Choosing a career path can be a confusing, complicated, and—at worst—depressing experience. Asking these questions can help clear the fog.

Choosing a career path can be a confusing, complicated and—at worst—depressing experience. With so much pressure to follow your dreams, become a success and have all your sh*t together by age 25, it’s no surprise the phrase “career planning” can get your heart racing.

But finding a career you actually like doesn’t have to be rocket science. You’re basically looking for a job that fits your interests, skills and needs. Doesn’t sound too bad, does it?

Ask yourself these 10 questions to figure out if a career is really right for you:

1. Does this career let me follow my passion?

This is a trick question; you don’t have to follow a passion to have a great career. But you shouldn’t hate your job, either. So a better question to ask is, “Does this career path interest me on a general gut level?” (For more on decoding the passion puzzle, check out Cal Newport’s latest book).

2. Am I choosing this career to please somebody else?

If the answer is “yes” or even “maybe,” it’s time to reexamine your priorities. Friends and family can offer great advice, but it’s hard to find happiness when your life is dictated by somebody else’s expectations. You deserve to find a career that fits who you are.

3. What’s my style?

A career that’s a good match will suite your work style inside and out. Are you a self-starter who thrives on high-intensity hustle, or are you more of a procrastinator who does well in a structured work environment?

Be honest with yourself and choose a career that coordinates with your work style and strengths.

4. Do I like people?

On average, you’ll spend one-third of your life with your coworkers. If a job is a bad social fit (example: an extreme introvert in a customer service position), unhappiness is almost guaranteed.

5. Can I be successful in this career?

If you’re willing to put in the hours, you can learn just about any skill. However, finding a career that plays to your natural talents can make life much more pleasant.

If you’re a creative type, you’ll have better luck in a job that utilizes your outside-the-box thinking than a gig that’s all cut-and-dry numbers. Sounds obvious, but it’s surprising how many people don’t consider this.

Also, think about your own definition of success. What really motivates you? Money? Helping others? Work-life balance? Figure out what drives you and then pick a career that will help you reach success on your own terms.

6. Is there a good chance I’ll make as much money as I want/need?

Money shouldn’t be the main deciding factor for a career choice, but it shouldn’t be overlooked, either. Give yourself a reality check to see if your salary expectations can be met within your career field—the social worker who plans to make $100K a year will be sorely disappointed.

It’s also a good idea to take a long-term view. Rather than focusing on starting salary, use a site like to figure out the average income of mid-career professionals. This gives you a more holistic picture of the money situation.

7. Can I afford to get the training I need?

Many careers require formal training, whether in the form of a degree, a certificate or a license. But before you shell out money for college or grad school, make sure the career path you’re interested in will pay off (see question #6).

8. Does this career have a shelf life?

If at all possible, aim for a field that’s hiring. A dwindling industry (like publishing or post office work) can increase competition and make it harder to find a job with long-term possibilities. Check out the US Bureau of Labor employment projections—or better yet, industry chatter—to get a general sense of whether a career field is going places.

9. Do I have an escape plan?

If your industry took a nosedive next week, you’d want to have skills that translate to a new career. These usually come in the form of soft skills like a talent for communication or leadership. Adaptability—and the good sense to pick a career that lets you develop in diverse areas—is the key to continual success.

10. Am I ready to fight for it?

In today’s job climate, you won’t find many (or any) fields that aren’t competitive. Even entry-level gigs can be tough to land. So you’ve got to be willing to go to bat for your career. If you’re not ready to fight for it, you probably don’t want the job.

What questions would you add to the list?

Annie Favreau works for Inside Jobs, a site that helps people discover strong careers and connect with the right education to achieve their goals. Follow her on Twitter at @InsideJobs!


  1. Career Coach,

    Question #2 is spot on.

    I see a lot of people who choose their career paths based on social pressures and wind up unhappy.

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  3. cole

    “Also, think about your own definition of success.”

    Yes! Thank you! That’s exactly what I keep telling people. Most individuals see others as successful only when they are financially wealthy or in a position of power which is very misguided, if not dumb. We have our own dreams, thus only us can say if we are on the right track. For example, I do not care about having an expensive car or buying a huge house, (I wont mind of course, but they’re not my priority), or a fancy title (which I recently got, but mehhh). What I actually want is to leave my own legacy. Peace of mind too, but I dunno what career gives that. 😛

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