Ask HN: Am I being penny wise and pound foolish?

Yep. I doubt a job that pays $25k will give you the kind of development you want. "Executive assistants" (secretaries) don't learn to be executives. Your salary is so low, no-one will care about your career path. Sorry.

It's great that you want to beef up your skills at Khan Academy, Udacity, etc. That will help you weather the bullshit of brick-and-mortar college. Ideally, you should also connect with other students (and even have a chat with staff) who are also interested in learning for its own sake - that's one redeeming feature of college.

Anyway. $30k of student debt (plus a year's lost salary at $25k) kind of sucks, but it's not serious debt given how much it will pay off. People borrow more for cars.

I don't mean to be obnoxious, but at the salary you are talking about you are better off trying to get a job as a janitor at the college. It usually comes with free tuition. Local college just had an ad out for janitorial help at 24k per year, comes with state benefits, including some form of tuition waivers. Full time though, so it may be hard to fit in your classes.

Get the degree, but keep the job. Find a way to work on the degree part time, or work at the job for a couple of years and then tell them you want to get a BS.

30k in debt may not seem a lot, but it will feel like that nagging weight at the bottom of your backpack that pulls you down a little. It'll impact your decisions on what car to buy (and how well you maintain it), where you live, whether or not you get married, kids, etc. I'm not saying don't borrow, but do it with your eyes open (which you seem to be). Work for a few years, save up some savings, find a school which will credit your existing education and allow you to focus on the courses you need for a BS/MS and not the silly side classes that all schools force on people to justify the other departments.

The associates degree might be an issue in the long run towards advancing your career unless you do something phenomenal that makes up for it. As others have said, get the BS at least. However, get the degree on a part-time basis slowly while on the job. Definitely check around to see what decent college would give you the most credits for the classes already taken. Make sure to look at the curriculum that you would take at those schools.

One famous person who did the part-time degree approach was U.S. Speaker of the House John Boehner.

Yes. Starting salary for programmer with a B.S degree is about $60-70K. Depending on region of the country. Go to senior college an get your degree.

Your story is shockingly similar to mine.

I did eventually go back to school, and my salary tripled as a result, but if you are fine making $25k then why worry about it?

If the reason you would care about money is to make yourself happy, then there's no reason to go to school if you'd be happier without a degree. If you want money to donate to charities etc., then it's a harder question.

It would help if you told us what country you live/work in. If it's USA/Canada or most countries in the EU, then as others have said, you could go be a janitor for more money. If you're living in China, Russia or a 'developing' country, then that's probably pretty good.