I almost left a great job because I didn't know to ask these 4 questions before calling it quits

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I almost left a great job because I didn't know to ask these 4 questions before calling it quits
Shana LebowitzCourtesy of Shana Lebowitz
  • Shana Lebowitz Gaynor almost quit her job at Insider.
  • She ended up having an honest conversation with her boss, which was pivotal to finding happiness in her role.
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Several years ago, I felt so frustrated at work that I considered quitting my job at Insider.

My managers kept assigning me slideshows on topics like signs that you're likable or that your relationship is on shaky footing. They weren't always my favorite stories to write, and our audience was seemingly losing interest in some of them. But instead of raising the issue with my editor, I started looking for other jobs.

I almost left a great job because I didn't know to ask these 4 questions before calling it quits
Don't Call It Quits: Turn the Job You Have into the Job You Love by Shana Lebowitz Gaynor.Courtesy of McGraw Hill

Fortunately, the search didn't pan out. I ended up having an honest conversation with my boss, which led to a change in my assignments — and that led to me feeling happier and more satisfied in my role. I was lucky.

It's easy for me to say now how I could or should have handled this dilemma. One thing I did learn is that before making any changes to your work experience, it helps to gain some clarity around what's going well and what's not. A coach, or even an especially thoughtful friend, can assist in this process.

You can also lead the introspection process yourself, using the following questions as a guide. Answer them honestly, either in your head or on paper — and be open to surprises you may learn about yourself.

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1. What are your favorite parts of your current workday?

Think back on how you spent the last workweek: Were there any times when you felt more engaged or motivated than usual? Even a fleeting half hour counts, and no one will fault you if the source of happiness was checking your inbox for new emails.

It's critical to identify these less-loathsome parts of your work experience and how exactly they made you feel. For example, maybe chatting with a longtime client on the phone brought you some joy yesterday.

If you stay in your current role, you can work on finding ways to make certain client interactions a bigger part of your workday. Even as you start plotting your next career move, knowing what you value in a job will help you target your search — and avoid winding up in a similarly frustrating situation in your next role.

2. When during your career have you felt most engaged?

I'm using the word "career" here, but any work or academic experience counts. Try to recall the details: what you were doing, where you were, who else was there.

This is an exercise that the career coach Rebecca Fraser-Thill uses often with her clients. It's especially useful, she said, for high achievers who are accustomed to looking outward for signposts of success, like promotions, raises, and praise from management; the question helps these individuals shift their focus inward.

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Don't get too literal — just because you enjoyed tutoring in college doesn't mean you should pivot from consulting to teaching. Instead you'll want to drill down until you can say (or at least guess) what about that experience was so gratifying. Even better if you can remember a few instances and try to find the common threads between them.

3. What might that gratifying experience look like now?

Say you realize that you get a thrill out of seeing people's faces light up when they make progress on a tough challenge. If you were one of Fraser-Thill's clients, she'd ask you how you might replicate that experience or elicit that thrill today in your current role.

Be as creative as possible when you brainstorm. Maybe you could spend more time working on-site with clients and rolling up your sleeves to help them solve their trickiest problems. Or volunteering to present an area of expertise that you have, but people on your team might not have.

There are many different paths to the same emotional outcome. And sometimes just knowing that you have those options can help you feel a little lighter, even before you execute on any of them.

4. What are the 3 most important attributes you bring to a work environment?

These can be anything from a positive, can-do attitude to the ability to focus your attention on a particular project for hours at a time. Being able to articulate your most important professional skills can help you find or create a work environment where you'll thrive: Research suggests we're most engaged at work when we're capitalizing on our unique strengths.

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This exercise can have powerful implications. First, simply knowing that you're someone who brings something special to your work environment can help you build confidence. And instead of feeling demoralized because this job is completely detached from what you care about and enjoy, you can train your attention on whatever aspects of the job you do feel connected to or uniquely skilled at. Remember, you need to be able to articulate your skills and passions before you can begin to appreciate the parts of your job that draw on those things.

It's easy — too easy — to fall into a pattern of hating your job, assuming it's your boss's or coworkers' fault, and resigning yourself to the fact that there's nothing you can do about it. In some cases, this may be true. But in some cases, it's not. And it's worth figuring out which one of those buckets your experience falls into.

Shana Lebowitz Gaynor is a correspondent for Insider, where she covers career development and workplace culture.

Adapted with permission from the book Don't Call It Quits: Turn the Job You Have into the Job You Love by Shana Lebowitz Gaynor. Copyright © 2022, McGraw Hill.

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