To solve impossible problems, we need to fail more—a LOT more

By Caitlin Hannon
|
04 / 24 / 22

I started 2022 with an impossible goal—a goal that felt so unlikely, so totally implausible, that it was laughable in its audacity. I wrote it on my whiteboard and stared at it. “I do not know how to do this,” I thought. 

My natural tendency as a (recovering?) perfectionist when faced with something I don’t know how to do is to completely avoid it. Or to start so small that I spend months basking in indecision and self-doubt — which is how I’ve handled nearly every key career juncture of my life. Whether it was running for office at 27 or walking away from a secure job to launch a non-profit, eventually I committed to action, but tortured myself for weeks before making a decision, second-guessing every step along the way.

But as I took time during my maternity leave to reflect on how I wanted to show up differently in 2022, I decided my word of the year would be “decisive,” and I was going to decide to fail a whole lot more. I started my year with the goal of failing 25 times per quarter on my way to my impossible goal. THIS WAS UNCOMFORTABLE. Just looking at the list made my hands clammy and my stomach nauseous. I wanted to get meetings with funders in areas where I hadn’t worked before, like maternal health and the environment. I wanted to write proposals for people I’d never met. I wanted to work with funders like MacKenzie Scott and find the next generation of forward-thinking philanthropists who want to reshape the field. 

And I set the goal of failing 25 times because I knew the biggest barrier to achieving my wildest impossible goals was not skills or experience or circumstances — it was the fear of failure I’ve carried with me for my entire life. It was that fear that led me to act small; to apologize my way through proposals to funders when I was a grantee; to keep myself safe by taking an incremental approach to decision-making. It was also what kept me from aggressively striving for the impossible — something that funders and their grantees alike need to do if they want to change the world.

The field of philanthropy needs a radical cultural shift around talking about failure. Instead of sitting down at conferences to talk about our successes, we should be convening to brag about our failures. We will learn faster and try more things when we make failure a safe and expected consequence of taking big action.

Here are three suggestions for how forward-thinking funders could begin to shift the culture around failure within their giving:

Change the focus of your check-ins and reporting

Typically, check-in meetings between grantees and funders focus on everything that’s going well in an organization or program. Grantees often feel compelled to craft a narrative that overplays their successes and downplays any failures, leading to missed opportunities for all. The result? The dog-and-pony show, where failures are swept under the rug and token successes take the spotlight. 

But “failures” in philanthropy can still contribute to knowledge in the field—if they’re acknowledged and the lessons learned are shared with the community. If a grantee’s failings reveal a critical flaw in their theory of change, you want to learn that as fast as possible so you can adjust. If the organization racks up a dozen failures trying to organize an impossible number of community members toward action, their attempts and strategies can teach others about what to try and where the juice might not be worth the squeeze.

To change the focus of your check-in meetings and reporting so that you can begin to get real with your grantees, you have to develop a trust-based relationship. Your grantees need to know that you value their proximity to the community, that you recognize their track record of devotion to the issue, and that you’ll continue to back them taking action and innovating, even if the work they’re doing at this moment doesn’t come to fruition. 

Encourage grantees to accept failure as a consequence of massive action

When grantees sense that their funding will be in jeopardy if they don’t achieve a particular metric of success, they’re incentivized to set that success metric within an achievable, safe range — which typically means they set their sights on incremental improvements, instead of radical transformation of entire communities, or even complete elimination of problems. 

But imagine what would happen if you were to challenge your grantees to make a list of failures they’d like to achieve within the next 12 months on their way to an impossible goal. Of course, to cross a “failure” off your list, you have to take some kind of action — this is not about making a massive to-do list and then drowning under the weight of it. It’s about ending the stigma associated with trying things that may not work. 

A grantee who is focused on making sure they can hit a metric isn’t going to shoot for the moon. Encourage them to go big, recognizing that in failing to get there, they may still get much further than if they’d shot for the “safe” metric.

Change the timeline, not the goal 

The typical grant agreement asks grantees to set goals for what they’ll accomplish in 12 or 18 months. While in theory, this promotes a sense of urgency around meeting those goals, in reality, it pressures grantees to set goals they know are achievable, which can severely limit their vision and their results. 

To encourage grantees to set more ambitious or even impossible goals — things like getting 100% of students to read at grade level by eighth grade, or ending homelessness in a community — they need to know they won’t be punished for missing those goals in the immediate future. Instead of asking what your grantees will accomplish in 12 months, consider asking how they’ll transform their community in 10 years. 

This isn’t about taking away urgency — there’s still urgency around taking action and trying different approaches to solving the problem at hand. It’s just about removing the requirement that we solve the world’s biggest problems on a typical grant cycle. This, coupled with encouraging grantees to set goals around failing regularly, will lead to bigger, bolder action that will help grantees AND funders learn faster and accelerate change. 

To drive a culture shift among your grantees, you first have to model your own comfort with failure

At Building Impact, we believe that being a forward-thinking philanthropist requires changing yourself before (or in conjunction with) supporting change in the world. Being a catalyst for truly sustainable change requires an ongoing commitment to personal development, including exploring your own thoughts and feelings about failure and the shame that we, as humans, often associate with it. How can you, as a funder, boldly walk into peer convenings and talk about all the ways you and your grantees have failed this year? By modeling your own attitude shift around failure across your entire approach to philanthropy, your grantees will be more likely to follow your lead.

Deciding that I wanted to fail as many times as I could in 2022 completely transformed the way I spend my time. I’ve gone from sitting and thinking about what I should be doing, to trying a bunch of things that may or may not work. And when something doesn’t work, I no longer believe it means anything about my innate talent or worthiness as a human being. Instead, I celebrate my failures as evidence that I’m taking big action toward the impossible. I believe this could be transformative for grantees. 

Imagine what we could achieve if philanthropists not only allowed but encouraged grantees to approach their work with the joy, creativity, and failure required to achieve the impossible.

Share

More Insights & Resources

In 2021, at the height of a global pandemic, 98 new billionaires joined the Forbes list in America alone. Collectively,...
By Alex Johnston
|
12 / 14 / 23
This holiday season my wife and I are celebrating our 15th wedding anniversary. Ever the philosopher, my 13-year-old son asked...
By Mike Wang
|
12 / 08 / 23
Over the last eleven years, we’ve had the privilege at Building Impact to partner with incredible donors and other changemakers...
By Building Impact
|
10 / 20 / 23
A few weeks ago I shared some data about the demographics and giving habits of the ultra wealthy on my...
By Alex Johnston
|
12 / 15 / 22
One of the biggest barriers to giving, and giving effectively, is the American taboo around talking about money and wealth....
By Alex Johnston
|
08 / 24 / 22
Recently, a well-respected philanthropist came to me on a mission to find more meaning in her giving. Many like her...
By Mike Wang
|
07 / 20 / 22
In my neighborhood in Philadelphia, the effort to improve a physically dangerous, unattractive thoroughfare has come to illustrate one of...
By Mike Wang
|
03 / 02 / 22
This month, I returned from maternity leave after having my third child in October. With my first two children, I...
By Caitlin Hannon
|
01 / 25 / 22
As 2021 draws to a close, one of the year’s bright spots for me was the AppleTV show, Ted Lasso. At...
By Mike Wang
|
12 / 07 / 21
Here’s what that means and why it can be incredibly fulfilling for you as a donor. One big reason funders...
By Alex Johnston
|
11 / 24 / 21
Before any reports came out detailing the extent of the academic impact of the pandemic on students, education leaders were...
By Caitlin Hannon
|
09 / 16 / 21
As school systems around the country manage the challenge of returning to in-person instruction amidst the surging Delta variant and...
By Mike Wang
|
09 / 01 / 21
Over the past few years, a variety of leaders in philanthropy have been calling for funders to embrace more risk in their...
By Alex Johnston
|
08 / 03 / 21
So you’ve decided you want your philanthropy to be more transformative. Or innovative. Or to better live up to your aspirations...
By Mike Wang
|
06 / 21 / 21
One of the biggest barriers to high impact philanthropy is the fact that the people with the most  financial resources are rarely...
By Alex Johnston
|
05 / 20 / 21
To white people, from another white person –  I’m white, and I grew up in a predominantly white and wealthy...
By Molly Barnes
|
04 / 30 / 21
In America, we tend to believe that enough money can fix any problem. Who hasn’t sat around thinking, “If I...
By Caitlin Hannon
|
04 / 09 / 21
“We just can’t work with them anymore. Their political views are repugnant, even if they were with us before…”  “…But...
By Mike Wang
|
03 / 05 / 21
The last few years have seen an increasingly public critique of philanthropy, with books like Just Giving by Rob Reich, Decolonizing Wealth by Edgar...
By Alex Johnston
|
01 / 25 / 21
The endless, destabilizing uncertainty of 2020 that has put all of our lives in turmoil has also brought a gift...
By Building Impact
|
12 / 23 / 20
Search