became 'supervisor,' of sorts, and enjoyed it very much; got into substance of the work.

to do my job, but I don't have anyone on my ass giving me orders.

I drive for a blood center but I'm at remote site. We just have the one bus and one mobile crew there. I show up at the buttcrack of dawn and get everything ready, know where to go, how to set up and we do the blood drive. It can be weeks in between my actually getting any real direction from a supervisor. i stay out of trouble and they leave me alone.

for the last 11 years, i don't even think i'm capable of having a boss anymore

My husband works his ass off (too much to go into, but 6 days a week with a "boss", and 2 days a week "self-employed). He HATES his job, yet says over and over how worth it is to know that his family (me, 1 child, his, from a previous marriage, and 3 more together) has everything they need, and we are able to prepare for our senior years. We are not rich, though we make well above the median household income here in FL. My husband's side job is really more of a hobby, no way could he bring in enough for us to live minimally. We hope, one day, that we can live on that side job, but hubby says how much stress it would be to see us all go without.

So as much as he HATES his breadwinning job, he realizes, that for our needs, trying to "get by" just would bring him even more stress than working a job he hates. For him, at least when he comes home, he is coming home to a happy family. He grins most days walking in. No worries about bills, medical, braces, etc. But he is the type to be able to leave job pressures at work. When he is home, HE IS HOME! This man has no blood pressure, I swear. I wouldn't be the same way if the roles were reversed.

This is not a judgement on others who do it differently. Which is why I said it "depends". For other households, doing what you love and just getting by is the better option in the end. It is sad that is comes to that. I wonder how many would do what they love if there was universal healthcare and much more affordable/free higher education for their children? We have other circumstances. I am deaf, and finding it really hard to find a job after 6 years as a stay-at-home-mom. If I didn't worry about finding a job myself, maybe my husband could quit his crappy, but very well paying (we are not complaining!) job.

...I've left jobs before because the management was a pain. Actually, most of the jobs I've had I left for that reason, but my current one is fine. I've thought about self-employment often enough, but I'm realistic about the stress and headaches involved.

Now it comes down to - I'd rather make a decent wage and have reasonable hours than make more money and have less time. If I were my own boss, it'd be hustling every day to keep things going, constant paperwork, taxes and stuff I don't know how to do - now my boss does that part.

After being self-employed now for a while, I don't think that I could go back to working under anyone else again.

Last boss was a toxic racist scumbag. Not a good guy to work for. If it was any decent normal human boss, that would probably be better.

After 4 p.m. on Friday, having a boss goes out the window for me. I give my boss nary a thought on weekends. Always been that way except for the time I spent as a Realtor, which was in actuality a 24/7 kind of job and I was essentially my own boss. I saw no benefit from making money if I didn't have time to spend it.

There is no sense in working hard if you can't enjoy the fruits of your labor. Call me a fruititarian.

and I have chosen to go it on my own.

I cannot work for anyone else any more... I just can't deal with the idiocy that entails.

My husband and I are both self employed. I run a small horse farm and he does construction remodeling work. We have clients and they can be as tough as any boss. There is always a boss. No matter what you do, you generally have to get paid by SOMEBODY. And if they are paying you, you have to keep them content with your work.

or require a regular schedule. I trade futures from home. Steep and expensive learning curve but completely free with regards to work.

I'm frankly tired of struggling every day

I was just telling my daughter a little while ago that we were going to make it til the end of the month....and then it starts all over again. I am getting so TIRED of every month being a struggle just to make it to the next month so that we can struggle to make it to the next month. I want a vacation. I want to be able to shop ONCE and not compare prices or stand frozen in a store because I can't decide which thing we need the most...and worry that if I guess wrong, it is going to screw us up. I want a new sofa cause the dog ate ours when we stupidly left him in the house all day. I want to make a frivolous purchase. I want to be able to sleep at night. I want to go to the dentist.

*sigh*

The difference between a good boss and a bad boss is LARGER than the difference between "well off" and "getting by", by far.

A good boss keeps you busy with what you're best at and deflects irrelevancies before you have to disrupt your productivity for them. A bad boss tortures you, molests you, violates your personal boundaries consistently, and disrupts any human interaction you attempt to have on the job site.

The worst case is working for yourself, having to be the bad boss, and just getting by.

Though I agree with many that think their are grey areas in the OP's question; and at the risk of hijacking it, I truly believe it's more a matter a matter of doing what you like while "getting by" vs doing what you dislike for more money.

In my formative years, I had this discussion many times with my friends, and tragically ( to me ) all too many chose the latter. In my late teens I had some serious head-butting with my father over the same issue. He was a wokohaulic type that had to be the biggest of big shots in every endeavor he was in. I wanted to make a modest living doing what I liked. We had some serious screaming matches then. He's come to terms since then. In fact, thanks to my decision, I put a human face on a group he always detested: Well paid union ( gasp ) blue-collar employees.

as long as we're talking about fantasies... I figured I'd break your rules.

Punish me... as best you can... boss.

(hehe... though your inclusion of "insurance" as a "necessity" already gives you away as being clueless about "getting by".... I haven't had insurance for over a decade...)

I used to work freelance in the film industry.

I had health insurance through the Union.

I moved to Texas to get out of L.A. (not out of the film industry.)

Texas is a "right to work" state. I lost my Union health benefits because non-Union work prevails here.

I got out of the film industry because non-Union work doesn't pay shit.

I took a slave wage job to have health care.

And here I am, stuck.

I like my free time.