If you’ve ever been to a party, you know that awkward dilemma: When should you leave? Bail out too early and you may miss out on fun and meaningful connections. Stick around and you may end up overstaying your welcome—often without realizing it.
Knowing the right time to head for the exit at a job can be similarly tough to gauge—and a lot more consequential. Leaving prematurely carries risks, as does staying too long. But Sanjay Khosla, a senior fellow and adjunct professor at the Kellogg School, argues it’s better for career growth to err on the early side.
“Often individuals leave a company when it’s too late,” warns the former senior executive at Unilever and Kraft International, who is also a trained executive coach. Khosla contends that people should keep the party metaphor in mind and start eying the exit when their time with a company has reached the equivalent of “5 to 12,” as he likes to say—and not when it’s 5 minutes past.
In other words, determining when a positive experience has peaked and you may be approaching the point of diminishing returns can be as crucial to your career as to your social life.
Khosla identifies three signs that you may have reached “5 to 12” in your current organization. This is when it is time to plan a graceful departure rather than overstay and harm your career prospects.
1. When your growth stalls
One way to know that the hour is getting late is if you suspect that your personal career growth within an organization has stopped.
Khosla tells the tale of a senior leader at a large multinational.
Kate (not her real name) had been with the company for more than 20 years, earning consistent promotions. She expected to retire there.
But Kate started sensing that her career growth within the organization had plateaued. She worried, too, that a few of her peers might move ahead of her. Two of them were invited to an extended leadership conference, while Kate was not.
“She was being taken for granted, and she also felt that she was just being viewed as a solid performer rather than a superstar,” Khosla says.
Kate told Khosla about her concerns, and he urged her to start exploring external options. He told her, “You don’t necessarily have to take another job. But if you don’t open doors, you’ll never know.”
To pursue alternative opportunities, Khosla advises leaning on a network of people you know and trust—what he calls a “circle of influence.” A circle of influence should include colleagues and managers from both inside and outside your company.
Ultimately, Kate landed what Khosla describes as a “bigger job” outside the company. The new role challenged her in ways her previous position no longer could and pushed her to keep growing, both personally and professionally.
“There’s a bigger world outside,” Khosla says. “Most people get so into the current world where that’s all they know. Change is difficult. It’s uncertain.”
2. When you have a bad boss
Many people leave a company because they have a terrible manager. They might otherwise love their job in the organization, but poor supervision puts their career clock at “5 to 12” sooner than they might expect.
Khosla gives the example of a talented, ambitious, and high-performing individual he calls John. John’s rise through the company had been strong, he admired the culture of the organization, and he respected its values.
“The problem was his boss, who was just toxic,” Khosla says.
John bristled at what he perceived as his boss’s unreasonable demands and micromanagement. Occasionally, the boss would ask John for something on a Friday with delivery on Sunday evening and then not bother to look at it.
His boss also took credit for John’s work. John would prepare a presentation, and his boss would claim it and accept accolades without mentioning John’s contribution.
John tried through human resources to see if he could change departments within the company. The response wasn’t encouraging.
“He was quite stressed,” Khosla recalls.
Khosla reminded John about recognizing when it was “5 to 12.” John secured a great job outside the company. So as hard as it can be, leaving an organization you love to get away from a horrible leader can be worth it for the sake of your career growth.
“Leaving is never easy,” he says. “But life is too short to be stuck with a bad boss for a long time!”
3. When comfort becomes your biggest risk
Sometimes a task that started out as rewarding and intellectually stimulating can turn into a mindless chore once you’ve mastered it. So, Khosla notes, it might be nearing “5 to 12” if you have gotten too cozy in your role.
To grow your career—and stop feeling like you’re doing busywork—it is important to recognize when it is time to step out of your comfort zone.
Take Emily (not her real name). With a great job in a senior role at a large multinational, she was handling a significant brand worldwide and doing well. She was also very comfortable in the job.
“In fact, too comfortable,” Khosla says. “The challenge part had gone.”
Emily told Khosla she was missing excitement and adventure in her career.
“I just feel like I’m on a treadmill going nowhere,” he recalls her telling him. “I can do my job when I’m asleep.”
Emily asked Khosla if she should stay in her current role and be safe, or if her time with the company might be at that “5 to 12” inflection point. To Khosla, it was clear where the hands of the clock pointed.
She was offered a role at a smaller company in the technology sector. The firm didn’t have the support systems and bureaucracy of the large multinational where she worked, which could have deterred her, but instead excited her. Emily decided to take the new job—and she’s having the time of her life, according to Khosla.
“That leap was risky,” Khosla explains. “It has a lot of stuff you have to do yourself. There’s less structure. There’s more ambiguity. Now she’s working much harder, but that work has meaning.”
In Emily’s case, as with others, Khosla advises supplementing your “circle of influence” by holding focused conversations with select headhunters.
Khosla offers a caveat to this outreach, however. These recruiters should always be introduced through a contact, rather than emailed cold. In fact, Emily’s next chapter came through a friend’s connection.
“You just signal your interest to those around you,” Khosla says. “And you’re in a position of strength because there’s no urgency to leave.”
Whether departing feels like an emergency or a matter for the back burner, what’s important is to consider your alternatives early.
“Don’t wait for a crisis to force your hand,” Khosla says. “Try and take your career and your own path in your own hands as much as you can, as early as you can.”