Hmmm... I too quit my job, ditched my condo, sold my fancy car, and hit the road. I don't regret it at all. I learned a ton about how to be a better version of myself, found a better way to live (half work and half play, instead of 5:2). I also found the love of my life on the road. But I miss my friends in santa cruz, i miss having a real home of my own. I miss stability. I miss the climbing gym. I miss "normal" sometimes. I'm sick of being careful about money. And I'm not saving any $ for retirement, which is kind of scary. Regrets? no. but it's not all pefect either.