If you aren’t experiencing failure, then you are making a far worse mistake: You are being driven by the desire to avoid it.


The better, more subtle interpretation is that failure is a manifestation of learning and exploration. If you aren’t experiencing failure, then you are making a far worse mistake: You are being driven by the desire to avoid it. And, for leaders especially, this strategy—trying to avoid failure by out-thinking it—dooms you to fail.

As Andrew puts it, “Moving things forward allows the team you are leading to feel like, ‘Oh, I’m on a boat that is actually going towards land.’ As opposed to having a leader who says, ‘I’m still not sure. I’m going to look at the map a little bit more, and we’re just going to float here, and all of you stop rowing until I figure this out.’ And then weeks go by, and morale plummets, and failure becomes self-fulfilling. People begin to treat the captain with doubt and trepidation. Even if their doubts aren’t fully justified, you’ve become what they see you as because of your inability to move.”

~an excerpt from the exceptional book, Creativity Inc.

Even though this book isn’t really about startups, it nails so many great concepts that startups need to embrace. I pulled two concepts out of this passage: Startups must have a destination, and failure does not equal sinking.

Startups must have a destination

The boat example that Andrew lays out above is a great one. The captain (CEO) of this hypothetical boat must have the destination in mind before pushing off the dock. The destination can be a high-level concept, but without it, the boat will drift off with no sense of purpose. A related post: Startups must envision the end goal if they want any chance of getting there.

I see the first two years of Dragon Army as a boat that has a destination, but one that has been constantly course-correcting on how to get there. Some have accused me of not having a clear vision for the company because they see us pivoting quite often. In reality, my confidence in our team and our vision allows me to start the voyage not really knowing how we’ll get there. And because of that, we have to constantly tweak the path until we nail it.

Failure does not have to equal sinking

The boat analogy extends to help explain the concept of failure for a startup. To me, failure with a startup usually doesn’t mean shutting it down (or to continue to extend the analogy, sinking), but instead means taking chances, placing bets, and when those bets don’t pay off you adjust, patch the holes, and keep moving toward your destination.

If I’m betting on a startup CEO, I want her to say she can embrace failure throughout the journey, as long as that leads to learning and improving, but that she is sure as heck going to do everything she can to not let the company fail. You fail throughout the journey so that your company lives. Related post: The gigantic difference between failing, and failure.