My stock options have gone to basically zero twice in my career. It's OK. I knew going in they were gambles on companies I wasn't sure would take off, and I mad

My stock options have gone to basically zero twice in my career. It's OK. I knew going in they were gambles on companies I wasn't sure would take off, and I made sure I still had a decent salary from those companies. I also got a LOT out of those companies in experience. You don't have to buy options that are underwater, or that you're not sure will go back up. You might choose to buy some anyway for Reasons (in both my cases I did do modest purchases, and nothing has come of them), or you might decide to go put your money elsewhere. My advice to you: particularly if it's early in your career, don't put all your eggs in one basket, and don't have only one iron in the fire. Find other ways to squirrel money away. Diversify your holdings over time. Consider all the investment vehicles your company may offer: US companies I've worked for also offer ESPP, 401(k) contributions and matching, and RSUs (which unlike options are actual shares given to you), for example. Finally, go talk to a financial advisor if you haven't already and come up with a long-term plan that makes sense to you. That should give you some peace of mind!