On Raising Generalists, Riding Market Waves, and Reading the Future
Jordan DiPietro
May 15, 2025
Hey —
Starting a new section here at the top, “While I Was Writing”…
feeling a little trippy, pulsing groove — from the Kentucky-born psych-rock band that made reverb into a religion:
From sound to signal—let’s get this baby rolling with what’s on my mind this week…
// The Signal
On youth sports, career anxiety, and keeping space to explore
One of the things that’s been on my mind lately—as a dad of two kids, 10 and 7—is how much youth sports have changed, & what that shift says about how we’re raising our kids.
When I was growing up, sports were just… sports.
You played whatever was in season—basketball, baseball, soccer, football. Maybe lacrosse if you were extra. Summers meant day camp and a blend of weird-ass activities: swimming, riflery, inexplicable bouts of archery, woodshop, wandering around in nature. BMX bikes and skateboards ruled the neighborhood.
And we had one local league. Some kids who really loved a sport—usually soccer or lax—begged their parents to join travel teams. But most of us dabbled in everything; you didn’t specialize until high school, when time became a zero-sum game.
Today—in a post–Malcolm Gladwell, 10,000-hour-obsessed world—parents are niching their kids down before they hit second grade. Travel teams start in elementary school, fueled by an unrelenting desire for kids to “excel” and help reconcile their parents unfinished dreams.
Beyond the emotional costs, there's the undeniable expense of trekking to random corners of rural America each weekend, watching your kids compete against other privileged kids in soccer, baseball, or basketball, not to mention whether or not it’s actually the best thing for you and your family.
I’m not trying to be a hater — if your kid loves a sport—if they wake up early, drag you to the field, and live for it—then fuck yeah, go all in. That’s a beautiful thing.
But for the majority of kids? The ones who just want to play, try stuff, and hang with friends? What’s the harm in loosening up?
Childhood shouldn’t be padding a résumé in preparation for elite college applications.
Kids need to become themselves, and it’s not just structure they need—but actual space.
I’ve been thinking about all this in the context of my own kids—and my own ‘adult’ path.
Maybe I’m more sensitive to it because I’ve always been a generalist, or as Gen Z calls it, a “multi-hyphenate” (god they love labels).
As a kid, I was into sports, girls, beat poetry; later it was chess, psychology, books on Cuban history; in college I got deep into writing, chef memoirs, & Modest Mouse. These days it’s still writing; along with being a Dad, cooking, investing, working out, and still reading as much as I can.
As Ryan Holiday has pointed out, we used to actually admire RANGE.
Benny Boy Franklin was a printer, publisher, inventor, postmaster, diplomat, and civic activist. Marcus Aurelius ruled an empire and practiced Stoic philosophy. Jerry Garcia played a mean psychedelic guitar, was an avid painter, and logged hundreds of hours as a scuba diver.
Being multi-faceted was an asset. Your interests informed each other. They made you better.
In my own career, that mix has always helped me:
-Writing got me my first dream job (in finance).
-Curiosity about data pulled me into product.
-Each rabbit hole opened a new door. No master plan. Just following threads.
Which is why it guts me when ambitious young people ask me the same anxious question:
😨 What should I specialize in?
Just last year, a high-performer I managed told me he thought he had to “choose a path” to keep advancing. I couldn’t help but picture the years of niche clubs, elite teams, tightly programmed summers—all of it funneling him to that moment of anxiety.
And all I wanted to say—and eventually did—was this:
Relax. Keep moving the needle. Focus on making an impact with what lights you up.
The rest will follow.
In my opinion, success doesn’t come from picking the right lane early.
It comes from building a wide, resilient, interesting life—one full of experiments, detours, weird-ass books, Sunday tennis matches, and new obsessions you don’t see coming
Range matters - for your career, for your kids, for your sanity.
🔖 The Blog Round
Pull back the bears and make room for the bulls?
After nearly two brutal months of red, the market decided it wasn’t dead yet. Despite tariffs, AI slowdown talk, and a chorus of doom from finance Twitter, equities staged one of the fastest comebacks in recent memory.
When my sister asked me last week what all this meant for her IRA, I told her the truth:
I have no effing idea.
And looking at the chart below, I wouldn’t have predicted it either.
So what sparked the rebound? A mixed platter of good news:
S&P 500 Earnings surprised to the upside, growing +12.9% YoY
AI demand still roaring—more GPUs, more server farms, more capex baby
A surprise UK trade agreement, plus Trump’s “This is just the beginning” message to Wall Street
It’s a good reminder of the oldest advice in the book: buy and hold.
👀 A few Jawns to Check Out
➡️ Gregg Popovich, Builder of Dynasties. Popovich—the longest-tenured coach in pro sports history—just officially stepped down as head coach of the Spurs after five NBA titles, 1,366 wins, and nearly three decades at the helm. This piece isn’t just for basketball nerds; it’s a masterclass in leadership, humility, and playing the long game. If you're building anything—teams, companies, cultures—there’s something here for you. 📕Check It Out.
➡️ The Robots are Here. Back in 2016, The Guardian warned that AI could lead to mass unemployment—and even the rise of a “useless class.” Nearly a decade later, former Google CEO Eric Schmidt is raising flags about the energy it takes to power all this AI. And now? The Semafor piece on giant data centers quietly swallowing up Virginia suburbs reads like science fiction. Except it’s not. 📕Check It Out.
➡️ A Great Curated Reading List. If you like your book recs thoughtful and slightly intense, Ryan Holiday still delivers. His April picks just dropped — along with back issues from January to March. My favorites so far: The Road (haunting), James (understated and brilliant), An Empire of Pain (epic rage read), and Say Nothing (chilling and historical). 📕 Check it out.
Alright playas, that’s all for now.
Please feel free to forward this along to someone who’d dig it - or just hit reply and tell me what you liked (or didn’t).
Love yous.
Jordan