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Dear Businesslady,

I’ve finally gotten a job that fits my background (field A) pretty well, is stable, and pays decently. I’ve been working toward getting a job in this field for a few years, but now that I’ve finally got it, I’m afraid it doesn’t fit me. I feel like someone more extroverted would be better suited to the job. Also, I’m finding it quite directionless and unstructured. Worst of all, I’m bored out of my mind.

I kind of want to switch gears to a different field of the same flavor (field B), which I have enough experience in to be dangerous. But this is where I’m torn. I think I would have to go back to school to be some sort of competitive in field b… and that has a whole different set of concerns. 1) Paying tuition while paying off student loans sounds like a world of pain. 2) I’ll be stuck in entry-level work forever because of my late start. 3) I’m afraid I haven’t given the job in field A enough time (it’s been about a year, and my job history is already full of short tenures so I don’t know if I’m just a job-hopper and need to suck it up).

Would I be throwing away my time and money if I moved into field B?

Sincerely,
Be Careful What You Wish For

Dear Wish,

Both of the questions in this column are about hindsight, broadly construed—yours is the abstract, big-picture variety and your companion’s is about a specific as it gets. But both reinforce this crucial point: the only thing worse than not getting what you want is getting it, then realizing you didn’t actually want it after all.

I’m already optimistic for you, though, because at least you have the wherewithal to reflect on where you’ve ended up and reconsider whether it’s where you want to be. So many people are so afraid of admitting they’re wrong that they spend entire careers, marriages, lifetimes going down the wrong path simply because they don’t want to have to question their past decisions. Looking around and thinking “I’m not sure this is working” takes both self-awareness and courage, qualities that will serve you well no matter where you go from here.

That wasn’t your question, though; your question is whether or not pivoting to field B will be a waste of time and money. And my answer is…maybe?

Helpful, I know. (You’re welcome!) But let me back up.

First of all, I don’t want to frame the wasting of time and money as an unacceptably negative outcome. It’s something you’d want to avoid if possible, sure, but let’s not pretend that we aren’t all constantly wasting both of those things in our daily lives. If we all felt like failures every time a quick 20-minute internet check-in turned into an afternoon of glazed-eyed reading, or every time the food we truly intended to eat spoiled in our fridge, or whatever, then we’d be too paralyzed with guilt to do anything at all, ever. And if that lost time and money helps us make better choices in the future—helps us stay focused on our to-do lists, helps us resolve to cook in before the spinach goes bad—then I’d argue that those resources weren’t even wasted.

More to the point, I can’t possibly know things would turn out if you attempted a career change, and neither can you. But what I do know—because you told me—is that you’re bored and unsatisfied with where you are right now, and you’ve identified one potential way to change that. Maybe you’re right: you’re too late to the party in field B, and/or you’d have to invest a huge amount of capital and energy into additional education, and/or your job history will make it tough for you to land a position. But maybe you’re wrong, and it’s not that hard after all.

Assuming you have enough income to support yourself at a reasonable degree of comfort, an entry-level(ish) job in a field that excites you is preferable to a better-paying job that feels like a prison. I believe that with all my heart. I also know firsthand that sometimes, once a workplace gets to know you, they’ll allow you to circumvent certain credentialing thresholds as you move up in the ranks. Obviously if field B requires strict kinds of training, that might not be applicable, but if additional education is truly required, I can see an organization offering the kind of tuition support that will help a valued employee get promoted.

That leaves the short-stint thing, which okay, isn’t ideal. But job searches can often take a long time (as a wise woman once pointed out), and a series of yearlong positions is better than a bunch of shorter stays. You’ve already been in the boring field-A gig for a while, and time will keep ticking away if you start putting out feelers toward field B, so I don’t think it’s prohibitively soon for you to start planning an exit.

Plus, job applications are all about crafting a narrative that explains why you’re a promising candidate, and your resume has already begun to tell the story of your slow journey to your chosen field. If you write a cover letter that narrates your career to date as a series of Goldilocks-like attempts to find the right fit, each of which has helped you realize that field B is where you want to be, I can see that being compelling to employers. Maybe not all of them, sure, but a certain degree of rejection is par for the course whenever you send applications out into the world.

So my advice, then, is to find field-B jobs that you’re qualified for and start applying. Put thought and consideration into how you present yourself, and try to preempt any snap judgments about your likelihood to stick around based on your job history. If nothing else, hopefully you’ll at least get a couple interviews that put you into closer contact with the offices where you want to work, and that will give you more data points to include while assessing your options. You’re not obligated to take any job you apply for (more on that below!) so if being onsite makes you realize the grass isn’t actually greener, that’s still useful information to have too.

If you strike out entirely—or if you otherwise get feedback that suggests that yeah, you’ll need another degree if you really want to pursue field B—then you’ll have a new choice to make. But maybe by then it’ll be possible to embrace the boring boringness of your current job, letting your mind rest during the day as you take night classes. Or maybe field C will have popped up on your radar in the interim, and you’ll find yourself going in yet another direction that you can’t even picture right now.

With all of these hypotheticals, the specter of “failure” lurks on the sidelines. But what does failure look like, really? Even if you end up adding to your student loan debt and then taking a field-B job that lays you off immediately in an unceremonious and demoralizing way, will you really look back and say “I made a mistake?” Every day, we all make choices that unwittingly set us on the road to bad luck—there are probably things I’m doing right now that I’ll regret in a few months once the results come in. But the only way to avoid that possibility is to avoid making choices at all, to stay where it’s safe, and to endure a thousand minor frustrations instead of (maybe!) one big catastrophe.

It sucks when happiness remains elusive despite your best efforts to pursue it—but if you don’t pursue it at all, it will be forever beyond your grasp. You’re not happy now, and you think you might be happier if you did a different thing. That “might” is powerful, and I think you should follow it and see where it takes you.

—Businesslady

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Dear Businesslady,

I recently received a job offer for a new position that with salary and benefits works out to be about equal to my current job, but only full time hours (I currently work a lot of unpaid overtime). They also agreed to push back my start date several months due to some family issues I have. I was so pleased by this concession, I didn’t try to negotiate for a higher salary. Now, they are saying that the 3 month probationary period I agreed to will not include health coverage. I already signed the acceptance letter, and it was not spelled out in the letter that health benefits were not included from day one. I also have not yet put in my notice at my current job. My entire family is on my health plan and I cannot afford to pay for COBRA. What are my options at this point? Am I obligated to accept this even though it wasn’t spelled out? I have 3 kids I need to think about!

Feeling Like I got the Bait and Switch

Dear Switch,

Ugh, this is such a terrible and stressful situation, and I don’t envy your position at all. I hate to use you as a cautionary tale, but I hope everyone reading this will be like “holy shit, you need to get the relevant benefits info spelled out before accepting a job.” That’s true even if you’re just flying solo (PSA: no one, no matter how healthy, is sufficiently immune from medical calamity so as to make insurance unnecessary), but it’s especially important if other people are relying on you for coverage.

As someone who’s been on employer-provided insurance ever since Obamacare was implemented, I don’t really know whether or not that would be an option for you, but based on your invocation of COBRA I’m going to assume it’s not a viable possibility. And I do know that COBRA is laughably expensive in anything but the shortest of short-term periods. I also know that it’s not terribly unusual for healthcare coverage to kick in a little while after your official employment starts when you’re switching jobs—3 months seems like it’s on the longer side in terms of delays, based on my experience, but not egregiously so.

So, who’s to blame here and what to do? I’ve already said my piece about “please review your benefits super-carefully” so I don’t think I need to restate that—and I’m sure that for the rest of your life, “and when does the coverage begin?” will be permanently etched on your list of Things to Ask Before Accepting a New Job. Regardless of my in-hindsight advice to you, it’s lame that your new company didn’t make it more explicitly clear that you weren’t going to get insurance from day one.

Assuming you still want to take the job, I’d circle back to the new org and explain the miscommunication. If they were pretty upfront about the benefits timeline and you just overlooked it, this gets trickier, because you don’t want to start a job as “the person who didn’t read things closely.” But if it’s a circumstance where any reasonable person could’ve missed that detail, you might get some sympathy from them, and the negotiations can continue from there.

That said, it’s hard to say what level of flexibility they might have on this front, no matter how bad they feel about the bind they’ve put you in. It could be that the policy prohibits earlier coverage, or that there’s enough of a precedent (other people in similarly fraught situations who just had to deal) that it would be truly unfair for them to make an exception in your case. But they’re the ones who know what’s possible, so you might as well begin that conversation. If your start date is pushed way back, is there a way to get you on the books but “on (unpaid) leave” so that your probationary period and insurance waiting period overlap? Could you sign a document explaining that you understand you’re still on probation as an employee despite getting insurance coverage sooner? I don’t know if any of these are feasible (or, to be perfectly honest, legal—if this is anyone’s area of expertise, please weigh in), but I can see there being some chance of working around the waiting period.

If the new job can’t meet your insurance needs, then no, you’re not under any obligation to accept it. I mean, I’m sure your would-be colleagues won’t be thrilled to have to relaunch their search and you might have an uphill climb trying to get hired there again in the future. But you won’t have committed some kind of moral atrocity. People turn down job offers all the time for reasons exactly like this one. The only difference for you is that you accepted on (as far as you were aware) a faulty understanding of what the offer entailed. That’s no different from showing up for your first day as a copyeditor and learning that, oh, your desk is located on the back of this moving horse—or some other unexpected and significant deviation from what you reasonably expected. In terms of the big-picture narrative of your career, no one will judge you for backing away from this position.

So if there’s one silver lining here, it’s the fact that you haven’t yet resigned from your current job. I don’t like the sound of this unpaid overtime you speak of (because it’s illegal! The Dep’t of Labor can give you more info), but I also know that DoL regulations and actual business practices don’t always align as well as we might like. And based on how accommodating this potential new job was willing to be, that suggests you’re an attractive candidate who’s likely to get hired again somewhere else eventually—ideally a place with less of a start-up delay for its benefits.

As a final note, if you do end up having to rescind your job acceptance, try to frame it as an honest misunderstanding about benefits rather than active obfuscation on their part. I completely understand your frustration and I’d feel bait-and-switched if I were in your shoes too. But retroactively turning down a job offer is slightly awkward professional territory and you’ll be better-served in the long term if you keep things as friendly as possible while disentangling yourself.

Beyond that, good luck, and here’s to your and your family’s health (…insurance). Sorry, I couldn’t resist.

—Businesslady

P.S. Confidential to my beloved Toasties: This is not the last installment of Dear Businesslady! I’ve got one more column that will run in June. And even after The Toast closes up shop, I have no plans to disappear. I’m still figuring out where you’ll be able to find me once we enter a post-Toast reality, so watch this space for updates next month. And if you need advice or otherwise want to get in touch, just drop me a line: dearbusinesslady@gmail.com.

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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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