I recently had a conversation with a guy I have known for years. He has become, in middle age, what is known in the business as a “serial CIO.” These are CIOs who quickly move from job to job, frequently for the wrong reasons. I hear from him several times a year. Right now he is, as is frequently the case, out of a job. In fact, he has landed and lost three CIO positions over the past five years. He has now been unemployed for over a year and is finding that his past has rapidly caught up with him.