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2008 Financial Resolution #2: Stop Buying Great Deals by Chief Family Officer is an great financial resolution. It reminded me of the ...

Saturday, August 15, 2026

Selling a Stock is a Difficult Decision for Me

I don't have a good methodology for deciding when to sell a stock. I usually base the decision on vibes or locking in a certain percentage of gains.  Unfortunately, this approach sometimes causes me to miss out on big gains as described in Panic Selling Winners Reduced My Investment Returns.  I tend to sell my winners, for small gains, especially after they have dipped significantly.

My spouse tends to ignore the volatility and just hodl.  As a result, she has up to 1800% gains on GOOGL which she has held since 2013.    On the other hand, I probably sold at 20 to 30% gains and never bought back in.  The difference is she held through all the dips instead of panicking and selling later.

That's what is difficult for me, holding after a big dip.  I have had some stocks go up 500-1000% which then go down  50% or more and never rise again.  Psychologically, I am afraid that will happen with any stock that rises and then dips.  So I settle for locking in profits at much lower gains.

I've only kept one profitable stock long term, stock from the company I worked for and retired from.  That stock is in my profit sharing retirement account, which was contributed 100% by the company.   I've held it partly because of NUA tax benefits, partly because of inertia of transferring the shares, and partly because it is a good company.  The shares are up 2700%.   Woohoo.

If only I was able to do that reproduce by not selling and hodling stocks like AAPL, GOOGL and AMZN.  Ah, hindsight is 20/20.

For more on Reflections and Musings, check back every  Saturday for a new segment.

This is not financial, stock selling, nor investment advice. Please consult a professional advisor.

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