For a little background, I was probably in the middle of how you and your cousin grew up. Like you, I had my liberal arts degree paid for, but any fuck-up meant I paid for that semester, which I learned the hard way twice. Dad bought my first car for me, but I had to pay him back interest free (so I wasn't paying interest to anyone). In 2009 I got my first full time job working overnights frying donuts so I could continue going to school during the day, etc. I am also the black sheep of my family (adopted, not doctor/investment banker/lawyer), and struggle all the time with not living up to the expectations of my parents.

I always hear that I should have gone to medical school, that I should have done more with my intelligence, etc. I wonder if your cousin is told that kind of thing by your family. I'm 31 now, but throughout my 20s this was a very difficult thing to hear all the time. It stagnated me, and held me back from having any kind of faith in myself.

I'd tell him that it's ok to be afraid. That it's ok to do things and not be sure if they'll work out. That it's ok to learn from your mistakes and not have a clue of what you're doing. That it's smart to have a backup plan, but not to hold yourself back from living life just because it's different than what you've lived for the last 23 years.

"Do what you want" is pretty vague and honestly kinda scary. The freedom to do what you want is pretty terrifying when you've grown up being told everything you can't do, or everything you "should" do, and never necessarily doing what you "want" to do.