Winning at Last Place
[The author, before the ride that changed everything.]
In a country obsessed with winning and success, coming in last can feel like failure.
But sometimes, taking last place is the first step toward something much bigger.
I learned that lesson many years ago.
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The Ride That Changed Everything
I entered college fairly sedentary — carrying the infamous “freshman fifteen” (or maybe twenty-five). Then, as a junior at the University of Texas, a friend invited me on a bike ride along Lake Austin.
That ride changed my life.
I fell in love with the wind against my skin, the rhythm of my body matching the curve of the road, the alternating effort and release of uphill climbs and downhill coasts.
Before long, I was riding a few days a week through the gentle terrain of north Austin. When I heard about an organized 50-mile fundraiser, I signed up immediately. It sounded fun — a beautiful ride shared with others.
The event started at 7 a.m. on a hill in west Austin. While chatting with a friendly group doing the 25-mile loop, I missed the start of my group’s 50-mile ride. They invited me to join them, but I was determined. I waved goodbye and set off — already far behind.
The hills were much steeper than anything I’d trained for. I was riding my old Schwinn 12-speed from high school — sturdy but heavy — while others glided ahead on sleek aluminum and carbon frames.
Each hill felt like a question: How much strength do I really have? How willing am I to find out?
As the miles stretched on, I lagged further and further behind. The “sag wagons” started circling, asking if I wanted a lift to the finish. I shook my head.
I was determined to finish under my own power.
By the time I reached the halfway point, I was utterly exhausted. When a kind rider from the 100-mile group slowed to tell me my back tire was nearly flat, I realized I’d been climbing those endless hills with half the air I needed.
After inflating the tire at a gas station, I pressed on — whispering childhood mantras from The Little Engine That Could to keep myself moving.
Finally, after hours of grinding effort, I reached the last mile — only to find the steepest hill of all. My lungs burned, my thighs trembled, and the finish-line cheers echoed faintly above me like a promise.
I summoned my final reserves of strength, passed two other stragglers, and collapsed at the finish line — nearly last. My sister carried my bike because I could barely stand. I slept for hours before I could even eat.
And yet — I was hooked.
I had learned what my body was capable of, and I wanted more. Soon, with training and better equipment, 50- and 80-mile rides became effortless.
[Years later — stronger legs, lighter bike, same determination.]
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Lessons from the Back of the Pack
That day taught me that the riders who come in last are often working the hardest.
When my kids later ran cross-country, I always stayed until the last runner crossed the line. Because I knew: those kids weren’t losing — they were beginning. They were showing up before they were ready, taking brave steps that would one day carry them further than they imagined.
Those lessons served me again years later when I launched my consulting firm. “Winning” a contract meant putting food on the table for my team and my family. We celebrated when we came in second — because our small five-person company was holding its own against national firms with decades of experience. We were climbing steep hills, and we were still in the race.
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What I Still Carry Forward
Now, I see that same pattern in every new venture and season of life.
Each stage brings its own version of that first long ride:
Starting late → Do it anyway. Begin, even if you’re already behind.
Steeper hills → Push forward and learn from those ahead.
Flat tire → Pause, find the friction, fix what’s slowing you down.
Final stretch → Give it everything when everything is needed.
Recovery → Rest. Let your body and spirit absorb what they’ve learned.
Preparation → Train for the next challenge with new awareness and strength.
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There’s courage in being last.
It means you showed up. You tried something you weren’t fully ready for. You trusted that what mattered most wasn’t where you placed — but what you learned along the way.
Sometimes, the greatest victories begin at the back of the pack.