What’s Your Biggest Regret? Mine is….

Biggest regret video

They placed a blackboard in NYC and asked people to write down their biggest regret in life.  There was a very common theme in all the regrets: they were for things NOT done, actions NOT taken.  What is your biggest regret in life.  It is not living the life you were meant to live?  It’s never too late to start.

My biggest regret is spending the last 25 years not pursuing my true passion.  I did a great job of convincing myself that my passion was business.  Turns out that was programming from childhood and society.  My grandparents had always wanted me to be a doctor.  My father and grandfather both worked in hospital administration, so it was natural for them to want me to become more than they were.

My father (later) and stepfather were also entrepreneurs in the restaurant business.  While I started on a college track in pre-med, after a couple years I felt the tug of entrepreneurship and left to open a chain of pizza delivery restaurants.

I really did enjoy the work, but looking back the parts I enjoyed most were those moments of inspirational leadership.  Leading a crew on a busy Friday night, or inspiring my employees to take on new challenges and watching them accomplish more than they thought possible, was what filled me up.

But somehow that got drowned out in all the other distractions of business.  Designing products, raising money, creating strategy, and marketing and selling all required an immense amount of energy and effort.  There was enjoyment in all of it, but not the soul-satisfying fulfillment of inspirational leadership. The entrepreneurial community is a powerful force.  There are magazines and conferences and an entire culture dedicated to helping entrepreneurs learn the skills they need to be successful.  Like most industries, their measures of success are generally monetary, and definitely external.

I remember a moment in 1996 very clearly.  I was at a conference called the Birthing of Giants.  It was a 3-year program put on by the Sloan School of Management at MIT, the YEO (Young Entrepreneurs Organization) and Entrepreneur Magazine.  Was was one of only 60 entrepreneurs under 30 in the program out of thousands of applicants.  It was a pretty selective group.

I was sitting in “class” on the first day of the first year, and we went around the room and introduced our businesses.  It struck me how most people measured their success by how many employees they had, and how fast their employee base had grown.  As I listened, all I could think of was that people are measuring their success by how fast their overhead was increasing.  At the time I thought that was foolish.

But now looking back, I realize that everyone was probably suffering from the same malady.  We all needed something more fulfilling to our souls than growing our revenue.  And employing people was the closest we could come to tying a measurable success metric into something that satisfied that deeper yearning.

Society as a whole holds entrepreneurs in high esteem.  My ego was constantly fed by all the media attention my company received.  I was featured in the Wall Street Journal, Forbes and Fortune, as well as the local business section of the newspaper.  My soul was only occasionally fed by those fleeting moments of inspirational leadership when I was in front of the company, or on stage at a big conference, and having people come up to me afterwards to tell me how motivating to them I had been. Quietly waiting for recognition in the back of my consciousness, however, was the desire to act in community theater, or try stand-up comedy, or become a motivational speaker.

It wasn’t until something shifted inside of me in the last years that I even recognized something was wrong.  You might know that feeling; the wonder if this is all there is? Is there more to life than going to work, making money, watching your kids grow and leave.  As that feeling grew stronger, I somehow developed the courage to tap into it and make the leap to something else, even having no idea what that something else was at the time

For many people, this awakening turns into a mid-life crisis.  They are afraid of facing themselves, and therefore turn back to what would have made them happy when they were younger.  For some it’s fast cars, others look for younger women or men to be with.  But it’s that search for something external that is the hallmark of the mid-life crisis.

For me it’s been more what the psychologist Carl Jung described as the Middle Passage.  It’s the willingness and ability to look inside ourselves to determine what our souls need to be truly happy.  I’ll be writing more about that soon, and even plan to launch a new blog dedicated to that transition.  If you want to get some good background on the subject, I recommend the book entitled The Middle Passage by James Hollis.

This journey has led me to some real epiphanies.  It’s amazing how deep down in our subconscious we bury what we truly want when it’s not something that is generally accepted by our families, our communities, or society in general.  I can imagine what the reaction from my family and friends would have been if instead of heading to college to (pretend to) become a doctor, I packed up and moved to Hollywood to try my hand at acting.  Instead, I did what was expected of me.  Sound familiar?

The realization that I had succumbed to programming when I was younger has given me the freedom to to tap into what will ultimately make my soul happy.  And with that in the forefront of my consciousness, I can start to plan the steps to become what I was meant to be all along.  Thankfully it’s never too late.  I look forward to sharing it with you. Thanks for coming along for the ride.

Do you have regrets? We all do.  Leave your biggest regret in the comment section below and let’s build our own blackboard.

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