Gambling on Your Livelihood

As small business owners, many of us feel like we never get a day off. Sure we may take a day here and there or even try to take a real get-away vacation from our businesses, but work is never far from our minds. Last week I drove with my friend Lisa to Connecticut, where we spent the day at Foxwoods Casino and I tried - albeit unsuccessfully - to truly take a break. I had a great time and so did Lisa, who had taken a day away from her job as a spa manager. But I found it was impossible to avoid checking and answering my email and phone calls at regular intervals. Lisa and I were both disappointed that I couldn’t put work aside for the day, but ultimately, I know that my business grows in direct proportion to the energy that I put into it. While Lisa can go back to work the next day and pick up where she left off, what I leave undone directly impacts my personal income. The stakes are so much higher when we work for ourselves.

And what Lisa didn’t know was that even when I wasn’t responding to customers via email, my entrepreneurial mind was spinning the whole day. Being away from my home office always inspires me to think differently and while walking around Foxwoods, it was easy to start drawing parallels between gambling at a slot machine and the day to day life of an entrepreneur. Whether it is deciding to invest in a new product line, or investing in a new sales venue or platform, putting out a chunk of change to hire a contractor to design or upgrade our websites or to invest in marketing campaigns, it is always a gamble. As an Educational Specialist trained by eBay, I always remind my students about the psychology of the bidding process on eBay and the different reasons consumers shop on eBay. I remind them of the successful eBay ad compaign: “Don’t just shop – win!”, that more than hints that there is more complexity to a consumer’s thought process when they make a purchase than simply buying something. And as every eBay seller knows, when we create auctions with low start prices that could sell at a loss, in order to draw customers in to our stores, we literally are taking risks with our livelihood every day.

Interestingly, my friend Lisa is a much more aggressive gambler than I am, and at Foxwoods I watched with awe and fear as she placed one lusty bet after another, throwing caution to the wind. Meanwhile, she laughed at my much more conservative bets, saying, “You’re not gambling! You’re playing!” Interesting words. They brought to mind the words of motivational speaker, Jay Wallus, who I had met recently at a Small Business Development Center workshop, the Art and Science of Selling. During the workshop, he said, “As a business owner you have to go all in – you can’t play one chip at a time.” Even at the time, his words had caused a small shudder to run down my spine. And here those words were brought up again eerily at Foxwoods. I mean, I agree with the concept 100%. As Jay Wallus says, “If you go all in, the universe will respond to you.” But how much risk is okay to take?

Small business owners have to be very brave to survive but it can still feel risky to put ourselves out there every day. Even though I have a solid business plan, when I have a bad sales day, it can be easy to let fear have its way with me. In the back of my mind, I fear that I won’t be able to sustain the highs and lows of my small business, that I will have to pound the pavement to look for work, having to return to – gasp! - public school teaching. At my worst, I imagine myself dressed in rags and covered in cats, pushing a shopping cart full of my meager possessions down some dark alley. You get the idea.

I usually get my perspective back pretty quickly. I remember that everything goes in cycles and that I have made and continue to make wise choices for myself and for my business. And I am always left with pride and an acute awareness of the gambles I have taken in this unstable and volatile economy. Why? Because I was willing to take a risk on myself. So, maybe I do play one chip at a time, but I am still gambling.

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