The Failure Conversation is Broken

by Michael Simmons on Mar 24, 2013

I’ve delivered hundreds of entrepreneurship keynotes in 5+ countries. I have seen hundreds of talks and read hundreds of books on entrepreneurship.

I think the way we talk about failure & challenges is broken.

Of the entrepreneurs that do talk about these, 99% only talk about long-past challenges, which no longer exist. They ignore any current challenges.

At its core, this is a lack of vulnerability that creates a distance between the audience and the speaker that is often perceived as unsurmountable.

Inspiration occurs when audience members are able to truly see themselves in the speaker. If this occurs, then the audience member believes that he or she can also accomplish what the speaker has.

Seeing an unrelatable speaker that has accomplished amazing things is entertaining, but it is not life-changing.

A core lesson that we can teach is that we have had and still have constant challenges, both within ourselves and within our professional life, no matter how good it looks from the outside. More than anything else, it is our courage to constantly take action despite the challenges, which has set us apart.

This lesson cannot simply be shared by going through the bullet points of past failures. It is shown through sharing our humanity via vulnerability in the moment.

I’ve spoken in inner-city schools in New York City and rural areas in Washington State that are 6 hours away from the closest Wal-Mart. I do not pretend that I have had the same events happen to me as anyone else in the world. Frankly, many times the audience has had a much more challenging life than I have. But, I know exactly what it’s like to feel fear, self-doubt, depressed, alone, and feel lack of hope. I’ve experienced all of these, in some fashion, at some point in my life including some of them such as fear and insecurity every single day.

When I write about challenges that I’m experiencing in my personal and professional life, I’m not doing it out of the need for sympathy or help. I am working on changing the dialogue through my own example.

What I surrender through this style of writing is the desire to look like I have everything together all the time.

I don’t, and I don’t think it’s possible to be alive with any amount of self-awareness and for this to be true all the time.

By admitting this to others, we feel courageous. In so doing, we lead by example and liberate ourselves from holding up an illusion.


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I'm the co-founder of Empact, one of the leading entrepreneurship education organizations in the world. I'm obsessed with understanding how we all can lead meaningful lives that have a positive social impact. I love probing into the truth of how we experience life. I believe that challenges are what make us grow the most, and I openly share my experiences. Continue reading…