Can philanthropy make failure hot—again?
There was a time when talking openly about failure was seen as a sign of transparency in philanthropy and development. Why did that movement fade, and why might embracing failure matter more than ever today?
By Paul Constance
For a very brief period in the 2010s, failure was cool. Inside development banks, foundations, and global NGOs, “failure transparency” became a way to signal that you were serious about results, accountability and learning.
The World Bank held several FAILFaires where, to everyone’s astonishment, staffers stepped up to a microphone, swallowed hard, and said a version of, “We tried something. It didn’t work. Here’s why.” Engineers Without Borders Canada published a series of Annual Failure Reports. The William and Flora Hewlett Foundation ran an internal “Worst Grant Contest,” urging staff to nominate “the worst grant from which they learned the most.” Even the New York Times took notice.
I remember the excitement these ideas provoked. Could we finally start admitting, in public, what we constantly discussed in private? Were we ready to confess that most of our efforts to achieve social and economic change do not turn out as intended? Could we actually learn from our mistakes?
Alas, no. Just as quickly as it had flared up, the passion for failure transparency went cold. “Failure fests” became less frequent, or less frank. The language of “failing fast” and “celebrating failure” gave way to anodyne talk of “adaptive learning” and “continuous improvement.” We all went back to pretending that in our work, as in Garrison Keillor’s mythical town of Lake Wobegon, “all the children are above average.”
This was hardly surprising. Organizational cultures will always be allergic to failure. Career trajectories depend on writing proposals in the future perfect (“by year three, this project will have achieved…”) and on notching up wins—not on analyzing losses. Board members and senior leadership naturally worry that an honest post-mortem on a high-profile initiative will be weaponized by critics, who may use it as evidence of systemic incompetence.
There are legitimate reasons to avoid overly negative framings of unsuccess. In an essay in the Stanford Social Innovation Review, June Wang, who was then an organizational learning officer at the William and Flora Hewlett Foundation, explained why her colleagues concluded that:
“Failure is too blunt of a word for the type of work we do”
Her foundation eventually replaced the “Worst Grant Contest” with several methods that acknowledge failure through other means, such as requiring staff to write down what might go wrong at the beginning of a project. (This reminded me of the “pre-mortem,” a method developed by psychologist Gary Klein to prevent disasters through “prospective hindsight.”)
Still, I think it’s time to re-embrace the idea of failure in all its harsh, clarifying power. Back in the 2010s, we were still in what has been called the golden age of NGOs. Money from both governments and philanthropies was pouring in, and there was comparatively little concern about duplication, effectiveness and efficiency.
Today, well, you don’t need a reminder of how things have changed. Everyone knows that confidence in government, media, and large organizations has slid to historic lows. While non-profits generally are still more trusted, their advantage is slipping. This may be because the public senses that non-profits are not being candid about their shortcomings. In my conversations with staffers at progressive advocacy organizations, I frequently hear variations on “what we were doing five years ago just doesn’t work anymore.” But I almost never see such admissions in writing.

There are some encouraging exceptions. My favorite is GiveWell, the nonprofit evaluator that researches and recommends the most cost-effective global health and poverty-alleviation charities. GiveWell features an “Our Mistakes” tab in middle of its home page that leads to an encyclopedic accounting not only of it blunders, but of the steps it has taken to address them.
The Centre for Effective Altruism has a robust “Mistakes We’ve Made” page. The India Development Review maintains an impressive collection of articles it labels the “Failure Files.” And in the world of private-sector start-ups, FuckUp Nights is still going strong. This “global community to break the taboo of failure,” founded in Mexico in 2012, has hosted in events in more than 250 cities.
For failure transparency to come fully out of the closet, however, donors and grant-makers will need to start asking for it. Theresa Scheiber, a vice president at Rockefeller Philanthropy Advisors, recently proposed as much in a brilliant post entitled “Failure as a KPI: Finding Philanthropy’s Courage to Fund and Fail (and Talk About It!)”:
“What if failure were a key performance indicator that we intentionally measured?,” Scheiber wrote. “This isn’t a novel idea. Most fields of innovation embrace failure as part of the equation. Venture capitalists expect anywhere from 80% to 90% of their investments to fail… while the U.S. Bureau of Labor Statistics tells us that over 20% of businesses fail in their first year, and nearly 50% do by year five.”
“Philanthropy, too, fails, but you would scarcely know it because the sector rarely wants to talk about what didn’t work,” Scheiber wrote. She argued that grant-makers are “uniquely positioned to fund uncertainty and experimentation,” but this ability to function as “risk capital” requires a clear a feedback loop: “Failure provides critical signals and insights that help accelerate us toward the interventions and strategies that work, while also enabling us to abandon the approaches that cannot or will not deliver the positive impact our world needs.”
So true! In the coming months I hope to write about organizations that are finding new ways to celebrate “fruitful failures.”
Read more
Is Yuka the future of “name & shame” activism?
Apps like Yuka are transforming consumer activism by turning product transparency into immediate public pressure. Could this new form of “naming and shaming” succeed where traditional advocacy strategies are losing impact?
Learn more
What will 2037 look like for think tanks?
How will think tanks communicate in 2037? We explore tensions around trust, the “human premium,” and digital structure in this joint foresight exercise.
Learn more
DeepSeek is Biased, but I’m Worse
DeepSeek shook the AI world with power like ChatGPT at a fraction of the cost. It not only reflects our limitations, it can help us overcome them. Want to learn how to use it strategically? Join the third edition of our program for Think Tanks and advocacy organizations.
Learn more
Facing the tide: paralysis or reinvention?
For many advocacy groups, this is a time of reckoning. Some are choosing to step back—but others see an opportunity to sharpen their focus, engage beyond their usual circles, and rethink their long-term strategy. We’re helping them navigate this moment with clarity and purpose.
Learn more
What comes after social media?
For quite some time, social media has been portrayed as the antagonists in an endless Netflix like series, much like the endless scroll we navigate with our fingers. They’re a sinister character in the sense Freud described, naming something as familiar as it is terrifying. There’s nothing more familiar than logging into Instagram, X, or […]
Learn more
Are we communicating information that our audiences don’t want to receive?
Communicating policy in a world of too much information
Learn more
From OOO to OHH! Tools to improve the out of office message
Even though we should have learned throughout the holiday season to distrust each “new message” notification, they still get our interest. This time of the year is terrible. So many times, instead of the expected reply to our message, we receive automatic emails with the subject: “out of the office”.
Learn more
Marikondoing at work: the life-changing magic of ordering files
Some practical tips to organize our workflow when we share files with other people
Learn more
Green eggs and ham
While we wait to see if and how our habits will change, the peak of experimentation is providing algorithms with great insights
Learn more
World Cup armbands won’t change the world
Problems in the global communication of such important issues as climate change, humanitarian catastrophes and migratory crises.
Learn more