Stop Playing Losing Games
Losing Games
Recently in our coaching group, we talked about a big truth: sometimes the game you’re playing is unwinnable. No matter how much effort, perfection, or force you throw at it—you’ll never feel like you’re winning.
What’s a losing game? It’s a situation or mindset you’re in that no matter how hard you try, you can’t truly “win” because the game itself is unwinnable. There’s two paths you can take:
continue playing the game that you’ll never win, or
take your hand off the joystick and stop playing the unwinnable game
Here’s two real-life examples we talked through with our coaching group:
Chasing an endless to-do list: A mom and business owner who is trying to complete her ever-growing to-do list and be present in the evenings with her family. The unwinnable game is that she will never complete this to-do list. As a business owner, there’s always something to fix, an email to respond to, a newsletter to write, and sales to make. The reframe is to stop trying to get it all done, and instead focus on her family, then do the 1-2 most meaningful things and understand the rest will fall off or wait.
You’re always in repair mode with a relationship: An employee is working hard and coming up with creative ideas, but her boss is never satisfied. The employee is stretching herself thin, trying to impress her boss, but it never feels like enough. The unwinnable game is that she will never please her boss. Her choice is to stay and accept that she is doing the best she can, or leave and find a new boss who values her.
Anna’s Sabbatical Work Week Experiment
Anna: Let me update you on the unwinnable game I’ve been playing.
I thought that I’d finally be at peace if only I had full control over my schedule. Well hello there, I’m on sabbatical and I sure do. So I set about planning my weeks. M-F I’ll work 10a-4p. Saturday and Sunday are free days, normal weekends. During the work week, I’d be able to have an amazing morning routine before 10 am and then enjoy cooking and a sunset dinner after work. For my working hours, I’d write daily, work on The Evolved Vets, and have plentiful time to clear through my to-do lists and emails.
Well, I’m 0 out of 4 in my weeks that have gone according to that plan. Not to say they’re so far off, but it’s not as simple as I imagined.
Where I’m Doing Well
Putting my phone in another room when I sleep and not checking it until about an hour after I wake up naturally
Exploring outside with François and journaling with coffee in the mornings
Going on a 20 minute walking meditation
Writing and sharing daily
Going on evening walks with Ash
Enjoying my weekends
Where I’m Running Into Old Habits
When I check my phone around 8 am it takes me down rabbit holes and pivots
When I sit down to work, my writing takes up 80% of the time, then posting about it always takes longer than expected
I start another piece of work, get carried away, and before I know it it’s 7p
I’m so hard on myself when I don’t get to my MITs
I’m spending too much time caring about social media
My losing game: Trying to use my sabbatical to “finally get to everything I want to do,” while still operating from the belief that if I could just manage my time better, I could fit it all in.
Why It’s a Losing Game
My list is infinite - As soon as I check something off, three more things I “want” to do or feel like I “should” do appear. I’ll never arrive.
The rules are unwinnable - I’m measuring success by “getting it all done,” but the “all” keeps expanding.
I’m treating time like a container to be filled perfectly - Oh boy this is the toughy. Instead of accepting that there will ALWAYS be tradeoffs, I’m still hoping for the perfect allocation. Reminder to self to write about tradeoffs.
I risk missing the whole point - My sabbatical was supposed to give me space, not replicate the pressure of work under a different label. Ugh.
Do This Exercise if You’re Playing a Losing Game
No really, do it now. Bring to mind the losing game you’ve been playing. Stick your hand out. Visualize your hand on the joystick, playing the losing game. Then stop. Lift your hand. Physically pull your hand back. Let it go.
The only way to win is to stop playing.
The Reframe
“Winning” is doing what matters most. Right now. And letting go of the rest without guilt.
You cannot win a losing game. You’re not bad, selfish, or weak for giving up.
Ask yourself:
What’s the cost of not quitting this game?
Is this in alignment with my values?
If it’s a “maybe,” it’s a NO.
If it’s a HELL YES, what boundaries protect it?
Final Takeaway
✨ You cannot win a losing game. But you can choose a different one.
Choose the game that fuels your energy, aligns with your values, and gives you space to live. That’s what true winning is.
