> 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 would concentrate on this. Why are you feeling this way? Is it possibly because you compare yourself to others? Or you compare yourself to the "ideal world" that lives in your head based on the things that you read on the internet and experience of others?

I'm sure you have lots of positives in your life right now. Are you starving? Do you have roof over your head? Do you struggle from any health problems or mental diseases? Are you addicted to anything? Do you have friends? Do you spend enough time with them? Can you exercise? Can you pay your bills? Do you have savings to whether turbulent times?

I bet if you switch focus to something that you already have and where you already at it will help you. Switching mindset where you think not from backtracking from Ideal situation back to your life, but to switch that to start thinking from where are you now, and what are the next smallest step that you can take?