You’re allowed the Joy Of Figuring it Out
💚 Welcome to the weekly newsletter for ambitious leaders staying sharp and staying human in the age of AI.
Every edition is:
Curated: One standout piece I read, watched, or listened to this week + my riff on what it means for you
Counterintuitive: A surprising angle that shifts how you see your day-to-day.
Cross-pollinated: Draws unexpected connections between the worlds I live in—sales, sports, and Stanford.
📬 If you like this, share it with a fellow leader. It’s a low-lift way to stay connected to the people you care about when your calendar has zero room for 30-minute Zoom catch ups.
The Problem
As high-achievers trying to have a big impact, so much feels important. Actually, everything feels important. And the pressure of making it all high-stakes is squeezing out the very joy that drew you in to take on the challenge in the first place.
The Discovery
The French Open is happening, a professional tennis tournament filled with high-achievers. One of my favorite moments from the tournament has been João Fonseca, 19, coming back from two sets down to win a jaw dropping, hooting and hollering match against Novak Djokovic, widely considered to be one of the greatest tennis players of all time.
Post-match, when the interviewer asked Fonseca how he kept believing he could win, he basically said: I didn’t.1
Specifically:
“I actually didn't. I just played. I just enjoyed being on court. What a pleasure it was. It’s a pleasure just stepping on the court against [Novak]. It’s my first time stepping on court against him. Just thanking him and just very happy.”
I loved this so much.
Because as leaders when you are trying to build something important, negotiate with a client, ask for a promotion, your brain can get into the mode where the future of everything depends on whether one person says yes by Friday.
It can get dramatic.
But Fonseca’s answer was such a clean reminder:
It can be intense, and it can still be fun.
It can be disappointing, and it can be fun.
It can be tiring, and it can be fun.
This is not just cute sports wisdom. It connects to Mihaly Csíkszentmihályi’s research on flow2, the state where challenge and skill meet in a way that makes people deeply absorbed in what they are doing.
Flow happens when something is difficult enough to require your full attention, but not so impossible that you collapse into panic. You lose self-consciousness. You stop obsessing over the outcome. You become more available to the next move.
The Experiment
This week, I want you to practice staying available to the work without making yourself miserable in the process.
Before your next high-stakes conversation, ask yourself:
1. Where am I gripping the outcome so tightly that I’m losing access to the actual work?
Notice where your brain has turned one meeting, one pitch, one conversation, or one decision into everything.
Then bring yourself back to the next point.
What is the next question to ask?
What is the next piece of information to understand?
What is the next honest sentence to say?
2. What would make this hard thing even 5% more fun?
Not easy or unserious. Fun.
Could you get curious about the other person’s resistance?
Could you treat the conversation like discovery?
Could you enjoy the craft of making your point more clearly?
Could you let yourself appreciate that you are in the arena at all?
The Takeaway
You worked hard to get into the room and into the role where the stakes are high. You’re allowed to enjoy being there. You’re allowed to relish the challenge, keep the curiosity alive in high-stress moments, and turn pressure into possibility. You’re allowed the Joy Of Figuring it Out.
Join the community of leaders staying sharp
and saying human in the age of AI.
