOK! HOW TO BE DATEABLE (Simon & Schuster) is available now: https://howtobedateable.com/ Want to remove distractions from your dates? Download Brick and get 10% off at https://www.getbrick.app/DATEABLEOur Sponsors:* Avocado Green Mattress: Check out their mattress and furniture sale: https://avocadogreenmattress.com/DATEABLE* Get Rain of Shadows and Endings wherever books are sold or at Kensington Publishing https://www.kensingtonbooks.com* Quince: Get free shipping and 365 day returns at https://quince.com/dateable* Ruggable: Get 10% off your first order, sitewide, with promo code DATEABLE at https://ruggable.comAdvertising Inquiries: https://redcircle.com/brandsPrivacy & Opt-Out: https://redcircle.com/privacy
Welcome to episode #1037 of Thinking With Mitch Joel (formerly Six Pixels of Separation). At a moment when certainty has become both a cultural obsession and a commercial product, Simone Stolzoff is asking a far more uncomfortable question: what if the real skill is learning how to live without it? A journalist whose work has appeared in publications like The Atlantic and author of the bestselling book The Good Enough Job, Simo has built his work around examining the hidden psychological contracts shaping modern life… especially our increasingly tangled relationship with work, ambition and identity. His new book, How to Not Know - The Value of Uncertainty in a World that Demands Answers, pushes that exploration even further, arguing that many of the anxieties defining modern life stem not from uncertainty itself… but from our declining ability to tolerate it. In this conversation, Simo explores why uncertainty has become so psychologically destabilizing in an era where information is infinite, prediction is constant and every question seems one search query away from an answer. He discusses the paradox of modern life: despite unprecedented prosperity, connectivity and opportunity, people feel increasingly fragile, overwhelmed and fearful of ambiguity. Simo explains how uncertainty once served an important evolutionary purpose, but has become maladaptive in a culture obsessed with optimization, certainty and control. The conversation moves through entrepreneurship, identity, politics, AI, climate anxiety, relationships and creativity… all connected by the tension between our desire for certainty and the reality that much of life remains fundamentally unknowable. Simo argues that uncertainty is not a flaw in the system… it is the birthplace of possibility, growth and reinvention. Along the way, we discuss Brian Eno, venture capital, the psychology of risk, the danger of false certainty in modern discourse, and why action itself is often the antidote to anxiety. What emerges is not a conversation about having the answers… but about developing the resilience, humility and imagination to move forward without them. Enjoy the conversation… Running time: 57:55. Hello from beautiful Montreal. Listen and subscribe over at Apple Podcasts. Listen and subscribe over at Spotify. Please visit and leave comments on the blog - Thinking With Mitch Joel. Feel free to connect to me directly on LinkedIn. Check out ThinkersOne. Here is my conversation with Simone Stolzoff. How To Not Know - The Value of Uncertainty in a World that Demands Answers. The Good Enough Job. Subscribe to Simo's newsletter. Follow Simo on Instagram. Follow Simo on LinkedIn. Chapters: (00:00) - Introduction to Simone Stolzoff. (01:45) - The Intersection of Identity and Career. (03:50) - Embracing Uncertainty in Life and Work. (10:56) - Cultural Perspectives on Risk and Entrepreneurship. (15:50) - The Paradox of Comfort and Growth. (18:49) - Building Tolerance for Uncertainty. (22:33) - Macro Perspectives on Progress and Uncertainty. (27:23) - Navigating Opportunities in an Unstable Job Market. (33:07) - The Role of Geography in Relationships and Opportunities. (36:43) - Age Bias and Risk Aversion. (41:08) - Resilience in the Face of Uncertainty. (50:02) - Closing Thoughts on Rigidity and Acceptance.
Have you ever found yourself paralyzed by a major life decision, desperately wishing you just had the right answer? In this episode of the show, I sit down with author and journalist Simone Stolzoff to dive into a topic we all struggle with: our deep aversion to the unknown. Simone shares the inspiration behind his latest book, How to Not Know: The Value of Uncertainty in a World That Demands Answers, and breaks down how our hyper-connected world has ruined our ability to sit with ambiguity. If you're tired of overthinking, catastrophizing, or trying to control the future, this episode is exactly what you need to expand your window of tolerance and reclaim your peace. Read the show notes for today's episode at terricole.com/832
Simone Stolzoff's new book: How to Not Know - https://amzn.to/420WLhp (affiliate) Uncertainty is everywhere right now. From economic shifts and global conflict to career changes and parenting decisions, many of us are craving answers in a world that feels increasingly unpredictable. In this episode, we sit down with author and journalist Simone Stolzoff to discuss how we can become more comfortable with uncertainty instead of constantly trying to eliminate it. Simone shares insights from his new book, How to Not Know: The Value of Uncertainty in a World That Demands Answers, and explains why our obsession with certainty may actually be fueling anxiety. We discuss how technology has changed our tolerance for the unknown, why discomfort can lead to growth, and practical ways to build resilience in uncertain times. If you've been feeling overwhelmed by the future, this conversation will help you slow down, breathe deeper, and rethink your relationship with uncertainty. RESOURCES Own Your Time – Pre-order our first book today! MKM Coaching – Get 1-on-1 support with your family finance journey. Coast FIRE Calculator – Find out when you can slow down or stop investing for retirement. Mortgage Payoff Calculator – See how fast you can become mortgage free. RECOMMENDED RESOURCES (SPONSORS & AFFILIATES) Monarch Money – Best budget app for families & couples. Crew – HYSA banking built for families (Get an extra 0.5% APY with our partner link). GUEST RESOURCES Simone Stolzoff's new book: How to Not Know - https://amzn.to/420WLhp HOW WE MAKE MONEY + DISCLAIMER This show may contain affiliate links or links from our advertisers where we earn a commission, direct payment or products. Opinions are the creators alone. Information shared on this podcast is for entertainment purposes only and should not be considered as professional advice. Marriage Kids and Money (www.marriagekidsandmoney.com) is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to amazon.com. CREDITS Host: Andy Hill Editor: Johnny Sohl Podcast Support: Michelle Ahmed Learn more about your ad choices. Visit megaphone.fm/adchoices
We like to think the future can be figured out if we just gather enough information. Pick the right expert, read the right forecast, find the right framework, and the fog will lift. Simone Stolzoff argues that this impulse often works against us. In his new book How to Not Know, he makes the case for getting better at uncertainty—not as a slogan, and not as an excuse to believe nothing, but as a practical skill: knowing when to act without perfect information, when to distrust easy answers, when to revise your beliefs, and when uncertainty might point toward something worth discovering. The conversation covers why people cling to conspiracy theories, what cults offer that ordinary life does not, why experts are so bad at predicting the future, how the replication crisis changed psychology, what relationships teach us about irreversible choices, and why the unknown is not only frightening, but also where possibility begins. Simone Stolzoff is a San Francisco–based journalist and author. His work has appeared in The New York Times, The Atlantic, and on the TED stage. He is a graduate of Stanford University and the University of Pennsylvania. His debut book, The Good Enough Job, has been translated into more than a dozen languages. His new book is How to Not Know: The Value of Uncertainty in a World That Demands Answers.
Though our lives are filled with uncertainty, we're less tolerant of it than ever, says journalist Simone Stolzoff, author of the new book “How to Not Know: The Value of Uncertainty in a World that Demands Answers.” Surrounded by prediction markets, statistics and the world's knowledge on our phones, we think we should always be certain – in who we are, what we believe and what the “right” choice is. But Stolzoff says that accepting and even appreciating uncertainty can help us be more tolerant, humble and ready to take on life's curveballs. Guests: Simone Stolzoff, journalist and author, "How to Not Know: The Value of Uncertainty in a World that Demands Answers" and "The Good Enough Job: Reclaiming Life from Work" Learn more about your ad choices. Visit megaphone.fm/adchoices
You can run from uncertainty, but you can't hide. The thing to do, says Simone Stolzoff, to develop comfort with ambiguity and build tolerance for the unknown. His new book is How to Not Know: The Value of Uncertainty in a World that Demands Answers. Granola ➡️ If meetings are eating up your day, Granola is a no-brainer. You can try it totally free for three months. Just head to granola.ai/idea Incogni ➡️ Protect your personal information online and get an exclusive 60% off an annual plan at incogni.com/nbi Quince ➡️ Refresh your spring wardrobe and get free shipping and 365-day returns at quince.com/nbi Shopify ➡️ Launch your business for just $1/month. Start selling today at shopify.com/nbi
In a world obsessed with answers, author Simone Stolzoff makes the case that having uncertainty isn't the problem, and that the power of not knowing may be the solution in his new book, "How to Not Know: The Value of Uncertainty in a World that Demands Answers."
Simone Stolzoff is a journalist, author, and workplace expert who joins Max to discuss his new book How to Not Know and why learning to tolerate uncertainty may be one of the most important skills for mental health, resilience, creativity, and success in the modern world.15 Daily Steps to Lose Weight and Prevent Disease PDF: https://bit.ly/46XTn8f - Get my FREE eBook now!Subscribe to The Genius Life on YouTube! - http://youtube.com/maxlugavereWatch my new documentary Little Empty Boxes - https://www.maxlugavere.com/filmThis episode is proudly sponsored by:Cozy Earth makes some of the most comfortable bedding and loungewear I've ever used—breathable, temperature-regulating, and genuinely luxurious. Head to cozyearth.com and use code GENIUS to get up to 20% off.Our Place makes beautiful, toxin-free home cookware, free of PFAS and Teflon! http://fromourplace.com and use code MAX for 10% off, site-wide!
Did you know our brains are wired to fear uncertainty MORE than suffering? The good news is that in the same way you can build muscles, you can build your tolerance for the unknown. When you're comfortable with uncertainty, you'll be less anxious, go after more opportunities, find more success, and make better decisions. And that is exactly what you're going to learn how to do today. My guest is Simone Stolzoff, a famous journalist and best-selling author, who dives into the learnings and stories from his new book How To Not Know: The Value of Uncertainty in a World That Demands Answers.
If financial uncertainty is keeping you awake at night, this episode is for you. Author and journalist Simone Stolzoff joins Jean to talk about his new book, How To Not Know: The Value of Uncertainty in a World That Demands Answers, and why learning to sit with the unknown might be the most powerful financial skill you can develop right now. And in this week's Mailbag, Jean is joined by Lacy Garcia, founder and CEO of Willow, to help three listeners navigate inflection points in their lives: how to start dividing shared assets before a divorce is filed, what to do with your 401(k) after a layoff, and how to think about a lump-sum inheritance without letting fear or emotion drive the decision. Resources mentioned in this episode: The Good Enough Job by Simone Stolzoff Hanna Horvath, Your Brain on Money on Substack The Forever Paycheck by Jean Chatzky — available for pre-order now Subscribe to the HerMoney newsletter Ready to connect with a fiduciary advisor who's the right fit for you? Find one at hermoney.com/findanadvisor. Learn more about your ad choices. Visit megaphone.fm/adchoices
Simone Stolzoff, author of How to Not Know, shares tips for building our tolerance for uncertaintySee omnystudio.com/listener for privacy information.
What happens when our biological need for certainty clashes with an increasingly unpredictable world? Simone Stolzoff, author of How to Not Know, joins host Zachary Karabell to discuss why our modern intolerance for uncertainty is fueling a global anxiety crisis. Rather than seeing the unknown as a threat, Stolzoff argues that uncertainty is the fundamental birthplace of scientific breakthroughs, original art, and human progress. Stolzoff and Karabell explore how to navigate everything from the climate crisis and the AI revolution to high-stakes parenting and career choices through the framework that the false certainty we cling to might actually be detrimental to our success. While acknowledging the hard truths of today's world, Stolzoff explains why "action absorbs anxiety" and makes the case for diversifying our identities so we remain adaptable in the face of an unwritten future. What Could Go Right? is produced by The Progress Network and Kaleidoscope. For transcripts, to join the newsletter, and for more information, visit: theprogressnetwork.org Subscribe to our (FREE) Substack newsletter: https://theprogressnetwork.org/newsletter/ Watch the podcast on YouTube: / theprogressnetwork Follow us on X, Instagram, Facebook, TikTok: @progressntwrk Subscribe to Zachary's Substack: www.edgyoptimist.substack.com/
Why does not knowing feel worse than bad news? How to Not Know author Simone Stolzoff shows us how to make uncertainty work for us, not against us.Full show notes and resources can be found here: jordanharbinger.com/1326What We Discuss with Simone Stolzoff:Certainty feels like wisdom but often isn't — Phil Tetlock found the average expert predicting the future is about as accurate as a dart-throwing chimpanzee, yet we keep mistaking confidence for competence and rewarding the loudest voice in the room.Our brains are wired for the savanna, not the spreadsheet. The same alarm bells that once warned us about rustling bushes now fire over phone storage decisions, leaving us anxious about choices that have almost nothing to do with survival.We hate ambiguity so much we'd choose guaranteed pain over uncertainty — one study found people facing a 50 percent chance of a shock felt more stressed than those facing 100 percent. Not knowing whether you'll lose your job hurts as much as actually losing it.Intolerance for uncertainty traps us in mediocre jobs, mediocre relationships, and mediocre lives. The "safe" choice quietly becomes the costly one, because the breakthroughs — entrepreneurial, creative, personal — all live on the other side of not knowing.Treat uncertainty tolerance as a muscle you can train. Take a new route to work, order the unfamiliar dish, run small experiments, write down your predictions, and trust your future self to handle future problems — that version of you will have more context than the one worrying today.And much more...And if you're still game to support us, please leave a review here — even one sentence helps! Sign up for Six-Minute Networking — our free networking and relationship development mini course — at jordanharbinger.com/course!Subscribe to our once-a-week Wee Bit Wiser newsletter today and start filling your Wednesdays with wisdom!Do you even Reddit, bro? Join us at r/JordanHarbinger!This Episode Is Brought To You By Our Fine Sponsors: Lufthansa Allegris: Go to Lufthansa.com and search for "Allegris" to learn moreThe Cybersecurity Tapes: Listen here: thecybersecuritytapes.comBoll & Branch: 15% off first set of sheets: bollandbranch.com, code JORDANAT&T: Get an iPhone 17 Pro for $0: att.com/iphone or visit an AT&T store for detailsProgressive Insurance: Free online quote: progressive.comSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
This week, we explore two forces that shape every creative journey: constraint and uncertainty. Drawing on the remarkable artistic reinventions of Hokusai, we look at how creative legends transitioned from running from the box to thriving within it—and how that same process plays out in creative work today.Our first guest, David Epstein, author of Inside the Box, systematically dismantles the myth of the blank canvas and shows why true creative breakthroughs happen inside carefully constructed boundaries. He shares frameworks used by artistic innovators and practical strategies for leaders and teams to define the right limits—especially in an era of generative AI and limitless toolsets.We then talk with Simone Stolzoff, whose book How Not to Know tackles the fog of uncertainty head-on. He makes the case that tolerating, and even harnessing, uncertainty is not a liability but the lifeblood of all meaningful creative work. Together, David and Simone reveal why “embracing the box” and “rowing in the fog” are not problems to solve, but the permanent address of anyone doing real creative work.Five Key LearningsIntentional Constraints Fuel Creativity: Constraints are not the enemy; they're the engine. Strategic limits—on format, palette, or process—block the most familiar solutions and force genuinely new connections.Define the Boundaries Early: Projects that begin with rapid execution but no clear boundaries almost always bog down. Slow, deliberate thinking at the outset (setting priorities and constraints) leads to faster, more focused execution.Constraint is not Suffocation—It's Clarity: The most productive creative environments, whether in art, business, or writing, use narrow briefs and paired constraints to drive original outcomes.Our Tolerance for Uncertainty Is Eroding: As answers become more instantly available, we lose the ability to sit with the unknown. Microdosing uncertainty—through small experiments and unfamiliar choices—helps rebuild that vital tolerance.Progress is Acting in the Fog: The work that matters is rarely created in total freedom or certainty. Leaders who admit what they don't know and take action anyway (with humility and open curiosity) model the mental flexibility required to innovate.Get full interviews and bonus content for free! Just join the list at DailyCreativePlus.com.Mentioned in this episode:The Brave Habit is available nowMy new book will help you make bravery a habit in your life, your leadership, and your work. Discover how to develop the two qualities that lead to brave action: Optimistic Vision and Agency. Buy The Brave Habit wherever books are sold, or learn more at TheBraveHabit.com.Apply for Creative Leader Roundtable What if you had a space every month to sharpen your leadership edge without the fluff? The Creative Leader Roundtable is where smart, driven, creative leaders gather to exchange ideas, solve real challenges, and grow together. So if you lead a team of thinkers, makers, or dreamers, this is your lab. We're launching soon with a new group of leaders. So, if you're interested, check it out and apply at CreativeLeader.net.
The people who sound the most certain are often the most likely to be wrong. Simone Stolzoff makes the case for embracing uncertainty as a superpower in his new book How to Not Know. Then, in the second half, we revisit his earlier book The Good Enough Job — a reminder that a meaningful life can't be measured in output and hustle alone.
Most people think uncertainty is the problem. It's not. AJ sits down with journalist and author Simone Stolzoff to unpack why our obsession with certainty may actually be making us more anxious, avoidant, and stuck. From AI and career anxiety to relationships, decision-making, and control, Simone explains why experts are terrible at predicting the future — and why learning to tolerate uncertainty is one of the most important modern skills. This episode explores the three traps people fall into when facing uncertainty: comfort, control, and hubris — and how taking action, instead of endlessly consuming information, is what actually creates clarity. Chapters00:00 – Why we're addicted to certainty08:00 – Experts predict the future like dart-throwing chimps16:00 – The comfort trap and avoiding uncertainty24:00 – Why overthinking becomes emotional safety32:00 – Control, anxiety, and the illusion of certainty40:00 – Identity, values, and making hard decisions48:00 – Curiosity, future self-trust, and taking action A Word From Our Sponsors Stop being over looked and unlock your X-Factor today at unlockyourxfactor.com The very qualities that make you exceptional in your field are working against you socially. Visit the artofcharm.com/intel for a social intelligence assessment and discover exactly what's holding you back. If you've put off organizing your finances, Monarch is for you. Use code CHARM at monarch.com in your browser for half off your first year. Indulge in affordable luxury with Quince. Upgrade your wardrobe today at quince.com/charm for free shipping and hassle-free returns. Grow your way - with Headway! Get started at makeheadway.com/CHARM and use my code CHARM for 25% off. This year, skip breaking a sweat AND breaking the bank. Get your summer savings and shop premium wireless plans at mintmobile.com/charm Curious about your influence level? Get your Influence Index Score today! Take this 60-second quiz to find out how your influence stacks up against top performers at theartofcharm.com/influence. Episode resources: https://simonestolzoff.com https://www.amazon.com/How-Not-Know-Uncertainty-Demands/dp/1324089458 Check in with AJ and Johnny! AJ on LinkedIn Johnny on LinkedIn AJ on Instagram Johnny on Instagram The Art of Charm on Instagram The Art of Charm on YouTube The Art of Charm on TikTok uncertainty, decision making, anxiety, overthinking, AI anxiety, career uncertainty, self trust, emotional resilience, control, mindset, personal growth, relationships, ambiguity, action taking, uncertainty tolerance Learn more about your ad choices. Visit megaphone.fm/adchoices
Have you ever struggled with a problem—only to have the answer suddenly appear when you stopped trying? It feels almost like magic, but it's actually your brain working in a very specific way when you step back. https://drexel.edu/now/archive/2016/March/Insight_Correctness/ We all want to know what's going to happen next. But life doesn't work that way. In fact, the real challenge may not be uncertainty itself—but our growing discomfort with it. Simone Stolzoff, journalist and author of How to Not Know: The Value of Uncertainty in a World that Demands Answers (https://amzn.to/428rpWb), explains why we crave certainty, why that craving can make life harder, and how learning to tolerate—and even embrace—uncertainty can change the way you experience the world. You've probably heard that your health is shaped by both your genes and your lifestyle. But how much control do you really have? Are some outcomes unavoidable—or can your daily choices actually override genetic risk? Dr. Florence Comite, endocrinologist and expert in longevity and precision medicine, has spent decades studying how to optimize health at the individual level. In our conversation, she explains how genes influence your future, where they don't, and how understanding your personal biology can help you make smarter decisions to improve health and extend lifespan. She is author of Invincible: Defy Your Genetic Destiny to Live Better, Longer (https://amzn.to/3Pir404). In the middle of a tense conversation, it's easy for things to escalate quickly. But there's a simple three-word phrase that can instantly shift the tone—turning conflict into something more productive and less combative. Source: Bill Jensen author of The Simplicity Survival Handbook (https://amzn.to/4thwWEX) PLEASE SUPPORT OUR SPONSORS AQUA TRU: Take the guesswork out of pure, great-tasting water. Head to https://AquaTru.com now and get 20% off your purifier using promo code SYSK. AquaTru even comes with a 30-day best-tasting water guarantee or your money back. RULA: This Mental Health Awareness Month, don't just think about your mental health - actually take the step to take care of it. Visit https://Rula.com/sysk to get started. QUINCE: Refresh your everyday with luxury you will actual use! Go to https://Quince.com/sysk for free shipping on your order and 365-day returns. Now available in Canada, too! SHOPIFY: It's time to turn those "what ifs" into CHA CHING with Shopify Today! Sign up for your $1 per month trail and start selling today at https://Shopify.com/sysk Learn more about your ad choices. Visit megaphone.fm/adchoices
Most everyone knows the story of holocaust survivor Viktor Frankl who wrote the book, Man's Search For Meaning. In the book he shares his journey of finding meaning, purpose, and peace even as a prisoner in a concentration camp. A primary message he had for humanity was that regardless of circumstances, we have the freedom to choose our attitude in any situation. He feels this is what kept him alive while most around him died. But when the time came when Viktor was freed from his prison, he didn't stay there, saying he'd found peace and was good. He left to embrace the comforts and security of freedom. We as humans seem to inherently desire just that, comfort and security. I don't see that changing, and I'm not criticizing this, as I wake most mornings safe and sound in the comforts of my nice home full of all the latest amenities. But like Viktor, I want my core comfort and security to reside within me so that in times of hardship and uncertainty, I'm not devastated. We live in a time where we don't seem to be doing ok if things aren't certain for us. And they can't be. And as time goes on I align with the quote, “The more I learn the less I know,” usually attributed to Albert Einstein or Socrates. I find less and less that I can claim certainty with. But I'm also finding more peace than ever by accepting, not knowing. My guest in this episode is Simone Stolzoff. Simone is an author and journalist who explores big questions about work, meaning, and identity. He is the author of two books: The Good Enough Job and now, and the reason for me inviting him onto the show, he has written the book, How To Not Know: The Value of Uncertainty In a World That Demands Answers. Simone's work has been featured in The New York Times, The Atlantic, The Wall Street Journal, The Washington Post, and on the TED stage, and I found that many of the influential leaders I've had on this podcast follow Simone's research and work. Here we don't discount our desire for certainty, but dig into how we can remain secure when we are not certain. I'll add that I'm growing more distrusting of those who claim certainty, and at the point of rejecting the concept. Sign up for your $1/month trial period at shopify.com/kevin Go to shipstation.com and use code KEVIN to start your free trial. Learn more about your ad choices. Visit megaphone.fm/adchoices
I was looking for certainty when there was no certainty to be found. If Simone's words resonate with you, then this episode is for YOU. Simone Stolzoff is a journalist who writes about the uncertainty of life. In his conversation with Chris, he observes why people are becoming less tolerant of uncertainty, the harm caused when we take AI output as definitive answers, and what you can do to expand your capacity to hold uncertainty in your life.Featured guestFollow Simone Stolzoff on Instagram, LinkedIn, TikTok, and at simonestolzoff.com/Buy Simone's books How to Not Know and The Good Enough JobConnect with the teamFollow Chris on Instagram and at chrisduffycomedy.comBuy Chris' book, Humor Me Watch How to Be a Better Human videos on YouTube at TEDAudioCollectiveFollow TED on X, Instagram, Facebook, LinkedIn, and TikTokFor the full text transcript, visit go.ted.com/BHTranscriptsLearn more about our flagship conference happening this April at attend.ted.com/podcast Hosted on Acast. See acast.com/privacy for more information.
Change is constant, but the right insight at the right moment can make all the difference. In this season finale compilation, we're revisiting the hard-won lessons, unexpected turns, and honest conversations that defined Leading Up: The Work Shift. The incredible guests featured in this episode — Krista Chism, Pat Flynn, James Whitmore, Lorraine Lee, Ahyiana Angel, Zak Brown, Terrin Lawrence, Simone Stolzoff, Deborah Grayson Riegel, and Dorie Clark — remind us that navigating the future of work is about staying curious, keeping your eyes on the horizon, and always leading up. Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. If you're trying to skill up, head to Udemy.com Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast Production by Pod People
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Professional uncertainty can be as damaging to our health as actually losing a job. So why do we keep white-knuckling for certainty—and what happens when we finally let go? This week, Elizabeth sits down with Simone Stolzoff, author of The Good Enough Job and the forthcoming How to Not Know: The Value of Uncertainty in a World That Demands Answers, to explore why our instinct to seek certainty may be the very thing holding us back. Simone shares what years of researching ambiguity taught him about reframing uncertainty—not as a threat to manage, but as an opportunity to collaborate with. Plus: why the human skills employers want most are exactly the ones AI can't replicate. Follow Leading Up: The Work Shift on Apple, Spotify, or wherever you listen. New episodes drop Tuesdays. If you're trying to skill up, head to Udemy.com Find out more about Leading Up: The Work Shift at business.udemy.com/leading-up-podcast Production by Pod People
Work Less, Live More and Own Your Time with Andy Hill | 079In this powerful episode of The Extreme Personal Finance Show, Chris Luger sits down with Andy Hill, Accredited Financial Counselor®, author of Own Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grind, and creator of Marriage, Kids and Money.Andy shares how he and his wife went from overworked corporate life to living intentionally, with more time for family, health, and happiness. Together, they dive into:How to own your time instead of selling itWhat “diversifying your identity” really means after leaving corporate lifeThe moment Andy realized he needed to walk away from a six-figure jobHow to teach kids generosity, gratitude, and financial independence earlyWhy success isn't a number. it's a calendar that reflects your valuesIf you're stuck in the grind and dreaming of more time, freedom, and purpose listen now! Pre-order Andy's book: Own Your Time (January 2026)Visit MarriageKidsAndMoney.com for moreContact Chris:https://heavymetal.moneyhttps://www.facebook.com/MoneyHeavyMetalhttps://x.com/MoneyHeavyMetalhttps://www.instagram.com/chrislugerhttps://www.tiktok.com/@heavymetalmoneyemail: chris at heavymetal.moneyResources and Links: https://marriagekidsandmoney.comOwn Your Time: 10 Financial Steps to Put Your Family First and Escape the Corporate Grindby Andy Hill https://amzn.to/4oIN7JAMemento Mori Calendarshttps://www.amazon.com/s?k=memento+mori+calendarThe Good Enough Job: Reclaiming Life from Work by Simone Stolzoff https://amzn.to/4hwYbqFChris' Interview on Marriage, Kids and MoneyBecoming a Millionaire After Becoming Mortgage Freehttps://youtu.be/SKvJDS8ZAkA?si=3c7Jjg_NQjDL4VW6Big Tip Tuesdayhttps://marriagekidsandmoney.com/why-were-giving-100-tips-this-holiday-season-and-why-we-want-you-to-join-us/
Welcome back to Snafu with Robin Zander. In this episode, I'm joined by Miki Johnson – coach, facilitator, and co-founder of Job Portraits, a creative studio that helped companies tell honest stories about their work and culture. Today, Miki leads Leading By Example, where she supports leaders and teams through moments of change – whether that's a career shift, new parenthood, or redefining purpose. We talk about how to navigate transition with awareness, why enjoying change takes practice, and what it means to lead with authenticity in uncertain times. Miki shares lessons from a decade of coaching and storytelling – from building human-centered workplaces to bringing more body and emotion into leadership. We also explore creativity in the age of AI, and how technology can either deepen or disconnect us from what makes us human. And if you're interested in these kinds of conversations, we'll be diving even deeper into the intersection of leadership, creativity, and AI at Responsive Conference 2026. If you're interested, get your tickets here! https://www.responsiveconference.com/ __________________________________________________________________________________________ 00:00 Start 01:20 Miki's Background and Reservations about AI Miki hasn't used AI and has “very serious reservations.” She's not anti-AI – just cautious and curious. Her mindset is about “holding paradox”, believing two opposing things can both be true. Her background shapes that approach. She started as a journalist, later ran her own businesses, and now works as a leadership coach. Early in her career, she watched digital technology upend media and photography – industries “blown apart” by change. When she joined a 2008 startup building editable websites for photographers, it was exciting but also unsettling. She saw innovation create progress and loss at the same time. Now in her 40s with two sons, her focus has shifted. She worries less about the tools and more about what they do to people's attention, empathy, and connection – and even democracy. Her concern is how to raise kids and stay human in a distracted world. Robin shares her concerns but takes a different approach. He notes that change now happens “day to day,” not decade to decade. He looks at technology through systems, questioning whether pre-internet institutions can survive. “Maybe the Constitution was revolutionary,” he says, “but it's out of date for the world we live in.” He calls himself a “relentless optimist,” believing in democracy and adaptability, but aware both could fail without reform. Both worry deeply about what technology is doing to kids. Robin cites The Anxious Generation by Jonathan Haidt and says, “I don't believe social media is good for children.” He and his fiancée plan to limit their kids' screen time, just as Miki already does. They see it as a responsibility: raising grounded kids in a digital world. Robin sees AI as even more transformative – and risky – than anything before. “If social media is bigger than the printing press,” he says, “AI is bigger than the wheel.” He's amazed by its potential but uneasy about who controls it. He doubts people like Sam Altman act in the public's best interest. His concern isn't about rejecting AI but about questioning who holds power over it. Their difference lies in how they handle uncertainty. Miki's instinct is restraint and reflection – question first, act later, protect empathy and connection. Robin's instinct is engagement with vigilance – learn, adapt, and reform systems rather than retreat. Miki focuses on the human and emotional. Robin focuses on the structural and systemic. Both agree technology is moving faster than people can process or regulate. Miki uses curiosity to slow down and stay human. Robin uses curiosity to move forward and adapt. Together, they represent two sides of the same challenge: protecting what's most human while building what's next. 10:05 Navigating the Tech Landscape Miki starts by describing how her perspective has been shaped by living in two very different worlds. She spent over a decade in the Bay Area, surrounded by tech and startups. She later moved back to her small hometown of Athens, Ohio—a progressive college town surrounded by more rural areas. She calls it “a very small Austin”, a blue dot in a red state. She loves it there and feels lucky to have returned home. Robin interrupts briefly to highlight her background. He reminds listeners that Miki and her husband, Jackson, co-founded an employer branding agency called Job Portraits in 2014, the same year they got married. Over eight years, they grew it to around 15 full-time employees and 20 steady contractors. They worked with major startups like DoorDash, Instacart, and Eventbrite when those companies were still small—under 200 employees. Before that, they had started another venture in Chicago during Uber's early expansion beyond San Francisco. Their co-working space was right next to Uber's local team setting up drivers, giving them a front-row seat to the tech boom. Robin points out that Miki isn't coming at this topic as a “layperson.” She deeply understands technology, startups, and how they affect people. Miki continues, explaining how that background informs how she sees AI adoption today. Her Bay Area friends are all-in on AI. Many have used it since its earliest days—because it's part of their jobs, or because they're building it themselves. Others are executives leading companies developing AI tools. She's been watching it unfold closely for years, even if she hasn't used it herself. From her position outside the tech bubble now, she can see two clear camps: Those immersed in AI, excited and moving fast. And those outside that world—more cautious, questioning what it means for real people and communities. Living between those worlds—the fast-paced tech culture and her slower, more grounded hometown—gives her a unique vantage point. She's connected enough to understand the innovation but distant enough to see its costs and consequences. 16:39 The Cost of AI Adoption Miki points out how strange it feels to people in tech that she hasn't used AI. In her Bay Area circles, the idea is almost unthinkable. Miki understands why it's shocking. It's mostly circumstance—her coaching work doesn't require AI. Unlike consultants who “all tell leaders how to use AI,” her work is based on real conversations, not digital tools. Her husband, Jackson, also works at a “zero-technology” K–12 school he helped create, so they both exist in rare, tech-free spaces. She admits that's partly luck, not moral superiority, just “tiny pockets of the economy” where avoiding AI is still possible. Robin responds with his own story about adopting new tools. He recalls running Robin's Café from 2016 to 2019, when most restaurants still used paper timesheets. He connected with two young founders who digitized timesheets, turning a simple idea into a company that later sold to a global conglomerate. By the time he sold his café, those founders had retired in their 20s. “I could still run a restaurant on paper,” he says, “but why would I, if digital is faster and easier?” He draws a parallel between tools over time—handwriting, typing, dictation. Each serves a purpose, but he still thinks best when writing by hand, then typing, then dictating. The point: progress adds options, not replacements. Miki distills his point: if a tool makes life easier, why not use it? Robin agrees, and uses his own writing practice as an example. He writes a 1,000-word weekly newsletter called Snafu. Every word is his, but he uses AI as an editor—to polish, not to create. He says, “I like how I think more clearly when I write regularly.” For him, writing is both communication and cognition—AI just helps him iterate faster. It's like having an instant editor instead of waiting a week for human feedback. He reminds his AI tools, “Don't write for me. Just help me think and improve.” When Miki asks why he's never had an editor, he explains that he has—but editors are expensive and slow. AI gives quick, affordable feedback when a human editor isn't available. Miki listens and reflects on the trade-offs. “These are the cost-benefit decisions we all make,” she says—small, constant choices about convenience and control. What unsettles her is how fast AI pushes that balance. She sees it as part of a long arc—from the printing press to now—but AI feels like an acceleration. It's “such a powerful technology moving so fast” that it's blowing the cover off how society adapts to change. Robin agrees: “It's just the latest version of the same story, since writing on cave walls.” 20:10 The Future of Human-AI Relationships Miki talks about the logical traps we've all started accepting over time. One of the biggest, she says, is believing that if something is cheaper, faster, or easier – it's automatically better. She pushes further: just because something is more efficient doesn't mean it's better than work. There are things you gain from working with humans that no machine can replicate, no matter how cheap or convenient it becomes. But we rarely stop to consider the real cost of trading that away. Miki says the reason we overlook those costs is capitalism. She's quick to clarify – she's not one of those people calling late-stage capitalism pure evil. Robin chimes in: “It's the best of a bunch of bad systems.” Miki agrees, but says capitalism still pushes a dangerous idea: It wants humans to behave like machines—predictable, tireless, cheap, and mistake-free. And over time, people have adapted to that pressure, becoming more mechanical just to survive within it. Now we've created a tool—AI—that might actually embody those machine-like ideals. Whether or not it reaches full human equivalence, it's close enough to expose something uncomfortable: We've built a human substitute that eliminates everything messy, emotional, and unpredictable about being human. Robin takes it a step further, saying half-jokingly that if humanity lasts long enough, our grandchildren might date robots. “Two generations from now,” he says, “is it socially acceptable—maybe even expected—that people have robot spouses?” He points out it's already starting—people are forming attachments to ChatGPT and similar AIs. Miki agrees, noting that it's already common for people under 25 to say they've had meaningful interactions with AI companions. Over 20% of them, she estimates, have already experienced this. That number will only grow. And yet, she says, we talk about these changes as if they're inevitable—like we don't have a choice. That's what frustrates her most: The narrative that AI “has to” take over—that it's unstoppable and universal—isn't natural evolution. It's a story deliberately crafted by those who build and profit from it. “Jackson's been reading the Hacker News comments for 15 years,” she adds, hinting at how deep and intentional those narratives run in the tech world. She pauses to explain what Hacker News is for anyone unfamiliar. It's one of the few online forums that's still thoughtful and well-curated. Miki says most people there are the ones who've been running and shaping the tech world for years—engineers, founders, product leaders. And if you've followed those conversations, she says, it's obvious that the people developing AI knew there would be pushback. “Because when you really stop and think about it,” she says, “it's kind of gross.” The technology is designed to replace humans—and eventually, to replace their jobs. And yet, almost no one is seriously talking about what happens when that becomes real. “I'm sorry,” she says, “but there's just something in me that says—dating a robot is bad for humanity. What is wrong with us?” Robin agrees. “I don't disagree,” he says. “It's just… different from human.” Miki admits she wrestles with that tension. “Every part of me says, don't call it bad or wrong—we have to make space for difference.” But still, something in her can't shake the feeling that this isn't progress—it's disconnection. Robin expands on that thought, saying he's not particularly religious, but he does see humanity as sacred. “There's something fundamental about the human soul,” he says. He gives examples: he has metal in his ankle from an old injury; some of his family members are alive only because of medical devices. Technology, in that sense, can extend or support human life. But the idea of replacing or merging humans with machines—of being subsumed by them—feels wrong. “It's not a world I want to live in,” he says plainly. He adds that maybe future generations will think differently. “Maybe our grandkids will look at us and say, ‘Okay boomer—you never used AI.'” 24:14 Practical Applications of AI in Daily Life Robin shares a story about a house he and his fiancée almost bought—one that had a redwood tree cut down just 10 feet from the foundation. The garage foundation was cracked, the chimney tilted—it was clear something was wrong. He'd already talked to arborists and contractors, but none could give a clear answer. So he turned to ChatGPT's Deep Research—a premium feature that allows for in-depth, multi-source research across the web. He paid $200 a month for unlimited access. Ran 15 deep research queries simultaneously. Generated about 250 pages of analysis on redwood tree roots and their long-term impact on foundations. He learned that if the roots are alive, they can keep growing and push the soil upward. If they're dead, they decompose, absorb and release water seasonally, and cause the soil to expand and contract. Over time, that movement creates air pockets under the house—tiny voids that could collapse during an earthquake. None of this, Robin says, came from any contractor, realtor, or arborist. “Even they said I'd have to dig out the roots to know for sure,” he recalls. Ultimately, they decided not to buy that house—entirely because of the data he got from ChatGPT. “To protect myself,” he says, “I want to use the tools I have.” He compares it to using a laser level before buying a home in earthquake country: “If I'll use that, why not use AI to explore what I don't know?” He even compares Deep Research to flipping through Encyclopedia Britannica as a kid—hours spent reading about dinosaurs “for no reason other than curiosity.” Robin continues, saying it's not that AI will replace humans—it's that people who use AI will replace those who don't. He references economist Tyler Cowen's Average Is Over (2012), which described how chess evolved in the early 2000s. Back then, computers couldn't beat elite players on their own—but a human + computer team could beat both humans and machines alone. “The best chess today,” Robin says, “is played by a human and computer together.” “There are a dozen directions I could go from there,” Miki says. But one idea stands out to her: We're going to have to choose, more and more often, between knowledge and relationships. What Robin did—turning to Deep Research—was choosing knowledge. Getting the right answer. Having more information. Making the smarter decision. But that comes at the cost of human connection. “I'm willing to bet,” she says, “that all the information you found came from humans originally.” Meaning: there were people who could have told him that—just not in that format. Her broader point: the more we optimize for efficiency and knowledge, the less we may rely on each other. 32:26 Choosing Relationships Over AI Robin points out that everything he learned from ChatGPT originally came from people. Miki agrees, but says her work is really about getting comfortable with uncertainty. She helps people build a relationship with the unknown instead of trying to control it. She mentions Robin's recent talk with author Simone Stolzoff, who's writing How to Not Know—a book she can't wait to read. She connects it to a bigger idea: how deeply we've inherited the Enlightenment mindset. “We're living at the height of ‘I think, therefore I am,'” she says. If that's your worldview, then of course AI feels natural. It fits the logic that more data and more knowledge are always better. But she's uneasy about what that mindset costs us. She worries about what's happening to human connection. “It's all connected,” she says—our isolation, mental health struggles, political polarization, even how we treat the planet. Every time we choose AI over another person, she sees it as part of that drift away from relationship. “I get why people use it,” she adds. “Capitalism doesn't leave most people much of a choice.” Still, she says, “Each time we pick AI over a human, that's a decision about the kind of world we're creating.” Her choice is simple: “I'm choosing relationships.” Robin gently pushes back. “I think that's a false dichotomy,” he says. He just hosted Responsive Conference—250 people gathered for human connection. “That's why I do this podcast,” he adds. “To sit down with people and talk, deeply.” He gives a personal example. When he bought his home, he spoke with hundreds of people—plumbers, electricians, roofers. “I'm the biggest advocate for human conversations,” he says. “So why not both? Why not use AI and connect with people?” To him, the real question is about how we use technology consciously. “If we stopped using AI because it's not human,” he asks, “should we stop using computers because handwriting is more authentic?” “Should we reject the printing press because it's not handwritten?” He's not advocating blind use—he's asking for mindful coexistence. It's also personal for him. His company relies on AI tools—from Adobe to video production. “AI is baked into everything we do,” he says. And he and his fiancée—a data scientist—often talk about what that means for their future family. “How do we raise kids in a world where screens and AI are everywhere?” Then he asks her directly: “What do you tell your clients? Treat me like one—how do you help people navigate this tension?” Miki smiles and shakes her head. “I don't tell people what to do,” she says. “I'm not an advisor, I'm a coach.” Her work is about helping people trust their own intuition. “Even when what they believe is contrarian,” she adds. She admits she's still learning herself. “My whole stance is: I don't know. I don't know. I don't know.” She and her husband, Jackson, live by the idea of strong opinions, loosely held. She stays open—lets new conversations change her mind. “And they do,” she says. “Every talk like this shifts me a little.” She keeps seeking those exchanges—with parents, tech workers, friends—because everyone's trying to figure out the same thing: How do we live well with technology, without losing what makes us human? 37:16 The Amish Approach to Technology Miki reflects on how engineers are both building and being replaced by AI. She wants to understand the technology from every angle—how it works, how it affects people, and what choices it leaves us with. What worries her is the sense of inevitability around AI—especially in places like the Bay Area. “It's like no one's even met someone who doesn't use it,” she says. She knows it's embedded everywhere—Google searches, chatbots, everything online. But she doesn't use AI tools directly or build with them herself. “I don't even know the right terminology,” she admits with a laugh. Robin points out that every Google search now uses an LLM. Miki nods, saying her point isn't denial—it's about choice. “You can make different decisions,” she says. She admits she hasn't studied it deeply but brings up an analogy that helps her think about tech differently: the Amish. “I call myself kind of ‘AI Amish,'” she jokes. She explains her understanding of how the Amish handle new technology. They're not anti-tech; they're selective. They test and evaluate new tools to see if they align with their community's values. “They ask, does it build connection or not?” They don't just reject things—they integrate what fits. In her area of Ohio, she's seen Amish people now using electric bikes. “That's new since I was a kid,” she says. It helps them connect more with each other without harming the environment. They've also used solar power for years. It lets them stay energy independent without relying on outside systems that clash with their values. Robin agrees—it's thoughtful, not oppositional. “They're intentional about what strengthens community,” he says. Miki continues: What frustrates her is how AI's creators have spent the last decade building a narrative of inevitability. “They knew there would be resistance,” she says, “so they started saying, ‘It's just going to happen. Your jobs won't be taken by AI—they'll be taken by people who use it better than you.'” She finds that manipulative and misleading. Robin pushes back gently. “That's partly true—but only for now,” he says. He compares it to Uber and Lyft: at first, new jobs seemed to appear, but eventually drivers started being replaced by self-driving cars. Miki agrees. “Exactly. First it's people using AI, then it's AI replacing people,” she says. What disturbs her most is the blind trust people put in companies driven by profit. “They've proven over and over that's their motive,” she says. “Why believe their story about what's coming next?” She's empathetic, though—she knows why people don't push back. “We're stressed, broke, exhausted,” she says. “Our nervous systems are fried 24/7—especially under this administration.” “It's hard to think critically when you're just trying to survive.” And when everyone around you uses AI, it starts to feel mandatory. “People tell me, ‘Yeah, I know it's a problem—but I have to. Otherwise I'll lose my job.'” “Or, ‘I'd have bought the wrong house if I didn't use it.'” That “I have to” mindset, she says, is what scares her most. Robin relates with his own example. “That's how I felt with TikTok,” he says. He got hooked early on, staying up until 3 a.m. scrolling. After a few weeks, he deleted the app and never went back. “I probably lose some business by not being there,” he admits. “But I'd rather protect my focus and my sanity.” He admits he couldn't find a way to stay on the platform without it consuming him. “I wasn't able to build a system that removed me from that platform while still using that platform.” But he feels differently about other tools. For example, LinkedIn has been essential—especially for communicating with Responsive Conference attendees. “It was our primary method of communication for 2025,” he says. So he tries to choose “the lesser of two evils.” “TikTok's bad for my brain,” he says. “I'm not using it.” “But with LLMs, it's different.” When researching houses, he didn't feel forced into using them to “keep up.” To him, they're just another resource. “If encyclopedias are available, use them. If Wikipedia's available, use both. And if LLMs can help, use all three.” 41:45 The Pressure to Conform to Technology Miki challenges that logic. “When was the last time you opened an encyclopedia?” Robin pauses. “Seven years ago.” Miki laughs. “Exactly. It's a nice idea that we'll use all the tools—but humans don't actually do that.” We gravitate toward what's easiest. “If you check eBay, there are hundreds of encyclopedia sets for sale,” she says. “No one's using them.” Robin agrees but takes the idea in a new direction. “Sure—but just because something's easy doesn't mean it's good,” he says. He compares it to food: “It's easier to eat at McDonald's than cook at home,” he says. But easy choices often lead to long-term problems. He mentions obesity in the U.S. as a cautionary parallel. Some things are valuable because they're hard. “Getting in my cold plunge every morning isn't easy,” he says. “That's why I do it.” “Exercise never gets easy either—but that's the point.” He adds a personal note: “I grew up in the mountains. I love being at elevation, off-grid, away from electricity.” He could bring Starlink when he travels, but he chooses not to. Still, he's not trying to live as a total hermit. “I don't want to live 12 months a year at 10,000 feet with a wood stove and no one around.” “There's a balance.” Miki nods, “I think this is where we need to start separating what we can handle versus what kids can.” “We're privileged adults with fully formed brains,” she points out. “But it's different for children growing up inside this system.” Robin agrees and shifts the focus. Even though you don't give advice professionally,” he says, “I'll ask you to give it personally.” “You're raising kids in what might be the hardest time we've ever seen. What are you actually practicing at home?” 45:30 Raising Children in a Tech-Driven World Robin reflects on how education has shifted since their grandparents' time Mentions “Alpha Schools” — where AI helps kids learn basic skills fast (reading, writing, math) Human coaches spend the rest of the time building life skills Says this model makes sense: Memorizing times tables isn't useful anymore He only learned to love math because his dad taught him algebra personally — acted like a coach Asks Miki what she thinks about AI and kids — and what advice she'd give him as a future parent Miki's first response — humility and boundaries “First off, I never want to give parents advice.” Everyone's doing their best with limited info and energy Her kids are still young — not yet at the “phone or social media” stage So she doesn't pretend to have all the answers Her personal wish vs. what's realistic Ideal world: She wishes there were a global law banning kids from using AI or social media until age 18 Thinks it would genuinely be better for humanity References The Anxious Generation Says there's growing causal evidence, not just correlation, linking social media to mental health issues Mentions its impact on children's nervous systems and worldview It wires them for defense rather than discovery Real world: One parent can't fight this alone — it's a collective action problem You need communities of parents who agree on shared rules Example: schools that commit to being zero-technology zones Parents and kids agree on: What ages tech is allowed Time limits Common standards Practical ideas they're exploring Families turning back to landlines Miki says they got one recently Not an actual landline — they use a SIM adapter and an old rotary phone Kids use it to call grandparents Her partner Jackson is working on a bigger vision: Building a city around a school Goal: design entire communities that share thoughtful tech boundaries Robin relates it to his own childhood Points out the same collective issue — “my nephews are preteens” It's one thing for parents to limit screen time But if every other kid has access, that limit won't hold Shares his own experience: No TV or video games growing up So he just went to neighbors' houses to play — human nature finds a way Says individual family decisions don't solve the broader problem Miki agrees — and expands the concern Says the real issue is what kids aren't learning Their generation had “practice time” in real-world social interactions Learned what jokes land and which ones hurt Learned how to disagree, apologize, or flirt respectfully Learned by trial and error — through millions of small moments With social media and AI replacing those interactions: Kids lose those chances entirely Results she's seeing: More kids isolating themselves Many afraid to take social or emotional risks Fewer kids dating or engaging in real-life relationships Analogy — why AI can stunt development “Using AI to write essays,” she says, “is like taking a forklift to the gym.” Sure, you lift more weight — but you're not getting stronger Warns this is already visible in workplaces: Companies laying off junior engineers AI handles the entry-level work But in 5 years, there'll be no trained juniors left to replace seniors Concludes that where AI goes next “is anybody's guess” — but it must be used with intention 54:12 Where to Find Miki Invites others to connect Mentions her website: leadingbyexample.life Visitors can book 30-minute conversations directly on her calendar Says she's genuinely open to discussing this topic with anyone interested
Thinking about quitting, but not sure if you'll regret it? This episode will help you work out whether it's time to leave, or if there's still something worth holding onto. We've all been there: lying awake at night, weighing the costs of staying against the risks of walking away. Do you push through and hope it gets better, or cut your losses before you waste more time? In this episode, I've brought together Ash Ambirge, Julia Keller, Simone Stolzoff and Monique Ross to help you figure it out. We'll explore the hidden traps that keep us stuck, the real benefits of quitting, and the surprising strategies that can make staying a lot better than it feels right now. Plus at the end, I'll give you five questions that can bring your answer into focus, fast.
Welcome back to Snafu w/ Robin Zander. In this episode, I'm joined by Simone Stolzoff – author of The Good Enough Job and the upcoming How to Not Know – and our opening keynote speaker at Responsive Conference 2025. We explore what it means to have an identity beyond your job title, why rest is essential for high performance, and how ritual and community offer grounding in an age of uncertainty. Simone shares how Judaism and Shabbat have shaped his views on balance, the role of “guardrails” over boundaries, and how we can build more durable lives – personally and professionally. We talk about the future of religion, the risks and opportunities of AI, and why books still matter even in a tech-saturated world. Simone also offers practical writing advice, previews his next book, and explains why embracing uncertainty may be the most valuable skill of all. Simone will be speaking live at Responsive Conference 2025, September 17–18, and I can't wait for you to hear more. If you haven't gotten your tickets yet, get them here. Start (00:00) Identity Beyond Titles (01:07.414) What identities do you hold that aren't listed on your LinkedIn? Simone's Answer: Ultimate frisbee player – “the entirety of my adult life” Aspiring salsa dancer – taking intro classes with his wife Former spoken word poet – “It was the most important thing to me when I was 19 years old.” New father – navigating life with a five-month-old "I encourage people to ask: what do you like to do, as opposed to what do you do?" Shabbat as a Sanctuary in Time (01:58.831) Robin references Simone's TED Talk, focusing on Shabbat as a metaphor for boundary-setting and presence. Simone expands: Shabbat offers a weekly rhythm to separate work from rest. Emphasizes the idea of "sacred time" and intentional disconnection from screens. Shabbat is a “sanctuary in time,” paralleling physical sanctuaries like churches or synagogues. Relates this to work-life balance, noting that intentions alone aren't enough – infrastructure is needed. "We have intentions… but what actually leads to balance is structural barriers." Boundaries vs. Guardrails (04:44.32) Cites Anne Helen Petersen's metaphor: Boundaries = painted lane lines Guardrails = physical barriers that actually keep you on the road There are calls for more guardrails (structural protections) in modern life. Examples: Airplane mode during playtime with his kid Attending yoga or activities where work can't creep in "Individually imposed boundaries often break down when the pressures of capitalism creep in." Religion, Ritual & Community (06:48.57) Robin asks how Judaism has shaped Simone's thinking around work and life. Simone reflects: Religion offers a “container” with a different value system than capitalism. As organized religion declined, people turned to work for identity, meaning, and community. Religion can offer rituals to process uncertainty — e.g., mourning rituals like sitting shiva. Religious or community spaces offer contrast: they don't care about your career success. "Religion is sort of like a container… with a value system that isn't just about growth charts." "It can be refreshing to say: Day 1, do this. Day 7, go for a walk." Personal journey: Simone reconnected with Judaism in his 30s as he built his own family. Once, went out of obligation, then rejected it, and now see beauty in ritual and intergenerational wisdom. The Future of Religion & Community (09:12.454) Robin theorizes a future rise in spiritual and communal gatherings: Predicts new spiritual movements or evolutions of old ones Notes a hunger for meaningful in-person connection, especially post-AI and amid tech saturation "There's a hunger... as AI and screens define how we relate, people want to gather in person." "I don't tend to make predictions, but I think this one's inevitable." Simone agrees... but offers data as contrast: Cites the decline in religious affiliation in the U.S. 1950s: 3–4% unaffiliated Today: Nearly 1 in 3 identify as “Nones” (no religion) Notes reasons: Rising wealth tends to increase secularism The internet creates alternate identity spaces "I do believe there is inevitability in the growth [of spirituality]... But the data points the opposite way." Simone reflects on the factors behind declining religious affiliation: Doubt now builds community – the internet has enabled people to connect around leaving religion as much as practicing it. Political entanglement – many young Americans, especially, are alienated by the perceived overlap between right-wing politics and Christianity. Yet despite this secular trend, the need for meaning, ritual, and purpose remains universal. “There still is this fundamental need to find meaning, to find purpose, to find ritual… even if it's not in the forms we're used to.” A Church in the Mission (13:07.182) Robin shares a formative experience from 2016: That year, he launched both Robin's Café and the first Responsive Conference. When he walked into the theater space that would become his café, he encountered a young, diverse Christian revival group – live music, dancing, and energetic worship happening in a Mission District theater. This juxtaposition – a traditional spiritual gathering inside a modern, “hip” venue – left a lasting impression. “It felt like a revival meeting in the South… except it was full of people my age and younger, partying on a Saturday morning – and it just happened to be church.” You Are More Than Your Work (14:51.182) Robin segues into the idea of multiple identities: He recalls how reading The 4-Hour Work Week helped him embrace not defining himself solely by his entrepreneurial work. Even on tough days running a business, movement and fitness have been a grounding force – something he does daily, independent of career performance. Quotes from Simone's TED Talk: “Some people do what they love for work; others work so they can do what they love. Neither is more noble.” Robin asks Simone to share the origin of this line and how it connects to the poet Anis Mojgani. Simone recounts a pivotal conversation during college: As a poetry and economics double major, he was wrestling with career path anxiety. He interviewed his favorite poet, Anis Mojgani, asking: “Do you believe in the idea, ‘Do what you love and never work a day in your life'?” Mojgani's response: “Some people do what they love for work. Others do what they have to so they can do what they love when they're not working. Neither is more noble.” This countered Simone's expectations and left a deep impression. He highlights two cases for cultivating a broader identity beyond work: Business Case: High performance requires rest. People with “greater self-complexity” — more identities outside of work — are more creative, more resilient, and more emotionally stable. Moral Case: Investing in other parts of ourselves makes us better citizens, community members, and humans. Singular identity (especially career-based) is fragile and susceptible to collapse — e.g., pandemic layoffs. Solely work-based identity also sets unrealistically high expectations that can lead to disappointment. “You're balancing on a very narrow platform… You're susceptible to a large gust of wind.” Robin reflects on how the Responsive Manifesto intentionally avoids prescribing one path: It's not anti-work or anti-grind. Recognizes that sometimes hard work is necessary, especially in entrepreneurship. Shares how his friend's newsletter, Just Go Grind, embraces the idea that seasons of hustle are sometimes required. “Everyone figuring out their own boundaries is actually the goal.” Work Isn't Good or Bad – It's Complex (18:34.436) Simone adds that society tends to polarize the narrative around work: Some say “burn it all down”, that work is evil. Others say, “Do what you love, or it's not worth doing.” His book The Good Enough Job argues for a middle way: It's not hustle propaganda. It's not a slacker's manifesto. It's about recognizing that we spend a huge portion of our lives working, so it matters how we approach it, but also recognizing we're more than just our jobs. He introduces the concept of temporal balance: “There's a natural seasonality to work.” Sometimes, long hours are necessary (e.g., startup mode, sales targets). But it should be a season, not a permanent lifestyle. What's the Role of Books in the Age of AI? (22:41.507) Robin poses a forward-looking question: In an age when AI can summarize, synthesize, and generate information rapidly, what's the role of books? Especially nonfiction, where facts are easier to reproduce. Simone responds with both uncertainty and hope: Human storytelling as a moat: His work relies on reporting, profiling, and character studies — something LLMs can't yet replicate with nuance. He doesn't know how long this will remain defensible, but will continue to lean into it. Books are more than information: Books have utility beyond facts: they are entertainment, physical objects, and cultural symbols. Quotes the vibe of being surrounded by books: there's even an untranslatable word (possibly German or Japanese) about the comfort of unread books. A vinyl-record future: Books may become more niche, collectible, or artisanal, similar to vinyl. But they still hold society's most well-formed, deeply considered ideas. The human touch still matters: A typed note that looks handwritten isn't the same as a note that is handwritten. People will crave authenticity and human creation, especially in a tech-saturated world. “You can appreciate when something has a level of human touch, especially in an increasingly tech-powered world.” He closes with a self-aware reflection: “I don't claim to know whether my career will still exist in five years… which is why I picked this topic for my second book.” “Created by Humans” (25:49.549) Robin references a conversation with Bree Groff, who imagined a world where creative work carries a “Created by Human” tag, like organic food labeling. “I think we'll see that [kind of labeling] in the next few decades – maybe even in the next few years.” As AI-generated content floods the market, human-made work may soon carry new cultural cachet. Simone shares a turning point: after submitting an op-ed to The New York Times, his editor flagged a bad metaphor. En route to a bachelor party, he opened ChatGPT, asked for new metaphors, chose one, and it made the print edition the next day. “Maybe I've broken some law about journalism ethics... but that was the moment where I was like: whoa. This sh*t is crazy.” The Home-Buying Crash Course Powered by AI (27:57) Robin's breakthrough came while navigating the chaos of buying a house. He used ChatGPT to upskill rapidly: Structural questions (e.g., redwood roots and foundation risk) Zoning and legal research Negotiation tactics “The rate of learning I was able to create because of these tools was 10 to 100 times faster than what I could've done previously.” How to Live Without Knowing (29:41.498) Simone previews his next book, How to Not Know, a field guide for navigating uncertainty. In an age of instant answers, our tolerance for the unknown is shrinking, while uncertainty itself is growing. “We're trying to find clarity where there is none. My hope is that the book offers tools to live in that space.” The “Three Horsemen of Delusion”: Comfort – we crave the ease of certainty. Hubris – we assume we know more than we do. Control – we believe certainty gives us power over the future. Robin asks how Simone finds his stories. His answer: chase change. Whether internal (doubt, transformation) or external (leaving a cult, facing rising seas), he seeks tension and evolution. Examples: A couple questioning their marriage An employee leading dissent at work A man leaving his religious identity behind A nation (Tuvalu) confronting its own disappearance “The story you find is always better than the one you seek.” Want to Be a Writer? Start Writing. (36:50.554) Robin asks for writing advice. Simone offers two pillars: Ask These Four Questions: What's the story? Why should people care? Why now? Why you? “Only you can tell the story of buying a café and selling it on Craigslist.” Build the Practice: Writing is not just inspiration—it's routine. Schedule it. Join a group. Set deadlines. “Writing is the act of putting your ass in the chair.” Robin applauds Simone's book title, How to Not Know, for its playfulness and relevance. He asks how Simone's own relationship with uncertainty has evolved through his research. Simone reflects on how writing his first book, The Good Enough Job, softened his stance, from a hot take to a more nuanced view of work's role in life. Similarly, with his new book, his thinking on uncertainty has shifted. “Uncertainty is uncomfortable by design. That discomfort is what makes us pay attention.” Simone once championed uncertainty for its spontaneity and freedom. But now, he sees a more complex dance between certainty and uncertainty. “Certainty begets the ability to become more comfortable with uncertainty.” He gives the example of a younger self traveling with no plan, and the maturity of seeing how some people use uncertainty to avoid depth and commitment. Durable Skills for an Unstable Future (43:57.613) Robin shifts to the practical: In a world where stability is fading, what should we teach future generations? Simone shares three core “durable skills”: Learn how to learn – Adaptability beats certainty. Tell compelling stories – Human connection never goes out of style. Discern control from chaos – Use a mental decision tree: What can I control? If I can't control it, can I prepare? If I can't prepare, can I accept? “Often we're more uncomfortable with uncertainty than with a certain bad outcome.” He cites research showing people are stressed more by maybe getting shocked than actually getting shocked. AI as Editor, Not Author (47:23.765) Robin circles back to AI. Simone explains how his relationship with it has evolved: He never uses it for first drafts or ideation. Instead, AI serves as a “sparring partner” in editing – great at spotting drag, less useful at solving it. “People are often right about something being wrong, but not about the solution. I treat AI the same way.” Simone defends creative friction as essential to craft: rewriting, deleting, struggling – that's the work. The Chinese Farmer & the Fallacy of Forecasts (50:27.215) Robin expresses cautious optimism – but also fears AI will widen inequality and erode entry-level jobs. He asks what gives Simone hope. Simone counters with the “Parable of the Chinese Farmer,” where events can't be judged good or bad in real time. His conclusion: we don't know enough to be either pessimistic or optimistic. “Maybe AI ushers in civil unrest. Maybe a golden age. Maybe yes, maybe no.” He's most hopeful about the growing value of human touch – gifts of time, love, and effort in an increasingly automated world. Where to Find Simone (53:44.845) Website: thegoodenoughjob.com Newsletter: The Article Book Club (monthly articles not written by him, thousands of subscribers) Robin reminds listeners that Simone will be the opening speaker at Responsive Conference 2025, September 17–18. People Mentioned: M'Gilvry Allen Anne Helen Petersen Anis Mojgani Bree Groff Tim Ferriss Steven Pressfield Ernest Hemingway Justin Gordon Organizations Mentioned: Responsive Conference Zander Media Asana, Inc X, The Moonshot Factory (formerly Google X) Waymo, Jewish Community Centers (Boulder & Denver) Robin's Cafe Amazon Google / Alphabet Books & Newsletters The Good Enough Job How to Not Know (upcoming book) The 4‑Hour Workweek Just Go Grind Article Book Club
Why is it that people seem to come up with good ideas in the shower? Could there really be something special about the shower experience that generates great thoughts and simple solutions? This episode begins with some interesting research about the magic of the shower. https://www.headspace.com/articles/shower-epiphanies The strangest things can affect your health. For example, your birthday or if there is a parade or a 10K in your town. Even if there is EZ Pass on a highway somewhere near you can affect your health. It sounds odd and you may ask: How can that be? To answer that and explain all of this is my guest Anupam B. Jena. Bapu, as he is called, is a medical doctor, economist, Harvard professor and author of the book Random Acts of Medicine: The Hidden Forces That Sway Doctors, Impact Patients, and Shape Our Health (https://amzn.to/3Y54hF4). In our culture people take great pride in their work and career. A job can become part of our self-worth and identity. Is that a good thing? For some it is – but it is not true for everyone according to Simone Stolzoff. He is a journalist who has written for The Atlantic, WIRED and numerous other publications. He is also author of the book The Good Enough Job: Reclaiming Life from Work (https://amzn.to/44MYZjI). Simone explains why seeking out the perfect job at the expense of other aspects of life can be trouble. Could brushing your teeth help you lose weight? Maybe. It's apparently all about WHEN you brush them. Listen as I explain how good dental hygiene can reduce the size of your waistline. https://www.popsci.com/does-brushing-your-teeth-affect-your-appetite/ PLEASE SUPPORT OUR SPONSORS!!! SHOPIFY: Shopify is the commerce platform for millions of businesses around the world! To start selling today, sign up for your $1 per month trial at https://Shopify.com/sysk INDEED: Get a $75 sponsored job credit to get your jobs more visibility at https://Indeed.com/SOMETHING right now! QUINCE: Stick to the staples that last, with elevated essentials from Quince! Go to https://Quince.com/sysk for free shipping on your order and 365 day returns! HERS: Hers is transforming women's healthcare by providing access to affordable weight loss treatment plans, delivered straight to your door, if prescribed. Start your initial free online visit today at https://forhers.com/something DELL: The Black Friday in July event from Dell Technologies is here. Upgrade for a limited-time only at https://Dell.com/deals Learn more about your ad choices. Visit megaphone.fm/adchoices
Today's letter writers thought they had their work lives sorted. But… turns out, maybe not. Should they start a new job search? And if they do, what questions should they ask themselves—and their prospective employers? Listen in as Jen and Sara help these folks pause their panic and get choosy—instead of waiting around to be chosen. Links:Check out the First Round Review's The 40 Best Questions to Ask in an InterviewGrab a copy of Simone Stolzoff's The Good Enough JobGot a work situation eating away at you? Send it to us! Submit your dilemma at PMLEshow.com
In this eye-opening conversation, we sit down with Simone Stolzoff, author of The Good Enough Job, to explore why modern work culture traps so many of us in cycles of burnout, identity crises, and unrealistic ambition. Drawing on research and personal experience, Simone challenges the “dream job” myth and offers a liberating framework: redefine success on your terms. We explore the dangers of workism, the importance of building an identity outside of your career, and the power of setting clear boundaries. For high-achievers who feel stuck on the hedonic treadmill, this episode offers a roadmap to a more balanced, meaningful life — without abandoning your ambition. [00:00:00] Introduction [00:02:26] The real meaning of a “good enough job” — and why it's not about slacking off [00:08:16] The rise of workism: why your job became your identity [00:13:33] The difference between boundaries and guardrails — and why we need both [00:21:14] The myth of the dream job (and why passion usually follows skill, not the other way around) [00:27:41] How to rebuild an identity outside of work and escape workaholism [00:39:28] The surprising reason people at both ends of the ambition spectrum struggle [00:50:00] Why defining your “enough” number is the antidote to endless striving [00:56:08] Simone's personal lesson: why time autonomy is his ultimate luxury Episode Takeaways: Your job should support your life, not become your life. Stop chasing perfection — a “good enough” job can free you to thrive in other areas that matter. Identity is like an investment portfolio: diversify it beyond just work. Intrinsic motivation (mastery, purpose, autonomy) beats external markers of success. Define your personal “enough” — financially, emotionally, and professionally — or risk falling into the endless “more” trap. Play, beginner's mindset, and non-work communities are secret weapons for resilience. Tired of awkward handshakes and collecting business cards without building real connections? Dive into our Free Social Capital Networking Masterclass. Learn practical strategies to make your interactions meaningful and boost your confidence in any social situation. Sign up for free at theartofcharm.com/sc and elevate your networking from awkward to awesome. Don't miss out on a network of opportunities! Unleash the power of covert networking to infiltrate high-value circles and build a 7-figure network in just 90 days. Ready to start? Check out our CIA-proven guide to networking like a spy! Indulge in affordable luxury with Quince—where high-end essentials meet unbeatable prices. Upgrade your wardrobe today at quince.com/charm for free shipping and hassle-free returns. Ready to turn your business idea into reality? Shopify makes it easy to start, scale, and succeed—whether you're launching a side hustle or building the next big brand. Sign up for your $1/month trial at shopify.com/charm. Need to hire top talent—fast? Skip the waiting game and get more qualified applicants with Indeed. Claim your $75 Sponsored Job Credit now at Indeed.com/charm. Curious about your influence level? Get your Influence Index Score today! Take this 60-second quiz to find out how your influence stacks up against top performers at theartofcharm.com/influence. Simone Stolzoff's website The Good Enough Job: Reclaiming Life from Work AJ on LinkedIn Johnny on LinkedIn AJ on Instagram Johnny on Instagram The Art of Charm on Instagram The Art of Charm on YouTube The Art of Charm on TikTok What to Listen ForEpisode Takeaways:A Word From Our SponsorsResources from this EpisodeCheck in with AJ and Johnny! Learn more about your ad choices. Visit megaphone.fm/adchoices
In this episode, we sit down with Simone Stolzoff, author of The Good Enough Job, to explore how modern work culture has taken over our identities—and how we can break free. This Best of MKM episode revisits one of our most powerful conversations about redefining success, setting boundaries, and reclaiming our time. If you're looking to escape the hustle mentality and build a more balanced life, this one's a must-listen! RESOURCES: Sponsors + Partners + Deals CHAPTERS 00:00 – Introduction: More Than Your Job 01:10 – Meet Simone Stolzoff & The Premise of The Good Enough Job 02:20 – Workism and Our Cultural Identity 04:30 – The Historical Shift in Work's Role 06:00 – The Risks of Overidentifying with Work 08:20 – Story of Kay He: The Wall Street Banker Burnout 11:00 – Simone's Personal Journey with Career Identity 13:40 – What Makes a Job 'Good Enough'? 15:40 – Identity Diversification: The Key to Resilience 18:30 – Practical Advice to Reclaim Life from Work 20:45 – Where to Find Simone & The Good Enough Job 21:15 – Closing Thoughts & Dalai Lama Quote MKM RESOURCES: MKM Coaching: Want 1-on-1 support with your family finance journey? Book a time with me today. Make My Kid a Millionaire Course: Want to build generational wealth and happiness for your kid? Learn more about my course! Coast FIRE Calculator: A free calculator to help you find out when you can slow down or stop investing for retirement. Mortgage Payoff Calculator: A free calculator to help you see how fast you can become mortgage free. YouTube: Subscribe for free to watch videos of these episodes and interviews. RECOMMENDED RESOURCES (SPONSORS AND AFFILIATES): Monarch Money - Best Budget App for Families & Couples Empower - Free Portfolio Tracker Crew - HYSA Banking Built for Families - Get an Extra 0.5% APY with my partner link Ethos - Affordable Term Life Insurance Trust & Will - Convenient Estate Planning HOW WE MAKE MONEY + DISCLAIMER: This show may contain affiliate links or links from our advertisers where we earn a commission, direct payment or products. Opinions are the creators alone. Information shared on this podcast is for entertainment purposes only and should not be considered as professional advice. Marriage Kids and Money (www.marriagekidsandmoney.com) is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to amazon.com. CREDITS: Podcast Artwork: Liz Theresa Editor: Johnny Sohl Podcast Support: Nev Maraj Learn more about your ad choices. Visit megaphone.fm/adchoices
Where do you draw the line between work and life? Writer Simone Stolzoff explores the problem with defining yourself by your job — and shows what it takes to reclaim your time and sense of meaning beyond the office. After the talk, Modupe shares how practicing meditation nourishes her identity outside of work. Hosted on Acast. See acast.com/privacy for more information.
If the questions ‘What do you do?' or ‘What's your dream job?' send you into an existential crisis, this episode is for you. As kids, society primes us to pick our dream job as if it's life's ultimate objective. But, what we as working professionals never consider is… Maybe it's okay to not have one. Join us as Simone Stolzoff, author of ‘The Good Enough Job,' challenges the conventional wisdom of entangling your career with your personal self-worth. In this episode, Ross, Natalie and Simone delve into the dangers of defining yourself solely by your profession and explore the consequences of neglecting other vital aspects of your life. Simone also shares his insights on navigating layoffs with resilience, overcoming different types of burnout, and cultivating fulfilling passions outside of work. Try Notion for free when you go to https://notion.com/demoted Go to https://Goodr.com/demoted and use promo code DEMOTED for Free Shipping! Join the Salesblazer Community at https://sforce.co/demoted
Where do you draw the line between work and life? Writer Simone Stolzoff explores the problem with defining yourself by your job — and shows what it takes to reclaim your time and sense of meaning beyond the office. Hosted on Acast. See acast.com/privacy for more information.
Where do you draw the line between work and life? Writer Simone Stolzoff explores the problem with defining yourself by your job — and shows what it takes to reclaim your time and sense of meaning beyond the office.
Where do you draw the line between work and life? Writer Simone Stolzoff explores the problem with defining yourself by your job — and shows what it takes to reclaim your time and sense of meaning beyond the office.
In today's episode, we're joined by Simone Stolzoff, author of “The Good Enough Job”. Simone brings incredible insight into redefining our relationship with work and finding balance in a culture obsessed with productivity. Workism: Where did America's obsession with work come from? Why it's crucial to rethink tying our purpose, identity, and worth to our work. The truth about “do what you love” – is it all it's cracked up to be? How diversifying our identity and sense of worth can transform our lives. Finding meaning and identity beyond “what you do.” Redefining success for true happiness. + SO MUCH MORE! About Simone: Simone Stolzoff is an author, journalist, and workplace expert from San Francisco. A former design lead at the global innovation firm IDEO, his work has been featured in The New York Times, The Atlantic, The Wall Street Journal, and various other publications. His debut book The Good Enough Job: Reclaiming Life from Work was the #1 bestselling work-life balance book of 2023 and has been translated into over a dozen languages. He is a graduate of the University of Pennsylvania and Stanford. To connect with Simone: simonestolzoff.com articlebookclub.substack.com IG: thepizza_bagel
What is work? And what is the role of work in our lives?For many Americans, work is a primary source of meaning and identity. But what if you embraced a more holistic identity?Today, I'm in conversation with Simone Stolzoff, author of The Good Enough Job, about the roles of work in our modern lives. Simone invites us to embrace more sides of ourselves as we write our stories and, through a broader lens on identity, be more intentional about the role of our work and the ambitions we pursue.Learn more about Simone Stolzoff:WebsiteInstagram: @thepizza_bagelThanks for Listening!If you liked this episode, please rate, review, and share the episode. Thank you so much!Get show notes for this episode at https://sustainableambition.com/podcastSend me ideas for what you'd like to hear on the podcast, or a question that might be read and answered here on the show! Email me at podcast@SustainableAmbition.comSign up for my curated bi-weekly Sustainable Ambition Forum newsletter at: https://sustainableambition.com/subscribe
In this compelling episode of the Passion Struck podcast, host John R. Miles sits down with Robert Breedlove, a leading voice in the world of decentralized finance and Bitcoin. Robert is known for his profound insights into the economic and philosophical implications of money, power, and freedom. Together, they delve into the intricacies of the war on money and explore practical strategies to protect your financial freedom in today's volatile economic landscape.Order a copy of my book, "Passion Struck: Twelve Powerful Principles to Unlock Your Purpose and Ignite Your Most Intentional Life," today! This book, a 2024 must-read chosen by the Next Big Idea Club, has garnered multiple accolades, including the Business Minds Best Book Award, the Eric Hoffer Award, and the Non-Fiction Book Awards Gold Medal. Don't miss out on the opportunity to transform your life with these powerful principles!Full show notes and resources can be found here: https://passionstruck.com/robert-breedlove-hidden-war-on-financial-freedom/In this episode, you will learn:The history of money and how gold became the standard for global tradeThe transition from the gold standard to the fiat currency paradigm after World War IIThe impact of central planning on the market for money and the global economyThe consequences of printing money and debasing currency on purchasing power and ownership rightsThe role of central banks in manipulating currency and the detrimental effects on society and civilizationThe importance of understanding the economic implications of printing money, inflation, and central bankingThe significance of property rights and ownership in the context of debasing currency and preserving civilizationThe historical context of the Bretton Woods Conference and the Nixon shock in 1971The ongoing conflict between Ukraine and Russia and the economic implications of the war effortsAll things Angela Foster: https://angelafosterperformance.com/SponsorsBrought to you by Clariton, fast and powerful relief is just a quick trip away. Ask for Claritin-D at your local pharmacy counter. You don't even need a prescription! Go to “CLARITIN DOT COM” right now for a discount so you can Live Claritin Clear.--► For information about advertisers and promo codes, go to:https://passionstruck.com/deals/Catch More of Passion StruckCan't miss my episode with Jeffrey C. Walker On The Criticality of Collaboration in Systems ChangeMy solo episode on Why Hustle Culture Is Toxic (And How to Break Free From It)Listen to my interview with Simone Stolzoff on the Amazing Art of Finding Work-Life HarmonyWatch my episode with Douglas Rushkoff on Survival of the Richest: Don't Believe Their MindsetCan't miss my episode withSeth Godin on Why We Need Systems Change to Save the PlanetLike this show? Please leave us a review here-- even one sentence helps! Consider including your Twitter or Instagram handle so we can thank you personally!
Simone Stolzoff, author and workplace expert, discusses the many ways work has taken on an outsized role in our lives, what it's costing us, and exactly how to fix it. 3 science-backed ways to become more comfortable with uncertainty How to overcome burnout Why people in the US care more about work and work way harder than people in other countries What we can learn from other countries about work/life balance (and how to actually apply those learnings in the US) Exactly what to do if you're a writer, teacher, zookeeper, or any other job that's societally lauded but not paid accordingly How to work less without worrying about losing your job How to know if you should make your passion your job Why time sanctuaries will make you more productive + way happier Secrets to WAY more workplace satisfaction, whether you work for a company or yourself And so much more For more from Simone, you can find him on Instagram at @thepizza_bagel or his website www.simonestolzoff.com. The Good Enough Job: Reclaiming Life from Work is available where books are sold. To join The Liz Moody Podcast Club Facebook group, go to https://www.facebook.com/groups/thelizmoodypodcast. Ready to uplevel every part of your life? Order my new book 100 Ways to Change Your Life: The Science of Leveling Up Health, Happiness, Relationships & Success now! This episode is sponsored by: Puori: go to puori.com/LIZMOODY and use promo code LIZMOODY for 20% sitewide. YNAB: go to www.YNAB.com/LizMoody to get one month free. Cymbiotika: use code LIZMOODY on cymbiotika.com to get 15% off plus free shipping on subscription orders. Pique: go to piquelife.com/LIZMOODY for 15% off plus a special gift. Bon Charge: visit boncharge.com and use promo code LIZMOODY to get 15% off, plus free shipping and a 12-month warranty. Previous episodes referred to in this episode: The Science Of Cravings + 3 Steps to Break Unwanted Habits with Dr. Jud Brewer Neuroscience Hacks For Creating Your Dream Life with Dr. Tara Swart Bieber How To Eliminate Bloat & Constipation (+ SIBO, IBS, Parasites, Period Poops & More) with Tamara Duker Freuman, MS, RD, CDN The Liz Moody Podcast cover art by Zack. The Liz Moody Podcast music by Alex Ruimy. Formerly the Healthier Together Podcast. This podcast and website represents the opinions of Liz Moody and her guests to the show. The content here should not be taken as medical advice. The content here is for information purposes only, and because each person is so unique, please consult your healthcare professional for any medical questions.
In this inspiring episode of the Passion Struck podcast, we have the pleasure of hosting Simone Stolzoff, a visionary author and advocate for work-life balance and career fulfillment. As the author of "The Good Enough Job," Simone challenges conventional notions of work and identity, urging us to redefine our perspectives and pursue a balanced and fulfilling life. Want to learn the 12 philosophies that the most successful people use to create a limitless life? Pre-order John R. Miles's new book, Passion Struck, which will be released on February 6, 2024. Full show notes and resources can be found here: https://passionstruck.com/simone-stolzoff-finding-work-life-harmony/ Simone Stolzoff on How You Create Work-Life Harmony In our interview, Simone Stolzoff offers listeners a fresh perspective on the ever-elusive quest for a fulfilling career. Drawing from his insightful research and the wisdom he shared during our conversation, Stolzoff challenges the prevailing notion that work should be the sole source of our identity and happiness. Sponsors Brought to you by OneSkin. Get 15% your order using code Passionstruck at https://www.oneskin.co/#oneskinpod. Brought to you by Indeed: Claim your SEVENTY-FIVE DOLLAR CREDIT now at Indeed dot com slash PASSIONSTRUCK. Brought to you by Lifeforce: Join me and thousands of others who have transformed their lives through Lifeforce's proactive and personalized approach to healthcare. Visit MyLifeforce.com today to start your membership and receive an exclusive $200 off. Brought to you by Hello Fresh. Use code passion 50 to get 50% off plus free shipping! --► For information about advertisers and promo codes, go to: https://passionstruck.com/deals/ Like this show? Please leave us a review here -- even one sentence helps! Consider including your Twitter or Instagram handle so we can thank you personally! How Connect with John on Twitter at @John_RMiles and on Instagram at @john_R_Miles. Prefer to watch this episode: https://youtu.be/hW6iKb_LNUA Subscribe to our main YouTube Channel Here: https://www.youtube.com/c/JohnRMiles Subscribe to our YouTube Clips Channel: https://www.youtube.com/@passionstruckclips Want to find your purpose in life? I provide my six simple steps to achieving it - passionstruck.com/5-simple-steps-to-find-your-passion-in-life/ Want to hear my best interviews from 2022? Check out episode 233 on intentional greatness and episode 234 on intentional behavior change. Learn more about John: https://johnrmiles.com/
In this inspiring episode of the Passion Struck podcast, we have the pleasure of hosting Simone Stolzoff, a visionary author and advocate for work-life balance and career fulfillment. As the author of "The Good Enough Job," Simone challenges conventional notions of work and identity, urging us to redefine our perspectives and pursue a balanced and fulfilling life. Want to learn the 12 philosophies that the most successful people use to create a limitless life? Pre-order John R. Miles's new book, Passion Struck, which will be released on February 6, 2024. Full show notes and resources can be found here: https://passionstruck.com/simone-stolzoff-finding-work-life-harmony/ Simone Stolzoff on How You Create Work-Life Harmony In our interview, Simone Stolzoff offers listeners a fresh perspective on the ever-elusive quest for a fulfilling career. Drawing from his insightful research and the wisdom he shared during our conversation, Stolzoff challenges the prevailing notion that work should be the sole source of our identity and happiness. Sponsors Brought to you by OneSkin. Get 15% your order using code Passionstruck at https://www.oneskin.co/#oneskinpod. Brought to you by Indeed: Claim your SEVENTY-FIVE DOLLAR CREDIT now at Indeed dot com slash PASSIONSTRUCK. Brought to you by Lifeforce: Join me and thousands of others who have transformed their lives through Lifeforce's proactive and personalized approach to healthcare. Visit MyLifeforce.com today to start your membership and receive an exclusive $200 off. Brought to you by Hello Fresh. Use code passion 50 to get 50% off plus free shipping! --► For information about advertisers and promo codes, go to: https://passionstruck.com/deals/ Like this show? Please leave us a review here -- even one sentence helps! Consider including your Twitter or Instagram handle so we can thank you personally! How Connect with John on Twitter at @John_RMiles and on Instagram at @john_R_Miles. Prefer to watch this episode: https://youtu.be/hW6iKb_LNUA Subscribe to our main YouTube Channel Here: https://www.youtube.com/c/JohnRMiles Subscribe to our YouTube Clips Channel: https://www.youtube.com/@passionstruckclips Want to find your purpose in life? I provide my six simple steps to achieving it - passionstruck.com/5-simple-steps-to-find-your-passion-in-life/ Want to hear my best interviews from 2022? Check out episode 233 on intentional greatness and episode 234 on intentional behavior change. Learn more about John: https://johnrmiles.com/
Today on The Sunday Story, author Simone Stolzoff discusses his book The Good Enough Job: Reclaiming Life from Work, about our complicated relationship with work. Stolzoff explains how as jobs have changed over generations, so has the meaning we derive from working. Stolzoff shares his findings on our modern relationship with work and ways we can find more balance in our lives.