How should you define winning?

Alan Gilbert
5 min readAug 15, 2022
This sure looks like winning to me

Last week I finished riding my bicycle across America. From coast to coast. Almost. The fact is I didn’t ride every single mile. I had to take two days off for health reasons. But… did I still complete my goal? This post explores how I changed my definition of winning and recognized that I was too focused on a vanity metric. I discuss why it is important for leaders to pick a definition of winning that is resilient and rooted in meaningful, impactful results and not one that just feeds your ego.

When I conceived of and planned my adventure, I pretty quickly zeroed in on a definition of winning: Map a path from the Pacific Ocean to the Atlantic Ocean and ride every inch of it. Any discontinuity or gap would be unacceptable.

I didn’t ask myself “what would winning look like?” I just set a goal and decided nothing short of that would be acceptable. The problem was, it was a pretty fragile goal. It was the equivalent of a software project where the “constraint triangle” of scope, schedule, and resources were all fixed with no room to adjust any of them. Because our trip was so structured, with a definitive multi-week itinerary and reservations every night, any number of things could cause one or both of us (there were two riders) to have to ride the SAG wagon. All manner of hazards were likely including severe weather, injury, mechanical failure, closed or unridable roads, fatigue, or illness. In fact, every one of these things happened but it was the last one that I was unable to completely overcome.

As detailed in my journal, I contracted an intestinal illness that completely knocked me out for a day, plus another day to eat, rehydrate, and regain my strength. It could have been food poisoning, a virus, heat exhaustion, or a moldy water bottle. My money is on the latter. In any case it was a devastating setback for me. We were less than half-way into our trip and I lost my main goal. My main definition of winning. My raison d’etre. What now? Go home? Mope for the next 2,000 miles?

Once I started to recover, I beat myself up. I questioned if I should have “found a way” to keep riding. But, given the circumstances, that would have put the rest of the trip, and the upcoming crown-jewel ride through Rocky Mountain National Park at risk. I questioned if I should have pushed out the itinerary, rescheduled the remaining venues, and not missed any riding. But that would have been terribly unkind to my riding partner and our SAG drivers (our wives, who we called our “support angels”). In the end I decided to just “take the hit” and ride the SAG wagon, rejoining the ride after two days off, with the itinerary in tact. It was unquestionably the right decision, painful as it was.

At first I was so thrilled to be back, I didn’t care about the gap. But then I started to obsess over it. When I publish our progress map, do I continue to show the gap? When we crossed the Wyoming/Colorado border I said to my riding partner, “we freaking road our bikes here from the Pacific Ocean!… well you did.” When I told people on the road about what we were doing, I kept feeling like I should qualify it and mention that I missed two days. I worried about the “asterisk” that would be attached to the trip, like there was some imaginary trophy that would be handed out but not to me.

Our coast to coast route, with the section I missed in green

But as we accumulated more and more miles I began to put things in perspective. I realized that it was time for me to redefine what it meant to win. I started to look at my setback like a pick-six in football — a painful blow but not the end of the game. After all, I still rode from one ocean to the other, through 10 states. I still rode over 3,000 miles and averaged nearly 100 miles a day for six weeks. I still overcame adversity every day. I still saw new, interesting, beautiful places and got out of my echo chamber, connecting with other Americans as just people. I was still riding my bike every day on the trip of a lifetime. I still exceeded my fundraising goals for cancer research. I realized that my “ride every inch” goal was really a vanity metric — something that made me feel good but not really that important or necessary. And I changed my definition of winning.

I learned a valuable lesson that I will carry forward both for myself and in my leadership roles. When leading teams, it’s tempting to set a goal that feels good or sounds ambitious, without considering if it is the right one or if it is resilient. And then that becomes a proxy for winning and managers or the teams themselves judge success or failure only according to that definition. All the while the team may never focus on what really matters. And worse yet, the team’s efforts may be considered a failure because the definition of winning was too fragile and predictable setbacks occurred.

Pick a definition of winning that is resilient and rooted in meaningful, impactful results and not one that just feeds your ego.

The classic mistake I have frequently been party to is to set a deadline for a project to be completed, often before it is fully defined, instead of focusing on the desired business result. Deadlines are important but typically not the be-all-end-all (unless they are externally-driven, like a trade show). Others I have seen are growth rate, hiring volume, diversity hires (without also considering inclusion, equity, and belonging), page views, and social media followers. This article has a good discussion on vanity metrics.

Avoid the mistake of defining winning based on a project deadline and instead focus on the desired business result.

Any difficult challenge requires a clear definition of winning to provide direction and clarity in the face of inevitable adversity. This is true for individuals and doubly so for teams. The lesson I learned is, when taking on a difficult challenge and setting a goal, to be thoughtful and deliberate in defining winning. Define it by considering results that are meaningful and have broad and lasting impact. Define it in a way that is resilient and can withstand setbacks. Resist the temptation to choose something because it sounds bold, makes a great headline, or feeds your ego. There’s nothing wrong with a great headline to motivate and celebrate, but it should not be the centerpiece of your goal. It should not define winning.