Under normal circumstances, I would leave and find a place that aligns with the lifestyle I want to lead however this company has offered me a generous options package with an impending IPO in the next 2 years.
On one hand, I feel like it would be stupid to leave the company. On the other hand, I know I will be unhappy for the next two years.
What would you do?
An IPO payout could mean having freedom about what to do in the future, but it could also be worth $0 (certainly the mode of the distribution if not the median.) For many it turns out to be between the down payment for a car or a house -- not life changing.
A likely outcome for someone like yourself is that you keep working at a job you hate, get no payout, get another job under the same terms and after doing it five times you get a payout, put the money into your own money as founder and repeat the same mistakes as your current boss because you spent so much time immersed in that culture.
* Why would you join a startup? Wealth? Opportunity? Or some deep meanings.
* Which stage is it? The earlier it is, the worsen a company is managed. In your case, a late stage company still in a turmoil is a huge question mark.
* For startups, it's always better with showcase than a promise. If I were you, I would take a reference that matched to the first bullet.