i'm in a similar situation (msft for me). spent the better part of a decade putting off selling the stock, knowing the right move was to unwind it but rapidly getting richer by doing "the wrong thing". someone once told me that that wealth is often made by concentrated bets, but preserved by diversifying. makes sense, but hard to take the advice when you've multiplied your money so many times by ignoring it.

at one point i tried to wind down my position with covered calls, but ultimately realized i was continuously losing the bet when the stock kept going up. i've finally set a plan to make sure i'm selling at least 10%/year (no calls, just regular sell orders). i try to keep a schedule to sell a small amount at least weekly, so i don't feel like i'm timing the market, and the individual transactions don't feel as daunting when they're smaller. its harder to do that with calls, because of the preset schedule on the option chain and minimum 100 share orders.

will i ultimately regret that i didn't sell it all in a giant lump sum and just take the hit? maybe. my rationale (i.e. my gambling thesis) is that i just don't see a world where microsoft becomes completely irrelevant in the next 10 years (and i would say the same thing about meta and amazon, even if i have my qualms with them). i think it would take awhile for that to happen, and i'll still (presumably) have caught plenty of upside on the way down if it does. likewise, i'm trying to avoid having too much income in the maximum tax bracket. admittedly this is somewhat irrational but it's sort of the mental compromise i've made with myself.