Should I get a Degree?? (IT)

Keep going to school. It's good for your brain and your bank account.

Although you don't elaborate on exactly what your "record" is, nor do you need to, the fact that it MAY affect your job choices in the future may have you re-think your overall direction. IT is not a bad gig if you are truly good and exceptional at it, but the fact is there are may "dime a dozen" mediocre IT "specialists" around. Having a degree is not, per se, what makes you exceptional in the field. Indeed, it is a perfect example of the classic "education vs experience" issue.

Therefore you may want to concentrate on something that will allow you to excel working for yourself rather than as part of a corporate entity that is into minutely investigating your background. You've a lot more freedom that way, anyway. If you could develop a specific expertise that allowed you to hire yourself out as a fairly high-paid consultant, as opposed to retail, for example, you might be ahead in more ways than one. Over time the "record" issue will hopefully fade into the background, especially as you become known for your expertise.

This is going to take some serious and frank self-assessment on your part. Do you have what it takes? Becoming an expert--a REAL expert--in a field is not just a matter of philosophical desire. You have to be literally smart enough AND obsessed enough to become that expert, not just pretend you are. I am not dissing a formal education at all; I'm a proponent of it, but that alone is not going to get you where you want to be.

I'll say this OP. Get a degree if you need one but never just to want one. Degrees are a dime a dozen and IT degrees go 2 for 1.

If you can articulate what you generally want to do and why a degree will help? Go for it. If its just to 'be taught' how to do it? Don't waste the time and money.

YouTube has all the material and more to learn IT and certifications mean more to people I know in the field than Associates degrees. A degree can be a participation award at that level. Cert testing requires a bit more than friendly instructors with self interest to never fail people.

Just my take as a current student just passing through my AS requirements, headed to Masters.