Dear Businesslady: Job Advice For Career-Building and Feedback -The Toast

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Email us questions at, subject line “businesslady.” Previous installments can be found here.

Dear Businesslady,

Should I stay with a stable, rewarding part-time job in the field I hope to get into or leave it to pursue greener (and more fun) pastures? Some context: I am 21 and will be graduating with my bachelor’s degree this June.

I am currently working at a part-time job in my college town I feel VERY lucky to have. I’m writing for a company that’s related to the field I think I want to get into, my boss is amazing, I’m learning and enjoying myself (and for an undergrad, I am very well paid). I’ve been working there since October 2014.

My dilemma, though, is what to do when I graduate.

Before I was hired at my current job, my plan was to spend the summer working in a national park and then take some of my earnings and travel. I love being outdoors and I’ve had friends who did that and they loved it. I wanted to have one last fun summer and travel a bit before I settled down and looked for real work.

In her twenties, my mom found herself in a job and town she disliked because the money was decent. Shortly after she finally left that job, she became disabled and unable to work. She regrets spending the time where she had good health doing something she disliked. She has warned me about the “golden cage” of a shitty job. She says once I’m in the work world, I will lose my motivation to travel and spend the summer outdoors, that it will feel like a good tradeoff at the time, but I will look back to regret it.

Should I stay in my college town and keep working at my current (part-time) job? Or quit so I can have a fun summer and travel? I literally get teary when I think of how much I want to work in a national park, but I feel like it’s more sensible to stay at my current job and keep building my resume. I haven’t been working there very long, after all. I feel so young and I don’t feel ready for a career. But maybe its time to grow up.

What do you think?

Dear Green,

First off, thanks for making it so easy for me to give you a nickname. You’re young (green), you’re thinking about greener pastures, and you’re yearning for the verdant embrace of a national park.

In some ways you’ve given me an easy question to answer too, except it’s not actually that simple. So let me tell you a story.

When I was little, I used to love visiting my dad’s “office”—the quotation marks are to denote that it was one of many cubicles in a massive complex; he had an unglamorous corporate job working for a multinational company. Some of the decorations in his space weren’t interesting to a grade-schooler, but I remember being fascinated by a phrase he had framed and hung behind his desk: “Never become too good at something you hate. They’ll make you do it the rest of your life.” (There’s a bizarre story behind that quip, but that’s neither here nor there.) And in many ways, my dad actually did become too good at a job he hated; he spent most of his professional life doing things he didn’t particularly enjoy—although at least he was self-aware enough to snark about it via his cube décor.

I still love that quote, but as a kid I responded to it with a kind of fearful awe: Who are they? How would they make you do something you hated? And how could you become “too good” at something you hated anyway? When you’re young, you hate things like getting vaccinations and you love things like playing with toys. You don’t yet have the capacity to comprehend how the double-bind of material comfort vs. personal satisfaction could leave you trapped.

That phrase was my first indicator that “what do you want to be when you grow up?” was actually a pretty loaded question.

Of course, my career path, like most people’s, isn’t a straight line toward work-life balance and contentment. There was a time when I viewed that quote as wholly ironic: that the only way to be successful is to find your own well-compensated-but-loathed skillset and then hang on until retirement. Before that, “when I was your age,” I saw it as more of a commandment: don’t pursue any job you don’t love!

Nowadays, I’m a realist. Everyone makes their own cost/benefit calculations based on the options available to them, and those options are bounded by a whole host of factors, both within and beyond their control. Those of us who are lucky enough to attend college inevitably have to check our pre-graduation idealism against the harsh realities of the post-college world—and for all I know, you might one day regret leaving your rewarding job that aligns with your big-picture aspirations.

Nevertheless, I think you need to let this dream play out and make your peace with the possibility that hindsight might make you see things differently. You’ve got a mom whose personal history is an object lesson in seizing the moment. You’ve got a solid work history in your maybe-future professional field before you even get your diploma (to say nothing of the fact that you’re going to have a college degree, period). You’ve got involuntary emotions welling up when you think of how badly you want this. And, finally, your big idealistic goal isn’t “surpass Beyoncé in record sales, fame, and fabulousness” (which I would strongly discourage you from attempting to achieve)—it’s “try out a different job that may not have as much long-term potential” and also “travel.” At 21, you deserve to give that a shot.

Let me stop waxing introspective about Life ChoicesTM and conclude with some more concrete advice. Since you have a long and positive history with your current employer, give them as much notice as you possibly can—as soon as you have a viable plan in place for your summer of outdoorsy adventure, sit down with your boss, express your gratitude for all the opportunities they’ve given you, and explain that you’d never forgive yourself if you didn’t take advantage of your postgrad freedom. (Caveat: don’t do this if you think they might do something retaliatory like fire you on the spot, but it doesn’t sound like that kind of gig.) The idea is to make sure they give you a stellar reference from here on out—plus, being classy about your departure leaves open the possibility of getting rehired or thrown some freelance work in the future. Following your passion doesn’t mean you have to be careless about it.

But don’t make the safe choice just because you’re not sure what lies on the other side. You don’t want to be stuck in that golden cage for the rest of your life.


Dear Businesslady,

A few months back a subconsultant whom I would have gladly sacrificed most of my office for was unexpectedly let go. She was shocked, she was given no warning and no one had said anything negative to her about her work. Others on the project were also shocked and have been asking managers about this decision. The reasons filtering down to us have all been understandable (she didn’t review her work before submitting it, didn’t followed the chain of command), but were all things she could have worked on if someone had talked to her. No one did, and I am wondering now if I should. Would if be appropriate for me to take her out to lunch and discuss what led to her being let go? I feel it’s not really my place; but if no one tells her any of this she may repeat mistakes. I want her to succeed and do well, and I think her having a better understanding of what went wrong may help with that.

Missing My Coworker

And a little bit of background if you are curious: [Possibly identifying details regarding complex job requirements redacted.] People like her who could do it all are gold.

Dear Missing,

And now it’s time for me to thank you, for giving me the truly easy-to-answer question I needed after spending so much time pondering the cruel mistress that is a human life/career trajectory (and I didn’t even have to come up with a nickname for you, either).

In a word, YES!

Okay, I’m still way too verbose to just leave it at that. Let me commiserate—I know from personal experience how awful it is to watch a beloved colleague lose their job, especially when that person was never given a real chance at saving it. I also know how painfully awkward it is to point out the spinach in someone’s teeth, particularly when that spinach is metaphorical and the actual issue is much more sensitive.

But the worst-case scenario here is that your ex-coworker takes your attempt at mentorship terribly for some reason: maybe she yells at you, or gets super defensive, or takes it as an opportunity to delineate what she perceives as your professional flaws.

Even if that happens, so what? You don’t work with her anymore, and while that would be an unpleasant experience it would almost certainly mitigate any misgivings you had about your management’s decision to let her go.

And that kind of negative reaction is pretty improbable. More likely, she’ll be thrilled that someone from her old job saw her value, and she’ll be deeply grateful for the opportunity to avoid making the same mistakes elsewhere.

I’m especially emphatic about my “yes” because the things she needs to work on—lack of proofreading, poor adherence to hierarchy—are pretty concrete and easy to fix. If the problems were more vague or difficult to address (like if she seemed off-putting in some ineffable way or had intractable halitosis) I’d probably still encourage you to talk to her, but with tempered expectations about your chances of success.

How many of us learned far too late about some stupid thing we were doing, just because everyone around us was afraid of a difficult conversation? You want to give this colleague a gift, and I don’t want to live in a world where people like you don’t speak up.

Plus, who knows—if her talents really are that rare, maybe you’ll end up working with her again once she gets her shit together. Don’t you want to increase the odds of that happening someday?


P.S. To anyone on the receiving end of this kind of hard truth, consider it your civic duty to not shoot the messenger. I, for one, would rather learn about the spinach in my teeth at the dinner table, instead of when I get home from the four-hour cocktail party afterward.

Businesslady is in her early 30s and somehow managed to find a rewarding career despite her allegedly useless degree in the humanities. Her job history includes everything from food service to retail to corporate nonsense, but she currently does writing and editing for a nonprofit, and devotes the rest of her life to playing video games, patronizing bars, and spending way too much time on the internet.

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