Playing to Win or Playing Not to Lose?

The question has been following me around for two weeks. Are you playing to win, or not to lose?

From World Cup commentators to Brené Brown, and now to Ben Crowe, a mindset coach for elite athletes who asks a version of it: are you in a play state or a fear state? Same thing underneath. Fear is what flips you out of playing to win and into playing not to lose.

When I look for play in my own work, I use the word “fun.” That’s my signal. So when I think about playing to win, I’m really asking whether the work is fun.

I obviously think about this question for my clients, but it's been just as important to me and to what I’m trying to accomplish. I walked back through my own career, role by role, asking a single question. When was I playing to win, and when was I playing not to lose?

I can feel the difference before I can explain it. When I’m playing to win, the work is fun. I’m in flow, working on something I actually want rather than something I’m supposed to want. That doesn’t mean easy. Some of the work I’m proudest of was hard and stressful and kept me up at night. Hard isn’t the differentiator.

I was in a second-half planning session this week where we talked about the things we put off but know we need to do, the business growth hygiene tasks. When you’re playing to win, these are the ones you do whether you want to or not. You can make them more enjoyable with better background music or by being a little less serious about the tasks, but that’s not the kind of fun I mean. The fun that tells me I’m playing to win is whether the work itself is something I actually want to be doing.

There are seasons in a business when playing not to lose is the right call. You protect what you’ve built, and you stop any bleeding. What’s easy to miss is the cost of the careful choice. It quietly trades the thing you want for the thing that feels safe.

I’m in a season of writing the next chapter of work after a wonderful stretch in a fractional leadership role. Some days, I catch myself considering an option that protects against an empty calendar rather than patiently building the thing I actually want. That’s playing not to lose. I can feel it, because those options don’t pull at me the way the right work does.

I won’t get this right every day, but heading into the second half of the year, the question I’ll keep answering is, how am I playing to win?

I’ve shared that I pick three anchor words for each year to keep my focus grounded. As I wrote about early in the year, mine are Clear, Trust, and Spacious (you can read the original article here). Coming out of the planning session, I’m adding one more for the second half: Undaunted. Merriam-Webster defines it as “courageously resolute especially in the face of danger or difficulty: not discouraged.” So I’ll be undaunted as I play to win, because the mission I’m on to support leaders won’t only benefit them, but the teams they lead today and tomorrow.

Hi. I'm Melissa. I work with you on the decisions you can't talk through with anyone inside your organization, because everyone who could help you think it through has a stake in what you decide. I don't. We work through what's driving the decision, how you're making it, and what you might be too close to see. I pressure-test your thinking so you leave confident in your plan.

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