Started my own web design and internet marketing shop, which proved to be much harder than I thought because I didn't know shit about running a business. Caught a break with a startup building out their website and web assets and doing marketing. Marketing director got fired, I filled that role and got a raise.
Left that company after two years to co-found a startup. Raised a little money. Tought myself product design and front-end.
Startup was unsuccessful, but I used the skills I learned to land a gig at MIT doing product design and front-end dev. Did that for a while. Jumped from 40k to almost 100k.
Left MIT to lead product at a vc backed startup making 6 figures with a good bit of equity. That's where I am today.
Tomorrow, who knows...