Your post doesn't say what career you want or even that you want a particular career. Until you make that decision, I'm not sure it's possible to strategize, plan or brainstorm effectively.

I wrote the following on the assumption, which may be wrong, that you're interested in programming and want to do it professionally.

> How did you pinpoint new directions that matched your skills and interests?

I just chose to do what I enjoy, and I happen to enjoy solving problems and working with computers.

> What were the most effective ways to reposition your experience in a new field?

I didn't. Other people did that for me.

> Are there any resources or strategies you’d recommend for upskilling or building networks?

To be skeptical of anybody who tells you they know how to do this.

Bootcamps can be valuable -- or may have been some years ago. Not sure. The people I knew who did bootcamp courses had the outcomes I'd expect, namely that the smart, organized ones who were likable and devoid of personality disorders did well.

Be willing to take a bad job temporarily, or work as a contractor, just to get your foot in the door of the field.

> most advice has been starting at the bottom as an IT helpdesk worker and going from there

Be skeptical of anybody who tells you this, too. It may have been a viable path into the field in the 90s and 2000s. It may still be today, too, but I haven't seen any evidence that it is. I've never met anyone who has made this particular 'jump.' 99% of my team have CS degrees.