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Too much in company stock
Hi all,

About 90% of my portfolio is actually in my company stock.  I've been liquidating about $20k a year of it, but between the stock portion of my bonus and the employee stock purchase plan, it accumulates faster than that.  Having most of my eggs in one basket means I have a lot of risk, although today aside it's done well for me.  Would you recommend I bite the bullet and sell most of my company stock and take the tax hit, then diversify?  Or simply ramp up my annual selling to maybe $50k or even higher until things even out?
I do think you need to diversify. How you do it is up to you, just be sure to do it.
In reality you have more than 90% in that one company, since it's 90% of your portfolio + probably the majority of your income. If the company gets in trouble then you may lose your job and your portfolio will get wiped out. That's not a good position to be in.

So indeed: Diversify.
You should absolutely diversify. I am adverse to paying taxes before necessary so I would lean to ramping up the selling of the stock to $50k or so a year instead of doing it all in one year and paying all the taxes. Though if you think that the stock is about to tank, sell and take the tax hit to preserve the portfolio.
No I think we're doing well, so I'll ramp up to $50k+.
Definitely diversify at a rapid clip. Too many unhappy endings start like this.

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