We’re living in a moment of profound financial uncertainty. Tariffs are fluctuating by the week, inflation is still running hotter than the Fed would like, AI is reshaping entire industries overnight, and mortgage rates aren’t expected to dip below 5.8% before 2030. And according to the Economic Policy Uncertainty Index, the five highest spikes in uncertainty since researchers began collecting data in the 1980s have all occurred in the last five years.
So it might feel like the last thing you need right now is someone telling you to get comfortable with not knowing. But that’s exactly what Simone Stolzoff argues in his new book, How To Not Know: The Value of Uncertainty in a World That Demands Answers. Stolzoff joined Jean Chatzky on the HerMoney podcast to talk about why our desperate search for certainty is making us worse investors, worse decision-makers, and more anxious, and what we should be doing instead.
Here’s what we learned.
Doing Nothing Is Never the Safe Option
Jean Chatzky made a point that Stolzoff echoed throughout the conversation: in investing, inaction carries its own risk. If you don’t put your money to work, you face inflation risk. You lose time. You lose compounding.
Stolzoff describes two patterns he sees in people who are particularly intolerant of uncertainty: obsessive information-gathering and impulsive decision-making. Neither serves you well. “Maybe there’s a middle road where you gather some information, but you don’t let that completely paralyze you,” Stolzoff says.
He also shares his framework for knowing when you’ve done enough research: making decisions when you’re about 75% ready — because if you’re waiting until you’re 100%, it’s usually too late.
“When I am asking everyone I know whether I should take job A or job B, and my Uber driver and my yoga teacher; if it feels like I’m no longer gathering new information and it just feels like I’m trying to get validation in some of my prior assumptions, I’ve probably gone too far,” Stolzoff says.
Trust Your Future Self
The most resonant idea in the book — and the one most directly relevant to retirement planning — is the concept of trusting your future self to handle future problems.
Stolzoff shares the story of his friend Emily, whose mother received a terminal diagnosis. A family friend who was an oncology doctor offered her this: “The version of yourself that will handle that tragic event if or when it occurs will be born into existence in that moment, and that version of you will have more context, more information, and be better equipped to deal with it than the version of you today. You have to trust in your future self to be able to handle your future problems,” Stolzoff says.
For women who are lying awake, wondering whether they’ve saved enough, whether their retirement plan will hold, whether they’ll outlive their money, this reframe matters.
Chatzky added her own version: look back at hard things you’ve already survived and use that as evidence. And Stolzoff agrees: “That’s what it means to cultivate faith. It’s to build the case for why you should keep going.”
Three Ways to Get More Comfortable With Uncertainty
Stolzoff closes with a practical roadmap for building the capacity to be comfortable with financial uncertainty.
Find your anchors. “When we are certain about some facets of our life, it makes it easier to hold uncertainty in others,” Stolzoff says. A consistent savings habit, a fully funded emergency fund, and an investment account you contribute to automatically; these create the stable ground that makes everything else feel more manageable.
Choose curiosity over fear. Our instinct is to catastrophize and to run through everything that could go wrong. Stolzoff also suggests asking: what if things go right?
Trust your future self. The most important skill in a rapidly changing economy, Stolzoff says, is “your ability to walk into an unknown situation, to trust in your future self’s ability to reinvent yourself or to adapt.”
