Entrepreneurs: Don't Get Too Comfortable

There are many 3 a.m. issues that I think you face as an entrepreneur. Personally, we’ve got two offices with a bunch of employees. My 3 a.m.’s are always: how much bigger can you get being one of the largest independent shops in Canada? Can you double, triple? Is that even physically possible in this environment? My 3 a.m. issues are if I should have done this writing yesterday for this book idea that I have so that’s my resistance of putting my ass where my heart is type of thing.

Most of the stuff is around that and I sort of shore it all up into the entrepreneurial spirit, really. Once an entrepreneur, always an entrepreneur. If you’re not waking up at 3 am, that’s actually when I start getting concerned. When I start worrying that I’m getting comfortable, that things are too good. So even when things are going great, I get very, very panicked and it may not be physically healthy for me and my family, but I think it keeps me somewhat sharp and somewhat aware of the fact that it’s very elusive and it could leave at any moment, and if it could leave at any moment, what I am doing to make sure it doesn’t leave?