HEMP Mentor Maxims: Are You Playing Checkers or Chess?

I started my business like most business owners do. I spent 10 years learning the trade, working for other people, then struck out on my own to set the world on fire with brilliant advertising — helping our clients succeed and, in doing so, growing a great agency. As many business owners learn, it’s rarely as easy as it seems.

The first 14 years of Meers Advertising could best be described as anything but consistent. For seven of those 14 years, I didn’t take a salary, convincing myself it was better to pay my staff in the hope we would grow the company to the point where I could pay myself. We rode an annual roller coaster of client wins and defections. We were inconsistent with our product, our service and our customer experience. It’s a wonder we stayed in business at all.

I was a small business owner working to convince myself I was an entrepreneur. I was making tactical moves, selling whatever I could sell to make money. While we often developed sound business strategies for our clients, we were not developing sound business strategies for ourselves. Eventually, in 2008, we hit the wall. That’s when I learned the important difference between being a small business owner and being an entrepreneur.

In February 2008, we found ourselves at the bottom of one of the deepest roller-coaster loops we had ever taken. Candidly, as we were headed down the slope, we couldn’t tell if there was a track heading back up—or if it would run off a cliff. It was very dark at the bottom of that dip.

Even though I had been through many roller-coaster rides before, fortunately, this dip was enough to make me pause. For about six weeks, I pondered whether or not to sell the business, close the business or reinvent it. At the same time, I was reflecting on the mistakes I had made in the previous 14 years.

I had been operating the company as a small business owner. I was playing checkers. I moved deliberately and with intention, but I was making one move at a time, waiting to see what my clients did before I made my next move. It was a simple game. And I was playing it as I knew how—tactically. It’s hard to inject strategy into checkers.

The dip of 2008 helped me realize an important difference between small business owners and entrepreneurs. Small business owners play checkers. Entrepreneurs play chess. They examine multiple moves at one time. They put multiple ideas in motion at once, and then watch to see which ones are successful. They take calculated risks.

Could I have emerged as an entrepreneur without hitting the wall in 2008? Doubtful. Sometimes it takes a cosmic two-by-four up side the head to be the wake-up call people need to make significant change in their lives. It also takes the cumulative experiences of doing it the wrong way for 14 years to really understand the benefit of doing it differently.

The longer you are in business, the greater the opportunities to learn. I learned it was time to play chess—a far more challenging and interesting game, the game of entrepreneurs.