“Life is too short not to be doing what you love,” said the woman whose words changed my life. Those words turned me into an entrepreneur. We all have stories about the moment we knew that we were destined to build our own businesses or craft our own careers. Mine starts with those words, spoken at just the right time, by just the right person.

The Right Moment

It was a little over 6 years ago. I was working a job that didn’t make sense to me. I had recently moved to a new city. I had fallen into unrequited love and had begun immersing myself in the eclectic San Francisco poetry scene. To put it politely, I was exploring life and trying on different parts of my personality. But in all honesty, I was a little lost, and mostly rudderless.

The Right Person

It was my Grandmother’s 90th birthday, and I was visiting her Florida home. My gift to her: a CD of some of my latest poetry. She had always loved poetry. She had even written a couple books of poetry with my Grandfather before he passed. I had just gotten through telling her about my job, which didn’t make sense to her either. Then I played for her the CD. By the third track she began to tear up. By the 7th, she was smiling in amazement. When the CD finished with my favorite piece, she turned to me with a look of concern on her face. “What are you doing?” She spoke these words as if she was upset with me. “What are you doing with yourself when you’re not writing poetry?”

I couldn’t really answer her question. When I was writing, my world made sense, I was being creative, passionate, and deliberately attentive to detail. When I was not, I was mostly just getting by. In poetry, I took risks and stretched beyond my comfort zone. In everything else, my job, my love life, my friendships, I was playing it safe, waiting for something to happen, unable or unwilling to take action.

The Right Message

“You’re too good a poet to be wasting your time.” Those next words took a while to sink in. While my Grandmother loved my poetry, she was more interested in what drove me to write it, my passion, my creativity, and my desire to reach beyond my abilities. My Grandmother knew that I was a risk taker. It’s not that she wanted me to write poetry for a living, she just didn’t want me to give up on these qualities everywhere else in my life. But she could see on my face that I wasn’t quite understanding all of this, so she delivered the final line of her life-changing stanza.

“Life is too short not to be doing what you love.” When your Grandmother says this to you on her 90th birthday, you listen. I went home, quit my job, and began my life as a risk taker, letting the inspiration behind my poetry become the inspiration fueling my career. I went back to my first love, teaching and learning. I started talking to fellow entrepreneurs, generating ideas, and researching their feasibility. I had some setbacks along the way, times when I wanted to give up and just play it safe. But my Grandmother’s words echoed even louder in the moments when my inspiration grew quiet. I was no longer lost. I just needed a direction, somewhere to channel all my energy. I just needed a muse.

The Catalyst (aka: The Kick In The Pants)

Flash forward to my Grandmother’s 95th, just last year. Again, I was at a crossroads in my life. I knew I wanted to build a career in the field of learning and technology. But was I willing to gamble on grad school and a return to Chicago, or should I just keep plugging away at my teaching job in San Francisco. This time my Grandmother had some poetic words for me.

“Are you doing what you love?” She asked me.
“Almost.” I responded.
“What’s missing?”
“Confidence.” I said, weakly.
“Oh, you mean fear.” She replied.

Risks are not born out of confidence, they are born out of fear. If we aren’t afraid both of what we are building and of a life lived without creation, then we have no fuel to power us through our moments of self-doubt. It is fear, not confidence, that drives us forward. It is fear that fuels us to entrepreneur: to dream, to be unsatisfied with dreaming, and then to build our dreams.

We all have a story of that one right message, delivered at just the right time, by just the right person. Mine came from my Grandmother, not once, but twice. I learned to listen for my fear and then passionately pursue it. How about you? When you think back to the beginning of your career as an entrepreneur, what comes to mind? Was it a friendly and familiar voice, or a simple event that lent itself to epic interpretations? What fears drive you forward in quiet moments and who is the source of your wisdom?

Life is too short not to be doing what you love. Tell us the story of what you do, and why you love it. Email me if you’re interested in being one of our next Entrepreneurs in Spotlight.