I found this through reddit, and saw you were looking for ideas on how to improve. I think you might want to delve into Charles’s motivations a bit more…what makes him tick, and why hasn’t he been happy with his other careers?

One idea to end it a bit less abruptly would be to say something that tied the careers together, like:

Anna looked over the list of careers. “Have you ever considered a career in management? Like your ranch hand experience, managers deal with crap all the time. Like your welding experience, managers try to hold things together. And, like your assistant press secretary experience, they have to make it sound like everything is going according to plan throughout the entire ordeal.”

If you wanted to carry the story further, you could then refer back to his varied experiences, talking about how each problem relates in some way back to one of his prior experiences. There are opportunities for humor by having a particularly obscure job (rescuing sea turtle eggs) relate to a current job in business.

Anyway, just some thoughts. Keep writing!