My parents owned their own business which had its ups and downs. Prior to my entry into college it was mostly downs. As a result it was always clear to me that I was going to be "on my own". I am 55 and was FI at 40 but still work. I own my own business which was more successful than my parents. However, I cannot say I love what I am doing and probably will retire within 1 year as soon as I put a transition in place. Because of some degree of success my kids do not need to be "on their own" and can truly do what they enjoy. My wife and I felt the need to let our kids know that in pursuing a career choice they should do what they love because if you do that you never work a day in your life. One is currently a senior in college and the other is entering college in the fall. When they started looking at schools we let them know in broad terms "where things stood" and that they have some leeway in choosing a career.