Lessons on Career Advancement from 43 Year-old Chicago Cubs President Theo Epstein

Theo Epstein (b.1973), president of baseball operations for the Chicago Cubs, has thus far had a stellar career as a sports executive.

As a freshman at Yale, Epstein was assertive enough to flaunt his role as a sports editor for the Yale student newspaper. After cold-contacting many professional sports teams to express interest in working for them, he grabbed the attention of a Yale alumnus at the Baltimore Orioles. This stroke of luck led to three consecutive summer-internships at the Orioles with increasing responsibilities.

After graduating from Yale with a degree in liberal arts, Epstein joined the Orioles full-time as a public relations assistant. His ingenuity caught the eye of Orioles President-CEO Larry Lucchino, who took Epstein under his wings. When Lucchino became team president of the San Diego Padres, he took Epstein and made him director of player development.

At Lucchino’s suggestion, Epstein also attended law school full-time whilst working 70 hour-weeks at the Padres. At that time, nobody on the small Padres’ management team had a law degree. By going to law school and getting a Juris Doctor degree, Epstein could help review players’ contracts. “Getting that seat at the table gave me the opportunity to be involved, and then my responsibilities grew from there,” he once recalled.

At age 28, Epstein moved again with Lucchino and joined the Boston Red Sox as general manager. In doing so, he became the youngest general manager in the history of Major League Baseball. Ten years later, in 2011, Epstein became president the Chicago Cubs.

At both the Red Sox and the Chicago Cubs, Epstein intelligently used complex statistical analytics to oversee the teams’ curse-breaking championships. In 2004, Epstein supervised the Red Sox’s sixth World Series Championship and ended their 86-year drought. And in 2016, when, under Epstein’s presidency, the Chicago Cubs finally won the World Series Championship 108 years after the previous time they did, their triumph ended the longest drought in professional sports.

Theo Epstein’s 20 Percent Rule: Undertake Your Boss’s Less Glamorous Responsibilities

In a recent interview (22:31-minute mark in this “The Axe Files” podcast) with the University of Chicago’s David Axelrod, Epstein revealed a career advancement technique that helped fast-track his career at the Orioles, the Padres and the Red Sox:

Whoever your boss is, or your bosses are, they have 20 percent of their job that they just don’t like … So if you can ask them or figure out what that 20 percent is, and figure out a way to do it for them, you’ll both make them really happy, and improve their quality of life and their work experience. And also gain invaluable experience for yourself. If you do a good job with it, they’ll start to give you more and more responsibility.

Idea for Impact: Those Who Raise Their Hands Climb the Ladder Faster

Human nature is such that everyone likes to do what he/she likes and not what should be done. If you can determine those aspects of your boss’ job that she hates and volunteer to help her with those responsibilities, you can expand your job’s horizons.

When you can seize such opportunities to raise your hand and sign up for tasks and responsibilities that aren’t particularly attractive, you not only learn by way of broader experiences and gain confidence, but also become more visible to management and situate yourself for a promotion. As I’ve written previously, before you can be seen as eligible for promotion, you should have demonstrated competence in doing a part of the new job you aspire to.

Seek out projects, prove that you’re eager and able to go the extra mile, and gain valuable face time with top executives.