We pick our careers in various ways – follow in a parent’s footstep, admire people we deem successful, or like me, influenced by a teacher who challenged me to go to medical school. I took up the challenge and after ten years in medical practice, decided it was not the career for me and made a leap to financial planning. It was a tough decision, and a couple of people through the years commented on the guilt I should feel about this decision. How do we deal with career dissatisfaction? Should we feel guilty about changing careers? And if so, how do we deal with that guilt?