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When Losing is Winning

Simone Sinek wrote a pretty good book about the infinite game, which explains how “winning” in work and life is different than winning at a board game or a sport or a spelling contest. When winning isn’t zero sum – you don’t have to lose for me to win – we play to perpetuate and improve the game, not to win it. When we play the infinite game sometimes losing is winning.

I’ve taken a few losses recently. From surprising critical feedback about my performance to the basketball team I coach losing by five points in the championship game to a really talented squad (they beat us by 40 in our third game of the season), I’ve spent a lot of willpower processing the losing. 

When we play the infinite game, though, we need to evaluate losses differently. If losing is winning sometimes, then what might that look and feel like?

Here are 10 examples of why losing is winning sometimes:

1. When you lose an argument and you learn something. 

2. When your team loses the game and it’s closer than expected or it’s against a really good team that kicked your ass earlier in the season. 

3. When you lose weight and maybe gain some muscle. 

4. When you lose at work but that reveals character in others, like the ones who put you down. 

5. When you lose track of time because you’re so in the flow of things. 

6. When you get lost in  the woods or in a city and then you find something cool. 

7. When you lose or let go of a skills or knowledge or way of doing things that was holding you back. 

8. When you tell people who were sucking your energy to get lost. 

9. When you lose track of time in an awesome conversation.

10. When you lose your keys, but find something cool (or that you lost a year ago) while you’re looking for them!

Sometimes it’s helpful to replace “but” with “and” because it helps break all-or-nothing thinking cycles by allowing two opposing realities or emotions to exist at the same time without negating either.

Here are 30 more ways losing is actually winning according to AI (Claude Sonnet 4.6):

1. When you lose a job that was slowly killing your soul — and it turns out to be the shove you needed.

2. When you lose a friendship that was built on who you used to be, not who you’re becoming.

3. When you lose a bid or proposal and the client who picked someone else calls you six months later.

4. When you lose your temper just enough to finally say the thing you’ve been swallowing for years.

5. When you lose interest in impressing people you never actually liked.

6. When you lose a mentor and are forced to become one.

7. When you lose sleep over something and the 3am clarity turns out to be worth it.

8. When you lose your place in line and end up in a conversation that changes your week.

9. When you lose a negotiation but gain a relationship.

10. When you lose your accent trying to fit in — and then reclaim it as identity.

11. When you lose your patience with mediocrity and it becomes a standard people respect.

12. When you lose the promotion and the person who got it flames out, proving your point.

13. When you lose a habit and realize the habit was a crutch.

14. When you lose followers for saying something true.

15. When you lose the early version of a project and rebuild it into something better.

16. When you lose a competition but your performance attracts someone who matters more than the trophy.

17. When you lose your phone for a day and realize how much you didn’t miss it.

18. When you lose enthusiasm for a goal and recognize it was someone else’s goal to begin with.

19. When you lose a vote in a meeting and the dissent gets remembered when things go sideways.

20. When you lose the plot of a conversation and your honest “wait, I’m lost” resets the room.

21. When you lose a belief that was comfortable but false.

22. When you lose your need for the last word.

23. When you lose custody of a project and it quietly fails without you.

24. When you lose your cool in front of the right person — and they respect the authenticity more than the composure.

25. When you lose a shortcut and the long way turns out to be the point.

26. When you lose the crowd but keep the right people.

27. When you lose a streak — gym, diet, productivity — and discover you can start again without drama.

28. When you lose the version of yourself that needed everyone’s approval.

29. When you lose access to something scarce and get creative in ways you wouldn’t have otherwise.

30. When you lose the argument you were winning — because you chose the relationship over being right.

Now get out there and build a healthy community.

Loser.

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John Horn is the Founder and Principal of Potentiality Consulting. Over the past 25 years, John has helped leaders reach their community-building potential, bringing a unique professional, intelligent and edutaining style to his seminars, presentations and essays. John applies his talents as a senior people and culture leader, coach (from youth athletes to executives), DIGITAL Canada Advisor, and as an advocate for career development, rare diseases (EPP), and building healthy communities. John lives in Victoria with his wife (who is her own person) and two kids - he loves exploring neighbourhoods via bicycle and making friends through basketball, boardgames, and conversations over coffee.