I went to the worst schools imaginable but eventually got two Master's degrees (online - terrible school rank) but I took the opportunities as they came. All schooling is what you make of it though - no one ever questioned my education or made any issue of it. Perhaps I missed out on some interviews here and there but I will never know. All interviews are about what I've accomplished after I started working.

So I got a Bachelor's first, then about 10 years later my first Masters. Five years after that my second.

I had a small debt load - about 25K. I paid it off over time.

I've been in the workforce for 20 years now. I started as a programmer but left it to be more of a generalist/project manager. These days I'm running application support teams (and still projects) and spend most of my time on stakeholder management and budget management.

At first I made very little. When I graduated all the jobs were either in Sales or Computers. This was the Windows 3.11 era. Email was on VAX/VMS. My first nice pay hike was after about 5 years I got bumped to like 75K. After a few years I got up to 6 figures. Now I am making great money.

I should be able to retire fairly well off - maybe 1.5-2 Mill.

I did not marry wealthy. My wife was dirt poor and never really worked. I also came from lower middle class.

Just keep improving yourself. Always be involved in something outside of work to make yourself more valuable.