Want to Quit Your Job? Ask Yourself These 3 Questions First

Illustration of a woman with a briefcase walking through an exit door

Illustration by Giovanna Pineda/Katie Couric Media

Plus, how to explain gaps in employment when you’re looking for your next role.

Is it time to put in your two weeks’ notice?

That’s the question so many American workers have asking themselves lately. Millions of them did quit during the height of the Covid-19 pandemic, and while we’ve read dozens of headlines about the “Great Resignation,” it’s challenging to make that big idea feel personal. Deciding to resign can be scary, and it’s not a decision that should be taken lightly. So how do you know when your current job has run its course and it’s time to get the heck out of there?

We got the scoop from Andrew McCaskill, an official career expert at LinkedIn. He closely follows trends in hiring and the job market, and he uses that data to help people strategize about taking control of their careers — which includes giving advice that they might not otherwise get in the official channels of their companies. “It’s kind of like being the guy in the cubicle across from you who will answer the questions that you wouldn’t ask your boss,” he says.

McCaskill tells us that while people really are quitting (or thinking about quitting) in significant numbers right now, that’s not the entire story. “People aren’t resigning from their jobs and just going home to chill out,” he explains. “They’re actually changing jobs and moving to other positions.” He calls this a “career awakening happening across the country,” and much of it stems from burnout that’s leading folks to ask deeper questions about their careers, like why they do the work they do or how they can be more fulfilled as they do it.

The pandemic has changed the job market significantly for many types of workers, which has made employers more flexible and open to meeting their employees where they are. That means now is a potentially great time to quit and try something new, but it’s not a decision that should be made without careful consideration.

The first step is taking a personal inventory about why you’re feeling unsatisfied. “Don’t conflate your feelings about the world at large with your feelings about your job,” he says. “No one is happy at work all the time. No one is stoked to come in and turn on that laptop every single day. So you have to be really thoughtful about it.”

We talked with McCaskill about how to decide if quitting really is the right decision for you — and how to find your next great opportunity.

How do you know when it’s time to quit your job?

Before you start planning how to resign, first ask yourself whether now is the right time to do it. McCaskill recommends reflecting on these questions to determine if you’re ready for a career change:

Can you grow in your current role? 

If you don’t have a plan for growth at your company, that’s the first red flag that it’s time to move on. But McCaskill says that doesn’t necessarily mean getting a promotion — it’s more about whether you’re developing in the areas that are important to you. “We’re no longer in a place where job growth is just about the next rung on a ladder of titles,” he says. “Job growth can really be about expanding the purview of what you’re interested in doing. Is the job you have right now preparing you for the next two jobs you want to have in your career?” If you’re still getting opportunities for further education, big projects, or stretch assignments, you likely have still room to expand in your role. But if those things have dried up, start looking onward.

Are your coworkers leaving? 

“If tons of people are jumping off the ship, you might want to grab one of those lifeboats, too,” McCaskill advises. He says high levels of employee turnover is a crucial warning that all is not right at the company, particularly if the folks who are leaving are the ones with whom you most closely identify. “For women, people of color, and queer people, if colleagues that look like you or are part of your community are leaving in droves, that’s usually a sign,” he says. It’s also telling when the exodus is happening at a senior level, where workers are more privy to the headwinds of the organization. “Especially if it’s people you really respect, you’ve got to start to say, ‘Is something coming down the pipe that I don’t know about?’”

Does your work align with your values? 

“People want to be proud of the places where they work — no one wants to go work for Voldermort,” McCaskill says. This issue is likely most relevant to knowledge workers or folks who have flexibility and mobility in their careers, he adds, but for those who can consider it, it’s a significant piece of the puzzle to being happier in your job. Think about your company’s culture: Do you feel good about their mission? How do they treat employees? Is it an equitable environment for all? “If you don’t feel proud to tell people where you work, that’s another sign,” McCaskill tells us. “That’s a really interesting place where people have the opportunity now to think and be pensive about that, and employees are in the driver’s seat. So a lot of them are taking the keys and saying, ‘I’m going to go someplace else.’” 

How can you sell yourself if you’re looking to make a career pivot?

One of the most frustrating career experiences is feeling like you’re ready to make a change, but worrying that your previous work history puts you in a box that potential new employers won’t be able to look past. But the reality is that your skills are likely much more transferable than you might think — and it’s never been easier to train yourself on the ones you don’t have.

McCaskill recommends doing “a reimagination of your skills” and thinking differently about how you tell your own professional story. But where to start?

“Go old school and print out a job description of the openings that you would love to have,” McCaskill explains. “Look at the skills that are required for that job, find the ones that you have, and match them up. Where you have gaps between your skills, think to yourself how you can fill those in.”

That practice will reveal which of your skills are highly transferable, and you can work on your areas that need improvement easily, thanks to so many accessible training options, like online courses and certifications. It will also reveal what kind of language the employers you want to work for use to discuss their ideal team members, and you can use that same language as you learn to describe yourself in a different way.

“Look at keywords in the job descriptions that you’re interested in, and put those words in the way that you tell your story on your LinkedIn profile,” he says. “That’s really important because recruiters use LinkedIn to find people for work. Six thousand people get a job every day on LinkedIn — that’s a fact. So use those keywords in the way you talk about yourself and your experience.”

If you quit without another job lined up, how do you explain the gap on your resume?

Leaving your job without a plan for what’s next is a big risk, but for some people, it’s the right decision. That could be because of concerns about your mental health, your needs for childcare, or any number of individual factors that only you can understand. If you’ve made the personal choice that leaving now is what you need, you’re probably wondering how you should explain that when you’re looking for your next role.

McCaskill says this is one of the most common questions he gets through his direct messages on Twitter. And there’s good news: “The reality is that recruiters are not looking at gaps in your work history the same way they did before,” he tells us.

We’ve all heard the advice that we should “save for a rainy day,” and the radical upending of our professional lives since 2020 is one of those events. “There’s nothing like a global pandemic to qualify as a rainy day,” McCaskill says.

Recruiters and employers are much less likely to ask about a gap on your resume today than they were three years ago, and that’s largely because so many candidates will have those stretches of not working. You may still be asked about the gap — though it’ll be with much less judgment than you might have met before — and if you are, the key is to be honest about how you spent the time and explain how that period away from work was advantageous to not only you but also to your next employer.

McCaskill took a year away from corporate America himself, and this was before the pandemic, so he’s got great experience in learning how to discuss that leave of absence.

“I was very candid about it,” he says. “When somebody asked, ‘What are you doing now?’, I was very honest and said, ‘I am taking amazing care of my family, I am going to the gym more than once a week, and I’m preparing to be the best possible addition to someone’s new team.”

He encourages people not to demur when asked about time off. Instead, feel comfortable leaning into how you used that period for self-improvement — and know that the nuances of your professional choices are being understood in a way that they often weren’t in years past.

“There’s a lot more conversation around empathy in corporate spaces now than what we’ve had previously,” McCaskill says. “We’re talking about equity out loud at work. We’re talking about taking a mental health break out loud at work. And those things are normal because hiring managers are getting burnt out too. Even at LinkedIn, we’re leaning into giving you better options to talk about career gaps on your profile. We’re destigmatizing it as much as possible.”