Lessons from 100 Miles on the Trail

Recently, I completed one of the most physically demanding races of my life, the Grindstone Trail 100 in the Shenandoah Mountains.

Ultrarunning is a challenging hobby—it’s full of highs and lows, requires resilience, and demands perseverance. It’s also a lot like business! I thought some of the similarities may be helpful for others, so below are a handful of the lessons I learned (or remembered) on the trail. ?

You can’t shortcut success

With 100 miles and nearly 22,000 feet of elevation to cover, preparation for this race was paramount. Crossing the finish line reflected not just days of effort, but a year of preparation across training, nutrition, rest, recovery, and even mindset.

And this is much like seeing a project or initiative through to completion. The groundwork you lay in advance makes the difference when it’s time to execute.

A good example in the business world can be found in the rise of AI. Today, you can use any popular AI tool to answer myriad questions, solve complex problems, or simply brainstorm—all in seconds—across almost any subject or prompt. It appears as if this technology is an overnight innovation, but it’s taken decades of work and preparation, both in hardware and software, to get where we are today.

Trust the process—and be ready for setbacks

Early in this race, I was on top of the world. My energy was high, as were my spirits. I’d planned everything from my per mile pace to detailed nutrition to mantras when things got difficult, which I knew they would. I didn’t know, though, that they would get difficult around mile 15—causing me to question my ability to complete another 85 miles.

Having the mental toughness to fight through those early doubts meant shifting focus. Instead of thinking about the full distance, I began focusing on getting to the next aid station, eating, quickly resting on my feet, and then setting off for the next aid station.

In business—especially in tech— we tend to think we have it figured out: The product plan, sprint cycles, roadmap. And while the planning step is crucial, even the best laid plans made by the most informed people can go awry. The key to pushing through setbacks is shifting focus from the big picture to manageable, immediate goals. When unexpected challenges arise, breaking them down into smaller, actionable steps help maintain momentum and navigate through the toughest stretches.

Take the first step first

At its heart, ultrarunning is very simple: Put one foot in front of the other, again and again, for 100 miles. But while it’s simple, it’s not easy. And perhaps that’s why I’m drawn to it. Ultrarunning, much like business and technical leadership, calls on me to learn who I am, why I am, and how I can be better. I go into each event with curiosity and leave with new discoveries about myself and the world around me.

Without curiosity, it’s so easy to get stuck waiting for the perfect conditions—a flawless product, a risk-free launch, or just the right market timing. But perfection is an illusion; there is no such thing.

Both in running and in business, success is about forward momentum—taking action even when the path isn’t entirely clear and trusting that you’ll adapt and learn along the way. The first step might be the perceived hardest, but it sets everything else in motion. To reach any goal, we have to eventually start.

A strong team leads to a strong result

You might be thinking, “isn’t running an individual sport?”

And while the actual running is done by an individual, ultrarunning is definitely a team sport. I wouldn’t have finished without the support of my coach, my fellow competitors, my pacer, and my wife—all who played different roles over the course of the race to help get me to the finish line. To finish this race, I built a strong team, and then trusted them to play their roles so I could play mine.

This is the power of teamwork. When we work to lift each other up, each person bringing their unique value to the table, we can accomplish far more than as individuals. Effective teams can overcome challenges that might seem insurmountable when tackled alone. Just like in ultrarunning, the strength of the team generally determines success or failure in business.

The journey is the destination

In a long race, anything can happen. You go through ups and downs. You laugh, you cry, you get a few (or many) blisters. It’s life in its truest form: a series of unpredictable events that challenge your limits and teach valuable lessons that you can use next time. Without adversity, I don’t know if we’d ever learn anything meaningful. And without achievement, it would be hard to find joy. It takes the gamut to get to the finish line, peppered alongside plenty of monotony as well.

In business, success is rarely found at the end of a straight line. There are obstacles to overcome, moments of doubt, unexpected detours. There are victories and celebrations and growth. And while human nature may be to focus on the highlight reel of wins, it really does take it all to shape our paths.

There’s nothing sweeter than crossing the finish line, but there’s always another race around the bend. The same goes for business. You don’t create and launch a product and then rest on your laurels—you begin working on the next version or new product—or have short-lived success.

Ultimately, the journey is the destination, and that’s the best part.