I always end up selling my winning stocks too early. How do you hold on for 10x or 100x returns?

Published 28 September 2026

Srujana from Pune
I have a terrible habit of booking profits the moment a stock doubles or triples.

I bought a few smallcap pharma and finance stocks a few years ago. I sold them when I made a 100% return thinking I was a genius.

Today those same stocks are up 10x from my original buy price. I feel sick looking at what I missed out on.

How do you develop the psychology to hold a winning stock for decades instead of booking early profits?
Sachin Kabra Sachin Kabra ex-Director HDFC Private Wealth, Business Head Motilal Oswal AMC LinkedIn
The greatest wealth in the stock market is created by identifying extraordinary opportunities early, backing visionary entrepreneurs and holding through extreme volatility for decades. Out of a population of 1.4 billion in India, only a tiny fraction of perhaps 10,000 to 15,000 individuals have created massive generational wealth in the stock market. What stops most people is the psychological complexity of dealing with massive unrealized gains and the temptation to lock them in.

Imagine buying into a pharma company's IPO when its total market cap was a mere Rs 140 Crores. Many early investors might exit when the market cap hits Rs 2000 Crores thinking they made a massive return and feeling incredibly smart. But if that Rs 140 Crore market cap eventually becomes Rs 1.4 Lakh Crores over the next couple of decades, exiting early means missing out on the real magic.

If you had simply reinvested your dividends and stayed put you could have made 1500 times your money. That is the true power of long-term investing and letting your winners run. Even seasoned professionals make this mistake of exiting too early.

You might buy a massive 10% stake in a consumer finance company when its market cap is less than Rs 1000 Crores only to exit too early and watch it become a giant. You might successfully ride the first wave of a PSU and defense rally but completely miss the subsequent massive run-up in railway stocks.

The key is to study your misses and wealth destruction with the exact same passion that you study wealth creation. Ask yourself how you missed it and what fundamental signals you ignored when you hit the sell button. Realize that markets are much larger and can remain in a growth phase much longer than we intuitively think.

If you are not investing full-time and cannot dedicate extreme hard work and passion to tracking these businesses, you are better off allocating your capital to professional fund managers. Treat investing with the respect it deserves because it is the business of businesses.

Disclaimer: All information shared above are strictly for educational and informational purposes only. It should not be construed as financial or investment advice.
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