As an economist, Russ Roberts has been taught to approach decision-making by conducting an analysis, weighing tradeoffs, and then rationally budgeting resources to get the most bang for his buck. But as he explains in his new book, Wild Problems: A Guide to the Decisions That Define Us, he found this approach woefully inadequate for grappling with life’s biggest decisions — things like figuring out whether to get married or how to live a meaningful life. Today on the show, Russ and I delve into why the pros and cons approach to decision-making is inadequate when facing what he calls “wild problems.” Russ explains that what makes life’s big decisions so difficult to deal with is the fact that we don’t know what they’ll be like before we make them, the decisions themselves will transform us into different people, and their effects can be permanent, making such decisions akin to choosing to become a vampire. From there we turn to strategies for dealing with the inherent uncertainty around wild problems, including looking beyond basic happiness, considering tradition, and trying things out by experience.

Being adept at discerning people’s true thoughts and intentions is a valuable skill to have. Knowing when someone is deceiving you can protect your finances, your professional interests, and your loved ones. Here to teach us some of the elements of this skill is Dr. David Lieberman, who’s a psychotherapist, a consultant to the military and other intelligence and defense agencies, and the author of Mindreader: The New Science of Deciphering What People Really Think, What They Really Want, and Who They Really Are. Today on the show, David explains why verbal cues offer a better window into people’s minds than body language, and the clues to look for in both spoken and written speech that can indicate whether someone is honest or deceptive. We also get into how to detect whether someone is mentally healthy or not, including the signs that you’re dealing with a psychopath.

No kid forgets getting his first bike, nor the surge of independence he felt the first time he pedaled away from his parents. And even as adults, the bike seems to give off a feeling of romance, of freedom, and, when you get going fast enough, even of flying. The special allure of the bicycle can really be traced back to its simple yet elegant design, and my guest today will unpack the intriguing history of its creation. His name is Jody Rosen, and he’s the author of Two Wheels Good: The History and Mystery of the Bicycle. Today on the show, Jody explains the origins of the bicycle’s design, including how it was an anachronism at its birth, may have been inspired by a volcanic eruption, and helped liberate mankind from dependence on draft animals for transportation and exploration. We also get into how the bicycle was associated with flight right from the start. Along the way, we discuss how cycling represents an uncanny fusion of man and machine and produces a set of one-of-a-kind pleasures. This episode will make you want to mount your trusty bicycle steed and take a ride.

Do you feel stuck in life? Inwardly you keep repeating the same thoughts, outwardly you keep repeating the same routine, and on and on a cycle of unhappy disappointment goes. To break the cycle, maybe what you need to do is watch a film that has become synonymous with this kind of stuck-ness — Groundhog Day — which my guest says contains the roadmap to escaping a life lived on autopilot. His name is Paul Hannam, he’s the author of The Wisdom of Groundhog Day: How to Improve Your Life One Day at a Time, and today on the show, Paul unpacks the deeper philosophical layers of what’s considered one of the best movies of all time. Paul explains how the film teaches us that to escape the ruts of what he calls the “Groundhog Day condition,” we must first make an inner change where we learn to approach life in a more grateful, present-focused, engaged way. From there, we can embrace the film’s unique strategy for change, which is to experiment with doing something new every day, thereby refining and improving our lives through the process of trial, error, and progressive improvement.

When we think about people who can live anywhere, we tend to think about corporate-employed remote workers and online entrepreneurs. But many other kinds of professionals, from teachers to doctors, could hypothetically find a job anywhere, and thus live anywhere they’d like. If you’re what my guest Melody Warnick calls an “anywhereist” and have seriously or casually considered moving somewhere else, today we’ll talk through the factors to consider in making that decision. Melody is the author of If You Could Live Anywhere: The Surprising Importance of Place in a Work-From-Anywhere World, and in today’s conversation we discuss the factors that you should include in what she calls a “location strategy,” from the cost of living in a place to whether it allows you to build the kinds of relationships you’re looking for. We also talk about how the place you live can be part of your purpose in life and the elements that contribute to an overall quality of life.