Dear Businesslady: Advice On Guilt and Job Loyalty -The Toast

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

Dear Businesslady,

I work in a small office that has seen a lot of turnover in the past 8 months. Half the staff has moved on to other jobs and we’re still working on filling some of the open positions.

I have become the most senior staff, which is scary because I have been on the job for less than three years, but in comparison to the new staff, I have sage-like wisdom of institutional knowledge. This has meant that I have been deeply involved in familiarizing new staff with our work in spite of the fact that none of them are my direct reports.

My new coworkers are great and I enjoy working with them, but the organization is still a ways away from solving the cultural issues that lead to the mass exodus. And now I want to continue that exodus but feel extremely guilty about it.

I am among the final candidates for new job that would come with a 20% raise over my current salary and probably a healthier office culture, but it would definitely be kinder to my colleagues if I stayed.

There are still certain processes that only I know how to do because there hasn’t been enough time to train the new staff on them. I am slowly documenting all the necessary processes, but worry that I would forget to put something in the documentation and then screw over whoever has to take over those tasks.

If I get offered the position at the other company, I would need to start as soon as possible. However, at my current job, my coworkers and I are working on a project that will take another 5 months to complete. Not an ideal time to leave, but openings in my industry can be few and far between. And I’d be lying if I said money wasn’t a motivator. I am pretty underpaid and I hate that it bothers me, but it does.

Would it be a total dick move to leave my team in this time of relative turmoil?

-Selfishly Seeking Transition

Dear Selfish (Who, Spoiler Alert, Is Not Actually Selfish),

There are a couple letters like yours in my queue of questions, so this seemed like as good a time as any to give you all a pep talk about the complicated emotional dynamics of job-searching and organizational loyalty.

The closest thing I have to a unified theory of life and human behavior goes something like this: you’re either worried you’re part of the problem, or you are part of the problem. This isn’t limited to the professional realm, but it’s particularly applicable in that context—all the most productive and responsible people I know are constantly fretting: Is their work good enough? Are they pulling their weight? Are they unwittingly making their colleagues’ lives miserable? (I count myself among that group; my mental state is basically in a constant pendulum swing between 75% “this is it; I’m finally going to get fired” and 25% “goddammit this place would practically burn to the ground if I weren’t so awesome at what I do.”) By contrast, the real Problem Coworkers—the ones who are constantly behind deadline, always asking huge favors with zero recognition of the imposition, never at their desk when you need them—they never seem to even realize that they’re That Guy.

So what does my unified theory have to do with your situation? Well, if you’re worried about screwing over your old workplace, that means you can’t possibly screw over your old workplace for real.

I absolutely believe that your departure, if it happens, would come at an inconvenient time for your office. But the thing is, there’s never really a good time to leave a job—not if you’re a valued employee, anyway, as opposed to someone everyone’s secretly hoping will move on. Turnover is always disruptive, and even if it happens when things are slow, that can present issues too (what if your replacement can’t hang once it gets busy, but it’s weeks or months before that becomes apparent?).

I’ve been on the other end of many “I got a new job and I’m GONE” announcements, and I’ve reacted to some of them with the mixture of dismay, envy, worry, and frustration that you’re surely expecting from your coworkers. But you know what? It takes a huge amount of effort for me to conjure up those feelings after the fact, and I never think ill of my former colleagues whose departure made things inconvenient for the rest of us. Sometimes it’s rough for a while; sometimes it works out more smoothly than you could’ve anticipated—but either way, there eventually comes a time where the post-coworker reality becomes the new normal, and even the long hours and stressful transition periods fade into the fog of memory.

It’s great when you’re emotionally invested in your job and have real fondness for the people you work with, even if the flipside of that means that you can’t just blithely ride off into the sunset as soon as something better comes your way. But your coworkers will deal—and if you’re being thoughtful about leaving them with as much support as possible, they’ll remember you fondly as they adjust to your absence. Plus, if the issues at your organization are as systemic as your letter suggests, your defection might end up helping them in the long run: arguments like “we can’t keep good people like X because of our terrible track record with Y” can often help higher-ups take employee complaints more seriously.

These types of decisions become trickier when the new gig is a dubious improvement over your current job—if you’re worried that you’ll regret the change, that introduces an added complication. But the combo of better-culture/higher-pay makes this a no-brainer. Go forth and take that new job with my blessing—and if it doesn’t work out, keep searching until you find something that does.

*        *        *


Hi Businesslady,

My boss is retiring at the end of next week after over 30 years of working at my University. Our administration said nothing to us about what to expect when she retires until today, an hour before the boss’s retirement luncheon. My current job requires that I have a thorough working knowledge of the complicated software system we use, and ever since she announced her retirement, the other people in my department have been coming to me with issues that they need resolved, basically treating me like her successor. The boss even told me that she identified me as the most qualified person to take over for her.

I think you can probably guess that today, an hour before my boss’s luncheon, the admin announced that someone else — someone with no experience using the software and no management experience– has been appointed interim head of the department. This person has been here the longest of any of us that remain and she also has tenure, which I am working on but do not have yet. She is also the least collaborative of any of us and other departments do all they can to avoid working with her.

My approach to being a professional thus far can be best summed up by: “that’s not in my job description is my most hated phrase in the English language” but I am already practicing it, balking at the idea of helping her learn the system when we come back from break in January because I feel passed over. Do you have any advice about the best steps to take to get back to my positive, team-motivated attitude?


Spiteful Suzy

Dear Suzy (I Refuse to Call You Spiteful),

I chose your letter as a companion to the one above because you’re dealing with a worst-case scenario of being the Left-Behind Coworker. But my “there are two kinds of people” theory is relevant here too: you’re not asking how to get revenge on your workplace for putting you in such a shitty situation, you’re asking how to adjust your attitude so that you can continue being good at your job. The fact that you have that perspective makes me pretty convinced that your “resentful” is closer to other peoples’ “chipper and agreeable”—and also, I wish I could give you a hug.

But presumably you didn’t write in just so I could express admiration for you, so let’s see how we can solve this.

As a first step, it might be useful for you to approach the admin who seems to have been behind this interim appointment and see if you can glean some of their reasoning. It will be essential for you to remain emotionally neutral during this conversation, but if you can manage that—and I bet you can—understanding the broader context might help you feel less slighted by the decision. The fact that your departing boss had tapped you as a replacement provides the perfect opening for that discussion: it’s natural for you to be curious about their rationale when the results contradict what you were told.

There could be some strategic reason to putting an unskilled, combative person in charge (maybe it’ll support a request for additional staffing further down the line); they might be trying to protect your time as an untenured faculty member (despite recognizing that you’re far better-suited to the role); they could be anticipating some future events where your colleague’s experience will outweigh her shortcomings (up to and including a complete overhaul of the software system that’s currently causing the friction). Or it could be any number of other things I couldn’t randomly think up as an uninformed external party. Even if the response is “oh, snap, we totally didn’t think about how much better it’d be with you in charge,” at least then you’ll know where they’re coming from (in this case, a position of short-sided ignorance, but hey). And ideally, knowing that some reasoning went into their decision—even if it’s reasoning you don’t ultimately understand or agree with—should help work against the They Specifically Picked Not-Me narrative that’s currently (and justifiably) bugging you.

But if this quest for intel is unsuccessful (or somehow makes you even more frustrated), fear not. In terms of your overall career arc, there are far worse things to be than The Responsible Underling of the Incompetent Colleague. You may have to continue helping out with software stuff and reaching out to other units to maintain active collaborations—and yes, doing that without the accompanying pay/title recognition your coworker’s getting is lame and unfair. However, rest assured that your hard work is not going unnoticed. By supporting your department despite not being its official leader—and diligently maintaining a positive, professional attitude throughout—you will develop a reputation as someone who gets shit done. That quality can be sadly underrepresented in academia (and in workplaces everywhere, for that matter), and I firmly believe that it will lead to good things for you further down the line.

One last thing, too—I find that my perspective on my own workload is infinitely improved by setting and enforcing appropriate boundaries on my time. If your new department head is heavily reliant on you for software assistance, that gives you bargaining power that’s worth using. Figure out which days and times you’re able to be available for training and question-answering, communicate those to her, and then stick to that schedule as much as possible. Develop the capacity to deliver a sincerely regretful “I’m so sorry, but I’m too swamped right now; can we revisit this [when it’s more convenient for me]?” The ability to project cheerful helpfulness (regardless of whatever snarky running commentary your brain might be offering) is a rare talent, but it shouldn’t come at the expense of your own sanity or professional priorities.

In the end, this too shall pass. Eventually she’ll probably get the hang of the software, or else hopefully admit defeat and put those aspects of the job under your auspices; either way, the time spent covering her deficiencies counts toward your “service to the institution” quota and all the positive reputation points that go along with it. You’ve already got an admirable outlook on this whole ordeal—even if it’s currently coming from a place of well-justified bitterness—and I have faith that your attitude will ultimately help you get through it unscathed.


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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