Yes, a number of times over.

As for how I got there, a lot of it (and this is a largely unpopular view in some parts) was rather pre-determined. Born into an upper-class family, went to a private high school that sent nearly 50% to Ivy League schools, and graduated from a top school in '04. I studied computer science, but had little intention to pursue it and went to Wall Street.

Stayed on Wall Street until '09 and was worth slightly under a million when I left. I went from an investment bank to a hedge fund that in the crisis period did well enough, relatively, to still pay good bonuses. I had not invested any of my net worth, partly due to working 80-100 hours a week, and put a great deal in the market at the end of '09, which has obviously done well.

In '09 I was miserable, or rather more miserable than normal, and a friend from college convinced me to come to SV to what is now one of the largest companies in the world (it was reasonably large then too). Did well, working half the hours and ending up making more per year than at the hedge fund, and recently "retired".

Given your question, and your username likely denoting you're 25 or 26 years old, here's the truth: I've been miserable for most of my working life. My happiest days always revolved around my last day at each job. I didn't enjoy finance, but was good at it, and the same is true for the time I spent in SV. I've always been jealous of those that, for whatever reason, wholly engross themselves in a given field and are content with that. Following your passion may well be bad advice, but do not assume that a passion naturally develops out of one's work. Most of the time that "passion" that some, especially in finance, develop is simply a coping mechanism to justify the long hours and unnecessary stress of the job. I saw the same thing in SV, especially among the PMs that became increasingly detached from day-to-day development with seniority.

A million dollars in the bank will not make you happy and doing something you desperately do not enjoy for a million dollars, even if it can come in only 5-10 years, will not evaporate the bitterness you have towards yourself for wasting away years of your life in pursuit of that. Money, above a certain amount, loses it's context beyond being a measuring stick used against your colleagues and friends. I could have stopped working years ago. I wish I did. What you define to be a "certain amount" is an entirely personal decision predicated on a lifestyle that makes you contented.

I sometimes get asked for advice, often from people who are in their early 20s, now that I'm retired. My "advice" is that I wish I had found something that I would enjoy doing well into later life, whether I needed to do so financially or not. Spending your youth focusing on an upward trajectory of wealth, despite disliking your work, is a waste of a life; especially for those who come from privileged backgrounds like my own. However, spending your youth bouncing around a number of different jobs until you find something you actually like (even if it's not a passion, per se) is not a waste. I always end my little advice diatribe by noting that when older-folks say "money doesn't make you happy" it's largely pointless. I didn't believe them years ago, I wouldn't expect others to. It's one of those lessons that is only truly understood when wealth is accumulated; one of those lessons that is only truly understood when it's often too late.