“Should I stay or should I go now?
If I go there will be trouble
And if I stay it will be double
So you gotta let me know
Should I stay or should I go?”
Because if you decide that yes, it’s indeed time to go, you’re going have to close the door behind you before you can open the one in front of you.
Like at a dog park.
Or an aviary.
Or a prison.
And whether it’s escaping physical incarceration or career stagnation, the barter remains the same: you’re swapping stability for opportunity. Because long gone—with a few exceptions, of course—are the days of the methodical, linear ascension inside a single company; the dealer becoming the boxman becoming the floorman becoming the pit boss becoming the shift boss becoming the casino manager, and so on.
Or, on the supplier side, the cubicle-jockey grinding his or her way into the C-suite.
Want to test this theorem? Look no further than where you work, and you’ll likely find that most senior executives indeed came from somewhere else. They weren’t draft picks; rather, they were free agents recruited away from solid jobs at solid organizations. Places where they not only knew everyone’s name, but where all the bodies were buried and the skeletons were closeted. Places where they were well comped and well respected.
Ambition makes you do that.
That or craziness.
Aesop famously wrote about the dark side of such appetites in his fable about the dog with a bone in his mouth. You know, the dog sees his reflection in a pond, and thinking it’s another dog—and more importantly, another bone—he barks to scare him away, unwittingly dropping his own bone into the water.
Yet every day in our world, folks bet double-or-nothing on their careers, switching companies for more money. Moving overseas for a promotion. Broadening responsibilities to impress the higher-ups. And all the while waving a balled fist at the Peter Principle, which as we know is pretty good at exposing those folks whose aspirations exceed their aptitudes.
So, to circle back to our musical question, how do you—yes, you—know it’s time to stop doing what you’re doing and start doing something else?
According to Harvard Business Review, there are a few telltale signs you should look for. For example:
“When Alexander saw the breadth of his domain,” says Hans Gruber in the movie Die Hard, “he wept for there were no worlds left to conquer.” Sometimes it happens. Whether you’re a Greek king or a regional rep, sometimes you work somewhere long enough and literally accomplish all your goals. And now, with upward mobility perhaps stunted, you atrophy, doing nothing more than repeating the same experiences over and over, the only thing that changes being the weather and the calendar.
Code name: SSDD. When you get there, it’s time to change direction.
Working for the Weekend
Be fast and be honest—every dozen years or so, when Christmas falls on a Tuesday and you’re getting four or maybe five days off work, are you happy or horrified? For the most part, if you’re more excited about not performing your job duties than performing them, you may need to consider busting a move out of there. You’ll be doing yourself—and not to mention your employer—a favor.
And as Breaking Bad proved (and so did Game of Thrones, except in reverse), people judge you on how you end.
Don’t botch your exit.
Burn Baby Burn
You’re burned out. Torched. Toasted. Not anyone’s fault, but you just can’t deal with any more inputs, any more problems, any more tasks or assignments or arguments. Like with poker or pinball, you’re on tilt.
When it gets to that point, what’s the point?
Opportunity of a Lifetime
Oprah Winfrey left her gig at a local news station to start her own talk show. Now she has her own network, called, coincidentally, OWN. Robert McNamara left his job as president of Ford Motor Company to be Kennedy’s secretary of defense. Years later, Lee Iacocca left his job as president of Ford Motor Company—well, to be fair, Ford left him—to become CEO of Chrysler. And GOAT quarterback Tom Brady retired after 21 seasons in the NFL so he could fulfill his dream of spending more time with his wife and children.
How can you pass up a chance that doesn’t come with a second chance? You’ve got to go for it, even if it means sacrificing seniority and goodwill and the familiarity you’ve nestled yourself in over the years. Steve Harvey has a great speech where he uses the metaphor of “jumping” into the unknown. (It’s a bit preachy for some tastes, but it’s definitely worth a listen.)
Just don’t fear the fear. All those high achievers around you have stared down the same dilemma in their careers. And the one thing they have in common is they seized the opportunity rather than being so scared that the opportunity seized them.
Read that last sentence again and think about it.