What led you down that path?
I started a business immediately out of college. I don`t know if that counts for what you’re looking for. I employ myself, but I also employ a bunch of other people. So if you mean someone who works entirely on their own or with a partner or two it’s not me.
Like most people I spent years in college trying to decide what I would like to do. My biggest hang up was what sort environment I wanted to be at. The most common path for engineers and business students (I was both) at my school was to work for very large corporations. They’d recruit people on campus in September or October to start working in early to late summer of the next year, after graduating. Something about that repulsed me as it seemed obvious nobody hired for an entry level position 6-9 months before ever starting could be very essential to the company. So I started telling people I wanted to work someplace where I was really important to the company. I’d say, “I don`t have to run the place on day one; I’m realistic. I just want to know I really matter.” Then eventually I just said fuck it, I will run the place on day one.
Looking for people who saw what was going on around them, being forced to do stuff they object to, let’s call them “team building exercises” 
realizing they weren’t meant to be followers.
Fun and profit.
My first business was back in public school, hiring other kids to cut lawns. It was fun and profitable.
Over the years, I tried working in a variety of jobs, some good, some better.
Today, I run my own law firm, which is fun a profitable.
You found me. 
A visceral hatred of team-building exercises. 
ETA:
Well, shit, i didn’t notice your second post, which sort of ruins my little joke.
It never really was much of a question for me. I’ve generally been a “do you own thing” kind of guy and, luckily, I found a way to make it work. That said, my background is as a photojournalist, and people who go into that profession generally have a strong independent streak. I preferred freelancing to working on staff, and I’ve long since moved into weddings (reading the writing on the wall for editorial freelancers). It’s been a rewarding experience and I really don’t have any complaints about the lifestyle or the earnings. It’s pretty much my ideal life. The only real stress is the uncertainty: year after year, my business succeeds, but I never know what the next year will bring. It’s always possible nobody will call me or find me. That said, I suppose the same thing can be said being an employee of a company.
It’s just the way my business works - in Canada, all actors, singers, musicians and writers are self-employed. Once I realized that this was what I wanted to do, I didn’t have any kind of choice about being employed or self-employed.
It just worked out that way. By the time I was doing it, I realized that it was the thing that worked best with my lifestyle, activism/volunteering habits, etc. in that stage of my life.
Some of it was being tired of bad management, corporate stuffiness, dealing with the same people day in and day out - things like that.
It wasn’t until I’d put about a decade of it behind me that I gathered up the gumption to hang out my shingle.
I don’t mind being a follower if I have a good leader.
I worked my ass off for years and years, doing work that utilized a tiny portion of my brain, working inhuman hours that ruined my health, and making lots of money for people I despised.
Then one day I was in an art gallery. I looked at the crap hanging on the walls and thought “I could do better art than that” . . . then “the only difference between this artist and me is that he did it and I didn’t.”
I had always had artistic ability (both of my parents were artists), so from that day on, I really focused my skills and developed a style that is uniquely mine. There’s no turning back.
Oh, lots of reasons.
People in charge of hiring tend to not like hiring someone with a shady background, even if the person in question was never convicted of a felony. I also have a problem with authority figures who haven’t earned the right to tell me what to do. Then there’s the whole team-building exercise thing. Hated that the couple of times I had to do it. On top of that, I hate do the same thing day in and day out, so hiring out as a handyman lets me do something different every day.
Of course with the economy in the shape it’s in now, my business has dropped quite a bit, so now I’m looking for a regular job again.
Wow reading this thread just made me realize that I still have to deal with many of the drawbacks of being an employee. I’m an IT Project Manager and worked exclusively as an employee until this year. I had been laid off and there were very few permanent positions available so I started looking for contract work. The money is better, Mr.Moon’s job covers benefits and since the standard in this industry seems to be long term renewals it’s not as uncertain as I feared. However, I’m generally treated as an employee within the office which means team building, interviews and irritating managers. I do feel like I have more freedom to move on without the dreaded “job hopper” label if I’m unhappy.
Some say they built their business on faith. I built mine out of spite! That was my motivating force. I walked out of my last factory job at 42, and took what savings I had and built my own self-storage facility with me supplying about 99% of the labor. Fourteen years later, and almost 150 units later I keep them pretty much 100% occupied. I’m making almost 3X as much as my factory job, but now only working 12-20 hours a month instead of the 200 hours plus. I am very grateful how well everything turned out. I could keep expanding, but it’s time to go play now and do other things.
I started on a experimental aircraft project called a Van’s RV-4. That will keep me occupied for the next couple of years.
Recession? What recession? Every dog has his day.
I’m retired now, but I bounced around between working for others as an employee and working for others as an independent contractor.
Basically I kind of fell into the contractor phases. They’d typically start when someone had a specific task they needed done and it was better for both them and myself that I work as a contractor until the task was completed. Of course, that inevitably led to a second task that had to be done…
I should point out several things that made being a contractor much easier for me than it might be for other folks. My wife works, so there was always a steady income stream that we could rely on, and her health insurance covered me so we didn’t have to worry about that.
I got laid off in 2007 and couldn’t get hired - so I started hiring out as manual labor at construction sites, starting with just cleaning up messes. I also painted houses and mowed lawns, all just to keep some money coming in while I looked for a “real” job.
Then at tax time my accountant tells me I’m self-employed. What? When did that happen? I don’t remember hiring myself!
Anyhow, here I am three years later, still self-employed as a… well, whatever it is I do, construction/cleaning/painting/lawnmowing doesn’t seem to have a nice, neat label. It actually sucks - the pay is low, the work isn’t steady, and there are no benefits. I’d much rather be a wage slave at the moment but though I’m still looking no one around here is hiring. Or at least, not hiring me.
My husband and I are trying to put together a plan for a formal small business that both of us can work at that, we hope, will bring in more money than my current hodge-podge. He’s the real entrepreneur of the family, unfortunately, his health is crap. We’re hoping that healthy me will be able to cover for him on days when he can’t work. I’m hoping that it’s steadier money.
Same here. Except not in Canada.
I don’t think I’d have worked well as an employee anyway. I used to freelance for a couple of office-type places, in my day job, and I absolutely did not connect with the mentality. I didn’t understand why this woman in one place gave us freelancers a speech on corporate loyalty and how we should be giving the job 110% (???) because we cared about the company. I thought it would be taken for granted that I didn’t give the world’s tiniest damn about the company (why would I?); I was doing my best because, if I take something on, then I’m going to do it as well as I possibly can. I would have expected that kind of basic self-respect to be preferable to ‘company loyalty’ in any sane adult’s eyes, since it’s not dependent on how the company treats me - even if you do something crappy, as long as I don’t actually quit, I’m going to keep doing my best. (And yes, another freelancer and I said all this to the boss, in more or less those words - not bitchily, just explaining. She was utterly confused.)
I didn’t understand the corporate gibberish the bosses talked, or why the employees were expected to pretend it meant something. (‘The X family’?? Why on earth are you pretending this is a family? Do you think your employees believe that, or do you just want them to pretend they believe it? Either way, why??) I didn’t understand why the boss of another place would get hyper as hell when someone took a smoke break or left five minutes early, even when it was someone who he knew hadn’t taken a lunch break in months and was well ahead on his work. Surely you hire people whom you trust to get their jobs done like adults? Surely you hire people who’ll do their best because they believe in doing their best, rather than because they’re scared of getting in trouble like little kids?
I just didn’t get it. The places where I worked were actually pretty nice, mostly, and I enjoyed both the work and the people, but I thought the whole mentality - at least in the places I got a glimpse of - was very weird, infantilising, and in one case bordering on cultish and psychopathic.
So if you decided to have an old style touring actors company, with you as the owner and producer, and you specifically auditioned and hired 35 people [random number plucked from the air] to tour Canada producing Shakespeare plays, they would all be self employed even if it was you finding all the gigs and organizing and paying everybody?
Freaky
I was duped. A guy I knew had a successful business that was getting too big for just one guy. He was looking for a partner. I was happy as an employee of another business owner at the time. Guy kept contacting me until I gave in.
We formed a partnership (LLC) and then he came up with a reason to leave town. I was put into a position where I could either buy him out or lose what I had invested. I bought him out, even though the valuation (?) of the business was based on the two of us.
Fast forward a few years. The guy made some tax-related errors involving sale of the business to me that bit him in the ass. He wanted to reform our partnership. Business was going so well (I had paid off all my loans, etc) that I was able to tell him to fuck off, then block his phone number.
Usually, yes, but not always. Think of the actors as sub-contractors.