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

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

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

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