Play to Win

There is a massive difference between Playing to Win and Playing Not-to-Lose.

I can’t remember when I was first introduced to this concept, but I’ve come back to it over and over again throughout the course of my adult life. 

Whether you’re familiar with this terminology or not, you’re undoubtedly familiar with what this looks and feels like in application. A person or a team comes out of the locker room, starts having a great game, and jumps out to a big lead. At some point, they look at the scoreboard and realize, “damn, we’re way out in front, this is our game to lose.” And then things start to unravel…because they stop playing to win, and start playing not-to-lose.

When we start playing not-to-lose, we get tight, we try to avoid mistakes, and we focus our attention on what can go wrong. Every bad break or minor goof-up becomes evidence that victory is slipping away. This, of course, leads us to be more anxious, less confident and ultimately defeated.

The terrible irony of playing not-to-lose is that it virtually guarantees that you will, in fact, lose. This could be something as small as choking on the 18th hole of a golf match. It could also be spending 25 years in a soul-sucking career. 

I see this commonly in high-achieving individuals (including myself) that seem to regularly bump up against some sort of glass ceiling. They go out into the world, launch into an endeavor, execute like crazy, and before long, they’re having success. At some point, they get a glimpse of the “scoreboard”, realize that things are working, and the whole dynamic starts to shift. You’ve probably heard this referred to as Imposter Syndrome or Self-Sabotage. Some even call it Fear of Success, which is a term I especially dislike because I don’t think that’s what is really happening. 

We’re not afraid of being successful. We’re afraid of losing whatever level of success we’ve already attained. We decide to forego an opportunity to move forward because we’re worried that we might end up going backward. It’s just good ole fashioned loss aversion. When we started our lives as kids with practically nothing, we were totally free to dream big, follow our curiosity, and aspire to something special. But once we’ve built up a nice little stack of chips, be it money or reputation, we now have something to lose. We know that continuing to move forward requires us to keep those chips on the table and put them at risk. We also know that whatever comes next will likely be more difficult than what has come before. The competition will be more fierce, the stage will be bigger, the expectations will get higher…and that is scary. 

While this is all perfectly rational, it is no way to go through life. Sure, we need to accept that striving, competing, and otherwise putting ourselves out there comes with risks. That part is straightforward. What we often fail to account for is the cost of inaction. What are we risking by staying put or holding back? Life is short, and as far as I know, we only get to play once, so it seems like we should probably play to win!

Play to win, but enjoy the fun.
— David Ogilvy

Playing to win doesn’t require us to take wild chances and totally throw caution to the wind. It simply demands that when life requires us to take a gamble, we bet on ourselves. And why wouldn’t we? We got here for a reason (probably several reasons) and there is every likelihood that we’ll continue to succeed. If you look at your life critically, the evidence will almost certainly suggest that you’re far more likely to progress than regress. So rather than waiting for the scales to rebalance or the “other shoe to drop”, let’s reject that entire mindset and ask ourselves a basic question: If I move in this direction, what’s the best that could happen? 

By shifting our focus to the very real opportunities and possibilities ahead of us, we can tap into the positive energy that got us here in the first place. We can build on the momentum that we’ve already created, lean on the confidence that we’ve earned along the way, and pursue the life and work that we truly want. Playing to win gives us permission to imagine something amazing. We can turn our wins into blowouts and championships into dynasties. And perhaps more importantly, we can shake off a bad game (or season) as a necessary part of the process rather than a sign of impending collapse. We can play hungry without playing scared.  

Finally, it is important to note that Playing to Win is not the blind pursuit of “more”. I love the metaphor, but I realize that “winning” is a loaded term and very tricky to define. Maybe we can think of it as the pursuit of better? It is so personal and unique to each of us. I personally keep coming back to the concept of alignment - playing to win means working and living in a way that aligns with my actual values, priorities, and desires. If I’m wrestling with a decision or start to feel myself getting tight, I just ask myself, “What would playing to win look like here?”

We can do this together. I’m convinced that our companies and communities would be much better off if they were full of people that were playing to win. So let’s start placing some bets on ourselves and our teammates. What’s the best that could happen?

PS - If this blog hasn’t convinced you to play to win, maybe this classic rant from the legendary Herman Edwards will.