I broke my golden handcuffs to join WePay, a fast growing start-up in Palo Alto. I was at my prior company for 10+ years, had lots of unvested stock and guaranteed bonuses...and I was still generally happy. However, I just knew that WePay's culture and growth was pretty awesome and I couldn't pass that up. The way I got over it was that I just had to say to myself was that it was almost like I was going back to school - in this case, getting my BA in start-ups and that the stock I was giving up would be like tuition, an investment. I haven't regretted my decision...and it only takes the handcuffs to be broken once for you to know it can be done again!
totally! I think the analogy of going back to school is a great one and is the same rationale that I used when I left my job. 10+ years is a good long time so you could at least enjoy the benefits for a while before joining your startup :-)
well written, I can totally relate, esp the part about company culture