Determining Career Direction

Feeling lost when it comes to your career? You're not alone.

The experience of being in a job you hate--with no clear direction on where to go next--is really exhausting and debilitating. I believe that the key to career satisfaction starts with a better understanding of self. Below, I've listed a few resources and exercises that might help you along the way. 


Assessment tips:

  • Carefully read and follow all instructions to ensure accurate results.
  • Answer honestly; don't worry, no one will see the results but you!
  • Remember that assessment results are a tool, but rarely 100% accurate. They never show the complete picture of "you." Take what is helpful, and leave what is not.

Self-Assessments: To Thine Own Self Be True

Fair warning: I am a big-time assessment nerd. I believe that quality assessments can provide helpful information and insight for developing a better understanding of yourself, and thus these tools can empower you to more fully live your life according to who you are and how you're wired. 

There are several types of assessments that you could take, but the ones I would most recommend fall into the following categories: personality, behavioral style, and values assessments.

The internet is full of assessments, and honestly, many of them are garbage. Here are a few recommended assessments, broken out by what is free and paid, with direct links provided:

Free Assessments

Paid Assessments

Job History Exercise: Examine What You Love

This is one of my favorite exercises for career direction, and has been one of the most fruitful in my experience. My father actually suggested this activity when I was feeling lost in terms of career direction, and it was a game changer for me.


Write down every job you've ever had, all the way back to your high school days or first part-time gig. Depending on your situation, it might be good to include volunteer experiences as well.

For every job on the list, answer the following questions:

  • What was your favorite thing about the job? What did you enjoy the most? What energized you?
  • What were you most proud of in that role? What project or result or client interaction makes you smile the most?

After you've answered these questions for each job, look at the big picture. What trends do you see? Are there obvious themes or careers that are closely related to the tasks and projects you've highlighted? See where this path leads you, and take some time to explore the new opportunities that follow.



Volunteer Opportunities: Test the Waters

Perhaps you have an idea of a new career you'd like to try, but making the shift seems like a major gamble. Volunteering or job shadowing is a great way to get a taste for a new industry or field without the risk of diving into a new career blind. This is particularly useful if, like me, you have a tendency to idealize or romanticize. 

Contact some of the leading companies or organizations in your desired industry, and see if a volunteer or job shadow opportunity might be arranged. As a bonus, those contacts might be extremely helpful in your job search down the road.  

Ask Friends & Loved Ones for Help

Sometimes our closest friends and family members can see us more clearly than we can see ourselves. 

Make a list of people who are really "for" you -- they celebrate your wins, and mourn your losses with you. Ask them to consider a few specific questions, and give them plenty of time to consider and thoughtfully respond. You can write your own questions, or use the following as a guide:

  • In our conversations, what seems to get me the most excited? What subjects make me lean in, and really engage?
  • In your opinion, what are a few of my greatest strengths? 
  • In what areas do you believe me to be uniquely gifted? 
  • If you were responsible for guiding my career, what path might you point me down? Why?

Remember, you might get conflicting information with this exercise. And not all advice is good advice; listen to the feedback you receive with a discerning ear. But generally speaking, don't underestimate the input of your loved ones.