How Will You Fail Spectacularly This Year?

by , January 8, 2014

I’m not a big fan of New Year’s resolutions. They feel like a bit of a set up. However, several years ago my partner and I each resolved to fail spectacularly in at least one thing each year. We’ve attempted many things like career changes, learning a new skill or hobby, and bold organizational projects. We’ve even moved to a new state for the adventure of it (hello, Washington!) and adopted our son, Gus. Some of these things we’ve failed at (the success and joy from Gus is definitely not on that list).

I’m not going to lie -- some of these failures didn’t feel very good. Admitting to colleagues that I had failed big time at launching a national learning community felt like I should walk around with a “loser” sign around my neck. That was likely because of the lens in which I viewed my world – a world where failure is considered a sign of weakness. In fact, many people associate failure with things like shame or embarrassment or even guilt. However, there are also people who associate failure with things like learning, opportunity, and improvement. That sounded more fun.

Changing Our Relationship to Failure

“The greatest glory in living lies not in never failing, but in rising every time we fail.” – Nelson Mandela

So my partner and I set out to change our relationship to failure. What we meant by failing spectacularly was not really just about gritting our teeth and taking a risk. Instead, it was about embracing the very notion of failure. We would pursue a thing with great enthusiasm and, if we failed, we would pause and ask why it failed. We would embrace the learning from the experience.

In our new and uncertain nonprofit work reality, failure is fairly inevitable. In fact it’s the rule, not the exception.  It happens when we have to adapt to complex and ever-changing conditions in our organizations or in the sector; when we make the wrong assumptions about people or projects; when there is a strategy or design flaw; or when we are unable to execute or adapt. You get the picture. The list goes on. So, if we can’t avoid failure, how might we embrace it?

Failure is Hot

Failure has become a hot topic over the past few years.  There are books and websites about failure. There are even events held around the country called “Failcons” where people share their failures openly ( calls theirs “FailFest”). Former Hewlett Foundation President Paul Brest oversaw the widespread release of a report on one of their programs that went off course to share what they learned about the failure.  He also created an annual prize at the foundation in which staff nominate and discuss their worst grant of the year. In order to encourage experimentation and risk-taking, Pierre Omidyar empowered teams to spend 5-10% of their budget at the Omidyar Network on things that weren’t clear would have an impact. This embracing of failure can unlock learning and innovation in organizations and communities. It can mobilize others to tackle difficult challenges. It builds transparency and authenticity, resulting in stronger relationships and a sense of trust. It’s really very much about being a leader.


“It is crucial that we remain fundamentally imperfect, incomplete, erring creatures; in other words, that there is always a gap left between what we are and what we can be. Whatever human accomplishments there have been in history, they have been possible precisely because of this empty space. It is within this interval that people, individuals as well as communities, can accomplish anything.” – Costica Bradatan

In February, I will be facilitating a workshop conversation on failure [2016 note bene: This workshop has already taken place; we do not have another session scheduled at this time]. We will share stories of spectacular failures in the nonprofit sector, strategies for embracing failure, and discuss how “failing well” can enhance credibility, trust, learning, and innovation. I invite you to join me– either for the in-person workshop or on Twitter, where I’ve started a conversation. Where have you attempted to fail spectacularly? What did you learn? How will you fail spectacularly this year? I look forward to hearing from you. @mdgislason #FailSpectacularly

Resources on Failure

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