Since your question just arrived, I’m assuming you have until later in 2020 before you are forced to sell some of your stock that came through a corporate benefit. I could be snarky and say the best time to sell is “just before the market falls!” But that’s not nice — however true it is. There is absolutely no way to tell the “best” time to sell a stock.
However, I am going to give you a few bits of advice you did not ask for! First, meet with your CPA or a good financial planner to discuss the tax implications of this sale. If you exercise stock options and sell immediately you will have a short term gain — the highest tax rates. I’m not sure about how Restricted Stock units are taxed. Remember, anything you sell will add to this year’s income.
And that’s not your only issue. What are you doing about health insurance until you reach age 65 and qualify for Medicare?? Did you think about that before you took early retirement?
And don’t even think about taking Social Security before full retirement age! That’s almost a decade away!
I’m just going to assume you were “forced” into “early retirement” from your current company. Assuming you don’t have health issues, the most productive thing you can do is find another job — right now, while the economy is booming and employers are looking for talented people. Assuming you’re healthy, you can look forward to at least 30 more years of “retirement” –and perhaps many more than that.
Find a good financial planner to spell it all out for you. My suggestion is to start at www.Wealthramp.com — where you can find a fee-only planner who is a FIDUCIARY, promising to put your interest first!