10 Kinda Scary (But Completely Helpful) Questions to Ask Yourself if You’re Unhappy at Your Job

By Julia Laginess (Summer Intern, Miami University Class of 2022)

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That moment when you realize that you’re just not feeling it anymore.

What are you supposed to do when you get to that spot? Ignore it? Let it keep you up night after night? Turn to chocolate, chips or Chardonnay and just forget about it for a while?

Answers to the above, by the way, are: No, no and no.

This is your livelihood. This is your life. So, if you’re feeling unhappy at work, you’re going to do yourself a huge solid if you carve out some time to really think things through — sooner, not later.

Here are 10 questions that’ll help you with the soul searching:

  1. Is my current job the problem, or might I be in the wrong career?

    Ya gotta ask it, even if it feels daunting. The thought of hitting reset, especially if you’ve built up some (or plenty of) career capital in your current field, can seem nearly impossible. But it’s one of the most important questions to ask yourself if you’re feeling unhappy with your work.

    Try this: envision yourself doing similar work as you do today, but in a different environment or with a different manager, clients or co-workers. Would that likely resolve the feelings? If yes, great. Your next steps will be relatively straightforward. If no, it may be time to begin contemplating a career that will better suit you and, ultimately, be more fulfilling.

  2. What specific part(s) of my job or work do I dislike?
    Identifying what, specifically, isn’t good for you can help you decide how to best approach this situation. It’s very unlikely that you’ll be able to respond to your situation productively if you don’t break things down. Do you dislike your coworkers? Is your boss difficult? Are the tasks too hard, too boring or not in line with your core strengths? Are you struggling with work/life balance? Do you agree with the company’s values? Whatever it may be, identifying the specific issues can help you determine your best next move.

  3. Is the fix relatively straightforward?
    If so, great. Start cooking up a plan to address the specific things that aren’t working for you and see if things start improving. If you don’t see this as a feasible option, it’s time to ask yourself this:

  4. Will changing my job or career solve these specific problems?”
    You know what the “grass-is-always-greener” syndrome is, right? Of course. What you don’t want to do is make a kneejerk move, get settled into that new job or career, and then realize, “Oh, man. This is exactly what I hated about the last place,” or “Whyyyy did I not see this coming?” For the number of hours you spend at work every day, week, month and year, you most certainly want them to be enjoyable. Give this the due diligence it deserves.

  5. If I could construct the perfect job, what would my job description be?
    Try envisioning what your dream job would be. And, again, dig in and get specific. What are you doing? What are you not doing? What is the work environment like? How big is your team? What does the organization do? Consider writing an actual job description, so you can really visualize this thing. Now ask yourself, “If I know I deserve that perfect role (you do), will my current job lead me in the right direction, or hold me back from achieving my professional goals?”

  6. Can I afford to simply quit?
    If you’re thinking about straight-up quitting, do you have enough money to cover your living expenses, and for how long? Run the numbers on this one. If you’re ending up in the red, are there other ways you can supplement your income in between jobs? If no, you may want to consider riding it out at your current employer while you search for a better assignment.

  7. Could this be about the pandemic?
    A lot of us have found our lives and jobs to be in a “new normal” state, thanks to COVID-19. And that normal can feel isolating. Perhaps “the office” has been your converted walk-in closet for 18 months. Or, maybe you’re now heading to work every day and feeling anxious about being out there after so many months at home. Whatever the case, try and determine if your current feelings are pandemic-related (and, perhaps, likely to subside as we move past this mess) or likely to stay same or become worse should you stay.

  8. What parts of my job do I actually like?
    I’m going to wager that your current job has at least some redeeming qualities, right? Maybe you’ve got cool co-workers or a sweet expense account. Maybe they offer terrific healthcare benefits or unlimited time off. Now, rank how important these things are to you and do a bit of research — Where might you find an organization and, specifically, a new a role offering the same kinds of positives, but fewer negatives?

  9. Am I still earning my keep, or have I totally dialed out?
    Look, we’ve all had days or months during which we weren’t at the top of our game workwise. Nobody runs at peak performance 24/7/365. But are you at a point in which you’re just phoning it in, day after day, week after week? If so, that’s probably not doing anyone much good — not you, not your customers, not your colleagues and not your customers. You were not put on this planet to be average, or be unplugged. You deserve a job that lights your fire, and the world deserves your best output.

  10. If I continue on the path I’m on, where will my physical and mental health be in ___________ weeks/months/years?
    Certainly, it’s to be expected that your job isn’t going to feel like Disneyland every day. It’s called work for a reason. On the other hand, it also shouldn’t be robbing you of your sanity, sleep and overall health. If you look down the path you’re on right now, do you see potential for relief? Growth? Fulfillment? If no, is the potential price tag worth it?

Self-reflection can be pretty darned uncomfortable, especially when you suspect that your discoveries might prompt major changes in your career or life.

But when you get down to it, wouldn’t you rather happen to your career instead of happening to you?


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