Deer Ridge Correctional Institution - My Classroom for the quarter (Photo Credit - Charles McDonald)
I've spent over two decades advising high-net-worth and ultra-high-net-worth clients. I know how to talk about estate tax minimization, concentrated stock positions, and generational wealth transfer. I built a successful career doing it, and I care about it - a lot.
But a few weeks ago, I walked into a classroom at a state correctional facility to teach personal finance—and realized how much I didn't know.
The comfort of expertise
I recently read Range by David Epstein. The book proposes that In a world that rewards specialization, generalists—people who explore widely before going deep—often thrive in ways that specialists can't. They're better at adapting, connecting ideas, and solving unfamiliar problems. This idea has been rolling around in my head ever since I agreed to teach this class.
I'm a specialist. I've spent my career becoming an expert in the financial concerns of people with significant assets. But leading up to the class, I was mentally preparing for the idea that my knowledge wouldn’t transfer the way I expected.
As early as day 1, they weren't asking about Roth conversions or even simple asset allocation. They were asking about things I'd rarely had to consider in my professional life:
- How does bankruptcy actually work, and what happens after?
- What are the traps in subprime lending?
- How do you rebuild credit from nothing?
- What does it mean to be "unbanked," and how do you re-enter a financial system with roadblocks designed to keep you out?
I didn't have all the answers. So I did what I ask my own clients to do: I got honest about what I didn't know, and I went to work learning it.
Curious, not judgmental
Before any of that learning could happen, I had to check something at the door: my own judgment.
I made a decision before my first session. When I walked into that classroom, I was going to see people—human beings who, at some point, made a bad choice. That's it. Not a category, not a label. People.
I'll borrow a line from Ted Lasso here: be curious, not judgmental. It sounds simple, but it isn't. We're wired to size people up, to sort them, and then decide who's worth our attention and who isn't. Letting go of that—walking in with genuine curiosity instead of quiet assumptions—takes real effort.
But when I did, something shifted. The students relaxed. And so did I.
Money is personal—everywhere
That openness paid off in a way I didn't expect.
I assumed my students would be guarded. Talking about money is hard enough in comfortable settings. I've watched wealthy, successful people struggle when asked to be honest about their financial fears. I figured a prison classroom would be an even tougher place to build that kind of trust.
I was happily surprised.
I did my best to create a judgment-free space. I wasn't there to lecture them about their past, but to help them build something different. And when that happened, they opened up. They shared their struggles, their regrets, and their hopes with an honesty and openness I don't always see in my professional practice.
It turns out money is deeply personal no matter who you are or where you sit. The dollar amounts change, but the emotions don't.
Helping people see a future
The most rewarding part hasn't been teaching the mechanics—how compound interest works or how to build a budget. They have taken to those lessons with enthusiasm, but the most enjoyable part has been watching students start to believe they have a future worth planning for. I started the first week with the quote from Eisenhower - that ‘Plans are useless but planning is indispensable.’ My goal was not to have them get the numbers exactly right, but to go through the mental exercise of thinking about the future and to have the tools and knowledge to navigate the financial world after they are released.
Many of them haven't been given permission to think that way. When you're marginalized by a system—whether it's the justice system, the banking system, or simply an economy that wasn't built with you in mind—it's hard to imagine that financial planning is even for you.
Planning isn't a luxury reserved for the wealthy. It's a process for anyone willing to imagine a better version of their life and to learn the tools that help them move toward it.
Giving my students that process—and the confidence to use it—has been some of the most meaningful work I've done.
What I'm taking back to my practice
I didn't start teaching this class to become a better advisor. I did it because I believe financial literacy should be accessible to everyone, not just the people who can afford my services. This was all supposed to be a side hustle.
But it's made me better anyway.
I have more empathy. I understand more corners of the financial world than I did a few weeks ago. And I've been reminded that the fundamentals of this work—listening, withholding judgment, building trust, helping people see a path forward—matter just as much for someone rebuilding from nothing as they do for someone protecting a fortune.
Range argues that the people who venture outside their lane often come back with something valuable. I believe that now that I’ve experienced this transformation first hand.
Stepping outside my comfort zone didn't make me less of a specialist. It made me a more complete one. And being curious instead of judgmental didn't just help my students—it made me better at seeing every client, and every person, a little more clearly.