About two years ago I had a coworker that was getting out, going full-time real estate (he's happier now, good for him). He asked - if you left teaching, what would you do?
I didnt have a real answer for him, I like teaching - it's, basically, just telling stories.
So I'll start with that and now say a second part before answering the OP. My fiance has her own business in the downtown area of Winston Salem. She works hard, the hours really suck sometimes (does a lot of wedding, she's a florist), and the money isnt pouring in nor is it steady. It's improving every year, but, still, she's busting her butt to try to manage it all (get employees who are decent and pay them a decent wage to keep them there etc, while still paying her shop dues and home bills too). Doesnt look fun, honestly. She's the last one paid. First one in and out, last paid, most stress etc.
Now, for the original question. Is it right now with the amount of money I have in savings? It's not a ton, just at 5 digits, so cant do a ton with that. And, of course, there's the issue of paying my mortgage at the same time etc.
But ideas Ive had, that I'd be interested in doing:
-self-service car wash. Not the automated stuff, just the basic brick structures with a few bays and vacuums.
-small self-storage facility. Even places around here with no power, not climate controlled etc are almost a hundred bucks a month for a 12x12 approx. One unit at a hundred dollars aint a lot, but if you had twenty of those, well, it's a start.
-Pressure washing business. Freaking hard work, as almost all your work will be during hotter months, but could be a relatively low buy in.
-A project/creator space. Ive heard of these in bigger cities, but if you had a large area, just having various tools available to use for people, basically renting items out to people who dont have space to work. The more business you do/did the more you could buy and increase your appeal. And maybe even while running this business offer up various services for folks who need something done but question their own skills/use of the tools? I dont know man.
-Lastly, Id love to run a media blasting company and/or powder coating company. It'd keep me sort of involved with cars and motorcycles, but not so much that I dont enjoy the HOBBY anymore.
Last anecdote I'll tell you: My father, in the late 90s/early 00s, was quite popular motorcycle builder. Like, he had a bike featured on the front page of USA Today. He didnt want to be a motorcycle builder for a job, he's in the furniture business (still is, owns his own importing company), but he started a small shop on the side. My grandfather manned it during the day, and was a part owner, but it was basically my dad and his friend who worked on bikes after they got off their 40+ hour a week job. Then, for a vacation they'd do what they always did - go to bike rallys and stuff. But now it was, "Hey ____, can you look at my bike, _____ isnt right with it..." He couldnt just enjoy riding and the 'scene' (I guess that's what you'd call it), it had really become his job which he DIDNT want.