From my own experience:

One approach is to try software in academia. Look for departments that need web developers, and once there see about branching out into other areas (they often like folks who are willing to learn new things that can be applied in their domain).

In addition to the ability to branch out, you'll likely have the opportunity as FT staff to pursue a degree at reduced tuition (depending on the university/college).

It's often the case that you take an income hit in academia (which is often a reason they're willing to hire anyone with relevant experience), but the learning experience can be beneficial.

Of course, I could be generalizing my experience.

Just a thought.