in the world in Adobe Flash. All the trappings of success, right? Turns out, not so much.
How did I get here?
I didn’t have the answer that morning, and it took several years and more than one painful lesson (including losing my first company to a corporate coup) to help me see how I’d trapped myself despite all my talents, passions, and work ethic. Once I’d lost the company, I pushed the reset button and reevaluated my world view. I changed my paradigms and took a hard look at my professional life from a more objective point of view.
That’s when the epiphany came. I’d been caught in a paradox—the Entrepreneur’s Paradox, to be more precise. In short, I was good at what I did—really good. But this was the reason my business wasn’t succeeding.
Think about it for a moment. If you’re highly skilled at something, people view you as an expert and want your hands-on efforts. Clients see you and not the business as the most expedient path to that “magic” you sold them in the first place. My clients were no different. They wanted me, Curtis. They weren’t really interested in the services of my business. I had employees, tools, and a few systems in place, but our corporate clients wanted me, personally, to do the work. After all, I had been the one doing the work for other clients in the past. As a young and inexperienced entrepreneur, I had made the mistake of assuming that “doing the work” and “growing the business” were the same thing. But they are as different as night and day.
With this new (and hard-won) insight, I realized that, if I wanted to succeed in business, I had to stop being the sole expert, the sought-after specialist, the best in the world. I had to give up part of my identity.
The Entrepreneur’s Paradox applies not only to me, but also to countless others who attempt the leap from world-class expert and specialist to business owner. You simply can’t be the best in the world at your craft while being best in the world at running a business. As the saying goes, “No man can serve two masters.” And that’s exactly what I, and most entrepreneurs, have tried to do.
Our personal passions are often at the heart of a new business venture. One of my friends is a chocolatier because of his love for chocolate. Another started a travel expedition company because she loves to travel and has a true talent for immersing people in unique cultural experiences. Another friend started a video game company because of his love and talent for gaming. Still another started a mobile app company because he has a passion for clean design and journaling and wanted to help people around the world tell their stories. Passion is great fodder for the entrepreneurial engine.
In the years between that first business epiphany and the writing of this book, I’ve coached many passionate entrepreneurs. Without fail, they all talk about how unique their business is—that they have the secret sauce that will differentiate and propel them past their competitors. And it’s often true. But what tends to always be true is the timeline these entrepreneurs will go through. Their stories are almost always the same and move in predictable chapters and verses.
All entrepreneurs start somewhere else in life. They usually start at an established company. Most get a little taste of entrepreneurship when they take a small break from the “normal” world. Instead of waking up each day to go to the same office and see the same boss and do the same thing day in and day out, they get a taste of something new and exciting, tapping into their skills and being rewarded emotionally and monetarily. It’s like taking a vacation to a tropical island where breaking waves offer adventure and pristine white sand beaches and which seems like a little piece of heaven. It’s exhilarating because it represents many of the things we enjoy and are passionate about. It comes with a rush of new experiences and we are often praised for our accomplishments there, because we are typically very skilled at what we do. Most will occasionally jump to the island for a fleeting moment of thrilling experiences and then bounce back from this “special” world to the ordinary, safe, and comfortable world (i.e., our day jobs). In today’s vernacular, this is often called freelancing, moonlighting, or even having a “side hustle.” Yet, we still feel the pull of this island and can’t wait to go back.
For others, this desire becomes so strong we leave the comfort of the ordinary world permanently—selling our homes on the mainland and moving to the island! At first, it’s a paradise. We wake up whenever it feels nice, set our schedule according to what suits us best, and have fun doing what we love. This is the life! And people really appreciate the artistry with which we build our sandcastles, fish for food, and make the most delicious coconut drinks (i.e., the products or services we offer). Even better, the demand for our products grows.
Then, one day, as we are sitting on our beach chair, we hear a rustle in the vegetation from behind. We turn to catch sight of an alligator creeping out of the jungle and heading straight for us! The alligator threatens our livelihood, peace, and food. Springing into action, we’re forced to wrestle it away from our beautiful beach and the delicious fish cooking over the fire. Not only will this beast crush our castles in the sand, but it will deprive us of food and all we’ve accomplished. The alligators show up in the form of unrealistic deadlines, unplanned emergencies, keeping customers happy, cash flow issues, and a host of other activities that require our time, energy, and focus. We didn’t realize life on Entrepreneur’s Island came with a cost! When we saw the shimmering blue ocean waves, we had no idea there were alligators native to our little patch of paradise.
Over time, more alligators begin to show up. It seems the longer we live on the island and the bigger the fish we reel in, the more alligators we attract. Long gone is the fantasy of sipping drinks from coconuts and basking under the ocean sun. Instead, each day brings a new assault and a greater struggle to wrestle these alligators away. The cost of maintaining life in paradise is to spend a greater portion of each day wrestling these unwelcome intruders. And to make matters worse, it seems that when one gets a bite, it attracts even more!
Fed up and tired of being surprised day in and day out, we decide to find the home of these alligators and deal with the problem head-on. That means leaving the beach and entering the jungle. If it can keep our beach safe, it’s worth the effort. Trudging through the dense brush, we find the swamp the alligators call home. There’s little choice but to jump in and start wrestling, and this is how we spend the majority of the day: resolving client concerns, answering emails, returning phone calls, reconciling bank accounts, filing taxes, finishing projects, fixing projects, looking for new projects, scheduling travel, building a website, invoicing…the list of alligators is nearly endless. But we wrestle them one by one, even though it means returning to the beach later and later each day. What’s strange is that we actually become quite good at wrestling alligators and keeping them off the beach, even though it’s a beach we see less and less of.
This isn’t where we wanted to be when we left the comfort of a stable job. We wanted to be in a place of freedom, flexibility, wealth, praise, and excitement. Well, we got the excitement for sure. We’ve entered our personal version of Groundhog Day: wake up, wrestle alligators, go to bed, repeat. It’s exhausting and doesn’t feel like that magical island we sacrificed everything to move to.
“Alligators: The urgent demands and important tasks incumbent to running your business and which can’t be ignored.”
Entrepreneur’s Island is made up of an idyllic beach where you wanted to spend your time, a thick jungle with a swamp full of alligators you were forced to wrestle, and several tall mountains in the distance you hardly noticed (if at all). So after months (or years) of wrestling alligators, it’s
