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Advice / Career Paths / Career Change

4 Ways to Know if You're Ready to Leave Your Comfort Zone and Get a New Job

Jennifer Goff was fresh out of college when she landed a dream job at a thriving art gallery in San Francisco.

Before long, she climbed the ranks to become the director of PR and media. She loved it, but after three years in the role, she began to feel restless.

“I had adapted to the continuous deadlines, and had established smooth, efficient routines—yet I was less absorbed by the work,” says the 27-year-old Goff. “I no longer had moments when I felt ‘in over my head.’ And, oddly, I missed that.”

After reflecting on her situation, Goff realized that she wanted to expand her writing and marketing skills beyond what her current gig offered. So she made the difficult decision to move on, accepting a content marketing job at an Austin-based startup.

“My team in San Francisco was extremely close-knit, so it was hard for me to say goodbye,” she admits. “But I looked ahead to the benefits that could come from exploring the unknown.”

In fact, Goff recalls a quote from Yahoo president and CEO Marissa Mayer that really resonated for her when she was contemplating the career move: “When you have different options, you should choose the thing that looks like it will be more difficult, because that usually turns out to be the right choice.”

“At first, I felt disillusioned that my ‘dream job’ was no longer the right fit, but at the same time, admitting that was incredibly freeing,” Goff says. “For anyone facing similar feelings, the advice I’d give is: Embrace it. Jump into something new.”

Easier said than done, right?

This can be a particularly anxiety-provoking proposition if you’re one of the many people who lost a job during the recent recession—or if you’ve clung to a less-than-awesome gig out of fear of being unemployed.

“Most of us are wired to crave stability,” says career coach Matt Youngquist, president of Career Horizons in Bellevue, Washington. “The recession took away our sense of security, and now that it’s over, people are starting to take a deep breath and are happy to finally be in a place of relative calm.”

With this in mind, we’ve put together a four-step action plan that can help you assess whether it’s time to take that big career leap yourself.

Step #1: Figure Out if You’re Staying Simply for the Sake of Staying

It’s a no-brainer to leave a job because the hours are killing you, or your boss is a carbon copy of Miranda Priestly.

It’s another thing entirely if nothing is wrong, per se, except that you’re coasting instead of growing. So if you have a nagging sense that you’re running on autopilot, it’s probably time for a gut check.

“Ask yourself whether you’re too comfortable, and honestly analyze your feelings by talking it out with friends,” says Deborah Brown-Volkman, a career coach and author of Coach Yourself to a New Career:7 Steps to Reinventing Your Professional Life.

She also recommends composing a pro-con list comparing the benefits and drawbacks of staying versus moving on. “This gives you objectivity so that you can make a fair assessment,” she explains.
It also pays to dip your toe into the job-hunting pool.

“People who’ve been out of the game for a while are often unaware of what opportunities are even available,” Brown-Volkman says, adding that this is especially true if the recession’s dearth of options intimidated you into staying put.

So check out job boards and LinkedIn, and also make an effort to reach out to people in your network. Sometimes sniffing around informally like this can be enough to get you over the initial fear of making a change.

Step #2: Get Real About What Really Matters to You

Just to be clear, feeling comfortable in a job isn’t necessarily a bad thing. But if you want to climb the ladder as high as you can, your path is going to look very different from someone who values a flexible schedule and plenty of vacation time.

To suss out your own priorities, you need to get really specific by ”breaking things down into testable benefits,” Youngquist says.

She offers up this example of the kind of key questions you should ask yourself: If you crave better work-life balance, what would that look like exactly? Working from home once a week? Never staying late at the office? Moreover, how much would you give up for those perks? Would you be willing to take a pay cut?

This kind of seemingly simple career soul-searching can often lead to a clear answer.

Take the case of one of Youngquist’s clients—a rising star at Boeing who wished she were at a smaller startup, where she could have more impact.

“When we sat down and looked at her current benefits and job stability, we realized that she would probably backtrack if she jumped ship,” Youngquist says.

As Youngquist explains, her client was shocked to learn that the average tenure at young tech companies was just two and a half years—never mind the long hours—whereas Boeing ranks in the top 3% of businesses in terms of longevity.

Since she had already put in so much time building a bulletproof career for herself at Boeing, she decided to play it safe and stay—with a newfound sense of appreciation for what she had.

Step #3: Research if a New Job Is Worth the Move

If you’ve found a job you’re really interested in, go ahead and apply—but be sure to do your homework along the way.

A good first stop is Glassdoor, where you can find employee reviews of a company’s internal environment. “If seven out of 10 people report that, for example, an organization doesn’t promote from within, that’s something to think about,” Youngquist says.

Next, do a LinkedIn search on the firm to find out if anyone in your extended network has worked there—or is connected to someone who has—and ask if you could have five minutes of their time to discuss a job opportunity you’re exploring.

Once you’re actively interviewing, Youngquist recommends carefully evaluating the culture to get a sense of how they treat employees. Were you jumping through hoops during the interview process? Did you get a good feeling from the staff you met?

And don’t be afraid to ask tough questions yourself: Where have previous employees in this position ended up? What are the biggest challenges involved in this job?

Think of it like dating. If you pay attention in the early stages—did your date text you back, or leave you hanging? are you always picking up the tab?—you can often determine what a long-term relationship would look like.

Brown-Volkman has another suggestion: Draft up a list, with your current position in one column and the new job in another. Then compare certain factors side-by-side, like benefits, salary, commute, schedule, and responsibilities.

Step #4: Evaluate What it Would Cost You to Stay in Your Comfort Zone

One particular challenge facing “lifers” is that you lose marketability. After 10 years or so in the same job, recruiters start penalizing people for not being more ambitious, assuming your skills are stagnant and you lack motivation.

And while money isn’t everything, becoming a barnacle usually means you aren’t scoring the raises that occasional job hopping can net.

“Periodically, it’s worth investigating what you’re worth in the marketplace—and if you’re underpaid—by going on interviews, talking to recruiters, and checking out websites like,” says Eleanor Blayney, a CFP® and consumer advocate for the Certified Financial Planner™ Board of Standards.

Blayney estimates that a 30-year-old currently earning $45,000, but who could be making about 10% more in a new position, potentially gives up $500,000-plus over their work life by staying put. This takes into account not only lost salary but also lost 401(k) matches and lower Social Security benefits.

On the flip side, that long tenure in your current job has likely earned you perks that can be hard to let go of, like ample vacation time or stock options. But there’s no reason why you can’t negotiate for similar benefits with a new employer.

Just try to keep your asks to a maximum of three, Youngquist says. ”And remember that you already have a decent job, so you need a compelling reason to leave,” Brown-Volkman adds. “You have nothing to lose.”

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