So my company stock has done really well, but past performance is not a bullet-proof predictor of future performance (in fact, due to mean reversion, it can actually predict underperformance), so I knew I would sleep much better at night if I sold my stock and invested it in a broad index fund instead. Even as an "insider trader" with reason to believe that the company will do well in the future, tying up a large chunk of your net worth in a single company is very risky compared to owning a well-diversified portfolio: in an economic downturn, or in the face of a company-specific disaster scenario, you could lose your job and see your equity value plummet at the same time. Double whammy!
Anyway, I just did the math. If I had kept my company stock instead of selling it, it would now be worth 1.5 million (pre-tax; about 932k post-tax). Instead, I sold it for 1.1 million (pre; about 711k post). So, I'd have 221k more net worth today — and possibly more in the future — but for me, I have been happy that I set a rational IPS and stuck to it. I've slept very well at night knowing I owned the total domestic and international markets, plus a decent chunk of fixed-income (bonds). Is 221k too high a price to pay for this peace of mind? Perhaps it is, as that would be enough to put me very close to FI territory, if it weren't for the darn taxes. But still, I am pretty happy with my decisions.
What's your price? How much potential upside are you prepared to leave on the table in exchange for peace?