Work or Entrepreneurship—Which one is you?

Are you happy with the career you’re in now, or is there something you’ve always dreamed of doing?  What motivates you?  What doesn’t motivate you?  What are you good at? Do you thrive working with others, or do you do your work better on your own?  It can feel daunting to not have clarity right now, or to feel your career focus shifting.  Know that your questioning is a great catalyst for the next big phase of your life.

Recently, I have had people in varying careers question if they belonged where they are in their career, or how they could somehow expand on it.   Some have expressed not being sure if they wanted to do something else, or if doing what they love is something they should go out on their own and do, or maybe find a way to make it part of their career.   Which one is you?

Growing up, you may have been sure of what you wanted to be.  You may have later followed a path into a family business.  You may have gone to college.   You may have had a skill that amazed people how good you were at it, and were told you should be doing it for a living.

I had a professor in college that had been in three different careers—a pastor, a counselor, and a teacher.  I remember thinking, “Wow!  He’s done a lot!”  Well, I have at least doubled the career paths he had taken at that point.  Many people do not end up doing what they went to school for because other things gain their interest, and that’s okay.  The old adage from the philosopher Confucius, “Choose a job you love, and you will never have to work a day in your life.” rings true for myself.  I’ve been on both sides of that quote. 

If you are in a place where you are stuck, whether it’s expanding on your career, taking that leap of faith into entrepreneurship, or following your passion into a different career--there are resources and exercises you can do to help you figure out which direction is right for you.

Turn towards literature.  There are a few books you can turn to on your path of self discovery.  One of the books I turned to, that led me to see that career counseling was something that should be integrated into my practice, was, What Color Is Your Parachute by Richard Nelson Bolles.  He wrote the book for the same reason I picked it up.  His career path was not anything you could walk a straight line on.  Figuring out what to do with your life, that will most likely be most of your life, is a big decision.  There’s also, The Great Work of Your Life:  A Guide for the Journey to Your True Calling, by Stephen Cope. This book can offer contemplation and inspiration.  There is also StrengthsFinder 2.0 by Don Clifton.  This book offers an assessment that gives you five qualities of you that can then be associated with certain careers.

Take notes. I used to administer career interest tests during a graduate school internship.  These tests, if you have not ever taken one, asks questions that can give you a picture of where you might want to be.  They ask questions like the first paragraph in this article-- Do you like to work alone, or with others?  Do you like to work indoors or outdoors?  There are many questions you can ask yourself.  One exercise is to put pen to paper, or fingers to computer, and start listing all the different aspects you want in your career life.  By listing all of the different aspects you prefer, it may start to paint a clearer picture for you. You could also use post-it notes, write ideas down on them, and post them where you will be most likely to look at them, and see what resonates, or if something consistently keeps coming up.

Try an internship.  If you already know what career you have an interest in, finding a place to, “shadow”, or intern at a place you’re interested in may not only confirm if it is the right path for you; but you may also gain connections, make a name for yourself, and end up with the prospect of being able to work there if it is a good fit.  I know someone that recently found their dream job through connections they had made on LinkedIn.  Try asking people on this professional site about their career, and see where the conversation take you.

Embrace your journey.  Finding your exact fit can cause anxiety.  It is a process, and a journey.  With so many choices out there, it can be overwhelming.  But, once you narrow it down, maybe you can then start with one idea you come up with, and build from there.  Trial and error can also end in clarity. Don’t forget, the turtle won the race!

I hope this helps anyone struggling to make a decision, or take a new path.  If you are still in need of more guidance, please do not hesitate to reach out.  I have been there.


1.  Turn towards literature.

2.  Take notes.

3.  Try an internship.

4.  Embrace your journey.