10 Signs You Might Be a Serial Entrepreneur

I’m a bit of a weirdo. I’m not afraid to admit it and everyone who knows me would probably agree. I suffer from a condition known as serial entrepreneurship. It can be a blessing and a curse at the same time, but those of us who suffer from it are not looking for a cure. I decided to do a little self-analysis to identify the symptoms of serial entrepreneurship and the result was the following list.

1. You don’t use an alarm clock
I can’t remember the last time I set my alarm clock. I’ve never needed to. I generally wake up around 4:30 each morning (even on weekends and vacations). I usually force myself to stay in bed til 5:30 or 6:00 simply because I know how important sleep is and I feel like I need more, but the desire to get up and start my day somehow supersedes my desire for sleep. It’s not because I feel like I have to get up, it’s because I want to get up. I don’t want to miss any part of the day!

2. You question everything
I’ve always questioned the status quo. I’ve never believed that you do things a certain way because the so-called experts say should. I listen to what they have to say, but then I analyze it over and over again to understand why. I constantly ask myself if there’s a better way to do it. I even do this with myself. Just because I’ve done something a certain way for the past 5 years, doesn’t mean it can’t be done better. I challenge myself and the people around me to always find better ways to do things and to question traditional methods.

3. You love competition
I turn everything into a competition. The other day, we started talking about paper airplanes in the office (don’t ask me why, I have no idea – see symptom #7). Suddenly I had turned this into a contest to see who could make a plane that would go the farthest. I didn’t just want to win; I wanted to build the greatest paper airplane ever. Even once we were done and I had declared myself the king of paper airplanes, I spent the next hour trying to get my plane to fly even farther. In fact, most of the time I find that I’m competing with myself. How can I do x,y or z better? How can I become a better manager, business owner, community leader? This desire translates directly into being an entrepreneur.

4. There’s no such thing as enough
I’m never satisfied with where I am. I always want more and I don’t necessarily mean more money. I simply want to get better. I want the company to keep growing. I want to innovate more. I want our website to be more user friendly. I want to be able to offer more to our employees. I want to offer more to our customers. I want our customer service to be better. The list goes on and on. I have a hunger that is insatiable. It almost seems as if the more I do, the more I need to do.

5. Even when you’re tired, you can’t rest
Like everyone else, I get tired. I get burned out, I need a break. There are days when I go into work and I tell myself “I’m going to leave early today, sit on my porch, drink a glass of wine and watch the dogs play in the yard – I need a little break”. This always seems like a great idea. I tell myself that I’ll leave around 2pm. Next thing I know, 2pm rolls around, then 3pm, then 4, then 5. I’m still in the office and for some reason, I’m not tired anymore. Usually it’s because I’ve found something to do that I’ve become totally immersed in and I don’t care about time anymore.

6. You need to know everything about everything
With everything I’ve done, I seem to have this need to understand everything about it. When I played sports, I not only needed to understand the responsibilities of my positions, I needed to understand every position. When I started taking guitar lessons, I wanted to understand everything about music theory. The same thing holds true today. I can’t just accept that things happen. I need to know why and how they happen. I think this has a little bit to do with symptom #2.

7. You’re always looking forward, never backward
Ask me what I did on my birthday last year or to name one of my high school teachers and I’ll draw a total blank. It can actually be embarrassing sometimes. My wife will remind me of things that we’ve done or conversations we’ve had with people that I have no recollection of. At first this really bothered me, but then I realized that it’s because my mind is always thinking about tomorrow, never about yesterday. I don’t dwell on the past. Like everybody, I make mistakes. Probably more than my fair share. I take responsibility for them, try my best to fix them and move on.

8. You hate routine
Some people love a work/life routine. There’s nothing wrong with that, but it scares the crap out of me. I get bored if things are always the same. I love waking up each day wondering what will happen to me. I can’t get enough of life and am afraid that if I get in a routine, I’ll miss out on something big.

9. You aren’t planning for retirement
Now this doesn’t mean that I’m not financially planning for retirement. It means that I’m not planning to ride off into the sunset and take it easy. I’ve often been asked what I’d like to do if I stopped working. My answer is simple; find another job. That job might be volunteering at an animal shelter or building houses for the less privileged, but I absolutely cannot picture myself buying a condo in Florida or Arizona and just taking it easy. I think I’d go insane.

10. You set goals that you know are unattainable, but you don’t care
When I was a kid I wanted to be an astronaut and go to the moon. Then I started playing baseball and I decided I was going to play in the majors. Point is I knew that the possibility of doing those things was slim, but I didn’t care. My goal wasn’t just to make the varsity team in high school; my goal was to play for the Red Sox. My though process today is the same. I won’t be happy until every single person in the United States has tried our product. Even then, I’m sure I won’t be satisfied (see symptom #4). I always tell people that each day I want to swim far enough off shore that I’m not entirely sure I’ll make it back. If a goal is easily unattainable, it’s not a goal. It’s a task.

So there you have it. If you suffer from most or all of these symptoms, you might be a serial entrepreneur. I’m not saying that you have to have all of these to be successful; I’m simply giving you a glimpse into how my mind works. It may not be the best mind, but it’s mine and it’s the only one I’ve got 🙂