How do you know when you are successful? Your bank account, your house size or your job title speaks to an “accomplishment”. Is the measurement external, such as buying a fancy car, and/or is it internal like feeling good about what you are doing? I maintain that for so many of us, the success metric is unconscious. meaning that we are trying to please our parents, our siblings, or those who early in our lives were very important to our growth and development. Elaine, fifty-one, went to a prestigious law school, graduated with a great job, made boat loads of money, quit her job and decided, at the age of forty, to settle down and have a family. Neil, a high school classmate of Elaine, also went to a prestigious law school, graduated with what he called a “mediocre” job, and he has felt like a failure, ever since. Elaine thought that having a successful professional practice would make her happy and when she realized she felt lonely, she turned her life in a different direction. Neil, imagining a financially secure life, now faced with some significant financial hardships brought on by raising his family in the way he wished he had been raised, now looks at himself with disgust and disappointment. Elaine never felt that her bank account had any reflection on her sense of success. She was looking to feel good about her life. Neil, by contrast, believed for many years, that financial success, would prove that his hard efforts paid off, and so without a sense of financial security, he has let himself down, and I suspect his parents, as well. Both Neil and Elaine grew up lower middle class, but Elaine’s family never encouraged her to “change her life,” whereas Neil’s family saw Neil as “breaking through the barriers into economic freedom.” If life is all about expectations, I would add that it is the expectations of our caretakers, that most of us, without examining our life, are slaves to. In other words, our default motivation is to fulfill the expectations of our parents. Only with deep introspection can we begin to change that.