> I feel like a freaking loser given my age and my relative career stagnation / my inability to actually turn my mildly above average skills into any real money

> I feel like a freaking loser given my age and my relative career stagnation / my inability to actually turn my mildly above average skills into any real money. It is okay to feel like that for a bit. But, this story that you are telling yourself is not going to help you if you keep on telling this. Whenever I have felt negatively about myself like that in the past, it has helped to stack some wins -- even if little ones -- to get out of the rut. So, if you want to try to be an engineer, start building things using tools/tech that you are interested in and put them in the open source. Or better yet, help out some open source projects that you respect and have benefited from in the past, if you can. Hiring managers (and I have been one) look for real evidence of skills mentioned in the resume and a well-rounded Github repo increases the likelihood of a callback in any kind of market. Stack some little wins there. OR, if you want to be a product person, do the equivalent of stacking some wins in that realm. I have very little experience in that space so maybe someone else here can identify a concrete thing or two that you could do to attract hiring managers in that line of work.