I remember back when I was 26. I had something like $5K in savings, and I wanted to spend more of my days snowboarding (basically work in the evenings and snowboard from 9-5).
I had a string of jobs in restaurants for years, most requiring mixed shifts. In my spare time, I was slowly building up a freelance writing clientele, but I didn't really feel comfortable enough to just go without a stable job for any extended period of time. That is, until a certain fateful job interview at the Bubba Gump Shrimp House (or whatever the hell it is) in Breckenridge Colorado.
The interviewer asked me which hours I would like to work. I told him I only wanted to work in the evenings so I could snowboard during the day.
He got really angry about it and treated me like some punk kid (probably with reason since there were a lot of punk kids trying to do the same). He told me my expectations were ridiculous.
At that point, I figured the interview was over. So I just casually said, "Okay, well this freelance writing thing I've been doing seems to be taking off, so I think I'll just keep doing that." I will never forget the puzzled look on that poor soul's face. Dude was speechless.
I ended up spending that winter doing exactly what I had set out to do. I went snowboarding nearly every day, and I worked on freelance writing projects at night. Most days, I only worked 2-3 hours. I ended up doing that for two more years, and I even took trips down to New Zealand in the summer to keep the good times rolling when we didn't have snow up north.
I eventually moved into higher paying jobs in software, but I try to remind myself of that experience every now and again. Back then, I was in a far weaker financial position than I'm in right now, but I had this sort of ballsy confidence that I could build a writing business out of a crowded snowboarding frat house, spending as little as a few hours a day on it.
My cushion is much bigger now, but none of that really matters because I have something no employer can take from me - the ability to spin up a business out of almost nothing. I've done it with iOS apps and recently software development tutoring. If I were ever to lose my high-paying work, I could easily start growing those businesses without skipping a beat. There's really nothing to fear at all.
So while I certainly love the warm and secure feeling that FU money gives me, I kind of think FU confidence is better. Sometimes I need to do a better job of channeling my younger self. I kind of had it together back then, albeit in a strange and offbeat lazy snowboarder kind of way.