The question depends on how badly you depend on the money from the sales, and how much taxes you want to pay for the sales, and what you would do with the money...
If you are unsure, there are 2 strategies I've employed that I found useful.
- the 50% rule: sell 50% now, hold on to 50%, and sell 50% every +-20% gain or loss from that point on.
So for example, if you start out with 10000 shares, sell 5000... Then if the price goes up or down another 20%, sell another 50% (2500 shares)...
This what I call the half glass full/empty approach... If you're a positive guy, it's the half glass full viewpoint... You lock in some gain now.. In case the stock goes down, you aren't losing as much, and if it goes up, you still have 1/2 invested... Or if you're a negative kind of guy, it's the half glass empty viewpoint in which, when it goes down, you should have sold the entire thing and when it goes up, you should have kept it all.... (Don't be the half empty kind of guy, you'll never be happy)... Given the choices, i'd rather have less of a profit by selling part of it early than holding on completely and risking a capital loss. Plus from a tax planning perspective, you don't want to do a huge lump sell all at once, otherwise it could throw you into a much larger tax bracket, if you aren't there already.
- Selling covered calls.... You can use this approach, if the stock price really doesn't move that much (IE it's a dead stick).....The idea is the following...Sell slightly out of money covered call that expires 2-3 months out... Then there's a high probability that the call option will expire worthless, allowing you to keep the option premium...
For example: right now intel stock is at $36.97/share......
1 contract call option for intel at $37/share that expires Feb 17,2017 costs the buyer $1.23 per share
(1 contract = right to buy 100 shares at $37, and the cost of that contract is $123 for 100 shares)...
So let's say you're not sure if you want to sell 1000 shares of intel stock or not and you don't mind waiting until feb. 2017 to make that decision. Instead of selling the shares now, you could sell 10 contracts of call options of intel at $37/share that expires in Feb 17,2017. You will give some guy/gal the right to buy your 1000 shares of intel stock at $37 up to February 2017..... In return, they pay your upfront $1.23 x $1000 or $1,230 for that option contract. That money goes right into your brokerage account immediately....
Now let's consider what can happen...
- In scenario 1, Intel stock stays down to anything less than $37/share by Feb 17,2017. Well, guess what, the guy that bought those option contracts just paid you $1230 for a worthless contract. Because that option is useless. If the market price of the stock is less than $37/share, he's not going to "exercise" that contract you gave to him, because he could buy the shares lower than $37/share on the free market....
You still own that 1000 shares, and you get to keep his $1230... And you're better off than if you just held onto the stock, because although the share price did go down, you also earned $1230 from the option contract your wrote, versus if you didn't.
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In scenario 2, the stock price goes up between $37-$38.23.. In this case, you make a little money, because while the person might chose to exercise his/her options, and you have to sell your stock, you got to kep the $1.23/share he paid you up front.
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In scenario 3, the stock price shoots up above $38.23....Well, in this case, you end up selling the stock less than what you could have sold it if you just held on even with the option contract. But you also have to consider (a) you were planning to sell right away anyway when the stock price was $37/share, so if you had done that anyway, whatever gain in the stock price afterwards wouldn't have been yours anyway since you already sold... and (b) you can't always time the market and know exactly when to sell at the highest point of the stock price....
In fact, the truth is for a stock that isn't that volatile and doesn't move that much month to month (such as intel) most out-of-money call options usually expire worthless. Keep in mind that option price also steadily declines in price the closer it gets to the expiration date if it remains out of money...
So you could chain and ladder them up month after month, writing covered calls every 2 months, collecting $1-2/share every two month as your covered calls expire worthless most of the time....Keeping $1/share each month for say 7-8 month out of the year: $8/year per share...
That's a pretty nice return for shares that don't move....(You do want to avoid months that could subject the share price to increased volatility...Specifically the month where intel releases their earnings)....
Obviously, you don't want to do this for a stock that has a lot of volatility like Amazon or facebook...And you want to keep an eye out for things that would make your "boring/low volatile companies suddenly volatile"... A good example of such a change of event would be like Chevron/Texaco, which was a boring stock until the price of oil went haywire. Anyway, you're an engineer. You should be able to figure what I'm saying out. But this is a decent strategy for stocks that don't really move that you don't really care if you hold on to or not.
The nice part is that since you aren't an employee anymore, you can totally play this game... Employees are bound to company policies regarding taking positions in derivatives of the company stock. Although taking derivative positions in company stock while being an employee is in itself not in violation of SEC laws for most employees, most companies adopt a COMPANY policy that prohibits current employees from buying/selling derivatives of the company stock, to avoid the entire issue that a big windfall from a derivative position might be perceived as insider trading by the SEC (IE although you were just lucky and didn't actually have any insider information, because you are an employee of the company, guilt by association..) So that's why most companies have policies that tell employees "don't do this why you are an employee".
Anyway my 2 cents...