Why Your Story is Your Biggest Motivator

When was the last time you asked yourself why you're doing what you're doing? I can cram my day with lots of tasks, and on good days I accomplish them all. But if at the end of the day I have lots “done”, and I’m no clearer on why I’ve done it, it creates a certain flavor of angst and confusion.

I’ve realized that these existential crises tend to rear their heads when I’m out of touch with my story—the WHY behind all the busyness. Simon Sinek perhaps single-handedly challenged an entire generation of TED viewers to “start with why”. His talk still resonates almost 10 years later.

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In marketing speak, your story helps you define your unique sales proposition, your key differentiators, your brand positioning, blah blah. But what I’m coming to understand in a very visceral way is that understanding WHY you do what you do is the key factor in keeping you productive and happy in your business even when things get tough.

I ran a story workshop for artists a few months ago. I taught them about story structure, the science behind story, and how it can help their sales. My pitch went well, and they were all on board. They knew they “needed a good story” to grow their business. But the most interesting thing that happened that night was when I asked the question, “What happened to you that you now do what you do?”

With this simple question I was inviting them to uncover their story. And it became clear after asking that the vast majority of the people in the room had never been asked that question. They had never asked it of themselves either.

It’s easy to get caught up in the busyness of business: managing a website, accounting, client calls, email, creating products, Adwords dashboard hell, creating videos, etc. And we can’t forget to keep asking ourselves the important questions to keep us motivated, honest, and inspired for the marathon of hard work that continues to unfurl in front of us everyday.

Our story is our biggest motivator.

I used to think I knew my story. “It’s just a natural next step from all the other things I used to do!” But that’s not a story. That’s a cop out. That sounds like my life is driving me, not the other way around.

Mom, Dad, and Jennifer in Vienna, 1978

Mom, Dad, and Jennifer in Vienna, 1978


So I started asking myself, why am I so concerned with what business owners say about their business and how they say it? Why do I care so much about helping them communicate better? Why is it so important for me that people connect? The answer that came was hard to accept because it’s a painful story.

I come from a very fractured family. My mom and dad split up when I was 17. My dad, after 12 years of living with my sister, my mom, and I in South Texas trying to support us with his fledgling opera company, came out as gay, packed his bags, and moved to Chicago.

It seemed sudden, but it had been coming for a long time. My parents fought constantly, and there was a pins and needles quality to our home. After my dad left, my mom, sister, and I had a brief period of peace and actually enjoyed each other’s company. Then I went away to college, and that’s when the factions formed.

Mom, Jennifer, and me, Colorado 1979

Mom, Jennifer, and me, Colorado 1979


My dad and I were in touch, and I was in touch with my mom and sister, but a deep, painful rift had begun that year in my family that continues to widen to this day. My mom and sister haven’t spoken to my dad for almost 10 years. I’m the only one who speaks to everyone. I am the emotional conduit, the communicator, the connector.

The few times I’ve attempted to share this story with others, I have struggled to finish for the giant lump that forms in my throat trying to choke back tears. When your story is painful, it takes time to be able to tell it without the emotion taking you over. I’m not there yet. But I’m thankful I know why I do what I do even if I am still unable to communicate it well.

It seems helping others communicate their why is the warm up to my real work—sharing my own story. By continuing to dig deeper into my own experience I feel more connected to my work, and I feel more motivated to move the big stones in my day, even on Mondays.

So what happened to you that you now do what you do? What story are you telling? These are not just questions that will help you in your marketing; they’re the questions that will help you understand your life.