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When (if) I should consider cashing in (selling) shares to realize capital gains?
In a perfect world of random stock returns (with a drift) there is no reason to "take profit" by exiting a position because there is no reason to think price appreciation will be followed by decline.   In our imperfect world, there are many rules of thumb that occasionally work but if any one of them works consistently over a long period of time, everyone starts to practice that rule and then it stops working.  Therefore, there are no such rules of thumb that work reliably and consistently over long periods of time and are expected to continue doing so.  Finding such a rule is and always has been a moving target. The rational, consistently sensible reasons to sell a stock are: These rules are very different from my interpretation of the "walk with your chips" behavior mentioned in your question.