Even if all you care about is having a good time during all-too-short time on this earth, you will struggle to anticipate what it is that will bring delight, pleasure, contentment. And most of us care about more than just having a good time. We would like to find purpose and meaning.

Russ Roberts

One of the best things about the internet is that you can access mentors without needing to use any of their time. One of my “digital mentors” for more than fourteen years has been Russ Roberts.  Through his weekly podcast, Econtalk, I learned more about a wide range of topics while also getting to see inside the mind of an older and wiser man committed to personal growth and evolution.

This is what made reading Wild Problems, his latest book, so delightful. It wasn’t just a book about making better decisions in life. It was the book of someone I had gotten to know over the years, and more specifically, someone that went through an evolution in how he saw the world.  

When I first started listening to the podcast, I found Russ’ perspective intoxicating. He challenged guests with the intense rationality you would expect of an economics professor. When guests made weak or speculative claims he would push back. He pushed the conversation toward what he thought was the truth, calling out instances of confirmation bias and motivated reasoning.  At the time, I was at the start of a promising consulting career, and turning facts and information into powerful and persuasive stories seemed to be the formula to make the world a better place. 

Over the years, however, Russ started to soften his attachment to this stance and his evolution is probably what kept me interested.  He started to talk more about his connection to religion and reflect on how he wasn’t as sure about things as when he was younger. And this was at the same time as many people were shifting into a state of perma-outrage, amplified by the election of Trump and the growing efforts of media platforms to remain relative.  While most of the world seemed to pair moral goodness with the ability to maintain outrages, Russ’ reflective natured offered a welcome alternative, as he seemed to lean more into other virtues like curiosity and humility on his podcast.

That deeper, reflective Russ fills the pages of Wild Problems which is what made reading it so enjoyable. It was less a how-to guide for decision-making and more of a poetic contemplation of what matters in life (also my favorite kind of book).

Wild Problems are About Who We Might Become

Early in the book, Russ defines what he means by “wild problem,”: 

a fork in the road of life where knowing which path is the right one isn’t obvious, where the pleasure and pain from choosing one path over another are ultimately hidden from us, where the path we choose defines who we are and who we might become. Wild problems are the big decisions all of us have to deal with as we go through life.

In 2016, I faced a wild problem just like this and it seemed as if there were two paths:

  • Path #1: Continue on my current path in management consulting, one that I had less and less desire to stay on by the day. Yet if I continued on the path, I would never face any financial difficulty and I would continue to have broad approval of my life decisions from everyone in my life
  • Path #2: Quit my job and try to make it work as a freelance consultant (read: I really just wanted to escape and didn’t have much of a plan)

This was my old wild problem but it’s only upon reflection that I realize I didn’t really look at it the right way. If you’ve read my writing you know that I chose path #2. But it was not because as Russ suggests, that I had a sense that the decision was about “who we are and who we might become.”

I had no conception of the upsides of taking my path. I only knew that on my previous path, the odds seemed far too high that I was becoming a person I didn’t want to be.  That was enough for me. I walked away despite people reminding me of all the downsides.  They would ask me: “Aren’t you worried about XXX….” Insert your favorite worry: money, healthcare, employment status, approval.  I worried about all these things but I sensed there was more to life and I had to find out what I had been missing.

The interesting thing about my shift is that I had almost no model of the potential upsides of taking this leap Almost all the people around me and society at large had conceived of what I was doing as a very risky thing.  I had very little support and the first couple of years were quite hard. Yet five years later it’s clear that not only were there upsides, they are far beyond what I could imagine.  A sense of aliveness, a re-awakened creative impulse, and a more optimistic stance are all things that make my current path “worth it” and it’s hard to imagine giving these up anymore. 

This is what makes these kinds of decisions wild problems.  No matter how hard we try we can never rationally determine a “correct” decision.  Nor can we ever imagine the future potential good things that might emerge, especially those that we lack in our current state. As Russ puts it, “You can’t anticipate what you’re going to enjoy, and you certainly can’t imagine some of the deeper pleasures that define us beyond the narrow day-to-day experiences of life.”  

Why are these upsides so hard to imagine? Russ makes an interesting observation about marriage that may apply to other hard decisions: 

the willingness of married people to share the experience of marriage is quite rare. First, it’s intensely personal. Intimate. Second, much of the time, we who are married may have little self-awareness of how marriage changes us.

While I have written a lot about being self-employed and the positive things I have experienced, I have the sense that words can never quite convey what this really feels like.  I have thought about life paths more than most people and many people have messaged me to tell me how much my book has helped them.  Yet there is no replacement for going through things yourself and this is ultimately the challenge of living a human life. We can trick ourselves into thinking we can plan and prepare for everything but when it comes to the biggest decisions in life, we are the ones that need to take that first step.  In that sense, Wild Problems is one of the most helpful companions.

A Conversation With the World

Since 2006, Roberts has had more than 850 conversations with various guests on his podcast. If you add this up, it amounts to more than a month of his life spent in deep conversation with others. This means having conversations is something he’s thought a lot about. To him, a great conversation is, “…an emergent experience that goes in unexpected, unplanned directions.”  It is easy to see how this doubles as a powerful metaphor for life.

For me, having hundreds of literal conversations with people from all around the world through “curiosity conversations” my podcast has inspired all sorts of rabbit holes and ideas that have kept my curiosity and writing alive with energy.  I initially decided to open my calendar and let anyone book a conversation with me in 2017 as an attempt to lean against the popular productivity advice at the time that you should protect your time and monetize access.  It felt wrong and I’m glad I ignored it.  Through hundreds of conversations, I learned not only how diverse and interesting people are from all around the world but I learned to release my own expectations of myself. As I learned to go with the flow of the conversation, I was learning how to “go with the flow” in my own life as well. 

David Whyte has been a big inspiration in this regard. He also leans on the “conversation” metaphor when talking about life, talking about the “conversational nature of reality.” In his view, we are all in a dance with the universe, and only by pushing ourselves to our “frontier” can we discover what we are meant to find out about the world and our own confusing paths.

I sense Russ is channeling a similar sentiment in his discussions on conversations, whether he intends to or not. His nudge to see conversations as “an improvisation, which is an organic art, than a scripted, prefab conversation” can easily be seen as good advice for thinking about navigating life as well. 

Learning To Say Yes

It would be one thing if Russ was your run-of-the-mill professor giving a lot of this advice. But he is not. In the professor world, he is the “weirdo” in the best sense of that word. He was a podcast before it was cool, has a rap video on famous economists, works at George Mason a school famous for being a home for some of the most contrarian thinkers, and most recently, at an age when most people are happily settling into retirement, he decided to move across the world with his wife to become President of a small liberal arts school in Israel.

As he reflects in the book, “most of my proudest accomplishments came from saying yes to things that at first glance didn’t seem to fit into who I was or my pre-existing plan.” This is what has made Russ so inspiring to me. As someone that left a predetermined path at age 32, I will likely be operating without a script for the rest of my life and books like Wild Problems are a good reminder that not only am I not alone, most people are on uncertain paths.  It’s just that some people like Russ lean into it and remain curious, while others harden and become rigid as they age. 

In addition to knowing when to say yes, Russ reflects on quitting, something I think is underappreciated in today’s world.  We have a meme of “hard work” which can be incredibly valuable for people who have found the things they are excited to work on but can lead people astray when applied to the wrong things.  As he reflects, 

to know when to fold ’em and when to hold ’em is an art that is quantifiable in poker but not in life. Better to learn who you are-your strengths and limitations-and make each decision as best you can. Here is a case where having a rule-“always persevere,” or “quit when it gets too hard”-will lead you astray. In life, knowing when to persevere and when to quit is a craft to cultivate.

This is also the core theme of the book: that life is a “craft to cultivate.”  While Russ doesn’t take a stand that there is a “right” way to live, the book does suggest that by remaining curious about our life and our path, we can increase the odds that we might learn a little more than if we did not pay attention at all. 

This is hard of course. On my previous path, I existed in a state of tension where I had the urge to become a better version of myself but felt stuck within the constraints of the path I had committed to.  Only by walking away and risking blowing up my life did I realize that there were unimaginably positive opportunities that I had not imagined.  This humbled me deeply but it also made me more curious about my path and see the art of living as a meta-practice worth cultivating. 

This book is a powerful reflection on navigating life and I sense that it would be powerful for anyone who has a hunch that there is more to life. We live in a time where many people see their life through the lens of a neatly ordered path. Yet upon reflection people quickly realize that beneath the surface we have all faced ups and downs.

Wild Problems is great because Russ doesn’t give any prescriptions or answers. He merely shares his own reflections and contemplations of his own life.  At 68, Russ could have easily retired and stopped working. I imagine everyone in his life would have praised him for this.  Yet he sensed there was something more than following the default scripts that so many people are eager to follow.  He decided to move to a new country and embrace a new challenge.  He also knows he might be wrong about it being the right move. But he’s curious and wants to see where he ends up.

I think that’s pretty badass and I’m glad there are people like Russ out there.  


If you do end up reading this Russ, I just want to thank you for your silent encouragement and modeling over the years. It has been meaningful in helping me embrace my own wild problems.

+Thanks to John Hampson and Nathan Baschez for the helpful feedback on this essay!


Just published! The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here



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