Major life transitions such as leaving the protected environment of school or starting a new career can be daunting. It is scary to face a wall of choices, knowing that no one is going to tell us if we make the right decision. As head of the Stanford Technology Ventures Program, Tina Seelig’s job is to guide her students as they make the difficult transition from the academic environment to the professional world—providing tangible skills and insights that will last a lifetime. Seelig is a wildly popular and award-winning teacher and in What I Wish I Knew When I Was 20 she shares with us what she offers her students—provocative stories, inspiring advice, and a big dose of humility and humor. We discover how to have a healthy disregard for the impossible; how to recover from failure; and how most problems are remarkable opportunities in disguise.