Shana Lebowitz.
Courtesy of Shana Lebowitz
Shana Lebowitz grew frustrated with her work assignments.
She prepared to quit her job, taking meetings for other opportunities.
Lebowitz found that sharing feedback with her manager was enough to make her job enjoyable again.
A few years ago, I almost left my job at Insider.
In retrospect, it’s easy to say this would have been a ridiculous idea and to remember all the wonderful, redeeming aspects of my work experience at that time. But I know I must have been feeling frustrated, confused, and stuck.
At the time, I wrote about self improvement, especially as it related to work and careers. For the most part, my job was interesting and a lot of fun. I read books about productivity and time management and distilled the most compelling takeaways into short articles. I wrote about my experience adopting the daily routines of successful and powerful people like Tim Ferris and Donald Trump. (Spoiler: Waking up at 5 a.m. to watch the news à la Trump is decidedly not for me. But getting to work at 11 a.m. after slowly drinking tea and meditating à la Ferris really could be.)
But I was also responsible for publishing slideshows featuring signs that you’re likable or that your relationship is strong. Insider published many slideshows in this vein; they were clever and appealed to readers’ curiosity — but they weren’t always my favorite stories to write, and our audience was seemingly losing interest in some of them.
Editorial leadership, however, still found value in these stories and continued assigning them. I’d grudgingly accept, even when I knew I’d rather write more in-depth stories, say, features about entrepreneurship or analyses of new research on gender dynamics at work — stories that would make better use of my own curiosity and my interest in making readers think differently about their careers.
All this was happening shortly after I’d gotten married. Now that the harried months of choosing caterers and bands and bouquets were behind me, I had a little more energy and space on my calendar. So I applied for a couple of different roles elsewhere and set up some networking coffees with acquaintances who worked at places I’d like to write for. Nothing ended up panning out — fortunately, because it was around that time that things changed for me at work.
McGraw Hill.
Courtesy of McGraw Hill
A reporter on my team interviewed an executive about her favorite interview questions, one of which was, “What are the best and worst parts of your current job?” The woman who was my editor at the time is an exceptionally curious and compassionate person, and after publishing that reporter’s story, she messaged everyone she managed, asking each of us to describe the best and worst parts of our job at Insider.
It was easy to tell her the best parts of my job, but I remember my hands hovering over the keyboard, wondering how honest to be about the rest. Ultimately, I wrote that I didn’t always enjoy publishing those “signs” slideshows because they only skimmed the surface of important topics, and that readers might not be crazy about them either.
My editor wrote back almost immediately: She’d take these comments into account when generating assignments.
Reader, I never published another one of those slideshows again.
This situation could’ve worked out much differently for me
Maybe I would’ve landed one of the jobs I’d applied for before my editor even had a chance to ask these questions. Or if I’d had a different type of editor, maybe she wouldn’t have asked these questions at all, and I’d never have articulated my concerns, meaning I’d have stayed annoyed and resentful. Or maybe the assignments I was resisting would’ve been critical to my job, and I’d have had to choose between doing them or leaving.
In many ways, I was lucky. But what’s clear to me now is that there are so many more productive ways I could’ve approached my own discontent. Here are 4 things I might’ve done differently.
1. I could have gauged the culture on the team
This means asking yourself, “Do I have the kind of manager who would be receptive and even supportive if I told her I didn’t like some of the work I was doing?” For some people, the answer might be absolutely not, in which case complete candor might not be the best approach. (Better to focus exclusively on the measurable outcomes these tasks are or aren’t driving.)
But in my case, the answer was yes — meaning there was something other than the fear of upsetting her that was behind my reluctance to be straightforward. I suspect that, on some level, I feared the editorial powers that be wouldn’t think I was skilled enough to start writing more of those feature stories, or that they’d turn out to
be really boring. It was arguably easier to just complain about not having the support and encouragement I needed.
2. I could’ve explained how doing things differently would benefit the organization
Another thing I did reasonably well, but could have done better: Framing my resistance to “signs” slideshows and my desire to do something else. In the email response to my editor, I said that these stories weren’t performing so well with readers. But I could easily have gone a few steps further.
Perhaps I could’ve dug up statistics on slideshows that had flopped and compared them with the stats for other articles that readers had gobbled up, then figured out what made them different. Perhaps I could’ve pitched an alternative story idea for every slideshow I published that would have gone deeper into the very same topic.
The point is this: When you’re talking to your boss about dropping some of your job responsibilities, you’ll want to be as specific about why and as proactive as possible about what else we can do. It’s a way to show you’ve taken ownership of your role — something many execs have told me they love to see in their employees. And when you come prepared with data and ideas, your manager will have what’s needed to approach their manager and make the case for you to shift your projects.
3. I shouldn’t have assumed my boss knew how I felt
Most importantly, I could have realized that my editor, however savvy and sympathetic she was, was not a mind reader. If I didn’t tell her how I felt about certain assignments, there was virtually no way for her to intuit this information.
4. I should’ve given myself options
There’s nothing inherently wrong with scouting out new opportunities and seeing how they compare with your current role. Netflix, in fact, encourages employees to interview for jobs outside the company and then talk about what they learn with their boss. Talking to someone who isn’t your direct manager at a job you dislike can help you gain some clarity around the kind of work you’d prefer.
But moving elsewhere shouldn’t have been the only option I was banking on. Other options included talking to my editor about my observations and ideas and seeing if, together, we could reshape my role.
In fact, there’s a chance that if I did get one of those other jobs I’d applied for, I might have found myself in the same predicament of getting assignments I didn’t like and still being hesitant to say anything about it … which is to say that even if ultimately you do leave your current job, the process of identifying what’s valuable and what you enjoy can help you target your search for your next opportunity.
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.