Are You Comfortable? That’s An Entrepreneurial Death Sentence


Growing up I always thought it was good to be comfortable. I like a comfortable bed. A comfortable lead in my baseball games was good. My parents made a comfortable living. Comfort is good. Right?

Yes, comfort is great… in the right places.

Comfort is great in places where you don’t want (or need) to grow. Comfort is designed to make you not want to move. That comfy chair in your living room keeps you in it for hours because it feels so darn good. But you know it’s better for you if you get up and do something, right? That comfy living you make at your job keeps you in that place because it’s easier to not “move” than it is to get up and try something new.

But, I’d argue comfort is also a destructive force.

Comfort can drag entrepreneurs down. Comfort always comes at a cost.

3 years ago I got comfortable.

When I started my companies in 2005 – 2007 I was anything but comfortable. I had bills I could barely pay. No job (because I chose to give myself a year to try this “entrepreneur thing” before I would force myself to work for someone else). My back was against the wall and it forced me to make stuff happen. Those were exciting, fun, and fulfilling times for me. I was outside of my comfort zone big time.

But 3 years ago my back wasn’t against the wall anymore. I had money. More than I knew what to do with. Great customers coming in every single day. Great business partners. A great house. Great family. Awesome trips around the world. Sounds like a great place to be in life right?

The funny thing is from the outside looking in people probably thought I had everything. From the inside I was bored. Not having any fun. I was comfortable.

When you’re comfortable you stop growing as a person and entrepreneur. You stop trying to innovate. You stop “hustling” and making stuff happen. You stop thinking of new ideas. You stop having real purpose in life that fires you up every day. I found that comfort is a death sentence to an entrepreneur.

So what did I do?

I forced myself to get out of my comfort zone in almost every aspect of life. That business that was bringing in the big bucks but was boring me… I sold it and started a new business that was new and challenging to me. That nice home office I had… we turned it into a baby nursery and I went out and secured an 8,000 sq ft space in town… the Roseburg entrepreneur workspace / office we now call theLoft, and recruited other “comfortable” entrepreneurs to come work there so we could collectively get out of that comfort zone.

I got out there and met people. Lots of people. In fact, I’m typing this sitting in a coffee shop (in a comfy chair by the way)… where I work from time to time. The main reason I work at coffee shops from time to time is I have a goal to have a meaningful conversation with one new person every day. Today’s convo with Chris (great to meet ya Chris!) was AWESOME. If I still lived in that comfort zone, I never would have met Chris today.

So, whether you’re an entrepreneur or not… we’re all in this together. Life is more interesting, fun, fulfilling, and AWESOME when we live outside of our comfort zones. Next time you start to feel comfortable, ask yourself if comfortable is really what you want. Put yourself in positions everyday in life to force yourself to do something new. If you feel that weird feeling in the pit of your stomach that you get whenever you’re nervous, just know that’s a good thing.

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