Dear Businesslady: A Garden Of Job Advice -The Toast

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

Greetings, Toasties!

Dear Businesslady has been around for long enough that I’ve accrued a robust backlog of unanswered letters, and a lot of them present issues that seem to have pretty straightforward solutions. Leaving them unpublished feels like a violation of my advice-giver mandate—and it’s starting to make me feel guilty. (You know that thing when an old friend writes you a “let’s catch up!” email, and then you take so long to respond that you feel like you’d have to write a Tolkien trilogy to justify the delay, and then that burden seems so overwhelming that you just never reply at all, and you hate yourself? It’s kind of like that.)

To clear both my inbox and my conscience, here are some shorter answers to (somewhat) simpler questions. If you have alternate takes to any of these scenarios, feel free to weigh in via the comments.

I’ve never written to an advice column before, but my coworker has me stumped. We work together well and get along with each other on a personal level. We are also the only two people who report directly to our boss.

Since I started, I have noticed some possessiveness, for lack of a better word, on the part of my coworker. It seems like she wants to 1) be best friends with our boss and 2) make sure everybody knows she is better friends with our boss than I am. She makes regular, pointed comments about how the two of them have such similar tastes, similar temperaments, similar senses of humor, similar working styles, etc. She talks about her opinions of our boss’s friends and family and is always sure to remind me that I don’t know them as well. I could go on.

I find this very confusing because truly, from the bottom of my heart, I do not care. I like them both, but I am not trying to be best friends with either of them. I don’t feel that I am really doing anything to compete besides, you know, existing. My strategy so far has been to stay the course and try not to bring up our boss any more than is strictly necessary. However, the competitiveness has increased steadily (and, in my mind, inexplicably) over the last two years, and I’d just really like to put an end to it if at all possible. What do you think I should do?

Ooh, I wish I had a magic bullet for this one, because I think you’re already doing everything right: staying out of the drama as much as possible, not letting it get to you, and recognizing it for the nonsense it is.

This clearly stems from some kind of insecurity on your colleague’s part, and in my experience calling people on their insecurities does little to dismantle them. That said, you could still try to sit down with Weirdly Possessive Coworker and talk about it directly—and if you approach it from an angle of “hey, this constant referencing of your soulmate status with Boss is weird for me,” you might have some chance of success.

Of course, that requires framing things such that you’re the one with the problem, and that may be tough to pull off.

Another option would be to start making good-natured jokes about it (which might help you blow off steam and feel less irritated). Coworker: “did you know that Boss and I are both water signs?!” You: “yes, clearly you were preordained by the universe to one day be her employee.” But then again…I may not be the best judge of what a “good-natured joke” is. The success of this method depends on your ability to carry it off in a truly lighthearted way and not sound like a dick—the last thing you want to do is to rile up your coworker even more and make things worse.

I feel for you, because this sounds maddening. Ultimately, though, it might be one of those annoying workplace conditions you just have to live with—and if either of the above strategies sounds like a nonstarter, that’s probably the best way to go.

*        *        *

I’d like to move back to my home state, and to that end I’ve been looking at open jobs in my field. My father is urging me to call the mother of one of my high school classmates, who is some sort of bigwig at a college in my hometown, and ask her to provide a personal recommendation for me. “She likes you. She always asks about you. She has followed your career with interest,” my father insists.

I haven’t seen or talked to this person or her daughter in at least twelve years. Quite apart from my reluctance to ask favors of someone to whom my connection is so tenuous, could her recommendation (based on what? my performance in The Caucasian Chalk Circle when I was 15?) possibly do me any good?


Frustrated Daughter

I like this question because you and your dad are both a little bit right and a little bit wrong—and if your family is anything like mine, maybe you’re not super adept at seeing nuance when it comes to intergenerational disagreement.

You’re totally right that a “recommendation” from this vague acquaintance would be absurd. Most employers don’t want personal endorsements as it is—they want to talk to people who’ve actually worked with you and know what you’re like in a professional setting—and they definitely don’t want to hear from people who haven’t interacted with you since you completed puberty.

But at the same time, I think your father is onto something here, and I suspect that your knee-jerk “oh my god, Dad, no” reaction is blinding you to it.

If this local bigwig is still in touch with your family and genuinely interested in where you’ve ended up, that’s a connection you can use to your advantage. Get in touch with her and explain that you’re starting a job search in your hometown (amid other “how’ve you been”/“how’s your daughter doing” pleasantries, of course). Give a quick summary of your background and the type of role you’re looking for and ask if she knows of any leads that might be viable. Colleges and universities employ a lot of people, so the odds are good that she might have some suggestions. Plus, “Important Person tipped me off to this opening” is a great thing to include in a cover letter.

Depending on how warmly and enthusiastically she responds to this initial contact (and how relevant her position is to your own field), you might also consider asking her for an informational interview—but if you do meet up with her or set up a phone call, make sure you have actual substantive questions to ask beyond “how can I get myself employed?” or “how can I be successful like you?”

Basically, don’t pass up a prime opportunity for networking (which is basically a gross, businessy word for “letting the people you know help you out”) just because it came packaged in an off-base parental suggestion.

*        *        *

I have a Finance/Accounting Analyst position with a large company that I have been with for almost three years. I currently like the work I am doing but my role has recently increased to include another person’s role (who was a level higher than me and made about $30k more) and there seem to be more increases in the horizon. Throughout these changes, my boss has been fantastic. I have such a great amount of respect for him and he is especially appreciated after I had a revolving door of bosses in my previous role with the company.

Despite the fact that I love my boss and my work, I don’t think it is fair for me to being doing more work for the same pay and which is a situation that seems to occur often in the company. Because of this, I have been testing out the market and will be ready to leave if the right opportunity comes along.

The problem: The person I backfilled quit abruptly right before the busiest time of the year and it put a lot of strain on my department. That time of year is coming up again and I have some good prospects for leaving, one that I would consider a dream job. How do I handle this with my boss? I don’t want to place him in such a bad situation but I know I need to make the best decision for my career.

Since you really love your boss that much (and it sounds like you have a good relationship with him), you could let him know that you’re on the way out. If there’s any chance of the company giving you a raise/change of title to reflect all the extra work you’ve been doing—and if you’d be interested in sticking around under those conditions, which is key—then that gives you the license to say “hey, I tried to stay” no matter how things play out.

But, c’mon—you know what I’m gonna say here, right? Quit. Your. Job.

I mean, seriously: it’s just a job. If you’ve got something unequivocally better on the horizon, or you know that they’re already paying you all they can, or you’re already so burned out that even a fafillion more dollars wouldn’t change things—then go for it. Your boss and coworkers might be extra swamped for a while as a result of your departure, but so what? Other people’s workloads are less important than your overall well-being.

*        *        *

I finished a Master’s degree last year, and promptly left the country to go travelling. It has now been 18 months (I haven’t been travelling the whole time, but haven’t been working either. Yup, I know I’m pretty lucky, nope I’m not rich, it’s complicated) and I am in the process of moving back home and looking for work.

All of the advice I’ve found with regards to returning to the workforce has been for returning mothers. Which is good and all, but doesn’t work for my situation, as the advice usually assumes a stable place of residence (nope) good integration, i.e. contacts with the community where you wish to work (nope) and previous full time work (nope).

Do you have any advice for a 20 something with a humanities degree, a pretty ok but old part-time job history, and a significant recent gap in her CV?

You’re in a bit of a tough spot because you’re basically starting from scratch in terms of your job search (education and work history notwithstanding). But I don’t think a resume gap of less than two years is going to hurt you that much, particularly when it follows on the heels of a graduate degree. And the good news is that entry-level full-time jobs are a thing: once you’ve landed your first position, you’ll be well on your way to building a more long-term career.

If you’ve got a humanities background, that should mean you’re at least a halfway decent writer, so let the cover letter be your savior here. That’s the place where you can (briefly!) explain why you haven’t been working recently, and it’s also where you can narrate your work history in a way that aligns well with the positions you’re applying for. (More on this here.)

Also, just because you don’t have a local network yet doesn’t mean you can’t quickly establish one. As soon as you’re fully settled in your new area, start making friends. Maybe so-and-so’s former boss needs a freelancer, maybe someone else has a cousin whose cool company is hiring, maybe there’s a powerful family friend your dad’s been hounding you to contact (ha)—even if those leads don’t pan out, you’ll be developing contacts in your new community and practicing your job-search skills.

That’s not to say that getting a job is easy—but it takes perseverance and patience no matter how “perfect” your resume might be. And my inbox is (still!) full of letters from people who are in a very similar position, so rest assured that you’re not alone.

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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