Sometimes it feels like the tech industry eats people alive and spits them out.

I was going to suggest starting your own company until I saw that you already had! That sounds like a great new challenge -- and when you get bored with it, you can sell it and move on to something new.

I also don't think it's unusual to get bored in a couple years at a programming job. Most of the successful programmers I know stick with a place for a couple of years max and then move on to something new (in tech hubs - it's different in other places with fewer programming jobs).

Have you ever read any of Barbara Sher's stuff on 'Scanners'? You might find some of that stuff interesting. It made me feel better about getting bored with things.

You could probably get your GED and a degree in your sleep, so I don't see any reason not to go for it. Those pieces of paper do make a difference when it comes to scoring interviews 'cold.' It's nice insurance to have -- makes you feel better about taking time off to live off savings

You may be able to find a program that combines grad and undergrad, which would 'cover up' the timing of your degree. There was a guy in his 50s in my grad program who did that.

I really, really, really don't think anyone would notice the dates of your degrees in a negative way. You took some time off from school to work. There's nothing wrong with that at all. If you have your BA or BS, no one will question whether or not you have a HS diploma.

Can you take a few college courses without enrolling to see if it's something you want to do? Our state university system lets people take 4 courses without registering.