Year Two

A year of being chosen and unchosen

Scott Simon

Dec 17, 2025

This Week’s Courage Newsletter

“I was ashamed of myself when I realized life was a costume party and I attended with my real face.” - Franz Kafka

Dearest friend,

This was my second year on my own.

I don’t know what I expected.

Maybe I thought by now there would be some kind of arrival - a moment where I’d look around and think ah, yes, I have built the thing I left to build.

Instead there’s just... more walking. Which I think is the point, but I’m still learning to trust that.

Let me tell you what happened:

There is no real estate company job holding a warm chair for me anymore. No quick morning coffees to catch up with friends, no drink after work to talk life.

I have missed people this year in a way that caught me off-guard - the kind of missing that sits in your chest and doesn’t announce itself until you’re alone in an airport wondering if you’ve traded belonging for something you can’t quite name yet.

My mom recovered from two strokes in 2024.

Miraculous doesn’t cover it.

But Parkinson’s is an evil and unforgiving disease and it is no longer welcome in our home.

My ex-wife and I moved both of our children into their places in the world. My daughter to the hustle of New York City, pursuing an MSW degree. My son to Michigan State, where he studies flashcards of diseases with names so long I can’t pronounce them in between sets at the gym.

(Noah and I visited the same East Lansing college bookstore where my parents met fifty years ago in the stacks, stood there trying to imagine them young and uncertain, and thought: this is what time does.)

I noticed how similar my kids and I have become, and how much of that happened without me engineering it.

I sat in the middle seat of row 32 on a 7:00 am flight more times than I can count, wedged between strangers, rehearsing a keynote in my head.

I committed to co-writing a second book with an iconic best-selling author, poured months into the proposal, and watched eight different traditional publishers say no.

Including the publisher of my first book.

There is a specific kind of silence that follows rejection - not dramatic, just quiet. You close the laptop and make dinner and the world keeps going and you think: okay, now what.

I was offered the chance to give the largest keynote of my career. Five thousand people. Healthcare professionals - the very people who saved my mom’s life. I prepared and interviewed like crazy.

And then I came in second.

But also:

I found my book - Scare Your Soul, with that luscious purple and maroon spine - in bookstores in every city I visited.

Each time, something in me still sparks.

I was hired by an NBA organization to bring courage workshops to their staff. Once. And then ten more times.

I gave a keynote in the Bavarian Alps that ended with hugs and high fives. The writer Brianna Wiest came up afterward and said my talk was “f*cking fire.” I have replayed that comment in my head approximately one thousand times.

Dana and I walked through the David Hockney exhibit at the Foundation Louis Vuitton in Paris, watched how he painted English winter trees with neon blues and greens instead of tans and grays, as if to say: you can look at the same thing a different way.

I stood one foot away from Warhol’s Marilyn in Pittsburgh. And I tried on a full-length buffalo jacket with matching horned helmet in the back of a knife store in Park City, Utah, for reasons I still cannot explain.

I co-ate a 19-course Indonesian meal in Amsterdam on a friend’s advice. Saw Wilco outdoors under the stars. Watched Goose put on an ethereal show at a small venue in Toronto and didn’t take a single video because I wanted to just be there.

I conducted my first courage workshop on a boat. I have no idea why this delights me so much, but it does.

I joked with my barber Brian about our mutual love of Lost, both of us still shivering when we talk about seeing Kate for the first time, still wrecked by the way Sun and Jin died in each other’s arms in that damn submarine.

It’s been over fifteen years and we’re still not over it.

I walked the quiet streets of Puerto Vallarta after a courage workshop, my cheap green Birkenstock plastic sandals kicking stones in the path like I was six years old again. The world felt, briefly, exactly right.

I received emails and texts and DMs from people around the world who read my book and just wanted to tell me they had done something brave. I don’t know how to describe what that feels like.

But it’s the opposite of lonely.

My identity was stolen by a wretch who tried to buy a Toyota in Illinois. (Unsuccessfully.)

I fell deeper into love with a woman who wants adventure as much as I do and who also wants to cuddle in bed with our dog and cat after the adventure is over. We adopted a foster cat - Neptune, King of the Seas - found under a porch in inner-city Cleveland and gave him a solid home.

I made dozens of homemade pizzas in my backyard oven and burned at least half of them and didn’t care a bit.

I plastered one whole window with Post-it notes as I worked my writing muscles, just like when Steven Pressfield says you must “put your ass where your heart wants to be.” I watched the sun filter through the treetops on park walks with Dana and Juni - walking, talking, laughing, planning, laughing again.

I re-became a beginner, immersing myself in the intersection of Judaism and Buddhism with Rabbi Robbie Schaefer in rural Virginia. Revisited Kripalu, my home-away-from-home in Lenox, Massachusetts, where I’ll be co-leading a workshop this January. Kayaked still waters in an early Berkshire morning, my paddle cutting glass.

I discovered the artist Mr. Bingo and his radical philosophy of completely not giving a shit while doing what you love. I think about that permission more than I expected to.

And here’s the thing I keep circling:

I don’t know what stage I’m in.

The second year of this new life isn’t arrival.

It’s just more walking.

Doors opened and closed, sometimes in the same week, sometimes the same day.

I was chosen and unchosen.

I mattered and I didn’t.

I showed up with my real face - no costume - and sometimes that worked and sometimes it didn’t and I keep doing it anyway.

Have you ever felt ready for your next stage but don’t know what it is yet?

Felt a deep longing for a cooler, more collected version of yourself that’s so tangibly close you wanted to just birth yourself out of your chest and make a run for it?

I don’t have answers. But I have this strange, stubborn faith that the walking is the point.

That the backpack I threw over the fence two years ago is still out there, waiting, and my only job is to keep moving toward it.

The choice is yours.

In courage,