Take a software job that requires you to change roles from those you know, or take the lead, adding responsibility in one or more ways:

- technical expertise (esp a subject new to you)

- project time management

- project cost estimating

- writing up and publishing your work

- coordinating resources for new contracts

- writing proposals for new projects

- speaking publicly in promotion of what you will do or in explanation of what you have done

- exploring / growing a new business area

There are many ways in software to expand your range.

> never take a job for which you meet all of the "required skills and experience"

Is there a way to do this without knowing someone who can get you through the HR firewall, then being known as "That Idiot" until you figure it out?

EDIT: Difficulty, you must be an average programmer. Linus could probably get a job wherever.

Since we're all "That Idiot" to somebody anyways, might as well not worry about it.

Leaves the HR firewall. You undermine that by having somebody on the inside refer you. Or by having a work history that gets you in the door (which, of course, has a bootstrap problem). Or by working on OSS in that field. In other words: Anything that makes you stand out positively from all the other average programmers.