Hyperborea
Thinks s/he gets paid by the post
I'm now in an unusual situation for me - I have vested stock options that are above water. Now, I've had vested stock options and above water stock options but never both conditions at the same time.
What I'm trying to figure out is how to decide when to sell. The two extremes are to sell now and get the money when the gettin' is good and at the opposite end is to ride them out for as long as possible and take a gamble. Current value of the vested options is about 50% of one year's expected retirement income and the total value (vested and still unvested) is about two year's retirement income at current prices.
These are non-qualified so there is no tax benefit to holding but there is the inherent leverage. At the current price of the stock a rise of 10% in the stock price improves my gain by about 35%. The company prospects are good and they are making money and doing well. Those all speak to holding on - at least for a while. The question is for how long?
I have ESPP too but there I do what I usually do and wait for the taxable holding period (~12-18 months) and then sell. So, I don't have too large an exposure to my company's stock - just a fixed amount that's in ESPP waiting to be sold (~50-75% of one year's expected retirement income). There is no company stock in my 401k.
What I'm trying to figure out is how to decide when to sell. The two extremes are to sell now and get the money when the gettin' is good and at the opposite end is to ride them out for as long as possible and take a gamble. Current value of the vested options is about 50% of one year's expected retirement income and the total value (vested and still unvested) is about two year's retirement income at current prices.
These are non-qualified so there is no tax benefit to holding but there is the inherent leverage. At the current price of the stock a rise of 10% in the stock price improves my gain by about 35%. The company prospects are good and they are making money and doing well. Those all speak to holding on - at least for a while. The question is for how long?
I have ESPP too but there I do what I usually do and wait for the taxable holding period (~12-18 months) and then sell. So, I don't have too large an exposure to my company's stock - just a fixed amount that's in ESPP waiting to be sold (~50-75% of one year's expected retirement income). There is no company stock in my 401k.