Career Smarts: How Do You Know When Your Run is Done?

This is a picture I took of Red Sox General Ma...

Theo Epstein

There are jobs that last a lifetime, and jobs that are over before they really start. In between is the job that has a predictable arc with a start and a finish; you just need to know when it’s time to move on.

And in the C suite, where fortunes might be made, and juggling competing egos and agendas can be a full day’s work all in itself, the risks and rewards of figuring this timing stuff out is even greater. What’s clear on the exec team is that you have the greatest leverage to get things done when your skills and background are highly valued, and little better than a dog’s breakfast when you’ve fallen out a favor and folks don’t think they need what you offer any more.

So someplace between walking in the front door and lighting things up, and being left out of crucial conversations (and the floor taco party) is the apogee of your arc; the high point in terms of leverage and impact.

While it may not always be one high point (there is always the prospect of a two, or three humped trajectory), you maximize your career trajectory if you move on – whether it’s a different role in the same firm or a new role in a new firm – before you’re asked to step down.

This dynamic happens everywhere, but is most visible in sports where the spotlight is brighter, journalists less charitable, and word and rumor spreads faster.

A great example of Exhibit A of this phenomenon of knowing when to move on is 37 year old Theo Epstein, who recently signed a five year contract to become the president of baseball operations for the woebegone Chicago Cubs. Epstein  had a nine year run – and two World Series crowns – as general manager of the Boston Red Sox before taking on the new challenge of the Cubs. The Chicago team has not won a World Series since 1908. His accomplishment with the Red Sox? Gaining two world championships for a ball club that had not won a World Series crown since 1918.

Epstein’s move comes after a season in which the Red Sox had an epic home stretch collapse –  a dive that baseball pundit Nate Silver argues is the worst ever in baseball – and failed to reach the playoffs. While Epstein’s job was likely safe for another season or two, the proverbial handwriting was on the wall. Ron Washington, who managed the Texas Rangers to the last two World Series, is already getting the same hostile treatment for not bringing the bacon home in terms of a championship this season.

So how do you know when it’s time to look elsewhere? Here are three thoughts;

  1. You always want to be wanted,” said former Kentucky head basketball coach Tubby Smith as he took a similar role with the University of Minnesota. Smith had won a college basketball title his first year in the job, but had not won another in the following 8 years. Regarding Minnesota he said, “You know they have a need.” Working someone where your input counts, and folks seek you out is one criteria.
  2. Your setbacks outweigh your triumphs. No one loves a loser and the time to get moving is before things blow up, not after, even though those setbacks may say more about external conditions than your skills and abilities.
  3. You’ve done all the you can do, and don’t have anything to prove to anyone, including yourself. CEO Meg Whitman left eBay, after she had a ten year run that saw her lead a highly successful IPO, and grow the company into a $40B operation. She took some time off, ran for and lost an election for governor of California, and recently got a chance to salvage the former pride of Silicon Valley, Hewlett Packard.

Cut to the chase

My career advice? Do what you love to do, work hard, do great work, play nice and keep your eyes wide open. To crib that well known restaurant adage (3 most important qualities in the business? Location, location. and location), timing is just about as important in careers.

Life Back West is an occasional set of writings focused on ways people, teams and organizations can be both more effective (doing the right thing) and more efficient (doing the right thing well). More about executive, career and team / leadership coaching services can be found at the “About J. Mike Smith and Back West, Inc.” sidebar or the “Hire Me” tab above. You can also read an online interview with me at WhoHub, as well as participate in my learning community courtesy of KnowledgeCrush.


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