Feeling burned out

[chinaco]

Welcome.

Ditto the comments of some others.

If I were in your situation, I would exercise those options ASAP and lock-in the gain.

Too much risk holding options in a single company. Especially when you consider the ratio of other assets to those options.

I would talk to a tax accountant to determine if there is a legal way to minimize taxes.

[explanade]

Well some of my co-workers are looking at a selling to cover strategy, which would let them sell enough to cover the cost of the strike price but keep the remaining shares to hopefully appreciate.

Then they'd pay capital gains on any gains after the exercise date. They'd still have to pay ordinary income on gains when the options were exercised.