⛰️ Trail & Error: My Race Didn’t Go as Planned

Welcome back to ⛰️Trail & Error, where we explore the journey of designing work and life on your own terms.

In this issue, we’re talking about lessons from my trail race this weekend — how setbacks can shape us, the importance of finding meaningful work, and why resilience matters both on the course and in your career.

If you’ve ever felt stuck doing work that doesn’t align with who you are—or if you’re wondering how to navigate challenges while staying true to yourself—then read on. ⛰️

Antifragility in Action: Lessons from Mile 6

There’s something transformative about running through Muir Woods and Mt. Tam. The redwoods stretch endlessly toward the sky, the climbs push your body and mind, and when you crest the ridge, the Pacific stretches out like an infinite promise. Trails like these remind me why I lace up in the first place—there’s nothing quite like the push and pull of effort and awe.

This year’s trail half-marathon started out great. I felt ready—confident in the training I’d put in and excited for the challenge ahead. Last year, this same course left me nervous and cautious, my first-ever trail race feeling more like survival than adventure. But this year, I felt different. I started faster, moved more freely, and trusted that I belonged here.

Then came mile 6. A misplaced step, a sharp twist, and pain that turned every stride into a test. Eight miles still lay ahead, with all the toughest climbs and descents yet to come. It would have been easy to let frustration take over—to fixate on what this injury might take away. But races, like life, have a way of demanding your focus.

From that point on, every step hurt. Each climb became a quiet conversation with myself: Can I keep going? What adjustments do I need to make? How do I navigate this without making things worse? The race stopped being about beating last year’s time or even enjoying the scenery—it became about finishing, one intentional step at a time.

I wasn’t alone, though. My friend Trevor ran with me, offering steady encouragement and the kind of quiet support that reminds you you’re not in it alone. His presence didn’t take the pain away, but it did make the challenge feel less isolating.

And that made all the difference—not just having someone there, but having someone who believed I could handle the trail ahead.

The funny thing is, when I crossed the finish line, I wasn’t even thinking about my time. That wasn’t the win this year. But later, when I checked the results, I saw I’d beaten last year’s time by a full minute. That wasn’t the goal, but it wasn’t an accident either.

I’d spent months building a foundation—training through the early mornings, pushing through tough climbs, and learning to trust my body. That work didn’t just make me faster on the easy days; it gave me the strength to adapt when things got hard. This was how my ankle looked a few hours later. 😬

It’s a lesson the trail teaches over and over: setbacks aren’t the end of the road. They’re opportunities to adapt, to grow, and sometimes, to discover just how resilient you really are. Antifragility—the ability to thrive not despite challenges but because of them—doesn’t happen by chance. It’s built step by step, through every stumble, climb, and recalibration. ⛰️

Running on a sprained ankle wasn’t ideal, but it made the race more meaningful. Last year, I crossed the finish line questioning whether I belonged. This year, I finished with pain in my ankle but certainty in my heart. And that certainty? It comes from the willingness to embrace the hard things—not just to endure them, but to let them shape you into someone stronger.

Now, I’m thinking about next year. A 30K feels tempting—not because I have something to prove, but because these trails keep calling me back, daring me to grow. ⛰️

Do You Love What You Do?

It’s very hard to be successful at something you hate.

Over the long term, unless you’re doing it purely to survive, your motivation will eventually run dry. And even then, it’s a brutal path to walk, especially when the world around you keeps whispering—or shouting—that you should feel fulfilled in work and life.

But what if you don’t? What if work feels like a grind? Or, what if it’s fine—but it’s not what you know you’re capable of?

David Whyte, in Crossing the Unknown Sea, writes:
“To have a firm persuasion in our work – to feel that what we do is right for ourselves and good for the world at exactly the same time – is one of the great triumphs of human existence. We do feel, when we have work that is challenging and enlarging, and that seems to be doing something for others as if, in Blake’s words, we could move mountains, as if we could call the world home; and for a while, in our imaginations, no matter the small size of our apartment, we dwell in a spacious house with endless horizons.”

That feeling—challenged, growing, aligned, and useful—is rare. But it’s possible. I’ve felt it in my own work, and I know how transformational it is when others feel it too.

I also know how it feels to lose that connection to work, to question whether it’s possible to find fulfillment and success at the same time. But here’s the truth: you can find a way to align what you do with what you value. You can build a career or business that challenges you, supports you, and feels like home.

Do You Know Anyone Like This?

After nearly 20 years in tech, I realized true success isn’t just about pushing through—it’s about finding purpose, freedom, and fulfillment. Now, I’m helping others build careers that align with their values without sacrificing income or family time.

I’ve opened up some space on my calendar for complimentary coaching and am looking to work with someone specific who:

• Has been in their industry for 10+ years and is ready for a major change.

• Feels capped by a single income source or traditional career path.

• Is driven to create a career that brings both financial growth and personal fulfillment.

If that’s you—or if someone comes to mind—just reply to this email. I’d love to connect.

Sometimes, the first step toward moving mountains is simply raising your hand.

Thanks for reading Trail & Error. If you enjoyed it, please share it. Together, we’ll help people build more resilient & fulfilling lives!