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What Should Keep You Up At Night

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This article is more than 9 years old.

A few days ago, I met with a student over coffee. She asked me the age-old question, “What keeps you up at night?”  After pondering that for a few seconds, I finally came up the correct answer to that question, “Nothing.”

While I know she was referring to challenges that a growing business deals with, I wanted to instill one small lesson. You have to be able to sleep at night. You have to be able to put the computer down. And you have to be able to mentally and physically shut down - and actually sleep!

I’ve learned this lesson the hard way over the past few years. My mind used to race every single night, and I could not sleep. It started as excitement, but at other times it was worry as well. For example, we messed up on a customer order, or we were fundraising and cash flow was tight. However, at those moments around 11pm, there was nothing I could do to change it. Instead of thinking about it until 2am, it was better for me to sleep and deal with challenges in the morning.

In another conversation with a potential investor, he asked me a similar question. He asked, “What things could cause your business to fail?” To me, this was a great question. He was really trying to understand the challenges that our business could face in the future. He was not asking about how I managed stress or what little things bother me.

After I answered the student with “nothing” I went out to explain a bit more in our conversation. I said that you will never be perfect. I wish our tailoring rate was 100% accurate, but we do make mistakes because we are human. I wish that fundraising was simple, but it’s selling and selling take a lot of work. I wish that cash flow was super simple in business, but as any business owner can tell you, it is not. Instead of letting that keep me up at night, I sign off every night and go to sleep. When I wake up the next morning, I’m refreshed and ready to conquer those problems.