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Growth Is Uncomfortable

May 12, 2026

We've been talking a lot about learning new things lately. And more specifically — the fear that comes with it.

Things like: Take a course that actually challenges you. Describe the business you're building out loud. Play in a tennis league above your level.

We just did a new Fireside Chat about the fears that come with AI. What a rich area to explore!

Suzee and a few key people in my life have been relentless about pushing me out of my comfort zone — while pushing every single one of my buttons at the same time. (Yes, Suzee has been the early AI adopter of the two of us!)

But, honestly, that's exactly why I keep them around. 😉

Staying safe is easier. Staying where you already know things, where effort pays off predictably — that's comfortable. But growth lives in the places where you're a little shaky, where mistakes happen, and where you don't always look like you know what you're doing.

Yes, I'm going to talk about Tennis AGAIN

I came across an article recently about a new book — The Island Club by Nicola Harrison. The article is essentially the origin story of how I started my own tennis team. I could have written it myself. Except I'm not that kind of a writer (yet! who knows!). The article, titled "I Learned to Play Tennis After 40. It Completely Changed My Life", is about starting something new, as an "older" person, not knowing exactly how or why, and being surprised about the amazing outcome. I'm reflecting on this a lot especially as I dole out advice to my about-to-be-freshmen daughters (one high school and one college) about being open to new things and people, and the magical possibilities that can come with doing that, while acknowledging how scary and uncomfortable it can be.

I said yes to a tennis lesson around Covid lockdown after many year of not thinking about picking up a racquet. It was awkward. Physically trying to do something new and regaining that coordination ... I giggle at thinking of those first swings. Five years later, I'm obsessed with the game and the people I play it with, and I'm so much better skill-wise. (Shoutout to The Racq Pacq — you'll surely hear more about them if you stick around.)

This passage from Harrison's article hit close to home:

"I came to tennis late, awkward and for reasons that had very little to do with the sport itself. And yet, against all logic, it has become a huge part of my life. It's given me newfound confidence, a passion I didn't realize I was missing, and a community that has changed my daily life. It taught me that it's never too late to be new at something, and that sometimes the best things start not with ambition but with reluctance, and a simple, if hesitant, yes."

Five years in, I can say the same — real growth in skill, confidence, and community. And they curiosity and confidence that come from learning new skills can certainly influence other things (hello needlepointing and second- hand sewing machine!)

The community piece is what I want to focus on.

Every awkward moment, every mistake, every "I have no idea what I'm doing", has been manageable because other people were right there in it with me. Or because someone I trusted showed me a different way to look at something.

That dynamic is what Suzee and I have built together, and it's what we're trying to create through SEAR.

Take AI as a good example. A few months ago it felt too big and too technical to even approach. But working through it alongside others in our SEAR Masterclass in the Practice Lab changed that. I'm not an expert. But I'm learning, and I'm not intimidated (as much!) by it anymore. That shift came from doing it in this community. Practice ... not perfection.

New things are hard. They come with mistakes and sometimes real disappointment. But the experience is different when you're not navigating it alone. You have support, encouragement and the thought power of multiple perspectives!

Two things to sit with this week:

1. Where are you trying something new right now? Good. Stay with it.

2. Do you have anyone doing it alongside you? If not, is there someone you could bring in?

If you're looking for that kind of community, we're here for you.

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