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Halloween is the Entrepreneur’s Holiday

Halloween and Entrepreneurs... perfect togetherThe optimistic entrepreneur might think the holiday that best reflects them is Christmas, where no matter how bad the economy is you’ll have millions of customers with wads of cash burning holes in their pockets. The more pessimistic entrepreneur might consider New Year’s to be the most reflective – a new year, with all the unknowns that entails, and generally the toughest time to get sales. Personally, I think the holiday that best reflects the life of an entrepreneur is Halloween. Here’s why…

As a young kid, your parents pretty much dictate your Halloween. They pick the costume to buy/make, they take you trick or treating, they go through your candy afterward and toss what they don’t want you to have. They have the control, you’re along for the ride. This is kind of like your first job after school, where you do what the boss says and generally have little autonomy.

Later on, as you get older, you start deciding on your own costumes and going trick or treating on your own, or with friends. Now the holiday really sings, because you’re just rolling in the candy and your only limit is how long you want to stay out. This parallels the first attempts at entrepreneurship. Think of it, you can be just about anything you want to be! You also pick the crowd you want to run with, one that you think can help you get the most return for your time investment. Everything you do is a blast, and you’re raking it in hand over fist. Sometimes your company (like your costume) is a real killer and generates lots of buzz, and sometimes it’s pretty ordinary and your success is dictated by your stick-to-it-iveness. Either way, these are the fun times.

Unfortunately, there comes a time when you decide you’re too old to trick-or-treat, and your Halloween activities evolve to more social activities like parties. Similarly, business owners with some success under their belts find that the initial surge of growth has slowed and they need to evolve how they operate in order to continue to grow and survive. New products, new processes, new hires… all are evidence of the abrupt realization that their businesses are too old to still act like a startup.

If you make it far enough, you eventually find yourself married with kids of your own, and the process starts all over again with them – just like with businesses. You might sell out and start over, or buyout a competitor, or expand your territory or product mix… You’re the one in control now, and you can pick your own path to success.

Or, if you prefer, you can just sit at home and eat a giant plastic pumpkin full of candy.

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