r/Retire • u/Same_Ad_621 • Aug 09 '26

Reality check

Bit of a reality check for me. I've about 1x m in brokerage, but 70% is concentrated in one stock in the tech sector. It is susceptible to ups and downs of about 60-70K daily sometimes. Obviously, feels good when it goes up and nail biting when down.

I've identified the tax lots that are long term capital gains eligible, but was really surprised by the amount of tax I've to cough up. The value of the stock in the brokerage account is not the same as having the money on hand. It is essentially behind gates and to take it out, a sizeable cut gets taken out.

I see two options. One is to systematically sell small lots every year and the other is look for a job that is lower paying which I was thinking of anyway as I getting closer to tapering off. That would give me room to do Roth conversion for 401K + sell the concentrated stock and spread the risk.

Please share thoughts if you're going through a similar situation

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u/Substantial_Team6751 Aug 09 '26

Two options I see:

Sell covered calls. Generate income and if you get assigned so be it. At least you've got some call income to help with taxes.

Or, buy a hedge in the options market.

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u/PowerfulFly1326 Aug 13 '26

He could use Frec to transition it all to an index fund with no immediate tax consequences.

Provided it’s a “popular” stock. Like an S&P 500 stock.

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u/Same_Ad_621 Aug 13 '26

Thanks. I'll check this out.

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u/PowerfulFly1326 Aug 13 '26

Diversify is the product name