From the box of unanswered (unanswerable?) questions:

Is it enough to try?

I’ve been taught that yes, yes, absolutely YES it is enough to try. Failing is fine. Just do your best, that’s all anyone can ask of you. I’ve heard this philosophy, I’ve preached this philosophy, I’ve lived it. As a parent, it is baked into my core. As a people manager, it is indispensable to motivating my team. We can control our effort, we can’t control results. All you need to do is try. Trying is enough.

I am Team Try through-and-through.

But lately, I’ve been tempted by Team Win.

The apex of this temptation happened at the 2018 Winter Olympics, seeing Jessie Diggins win the United States’s first gold medal in cross-country skiing. The video of the final stretch of her race is quite incredible to watch.

I couldn’t help but watch and wonder:

  • How would she have felt if she had come up inches short?
  • What if, instead of the first U.S. gold medal, she had claimed five silvers?
  • How did the second-place finisher feel?
  • How do Olympic athletes who spend 4+ years working and training, expecting to win, how do they feel when they don’t win?

Would “trying” still have felt as gratifying?

During the Winter Olympics, I happened to be reading a book called You & a Bike & a Road, a graphic novel about the author (Eleanor Davis) attempting to bike from Arizona to Georgia over the course of several weeks.

She did a monumental thing by simply setting out on the journey. She told about the emotional and physical toll of pedaling miles and miles by yourself. She got more than halfway through and started feeling worse and worse, her body betraying her. There were multiple moments when she nearly gave up, only to get the extra boost of health or encouragement she needed to get back on the road. But then finally when she was just a few hundred miles outside Athens, she gave in. She called her husband. He picked her up, and they drove the rest of the way home.

I was …

so disappointed.

She was this close to finishing! Can you even imagine how incredible it would have felt to do the thing you set out to do? To complete your goal? To win the thing?

What is it about that intersection of trying and winning that compels some people forward and gives others the freedom to stop.

And why did I suddenly feel so judgmental about it all?

Speaking as a Team Try advocate, I applaud the author’s efforts to bike such an extreme distance. I see so much that she should be proud of.

But having caught a glimpse of Team Win, I wonder if I have been wrong all along.

Maybe the only thing that matters is winning, and the rest of us are just kidding ourselves? After all, the “rest of us” is the majority of us. So few people can win it all. Perhaps we’ve made effort our defense mechanism against disappointment.

Still, there is oodles of evidence that trying is worth celebrating. I could find quotes for days about the virtues of effort against win-at-all-costs. Just the other day, I picked out this gem from Steven Pressfield, in Tim Ferriss’s book Tribe of Mentors:

Don’t worry about your friends “beating” you or “getting somewhere” ahead of you. Get out into the real dirt world and start failing. Why do I say that? Because the goal is to connect with your own self, your own soul. Adversity. Everybody spends their life trying to avoid it. Me too. But the best things that ever happened to me came during the times when the s*** hit the fan and I had nothing and nobody to help me. Who are you really? What do you really want?

Another example is from my friend Rodolphe Dutel who shared this post on LinkedIn about the dangers of comparison:

He got promoted before you did?  She exercises at 5 a.m. every day? Their dog went viral on Instagram? …good for them!  We all project the most desirable aspects of our lives, Yet we all face struggles & dilemmas.  A wise friend once told me:  “There are plenty of jobs that look good but feel bad”. True for jobs, true for parts of our lives. We’re more than what we project.

If I view life as a “zero-sum game,” then one side’s winnings are directly proportional to another side’s losses. If I cut a bigger slice of a cake, that means less cake for others.

But maybe we live in a “non-zero-sum game” world. The author of You & a Bike & a Road may not have seen the completion of her journey as the only way to “win” her goal. The high of getting there did not need to equal the anguish of not. Along the way, there were many, many moments of celebration and winning.

Likewise, for Olympic athletes, the disappointment of not finishing first may be crushing, yes, but it’s also just one dot in the overall experience of their Olympic games. The other dots may have been huge highs: personal records, in-game moments of bliss, the sheer fact that you got to the Olympics!

To go even further, it’s possible that Team Try and Team Win don’t exist at all, and I’m simply confusing the black-and-white choice of one or the other with my bias for recency. In particular, I may be experiencing the Peak-End Rule, which states that people largely judge an event by how they felt at its peak and at its end.

via Aly Jula

My “end” experience with the book You & a Bike & a Road was finding out that the author didn’t make it to her goal.

My “end” experience with Jessie Diggins was a thrilling gold medal triumph.

Therefore, my overall experience with each event was that one was disappointing and one was inspiring, when really — in aggregate — they were much closer to one another in terms of success, inspiration, and awesomeness.

What does this all mean for my wishy-washy wondering about Trying vs. Winning?

I think my experience taught me this: Trying and failing is always okay. And it feels okay when you either a) consider the failure in perspective with all the other wins along the way or b) get back out there and try, try again in order to make a new “end” experience for yourself.

Which reminds me of another mantra: “Just keep trying. You’ll get better.”

Daniel Tiger hug

Posted by:Kevan Lee

VP of marketing currently living in Boise, Idaho. I work with the lovely folks at Buffer. You can join my email list to get an inside look at marketing and branding and team-building in tech.