How Winners Measure Success

Moving + learning + reflection will get you across your own finish line.

I was tired, defeated, and upset. My legs had nothing left. I watched as the ultra-marathoners passed me by on their way to the finish line. I cringed to see them swiftly and steadily outrun me, even though their course was 35 miles — three times the length of my own race’s distance.

I’m an executive coach and, intellectually, I know that success is not measured by productive outcomes, but rather the material impact productivity has on the individual’s experience. In this sense, productivity is not the goal but serves as a platform for each of us to grow and learn as individuals and to measure against our internal experience.

But in that moment on the race course, all I could think about was the finish line, and how embarrassing it would be to cross it in front of my family, who’d been waiting patiently for hours.

As I gave in to my exhaustion, I flashed back to the memory of completing a marathon on a major milestone birthday. My body was different then, and my life had changed. Now out of shape, all I could hear were the critical voices in my head saying loser.

Winners and Losers

I wasn’t going to win that race, but I also wasn’t a loser. Both messages, however, are typical for the way we talk — to ourselves, to our teams, and about our businesses.

We are obsessed with outcomes in our culture. Specifically, we’re obsessed with winning and success. We elevate athletes, entrepreneurs, and entertainers as the ultimate winners in our society, and look to them to be our guides for how to be winners in life. Yet these are the same people who are often struggling backstage, off-court, and behind the scenes. We judge them on what we see without ever really knowing what their true triumphs and failures are.

I recently read an article that talked about how Michael Jordan, Oprah Winfrey, and other “A-listers” don’t choose happiness as a winning mindset. Instead, they take actions that are meaningful to winning, no matter whether it leads to their own personal satisfaction. Michael Jordan shot free throws for hours a day because the practice continually refined his skill and built his strength, not because it filled him with joy. Real winning, the article shared, requires that you make sacrifices, work hard, and put in your time toward your goals.

It makes sense: Putting in intentional effort will lead to positive outcomes. It may even lead to winning.

But that doesn’t account for the critical voices in our minds, and it certainly doesn’t cover a full definition of success.

Michael Jordan is one of the greatest athletes of all time, but do his accomplishments in his professional field translate across the board? Is he a winner in his marriage? As a parent? As a friend? As a citizen? At satisfaction with life? Is he a winner in his own mind?

Once we start asking these honest and difficult questions, and once we push past points per game and free-throw percentages and other successes earned on the basketball court, the way we define and measure winning and losing becomes far more obscure and challenging.

Most of us won’t ever be inducted into a hall of fame, be the first to cross the finish line at a marathon, or be considered an A-lister, even though we try over and over again to measure up to those kinds of wins, even though the voices in our own heads tell us we should seek success in the same ways.

When we consider what it means for each of us individually to succeed, the whole winning-losing framework that many westerners know and abide by falls apart. What if you asked yourself what you value most in life, and what winning at those things might mean?

  • How would you know you are succeeding as a parent?
  • What might it mean to be an A-list citizen of your community or participant in your romantic relationship?
  • What do you count as a win for your mental, emotional, and physical health?
  • How might you measure your own internal satisfaction with your life balance?
  • How many hours are you willing to put in practicing your skills and building your strength in painting, volunteering, acts of compassion, or learning a new language?

These questions require some outside-the-framework thinking. We have to stop measuring success by the old standards of productivity– how many points scored, dollars spent, sales converted, shiny things accumulated — and shift the message (both internally and externally) that real wins are determined by the individual.

As an experiment, what if you let go of the old notions of winning ingrained in your brain? What if you considered a new definition of success in your work, your relationships, and your life, and how you might put in the early-morning or late-night practice to cross that finish line?

It might mean that you ease up on doubling your commissions next quarter or parking another Tesla in the garage. It could be that you get totally uncomfortable by thinking up more ways to be exactly the kind of team member, partner, parent, friend, or neighbor you want to be than studying spreadsheets or hard-charging into new client meetings. If you’re willing to give it a try, here’s how to get started.

A Formula for Authentic Success

Consider this strategy: moving + learning + reflection will get you across your own finish line.

To reframe your own definition of winning, first, you’ve got to MOVE. That means you will get out of your comfort zone, question the tenets you’ve held as truths, and open up to what it might mean to think bigger, go deeper, and stay on your own path at this new pace. It means that you will make choices and start moving toward those choices. It is taking action, moving beyond where you are now in any direction. Movement creates a new context from which to observe yourself. To look at who you were before and who you are now.

Second, you must commit to LEARN. No matter how many years you’ve been in the business, how many hours of training you’ve completed, or how many times you’ve out-earned or outsold or out-run everyone else in the organization, you’ve got to keep returning to a healthy growth mindset. Ask yourself what else you could explore, who else you could connect with that has something to teach you, what other skills would help you redefine winning. Seek opportunities to be more of a student than teacher, a keen observer as well as master, returning runner rather than ultra-marathoner. The goal here is not about where you are in relation to others but rather, where you are in relation to yourself.

Lastly, REFLECT. Gather up all the information you can as you explore what it is like to live in this new framework. What did you learn from the losses? What unexpected wins did you experience? Where did you feel triumphant? Uncomfortable? In your ease? With all of that data, ask what you might do differently next time, what you can take away, what it feels like to be in this experiment. Reflect so that you’re inspired to make new choices and start this process all over again.

What choices do you have now? What could your life look like by building new ways of winning? How might your whole self show up in the world? What impact might you make on others? On yourself?

The End of One Race and the Beginning of Many More

By the time I reached mile 12, I had been on the trail for nearly as long as it took me to run a full marathon three years earlier. Barely able to lift my legs, I had no choice but to walk.

One of the ultra-marathoners who was on mile 34 and about to finish, pulled up alongside me. He could have broken away toward the finish line. Instead, he stayed right by my side.

I was barely able to breathe, let alone talk. I didn’t want to. With one slow glance at this elite athlete next to me, I shifted back into running. He didn’t go anywhere. He ran alongside me without saying a word and we made our way together.

As the finish line rose up over the horizon, I could see my wife and little daughter waiting for me. The ultra-runner saw my family cheering me on, too, and selflessly peeled off to give me the glory of a triumphant finish in front of my loved ones.

He could have gotten a better time, but it wasn’t about that for him. He knew that finishing was about what we learn about ourselves, about who we grow into because of the experience of finishing, and about discovering our perseverance and heart. The ultra-marathoner stopped and supported me for these right reasons.

He held me with esteem and it gave me the strength to finish strong.

Crossing that line wasn’t about my time anymore, or how I compared to all the other runners. It wasn’t about measuring up to my marathon past. It wasn’t about what I’d known as success or failure. It wasn’t about what my internal and external messages about winning and losing once were.

It was about who I was in that one moment, how I’d moved, what I’d learned, and how I’d shifted, even over the course of 13.1 miles. It was about who I was becoming, and what a bigger, more glorious win that was as I finished, and that it continues to be.

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