The Art of Holding Winners (And Why It Hurts So Much)
September 11, 2025
Let's talk about something that's probably eating at you right now: those big winners sitting in your portfolio.
You know the ones. The positions that have doubled. Maybe tripled. The trades that are making you nervous because they've moved so far in your favor that giving any of it back feels like a personal failure.
Here's the uncomfortable truth: we're at a point in this market where many of us are holding some seriously large winners. And every fiber of our being is screaming to take risk off the table and book these gains.
There's nothing wrong with that impulse. You have to do what makes you feel comfortable. Risk management is personal, and nobody else has to live with your decisions.
But here's the thing that nobody wants to admit: the moves we make in the markets to feel comfortable rarely result in winning big. Winning bigly—and I mean really winning—is fundamentally uncomfortable. There's no way to sugar coat that reality.
Trust me, I have a million regrets about not getting out of positions when I had sizable gains. Watching winners roll over and never come back, knowing in hindsight that I was being greedy? That hurts. It stings in a way that cuts deep because you had it, and then you didn't.
But you know what hurts even more?
Watching positions rip without you because you took profits too early.
Take this $RDDT trade from earlier this summer. In a shorter-term account I manage, I had this beautiful entry on June 16th and solid paper gains building. By July 9th, I was sitting pretty, but I started getting nervous about giving back too much of what I'd made.
So I exited. Took my profits like a responsible trader.
Big mistake.
Had I held that trade, it could've been one of those positions I look back on as the one that made my year. Instead, it became a painful lesson in the cost of playing it safe. Watching $RDDT continue its march higher without me? That's a special kind of trading torture.
The reality is that holding winners might be the hardest part of this entire game. Don't let anybody tell you differently.
Think about the psychology for a minute. When you're down on a position, you can always tell yourself it might come back. Hope springs eternal. But when you're sitting on massive gains, every tick against you feels like money being stolen from your account.
The market seems to sense this weakness too. Those beautiful uptrends have a way of shaking out paper hands with just enough volatility to make you question whether the move is over.
Here's what I've learned after years of wrestling with this: the art isn't just in knowing when to take profits. It's in knowing how to give your winners enough room to become true home runs while protecting yourself from complete disaster.
That's exactly what we'll be working through in today's Live Options Jam Session. We're going to do that delicate dance of updating stops on open positions—trying to give working trades enough breathing room to push to new highs while not being complete idiots about risk management.
It's more art than science, honestly. Too tight, and you choke off positions that could be legendary. Too loose, and you watch beautiful gains evaporate.
The goal isn't perfection. It's finding that sweet spot where you can sleep at night but still participate in those moves that can genuinely change your account trajectory.
Because here's what I know for sure: the biggest regrets in trading aren't usually about the losses. They're about the wins we didn't let run far enough.
