The Failure of Failing Forward

Mooki FAIL

(This article is based on a talk I gave at Nonprofit Boot Camp in San Francisco.)

Haunted By Failure

A few years ago I led a program at Craigslist Foundation called LikeMinded. It was part of a high profile suite of projects funded by a major foundation. Like 9 out of 10 web initiatives, it didn’t catch on.

It’s almost three years later, and this is the first time I’ve written about it publicly. There’s a taboo around talking about failure, and I’m ready to defy that taboo.

LikeMinded failed for all sorts of reasons, including the most important one: the world decided it wasn’t essential.

What I’ve been learning recently is that what is essential is a real relationship with failure.

We all fail, and failure hurts. I invested years of my life leading this initiative for Craigslist Foundation and traveled more than 100,000 miles learning from community members and partners. When it didn’t take hold, it was disappointing. And when Craigslist Foundation didn’t last long enough for us to learn from round one and try again, it was doubly frustrating.

We don’t have to share our failures publicly, but sharing them has an important role. It helps us move forward. It helps us get the disappointment out in the open so we can process the emotions and grow from the experience.

I grew from my LikeMinded experience. Leading the initiative expanded my skills, and I discovered that they were exactly the type of skills that help me in my current role as a peak performance expert and leadership coach.

The Real Stakes of Failure

failure is cool

This summer I went to a talk about failure. For our name tags, everyone was asked to answer the question: “How do you handle a moment of failure?”

Almost every answer was a variation on: “move on,” “fail more,” or “fail bigger.”

These answers come from a concept called Failing Forward. Originally, this was a great concept. It connected people to the idea that we don’t need to be stopped by failure, and in fact failure might be the pathway to bigger victories.

But somewhere along the line, Failing Forward got corrupted to the point where failure became the badge of honor instead of moving forward. Rather than being a tool, failure has almost become the end. That’s not cool.

This new interpretation of Failing Forward needs to go away.

The point isn’t to fail. The point is to succeed, and failing is more complex than FAIL AGAIN!

At this meetup, Esther Pearl talked about how girls feel no freedom to fail. They feel so hemmed in by expectations that they’d rather not even try. If you’re a girl and you’ve been socialized to believe that you have to be twice as compelling as your male peers, try taking risks, try being resilient, try dispassionately failing forward. Pretty sure I couldn’t.

It’s a good thing we have people like Esther around to work with girls to disassemble this socialization.

It reminds me of how folks feel within nonprofits. They work so hard to get funding that delivering on promises can feel suffocating. While most initiatives in business are not successful, nonprofit leaders feel like every program has to catch on and shine.

Under these conditions, this new cavalier version of failing forward doesn’t help.

Day 222 (Or is this Day 1 now?) - Oops!

Reimagining Failing Forward

We need something different.

Don’t get me wrong. We need to take risks to succeed. And there is virtue simply in taking the risk. Success comes from persistence in spite of failure. All that is still true.

But we need to get back to some fundamentals underneath failure: Learning, Vulnerability and Honesty.


As Failing Forward focused more and more on the failing, we forgot about a critical ingredient: learning. Unless we’re taking in the lessons of a failure, failing becomes flailing. We’re seeing some people lose discernment between experimenting and f-ing up.

Let’s double down on learning. On actual, honest learning.


We’ve stripped the emotion from failing in our attempts to get people to not be afraid of it.

When nonprofit programs fail, it’s not the same as the failure of an app. When social sector programs fail, people are injured, they die, species go extinct, climate change accelerates. The stakes are unimaginably higher.

So when we fail, it hurts, and it’s time to allow ourselves the vulnerability to share both the existence of the failure and its effect on us. Being real about our emotions lets us pass through the failure in a stronger and more creative way.

By the way, the same is true for success. While this article is about being real about failure, being real about our successes is just as important. Too often, we gloss over our successes, feeling only relief or minimizing our accomplishments. It’s time to celebrate our victories, reward ourselves for jobs well done and learn from our successes just as we learn from our failures.


Our culture can make us dishonest about our emotions. Being vulnerable can be perceived as weakness, so we’re dishonest about how failure impacts us. The reality is that vulnerability is a leadership strength. Being honest about a situation allows frank exploration, more collaboration and greater creativity in charting out the next chapter.

And here’s one more thing to be honest about: our experiment itself. If you’re really not bothered by failure, if you’re a “fail more” type who feels nothing from failure, it probably means you didn’t care. It probably means the stakes weren’t high enough to begin with. It probably means what failed was trivial or random or sloppy but certainly not strategic or inspired. Pretty easy to be unbothered by failure when the attempt didn’t matter.

There’s a balance here. Vulnerability can lead us to wilder emotional swings. Radical honesty can be messy. A focus on learning can bog us down in analysis. Finding an equilibrium that serves both the project and the team is key.

310. Embrace

Embracing Failure

Back to that failure meetup. They released a video of the talk, I was really excited to see the name tags they showed as part of the intro.

How do you handle a failure? Quietly
How do you handle a failure? Mourn then learn
How do you handle a failure? Draw and dance

(Full disclosure: one of those was mine.)

These choices are rich and vulnerable and honest. And they are a great sign that maybe we’re ready to move past the obsession with failure.

Let’s abandon the this twisted, emotionless version of failing forward. Let’s be more real. Let’s embrace failure. Embrace it for everything it brings: its pain, its disappointment, its growth, its insights, and the incredible potential for impact that comes from being real.

Let’s fail. And let’s be human about it. And let’s surround ourselves with people who provide the space to be vulnerable and honest and learn.

5 Things I Did Not Expect to Learn from Woody Allen

I’m not a Woody Allen fan. While I have enjoyed a few of his movies, most of the time I find them uninteresting, unfunny and contrived. His latest film, Blue Jasmine, is set here in the Bay Area and had some word-of-mouth, so I gave it a chance. And it was bad.

I’m not surprised that Oscars voters gave Allen a screenwriting nomination this morning. He gets a lot of free passes. I’m sad for the writers whose quality work was passed over in favor of Allen’s reputation.

Look for the Cate Blanchett

Blue Jasmine is a mess except for exceptional acting performances, primarily from Cate Blanchett and Sally Hawkins. Blanchett and Hawkins give Blue Jasmine its strength, and I was happy to see their Oscar nominations. In the midst of what is otherwise a train wreck, their performances redeem the experience.

Wabi Sabi is a Japanese aesthetic. It’s elusive to define, but one way to think of it is beautifully flawed. Cracked pottery. A vocal solo that becomes unforgettable because of the cracks in the singer’s voice. Wabi Sabi. The beauty in the flaw. Finding the Cate Blanchett in a Blue Jasmine.

Seeing Blue Jasmine made me want to write about how wrong the movie is and about how generally wrong Woody Allen’s filmmaking is, but it became more important to find the Wabi Sabi of Woody Allen. What can we learn from this depressing, strange man’s success? What is Woody Allen doing right and wrong, and how can we use those lessons?

Lesson 1: Persistence

Allen makes roughly a movie per year. He’s released 44 films since 1966. Most of them make little impact and disappear, but he has built a reputation that allows him to continue making films in spite of repeated failure.

Every five to ten years, he makes something good that amplifies his legend. The clunkers are forgotten. The hits are remembered.

It’s about persistence. If a success rate of 1 in 10 is enough to become legendary, then we should plug away. We should create often. We should brush off failure and keep grinding forward.

Lesson 2: Be Economical

One of the things Allen does well is operate on a budget. He’s built his reputation such that people will waive their normal fees to work with him. By keeping the costs of each project low, each failure matters less and each success has bigger upside.

The lesson here: take lots of smaller risks and run with the successes.

Lesson 3: Know Your Audience

Woody Allen is not writing movies for me. He’s been fortunate to find a niche audience, one that’s almost big enough to make his movies profitable. He found them, and he keeps speaking to them. Tyler Perry’s done the same thing on a much bigger scale. Both filmmakers release at least one movie a year and speak unapologetically to their niche audience.

It’s a cool thought that all of our freaky endeavors may have an audience among the 7 billion people on our planet. All we have to do is figure out who they are and reach them with something valuable.

Lesson 4: Use Your Team

We all need a support system to reach our peak level of performance, and most of us don’t cultivate the kind of support we need. Behind the scenes, Allen uses his team well for logistics. He has a well-oiled production team that puts all pieces together so he can focus on writing and directing.

Where Allen doesn’t use his team well is quality control. The people around us – our team – are one of our greatest assets. Used actively, they can build and refine good ideas. They can connect us to those who can help us reach our goals. They can keep us on track when we’re off the mark.

In Blue Jasmine, Allen’s quality control was absent. We learn that a large portion of San Franciscans talk with New York accents and that San Francisco is a sunny and warm city with no wind, fog or rain. We learn that there are no gay people in San Francisco – or Latinos or African Americans except when used as menacing set dressing. Something I never knew until seeing Blue Jasmine was that mid-level jobs in the diplomatic corps are lucrative enough to pay for multimillion dollar Marin homes.

Strange and distracting messages. If Allen weren’t operating in a vacuum, his support system would have guided him to small changes that could hold his film together. Which leads us to lesson 5.

Lesson 5: Be Real

Being real binds an experience together. It’s grounding and sometimes uncomfortable. And it can take work. Without realness, we’re out of touch and things get unconvincing and distracting.

I rarely find Woody Allen’s work real. In Blue Jasmine, a story about losing touch with reality, Allen is disconnected from the real in all the wrong ways. I’m not sure whether Allen cuts corners because of the pace of his filmmaking or whether he just doesn’t care about details. There’s a lot of comedy and absurdity about life in San Francisco, but Allen walked away from bountiful comic material and chose to cast New Yorkers as San Franciscans and have them act out a nonsensical plot. The locations look familiar but the people have nothing to do with the city. They don’t ring true. They’re not real.

So how do we stay real? It seems a lot like balancing. We’re always being pulled away from the real, but we have to actively draw ourselves back toward it. Knowing ourselves is key. Otherwise we won’t know when we’ve been pulled away. That support system is important too. Trusted friends can keep us in line.

Just Five? Okay. Here’s An Easter Egg

This post is about what we can learn from Woody Allen, and it’s also about me shifting from venting mode into learning mode. So there’s actually a bonus lesson here, an Easter Egg.

The hidden secret sixth lesson is about Wabi Sabi and Cate Blanchett. It goes something like this. Being real means you get to have an opinion about things – like for instance that Blue Jasmine is a crappy movie. It even means you get to share that opinion. But the sixth lesson is that over-focusing on what’s wrong is a distraction.

Writing a blistering movie review is not what’s important in my life. Dwelling on all the many faults of the film nearly distracted me from the larger takeaways I’ve written about here.

The secret sixth lesson is about learning. It’s about looking past the emotional reaction and seeing what’s useful. Finding the genius in the flaws. Few of us are good at the secret sixth lesson, but it may just be the most important one.

A Footnote

In writing this, I stumbled on a James Altucher piece from a few years ago. Same Woody Allen theme with some different perspectives. Worth reading.