Not All Bosses Are Evil (Said a Boss, Nervously)

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Send questions about the office, money, careers and work-life balance to workfriend@nytimes.com. Include your name and location, even if you want them withheld. Letters may be edited.

I worked for a large corporation for 14 years and found myself stuck and uninspired — logging in only to collect a paycheck and waiting for the weekend. I wondered how some people advanced their careers seemingly effortlessly, while others with equal mastery, intelligence and dedication made less headway. After a shocking layoff wake-up call, I went full force on networking and landed a job that I think is my true calling. But I can’t seem to escape a comment made by one of the directors I interviewed with, who said, “There’s no such thing as a perfect job.” How valid is this statement?

— S.P., San Diego

Hello, I’m your new work friend, here to help you solve picayune workplace dilemmas like “Jerry keeps hogging the printer,” “Maya mass-emails bad memes” and, uh, “Can the nature of labor ever be good?”

My primary qualification to answer at least some of these is that I’ve had a lot of jobs. I work in the healthy, thriving media industry, so I’ve been laid off multiple times and have interviewed for dozens of positions, several of which never wound up existing and several more of which didn’t outlive my tenure. Not unrelatedly, I am the first millennial author of this column, which means that finally, your work friend will know exactly whom to blame for your economic precarity and terrible office habits: boomers.

I’m also a boss — I run a team of 20ish writers and editors at the sports magazine Deadspin — and my major takeaway from early interactions with the workfriend@nytimes.com inbox is that everyone hates bosses. They micromanage, they sabotage your career prospects, they lay you off, they talk too loud. Let’s see whether 13 weeks of answering your questions makes me feel smug that I don’t do any of those things or paranoid about all the reasons my employees surely hate me!

To get to your question: I’m pretty sure the only things I have ever earnestly described as perfect are my pug’s face and a plate of oysters on a 72-degree day in Seattle. So, no, I don’t think any situation in which a corporation controls your day-to-day life can ever be truly ideal. (I do think a hiring manager saying as much in a job interview is a terrible recruiting strategy and quite possibly a red flag, but let’s set that aside for now.)

But nor do you have to settle for a job that makes you miserable just because you’ll never find one that fulfills every dream. Threatening to quit every time you suffer a minor indignity is overkill, but if you’re truly suffering for 40 hours a week, you have my full blessing to bail. Assuming you got some severance, getting laid off from a job in which you felt stuck and uninspired seems like a stroke of luck. And while any new commitment requires a leap of faith, any job that feels like your true calling is one worth trying.

Some people will always have an easier time in the work force because of luck and timing and bosses’ prejudices, and your job will always let you down sometimes. But don’t let the world’s inherent unfairness and the boomers’ destruction of the economic system break you of your desire to have a moderately enjoyable work life. Just promise me you’ll consider getting a dog, or a dozen ice-cold kumamotos.

I recently started a new job in a new field. As I approach the three-month mark, I know the how’s-it-going conversation is coming, and I find that I’m really not liking the job. The hours are not a good fit, and the territory involves more early-morning long drives than they let on. I am also interacting with high schoolers daily, and I’m beginning to really dislike that aspect of the job.

Maybe it’s just been a bad week, but I’m feeling more and more like this isn’t the job for me. What should I tell my boss? The truth, part of the truth or none?

— Teaneck, N.J.

You’re the rare letter-writer who doesn’t say explicitly that your boss sucks, so what if a how’s-it-going conversation means your boss genuinely wants to know how it’s going? ’Fess up to your mistaken assumption that you’d enjoy working with students, tell the truth about not expecting so many long drives in the wee hours, and highlight any parts of the job you actually like. Maybe your boss has an idea for tweaking your responsibilities — or maybe you’ll both agree it’s not a fit and you can leave on good terms.

Disgruntled employees make for giant headaches, so your boss has an interest in making you happier. Few people would fault you for leaving a job in a new field relatively quickly once in your career, but make a good-faith effort to fix it before you run screaming.

I am a junior in college with three part-time jobs: one in food service, one in the dean’s office and an internship at a record store. At the food job, I was recently promoted. Almost immediately afterward, my internship supervisor told me he wanted to hire me on. I planned to work all three jobs over the summer, then quit serving food so I don’t go crazy during my final year of college.

As the summer grows closer, though, I keep tiptoeing around the idea of quitting earlier. I don’t want to upset my bosses, but I want to be able to enjoy my summer. I keep telling myself that the promotion would look great on a résumé and show loyalty. However, what I really want to do is work in the music industry, so the record store would allow me to make connections while actually enjoying my job. Is it worth it to take the promotion?

— S.W., Bloomington, Ind.

Nobody who can afford to work fewer than three jobs should ever work three jobs — especially college students, who should be staying out late and making questionable decisions. And earning a promotion through your own hard work doesn’t obligate you to stick around. Quit the job, make the most of your time at the record store, and live a little during senior year before you grow old and grumpy and tired like the rest of us.

Megan Greenwell is the editor in chief of Deadspin. This column rotates quarterly; write to her for the next 13 weeks at workfriend@nytimes.com.

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