There is something to be said about having "unordinary" experiences - it cuts you off from your peer group. My part-time freelancing through college meant that I was often too busy to do the things college kids do - party, join bands, etc.
Later, when I started freelancing full-time, my friends would talk about their bosses, applying for jobs, building up careers, etc. and I would just nod my head and attempt to understand but I couldn't. I've never had bosses - or even bad clients - and my idea of career has basically evolved into a series of gradually better/bigger gigs and projects.
I'm very independent person and can get by perfectly fine being completely alone. But I imagine that someone more extroverted and social than me would have felt a little too alienated living a life so different than their peer group.
When the pandemic struck earlier this year, a couple of my key clients dropped their budgets or held off on decision making. So I took that time as a "break". This devolved into eating too much, working out too little, and sleeping at odd hours - all great stuff for a week or two, but extremely grating after a month.
It's a romantic idea - a life without boundaries or bosses - but it's not something everyone is cut out for, nor is it something I would recommend everyone to follow.