Let Winners Run: How to Ride Trends and Avoid Cutting Profits Too Early

When you hear let winners run, the practice of holding onto profitable investments instead of selling too soon, it sounds simple—until your stock jumps 30% and you panic-sell at 15% just to lock in a win. That’s the trap. momentum investing, buying assets that are already rising because trends tend to keep going isn’t about guessing the future—it’s about riding the wave you can see. And portfolio drift, when your holdings shift out of balance because some assets grow faster than others isn’t always a problem to fix immediately. Sometimes, it’s proof your strategy is working.

Most investors get scared when a stock rises too fast. They think, "It’s due for a drop," and sell. But history shows the biggest gains don’t come from buying low and selling high—they come from holding on while others bail. Think of it like a train: you don’t jump off just because it’s moving fast. You wait until it reaches your stop. That’s what trend following, a strategy that uses price movement to decide when to enter or exit is all about. It doesn’t care why something is rising—only that it is. And when you combine that with smart rebalancing, the process of adjusting your portfolio to maintain your target allocation, you don’t let winners run wild—you let them run *strategically*. You don’t sell just because they’re up. You sell when the trend breaks, or when your overall mix gets too skewed. That’s the difference between emotion and discipline.

The posts below show you how this plays out in real portfolios. You’ll see how momentum investing beats value strategies in bull markets, how portfolio drift can quietly turn a balanced portfolio into a risky one, and why rebalancing too often kills your gains. You’ll also learn how robo-advisors automate letting winners run while keeping risk in check, how ETF tax lot management helps you keep more of your profits, and why the bucket strategy lets you lock in gains without touching your long-term holdings. This isn’t about chasing hot stocks. It’s about building a system that lets your best ideas work for you—without you second-guessing every uptick.