Several years ago, I found myself standing at MEA’s Santa Fe ranch campus (before it opened) with Chip Conley and Richard Rohr, wrestling with writer’s block around my next book on finance. Chip, with that twinkle in his eye that usually precedes something profound (or curiously dangerous), asked me a question that would change my life: “If you were in therapy with your money, what would your money say to you? And what would you say to your money?”
That question hit me like a two-by-four upside the head.
Along with some gentle nudging from Richard (who introduced me to the Enneagram), it became the seed for my new book, Taming Your Money Monster: Nine Paths to Money Mastery With The Enneagram, which was released through HarperCollins on July 8th. As a former Marine, a Benedictine monk for twenty years, and then a money manager, I’ve been on some wild adventures—but this book journey topped them all.
When Chip posed that question, I was deep in what he calls the “messy middle” of life. My marriage was crumbling (it later ended in divorce), I was pivoting careers (again!), and I was battling addiction. My middle felt more like The Dark Night of the Soul—an existential crisis so profound that I lost my connection to everything, including my faith.
I needed to dissolve my old ego identity before something new and better could emerge. What popped out of that chrysalis wasn’t what I expected, but something more gentle and beautifully flawed than what went in. Turns out, transformation isn’t about becoming someone else entirely—it’s about becoming more authentically yourself, wounds and all.
One of my biggest takeaways from Chip’s question is that money isn’t just about dollars and cents—it’s about our deepest fears, our wildest hopes, and our journey toward wholeness. The Enneagram (an ancient personality system that identifies nine core ego types) helped me understand that our childhood wounds create specific patterns around money that keep us stuck. My book explores how understanding your personality type can transform your financial life from a source of stress into a pathway to material and spiritual growth.
The journey from that initial question to publishing this book has been transformative—and occasionally as comfortable as sitting on a cactus. It’s taught me that our “money monsters”—those destructive financial patterns we all have—aren’t enemies to be vanquished but wounded parts of ourselves crying out for healing. They’re just trying to protect us in the only way they know how, even when their methods are about as effective as using a squirrel to guard your nuts.
By understanding how our personality affects our relationship with money, we can transform our financial lives from a battlefield into a training ground for spiritual growth. When we heal those old wounds and practice healthier patterns, we access our best qualities to share with the world.
Fortunately, I was also part of the first cohort of MEA’s Navigating Transitions (TQ) coaching certification program. Talk about perfect timing! The program helped me navigate my own messy middle while giving me tools to guide others through their struggles. Chip managed to distill his lifetime of wisdom into this course, and the results are extraordinary.
As I launch Taming Your Money Monster into the world, I’m filled with gratitude for that afternoon with Chip and Richard, for the MEA coaching program, and for all the messy moments that brought me here. Sometimes the most profound transformations start with a simple question—we just have to be brave enough to answer it honestly.
-Doug
Doug Lynam is a former Marine, Benedictine monk, and money manager and author of From Monk to Money Manager: A Former Monk’s Financial Guide to Becoming a Little Bit Wealthy—And Why That’s Okay and Taming Your Money Monster: Nine Paths to Money Mastery with the Enneagram. Contact him at [email protected] or via douglynam.com.