In 2009 I left my well-paying job at Google to start a startup. I wasn't terribly unhappy at Google - I just didn't want to spend my whole life there, so it see

In 2009 I left my well-paying job at Google to start a startup. I wasn't terribly unhappy at Google - I just didn't want to spend my whole life there, so it seemed like a good time to do something else. Over the next year and a half or so, that startup fizzled. Psychologically that point of failure felt pretty bad. But it seemed pretty clear that I would be able to come back on the job market in a fine situation. Employers seemed to consider a year working on a startup as either a neutral or a positive item on my resume. And I had certainly learned a lot more about many different things than I would have in a few more years at Google. Anyway, I felt like I had more fun working at the startup, and since my fizzled startup was actually able to pay me a bit I still had decent savings, so I did another startup. Investors thought the experience at the previous failed startup was a positive, and the experience from the first failed one really seemed like it was helpful to me too. For you, if you have a high paying job at a FANG company and had prestigious positions in other companies then you are a pretty competent person. You are going to be able to find a job that pays you well enough to live a good lifestyle, even if you take some time on a failed venture, and even if you move to a different part of the country. You don't need to be afraid of a negative outcome. You only have one life to live. Are you going to spend the rest of it in a well-paying job that you hate? Knowing that it might have worked out better if you had been willing to take a little risk? TLDR Do it!