Great thread. My story might not be helpful, but I'll toss it on the pile, because everybody loves a good FIRE story, right?
I was putting myself through junior college in the late 70's. I realized if I took a year off and worked, I could declare myself "emancipated" and thus be eligible for greater financial aid at a good university. I was working in retail part time, so I applied for a job with one of my vendors, based on my experience. I beat out a bunch of other candidates and a whole new world was opened up to me. It was a sales support job that included salary, benefits, travel and a company car. My friends were green with envy. Most people at NewCo were college graduates, but doing the job effectively was valued, so I did fine. The sales person I was teamed with was a single mom, maybe ten or twelve years older than me, returning to work after her husband had died of cancer, exacerbated by a misdiagnosis. She had a preschool child and was starting over. We got on well and she became kind of a life skills mentor/role model to me. I learned a ton from her. I loved the job, but was getting some pressure to join the sales team, which I did NOT want to do, because I planned to go back to college...
About six months into the job, we were at a National Meeting in Acapulco. One evening, our large group herded onto multiple charter buses en route to a fancy Awards Dinner. Ours was so over-air conditioned that all the windows were fogged and condensation was dripping down them. The bus drivers started passing each other on a winding road, playing chicken with oncoming traffic. I was scared shitless and freezing. I leaned forward, tucked my hands under my knees and...felt a lump. My mentor was sitting next to me, also trying to stay calm, so I mentioned it to her, kind of as a distraction. She freaked out, because that's how her husband's cancer had started. Thanks to her dire concern, I took it seriously...
Yup, it was cancer. The company was incredibly generous with me as I recovered, so I decided to stay at least until the five year mark out of sheer gratitude. I could finish college later, right? For now, I had new goals. I wanted financial security, I wanted to own my own home, and I absolutely could never, ever go without health insurance. My very rare cancer unfortunately, had a "propensity to recur", especially in the first five years. Plus, in the course of treatment, a heart problem had been discovered. Shit.
I went back to work and was eventually pushed into sales. I was good at it, but it didn't feed my soul. I felt trapped, because I needed medical insurance. I reluctantly decided to forgo the college dream, focus on financial freedom and retiring early, which was not a "thing" back then. I also promised myself I'd stop and smell as many roses as possible along the way, which I did.
~~~~~~~~~~
[Omitting many interesting-to-me life stories here; this is already too long.]
~~~~~~~~~~
Fast forward almost thirty years. I had accrued a growing 'stache and expensive property. I had traveled and adventured as much and as frugally as possible. Did I mention I lived in a HCOLA? And that I needed healthcare? And that "Obamacare" didn't yet exist? I was reasonably successful in sales, but no longer enjoyed the grind. I wanted out. In 2012, I decided I wanted OUT and determined to do so at the end of 90 working days, come hell or high water. I made a 90 link chain out of pink construction paper and festooned it around my home office. My vague plan was to rent out my house, buy an RV and travel my ass off, but I still needed healthcare. (Do you sense a theme here?)
ACA wouldn't come into being for two more long years, but health coverage for domestic partners was now a thing. I decided to explore that angle. I discussed it with one of my close single woman friends, who was in academia. She said she'd do it for me in a heartbeat, but her cousin was in HR and would know it wasn't real. Couple of days later, she was at my house when a contractor I'd previously used came by to give me quote to paint, in preparation for renting it out. My nosy friend asked him tons of questions about his day job. When he left, she said, "His company's benefits are way better than mine. He's a widower. There's your potential domestic partner." W-w-w-hat?
Next time the contractor was over, I broached the subject with him. I'd known him for a decade. I had done a significant favor for his family years ago and we'd kept very loosely in touch. I'd also referred him to several friends. I knew he was a good guy. I had worked with men most of my career and grew pretty adept at spotting the cheaters. I knew he wasn't one. I also knew he was recently widowed after 25 years of marriage to his high school sweetheart.
We had a funny conversation. Since this is already too long, the short version is that he agreed quickly, adding, "What you did was so important to my family that I'd even marry you on paper if it helps you out." What???? We decided to have dinner together a couple of days later to talk about it. At dinner, he explained that his healthcare premiums for his immediate family were 100% paid by his employer. I could get healthcare for zero cost! And, he had an RV! We kept talking. One dinner led to another and just like that, we realized were dating! We eloped a couple months later and I quit my job a few weeks after that. Lest anyone think it was a marriage of convenience, we've been happily married for nine years. We still sometimes joke that we can't believe it. Neither of us ever had a clue our lives would turn out this way.
So, after years of struggle, of scrimping and saving and kissing frogs in search of my prince, I finally found him. Sure, it sounds like a crazy fairy tale (and it is), but it turns out that getting married instantly blew us way past any "Magic Number". For [reasons], he kept working, but will be pulling the trigger in March. We are now richer than either of us ever thought possible and we are so excited to begin this new chapter together. Funny, we bought a new (to us) RV right before the pandemic started. We're looking forward to exploring the world soon. We had a nice practice run at last October's Moab Meetup.
To circle back to the original question, I always wanted to take a sabbatical and/or retire early. I "failed" because I didn't actually retire until I was 54, but it was completely worth the wait. Life is crazy, unpredictable, and wonderful.