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The devil you know may be holding you back

Last week I had a drink with an experienced exec that has worked in big companies all of his life and never worked for a startup. That’s fine, not everyone is made for a startup life.

But at one point, in the conversation he told me that he’s been tempted by startups a number of times but reminded himself of that old saying “the devil you know is better than the devil you don’t”.

I paused when I heard that comment. I believe that saying is counter productive.

To me, it says that the person is unwilling or unable to take chance or make a decision where the outcome is unknown. I told him that the outcome is rarely ever known.

I thought about that conversation last night while watching the Super Bowl. The Saints started the second half with an onside kick. I was blown away. What a gutsy call. I’m not sure how many teams recover an onside kick but that didn’t stop the Saints from giving it a try. They just went for it. And it paid off big time.

Gutsy calls knock on your door when you least expect it. Every startup I’ve been part of had uncertainly baked in. The first gutsy call I made was at 22. I quit my first job, took my life savings of <$3k, packed my life possessions in the back of my hatch back and drove from Boston to San Francisco in 4 days. I had no idea what life was going to bring.

Most people I’ve met in SF actually came from somewhere else. They left it all behind and didn’t think about the devil they know vs the devil they don’t. They just went for it. Maybe that is one reason why SF is a special place to me. It’s a gathering of folks that are taking personal risks.

Now, don’t get me wrong, people take risks everywhere but my direct & personal experience with SF transplants is an interesting datapoint (for me at least)

Most people that I’ve met who have remarkable life stories always looked back on their gutsy calls and were happy that they took that chance. Even if it didn’t work out in that specific instance they were better for leaving behind that safe cozy place.