Failblog: learning to mess up from successful people

NOTE: this post originally appeared on the Convergence Academies blog on March 24, 2015.

Here on the internet, we love failure. We love it so much there are entire blogs devoted to curating the best failure GIFs. In fact, if you search “man walking into glass door” on YouTube you’ll find a video of my high school physics teacher facing an inconvenient run-in with the laws of physics. (I guess experience really is the best teacher.)

All this begs the question: what is it that we find so captivating about these failure stories? Is it just our own selfish desire for the aptly-named German concept of schadenfreude (literally, “harm-joy” — or, pleasure in someone else’s pain)?

In his opening keynote speech at the SXSWedu conference in Austin, TX a few weeks ago, founder Charles Best told a different story about failure. is a philanthropy website where public school teachers post projects for their classrooms and funders from across the country make contributions to turn their dreams to reality — a Kickstarter for teachers, before Kickstarter existed. As part of the deal, donors are told they will receive photos and hand-written thank-you letters from the teacher and students whose project they supported. But what happens when a classroom doesn’t follow up as promised? Best explains that, in this scenario, the folks at DonorsChoose send an apology letter to the slighted donors and offer to fund another project on their behalf. As it happens, this act of recompense actually spurs greater generosity on the part of these donors. As he put it, “our biggest revenue driver was screwing up and admitting it."

What was happening here? Did these donors just feel bad for Best and offer up additional funds out of pity?

I don’t think so.

In another conference keynote address, Project H founder Emily Pilloton talked about the importance of failure in her own path toward creating an organization focused on engaging young people in civic action through architecture & construction. "Wear your failures like badges of honor,” she advised. "Talk about them whenever you can."

She even shared her desire to start a conference devoted exclusively to talking about our biggest failures. “People wanna hear those stories,” she encouraged. It’s true. In fact, Best’s own account of his embarrassingly prolonged foot-in-mouth debacle trying to promote DonorsChoose in the New York Times was one of the most delightful and inspiring moments of his opening address.

Watching the audience react with such joy to this story, I was reminded of a professional development workshop we held for Convergence teachers last summer on the subject of digital storytelling. The idea was for the teachers to create and share stories of famous or familiar failures as a way of learning how to use tools like iMovie, Twine, Cowbird, and GarageBand. What we found, however, was that the teachers cared much more about telling these failure stories than they did about learning how to use iMovie to do so. The idea captivated them, and understandably: certainly history, science, and many other disciplines are littered with examples of failures that ultimately led to successful discovery (consider, for instance, the origin of penicillin).

But something about failure seemed particularly relevant — beyond just the content of their discipline — to their own experiences as teachers, and consequently as designers of learning.

A session I attended the following day at SXSWedu, “Learning to Fail with Style and Grace,” offered some possible explanations for this. Hosted by two professors from the University of Texas at Austin and a self-proclaimed “creativity consultant,” the panel examined the role of failure in education, and its complex relationship to learning.

Educators and psychologists alike have long known that learning is a process of struggle, and that those who operate with a growth mindset (“success comes from hard work") tend to meet greater opportunity than those whose mindset is more fixed (“success comes from natural intelligence”). In fact, we see this stark contrast play out culturally in the different messages we give our children about learning.

Yet, in our country at least, we have (at best) a schizophrenic relationship with failure. We know it can be important and even useful, but we are afraid to talk about it for fear of seeming incompetent or unqualified. (Just last week, I sat in a room full of teachers who explained to me that they could not imagine hosting a conversation about their students' work, since their unit did not progress as they had hoped -- all the more reason to share the results, I thought!). Academic success, at least in our current educational landscape, is often an indicator of “mistake minimization.” Parents check their children's math homework for errors before turning it in; college students drop out of classes they can’t seem to master. Those who succeed in school are often those who are best at avoiding — or at least hiding — their mistakes.

And while technology (and its array of fantastic failure GIFs) can be a great tool for celebrating failure, it may also be partly to blame for our lack of understanding around the role of failure in a creative, iterative process.

According to the panelists, technology has sped up our understanding of process almost to a point of invisibility. More so than ever before, we have immediate and easy access to the end-result of a creative process, with little understanding of what it took to get there. Results are at our fingertips, but rarely do they come with explanations  of prior failures. When we ignore process, the product starts to seem impossible. We compare ourselves to where somebody is at the end of their project, rather than where they were earlier — when they were where we are now.

The solution? Make process “super overt.” Understand what it is. Talk about it. Admire it. It’s not magic or genius. Sarah Bush, founder of explained it like this: “We are obsessed with end results. We need to appreciate the emotional arc of a process. Stop experiencing your struggle as a character flaw. Instead, it's normal, part of universal experience and helps you move forward.”

The phrase “universal experience” stuck out to me. The reason we find failure stories so captivating isn’t because we enjoy laughing at others’ misfortune (okay, maybe it’s not exclusively that) — but it’s because understanding someone’s failure helps you see their process. And in doing so, it helps you realize that process itself is universal, if not uniform. In other words, we all fail: just at different times. It’s easy to forget that.

The DonorsChoose backers who received Best’s apology email were motivated to donate again because they were allowed to truly see into the complicated process of running a philanthropy website: warts and all. The admission of error humanized a successful organization, making it seem familiar & worthy of continued support. Surely, they would do better next time, right?

Or, as summed up more succinctly by the Danish poet Piet Hein,

“The road to wisdom? Well, it’s plain

And simple to express:


and err

and err again,

but less

and less

and less."

I left the panel discussion with a newfound enthusiasm for the importance of the failure narrative, and with sparking thoughts about its relationship to less-exciting-sounding things like “documentation,” “student work,” and “formative assessment.” I wondered how, as educators, we are making our learning — and our students’ learning — visible. How are wearing our failures like badges of honor? Pledging to do better next time? Are we only sharing our work when it shows how great a job we did, or are we also willing to share the struggle?

These are questions we ask ourselves every day at Convergence Academies. And they're at the heart of the way we are asking teachers and Digital Media Mentors to spend their time in reflection, iteration, and revision of their work.

Spending time with process is not always fun. It can be tedious. It can be messy. It can be ego-bruising. But it can also be some of the most important and revelatory work we do.