What prize do you want to win?

And if it's not a 5-foot teddy bear stuffed with work, then stop playing

Photo credit: My friend, David Dini

Hi! My name is Bree, and I write about how to make work more joyful and less everything. Subscribe for weekly essays on everything from rewiring organizations to cozy teams to living a Portfolio Life.

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Sometimes I think about Finland’s former 35-year old prime minister.

Most days I feel like I’m killing it because I’m doing good work at work, I’m taking great care of my health, I’m supporting my dad and my daughter, writing this post! But some days I feel like I could be doing so much more. For example, I have not been the leader of a nation for five years now.

If I google “get into politics” tomorrow, how long until I can feasibly run for President?

I know, I’m being dramatic. I should at least run for Senate first.

I can recognize that I’m spiraling when these thoughts rush in. Being President is an extreme example, but it only takes a good social media scrolling session for my ambition monster to rear its green head. In these moments, I’m awash in both questioning and mourning the classically ambitious parts of myself that have ebbed in recent years:

●      Is it bad that I’m not pushing my way up as hard as I can?

●      Is it bad that I’m not exhausting* myself?

●      Am I a bad feminist for not doing so?

*If I haven’t “exhausted” myself, by definition, I had more to give to my career but chose not to.

In these moments, I ask myself: “If I went after this success I’m envying… What would that get me?” Or, WWTGM if you want to put it on a bracelet. I try to remember that my job, as the boss of my life, is not to follow ambition for its own sake—it’s to ensure that if I’m working really hard at something, that I actually want the prize at the end.

Like spending $50 to conquer balloon darts at the carnival and winning! Only to be rewarded with carrying around a 5-foot teddy bear the rest of the day.

Do I want to be President? I didn’t even like running for VP of student council in 5th grade. So no, I do not want that prize.

I do not want that prize.

I do not want that prize.

I do not want that prize.

It takes a few times before my brain considers believing it…

If you’re working hard at something—scaling a business, interviewing for a new role, trying to land a new project, gunning for a promotion—I invite you to ask yourself: “If I succeed, what would that get me? And do I want that prize?”

Only you know the answer! I hope it’s a ravishing YES. And if it’s not, well that’s the first step in moving along to the next carnival game.