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Personal Finance Topics / Retirement Investing
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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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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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