I may not be understanding your question but I generally have advised my wife to sell most of them as they vest. Having all of your compensation in one company

I may not be understanding your question but I generally have advised my wife to sell most of them as they vest. Having all of your compensation in one company (salary as well as thousands of dollars in stock) is too undiversified in my opinion. They are also much less liquid then you'd think as there are often long blackout periods with short windows to sell so it's quite tough to time the market.