Curiosity Killed My Elevator Pitch

The wind was crisp, the pumpkins were smug, and the other parents were chatty. It was a picture-perfect fall morning in the park this past Sunday. My daughter was off collecting leaves like they were currency, I had a coffee in hand, and then it happened.

“So… what do you do?” 

There it was - the question. Harmless, innocent, and yet somehow the conversational equivalent of being asked to summarize your entire existence in thirty seconds or less. I should have a tight answer by now. Something breezy but confident: “I work in product strategy,” or “I’m between opportunities,” or even the ever-vague “consulting.” But I don’t.

Instead, I smiled and said, “I’m taking some time off to be at home.”

Not a total lie, but not the truth either. Because I’m not “taking” time off; time is kind of taking me. My days are a rotation of networking calls, job applications, online courses, and the occasional existential crisis disguised as a run along the Hudson. Yet somehow, “taking time off” sounded better than “trying to reinvent myself while keeping a toddler alive and a marriage functional in the most expensive city in America.”

But the minute I said it, I could feel the curiosity spreading across the playground like gossip. The side-glances. The mental math. Was I a trust-fund dad? Independently wealthy? Or maybe my husband made enough that I could “pursue my passions”? (Spoiler: the passion is figuring out what the hell I’m doing next.)

The truth is, curiosity is both my problem and my superpower.

If I’m honest, I’ve never been a “domain expert.” I’m not the guy for one thing. I’m just a guy who’s pretty good at a lot of things… eventually. I can learn almost anything if I’m interested enough. That’s been my secret weapon for most of my career: curiosity. It’s gotten me promotions, projects, and the occasional imposter syndrome flare-up.

But lately, curiosity has started to feel less like a strength and more like a crowded subway at rush hour… too many directions, nowhere to sit.

I’m exploring everything right now. AI tools, new business ideas, writing, volunteering, maybe even politics. I’m exercising more, baking more, and occasionally wondering if I missed my calling as a wellness coach who makes a killer sourdough. Every week there’s a new spark: a podcast, a class, a “what if.” It’s intoxicating… and exhausting.

Somewhere in the middle of all that curiosity, I’ve started to wonder if I’m actually searching for my next career… or just chasing the high of possibility.

Speaking of curiosity, the universe gave me the second season of Nobody Wants This on Netflix last week… clearly their way of giving me a birthday gift.

I loved the first season. It’s perfectly bingeworthy in episode length, light enough to make you laugh, and still sneaks in a few gut punches of self-awareness. The second season? Equally charming. But as I watched, I found myself curiously thinking not just about the plot, but about us.

Without spoiling anything, the show orbits around love, family, and religion - three things that have been making humans messy since forever. And I kept asking myself: why is religion still such a deal breaker for people?

The Judaism portrayed in the show feels warm, human, familiar. Different rituals, sure, but the same search for meaning that runs through everyone. So why, I kept wondering, is Joanne (one of the main characters for those of you not watching) so reluctant to convert? Especially when she’s not even particularly religious herself?

I’m not looking for an answer, but I am fascinated by the question.

Personally, I pray regularly. I believe in something bigger. I try to live in gratitude often. But watching that show made me wonder: does it really matter which faith you belong to if the end goal is to live with purpose and compassion?

Because when I zoom out - when I look at the country we live in - religion feels like a funhouse mirror. A tool meant to teach love, empathy, and humility that somehow gets warped into judgment, exclusion, and sometimes, cruelty (MAGA Christians, I’m looking at you. And yes, I know I promised to keep politics out of this).

The show held up a mirror - not just to relationships, but to the contradictions we live with as a society. It’s not just about faith… it’s about how we practice (or fail to practice) the values we claim to believe in.

The other thing I couldn’t stop thinking about? The sisters, Joanne and Morgan. They have to be around my age (late thirties, nearing forty) and, well, they’re a bit of a mess. But in the most relatable, millennial way possible.

Their dad came out as gay later in life. Their parents were married most of their childhood. They’re processing old family stuff while trying to build new versions of themselves. Sound familiar? Not exactly my plot line, but plenty of similarities. 

It hit me that our generation has quietly been carrying a kind of collective emotional hangover. We were raised by parents who were doing their best with limited emotional vocabulary, in a world that changed faster than anyone could process. And now, here we are in therapy, meditating, manifesting, baking, biohacking, and trying to undo patterns we didn’t even know we had.

I don’t know what to call it… generational PTSD? delayed adulthood? the millennial malaise?,  but mark my words: someday there’s going to be a scientific breakthrough that explains exactly why our entire generation is simultaneously overachieving and falling apart.

And maybe that’s the real millennial riddle - we’re all chasing growth, healing, reinvention, enlightenment. But at what point do we stop chasing and just… arrive?

Is this it? - this endless curiosity loop, this search for what’s next - or is “it” the quiet knowing that curiosity itself is the destination?

So maybe that’s why curiosity feels so complicated lately. It’s not just about learning new things - it’s about unlearning old ones.

Curiosity pushes me forward, but it also makes me question everything: my faith, my career, my place in the world, even the way I answer small talk on the playground. It’s the common thread through all of it: the desire to understand what’s next, who I am, and what really matters.

As I packed up our things and called my daughter, I thought: maybe “I’m taking time off to be at home” isn’t such a bad answer after all. Because for the first time in a long time, I am home in the uncertainty, in the exploration, in the curiosity that just won’t quit.

Maybe curiosity isn’t about finding the next big thing. Maybe it’s about staying open to what’s already here.

And who knows… maybe that’s the whole point.

As a fellow New Yorker trying to make sense of money, meaning, and midlife reinvention, I’ve got to hand it to Scott Galloway — his newsletter No Mercy / No Malice nails it every week.

Think of it as tough love for the intellectually curious. It’s data, wit, and reality checks - all delivered before you finish your first cold brew.

The weekly section where I will call out a fraction: something that felt like progress this week (like a fraction forward) and a fiction: something that turned out to be a distraction or illusion. 

🎯 Fraction: It’s never too late to reboot your career  - just ask Flavor Flav, who’s now the official hype man for the U.S. bobsleigh and skeleton teams. If that’s not proof that reinvention has no age limit (or job description), I don’t know what is. Somewhere out there, a motivational speaker just retired.

🎭 Fiction: Every meteorologist, influencer, and coat brand is warning that this will be NYC’s coldest winter in years, which feels suspiciously like a marketing strategy disguised as meteorology. I’m not saying the forecasts are fake, but I am saying my Amex statement now includes a “weather anxiety” line item.

If Bill Gates is right and climate change might actually be slightly exaggerated, maybe we’ll all be fine in our new wool trenches come February.

A quick round-up of clips, headlines or stories, and cultural crumbs that made me pause and ask… is this it?

💼 More Layoffs, Less Loyalty
Amazon, UPS, and PwC are the latest to slash workforces… proving that “job stability” might now be a myth told by our parents. Corporate America’s favorite fall tradition continues: cutting costs while preaching culture. Meanwhile…

🚀 OpenAI Eyes a $1 Trillion IPO
OpenAI is reportedly preparing for an IPO that could value it at a cool trillion. Somewhere, a chatbot is practicing its investor-day remarks.

🤖 The Pregnant Politician (Sort Of)
In Albania, a government-run AI chatbot just announced it’s pregnant. Yes, really. Equal parts performance art and PR experiment, it’s the latest proof that even artificial intelligence wants a little attention (and maybe maternity leave).

🎃 The Great Pumpkin Arms Race
Twin brothers in the U.K. grew a 2,819-pound pumpkin; edging ever closer to a 3,000-pound world record. It’s equal parts science, sweat, and obsession… or as millennials call it, a hobby with existential stakes.

🧟‍♂️ “Monster Mash” Is Getting the Hollywood Treatment
The novelty Halloween song we all know is about to become a full-length movie, courtesy of Miramax. Because apparently, the scariest part of Halloween now is what counts as intellectual property.

If this one stirred a little curiosity in you - about yourself, your faith, or just what the hell we’re all doing here - forward it to three friends who love a good existential scroll.

Curiosity might not give us the answers, but it sure keeps the conversation interesting.

Until next Friday,
Chris

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