Failure: An Important Tool in Your Philanthropy Toolkit

Devon Cohn
The Philanthropy Workshop

Mistake, misstep, bungle, flop… these are all synonyms of failure, and we’ve all made many.

“Failure” was the theme of The Philanthropy Workshop’s 2016 Network Retreat. Our goal was not to wallow in failure, or even to accept and be complacent about it. On the contrary, the objective was to better understand how each setback presents an opportunity in which to learn and evolve. And learn (and evolve) we did. 

TPW members and staff shared their stories and lessons learned as well as new lessons being discovered about the subject of failure.  One member shared, “If I’d known before what we learned during these sessions, my failure might not have been a failure.”

In sharing our stories, we realized that many of us make the same mistakes again and again. The first day we shared brief stories about failing with our tablemates. Having made our way three-fourths around the table, the next storyteller blurted out, “I’ve made all those mistakes.” 

Here is a list of some of the poor decisions that members felt contributed to their failures.

  • Setting goals and making decisions from the top down
  • Power differences
  • Lack of shared goals and systems
  • Assuming skills will transfer to new endeavor
  • Not mapping or sufficiently understanding the philanthropic space
  • Looking at the wrong risks
  • Not putting in resources early enough
  • Getting dazzled by the big prize, charismatic leaders or great goals
  • Not understanding that goals and cultures can differ greatly between national umbrella organizations & their local branches
  • Chasing loss (thinking of “stopping” as failure)

Based on stories we heard from staff, members, and a number of experts, we also came away with insights in regard to how best to face and avoid mistakes. We learned that talking about problems and mistakes (when they’re surfacing) can help deal with and, possibly, avoid larger problems in the future. 

To make it easier to talk about problems with your partners and colleagues, abandon negative emotions associated with failure such as blame and shame. Reframe the discussion to emphasize it as an opportunity to learn. 

If it helps, change the language from “failure” to growth oriented words like “missteps,” “lessons learned,” and “evolution.”  Ask grantees up front what may go wrong.  Listen actively and with an open mind.  Keep the conversation oriented to desired outcomes; and try not to get caught by the grant cycle and process. 

Remember: the more power and influence you have, the harder it is to obtain honest dissent and dialogue. And stay positive: the goal is to gain insights rather than wallow in failure.

It’s very different to experience failure as part of a group than on your own.

TPW members’ comments have made it clear to me that our discussions about the subject of failure have helped many to see their experiences from a different perspective. These perspectives, in turn, have helped provide greater insight into potential roadblocks, and have inspired members to continue with new energy, with lessons learned often influencing a shift in strategy or tactics. 

During the next few months, I plan to continue our conversation about learning from failure by curating a series of blog posts at In addition to realizing lessons learned, one significant benefit of telling your own failure stories is to gather insights into your goals and strengths, both individually and organizationally. If you have a story about failure that you’d like to share, please drop me a line. I would welcome hearing from you!

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.

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