Crippled CEO Blog #106: Fail Small

Crippled CEO Blog #106:

“Fail early, fail often.“

This is a frequently repeated mantra in the world of entrepreneurship and management.

You hear it often as a vote in favor of a risky venture or a new idea.

It sounds forward thinking and innovative.

It also gives you something to lean back on when you do, in fact, fail.

It was all part of the plan! Fail early, fail often. Mission accomplished.

I understand the rationale behind this idea. We can’t be afraid of making mistakes. We need to be willing to try new things.

And we learn from failure.

And while failure does teach us what not to do, you can only learn what TO do from success. 

And when it comes to owning a business, failing early and often is fine if you are young, able-bodied, you have no employees, and don’t have a family depending on you.

If it’s just you that you’re hurting, then take those risks. If the result is you end up crashing on couches for a while, that isn’t the end of the world.

But someone like me can’t do that. Being disabled is expensive. If I fail at this business, I end up living in a nursing home. I will end up in a situation that is impossible for me to recover from.

There is a famous legend about Julius Caesar invading the Celts. He and his armies arrived by sea, and it became immediately apparent that they were outnumbered. His troops were scared, and many wanted to turn back.

“Burn the ships!” he ordered. 

His leaders and troops thought he was crazy. If they burned the ships, in the very real possibility that they were defeated, how would they retreat?

They couldn’t.

And that was the point. With their ships on fire, they knew they HAD to win. Their enemies knew they had to win. And with no other choice but victory available, that is exactly what they did.

My ships are also burned. There is no recovery for me if I fail. I run my businesses knowing that I I have no choice but to succeed.

So, with that in mind, how do we take risks? How do we try new things? As we know, the only person who doesn’t make mistakes is the person not accomplishing anything. But with the boats on fire, what do we do? 

Fail small. Instead of failing early and often, I prefer “fail small“.

Take risks with large upsides and minimal downsides.

Try new things in the smallest possible way first, see if there’s success, iterate on that success, grow it a bit, try it again, and so on.

You can survive failing small. You can lose the battle and still win the war. I have projects that started tiny that are now multi-million dollar revenue streams. 

I have other ones that bombed, but we started small, so it’s fine.

And I have a few in the fire right now that will either be amazing or dissolve into nothing, but I haven’t thrown all of my eggs into those baskets, so if they fail, it’s not going to affect my life.

“Fail early, fail often“ is a good example of advice that’s great for some people, but not everybody. We like to think of these quotable heuristics as being ubiquitously beneficial, but the truth is, like most things… it depends. 

(Do you know who never fails me early, nor often? Your mom, that’s who. She also loves getting a text from me each week with a link to the latest blog. If you send a text to the number 484848 with the word CRIP as the message, you, too, can be so lucky.)