On a crisp spring morning in Washington, DC, the city felt almost cinematic. The kind of day where the sky looks painted, the air carries a refreshing chill , and the light hits the monuments like they are the stars of the show. It was race day at the Annual Cherry Blossom Run—a ten-mile tour through one of the most iconic cities in the world.
I’d been training with a buddy, but a few months before race day, he suffered a foot injury. Training slowed and then stooped altogether. By the week of the race, his goal wasn’t performance. It wasn’t even finishing. It was simply: show up and see what happens.
For the first mile, everything felt normal—easy pace, light conversation, the familiar rhythm of footfalls hitting pavement. But then I noticed it: a subtle change in his stride. He looked over, gave a quick wave, and said what I knew was coming: “Go ahead.”
I pushed forward, settling into my own pace. When I crossed the finish line, I made my way to our predetermined meeting spot: the Red Cross medical tent. (It seemed like a prudent choice just in case!).
I expected to wait a long time. So I settled into a comfortable spot and took in the energy of the crowd. Then, out of nowhere, and WAY sooner than I expected, my friend showed up. Do you believe in miracles? I asked him how he was able to finish. He shrugged, almost dismissively.
“They didn’t make it convenient to quit.”
It was a profound answer and I asked him to elaborate. Every mile or so, there was something pulling him forward. A drumline echoing down the street. Volunteers handing out water and Gatorade. Strangers with handmade signs offering high-fives. Each moment broke the race into smaller, more manageable pieces with rewards along the way. And then, late in the race, came the ultimate reward: a station serving Oreos and beer. God Bless America!
Those little milestones and checkpoints introduced friction from quitting. And that is so important as we pursue our lofty goals in our business and personal lives.
Recognition Matters
In organizations, leaders often set ambitious, long-range goals and assume motivation will take care of itself. But in reality, people need to feel progress in real time. When a team can point to tangible movement—whether it’s a prototype completed, a client milestone reached, or even a well-run meeting—it transforms an abstract objective into something real and attainable.
Just as importantly, consistent recognition acts as fuel. A quick note of appreciation after a tough week or a moment to acknowledge effort in a team setting can reignite energy in ways that formal incentives often can’t. Over time, these small reinforcements create a rhythm where people don’t just push through work—they begin to build momentum within it. And, dare I say, enjoy it! In those environments, stopping doesn’t feel like relief—it feels like interruption.
Lighten Up, Francis!
The same dynamics show up in our personal lives, just in subtler ways. Big goals—whether they involve health, relationships, or personal growth—can feel distant and intimidating when viewed all at once. But when those goals are broken into smaller, meaningful checkpoints, they start to feel achievable.
We are far more likely to succeed by committing to writing a few paragraphs each morning than by aiming vaguely to “write more.” And we are far more likely to achieve financial stability by focusing less on retirement and more on steady, tangible wins—paying off a credit card, building an emergency fund, or reaching the next savings milestone.
And we might as well enjoy it! A long journey without any moments of lightness can become draining, even if the end goal is worthwhile. Intentionally weaving in things that make the process enjoyable—a favorite playlist during workouts, a standing coffee ritual after a productive week, or even the absurdity of washing back a sleeve of Oreos with a cold DC Brau—increases our chance of success!
Design for Resilience
We tend to think resilience is purely internal. Grit. Discipline. Mental toughness. Those matter. But environment matters too.
My friend didn’t finish because he ignored the challenge. He respected it. But he allowed space for enjoyment—for surprise—for those glorious Oreo and beer moments!
We need to design our path where quitting feels like more effort than finishing. Our goals are serious, but we don’t have to grimly march toward the finish line. We can be committed and still have fun. We can pursue excellence and still appreciate the moment. We can chase a goal and still laugh at the unexpected perks along the way.
If we set up our lives for success—with just enough Oreos and beer along the way—we simply can’t lose.