Choosing a pathHave you ever found yourself at a crossroads where you are feeling unfulfilled at your job or business, and know that something has to shift, but you are not sure what to do next?  Have you ever agonized over whether to just leave and start over, or stay and try to make things better?

I know what that feels like, because I spent the better part of three years struggling with one of the biggest decisions of my life — should I stay in a job that once brought me great satisfaction, but was no longer fulfilling?  Or should I leave and start a brand new venture that would let me express my creativity and passion?

It all started when I was promoted to an Associate Dean position at the law school where I had been teaching for 15 years.  I was put in charge of the whole academic program, which sounded like a really great opportunity. I love teaching and learning, and spent a lot of my time thinking about how we could improve the law school experience for students.

Glamorous as it sounded, on a day to day basis, the job proved to be pretty monotonous.  Scheduling classes and exams, assigning professors to courses, and filing endless reports with the University and outside agencies simply were not tasks I enjoyed doing.  I missed the challenges of interacting with students, figuring out how to help them develop their professional knowledge and skills.  I was so unhappy that I seriously considered leaving the law school and starting my own business.

But something happened on the way to making that change.  All of the training I was doing to prepare to become a coach reminded me of what I had loved about teaching in the first place.  I would like to say there was an “aha” moment, but it took months of agonizing before I realized that my day job could provide a platform for doing all the wonderful transformational work I wanted to do as a coach.

Thinking about that process, I have come up with five key questions you need to ask yourself if you are considering a career change.

  1. What attracted me to this job or business in the first place?  No doubt, at one point you were brimming over with enthusiasm and hope for the future.  Dig deep in your memories and remind yourself of the vision you had when you first started your job or business. When I started teaching, I was excited about being surrounded by interesting people and ideas, and helping to shape young lawyers to make a difference in the world.
  2. On a day to day basis, what did I enjoy about my job or business?  Make a detailed list of everything that you loved doing. In his book, The Big Leap, Gay Henricks calls this your “zone of genius” — the thing that you get so absorbed in doing that you lose all track of time.  For me, that included designing creative courses and lesson plans, spending time in deep conversation with students and colleagues, and providing pro bono legal services to low-income artists, nonprofits and entrepreneurs.
  3. What is getting in the way of doing more of the things I love, living in my zone of genius?  Make a list of all the things you dread doing, the tasks that leave you feeling bored and unfulfilled.  You might also have people who are energetically standing in your way — difficult supervisors or colleagues, demanding clients, or family members who want to preserve the status quo. If you read The Big Leap, you will discover that most of these things are simply masks for the hidden fears and anxieties that are holding you back from doing what you love.
  4. How many things can I shift to get more of what I love and less of what I dislike in my day to day work?  Can I create my own project, delegate tasks to others, or make a lateral move to another position?  The great thing to remember is that the tasks that you hate probably fall directly in somebody’s zone of genius.  Aim for the 80-20 rule — if you could spend 80% of your time doing things you love, think how much more fulfilling your work would be.
  5. Am I just moving away from something, or am I being drawn toward something even better? Sometimes the factors that are leading to boredom and ennui in our careers are bigger than ourselves. Circumstances change, people change, and what matters to us evolves over time. If you make all the positive changes you can in your job or business, but still feel called to pursue something bigger and bolder, the time might be right to pursue something new.  But that doesn’t mean you should just say “I quit” and walk out the door. You have invested a lot in your career or business, and you want to take the skills, connections and good will with you.  (More about that in a later post.)

If you are wondering how my story ended — it is still a work in progress.    For the short term, I found a way to build more of what I love into my current position.  I participated in a service learning trip which brought a group of students to Texas to help immigrant women and children in the Karnes County Family Detention Center.    I started blogging about social justice issues that are important to me, like the recent Supreme Court decision on marriage equality.  I am participating in a Cuba Study Group to explore the ramifications of the new U.S. policy to open diplomatic relationships with Cuba, and will be part of a delegation traveling to Cuba on an exchange program with the University of Havana Law School.

Next year, I plan to transition from my administrative position back to full-time teaching, running an Entrepreneurship Clinic for low-income and immigrant artists, entrepreneurs and nonprofit organizations.  At the same time, I am continuing to develop my coaching business, working with people who want to find more passion, meaning and fulfillment in their work. My life is once again very full, and very fulfilling.

Now it’s your turn. Life is too short to waste time feeling unfulfilled.  Answer these questions for yourself, and let me know what you discover.  And if you  need some help, use this form to request a free 30 minute breakthrough session to clarify your priorities for your career or business.


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