How to Choose a Career Path That’s Right For You

By Claire Wasserman

Whether you’re getting started in your career, unhappy at your job, or simply at an intersection of your life, it can be overwhelming to figure out what to do next. However, instead of focusing on the future which is full of unknowns, I invite you to first examine your past. There, you will uncover clues about where and how you thrive and it is by analyzing those patterns that will point you in the direction of what gives you purpose. You deserve to do work that you’re proud of, and you’ll be more successful in reaching your career goals if you go in a direction that you’ve chosen with intention. Here’s how.



We carry certain expectations of what a career “should” or “shouldn’t be” and we prioritize other people’s definitions of success, instead of crafting our own. So before we start gathering data on what makes us thrive, let’s examine and let go of those “shoulds.”

  • What career paths did you have exposure to growing up? Did adults in your life ever share their expectations for your career? Are there any professions or roles that you feel are totally inaccessible to you?
  • What would you say has been the major driver of your career choices? Has anyone commented on those choices and if so, what did they say?
  • Have there been times in your life where your gut told you something, but you didn’t listen to it? What was stopping you?


One of the keys to figuring out your future is to look for clues in the past. The goal of this exercise is to collect a bunch of data about yourself that you can piece together to find a company, role, and environment that sets you up for success. Think of times in your life when you were “in flow”, meaning, you were completely energized and absorbed by what you were doing.

  • What were you doing?
  • What strengths and skills were you using?
  • Where were you? Were you alone? In front of a computer? Doing something with your hands? (Environment is such a big part of how we thrive.)
  • Now think about times when your energy was depleted. So much of knowing what you want comes from experiencing what you don’t want. Where were you? What were you doing?


I want you to think bigger than the skills you currently use at work. Instead, let’s dig into the strengths that are innate to your core being. When you start looking for jobs, I want you to seek roles that not only require these strengths but prioritize them.

  • “What are things I do really well?”
  • “What do I say, think, or see differently from  other people?”
  • “What comes naturally to me?”
  • Then I want you to reach out to a friend and ask them, “If you were to describe me to someone else, what would you say?”

Instead of passion, I want you to orient yourself toward things that make you curious.

  • What topics or activities do you find that you’re continually drawn to?
  • What are some things that move or motivate you?
  • What are the problems that you want to solve?
  • If those questions stump you, try asking a close friend, “What is something that I never shut up about?”


Values act as a guide along your path, they will help you find companies that have the ethos and environment where you know you’ll thrive.

  • Just the way reflected on the times in your life you felt most alive, I want you to think back to the times when you felt most fulfilled and proud.
  • On the flip side, what about times that were painful or frustrating?
  • What about these experiences made you feel that way?


No one job or one company can have it all so it’s important to know your priorities before you start looking for opportunities.

  • What are you willing to give up?
  • What are you willing to fight for?

Fill in the blank of these three statements:

  • “I would like to have _______________,
  • “I’d rather not  _______________”
  • “I need to have _______________”


Let’s map out those patterns you identified in the data you collected and then write down tangible, actionable micro steps you can take to explore different possible directions to go in.

  • What is one step you can take in a direction that feels good?
  • Are there things you need to learn? (Skills, information, etc.)
  • Who can you ask for help? (For example, make a list of people and/or groups you can network with) 
  • How will you hold yourself accountable? 
  • How will you reward yourself along the way?   

Here’s the ultimate question I have for you and it’s okay if you don’t quite know the answer yet:

  • How do you define success?
  • What feels like success?

I want to be clear that this isn’t something that’s static – your definition of success will change as you change! And that’s a good thing! So along with learning to listen to and trust your inner voice, make sure you’re continually checking in with yourself: are you satisfied? Fulfilled? Growing? What things do you maybe need to adjust and what things do you need to learn? Remember, it’s just one step at a time and if it feels good, you’re good.


With more people getting laid off every day, it’s crucial that you be prepared for whatever happens. Our Get the Job Master Course is available for on-demand access and will give you everything you need to stand out and get hired.

The owner of this website has made a commitment to accessibility and inclusion, please report any problems that you encounter using the contact form on this website. This site uses the WP ADA Compliance Check plugin to enhance accessibility.