Yesterday, I was flat on my back, getting professionally stretched, my body creaking like an old door. It’s a bi-weekly ritual I lean into hard—it keeps me flexible, and helps me heal from years of grinding through life’s chaos. The woman working me over, a 24-year-old just starting her career, hit me with a question out of nowhere: “You’ve been around—what’ve you done to set yourself up financially that I should know?”
I laughed. A real, barking laugh.
“You’re asking me? You think I’ve got my shit together?” Her question caught me off guard, like a jab to the ribs. I’m no sage. My financial path looks more like a drunken stumble than a victory lap.
All I could give her at the moment was a half-assed list of regrets. “Here’s what I didn’t do,” I said, my voice trailing off. Don’t skip saving early, even if it’s just a few bucks a month. Don’t bet big on “sure thing” investments that crash and burn—I’ve got scars from those. Don’t let pride stop you from asking for help when you’re drowning...
It wasn’t the TED Talk she deserved. It felt like I was reading my failures out loud, each one a reminder of where I’d screwed up. Driving home, I felt heavy, almost depressed. Why couldn’t I have given her something polished, something wise? Why did her question make me feel so damn exposed?
But in the 24 hours since, I’ve been chewing on that moment, and I’m starting to feel different.
There’s something real in what I said, even if it was messy. My mistakes aren’t just fuck-ups—they’re lessons, hard-earned and raw. I’m not saying emulate me. Hell no. But listen to where I went wrong. There’s gold in those missteps.
I wish I’d stashed away 10% of my income in my 20s, even when I thought I had nothing to spare. I wish I hadn’t over-leveraged into short-premium options strategies that almost put me out of business permanently. I wish I’d been humble enough to ask for advice when I was in over my head, instead of pretending I had it all figured out. That’s not just regret. That’s a roadmap for anyone starting out.
What I love about this woman is that she’s already asking for guidance. At 24, she’s out here seeking wisdom, unafraid to admit she doesn’t know it all. That’s a superpower I never had. Asking for help has always been my kryptonite. Maybe I’m projecting, but I think it’s especially hard for men.
And for traders like me? Forget it.
There’s this unspoken code: act like you’ve got it all under control, even when you’re bleeding out. I’ve lost count of the times I stayed silent when I should’ve reached out, thinking I had to solve it alone. It cost me. Big time.
She’s different. She’s smart. Her question wasn’t just brave—it was a reminder that no one gets far without leaning on others. The best traders I know, the ones who survive the market’s meat grinder, have mentors, sounding boards, and people they trust to call them out. If I could go back, I’d tell my younger self to drop the lone-wolf act and ask for help. It’s not a weakness. It’s how you grow.
So I'm going to do something a little nuts.
Here's my phone number: 312-498-4519.
If you’re reading this and you’re stuck—on money, work, life—call me. Leave a voicemail and I’ll call you back. Or text me if that’s your thing.
I might regret blasting my number out to the world. But my heart’s screaming that someone out there needs to be heard, needs a nudge to keep going. I’m not a guru. My track record proves that. But I can listen. I can share the scars I’ve earned. I can tell you what I learned the hard way so you don’t have to.
That stretch session left me sore, but it also left me grateful. Her question forced me to face my past—not with shame, but with clarity. My mistakes don’t define me. They’ve shaped me. And that's true for you too. If I can help one person dodge the traps I fell into, that’s enough.
So, to her, and you: don’t chase perfect. Chase the lessons. Ask the questions. And if you need someone to talk to, you know where to find me.
Sean McLaughlin | Chief Options Strategist, All Star Charts
