"Successful" has a different meaning depending on your title. I work for a successful startup and all the c-levels are happy, but as developer #1 I am very unhappy. The goal was acquisition. We developers did our job: we iterated on several products until one of them struck gold and is minting money. We are ready to move on. The founders are enjoying the success and have put less priority on acquisition. As a "stay-up" we are now in the growth phase: more middle-tier, more process, more meetings, more politics, more hiring, more distractions, etc. Due to our success, I can no longer afford the taxes on exercising my options. I'm completely locked up with golden handcuffs. I want to leave, but if I do and they sell in the next couple of years I don't think I could handle it. I feel stuck and it's starting to affect my mental health.