How to Stop Waiting for the "Right" Moment to Invest (with Simone Stolzoff)

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. Chapters: 00:00 Why uncertainty is your biggest career advantage 01:15 Introducing Simone Stolzoff and the new book 03:38 How our brains are wired to crave certainty 06:20 Why waiting for certainty causes financial paralysis 08:27 The two types of bad decision-makers 09:25 Jeff Bezos's one-way vs. two-way door framework 11:00 How to know when you've done enough research 12:41 From "The Good Enough Job" to "How to Not Know" 15:04 Why uncertainty is at an all-time high right now 16:00 How smartphones killed our tolerance for the unknown 19:43 Financial nihilism and Gen Z opting out of saving 21:00 Why "certainty anchors" matter for your finances 24:40 How to take back agency in the age of AI 25:26 Men, gambling, and financial nihilism 27:26 3–5 habits to build comfort with uncertainty 30:14 Trusting your future self to handle future problems 32:37 Where to find Simone and the book Resources & Links: 📖 Ready to turn your savings into a paycheck that lasts a lifetime? Pre-order Jean's new book, The Forever Paycheck, out September 9th: https://www.penguinrandomhouse.com/bo... 🧠 Join the HerMoney InvestingFixx Club: https://join.investingfixx.com/ 💬 Got a question for our next mailbag? Email us at [email protected] 🎧 Listen to the full episode on Apple Podcasts, Spotify, or wherever you get your podcasts: https://pod.link/1098802558 ❤️ Liked this episode? Give it a thumbs up and share with a friend who needs to hear it.