I'm glad I chose not to do the Criminal career. Aside from the bug, I was worried that getting arrested and thrown in jail would interfere with promotions. I also managed to avoid the Sports career, even though it was part of my original plan.
I chose all of my careers before I started the challenge. Paul was going to focus on athletic and logic skills (Special Agent, Medical, Military, Sports) while Linda concentrated on charisma and relationships with co-workers (Culinary, Symphonic Music, Journalism, Politics). I also decided that whoever was lagging behind after three careers was going to switch to Business for their fourth. I knew from my Apocalypse Challenge that an ambitious, workaholic schmoozer could reach the top of the Business career in less than two weeks. I hoped this would increase my chances of both of them finishing at the same time. It worked out pretty well as they both finished their final careers only one day apart.