RealThndrMonkey at 2015-08-19 13:13:25:
I sometimes start with what is their job and then follow up with what they see as their dream job.
From there I look to why they can't, haven't or unable to reach their dream job. How did they get their current one? What they think of that job? I can adjust this easily, regardless of the character age. Even if they're retired, why did they retire? Did they like that job? What was their dream job when they were working? What do they wish to do with their time now?