The Upside of Philanthropic Failure

Back in May of 2008 I wrote a piece for the Stanford Social Innovation Review about Jim Canales of the Irvine Foundation and his challenge to philanthropy to fail more frequently. Jim’s point is that failure goes hand in hand with taking risks and if philanthropy never fails it means no risk is being taken and if no risk is being taken then the chance to produce high levels of social impact are off the table. My article followed up on a podcast I had recorded with Jim that generated significant commentary from readers.

So why don’t more foundation’s talk openly about failure? One obvious reason is the worry of reputational damage. In my article I took this concern on:

There is a risk to reputational damage if all of your colleagues refuse to recognize mistakes and foundations pretend to be infallible forces for good. Canales and Paul Brest (from the Hewlett Foundation) both published reports on their mistakes last year. As far as reputational risk, what they got for their trouble was coverage in The New York Times, an op-ed in The Chronicle of Philanthropy, and an enhancement of their already stellar reputations. Their colleagues hung them out to dry, but the lack of other foundations taking similar steps makes Canales, in his own words, “the poster child for failure in philanthropy.” Still, he hasn’t suffered any reputational damage. Instead he is asked to lead sessions at philanthropy conferences.

But now we have a new advocate for the upside of failure: Pittsburgh Foundation president Grant Oliphant. In a new video interview produced by the Communications Network, Grant makes the case for failure.

If you are viewing this post via an email subscription, click here to watch the video. This video is a four minute highlight reel from the full thirty minute video which you can find here.


  1. Dan Pallotta says:


    We must begin distinguishing program from fundraising in all of these discussions. To the extent that there is any tolerance for “philanthropic” failure (not completely sure what you mean by “philanthropic”) it exists on the program side. There is zero tolerance for failure on the fundraising side, and that’s the side on which programs depend. That is the larger tragedy and problem.

  2. Dan, I don’t agree with you on this one. Failure is an inevitable side effect of taking risks (obviously not failing all the time, but the more risk you take the more likely you’ll fail. If you never fail, you’re not taking risks). I would hope that fundraisers are willing to take risks. Sometimes they won’t pay off, but if you always play it safe then you’ll achieve outstanding results.

  3. bob hughes says:


    Thanks for keeping the spotlight on this issue. With the leadership of Jim Canales and Paul Brest, among others, the field is beginning to appreciate that failure can be an important portal into learning and effectiveness. Last year we (Robert Wood Johnson Foundation-RWJF) participated along with colleagues from 7 other foundations in a failure ‘learning session’ organized by Grantmakers for Effective Organizations. It was a very useful and frank exchange among the foundations that participated about where our programs had failed, and how difficult it is to come to terms with failure. That prompted my colleague David Colby to organize four chapters on failure in this years RWJF anthology (Volume XIII, available at that describe a number of failures from RWJF’s program history.
    One aspect of failure that gets too little attention is how tied it is success. Judgments about both require clear goals and strong performance assessment. Perhaps someday it will be routine for foundations to have a much better sense of how they are doing, and how they can learn from failure to get better in the future.

  4. Bravo, Bob! I just tweeted about your “The Role of Failure in Philanthropic Learning” chapter and added it to tonight’s Daily Digest post.

  5. Dan Pallotta says:


    Not sure you got my meaning right. There should be tremendous tolerance for failure in fundraising – it’s the only way we’ll make progress, but right now there is pretty much no tolerance for it, and that has to change. I think we’re in agreement.

  6. Ah, got Dan. I was surprised by your comment. But I see what you mean now. Yes. We’re on the same page.