I’m not too hung up on Keith’s job progression. He reminds me of my cousin who is a good person and very hard worker, but not a go-getter for the next progression. It wouldn’t surprise me that Keith did what his friends did when graduating HS, then heard about someone who did a medical certification and got a good job and decided to do the same. When you fall into things rather than actively pursue things it takes longer. I do fault Keith for the talk of becoming a doctor BS. Yes, you can change careers at any point but given his age, the expense and difficulty of a medical degree, and the amount of time it takes it just isn’t a good fit for him right now.