While making my way through high school and college, my most definitive quality was my industriousness. I was willing to work day and night for some hard-earned money, and was not inclined to shy away from any opportunity. When my older brother was seventeen, he proposed starting a landscaping business, and I was eager to get involved. My two brothers and I—we were all very close in age—joined together in a feat that showcased the energy and vitality of youth and built a business that, had its construction been coupled with planning and foresight, could have made all of us a lot of money, and my teenage dreams come true. The business had rather humble beginnings, to say the least. We transported the tools of our trade—a 3- horsepower Jacobson lawnmower, a gas can, and a broom—from lawn to lawn on our bicycles.
Through diligent hard work and very low prices, we acquired about ten loyal customers over the first year. As our business continued to grow, we gradually upgraded our homeowner lawn equipment to more impressive, commercial models. Hungry for more success, we also started an aggressive advertising campaign, plastering our flyers all over the houses, car windshields, and grocery store bulletin boards of the surrounding neighborhoods. Everyone within a fifteen mile radius knew that we would be more than happy to mow their lawn. Before anyone, including ourselves, knew it, we had over a hundred accounts and a business with a great reputation that included five local towns. That’s not too bad for a few hard-working kids in their late teens and early twenties who’d started with bicycles and a 3-horsepower mower from their garage.
Building that business came with many benefits; at least, that was how we saw it. We earned excellent money which helped us build up a remarkable amount of equity; in addition, we stayed in good physical shape and got great tans—working outside for thirteen hours every day in the spring and summer helped us develop the best color anyone could hope for in the northeastern part of the United States. Best of all, we were our own men. We had our own business, which allowed us to make decisions for ourselves, employ people, and feel a strong sense of freedom. Despite all that potential, I remained stuck in the moment. I never asked myself if I wanted to be a landscaper for the rest of my life, or if there was a way to use this business to get closer to achieving some goal that I had set. More importantly, no one ever sat me down and talked to me about all the ways in which this business could have been a great tool for me to get where I wanted to go.
Everyone in my advice pool—parents, siblings, other relatives, friends, customers, business associates—neglected to step in to ask me what I was expecting to do with this business in the long term. They never asked me what I wanted from it, or even sought to remind me that there was potential in the business I had worked so hard to build but had not thought at all about the future it might have contained. In the end, it was my lack of guidance as a young man with a large amount of expendable income that led me to squander my money on transient pleasures like vacations, cars, and girls. I often think of all the possibilities I missed, and what I could have done if I had the opportunity to do it over.