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“Failure [is] the gap between where we are and where we want to go.” A Conversation with Sarah Lewis

Sarah Lewis is the author of The Rise: Creativity, the Gift of Failure, and the Search for Mastery. Lewis is a faculty member of the Yale University School of Art, has served on President Barack Obama’s Arts Policy Committee, and been selected for Oprah’s Power List. The Communications Network spoke to her about the difference between success and mastery, how a near-win can be a good thing in the long run, and why grit matters more than talent and IQ. A lightly edited transcript follows. 

The Communications Network: Your book is an interesting mixture of topics: creativity, mastery, and failure. What inspired you?

Sarah Lewis: The book is about the unusual, improbable foundations that undergird our most iconic achievements, whether that’s an achievement in entrepreneurial realms or invention or creativity.

I approached this book as a curator. I used to work at the Museum of Modern Art in New York and Tate Modern. I’m also a cultural historian.

Over time, I would start to see these kind of back-turn paintings in artist studios, things that they didn’t want to show me, but I knew were integral for the work that they did want to show me, that would then go on to have a platform at MoMA, etcetera. I started to wonder if that idea of this back-turn painting being critical for masterful work wasn’t applicable beyond a creative realm of endeavor, whether I thought that it was true for entrepreneurial feats as well.

Over time, I would just look at a set of different examples. The book looks at an atlas of about 150, but, when I began to write, I knew, at the time, that Martin Luther King got Cs in oratory class, for example, went on to become our most prestigious orator in the century.

I knew that Fred Astaire’s screen test said in 1930s, “Can’t sing. Can’t act. Balding. Can dance a little,” and he went on to revolutionize his genre.

These stories populate the book, but, really, they were just known to me because I’ve been just organically interested in this notion that some of our most inventive achievements have come from places that we don’t expect.

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The Communications Network: As you mentioned, you talked to more than 150 people and did a tremendous amount of research as well. Of the stories that you uncovered, do you have a favorite that stands out?

Sarah Lewis: They feel like children, the stories. I’ve become so enchanted with so many of the people that I interviewed and met with. Let me give you a historical example to be safe.

I was intrigued by the story of Samuel Morse a great deal. I read about him in the context of the importance of grit, grit being the ability to withstand not just momentary distractions, but to persist in your goal over years and maybe decades, despite failure of feedback.

Angela Duckworth’s now MacArthur-winning study has shown that grit is the most important predictive for achievement in an educational context beyond talent or IQ alone.

Samuel Morse is a great example of this. As I learned, he spent 26 years, in his mind, on the failed pursuit of being a painter. Exhibiting his paintings put him into debt. He couldn’t support his family, who was living in New Haven, while he was in New York traveling with his work, studying in Europe.

When he reached this nadir in the whole process, he took one of the stretcher bars from his canvas, the wooden frame behind the canvas, and he used that as the raw material to create the telegraph. It then took him another 2 decades to create and receive the patent that would revolutionize the communications industry, making him our first kind of tech entrepreneur, really.

I love how vivid that example is, that the material from a kind of failed foundation can become the foundations for someone’s rise.

The Communications Network: In his case, and perhaps in some of the other stories you saw, what was his reaction to that success? Did he, even at the end of his life, still see himself as a failed painter, or did he take pride in his success as an entrepreneur?

Sarah Lewis: Samuel Morse, at the end of his life, did see himself still as a painter, or at least desired to still paint. He said to his friend, James Fenimore Cooper, the famous author, “I sometimes indulge a big dream that I may paint again.”

When he would travel to Europe, he wouldn’t let himself go to museums, where he’d spent so much of his time. He, in many ways, did still see himself as a failure.

It gets at something really important that I discuss in the book, which is that the idea of failure isn’t about a label that the world puts on us, but is instead about this internal landscape.

I see failure, really, as the gap between where we are and where we want to go. Only an individual knows if they’re living in that gap or not, really.

Despite his success, he was so famous, Samuel Morse, at the end of his life, that you could just write the Lightning Man, the name he became kind of known by, and plot an address as New York, New York, and the letter would get to him. He was that famous. He just wanted some peace and obscurity, but he really internally felt that he had failed in not meeting his main goal.

The Communications Network: In your book, you talk about the difference between success and mastery. Why, in the long run, do you think mastery matters more than success?

Sarah Lewis: Mastery and success are distinct. Success, I believe, is a label that the world confers on you for hitting a benchmark that allow people to see you as having achieved something, maybe enviable, in their eyes.

Mastery, if you look at the lives of different individuals who we might consider masters, shows that it is about not just success, but seeing your life as a journey, seeing any kind of benchmark of achievement as perhaps just a near-win so that you have enough fuel to keep on going.

Think about Paul Cézanne, for example. We see him certainly as a success, certainly a master. Why is that? In large part is because he never was fully satisfied, and that kept him going until the end. He didn’t sign 90% of his paintings because he didn’t feel that they met his goal of realizing nature in paint. You can see the same dynamic of this sort of perpetual sense of a near-win with masters, if you look at their various lives.

The reason why mastery, I think, is more important than success is because success doesn’t really motivate us. It’s a nice thing, but it doesn’t propel us onward. Mastery is more important because it allows us to see our life as a journey as opposed to just one moment in time.

The Communications Network: How do you think people come to that realization that life is, in fact, a journey, and not a series of winner-take-all competitions?

Because I think many of our listeners have worked in organizations where people are punished for making a mistake. Sometimes that punishment can take the form of dismissal from a job or permanent setbacks in their career. Obviously, the culture of organizations are affected by that – people become risk-averse.

Then there are other organizations where people do learn that lesson and they see life as a journey, but how do you think, in your research and in your conversations, did you find that people came to that realization or learn that lesson?

Sarah Lewis: Many creative individuals learn that lesson and understand that their lives are a journey because the process tells them that that is the case, because when you create, there are sort of two realities you live with. There is this sort of external world where people respond to what you put out and might deem it with some acclaim.

Oftentimes, the internal world, the sort of second reality of any creation, reminds you – because you might not be satisfied with it – that you still have more to do, that there’s still more that you need to create.

An example of this is when an interviewer asks Duke Ellington, a jazz musician, what his favorite work in his repertoire was, he said, “Always the next one. Always the one I have yet to compose.”

People, oftentimes, who were creative, will answer in that way because they understand that in order to stay creative, they need to be able to see their life as a lineage. Oftentimes, because we look to timeless masters when we create – Tolstoy, you name it – we are reminded that we’re doing work that will go beyond our lifetime perhaps, and is an extension of the work that has come from lifetimes before.

When you’re not in a creative field, I think one of the main ways that people remember that our life is a journey is by focusing on someone’s life story, looking at all the different permutations that have gone on to allow them to become who they are known for being.

Samuel Morse, as we just discussed, is a great example of this. People might see him, if they don’t know his full story, as a telegraph inventor, but when you understand his full arc, you see all that he had to go through, in terms of failed pursuits in painting, to arrive at that position.

The Communications Network: One of the stops on that journey, and you described it earlier, is the near-win. Tell us more about the near-win, what it is, and what are the benefits of the near-win?

Sarah Lewis: The near-win is the phenomenon where coming close to your goal, but not quite arriving at it, gives us a sense of frustration enough to propel us to reaching a goal that we never imagine we could. We see this really vividly in athletic competition, especially Olympic competition. There has been a great study done at Cornell about the near-win phenomenon as it relates to what silver medalists go through as distinct from bronze medalists.

What the study has found is that the frustration that silver medalists feel on not receiving the gold, on average, is much greater than, say, that of bronze medalists, who tend to be happy that they didn’t receive fourth place and no medal at all.

Why is that so? It has to do with what Daniel Kahneman and Amos Tversky called Counterfactual Thinking, the ideas that the mind tends to rest on the easier to imagine scenario, the more frustrating scenario in this case, of what someone had just missed achieving.

One way to consider this is to imagine yourself going to an airport. You’re about to try to catch a flight and you missed your flight by, say, 5 minutes. If that were the case, you probably would never miss a flight again. If you miss it by 30 minutes, it’s harder to imagine what you could have done differently to arrive at the airport on time.

In the same way, bronze medalists don’t really dwell on what they could have done to receive the gold as much as silver medalists do, who are much closer to it.

We see the near-win playing out not just in athletic competition, though, but in creative human endeavors of all kinds. It creates this “ever-onward” feeling for artists.

Michelangelo is a classic example, in some cases, of the near-win. He wrote, at one point, in a letter, “Lord, grant that I might always desire more than I can accomplish,” as if he understood that the thrust of the near-win would allow him to achieve something masterful.

The Communications Network: There are places in the U.S. that actually celebrate setbacks. Returning to our earlier point about culture, one of those is Silicon Valley. You write in your book about an event called FailCon, where people share reverses that they’ve experienced.

Why do you think places like Silicon Valley embrace failure? Are there other sectors that you’ve seen do this, too?

Sarah Lewis: It’s a great question. To talk about Silicon Valley, I think, requires that we first remember that the term failure, in America, was first used as an economic term. Failure, in the 19th Century, meant bankruptcy. It meant that you had reached a dead-end. It was only in the 20th Century that we started using the word failure to talk about the human spirit.

Entrepreneurial feats, I think, require talking about these sorts of potential dead-ends and glean from them because of the pivots that people often make that then let their product sort of arrive at an achievement.

If people were to stop with their so-called failures, entrepreneurially, we might never have, in our lives, something like Spanx, which Sara Blakely decided to create, but only did so by thinking about failure very differently.

Silicon Valley has, as you know, something called FailCon. It’s a conference where CEOs will come together, but are only allowed to speak about their failures. What they’re doing is actually replicating what Sara Blakely did every day at her kitchen table when she was growing up. She’s the founder of Spanx, one of the few self-made billionaires in America.

At that kitchen table, her father asked her, “What have you failed at today?” She and her brother were really, in some sense, pressured to offer an answer, because he was disappointed if they didn’t have an example. That line of questioning made her reconsider failure.

This is what I believe is happening at FailCon, as I’ve seen it. It’s allowing for a re-framing process. To consider that word differently, in her mind, to consider failure not as an outcome, but as the refusal to try.

By understanding that the refusal to try is often the very thing that leads to a dead end, entrepreneurially, people are able to encourage one another, I think, by speaking more openly and candidly about their failures in public, not just at a kitchen table. That’s why Silicon Valley, I think, is doing such great work.

The Communications Network: Again, you talked to more than 150 people. You tell a lot of different stories in your book across different cultures. Did you see cultural differences in views about success and mastery and failure? Is there a uniquely American viewpoint on these topics, or European or Asian viewpoint, or did you find some universal themes across all continents?

Sarah Lewis: There are, I think, cultural differences as they relate to failure that come out in this book. Some people have said that this book is distinctly American, and that might be the case. We are, I believe, a culture that doesn’t simply honor and value achievement. I think we value ambition, which is separate from achievement.

I think ambition comes with the sense of valuing something because of the risk that it might not work out. In that way, failure is always a part, always a potential reality of what it is that we’re celebrating.

But not every culture has kind of ambition as their godhead. South Korea, for example, one of the cultures that is, in a way, part of my thinking as I wrote the book because they bought the book so early on, has a very different approach in terms of pedagogy.

The book has sold in South Korea and Brazil and China and Holland and the U.K. All of these cultures, I think, approach failure very differently. In Japan, there’s a notion of noble failure, an idea that some failures can actually be heroic. In the U.K., you see that tradition, too, but I don’t see it so much in the U.S.

As I tour with the book – and I’m about to go to Sydney and Hong Kong and Seoul, South Korea, I’ll be interested to ask more individuals directly what they think about failure, whether it’s taboo in their culture. I assume it might be for some. I’m looking forward to having more answers when I come back.

The Communications Network: What are some of the practical lessons from the book that you would encourage people to keep in mind as they pursue their own life journey and their careers and the work of their organizations? Are there three or four lessons that stood out for you as you did your research and interviewed people for your book?

Sarah Lewis: I should be really clear. The Rise isn’t a self-help book. I didn’t write it to have sort of takeaways in that sense. It’s really a discursive atlas of stories, but there were findings that came out of it, which I love.

We slipped by the near-win earlier, the way that athletes live their lives and achieved their victories through these unusual means. One of the findings, for me, was – whether born an athlete or not – to look at our lives the way athletes do and to rewind the tape the way that they do to glean from our past experiences some lessons that sometimes we would just like to pass by and ignore.

The second thing I’d say is to make sure that we’re including time for play in the context of serious work. I think this is especially important for entrepreneurs or anyone working in an organization that’s trying to achieve something new or innovative.

[pullquote1 align=”center” variation=”deepblue”]We are, I believe, a culture that doesn’t simply honor and value achievement. I think we value ambition, which is separate from achievement. I think ambition comes with the sense of valuing something because of the risk that it might not work out. In that way, failure is always a part, always a potential reality of what it is that we’re celebrating.[/pullquote1]

Two Nobel Prize winners that I spoke to gave me a sense of why play is so important. They are the Nobel Prize winners who discovered the first two-dimensional object on the Earth – graphene, as it’s called – and it’s replacing silicon. It’s really an incredible material. It’s thinner than silk. It’s stronger than steel. It’s the most conductive material that they’ve ever found.

They found it through such rudimentary, playful means that when they submitted their findings to the prominent journal, Nature, the journal didn’t think they actually had a discovery on their hands. They thought that they had to just be mistaken in their findings.

They found that by playing with Scotch tape and graphite, in fact. But, really, they’re sort of exemplary for creating this model of what they call Friday Night Experiments, times where they’re  in a very serious laboratory, allowing themselves to enter into another person’s field of endeavor and expertise and ask questions that those experts might not dare ask.

Other companies have models for doing this as well. Google has 20% time. Lots of different companies, like the Mayo Clinic, have sort of a safe haven that allows their inventors to create without fear of repercussion. The Mayo Clinic inaugurated what they call the Queasy Eagle Award for ideas that didn’t quite make it, but that they still want to honor for the effort that went into them.

Before this experiment with this Queasy Eagle Award, they had a few ideas for patents that were very good, but, after 18 months with this Queasy Eagle Award, they had 245 ideas, many of which merited new patents.

Anything that lowers the barriers to feeling the sense of shame from failure is helpful, and play allows for that.

The Communications Network: We’ve talked about people in the business community and artists, athletes that you have seen enjoy success and mastery, as well as setbacks. Are there stories in your book about non-profit leaders or people in the foundation world that you’d like to share with our listeners?

Sarah Lewis: One of the stories that really intrigued me came from the NGO sector in this sort of foundation world that supports this work. This organization that I’m thinking of is Engineers Without Borders in Canada. They’re doing a lot of work throughout Canada, but also in sub-Saharan Africa. They’re part of a large sector of work that’s going on in the international aid community.

Speaking to some of their founders was illuminating to me on this topic of failure because this is the one sector where disclosing failure publicly can have some serious consequences. I did a talk with Chris Stone at the Open Society that really reinforced this.

The idea that the foundations gave me was that if organizations really had 100% success in achieving their goals – vis-à-vis grant applications – we would have already solved all the world’s problems. Meaning, in order to have some honesty and integrity in the work, people do need to admit their failures.

This was taken to such an extreme that the Engineers Without Borders organization I spoke to decided to publish not just an annual report, but a failure report. That sense of disclosure really ignited a huge conversation in the field of international aid about the repercussions of doing this, but also what can be gained from it, what foundations can learn about best practices from it. I thought that was really instructive. I’d just leave with a quote that Winston Churchill said, which is, “Success is the ability to go from failure to failure with no loss of enthusiasm.” The question is how do we do that?


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