What if it doesn't work? Rewriting the fear of failure in entrepreneurship

A few weeks ago, a friend of mine burst through the door brimming with the joy of a new idea. I won’t spill the beans here, but it’s a good one—it solves a problem and is perfectly aligned with what he enjoys offering the world. It’ll stretch him a bit—he’s gonna have to learn a new skill in order to make it happen—but ultimately, I believe that creating this thing is going to be both fun and good for him as a person and an entrepreneur.

There’s only one problem:

He doesn’t know whether or not it’s going to work out.

How can entrepreneurs overcome the fear of failure and embrace the unknown?

People come to me with ideas. A lot. I have a tendency to get really excited about whatever the person who’s talking to me is really excited about, and I’m good at the Internet (launch strategy and marketing), which gives me something to offer founders.

The elephant in the room is, of course, always the potential for failure. None of us ever have any foolproof way of knowing whether or not the idea we have is going to “work.” 

If we’re lucky, we might have data and evidence—examples of it working for us in the past, or something similar currently working for other people—but the best any of us really ever have is an educated guess.

The fear of failure is not limited to entrepreneurship but, like many things, it is exacerbated by it.

I notice that it’s especially challenging for creative business people, who tend to be weaving a business idea into life not from some strategic identification of a gap in the market but from an intuitive nudge or pull in a particular direction.

When your business feels directly tied to your identity as an artist or a maker, it can be painful to even acknowledge that there’s a potential that it might not work out how you think it will.

A few months ago I asked Notion’s AI tool to generate a list of “top business tips.” I’m still working my way up the list of 10 recommendations it offered me, and today my prompt was #4: “Take risks and don’t be afraid to fail.”

Great advice, don’t you think?

The question is, of course, how the hell do I do that?

Learning From Failure: The Science Experiment of Entrepreneurship

What I can offer you is the metaphor that always works for me, which is the idea that this is all one big science experiment.

I’ve got my hypothesis, sure—I’ve done the research, I’ve studied, I know the strategy and what variables I can test to try and get my desired result.

But in the end, whether or not it turns out as I expected isn’t what determines whether or not I “pass or fail,” because either way I end up with more data and information that I had before.

Anyway, back to my friend. By the time he left, I could tell his idea balloon had deflated slightly. And so I sent him this text:

Figured you might need to hear it as well.

What's underneath your fear of failure as an entrepreneur?

Fear of failure is a common obstacle faced by entrepreneurs, artists and creative business people alike.

Fortunately for us, failure in business provides invaluable lessons and insights that make our next attempt even smarter. 

Embracing failure as a natural part of the entrepreneurial process allows us to iterate, refine our strategies, and get what we want with more ease.

Now, doesn't that seem worth it in the end?