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Making the Most of Your Wins

So we've been on a rather "downer" tear over the past few newsletters, focusing on miminizing your expectations, and losing well.

This week, we take the opposite tack and look at how to be a better winner. By that, I am not talking about being a gracious and thoughtful winner—though all of that is important as well. I am speaking of how to work with your successes as thoughtfully as you should your losses.

For it is as dangerous to over-identify with your wins as it is with your failures.

Winning, and losing for that matter, are events and outcomes, not labels. You can be winning in a match, race, or other competition, but once the event is over, the win is in the past. Okay, so maybe you can wear the mantle of victory for a period of time until the event is re-contested, but after that? It has the look of the aging athlete or actor, clinging to glory days that are long past. This is not a good look for that person from the outside, but on the inside, they are frozen in time.

This is easy to understand from a loss perspective. Holding onto the idea that you lost, or worse, are a loser, is obviously not a good plan unless your plan is to be a too-small version of yourself going forward. But it is also not good from the winning perspective, either. Yep, you won. Winning at least allows the opportunity to feel damned proud and good about ourselves. But just like the losing label, being labeled a winner is still being called something in the past tense. I’d argue that the effects of clinging too hard to the label of “winner” are just as bad for you and your sense of self-esteem.

When you get defined by an event rather than who you are, it's hard not to get stuck.

I shared the story a few newsletters ago about Dan O’Brien, gold medallist at the 1996 Olympics. His fight to get to the Olympics was, in and of itself, an epic battle, which left him unprepared for what to do when—even though he was favoured to win—he won. You might think that if an outcome like winning was even slightly in your favour, you might prepare for it, but in that there is such a fine line between preparing for a possibility and expecting it (and we all know the downfall of expectations!), Dan can be forgiven for not wanting to jinx the win by imagining what would happen if he did. And even if he had, it would be hard to predict what actually happened…that after the Big Win and celebrations were over, Dan had nothing but a label that defined an already out-of-date version of himself. The pursuit was so dogged, the determination, grit, and image reinvention so consuming, there was no room to contemplate failure, much less success.

Dan spent the better part of the next few months after winning his gold medal watching TV from his couch, without a new label, identity, or goal to strive for. Furthermore, this was a lonely place to be as there were (and are) so few other people in the world with whom to commiserate. There are far more losers than winners in any competition, Olympics included. I don’t know if there’s some super-secret gold-medallist club out there but maybe there should be. Whatever the case, Dan was able to get back on his feet and generously shared his story as a cautionary tale to aspiring Olympians on the pitfalls of success.

Here are some ideas from Dan and others about how to become a more effective and efficient winner.

Learn from your wins. The number one mistake we make after a win is to presume there’s nothing to learn. “We did everything right, what’s to examine,” right? Or, “it’s more fun to celebrate than get stuck back in those uncomfortable performance weeds.” The best in the world do not let an outcome label change their post-event debrief and learnings routine. It may be harder, often, to discern what you did wrong or not enough of after a win, when there’s no better opponent to compare yourself to. Great performers, however, work off what their own best or potential best is—what they are capable of, not what it takes just to beat the people next to them. And then go implement what they have learned.

Enjoy it with perspective. First, any given win does not define you any more than any loss. Even an Olympic win only means that you were the best, okay, in the world, but on one given day. It is the truly rare individual or team that gets to repeat a win, which means coming back and doing it again. Don’t drink the Koolaid that equates winning with “being a winner.” Any more than you should believe that losing makes you a “loser.”

I recall working with USA Rugby, and the team captain at the time said something that stuck with me. "We are neither our worst or our best days." There's something pragmatically true here, and if we can get to this place, often called "the middle way," we suffer less.

But do enjoy it. The other end of the spectrum after a win is the individual or team that is so performance-focused that they forget to enjoy the outcome at all. This is the performer who makes performance a business and along the way forgets why they are doing it. Celebrating a victory is a great way to bring enjoyment back to the process…though, of course, I’d also say that finding ways to enjoy the process AND the product is also important.

I bring a lot of Buddhist psychology into these posts, and find that people sometimes assume that the Buddhist idea of non-attachment to outcome means that you don’t care about either losing or winning and celebration is a no-no. That is not quite true. Caring is great. Caring means that it matters to you. But caring is different from attaching to the outcome. Attaching or clinging is where caring crosses the line to over-identification. “I must have this!” versus “I really want this!” When we are attached, we ARE the outcome, win or lose, never a good place since life always moves on, leaving us, well stuck and suffering. Want it, care about it, yes, and responsibly enjoy the fruits of your victory.

If you are still seeking your own middle way with regard to success and failure, I can help with that.

Don't forget to ping me with any questions related to making performance more frictionless. I'd love to have a crack!!

In case you missed my main message :), I believe that high performance shouldn't hurt people. I provide individual and group coaching on achieving the performance goals you want without hurting yourself or your people in the process. In ways that are healthier, happier, and more sustainable. If you want more information or have questions, you can reach me at

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