How To Break Free From An Unfulfilling Career

Do you ever feel like life just happens to you? One job leads to another and now you find yourself five, 10, or 20 years later stuck in an unfulfilling career. Maybe you feel like you arrived there by accident—never making time to deliberately think about what you’d like to do or how to get there. Essentially you feel trapped. Sometimes this is the result of what career theorists call “career compromise.”  One theory, Gottfredson’s career theory of circumscription and compromise, suggests that for a variety of reasons, people may wind up in careers that they perceive as compromises.  What makes people view their careers this way includes a complex combination of factors including gender, upbringing, socioeconomic status, academic performance, expectations set by others, and one’s ambition and need for achievement. If you feel like you’ve gone down the wrong career path, it’s not too late to make a change. Here are some steps to break free once and for all.

Invest in self-exploration

The first and most important thing to do is to take a step back to understand who you are and why you feel stuck in an unfulfilling career. Find some quiet time with no distractions so you can ask yourself some powerful questions:

  • What are you good at?
  • What do people compliment you on?
  • What activities that you used to enjoy have gone by the wayside over the years?
  • What are some things about your current career that you do like (there must be something)?
  • What activities can you focus on for hours and hours, yet it seems like no time has passed?
  • What are some career ideas that you dismissed early on because you felt that they were too “impractical” or “unrealistic”?

Open your mind

Many people find themselves in an unfulfilling career because they have made choices based on what they “should” do instead of what they “want” to do. Most likely if you feel stuck in a career that isn’t a good fit, you’ve been operating mainly from your “head” and not your “heart.” Making that shift from head to heart is critical to finding fulfillment. Operating from your heart allows you to be open to new opportunities and new ways of looking at things. Let go of society’s expectations. You don’t have to be a doctor, lawyer, or have a fancy degree to be successful or feel fulfilled. Often, we end up making career choices to impress other people so we can feel validated. In the process, we lose sight of what makes us truly happy. As a result, the higher we climb the corporate ladder, the more unhappy and unfulfilled we feel. In today’s world, there are so many options that it’s more possible than ever for you to design your own life (according to your own rules). Open your mind and explore the possibilities! Don’t think about what you’re qualified to do. Think about what you really want to do and then develop a plan to get there.

Find uplifting people

Tony Robbins said it best,

If we surround ourselves with people who are successful, who are forward-moving, who are positive, who are focused on producing results, who support us, it will challenge us to be more and do more and share more. If you can surround yourself with people who will never let you settle for less than you can be, you have the greatest gift that anyone can hope for.”

Once you identify that ideal career, seek out people who are successful in that field. You would be surprised how many of them would welcome a conversation with someone aspiring to follow in their footsteps. Don’t be shy. At the same time, evaluate your current social and professional relationships. Do you feel any of those people are holding you back? Do they share your desire for more in life? If not, it may be time to release yourself from those connections and elevate your standards. Clearing yourself of negative energy so you can let optimism and positivity enter your life can be transforming.

Take small steps forward

Small, consistent steps forward can lead to monumental changes. Most people stay stuck in an unfulfilling career because they are afraid of stepping outside their comfort zone, or they feel overwhelmed at the thought of making a big transition. As the ancient Chinese philosopher and writer, Lao Tzu said, “The journey of a thousand miles begins with one step.” So just focus on that next phase. Perhaps the career you want to transition to requires additional education or certifications. Now is the time to research those programs (maybe you can even complete those requirements during evenings and on weekends) and determine what additional training you will need. Network with people in the field you are thinking of entering to get a sense of the daily grind and if it’s something you might enjoy. Find a coach or a mentor to help you through this phase. Most importantly, create a short and long-term transition plan with concrete milestones to hold you accountable.

It’s never too late to make a career transition. The key is to know yourself, open your mind, find support, and take small, consistent steps.

What you want exists—don’t settle until you get it!

If you’ve been thinking about being your own boss for a while but aren’t sure if it’s the right time, download my free resource: 5 Signs It’s Time to Leave Your Soul-Sucking Job!


  • Caroline Castrillon

    Founder/Career and Life Coach

    Corporate Escape Artist

    Caroline Castrillon is the founder of Corporate Escape Artist and a career and life coach whose mission is to help people go from soul-sucking job to career fulfillment. Caroline made the leap to entrepreneurship after a successful 25-year corporate career and has never looked back. Prior to Corporate Escape Artist, she worked in leadership positions for small tech firms and for large Fortune 500 companies including Dell and Sony. She has an MBA from the Thunderbird School of Global Management and is a Certified Professional Coach (CPC) and Energy Leadership Index Master Practitioner (ELI-MP). In addition to Thrive Global, she also contributes to Forbes and has been featured in publications including the New York Times, Entrepreneur, Inc. and Success Magazine.