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How to Choose a Career You’ll Love

Updated: May 2, 2019

hiker at a crossroads

You’ve probably had a few sleepless nights thinking about how you’ll choose a career.

It’s a big decision. One that’s not made any easier by high expectations.

How do you find something that’s aligned with your values, makes you happy, keeps you motivated and fulfills your life purpose? Oh, and don’t forget – something that plays to your strengths, makes your parents proud, and pays well. That’s a tall order.

The truth is – no career will check all the boxes all the time. The trick is to get as close as possible. Let’s talk about how to do just that.

Who the Heck Are You?

Sure, you know what you like and dislike, but sometimes it helps to take a personal inventory.

Take a moment to ponder these questions. You might be surprised at how quickly they narrow

your list or open your mind to new possibilities. Write down what you’ve learned.


  • Does being around people energize or deplete you?

  • Do you enjoy a busy, dynamic environment or a quiet, focused workplace?

  • Are you self-motivated or do you need direction to stay on track?

  • Can you react spontaneously or are you more of a planner?

  • Can you read/respond to others’ emotions?

  • Do you feel more comfortable in a small, medium or large company?

  • Where do you want to live? Urban, suburban, rural?

  • Do you seek stability or variety?

  • Are you a people pleaser?

  • Do you like short tasks or long-term projects?

  • Do you love being the center of attention or prefer a behind the scenes role?

  • How do you handle deadlines and pressure?


  • Do you want to be a leader in your field or industry?

  • Do you want to be an entrepreneur?

  • Is a legacy important to you?

  • Would you rather have more time off or more money?

  • What financial goals do you have? Home, children, travel?

  • Would you be unhappy if your job didn’t help others (directly or indirectly)?

  • Are there industries or specific companies that you would never work for?

  • Do you want the ability to not think about work as soon as you leave?

  • Do you want to be defined by your occupation? Or is it just a piece of your identity?


  • What comes naturally to you?

  • What do other people tell you about your strengths or weaknesses?

  • What is a struggle no matter how hard you try?

  • What unusual skills do you have?

  • What skills do you have that are very transferable to different environments? (For example: writing, leadership or project management)


  • What are your hobbies? What aspects of them are similar?

  • Do you have a passion about certain causes? Why?

  • Do you like being outdoors?

  • Do you like working with your hands?

  • Are you artistic?


  • What personal experiences do you have that would give you special insights?

  • What work experience do you have? What industry, organization type, or size?

  • What is your degree? Did you enjoy the subject matter?

  • Would you be okay with pursuing higher education if you had to?

Test Your Assumptions

It’s important to validate what you know about yourself. One way to do this is through self-assessment tools. These tools can provide insights not accessible through your own self-reflection. Plus, some of them use the results to suggest careers that suit you.

There are many free tools online, but you may want to invest in something with a track record in terms of scientific reliability and usefulness. Here are three great options:

Strong Interest Inventory

The Strong Interest Inventory measures your interest in a broad range of occupations, work activities, hobbies, and school subjects. It’s based on the concept that people in the same career have similar interests. Your results are compared to the results of people successfully employed in certain occupations.

With over 80 years of data to support this tool, it’s a great way to get some objective insights. Depending on the report, it ranks your top five or ten most compatible occupations from a list of 260 specific jobs. Bear in mind that you’ll need a professional certified

in administering the test and evaluating the results.


Based on the book StrengthsFinder 2.0, the CliftonStrengths tool uncovers which talents you rely on to build relationships, think strategically, execute plans and influence others to accomplish goals. The test is made up of 177 paired statements. For each one, you choose which one best describes you. Your answers measure your natural patterns of thinking, feeling and behaving. After the assessment, you’ll receive your top five strengths with valuable information about how to leverage these attributes. This is an excellent tool to help you be clear about your strengths and weaknesses.

The Myers-Briggs Type Indicator

The Myers-Briggs Type Indicator is the most widely used and respected personality assessment. Although not specifically designed to choose a career, it’s a great tool for self-awareness. Plus,

you can request a separate report that includes a list of occupations ideal for your personality type.

The assessment is based on a theory by Carl Jung. He theorized that there are four pairs of opposite preferences. They indicate how an individual directs and receives energy, takes in information, decides and comes to conclusions and approaches the outside world. Only an MBTI Certified professional can administer the test and provide results.

Learn More About Your Career Options

Now that you’ve spent some time in reflection and have the results of your self-assessments, hopefully you have a list of possible career options. Here are some ways you can further

evaluate them.

Research Career Profiles

Your best place to start is OneCareerStop, sponsored by the US Department of Labor. They have Occupation Profiles for more than 950 careers. Each profile provides a job description, including examples of what you might do in an average day. You’ll find the job outlook, salary ranges, and education requirements. They also outline what knowledge, skills and abilities you need to succeed in the job.

Set up Informational Interviews

Using your online and offline network, find people who currently work in the fields you’re interested in exploring. Just be clear that you’re seeking information, not a job. Schedule a brief interview to better understand their day-to-day work. Here are a few tips:

  • If you’re searching on LinkedIn, look for people with whom you have a connection, even if small. For example, you went to the same college, lived in the same city, or both volunteer at the Red Cross.

  • Be clear that you only want 20-30 minutes of their time.

  • Flattery doesn’t hurt. Explain why you’ve chosen them specifically. You want to model your career after theirs.

  • See if you have any connections who could introduce you.

Visit a Career Center

If you’re still in college, get yourself over to the career center. Even after graduation, you can still take advantage of their offerings. They might be able to administer some of the self-assessment tools described above or connect you to professionals for information interviews.

Find a Mentor

Your mentor doesn’t have to be in the field you’re pursuing. They just need to be a reliable and experienced sounding board for your career exploration. More importantly, they should know you well enough to provide insights about your personality – and you trust them enough to listen.


If you’re feeling overwhelmed or stuck, don’t worry. When you choose a career, it’s not set in stone. You can reinvent yourself as many times as you need – and you should. That’s the key to being happy. Your 20-something-self can’t anticipate everything. Be as thorough as you can right now and try to build in some flexibility, so you can pivot if needed.

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