[cvolzer3]

Figure out what your tax situation will be before selling. Short-term capital gains are taxed at your ordinary income tax bracket whereas long-term capital gains are taxed no higher than 20%.

If they'll be taxed at the short-term level, wait one year until they turn into long-term capital gains. You'll be saved from paying thousands in taxes.

[kspaans]

Disagree: you are avoiding taking a gain (assuming the stock grants are below the market value of the stock) in order to avoid taxes (but you will still GAIN money, even after taxes), in exchange for risking that the stock will decline in value.

It all depends on your risk tolerance of course, but avoiding selling at a gain RIGHT NOW in order to avoid taxes is not a good reason.

[smileysteve]

This.

If you won't need the money immediately; and the company prospects look mediocre to good; keep for a year. Then re-balance your portfolio.