I think you have to not only look at your net worth, but your annual salary. There is no stock answer here, but in general if you could not stop working for se

I think you have to not only look at your net worth, but your annual salary. There is no stock answer here, but in general if you could not stop working for several years, and your equity is several multiples of you annual salary maybe you should consider selling some. Another way to look at it is what is your goal for stock options in terms of your salary. Are you looking to double it? Quadruple it? It's easier to make a decision if you have a specific financial goal for your grants as opposed to something vague like "enough to retire", or something like that. In terms of financial adviser my advice would be never. At the very least learn as much as you can on your own first. This is a short (15 pages or so) pdf that can go over the basic of saving for retirement with some suggested reading. https://www.etf.com/docs/IfYouCan.pdf https://www.etf.com/docs/IfYouCan.pdf If after you've done some reading and you have some specific investment you are interested in, maybe it makes some sense. It's not crazy to hold stock, as long as the company has a good business and management and you think it's prospects are good. But it's not an all or nothing choice. What is crazy is to hold onto stock if you can't afford to wait out a downturn in the stock market, which can be many years.