Why Generalists Win: Lessons from Range for White-Collar Defendants

In this post, I’m sharing my thoughts on Range by David Epstein. I found it valuable, especially for those navigating a white-collar crime investigation. I recommend it, and if you don’t have time to read or listen to the book, I hope this summary helps you.

Why Broader Experience Matters

Epstein argues that in today’s complex world, those with broader experiences—generalists—can be more successful than those with a deep specialization. This hit home for me because when I came home from federal prison in 2009, I had to start over. I was no longer a stockbroker or a real estate agent. I had to try many things, and at times, I thought, “This isn’t going to work,” but it was still making me better. If you’ve lost your licenses or you’re rebuilding after a conviction, here’s some good news: the broader you are, the more things you try, the more successful you can be.

Federer vs. Woods: Diverse Skills Matter

In Range, Epstein talks about Tiger Woods and Roger Federer. Woods was all about golf—nothing else. But Federer played many sports before honing in on tennis. Epstein argues that Federer’s diverse background helped him develop a wider range of skills, both physically and mentally. That’s a great lesson for people going through a white-collar crime investigation. It’s tempting to think you can only return to what you’ve known, but this can limit you. For example, I know someone in our community—a lawyer—who’s struggling because he thinks he can only earn a living with his law license. That kind of singular focus is delaying his plea agreement and affecting his decisions. The truth is, you can be successful without the career you once had. You just need to embrace trying new things, and in time, you’ll hone in on something new.

Thriving in Wicked Environments

Epstein contrasts two types of environments: kind learning environments, where the rules are clear and feedback is immediate, and wicked environments, where conditions are always changing, and feedback is delayed or ambiguous. You could say federal prison is a kind learning environment—you know when you’re going to eat, when you stand for count, when you can visit. Out here, it’s more of a wicked environment. People might tell you what you want to hear, or say they’ll help you and then they don’t. Generalists, Epstein argues, thrive in wicked environments because they don’t freak out with uncertainty. This was a big takeaway for me. When I came home, I had to try a lot of things and adapt. Speaking in front of different crowds, adjusting on the spot—sometimes it didn’t go well, but I kept trying. I learned what worked and what didn’t, and that made me better.

The Limits of Grit: Knowing When to Pivot

One important lesson in Range is that grit—persistence—isn’t always the answer. Sometimes, you have to know when to pivot and try something new. I’ve experienced this firsthand. After federal prison, I built a very lucrative speaking career. But in 2014, I walked away from it, even though it was generating hundreds of thousands of dollars a year, because I knew there was a better way forward. You’ve got to recognize when to pivot and not be so obsessed with a specific outcome that you miss other opportunities.

Using Your Past Skills in New Ways

Epstein talks about “far transfer”—applying skills from one field to another. This is huge. Just because you’re no longer working in the career you had doesn’t mean your skills are gone. They’re still valuable, just in different ways. When I came home from federal prison, I wrote blogs for real estate agents and discovered a love for marketing. You might have to apply your skills differently, but they’re still there, and they can help you succeed.

Escaping Groupthink: Making Your Own Decisions

Another key point in Range is avoiding groupthink. In federal prison, and even outside of it, you’ll meet people who tell you what you can’t do. I heard it all the time: “You can’t build a business after prison,” “You can’t become a multimillionaire again.” If I’d listened to them, I wouldn’t be where I am today. Don’t be afraid to challenge conventional wisdom and think differently. Make your own decisions, even if people think you’re crazy. The more people called me crazy, the more I knew I was on to something.

The Dignity in Trying and Failing

At the end of the day, Range teaches that trying new things, embracing failure, and learning from those failures are essential. When I came home, I failed plenty of times—but every failure made me better. If you’ve pled guilty, it’s natural to feel like you’ve failed, but this is an opportunity to build something new. Don’t be afraid to start over, to try, and to fail. There’s dignity in trying and failing because it makes you stronger and better equipped to handle the next challenge.

Thank you for being part of our White Collar Advice community. I hope this book report helps you as you move to the next phase in your journey.

Justin Paperny

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