Lesson Learned: Not Letting Winners Run on $MSFT

Anyone ever kick themselves for taking profit too early on a fundamentally strong stock? I'm talking about $MSFT a few years back. Bought it in late 2017 around the $80 mark, saw it push into the $100s by mid-2018. My initial plan was to hold for a significant move, maybe even a multi-year play given their cloud growth and enterprise solutions.

But then the market got a little choppy. I saw my profits sitting there, and the temptation to lock them in was strong. So, like an idiot, I sold out around $110, thinking I'd wait for a pullback to re-enter. Well, that pullback never really materialized in any meaningful way for a re-entry point I was comfortable with. It just kept grinding higher and higher, eventually splitting and then exploding.

Looking back, the mistake wasn't taking profit; it was ignoring the core thesis and getting distracted by short-term noise. The company's trajectory was clear. Had I just held, or at least scaled out partially instead of dumping the whole position, that would have been a significant multi-bagger. It's a constant reminder that sometimes the best trade is no trade, or just letting your winners compound, especially when the underlying fundamentals remain robust. Greed gets you into trouble, but fear can also make you miss out on massive opportunities.