The most difficult part of an entrepreneurial journey is being in relationship with not knowing.

Not knowing can take many forms. It can, for example, present itself as thinking that you know something when, in reality, you don’t.

This is often the case at the beginning of an entrepreneurial journey. You start a company confident that you have an amazing idea and that everybody wants what you’re offering. At some point, you realize you’re not sure how to grow your business, sell your offering, or find new clients.

Then a moment of truth settles in. You actually don’t know what to do.

The ambiguity is crushing because not knowing what to do is much harder to deal with than having too much to do. Not knowing can feel like the onset of death.

And yet, perhaps what needs to die is our fear of not knowing. In many ways, my company today should not exist.

When I started it in 2015, I was reeling from a failed startup experience. I had just moved into my mother-in-law’s house. I was $60,000 in debt. And I was going through bankruptcy.

I wish I could say that I had a clear plan and executed on it. I didn’t. But somehow, without any outside funding, Sutra has now supported over 40,000 people participating in group learning experiences around the world.

What I’ve discovered over the last eight years is that not knowing is a powerful strategy.

Not knowing is not “I don’t know.” Often, “I don’t know” is knowing that you do not know. It is a blocking condition. Not knowing, on the other hand, is an empty space. It is an invitation to discover something new.

This approach invites us to cultivate a certain level of authenticity and humility about what we do and do not know.

In my experience, one of the hardest parts of being an entrepreneur is recognizing your own assumptions and situatedness. It’s easy to think that your ideas are amazing. You invest tons

of time and energy into taking a big leap. And then you discover that people don’t respond the way that you hoped they would.

You feel crushed. What happened? Was it a bad idea? Are you just not good enough?

It’s hard to go through this process without telling yourself that you’re a failure or thinking that something is wrong with you.

But the truth is you really don’t know. And once you can recognize your not knowing without attaching a story to that not knowing, you’re ready to start learning by doing.

Entrepreneurship is not a spectator sport. From the stands, the moral authority of a spectator “knows” how an athlete should have made a play. On the court, the athlete lives the play. They are in a synergistic dance with the reality of the moment.

Not knowing invites us to learn by doing. We prototype what we think we know and find simple ways to test our assumptions with real people in the real world. There is no success or failure. There is only learning and iteration. If you feel like you failed, you probably thought you knew something you actually didn’t.

Prototyping in this way is a “getting to know”. It is about being whole hearted and half sure.

When I wrote the first line of code for Sutra, I had a lot of ideas about how online communities should work. Three months later, I deployed the first version of our platform in a co-working space. Almost nobody used the platform the way that I hoped they would, but I got just enough feedback to make changes and keep going.

In my darkest moments there has always been at least a tiny sliver of light – a next small step. In those moments, all I’ve known is that it’s important for me to take that step even if I have no idea how I will take the step after that.

Sometimes, the next small step is to give myself time to just not know what the next step will be – to hang out in the ambiguity of not knowing. Inevitably, some insight for the next step always emerges.

I’ve come to recognize that rather than being something to avoid, not knowing is actually the most empowered position from which to take action. Because the truth is, there is so much more that I do not know than I do.

We live in a world where we put overwhelming emphasis on knowledge and reason. We need to have a plan and know exactly what to do. But that’s just not the reality of most entrepreneurial journeys. This might be why over 70% of small businesses and over 90% of startups fail.

Think about this for a moment. Is this the statistical measure of an industry that “knows” how things work?

The reality is that not knowing is the foundation of entrepreneurship. It is the very basis of creating something new. The trick is knowing how to not know. Being comfortable in a space of ambiguity as you allow deeper insight to crystallize.

There is a vast difference between busyness and working on the right thing. When confronted by not knowing, our first inclination can be to get busy to avoid the discomfort of that condition. This exacerbates our situation as we approach burnout and struggle to find a way through.

The counterintuitive approach is to notice when you really don’t know what to do next and allow yourself to hang out in that liminal space until you have more clarity about what wants to emerge.

Most people start their own business for some version of freedom. Pretty soon they realize that that freedom comes at the expense of an enormous amount of time and energy. But ultimately, if we stick with it, we discover a different kind of freedom. We discover how to be free from ourselves.

We liberate ourselves from the shackles of our assumptions and we learn to interact with the world as it is. This offers us tremendous intelligence and power to be a catalyst for change.

This is the power of not knowing.