The Story of Entrepreneurship: How What You Tell Yourself Influences Your Success

As a small business owner, I am often asked, “How did you know entrepreneurship was for you?” For folks like Gary Vaynerchuk, he would say that he’s been hustlin’ since he was 16 with the itch, the desire, the unbearable passion to be his own boss. For me, my story is a bit different. I initially set out to be a chiropractor… and then a sports reporter… and then a teacher… and finally a marketer. Entrepreneurship chose me and I truly believe I am doing what I was designed to do.

History Repeats Itself Because No One was Listening the First Time

This story really begins when I was laid off as a brand manager for an inspirational speaker and sales coach back in 2013. Talk about an unexpected date with reality and a large slice of humble pie. I had no idea it was coming (despite all the signs being there) and left with that cold, hard, unforgiving feeling of rejection. In my mind, it was that experience that moved the needle for me. I felt, for the first time in my life, that burning desire to control my own livelihood; anything to avoid that feeling of rejection again. I believe most budding entrepreneurs feel the same way — if you’re going to fail, it will be on your own terms, not someone else’s.

After being laid off, I decided I would try the freelancing game for a bit. That first couple of months continued to provide a full spread of humble pie, plus humble bread and humble hors d’oeuvres to fuel my humility game to no end. I recall sitting in a meeting with what I presumed would be two business partners and the duo reaming me about the terms and conditions of a contract that I was proposing. I left the meeting feeling embarrassed because I didn’t understand some of the legal terminologies that had been discussed. Needless to say, no business transactions ever took place as a result of that meeting.

After that, I began asking for recommendations and discussions with those that had been in the freelancing world for a while and had a handle on how to play the game.  In this way, I changed the trajectory of my story. Instead of listening to the embarrassment and lack of insight I was facing, I turned to others whose stories were about success and took their lessons as my own.

Burn the Ships to Remove the Option of Retreat

Thanks to digital technology, I was connected with some amazing folks in the Boston and Dallas areas that really helped open my mind to business and the possibilities that underpin the American Dream. Since then, I’ve had the pleasure of working with some of the biggest and brightest business leaders, and experts that have provided some of the best advice I’ve been able to apply directly to my business. I often hear the colloquialism, “If you want to go into business for yourself, you need to just take the plunge and dive into the deep end.” Touché.  

I would describe my own experience as much more strategic. We pulled the ship right up to the dock and stepped off, while simultaneously burning all the other ships in sight, just as Captain Hernán Cortés supposedly did in 1519 when he ordered his men to burn the ships upon arrival in Veracruz, Mexico as they embarked on their new journey. The logic? Retreat and procrastination are easy when you have options. When you eliminate all outside options, you’re forced to commit to a singular goal and deal with challenges head-on.

For me, this metaphor has helped me “make the jump” to full-time entrepreneurship in a much more thorough way than thinking about jumping into a body of water head-first. Instead of relying on “faith” to get me through “falling off a building,” I am actively destroying any option of retreat for myself. I have to move forward, and the decisions that I am making are propelling myself and my team in that direction.

Understanding Challenges Through Storytelling

According to the Small Business Association, only 30% of new businesses fail during the first two years of being open, while 50% fail during the first five years and 66% during the first 10. The number one reason small businesses fail? Lack of market research and understanding what challenges are lurking around the corner. For LuckyTamm Digital Marketing, one of our biggest strengths is understanding the importance of market research and planning for the reason that the SBA noted above.

The reason this is the case is because we’re storytellers. We like to know the who/what/when/where of an organization and industry before jumping into a lobster pot. Our three-step process 1. plan 2. activate 3. evaluate serve as a roadmap to helping clients pivot in the right direction when it comes to their marketing programs. We operate under the belief that we are a product of the story we tell ourselves every day. Stories are powerful measures that connect us as humans and transfer experience from the teller to the listener.

At LuckyTamm Digital Marketing, we work on our own stories as much as we do our clients’. We firmly believe that the stories in our heads define our success as much as the work we do. This helps us center ourselves, remove the ego from our work, and get stuff done.

As I continue to redefine myself as an entrepreneur, I recognize the story isn’t finished yet. I’m still writing it. This means I have an opportunity to burn the ships, consult with others, or find new ways to do old things as they come along.

Need help telling your business’s story? Get in touch with one of our team members or myself and we’ll be happy to roll up our sleeves and figure out how to assist you with your marketing/communication problem.