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What Winning Actually Looks Like
I realized I was winning at the wrong game. Here is how I stopped chasing someone else’s scorecard and started actually living.

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In this issue:
The year I worked until 10pm on December 31st (and showed up to New Year's in stretch pants)
What teaching English in Kerala taught me about real success
The question that will change how you define "winning"
December 31st, 10pm
Still closing deals while everyone else was getting ready to celebrate. | ![]() But I was winning... right? |
Six months later, staring at another year-end forecast, I realized I was winning at the wrong game.
Read Past Issue: The Sunday Night Test and find out if stress is in charge of your life and what to do about it.
This year looks different

I'm writing this from Fort Kochi, Kerala, India.
My daughter and I start each day at 8:30, having breakfast with families from around the globe who value giving back. Indian flatbreads and chai. Then a tuk-tuk ride to our placement.
We teach English to 4 and 5-year-olds through songs and learning games.
These kids are brilliant. Their joy is pure.
Their excitement when they nail a new word? That's a feeling I can't get from any sales dashboard.
![]() | ![]() |
The photo of my daughter in that classroom that made me cry (see it here) → Link to Photos
But here's what I didn't expect:
Standing in the back of that classroom, watching my daughter fall in love with making a difference—that's the real win.
Not the quota. Not the year-end bonus. Not the 10pm close.
This. This is living.
And I'm so damn grateful to spend Christmas week this way.
The question I'm sitting with (and inviting you to consider)
What if the life you're chasing is actually keeping you from the life you want?
What if "winning" has been defined by someone else's scorecard?
Here's what I want you to do this week:
Write down three "wins" you're currently chasing. Then ask yourself:
Would 10-year-old you be proud of these?
Would 80-year-old you care about them?
What would winning look like if you defined it?
Read Past Issue: The Activation Tax and get a framework that will help you implement your winning vision.
That's all for this week.
Happy Holidays! Thank you for your support this year—it means more than you know.
See you next Tuesday.

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P.S. If you're reading this and feeling that pull—the one that says "there's more than this"—that's not burnout. That's your future self trying to get your attention. Let's talk about what's next →
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