What Steve Jobs Taught Me About Career Fulfillment

In Steve Jobs’ now famous 2005 commencement speech at Stanford University he was sharing his life lessons with the graduating class. And he encouraged them to trust that all the things they do with their life will somehow all come together in the future and that this belief should give them the confidence to follow their hearts when it leads them off the well-worn path. Certainly easy for him to say as the co-founder of Apple.   

This message served as the inspiration for a recent Toastmasters speech I gave about my career path where I connected my own dots to see how they’ve led me to where I am today.

Currently I serve as the Senior Associate Director of Career Services at New England Law Boston and run my own career coaching service. When I think back to the beginning of my career I can see how everything I experienced prepared me for where I am today.

My Favorite class

In college, my favorite class was Organizational Behavior which is essentially the intersection of psychology and business. I loved learning about how companies create amazing work place cultures and motivate employees. I was also introduced to one of my all-time favorite books, The 7 Habits of Highly Effective People by Stephen Covey, which taught me how to be proactive and take responsibility for my life among many other lessons. Little did I know that in this course, the seeds of personal development were being planted, and that it would become the focus of my career almost 20 years later.

looking good but feeling empty

But as life would have it I had to get lost before I could find myself. After college I sought jobs that from the outside looked like they would be fun but in reality they didn’t provide any sense of fulfillment. I reasoned that if I had to work, I wanted my work to be fun and exciting. Using this criteria, I landed a string of "dream jobs," first in sports marketing at Reebok, then at a major talent agency in Hollywood, and lastly as an entertainment lawyer at a record label in New York City. These jobs were certainly fun, the work was interesting, and working with celebrities was a nice perk but they never gave me the sense of fulfillment that I craved from a career.


Feeling unfulfilled, I found myself constantly searching for something that would fill this void. I knew I didn't want to go back to school to get another degree, and I certainly didn’t want to just jump to a new and equally unsatisfying job. I resolved to sit tight, and continued to practice law while simultaneously following my curiosity into the world of entrepreneurship and personal development. I had no intention of starting my own business or becoming a coach. Rather I was drawn to those worlds because there was a sense of freedom and fulfillment that I saw in those communities that I didn’t see in other industries.

As I took more personal development classes, I began applying what I was learning to my legal career. I found my legal work to be more rewarding because I was connecting with my clients on a much deeper level. Their legal issues were symptoms of problems in other areas of their lives, and I was able to help them address those issues so that their businesses would flourish. Ultimately, I recognized that I enjoyed the coaching and counseling aspect of being a lawyer significantly more than I enjoyed the legal research, contract drafting, and litigation that consumed most of my time. It was this realization that led me to consider that it was time to leave the law so that I could focus my efforts on coaching. I knew I had finally found the thing that I was looking for, the "missing piece", that filled the void all my previous jobs could not do.


But leaving the law was easier said than done. While I was relieved to have finally identified the missing element in my career, I was plagued by fear about how to move forward. Was I really ready to walk away from my legal career? How would I build a career as a coach? I struggled with doubt and uncertainty even as I dreamed of following a more fulfilling path. My transformation didn't happen overnight; in fact it took another two years of careful planning and preparation to successfully transition into my coaching career.

After I left the law I became a legal recruiter, gaining the experience, skills, and insight to understand the hiring process from both the perspective of the employer and the lawyer in search of work. I moved back home to Boston and through my network found a job working in career services at Northeastern School of Law. There I began teaching courses that combined personal development and career development which led to me giving a talk on career development at New England Law Boston, my alma mater. Soon thereafter New England Law offered me a job to join their career services department.

Today I can happily say that I love what I do and it has nothing to do with having a flashy job title or working for a name brand company.  It has everything to do with what I get to do every day, counseling  students and clients and the feeling of satisfaction I get from helping them achieve their career goals.

From where I stand, it seems I have come full circle in terms of my career back to my personal development roots, but I could have only ended up here after taking such a long and windy road. The journey, often uncertain and frustrating, was an invaluable experience. Getting lost, learning from my mistakes, following my curiosity, and struggling to find my way professionally makes me uniquely suited to help people discover their talents and forge their own path. As Steve Jobs nicely summarized for us, connecting the dots certainly allows you to make sense of your past in a way that gives you hope for the future.


If you would like to learn how to design a more fulfilling career you can download the Career Design Guide below.

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