I've worked in a LOT of the business. I spent many years absorbing the entire internet (or at least it seemed that way) on how to do basic stuff. I worked my way up to being really confident doing nearly anything - building engines, final drives, wiring harnesses... the only things I don't do are body work because I suck at it, transmissions because I've never tried, and I'm only a fair welder.
My first real job in the business was given to me by Wil Sakowski. It was a fantastic hot rod/custom shop in the true SoCal style. We didn't have a big name, but I promise you've seen some of my work, especially if you ever saw a ZZ Top album cover with a chopped and channeled Cadillac. I had no part in the initial design, but I did some suspension re-engineering on the rear. I'm sure any of you who collect Hot Wheels probably have a few of the cars that I co-created with my buddy over at Mattel. We would build the full-scale version of their flagship car every year for SEMA.
Wil moved that shop and I didn't follow. I turned down a position at Hollywood Hot Rods because Troy wanted me in the shop, but also wanted me to cover the office. After three interviews, I passed. I felt so baller. Turning down Troy Ladd's job offer. I ended up working at a massive dealership in the Valley north of L.A. They had about 40 techs and about 50 bays. They refused to hire me, so put on a Goodwrench shirt that I had bought years ago, showed up with my truck and toolbox, and unloaded it in an empty bay. I walked into the office and said that I needed a repair order. They gave one to me. R&R warranty transmission on a 2500 pickup. I knew how to fix it, but I knew nothing else. Where did we park the service cars? Where were the keys? Where was the bathroom? I worked the first week racking up repairs. That Friday was payday. Everyone lined up but I knew I would get my first check two weeks later. So I worked for three weeks with no pay racking up repairs. The next payday, I lined up for my paycheck and it wasn't there. (obviously). Service manager asked who hired me. I figured in a dealership like that there had to be someone named Tim, so I said "Tim." He said, "you mean Tom? Well, go see [insert name] and fill out your W4." No one ever knew. By the time any questions were asked, I had been there nearly a month and was doing well, so they just assumed I had been hired. I never met Tom.
I then moved to TX where I started as a wrench-turner for an independent shop. Cut my teeth doing timing belts, tranny R&Rs, engine changes, wheel bearings, etc. Did that for a while until they made me a service manager and eventually opened up a second shop that I ran. We turned that into a franchise of 13 shops all across TX until it became apparent that the owner's profits started going up his nose and into, um... professional girlfriends.
After that I ran a few transmission repair shops until I got out of the business altogether.
Too long of a story? Nutshell version. If you can find your way into a service writer/manager position after some time as a grease monkey at a repair shop, you will gain SO MUCH experience. Don't apply for a tech job, apply for a service writer position. List your experience as being heavier on the tech than the management. They'll hire you to be a tech, but know that you're looking to move up. If you apply to be a tech, you'll stay a tech for a long time. Once you're behind the desk in a polo, you'll have two things. Experience getting greasy with a ton of different cars, and the run of the shop. Depending on the shop, that's a beautiful thing. At my independent shop, I was the boss. I spent the day in sales, and at 5pm I suddenly had a million-dollar facility full of lifts, air compressors, acetylene torches, welders, diagnostic equipment, HVAC, and easy/safe disposal of fluids. I built a 383 for a Baja boat I picked up, had my 4L60E rebuilt at cost, and I even would go junkyard picking and put it through our steam parts washer to sell for a profit.
I started out spending a decade absorbing all I could from the internet, (what it could offer in 1996) local friends, other/wiser car folks, but the 7 years I spent as a service tech/manager taught me insane amounts of information about a massive range of cars. It has also informed me so much about buying used vehicles. Every time I see a 90s DSM for sale cheap, I remind myself of the weak bolt bosses around the terrible timing belt tensioners. Every time I see a cheap Audi R8 come up on Copart, I remind myself of the $1600 TCMs that like to fail every 20k and require custom ordering from Germany and it takes 16 weeks shipping and a transmission disassembly to install it... plus a $1200 reflash at the dealer. Every time I see a cheap AWD Explorer, I remember how many BW transfer cases I repaired because a tire was 5 psi low. Stuff like that.
I will echo what others have said.... Don't make your hobby into your profession. If you spend all day working on cars, the last thing you want to do is work on your own. I don't know your age or experience, but if you get into the business long enough to milk it for all the info you can absorb, it is a GREAT way to lean so much. If you told me at 49 that I had to go back to that business, I would rather declare bankruptcy. I'm past that. But if you aren't, milk the system. Use it as a university.
Notice I never used the term self-taught. I spent a decade learning off the backs of others more savvy than I. I'm not self-taught, I just read the "how to wrench for dummies" that friends, google, and shop manuals provided. I'm self-learned, thanks to the thousands of people in the world who knew more than I and were willing to share it.