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Personal Finance Topics / Retirement Investing
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Author: suaspontemark 🐝  😊 😞
Number: of 1201 
Subject: Selling the oldest holding
Date: 05/04/26 9:29 AM
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No. of Recommendations: 9
CAT jumped 10% the other day, for [Insert Reasons Securities Jump].

I took a look; it was my oldest holding. And a 22 bagger. I sold it all, after a bit of nostalgia - I bought it when stocks were still traded in fractions. The proceeds will fund retirement for a good spell.

Time is your friend. Alternatively, if you don't like the look of the graph, zoom out. When I committed to that, it was a huge chunk of my net worth, and I fretted over it probably too much. Eventually I checked it quarterly. Then I thought about it less, and started checking net balances quarterly in accounts but not thinking about them too much outside of that.

When you wait long enough, eventually the dividends you realize from a security will greatly outpace your initial outlay. And the jump on a 10% day might be twice what you paid for it more than a quarter century ago, and you might sell all of it. It works, this LTBH thing.
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Author: onepoorguy 🐝  😊 😞
Number: of 1201 
Subject: Re: Selling the oldest holding
Date: 05/04/26 4:32 PM
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No. of Recommendations: 2
I tend not to sell. If I did any RSUs and ESPP, when I was employed, I would sell the newest shares that were long-term gainers (no short-term CG shares). Since retirement, I have sold one block of ESPP, and I did the OLDEST shares I had (roughly 60-bagger). Because I'm not receiving a pension (nor will I), and I'm not on SS, so our income right now is about as low as it will ever be. So, recognizing the oldest shares with the largest potential tax hit made sense. In fact, we didn't have a tax hit because our income was low enough last year. In 10 years when we both are receiving SS, that may not be the case.
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