TPW Talks Failure

Devon Cohn
The Philanthropy Workshop

Last year my mind was full of everything that’s wrong with our education system. Our oldest child was a senior in high school, going through the college application process. Our youngest was a high school freshman attempting to navigate a new environment with a new set of expectations. 

I was reading and watching videos of thought leaders like Ken Robinson, Carol Dweck, and Denise Clark Pope. Sir Ken Robinson, in his book, “Do Schools Kill Creativity,” suggests that our school system educates students to be good workers rather than creative thinkers, in part, by not including failure as part of the learning process.

Carol Dweck promotes the concept of a growth mindset—the idea that our brains and abilities can be developed like muscles and skills; that success requires effort which includes trying, failing, and trying again. However, while schools are beginning to consider the value in expecting, welcoming, and learning from failure, they now throw around the word resilience so much that it’s almost lost any meaning.

At last year’s TPW Network Retreat, I started wondering what it would mean to cultivate a culture that supports failure as part of the learning process within strategic philanthropy. With the retreat’s focus on storytelling, I spoke with a handful of fellow TPW members about philanthropic failure stories, and the consensus was that it would be great to share more. I decided to embrace a growth mindset myself by trying to do something I’d never done before: collecting stories about failure from TPW members. 

Really, what’s the worst that could happen? I could fail at failing. 

Talking about failure has both benefits and barriers. One of the barriers is so big it needs to be addressed first—the word failure. It’s too broad, too final. When you use the word, you think of something large or catastrophic, or finished. 

But failure also includes all the little mistakes and missteps that can set back a small part of a larger endeavor. Basically, the word failure is a failure. So it may be easier to use differently nuanced synonyms like mistake or misstep; and that’s just fine. It’s part of a growth mindset, and an easy step toward changing the conversation.

So what about the benefits of talking about failure? 

It’s easy to see how you can learn lessons from telling your own failure story or listening to someone else’s, and, hopefully, avoid making those missteps in the future.

Talking about your own failures can also help you clarify your thinking about them. Additionally, exposure to failure in a safe setting can change the way you experience failure. Realizing you’ve made an error or facing a failure is unpleasant. Talking about failures in an environment without negative consequences will actually make it less uncomfortable.  And when it doesn’t feel so bad to talk about and think about failure, you have the potential to recognize mistakes earlier in the process, and adjust for them more quickly.  Ultimately, it can change the way you communicate with yourself as well as with your partners. And, the subject can make your philanthropic interactions more collaborative.

This project started as an idea to collect stories, and has evolved into a project focused on changing the conversation about failure. I have interviewed 11 TPW members about their failure stories. I am excited to share their stories and insights with the TPW community through this blog series, “TPW Talks Failure.”

Some members followed up our conversations with video interviews with TPW staff, which you can view on TPW's private Vimeo page (for password information, members may contact The Philanthropy Workshop at  There are stories about lessons learned, about the process of failing, and cautionary tales that shine a light into less explored areas or less well understood areas of the philanthropic world.


Devon Wiel Cohn (TPW 2007-08) is interested in the subject of failure (given she’s experienced so many missteps and, in the process, learned so much), and how it can be applied to strategic philanthropy. She holds a Ph.D. in neuroscience from the University of Oregon, and an undergraduate degree in developmental psychology from Stanford. To share your failure story to help change the culture of failure within our network and the wider philanthropic community, contact Devon at

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