4 Uncomfortable Questions That Tell You What Kind of Work You Should Do

Finding a job is hard.

It’s true whether you’re changing careers, starting from scratch, or looking for a side gig to pull in some extra money each month.

What’s even harder? 

Finding work that’s both suited to your personality AND fulfilling in some way.

More people struggle with this than you’d think. 21% of millennials changed jobs in the past year, according to Gallup. Another 55% say their current work doesn’t engage them.

Why are so many of us dissatisfied with work?

Maybe there’s a disconnect happening between what we think we should do versus what we’d actually be good at. So, how can we close the gap?

The best way to find out what kind of work you should do is to ask some uncomfortable questions, ones that sneakily reveal your true work preferences and passions.

You might not be able to answer all of these questions right away. That’s okay. What’s important is that you’re honest with yourself. If you come up against a wall, keep digging. The more you ask, the closer you’ll get to knowing what kind of work you should be looking for.


What kind of work should you do? Ask yourself these 4 uncomfortable questions

1. What am I NOT good at?

A good way to narrow down your job options is to consider tasks that are difficult for you, that you dread, or ones where your performance is consistently sub-par. Knocking off the jobs from your list that deal principally with these tasks is a good way to find out what kind of work you should do, instead.

However, a mistake many people make when asking themselves this question is answering it on a shallow level only.

For instance, if you’re not good at math, that’s too obvious of an answer. You probably already know you’re going to avoid jobs that deal with numbers, like accounting, banking, or data management.

To best answer this question, think about what you’re not good at within the industry that excites you.

Say you’re interested in marketing and sales. What are you NOT good at in these areas? Maybe you’d say, “I would be terrible at tasks like writing marketing copy or optimizing websites.” 

Once you have that initial answer, dig deeper. Why would you perform these tasks poorly? You might say, “Well, my attention to detail is poor, I hate working alone, and I’m not especially creative.”

Now you’re getting somewhere. With this information in hand, you can immediately strike out any jobs that require introverted, detailed, or creative work and focus on ones where you can be your extroverted self, focus on the big picture, and use your powers of analysis or logic.

See how that works? When you figure out what you’re not good at, you’ll find out where you excel.


2. What past jobs made me miserable?

Maybe you enjoyed all your past jobs and have nothing bad to say about any of them. (If that’s you, congratulations—you’re in the minority. The average number of jobs people have in a lifetime is 12, and it’s highly unlikely that all of them are pleasant.)

For most of us, there’s at least one job in our past that we really, really disliked. One we dreaded each day. A job we rejoiced to be finished with forever.

Maybe you worked retail throughout college and hated dealing with rude customers. Perhaps you worked briefly for an accounting firm and despised all the paperwork you had to wade through. Or maybe you worked in an office and were miserable stuck inside the same four walls day after day.

Whatever you did, ask yourself why you were miserable and what factors played a role. These are aspects of work you should potentially avoid in your next job opportunity.

Vector Marketing Instagram post, "What should I do with my life? That's a really scary question."
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3. What am I willing to give up to pursue the right kind of work for me?

All new opportunities require some kind of leap. You have to sacrifice something, whether it’s your time, your comfort zone, or even a tiny piece of your identity—especially if you’re starting a new job in an unfamiliar industry.

So, the question is, what are you willing to sacrifice to find the right job for you? More importantly, what are the trade-offs between your current situation and starting a new type of work?

  • Will you make less money at your new job (but feel more confident in your new role)?
  • Will you have slightly less free time (but greater satisfaction at work)?
  • Will you be abandoning an industry you know well for one where you’ve barely scratched the surface (but the learning opportunities excite you)?
  • Will your routine completely change (ultimately for the better)?

When considering a new job, think carefully about what you’re giving up, but also think in terms of what you’ll be gaining by shaking up your work life. Both sides of the coin matter.

Bar graph showing why workers change careers

4. How does work fit into (or not fit into) my life?

The last uncomfortable question you should ask yourself is perhaps the hardest.

How much does work matter in terms of your life satisfaction? How does it fit into the way you live (or the way you want to live)?

  • Do you need your work to take center stage? Do you need to be successful at work to feel accomplished in your life?
  • Or, maybe work is not your #1. Maybe building your family life is what gives you fulfillment, and work is simply what keeps the lights on.
  • Or, perhaps you fall somewhere in the middle.

However you answer this question should inform the kind of work you do. For example, if the second option is the most like you, then a demanding career that requires most of your focus and time probably shouldn’t be your goal.


To find the kind of work you should do, get uncomfortable first

It may be hard to ask yourself these questions and answer honestly, but it will lead to a better outcome.

What would you rather do: Deny your true needs at work and dread your job, or confront your true skills and desires and find the work that suits you?

The right answers are in front of you. Don’t be afraid to dig in – the work you were made to do is out there waiting.

The next step is here. See if you’d be a good fit working with us at Vector.