I'm Rolling Into Fifty

I talk a lot around here about the “Hundred-Dolla-Roll.”

For those unfamiliar, it’s a phenomenon I’ve observed many times in trading: When a stock approaches a big, round number—$100, $200, $300—for the first time, it often acts as a magnet. Traders are drawn to that number. They anticipate it. They envision profits. They start to dream. And in the process, they learn a lot about the strength (or weakness) of the demand behind the move.

Big round numbers matter.

And today, I’ve hit a big one myself.

I turn 50 years old.

Strangely—I’ve been looking forward to it. I feel like I’m approaching my own hundred-dolla-roll moment. Like I’m entering a new phase of my life where magic is about to happen—across all domains: work, trading, community, relationships, and most importantly, the relationship I have with myself.

It’s a funny thing to say out loud, but I genuinely feel like I’m just getting started.

I’ve been doing a lot of reflecting lately. And one of the things I keep coming back to is this idea of purpose.

We all talk about it. We all say we’re looking for it. And most of us, if we’re honest, are still circling around it. But when you meet someone who has found their purpose—you feel it. It radiates off them. There’s a calmness. A clarity. A direction.

I can’t say I’ve fully found mine yet. But I know I’m closer than I’ve ever been.

And what’s been showing up for me lately is this idea of holding space and bearing witness.

I know that might sound a little woo-woo, but stay with me.

To hold space means to create room—for people, for ideas, for emotions, for growth. It’s not about fixing or forcing. It’s about presence and openness. And in looking back over my life and career, I can see now that this has always been part of what I do.

When I was working on trading desks, it was there.

When I was building communities at StockTwits, it was there.

When I started my trader meetup group in Colorado, it was there.

And in the work I do now—with All Star Charts, with options education, with all of you—it’s still there.

That throughline has been connection. Curiosity. Community. Making space for people to share their ideas, their energy, their wins and losses, their fears and hopes. Not needing to be the smartest person in the room. Just being there. Fully. And bearing witness to come what may -- The great, the good, the bad, and the ugly.

Even in trading, this concept applies. I can’t control the outcome of a trade. I can’t will a stock to move. But I can put on a position with intention. I can create space for the trade to play out. And then I can bear witness—win or lose.

That’s the game. And it’s also the work.

I don’t have it all figured out. But I’ve never felt more equipped, more supported, and more clear about the direction I want to go.

So, Happy Fifty-Year-Roll to me!

To the me I’ve been becoming.

To the me I’m still discovering.

Let’s roll.