You Can't Go Broke Taking Profits - And Other Dangerous Wall Street Sayings

"You can't go broke taking profits." It's one of the most repeated phrases on Wall Street—and one of the most misunderstood. In this episode of Thinking In Options, Bill Johnson dismantles the comforting myth that locking in gains automatically makes you safer. Using vivid analogies—from notorious bank robber Willie Sutton to Wile E. Coyote—Bill explains why consistently taking small profits while exposing yourself to the same downside risk can quietly sabotage long-term performance. This episode dives into the real driver of trading success: payoff asymmetry. Why strategies that "win" most of the time can still lose money. Why frequent small gains may actually mask hidden tail risk. And why true risk management isn't about how often you profit—but how your gains and losses are structured over time. You'll learn: Why early profit-taking can reduce reward without reducing risk The hidden danger of "negative skew" strategies How traders confuse realized gains with actual safety Why probability and payoff—not win rate—determine long-term results If you've ever felt safer closing trades quickly, this episode will challenge that instinct—and give you a more accurate framework for evaluating risk. Because in trading, the real danger isn't taking profits… it's believing they protect you.