45: A Reflection of Where I’ve Been and Where I’m Going

I'll be honest: 45 doesn't mean much to me. I still feel younger than I probably should. Maybe that's what happens when you spend most of your life playing rock 'n' roll, mentoring younger folks, and building things from scratch. Maybe it's what happens when you never quite followed the script that tells you what each decade is supposed to look and feel like. I didn't get married in my twenties like most people. I bought a house at 24. I dropped out of college a few months before graduating to join a punk band. I've always been a little ahead and a little behind at the same time, and I've made peace with that.

What I care about isn't the number. It's the moment. Maybe this one is worth marking.

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I grew up shaped by people who didn't know how much they shaped me. My parents gave me work ethic and drive. My Taiwanese grandparents taught me patience and presence. A youth pastor named Allen handed me a book when I was a teenager — Developing the Leader Within You — and it helped me understand something I've never stopped believing: that leadership, at its core, is about serving others.

Allen took me on mission trips to rural areas of developing nations. We built churches, orphanages, and community centers. I spent my weekends and school breaks doing that work. Later, I moved into an old church — often sleeping in the office — to help run a nonprofit, bringing construction and medical teams to communities that needed help. Looking back, I can see the thread clearly even if I couldn't name it then: I was trying to make things better for the people around me and I was always willing to go somewhere uncomfortable to do it.

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I've taken a lot of unconventional paths: I turned down multiple million dollar recording contracts because I thought they were exploitative. I helped start The Slants, which became the defining project of the last two decades of my life. Last year, my partner and I sold our home and nearly everything in it to become minimalist nomads. We took a road trip, took a detour, and ended up in Nova Scotia. Next, we're moving to Asia (but I’m sure there will be some road trips and detours before then, too).

People ask if that's scary but I've been moving, touring, and living out of a backpack for most of my adult life. Letting go doesn’t feel like loss — it feels like relief. The more I let go, the more at ease I feel. Not just with objects, but the emotional weight we carry too. All the just-in-case things we hold onto far longer than we need to — material and otherwise. There’s a life lesson somewhere in there that the more you hold, the harder it is to move forward.

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I often think about the Chinese Farmer parable that philosopher Alan Watts wrote: A farmer’s horse runs away—his neighbors call it bad luck, but he says “maybe.” The horse returns with more horses—good luck? “Maybe.” His son is injured taming one—bad luck? “Maybe.” The injury saves the son from being drafted—good luck? “Maybe.” It offers many lessons about stoicism, detachment, and the power of long-term reflection.

At 45, I'm retiring from one thing and launching another. I'm between countries, between chapters, between versions of myself. Am I at a beginning or an ending? Maybe. Experience has taught me that the distinction rarely matters in the end. Besides, I’ve come to trust the unfolding more than the label.

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If I could give my younger self one lesson, it wouldn't be about avoiding mistakes — the mistakes made me. It would be about timing. Knowing when to let go of something not because you failed, but because you've already gotten what it had to give.

I used to make decisions by jumping first and planning on the way down. These days I plan more than I leap. I have spreadsheets for an international move, a backpacking trip through China, a musical theatre launch. I call it a gift to my future self — building toward things I know I'll treasure, even if I can't fully feel the excitement yet. I don't think that's lost passion. I think it's a different kind of love. Preparation will allow me to be more fully present in each of those future endeavors.

I still want to take big swings. Calculated, yes — but big. I still want to choose discomfort over stagnation, to feel the specific aliveness that comes from doing something genuinely hard and genuinely mine. That part I don't want to rationalize away.

I didn't write this to celebrate myself (I originally didn’t even want to share it at all, until my wife convinced me to). I wrote it because I think we don't pause enough — not to look back with nostalgia, but to actually reckon with where we are, where we've been, and whether that lines up with where we'd like to go.

A tree never stops growing. The day it stops is the day it starts dying. I believe people work the same way — that we're never fully made, always in process. Growth isn’t always obvious while we’re in it. The hardest moments are often the ones shaping us most, even if we only recognize it later. That’s the point, though. The challenges aren’t interruptions to growth; they are where it happens. So maybe instead of bracing against what’s ahead, we learn to welcome it—the stretch, the resistance, the chance to become something more than we were before.

45. Maybe this is the middle. Maybe it’s a beginning.

Either way, I’m still moving.