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The GOOD Dinnertime Conversation

When you’re trying to fix big problems, some degree of failure is inevitable. Here’s how a few of our favorite creative people deal.

Long ago, failure was simply not an option. Yet this concept has taken an altogether unprecedented turn in recent years, becoming an end in itself. Largely spurred by the business community and abetted by the self-help industry, we find ourselves increasingly being dared to fail, and to do so “upwards” and “early and often”. At the time of writing, the TED website hosted 140 talks on the topic of failure. But how much do we really mean it? And of what value is it to civic life? We invited five friends to our co-founder and chief creative officer Casey Caplowe’s house to shed some light on the matter in the first GOOD Dinnertime Conversation.


Abhi Nemani, first chief data officer for the city of Los Angeles

Ellen Huerta, founder of Mend, an online network and community that helps people thrive after breakups

Casey Caplowe, co-founder and chief creative officer of GOOD

Rudy Espinoza, executive director of LURN, a nonprofit committed to revitalizing low income communities

Margari Aziza Hill, co-founder and programming director of the Muslim Anti-Racism Collaborative

Ben Keesey, CEO of Invisible Children


Casey Caplowe: We tried something like this in our previous issue, but we failed: We had this idea of inviting some interesting people doing cool stuff in the world to talk over dinner, and then to print the conversation in the magazine. But it didn’t work. We did it at a restaurant, which was fun, but the sound was so bad we couldn’t get a usable transcription. We learned a lot from last time, which is perhaps the best you can hope for out of failure. This issue, we wanted to try again, and to have an open, honest conversation about the reality of failure today—about the positives that accompany it, but still do justice to how painful and awful it can be.

Abhi Nemani: I think the question of success and failure, particularly in civic life, is really interesting. We inherently have a hard time dealing with failure because, in the public sector, it’s difficult to talk about success. Success is that which goes unseen. For instance, when the bus shows up on time, we don’t blog about that, right? When there wasn’t a fire in that building, we don’t tweet about that, right? The things we end up noticing in the public sector tend to only be failures.

Margari Aziza Hill: I come from an education background and, as a teacher, you get used to assessments. For instance, your students will assess you and tell you what was good about you and what sucked about you. And you’re naturally inclined to focus on those parts that suck, so that you can be better next time. So, it’s really hard to feel success. Even when you hit that 92 percent, you’re like, ‘Oh, I could have done this better. And if I get this training or if I obtain this skill, maybe I’d be successful.’ And so to some extent, you’re just always feeling like you’re failing.

Rudy Espinoza: In my work, it feels like we’re building the plane as we’re flying because we’re talking about gentrification, and none of us really know how to stop displacement in cities. It requires a level of experimenting, and some degree of failure is inevitable. My organization really tries to embrace failure—sort of like the way that tech companies do. But I do understand why others don’t. I feel like the nonprofit sector is really broken, partially because foundations are so afraid of failure and only invest in things that they know are going to be successful. It’s really hard to experiment in that kind of environment, when you’re always worrying about the next grant.

Nemani: I think it’s easy for someone to give a talk about how his or her company failed and then, oh by the way, they made a billion dollars on their next company right after. But how do we talk about it? Do we actually announce when our organization fails, but that it’s okay? I’ll be honest—for me, it’s not okay.

[quote position="full" is_quote="false"]Even when you hit that 92 percent, you’re like, ‘Oh, I could have done this better.[/quote]

Ben Keesey: My personal experience with failure hurts so much more than the cultural conversation about failing ‘early and often.’ Three times at Invisible Children we went through major moments in which our business model broke, when we didn’t have enough money to keep going, and we had to close down programs and lay off staff. And every time it was five times harder than I thought it was going to be. There wasn’t some rainbow that led me to the next mountaintop. It just sucked.

Ellen Huerta: I’m still in the early stages of my startup, so it’s really interesting hearing you guys talking about failure in an organizational context. I honestly can’t imagine having to deal with the personal weight of failure and dealing with how that affects other people, but working on a company focused on breakups, I’ve been thinking a lot about what happens after failure and how you deal with yourself after failure. And what I’m realizing from a personal standpoint is that I’m so hard on myself in a way that I would never be on a friend or a family member. And I think everyone at this table is probably the same way. A lot of times, the compassion that we have for other people, we don’t extend to ourselves.

Keesey: The question of failure gets more complicated when you have people responsible for your failures, right? And figuring out how you manage your own emotions around that failure, how you manage the emotions of the people responsible, and then how the organization responds are, I think, three different questions. I guess my pushback on the TED talks around failure is that they mostly focus on the CEO’s role in the failure and not really on those other two layers, which I think are just as important, if not more important, because most of those guys who do those talks end up bouncing back.

Huerta: I think acknowledgement is huge. Just simply letting yourself acknowledge when you fail and actually sit with it. I think a lot of times you feel an emotion and you try to escape in some way or avoid it. Or you do something to try to forget it. And a lot of times, if you actually just sit with an emotion and let yourself feel it, it can really help you to process and move forward.

[quote position="full" is_quote="false"]It’s really hard to distinguish between organizational failures and my own individual failures.[/quote]


Keesey: When you want it all, anything less than 100 percent feels like failure. And maybe that’s a great lesson: That when failure and success are just these endpoints, you’re either crushing it or you’re sucking. You know, maybe there’s something in the middle?

Caplowe: There’s something really powerful in that little gap, where you’re not happy entirely, but where you can recognize the amazingness of the 92 percent Margari was talking about earlier. You’re still able to ask, ‘Why didn’t we close that other 8 percent?’

Keesey: I love that point. We can be so crazy with our expectations. Larry Ellison, the legendary CEO of Oracle, has this quote about how he has always felt like a failure because he was never the richest man in America. He never was number one. He was rated between, like, four and eight, with around $22 billion. If you want to make yourself feel shitty, you can always find someone else doing better than you.

Nemani: The tension there, I think, is fascinating, but it’s even more confounding in the nonprofit sector. We work around this idea of eradicating homelessness in Los Angeles—we’ve actually made that commitment over the next three years—I don’t know that I’m going to get there, right? And so the question is: Am I going to feel ok with myself if I don’t? And I think all of us doing mission-oriented things have to find a way to aim for that big number and then realize that actually getting to it is next to impossible. Honestly, 92 percent can be awesome.

Espinoza: I admire everybody who feels that they suck even though they’re awesome, because, to your point, Casey, we are creating the future and we don’t know what it looks like. We’re creating something that’s not there, and we’re trying to measure ourselves with metrics that are already outdated. And at the end of the day, I think it’s awesome when I see people who are pushing themselves beyond the brink. Yes, the whole self-care thing is super valuable and something that I’m learning about in my personal life, but I admire people that are doing work and are never happy because they know that there’s something else to improve upon. That’s what makes the world good, in my opinion. And I always get sort of worried when I see people that are just happy, just like, ‘That’s alright. It’s cool. You know, I’m done for the weekend.’ I’m like, ‘Really, dude?’


Caplowe: Most people tend to really overvalue what they’re not good at and undervalue what they’re good at. Owning yourself in that way is powerful. I don’t know if it’s finding success, or finding contentment, or whatever it is, but there’s something important in not fighting yourself every step of the way. If you come to understand that you suck at something, say, on a managerial level, or on a skill level, like you wish you could code and you can’t code, or you wish you could communicate better and you can’t communicate—it takes so much work to get decent at those things you’re not good at, versus the things you are really good at. If you really put the engine to those, you can become incredibly strong. There’s something to just harnessing yourself in that way.

Keesey: It’s hard for people to see their strengths, because by definition, they come naturally. It’s not hard to do what you’re good at. You’re good at it. So it’s kind of easy. And you focus elsewhere.

Nemani: Organizations have metrics. They have key criteria, right? When you guys assess your personal failures, are there key things you look for? How do you assess? I’m always trying to think about that because it’s really hard to distinguish between organizational failures and my own individual failures. And so I try to think about both and set up key metrics for the organization, and then key priorities for myself.

Keesey: When I assess myself, the thing holding me back usually is fear—of confronting something or doing something that I know I should do is hard. And that realization can be taxing and takes energy. So I sometimes just brush it off and pretend it’s not there.

[quote position="full" is_quote="false"]I admire everybody who feels that they suck even though they’re awesome, because, to your point, Casey, we are creating the future and we don’t know what it looks like.[/quote]


Caplowe: Ellen, I can imagine a lot of fear leading up to your decision to leave Google and start Mend.

Huerta: So much fear. And it didn’t go away when I made the decision. I think that people kind of assumed that when I left, I knew exactly what I was doing, and that the hardest part was behind me. But I feel like, when I made the decision, I was still fearful, but I just kept going. I guess I kind of used it as a motivating force.

Caplowe: What about for you, Rudy? You went from having a seat on the board to being an executive director?

Espinoza: I think I was just driven by this anger and also this crazy clarity that there was so much potential to do something different. And so I guess that’s not the answer that’s relevant to this conversation, perhaps, but that’s what it was for me.

Hill: I guess my motivating force was frustration. Doors didn’t open for me so I had to build the door, build the house, and just utilize whatever skills and talents I had. But it is that frustration that still motivates me, and it’s connected with a kind of anger that came when people doubted my ability to succeed. I just said to myself, ‘No, we’re going to do this, we’re going to do this groundbreaking stuff. We’re going to organize a Muslim-led Black Lives Matter protest; we’re going to organize the first regional Muslim anti-racism conference with only $7,000.’


Keesey: You know what helps me think about failure and success? This probably sounds weird, but, going to funerals. I have this really weird hobby because I went to a Scottish-themed high school and learned how to play the bagpipes. We were the ‘Helix Highlanders’ of San Diego. Our mascot was a Scottish warrior. We had a bagpipe group with our marching band. So, I learned how to play the bagpipes in high school. And, as a result, I actually go to a lot of funerals to play. And every time, it’s so poignant when you hear people talk about what matters when someone has died. It’s not the kind of stuff that we normally think about—more the simple stuff like how they treated their family, the ways that they showed up when their friends were at a low point. So it has helped me get balanced. When I stress out about wanting to live this big life and do something big and important, I remind myself: ‘No one cares. We’ll be dead! Make other people feel good instead of bad. Make people in your life feel respected. Just shrink it all down to that.’

Caplowe: Can I ask you a question, Ellen? You’re working in a space that is kind of defined by failure. Or is that an unfair characterization?

Huerta: That breakups are failures?

Caplowe: Or just that the ‘failed marriage’ is an idiom that we don’t apply to other things. I don’t know that we ever refer to a ‘failed career’. I’m just curious what things you’ve learned from diving into that murky, uncomfortable territory of broken relationships.

Huerta: The way people approach breakups is changing because the nature of breakups is changing. For one thing, people are living longer—we’ve never really had to be married to someone for 80 years until now. And so I think that people are being less critical when relationships end. Sometimes things just don’t work out. Sometimes people grow in different ways and sometimes they need to pursue their own individual paths. I’m seeing people approach breakups no longer as these huge failures, but more like learning experiences. And that’s a maturity shift, I think. I notice that there are increasing commonalities in what people go through during breakups. The biggest one is that everybody blames themselves. I am starting to see a big trend in which people see breakups as opportunities for self growth. A lot of people go through a breakup and they’re not as much focused on getting into the next relationship as they are on reassessing every other aspect of their life. Am I happy with what I do? Are my non-romantic relationships in a good place? Do I need to get my finances in order? I think there’s much more focus on growing as an individual versus just getting back on the dating horse.


Huerta: Not to change the subject, but I’m wondering whether any of you guys meditate?

Keesey: Sometimes.

Caplowe: Not often enough.

Huerta: For me, meditation has been probably the most powerful tool to overcome not only personal challenges, but professional obstacles. There’s this quote, and I’m probably going to butcher it, but it’s something to the effect of: ‘All suffering comes from resistance to what is’. And I think that’s kind of what all of us have been talking about today when it comes to how we think about failure. Sometimes you do have to learn to let go of things. I think that’s really hard for people who are trying to push the world forward. You don’t want to feel like you’re not reaching your goals. But you have to take the time to just enjoy the present moment, and as strange as it sounds, enjoy things as they are. And I feel like meditation has really helped me with that in a way that no strategy session has.

Caplowe: It’s funny because, you know, everyone knows ‘The journey is the destination,’ right? Somehow in our work, that attitude is totally nonexistent. No one’s like, ‘Oh yeah, this problem is exactly where it’s supposed to be.’

Espinoza: One of my good friends said, ‘Rudy, you should check out this book called Things Fall Apart by Chinua Achebe.’ There was this moment when she hit me up with this book when I was desperate for peace, so I read it. And Achebe talks about how it’s important for us to be okay in impermanence and about leaning into that space. Like exploring it and being peaceful about it in a way that we can ask ourselves why we are so uncomfortable in it. And I think it has helped me a lot in my work. When I’m not sure what the next step is, I just take a moment to pause and remind myself, ok, this is a moment of impermanence. The things that I know right now will change, and that’s just the way shit goes. And how can I lean into that and learn about myself in that process, you know?

Caplowe: There’s something there—in leaning into fear and things you don’t like to do. When something is not what you want it to be, don’t retract from that, but be like, ‘Ok, I want to engage that, I want to be there with that.’ And you know, work into that, be into that.

Keesey: Lean In would be a great book.

Espinoza: Anyone ever read the Steve Jobs biography by Walter Isaacson? Steve Jobs was just a dope dude. He was kind of crazy, but he had such a love for his product. And he wanted everything. He wanted to work with the best people, and he wanted everything he worked on to be the best. Even the internal design of computers. There are these scenes in the book where he’s just like, ‘That’s ugly! Just because it goes inside the mainframe [and no one will see it] it still should be nice, and this is how you should lay it out.’ And they’re like, ‘But dude, no one’s going to see that.’ And he says something to the effect of, ‘I’m gonna see it, and I’m gonna know that it’s there. Change it and make it look cool.’ There was such a love to his work.

Huerta: That reminds me of when Michael Jordan stopped playing basketball and went to play baseball. And it seemed at the time—and this is just how I perceived it when I was young—like everyone thought he was crazy for leaving. He was such a great basketball player, but he decided to try to be a baseball player. Now I’m not a sports fan, but I think in a lot of ways that move was seen as a failure. But for some reason, I always think of that as being a very courageous thing. And I keep this image of Michael Jordan in my mind, so when I come up against things, where I’m really scared to fail, I think about him—not Michael Jordan the basketball player, but the baseball player who failed and survived.

Keeping Going

Keesey: What’s hit me the most in this conversation is the idea that the only true failure is quitting, or cynicism. I hope that that comes across. Because of my personal journey—going from JP Morgan to Invisible Children—I spend a lot of time talking to college students about how to find their passion and how to do something important. Working at Invisible Children was this giant, life-changing thing for me, and so I love talking to other people on that journey of trying to follow their heart. But it’s so freakin’ scary. And usually people don’t follow their hearts because they’re scared of not succeeding when they do it. So it’s the fear of failing at something that means something to you is so powerful that you actually never even try it. There’s that cheesy quote that you see floating around Instagram all the time: ‘If you were guaranteed to not fail at something today, what would you do?’ That’s such a powerful idea. I just hope that can be a guiding message: Everyone blows it, there are fumbles all the time. Everyone quote unquote fails. But the only true failure is deep cynicism.

[quote position="full" is_quote="false"]Usually people don’t follow their hearts because they’re scared of not succeeding when they do it.[/quote]

The evening was hosted and facilitated by First Seating, a company specializing in bringing people and organizations together to discuss important ideas in an engaged and thoughtful way—and often over a good meal.

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