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There are a lot of investment opportunities out there, and all but this one are not correlated to my paycheck.

I generally agree with this thinking. When both your current income and your retirement savings are tied to one company, you're taking on some extra risk. In theory, there is no company you will know better than your own, so the risk can be worthwhile. But I'd invest in my own company only if I would be comfortable investing if I didn't work there. It needs to stand on its own two feet as an investment.

I have the option of buying company stock in my 401k or discounted after-tax, and I do neither.

Just a counterpoint to this statement. Buying the stock at a discount doesn't mean you have to hold that stock. If it were me, I'd treat this like free money and be participating to the max allowed, even if I thought the stock was a lousy investment. You're guaranteed to purchase the stock at a discount to the current price, and you're also free to immediately sell it. So every quarter (these plans are typically on a quarterly cycle) you'll buy shares at less than the current market price and be able to sell them right away, pocketing the difference with little risk.

But each person has to do what's right for themselves. If it would keep you from sleeping at night, don't do it.

--Peter
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