As someone who witnessed several close friends get massacred by the end of year tax traps during the Internet bubble burst, hear me out.If you make any dramatic move prior to the end of the year, and lock in any profits, for the love of god please calculate the tax liability then and there, and put the money to pay those taxes aside in a safe place.Here is how my best friend f'd up. We worked at Sun. He had ESOP shares that he sold when he thought the market was peaked , late in the year. Early the next year, Sun dipped, he took the entirety of his 'winnings' and put it all back into Sun. Then the bubble burst, Sun stock plummeted, but he owed tax on the prior years enormous profit. He waited and waited as the April 15th deadline approached, hoping Sun would recover, it didn't, it actually got noticeably worse as tax day approached. My friend had to sell very low, to pay his tax bill, and was still $ 200K short!. It took him many years to recover.
Submitted December 24, 2020 at 07:56AM
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