Money exposes mindset. A hot trade, a plane ride, and a missed exit once cost me nearly a million on paper. The lesson wasn’t about markets. It was about the story we tell ourselves when things don’t go our way. My stance is simple: stop calling it a loss and start measuring the return on your decisions.
This isn’t spin. It’s responsibility. Regret is a tax on attention. When we trade “should’ve” and “would’ve” for clear math and clear choices, we gain control of our future.
“I don’t believe in loss or sacrifice. I believe in I’ve made this investment, what’s my return?”
The Myth of “Loss”
Years ago, a $60,000 position ran up to $985,000 in gains on paper. I expected big news to hit. My wife said, sell. I held. By the time the plane touched down in Vancouver, my stop loss triggered and the position closed back near even. The old voice kicked in: you just lost $985,000. That voice was wrong.
The only true loss is the failure to learn. Gains you didn’t lock aren’t yours. Paper profits are not purchase orders for your dreams. Calling it a loss is a way to dodge ownership of process.
“I was like, oh, no. The news will come out. It’s gonna go higher… By the time I landed… I broke even.”
What changed since then? I stopped defining outcomes as identity. I now define outcomes as data. That shift turned regret into a return on experience.
Process Over Outcome
Winning is a habit. So is self-sabotage. What separates the two is process. Honor your rules more than your hopes. Hopes aren’t bad; they’re just not a strategy. Rules are.
- Decide exits in advance. Price, time, and thesis-based: write them down.
- Sell into strength when signals fire. Celebrate discipline, not drama.
- Protect downside with stops or hedges, then accept the result.
- Review decisions by process quality, not by dollar swings.
- Separate math from meaning. Your worth isn’t your last trade.
These rules reduce noise. They also reduce shame, which is the real drag on performance.
From Regret to Responsibility
Another trap is the story we use to delay action. Back then, I said, “I could have retired my mom.” That sentence feels noble—and it lets you off the hook. It swaps a clear commitment for a fantasy headline.
“Now if I want to retire my mom, then I’ll retire my mom… I won’t make up some story how I could’ve, should’ve, or would’ve.”
Goals are not IOUs written to your past self. They are choices you fund with current behavior. If something matters, set the number, set the date, and set the plan. Then do it when the criteria are met.
But What About Leaving Money on the Table?
Common pushback: “If you sell, you might miss the real run.” True. You also might protect capital for the next great shot. One outcome feeds ego. The other fuels compounding. The goal isn’t to catch tops; it’s to build a repeatable engine that survives mistakes and scales wins.
I led a sports agency and now chair the Napoleon Hill Institute. Performance is pattern. The best performers detach from outcomes without detaching from standards. They don’t worship gains. They honor decisions.
What To Do Next
Adopt a simple scorecard. Define investments by return on risk, return on time, and return on learning. Use post-mortems that ask: Did the decision match the rule? Was the rule sound? What will improve the next choice? Then, act on what matters most to you now, not what would have looked great on a plane ride.
“As soon as I get to that point I’m gonna do it.”
The opinion, and the invitation: Treat every outcome as feedback. Retire your excuses before you retire anyone else. Decide, commit, and let the math—not the myth—guide the next move.
Frequently Asked Questions
Q: How do I stop fixating on missed profits?
Replace “what it could have been” with “what I planned.” Evaluate each choice by whether it followed your rules. Bank the lesson, not the shame.
Q: What’s a simple rule set for exits?
Pre-set a target to trim, a stop to protect capital, and a thesis invalidation point. If any trigger hits, execute without debate.
Q: How do I fund meaningful goals without waiting on a big win?
Price the goal, automate contributions, and tie it to steady returns. Let process do the heavy lifting rather than one hail-mary trade.
Q: Isn’t patience key to bigger outcomes?
Yes—patient with the plan, not passive with the rules. Patience is holding the system. Passivity is ignoring signals.
Q: What’s the best way to run a post-mortem?
Write down the decision, the rule behind it, the result, and one improvement. Keep it one page. Review weekly to keep bias in check.
