Absofreakinglutely. I mean, my experience isn’t rosy like yours, since you ask: my regret is threefold.<p>First, I regret being naive. I grew up with the idealistic notion that if you are loyal to a business, they will be loyal to you. Reality: businesses actually ran like this are nearly extinct. Either way, when it comes to money, you can’t really trust people in a business arrangement to look out for you. Also, as I am now over-the-hill, I’m finding that someone with a long tenure and experience at one place is a liability. Bean counters want to replace you with someone cheaper and more expendable. Younger employees think you should retire and get out of their way (buddy, god willing I still have several decades to go and I’m not even sure <i>I</i> will be able to retire). Prospective hires think you have years of baggage and bad habits (which is likely true).<p>Second, I regret sacrificing the prime of my health and time eating shit at places I didn’t like for extravagant promises of equity. Equity is good and worth working for, but only if it’s worth the price you must pay <i>today</i>. Others may disagree, but I have found it’s not worth living in hell for the next 3-10 years even if that could potentially net me millions. And of course, there are no guarantees. The world could end, I could die any moment, or the company could go tits-up. My first startup experience netted me only $2000 for 12 years and a lifetime of regret… particularly over preferring to keep working rather than spending time with my father who later died.<p>Third and finally, I regret surrendering to my poor self esteem. I’m a college drop out, a nobody from a nobody town, working at small to mid sized businesses, and I think I’m merely ok at what I do. No one in their right mind could or should hire me. The job I recently left paid a very good salary, full remote, I had 10 years of seniority, I had lots of respect and could throw my weight around, all I had to put up with was incompetence and nightmarish stress. Since I have no self esteem, I felt I deserved that trade. It’s been eight months since I left, and I’m struggling to rebuild my confidence and control my anxiety.