Cape Town Paraglide

“I’m a Man. I’m Forty!”

I turned 40 today.

Everyone I’ve told that feigns surprise. They blurt, “you don’t look 40,” but I know their shock is that I could be so immature at this age. I’m supposed to have found a filter by now—or at least a modicum of wisdom from a decade of answering the irrational questions of a litter of kids.

Know that I’m trying to grow into my age. I’ve gotten counseling, read scores of nonfiction & self-help books, gone to educational conferences, and traveled the world. According to my wife, I’m a better me at every birthday. She might be right, but I’m still behind. In case you’re likewise playing catch-up, here are the big lessons I learned during each of my first four decades.

Years 1-10 (1978-1987)

That BMX Life

You don’t need a screen to have fun.

By the end of my first decade, I had received birthday cards in four states and attended school in three. Without access to youth sports beyond freeze tag, I found identity in academic competition. One year, I completed two and a half years’ worth of curriculum for the stickers on my progress chart. I took down all comers—especially Jeremy—at math flash card ‘round-the-world. I got my classwork done early, so I could watch Beanie & Cecil movies in my school’s unused classroom on Friday afternoons.

TV left our home right after my fourth birthday and didn’t return until the Christmas after my ninth. My grandma thought we needed exposure to the outside world (beyond the New York City fireworks we had watched on a borrowed black and white TV). I’m now glad we didn’t have a TV until then. I was too busy sledding, doing tricks on my BMX, and memorizing Monopoly rents. I loved the smell of my electric train & slot car tracks and the rush of the zip line in the Gorselines’ backyard. I took a punch from a guy who liked my second-grade girlfriend and got stabbed in the hand—maybe even by the same kid.

I was intrigued by the college students my parents had over to the house and seeing my mom type other people’s college papers for money. I loved riding shotgun, while Dad spun donuts in our Mercury Capri around empty Tennessee intersections—because “New Yorkers know how to drive in snow.” He let me get a five-speed Nissan 510 up to 55mph on a dirt road off John Brown Road. That’s when I fell in love with manual transmissions.

So, I’m okay with having missed every episode of Airwolf.

Years 11-20 (1988-1997)

Fresh Meat for Freshman

You can’t impress people into liking you.

Dad bought a riding lawn mower on the condition that I’d mow other yards with or for him at $35 per yard. I got a W-2 as soon as it was legal and worked two jobs at a time starting my junior year of high school. I tried too hard to get a girlfriend: writing letters, penning poetry, and even coloring a complete The Little Mermaid coloring book. As a home-schooled grounds worker at a beautiful golf course, I endured nicknames like fuck up, Forrest George, and faggot. That last one stuck after admitting that I hadn’t had sex—even after they got a girl passed-out drunk and left her for me in the cart barn.

Money MattersI found my identity in my hustle. In junior high, I escaped bullying by competing for valedictorian. In high school, I saved as much as 85% of my take-home pay for college. Once I got to college with a clean slate and no nicknames I couldn’t repeat in church, I double-minored and wrote for the yearbook. Punching above my weight class, I dated a junior my freshman year and tried out for intramural sports. I served my first of six consecutive semesters in leadership for Omega Kappa Delta.

People don’t ask for résumés, though, when determining whether or not to befriend you. Neither do girls.

Years 21-30 (1998-2007)

Indiana Awards Haul

You can’t impress God.

Those last two years of college changed the trajectory of my life. I found a wife, a career, and a voice for my writing. After graduation, I paid off my student loans in seven months and started writing a book the following summer. A year later, I started a moonlight gig that turned into an S-Corp and enough disposable income to buy a house, occasionally leave the country, and own a car from The Italian Job. I found identity in my ambition and won scores of awards. People started paying me to give seminars around the country.

My blog started near the end of that decade, as I journaled through a class at a church very different from the eight I attended before I got married. That re-started my spiritual journey in a new direction, as I wrestled to extricate insecurities from my soul. I saw more life change in and around me in those first two years than in my previous two decades in organized religion, and I fell in love with wearing a neon yellow baseball cap to church every Sunday.

Take it from me: culture offers lots of ways to cover our brokenness, but you have to get naked for surgery. Plus, wholeness means you don’t need such an expensive wardrobe.

Years 31-40 (2008-2017)

Dawn Prayer Circle

Authenticity sells.

This past decade took my blog, my business, and my ministry to new heights—and new lows. I found an identity of leadership and influence, while accumulating wonderful friendships. I traveled to remote and foreign places that made my soul come alive. I experienced incredible adventures—the stuff of dreams. At the same time, I paid dearly for several pursuits driven by my insecurities. My ego literally cost me tens of thousands of dollars during God’s pruning process.

Me and My BoysI don’t know if I “found myself” yet, but I discovered where I’m comfortable. Counterintuitively, I felt freedom and acceptance in disclosing my dysfunctions. My most popular blog posts were not my commercial ones but the ones where I revealed my flaws and pulled back the curtain on improper motives. I learned that I’m a story teller more than I am a writer and that people want stories that make their perceived inadequacies feel normal.

If you’ve read this far, you’re one of those people. I’m going to keep writing for you, because I’m going to keep fishing for stories in the pond of my soul. If all goes to plan, maybe we’ll both learn something along the way.


  • Phil Bowman

    Thanks for being transparent, Ryan. I am reading this in a morning worship service in a church I love, but is shunning me because of perceptions rooted in speculation, assumptions and gossip. Your blog posts entertain, challenge and humble me.

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