Reverse DCA on Employer Stock

[leevs11]

Ok I'm having a tough time deciding this one. I have some employer stock options expiring about 1 month from now.

Should I divide the # of shares by 30 and sell some every day, or wait until the very last day?

The price sucks, so there's always hope that it goes higher, but wanted to get some thoughts.

[reeshau]

Unless the company is really volatile, that seems like a whole lot of action for not a lot of gain.  Part of the magic of DCA is not paying attention to the pricing changes in between, because that's not on your pace.  You are erasing that with daily sales.

How often do you get a paycheck?  Sell on payday, and then even if it was down that day, well, you just got paid!  You also have a non-market trigger to do it, instead of shadow market-timing.  Then, just decide how many paydays you want to split over.

[leevs11]

Unless the company is really volatile, that seems like a whole lot of action for not a lot of gain.  Part of the magic of DCA is not paying attention to the pricing changes in between, because that's not on your pace.  You are erasing that with daily sales.

How often do you get a paycheck?  Sell on payday, and then even if it was down that day, well, you just got paid!  You also have a non-market trigger to do it, instead of shadow market-timing.  Then, just decide how many paydays you want to split over.

This is kind of a one time thing. This is from a former employer. The stock is semi volatile, but very very beaten down over the past couple of years. I don't expect it to go up or down that drastically from here and it's not life changing money either way. I have 28 business days to sell it all or lose it.

[reeshau]

Well, just do it immediately, then.  Get closure from that chapter of your life, and this decision that hangs over you enough that you asked for a second opinion about it.  Or, tie it to some non-market thing: 1/4 every Wednesday.  Of half every other Friday.  Not too often, and not something that keeps you thinking about the price.

One other factor: it's earnings season.  Will they report earnings in the next 28 days?  It's of course your call, but you might want to finish before then, or sell 1/2  before and 1/2 after.

[leevs11]

Well, just do it immediately, then.  Get closure from that chapter of your life, and this decision that hangs over you enough that you asked for a second opinion about it.  Or, tie it to some non-market thing: 1/4 every Wednesday.  Of half every other Friday.  Not too often, and not something that keeps you thinking about the price.

One other factor: it's earnings season.  Will they report earnings in the next 28 days?  It's of course your call, but you might want to finish before then, or sell 1/2  before and 1/2 after.

I've been sitting on this damn thing for two years now. I'm ready to close this chapter.

Earnings is next Thursday. I think that's why I'm debating it so much.

[reeshau]

Sell them, and delete all tracking of the ticker before earnings.  It's best for you to move on--it's not really a DCA.

Don't give this former employer any more free rent inside your head.

[Freedomin5]

It seems to me you’re trying to time the market. Just sell all of it now and move on. It’s better than losing all of it due to analysis paralysis.