How 20 Years of Poverty Shaped a Former Monk’s Approach to Wealth Management

Doug Lynam has one of the most unusual career paths in finance. After serving as a Marine officer and spending 20 years as a Benedictine monk, he became a registered investment advisor (RIA), launching his practice from inside the monastery. His unconventional journey earned him a profile in The New York Times, which led to a two-book deal with HarperCollins.

His first book, “The Monk and the Riddle,” taught basic financial principles through monastic wisdom. His latest, “Taming Your Money Monster,” digs deeper into why people make destructive financial decisions despite knowing better. The secret, Lynam argues, lies in the Enneagram, an ancient personality system that Lynam adapted to identify what he calls “money monsters,” the anxious or avoidant patterns that sabotage our finances.

We spoke with Lynam about his journey and how understanding your personality type can transform your relationship with money.

An Unlikely Financial Journey

Editor: Your career path is one of the more unique ones you’ll encounter, given your journey from being a Marine to being a monk to managing people’s money. How did you make these transitions? What’s kept you going through those?

Lynam: The story for all of us starts in childhood. I grew up in a relatively affluent upper-middle-class family, and my father was the CEO of an oil company, then a chemical company. But [then] my parents divorced, when I was about seven or eight, money became weaponized. It became the tool my parents used to get back at each other, often putting us kids in the middle. You’d ask your dad for something and he’d say, “Go ask your mom, she’s got all my money.” Ask your mom and she’d say, “Your dad’s got all the money.” And so, I developed what I would call a very avoidant style toward money. I had a real negative reaction to it, to the world of business and capitalism and all of it.

Editor: But you ended up managing money anyway—from inside the monastery?

Lynam: One of the ironies is that I went there to escape the world of money and materialism, to really flabbergast my parents, and find God. But it turned out that everybody in the monastery hated money as much as I did. And so we were all very money avoidant. And so if everybody in your community hates dealing with money, eventually that’s going to lead to problems, and it did. Our community went through bankruptcy. I was the most junior monk in the community by many years—I was the grunt—and I rather foolishly raised my hand and said, “I’ll take that one on.”

At the time, I was in a teaching order. I was teaching math and science at a prestigious private school, and I realized that we were sending our kids into the world as financially illiterate, and that was setting them up for a lot of hardship and failure. Why are we teaching them the quadratic formula, but not teaching them compound interest? It seems like this is equally important.

I always like to give the kids hands-on, real-world practical stuff rather than just lecturing. The first thing I did is I opened up the school’s endowment to show them how endowment works. That was fine. And then I opened up the school retirement plan to show them how that worked. And it was a train wreck. We had high fees. We had poor fund performance. There was no fiduciary oversight. I wanted to find a company that would offer really good fiduciary oversight and couldn’t find it. I was looking to transition out of the monastery and for another career where I see a problem in the world I feel passionate about, and that I could solve. And out of that bizarre, absolute absurdity, I started my own investment advisory service. I became a licensed RIA and got my own company going from inside a monastery.

Editor: How did that lead to your books?

Lynam: After I left the monastery and launched my business full-time, I was fortunate enough to merge my little startup with a larger company here in Santa Fe, Longview Asset Management. They took me under their wing. And then the first day of work, an article about me hit the New York Times. And then I got this two-book deal from Harper Collins. 

Why Talking About Money Is Harder Than Talking About Sex

Editor: In working with clients, what did you discover about people’s money problems?

Lynam: It’s easier to talk about sex than money. You can’t talk to people about their financial life without it—everyone’s bank statement is a bread crumb trail back to their deepest neurosis. And they want to talk about it and share what often feels like guilt, shame, anger, or whatever fear that’s been nagging at them their whole life.

Editor: That insight led to your second book about personality types and money. Why the Enneagram specifically?

Lynam: If I know a client’s Enneagram type, it’s the first thing in my file. If you’re in the anger triad, you’re looking for control and empowerment. Shame types look for validation and connection, and fear types look for security. I know how to talk to you in a way that’s going to put you at ease, and it’s going to help you feel good about yourself and what I’m offering you.

Editor: You identify 18 different “money monsters.” How does this work in practice?

Lynam: There are nine core personality types, two money monsters for each, and now there’s the pattern sitting in front of you. Whether you’re anxious or avoidant is the big insight that people tend to fall into those camps. And then that anxiety or that avoidance expresses itself in a unique way, depending on what your greatest fear is.

I’m basically layering on top of the Enneagram what I’m calling the attachment theory of money, which is just me plagiarizing the attachment theory of relationships. We can either be anxiously attached to money, too acquisitive, too obsessed, too greedy, the Gordon Gekkos of the world, or we reject it entirely. Like I did, going to the monastery. 

Overcoming Bad Financial Patterns

Editor: You write that you’re a Type Three Achiever. How has understanding that changed your relationship with money?

Lynam: Your Enneagram type is the water you’ve been swimming in your whole life, but you don’t know it because you’ve never been able to experience what it’s like outside of that. What the Enneagram tells you at its core is what your greatest unconscious fear is.

My greatest fear is of being worthless. That’s my fundamental, deepest psychological wound. And so my ego is designed to try to assuage that sense of worthlessness by always trying to achieve something in the eyes of others. With money, I equate unconsciously my net worth with my self-worth. And so if my net worth is low, my self-worth then goes low, and then I don’t want to look at my net worth. I don’t want to look at the bills. I don’t want to look at the taxes because it triggers that sense of worthlessness.

Editor: What’s your process for helping people overcome these patterns?

Lynam: We need to look at your earnings, your savings, your investments, and your giving. And then, where are your money monsters showing up? Naming something helps a lot. And once you get to that step, a lot happens pretty quickly. And then it’s figuring out, well, where are your weaknesses and how do we help you overcome them?

The earnings part, you largely have to figure out for yourself. Then the savings part, we can work on that together, first by bringing conscious awareness to it and slowly getting better over time. So, contemplation is the first part. Compassion is the second part—compassion to yourself and compassion to people around you. Third, there’s action, which will be customized for each person. So, if you’re using your money to feed your worst neurosis and that’s what’s fundamentally causing the root issue behind most of your money issues, and you can tackle that, then you’ve addressed the root cause of the problem, not just the symptoms.

Connecting Your Money and Your Values

Editor: How do you help people connect their money decisions to their values?

Lynam: The important thing is that you’re living according to your values, not my values. And that’s a real distinction. I help you to articulate what your values are, not imposing mine on you. And then once you’ve articulated those, then we can think about, well, what’s your investment strategy that helps you, that supports that? What’s your giving strategy? Maybe you’re in the wrong line of work. Maybe you’re in a career that’s killing your soul because it’s not aligned with your values. That’s a very common problem.

The ultimate goal is for you to see how you use your wealth as a tool for love and service to a suffering world. That’s the real question. What’s the crack in the world that God put you on this planet to help fix? What are your gifts and tools, and how can you take your time, your talent, your wealth, your treasure, and make the world around you a little bit better? 

This interview has been edited and condensed for length and clarity.