My skillset was “really old” in 2008 at 34. I was still doing VB6 (7 years after it had been discontinued) and C++/MFC (Windows). What I did have is a level of maturity and the ability to talk to customers and knowing how to get things done.

I went to a company that used modern technology and learned how to talk the talk and built my resume.

But if I were in that position today instead of 2008, I would spend as much time as it took to study data system and algorithm style interviews - ie “grind leetCode and work for a FAANG” (tm r/cscareerquestions).

I fell into a remote role at $BigTech through the cloud consulting department specializing in enterprise application development where that wasn’t necessary.