Let’s Stop Blaming Women for their Fear of Failure (And help them overcome it instead)

By Amy Gannon

I had an entrepreneur walk into a coaching session with me recently, and the first thing she told me was that she just spent $1,000 on fabric for curtains for her house.

I wasn’t sure why she was telling me this. But I kept listening.

“It means something is up with me,” she told me. “I’m avoiding doing the things I should be doing for my business.”

For this entrepreneur, the curtains were a signal that she was feeling out of control. Many of us “nest” as a coping mechanism to manage stress. When my co-founder starts cleaning up her desk, it signals one level of stress. When she starts in on the whole office, I know she has leveled up.  

Nesting is good — until it’s not. Using nesting activities with intention and moderation is productive. Using nesting to avoid something is not. When we bump up against the walls of our comfort zone, we like to retreat into things that restore our sense of competence.

Fear of failure traps us into doing things that feel productive, but don’t move our business forward. Sometimes this looks like nesting. Other times, it looks like taking one more pass at the business plan.

There’s this false notion that if you plan out your business with enough detail, then everything will go smoothly and according to that well-researched and organized plan.

It simply doesn’t work that way, but we convince ourselves that we need just one more piece of information, or we need to meet one more key person, or we need to save one more dollar.

A woman’s fear of failure is not a character flaw, nor an indication that women are not fit to run businesses. Women have very good reasons to be afraid, not because they are more likely to fail, but because they are more likely to experience negative repercussions when they make mistakes. It isn’t in their imaginations. It is reality.

Women are navigating an environment in which:

• • People expect them to fail;

• • They get grilled more about how they are going to avoid failure than how they are going to achieve success; AND

• They get called out for being too confident.

When women make mistakes, it validates the internal biases people hold that women just aren’t as capable as men. In contrast, often when men fail it is viewed as a necessary step toward success.

In investment pitches, male entrepreneurs get asked questions about potential gain, while female entrepreneurs are asked questions about potential losses. Our society anticipates that men will succeed and women will fail.

These biases have tangible consequences. Entrepreneurs who are asked more questions about preventing failure receive 7 times less money than those who are asked more questions about generating success.

Doing — actually testing out our plan with real customers and collaborators — means declaring our ideas and owning our vision in public ways. This, too, poses a unique challenge for women to navigate.

Our society still does not like women who have the audacity to think they are experts, to declare big dreams, and to set personal and professional boundaries. Women who do this get put in their place in both overt and subtle ways. The message is clear, “Who the hell do you think you are?”  Women are damned if we do and damned if we don’t. When women self-promote, they are seen as arrogant and out-of-line. When women don’t self-promote, they are blamed for not being able to sell themselves like men do.

Knowing all of this, it is easy to understand and appreciate why some women hesitate in the entrepreneurial process (or retreat into curtain buying and office cleaning!). Given the world we have to navigate, we can easily become trapped in the planning process and, sometimes, become a deer in headlights.

So, what do we do?

1. Break it down into doable experiments

When I work with women entrepreneurs, we focus on breaking the work down into smaller, focused and somewhat tolerable risks. Entrepreneurs learn by doing. Instead of a huge, overwhelming plan, we need to develop a theory that we can go out into the real world and begin testing. I start with these questions:

1. What do we know?
2. How do we know it?
3. What assumptions do we hold and how can we test them?
4. What additional information do we need and how will we get it?

Taking what we know, we’ll come up with a theory about our customers, their challenges, and our products and services. We design experiments that test our theories and assumptions in the real world. We start with small experiments (surveys, conversations, etc.) and use that information to design bigger experiments (pilots, soft launch, etc.). We engage in a cycle of gathering info, designing and deciding, and then gathering more info.  

We make an ongoing commitment to data collection. Success in the early stages of entrepreneurship is not measured by selling, or by having ‘yes’ people tell you what you want to hear. Success is measured by the amount of usable data that you gather, even if the results don’t match your expectations.

2. Craft an authentic CEO identity through practice

When we are first starting out as entrepreneurs, we get into the work and are hit by all of these responsibilities that we don’t know how to handle, and we think, “Maybe this means I’m not fit to be an entrepreneur because I’m not comfortable.”

As entrepreneurs, most of our responsibilities will be outside our expertise.  We’re trying to make marketing, legal, and financial decisions. We’re trying to develop a product, understand customers, and find amazing talent to hire. Of course it’s going to be chaotic!

The notion that any one person is supposed to know how to do all of those things well is ludicrous. The key is identifying which responsibilities we are really good at, which ones we potentially could be good at, and which ones we are terrible at. Then, we find reinforcements to help us grow our strengths, build new skills, and outsource work.

Authenticity is an important core value for many women entrepreneurs. But, sometimes we mistake ‘new’ and ‘outside our comfort zone’ for ‘inauthentic.’  When a woman says, “That’s just not me.” I ask, “How do you know that’s not you? Maybe you’re just inexperienced? Or just scared?”

Many of the women I coach don’t want to call themselves CEOs. They’ll introduce themselves as a chef, or a writer, or an artist, or a software developer and then they’ll say they created a thing. I insist that they introduce themselves as Founder & CEO.

Who the hell is the CEO if it’s not you?

Sometimes, we hesitate to call ourselves CEOs because of gendered stereotypes about what CEOs are like and how they “should” behave. But this is our chance to redefine that!

We can be authentic, even when we are stepping outside our comfort zone. We can craft a CEO identity that works for us and for our venture. In fact, we need more women challenging the status quo. And, we need more men learning from them.

3. Do NOT internalize the “Know Your Place” nonsense — Be Audacious

A man once shared with me a situation that brought his biases to the surface in ways he hadn’t been aware of previously.

He was invited to give feedback on an entrepreneurial team’s pitch along with several other experienced entrepreneurs and coaches, most of who were men, but there were a couple of women in the room. After the pitch, one of the women said she wanted to speak first to get the conversation started. He shared that his first thought was, “What a bitch!” Then, after he listened to what she was saying and how she was saying it, he caught himself. He was appalled by his own initial reaction, which was not justified.

This is how we are all culturally trained. In this case, the man caught himself, and I appreciate the self-awareness he demonstrated. Too often, men and women have this same reaction and don’t recognize it for what it is. Instead, they begin engaging the woman as if she has done something offensive and try to put her in her place.

This means women have to expend energy finding ways to navigate this again and again and again. It is exhausting and our patience begins to run thin. This is a layer of effort that men, until recently, simply have not had to deal with.

When I watched Serena Williams at the US Open trying to advocate for herself, while also not being perceived as a raging bitch, I cried. I had a visceral reaction to watching her bounce between being assertive (hand out to grab attention) and being accommodating (hand to chest to be apologetic). I watched her in real time try to thread the needle and understood what that was like. Her tears of frustration and rage were my tears of frustration and rage.

Doyenne chose the tagline, “Be Audacious” because we live in a world where being a strong woman is an act of audacity. We know our place is to lead and build and innovate alongside men.

And we will accept nothing less.