“Dear Businesslady: Do I Want To Have Two Jobs Forever?”

Some advice on good problems and bad jobs

Hey Businesslady,

I have a job that I genuinely love. I work in a small office with people who have become close friends and most days, I actually enjoy coming to work. My job is so good to me — it’s a supportive, happy workplace.

I also run a side business that’s fulfilling in a way that is very different than my day job.

It’s getting to the point where I will soon need to choose between the two, and I honestly do not know what to do. I’ve put so much effort into building a company that can now sustain itself. But I don’t see this business ever being able to pay me what I make now. I’d probably make less than half my current salary.

So I’m stuck. My day job is flexible and knows about my business. They have offered to figure out a way to have me work part time if needed, but I can’t decide if that’s even what I want. Do I want to have two jobs forever?

How do I even begin to think about this? I am so proud of what I’ve built with my partners, but I also like a comfortable paycheck and love the work at my day job. My husband is on board with whatever makes me happy … a sweet sentiment, but not overly helpful.

I know no one else can tell me what the right choice is, but maybe you have some insight that will make me realize what I want for myself.

— A Good Problem

Dear G.P.,

I chose your letter, and the one below, for my first column on the Billfold, because they both illustrate the complex trade-offs a person has to navigate when forging a career: effort vs. reward, compensation vs. fulfillment, enjoyment vs. stability, and so on.

As you note, yours is a good problem to have. From the outside, it looks as though you’re choosing between two equally enviable possibilities, and I wouldn’t begrudge any reader a moment of grumbly “must be nice!” in response to your letter. But you know that you’re lucky to be in this position, and the fact that both of your choices are compelling only makes your decision harder.

The simple answer, my actual here’s-what-I-think-you-should-do advice, is to go part-time at your preternaturally accommodating day job and see how you feel about devoting more time to your business. That’s the route that grants you the most flexibility, and I think it might be more appealing to you if you move away from the sense of having two “jobs.” Everyone’s professional life is a patchwork of various tasks, and there’s plenty of necessary work we all do without getting paid for it. (You’re expected to show up to the office wearing clean clothes, for example, but no one’s compensating you for your laundry time.)

So the question is really about how many hours you have in a given workweek, and whether you can devote more effort to your business while still making the most of your day job’s other advantages. And you want to keep your day job in the mix for as long as possible, because: money. I’m fully in favor of taking a salary cut in exchange for other meaningful perks — there’s probably a Better-Paying But Shittier Job out there for almost everyone — but you have to be sure those perks are worth it.

Your husband’s input thus far seems pretty theoretical, and if you share finances, this is a decision with a practical impact on his life too. It’s all well and good to say, “Whatever makes you happy,” but if your reduced income means you have to skip a vacation or freak out over an unexpected car repair, how is he going to feel about it then? I’m not trying to suggest he’s being insincere or avoidant, just that it’s easier to be supportive about an abstract thing versus a distressingly low number in your checking account.

I don’t know anything about your finances, so maybe a reduction in your pay means “less money going to savings” rather than “suddenly strapped.” The thing is, we all have different baselines for our own well-being, both personal and fiscal. Not everyone has a choice in the matter, obviously, but for those who do, there are the savers who feel anxious without a substantial emergency fund, and then there are the spenders who would rather enjoy the good life now even if it means they’ll need to do some painful belt-tightening if their situation abruptly changes.

Similarly, some people cannot bear the thought of putting aside their passions in favor of a steady income, while others prioritize stability and/or the kinds of material comforts that money provides. And some people have a seemingly infinite capacity for workworkwork — they thrive on 16-hour days, late-night crisis management, weekends at the office — while others reach a hard limit of “literally no money would be enough to make me do a thing.”

Which kind of person are you, then? It’s fine if you don’t know yet. But you have to be honest with yourself, and with your partner, about which way you’re starting to lean. If working two jobs is burning you out (or if you choose your day job and then miss being more involved in your business), don’t suppress that because you feel obligated to earn as much as possible. And if you go all-in on the business and find you can’t deal with the new financial reality it introduces, don’t struggle in silence because you’re afraid to say, “I made the wrong choice.”

It’s often hard to know what makes you happy until you realize what makes you unhappy — these things aren’t easy to assess through pure speculation. But if you take a clear-eyed look at your options, make a decision, and then remain alert to signs that it’s not actually working for you, you’ll end up where you want to be.

— Businesslady

Dear Businesslady,

Last September, I completely switched fields from the tech sector to the arts. I felt, for the first time since graduating college, that I had finally found a good career path for me. I genuinely love this field and desperately want to avoid going back to a more traditional industry.

The problem is that the business I currently work at is owned by a delusional, abusive, and vindictive man who has steadily increased the amount of work my colleagues and I have been given, as well as work beyond our job description, with no corresponding increase to wages. This is at least partially due to the owner’s financial problems. We don’t get benefits and are routinely denied vacation, as well as being expected to work at least one full weekend a month (this looks like it will increase to two weekends based on the projected schedule). This is all additionally compounded by planning my wedding. My coworkers are all threatening to leave within the month if nothing changes for the better.

I’m at a loss. I don’t want to stay at a potentially sinking ship that treats me poorly and I don’t want to look for another job that I’ll likely have to quit in three months so my husband and I can move. What would you do?

— Sinking Feeling

Dear Sinking,

If your companion above has a “good problem,” your situation might qualify as a “bad problem.” At least, it’s less likely to induce jealousy. But instead of thinking of it as a “problem” at all, I’m hoping it can be a useful illustration of a point Alison Green made the other day: “Work doesn’t always have to be about that kind of fulfillment. It’s okay for it to be about supporting yourself and your family and not a lot more.”

Your job sounds like it sucks right now, and if it helps for you to read that in digital print, I’m happy to say it. But despite that, I think you’ll be best-served by staying put and toughing it out for a little while longer. You’re planning a wedding and a likely relocation! My answer would probably be different if the rest of your life weren’t in flux, but since it is, a job search would overcomplicate things.

Let “it sucks, but…” be your mantra until you’re able to leave.

It sucks, but … it’s giving you experience in a field you love.
It sucks, but … it’s showing you How Not to Manage.
It sucks, but … it’s providing you with an example of the type of job you don’t want in the future.
It sucks, but … it’s only temporary.
It sucks, but … it’s better for your resume if you stay put until you move.
It sucks, but … it’s an opportunity to practice pushing back against a crappy environment.

To this last point, from where I sit, you have very little to lose. You know you’re not going to be at your current workplace forever, and if your boss is going to be a jerk no matter what, trying to remain in his good graces sounds like a waste of energy. You’re about to embark on a new phase of life on a couple fronts, and in the meantime your primary professional obligations are to your coworkers and to your own career.

Your colleagues may not have such clearly defined exit routes, so you might be doing them a favor by pushing back against your manager’s most egregious demands. As long as you’re doing it calmly and collaboratively (“it is becoming difficult for us to do quality work under these conditions”) it shouldn’t jeopardize your chances of getting a good reference.

And since you’re relatively new to the workforce, this is great training for the delicate conversations you’ll have in the future. “I am upset about this thing but also respect your authority and need us to remain on mutually positive terms after we discuss it” is a position you’ll find yourself in throughout your career, and the stakes will only get higher from here. So consider this your laboratory for experimentation. Which approaches feel the most natural to you — and which are most effective when dealing with an unreasonable person?

Beyond that, think of this job like a cold or the flu: an unpleasant experience that has to run its course. Try to put distance between yourself and the stresses of your office, keep your work performance somewhere above “doing the bare minimum,” and be as supportive as possible to your coworkers. You never know where they’ll all end up in a few years, and making a good impression on them could pay off.

If the ship sinks while you’re still on it, that’s not going to be fun for anyone. But the nice thing about being an employee rather than an owner is that you’re not ultimately responsible for an organization’s success. If anything “my former workplace ceased to exist” is the easiest possible answer to give interviewers who want to know why you’re job-searching. (Second only to “I moved,” so you’ve really got that question on lock.) This isn’t your personal passion project or your life’s legacy; it’s a means to an end, a source of a paycheck that hopefully will pave the way toward better jobs down the line.

If you want one last silver lining, consider this: while the first letter-writer is faced with a tricky dilemma, your choice is clear: get a new position as soon as you’re able. Even a “good problem” is worse than having no problems at all, and yours is rapidly heading toward resolution. Soon, you’ll be starting over in a new place, and any job will seem better by comparison.

— Businesslady

In need of workplace advice? Email me! dearbusinesslady@gmail.com
Want more Dear Businesslady? The archives are still up on The Toast, and I’ll be back with another column in a month.

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 (including but not limited to Twitter).

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