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While I will not be retiring in two years I will have to start selling assets in a few years to pay for college expenses, so I have thought about this too. I transferred the account intended for college expenses to folio[fn], along with my Roth IRA. I am dollar cost averaging in my monthly contributions, and plan to simply sell a percentage of the entire account to pay college expenses every year when the time comes, as if it were a mutual fund.

If I didn't have it there and had to pay a commission on every sale, this is what I would do. If it was time to sell a former gorilla candidate and invest the proceeds into the winner, I would sell the former candidate and spend it instead of reinvesting it. If that didn't cover what I needed, I would shave an equal percentage from several holdings--all of them if possible. It would prevent me from kicking myself because I sold the one that turned out to be the REALLY big gorilla when my crystal ball was on the blink.
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