If you’re an artist or entrepreneur, you should know Jonathan Fields. Next to Seth Godin (sorry, Mr. F., nobody ranks with Seth), Jonathan’s insights–creative and commercial—are in my opinion the most original and far-ranging. He has a new book called Uncertainty, which just came out a couple of days ago. Jonathan was kind enough to sit still for a quick interrogation:

Jonathan Fields

SP: The subject of learning to operate effectively, despite finding oneself in a position of uncertainty is a fascinating one. What I’m curious about is why you chose it? It’s actually quite esoteric (which I love) and unexpected (which I love too). What hooked you about this idea, enough to make you want to explore it in-depth in a book?

JF: I started with a simple realization. The greatest creations and experiences, from art to business, happen in the fray. Those moments where you’re willing to lean into the unknown and act in the face of uncertainty. To live in the question long enough for insights, solutions, revelations and ideas to arrive that would never have come through a shorter, less-exposed dalliance. Nothing worth creating ever comes from waiting for perfect information or absolute certainty.

Problem is, living in the question kills most people. We are wired to experience action in the face of uncertainty as fear and anxiety. Our brains’ fear centers, the amygdalae, light up and make us want to run for the hills.

But, then there are these seeming exceptions to that rule. People who appear to possess a near superhuman tolerance for uncertainty and even the ability to stalk it in the name of creating bigger, badder, cooler stuff. I wanted to know if that ability was something you’re born with or whether it’s something that’s trainable. And if it could be trained, then how.

Truth is, I’ve been fascinated by this question for years. But my experience as a New Yorker on 9-11 and growing exploration of Eastern philosophy likely played a role in inspiring me to start looking more deeply into the answer.

I put that exploration into high gear about two years ago and what unfolded not only radically changed the way I create, it also had a profound impact on the way I live my life and on my ability to find a center in a world where disruption is the new normal.

SP: You and I talked, when you were writing Uncertainty, about the great poet John Keats’ concept of “Negative Capability.”  Here’s the quote from a letter Keats’ wrote to his brother:

… at once it struck me, what quality went to form a Man of Achievement especially in literature & which Shakespeare possessed so enormously – I mean Negative Capability, that is when man is capable of being in uncertainties, Mysteries, doubts without any irritable reaching after fact & reason … This pursued through Volumes would perhaps take us no further than this, that with a great poet the sense of Beauty overcomes every other consideration, or rather obliterates all consideration.

My question to you, Jonathan: Is the capacity to act amid uncertainty “romantic?” Is it “poetic?” Does your philosophy see a connection between the pursuit of “beauty,” as Keats phrased it, and contemporary entrepreneurial marketing/publishing/commerce?

JF: Romantic, yes. Poetic? No doubt. But there’s also a deep truth to what Keats was saying. It’s as relevant today, and in every creative endeavor, as it was the day it was written. Because it’s based in human nature. And as much as the circumstance of our existence evolves, our primal nature remains largely unchanged.

We still crave certainty. We’re still terrified of acting in the face of it, failing and being judged. Revealing the essence of who we are, and being rejected. Spending months or years following one path, project or endeavor only to have it crash and burn.

Uncertainty

Great businesses and marketing thrive on differentiation and innovation, a willingness to go where nobody’s gone before. Great books take the reader to a place that’s real and exposed enough to make the writer nervous about bringing them, letting them down or worse, letting themselves down. Great publishing is one giant swan dive into the abyss of ever-changing taste. Great commerce is about solving a problem or creating a delight in a way that’s never been done before. And great art is about revealing a part of yourself that’s real enough to bypass thought and speak straight to emotion.

All of these things come from a willingness to be in “uncertainties, Mysteries, doubts” long enough for genius to emerge. But, to do so “without any irritable reaching after fact & reason,” raises a host of questions when you’re creating something with clear commercial intent from the get-go.

Especially in a world where technology lets us bring potential consumers into the process at even the earliest stages and, gulp, elevate them to the level of co-creators. The very thought of this raises a range of knee-jerk reactions about dilution, bastardizing and selling out. But to cling to those arguments by default, rather than explore how the creative landscape is evolving, is I think a huge mistake. I actually spend a chunk of time on this very issue in the book. It’s a thicket, but one that’s ripe with incredible creative opportunity if you understand how to leverage what’s really going on, and you’re willing to be not just an artist, but a leader.

SP: Here’s a question you’ll hate. What should we artists and entrepreneurs keep in mind when we find ourselves in positions of creative uncertainty? Can you give me three axioms or principles to keep in mind?

JF: One—Kill the butterflies, kill the dream. The butterflies have to be there. They’re not fun (though you can learn to experience them very differently), but they are visceral signposts that what you’re doing matters. When you backpedal to the point where you no longer feel them, you simultaneously gut whatever it is you strive to create. You destroy your quest not because you didn’t have the vision or creative ability, but because you couldn’t handle the emotional toll of the journey.

Instead of pulling back, train deliberately and intensely in the alchemy of fear, then march forward. Learn the personal practices, workflow adaptations and environmental shifts that will allow you to not only live in the question long enough to create great things, but invite and even amplify uncertainty in the name of taking your creative potential to an entirely different level. Learn to harness and ride, rather than hunt and kill the butterflies.

Two—Question and reframe. For every story you tell yourself that paralyzes you, there’s an alternative storyline that would mobilize you. When you catch yourself in “I suck land,” stop what you’re doing, take a step back and ask whether the story you’re telling yourself, the questions you’re asking and the model of the world or current situation you’ve created is the only story, question and model. Or, is there an alternative that would allow you the space, confidence and fortitude to move forward.

When I left my past life as a big-firm lawyer to take a $12/hour job as a personal trainer, everyone kept asking “How can you justify giving up so much? Power, prestige, a future as a partner, the money it took to get you where you are?”  I responded, “You’re asking the wrong question. The right one is, ‘At 30 years old, how could I ever justify limiting the next 40 working years of my life by what’s happened in the last 7 or 8?'” Asking a different question allowed me to reframe the answer, to tell a different story that fueled action and creativity, rather than paralysis and futility.

Three—Build uncertainty scaffolding. Interviewing a wide range of world-class creators across a wide variety of fields, from novelists to CEOs, I’ve been able to discern certain patterns. Some of which many of these amazing people weren’t even aware of.

Blended with a healthy dose of research on the intersection between neuroscience, mindset, creativity, innovation and mood, I discovered a set of daily personal practices, habits and workflow adaptations that, over time, not only profoundly disempower the fear and anxiety of creation, but also allow you to tap into a wellspring of creativity and innovation that often lies dormant.

I talk about these in Uncertainty, but one basic example under the “daily practice” category is attentional training, most often explored in the form of mindfulness or meditation. Twenty or thirty years ago, these practices lay on the fringe of mainstream society (California notwithstanding, lol). Now, with a substantial and growing body of research around how they impact not only health and mindset, but cognitive function and creativity, it’s hard to understand how any committed creator might justify not embracing them.

SP: You launched a trailer for Uncertainty and, at one point, you seemed to almost lose it on camera. A lot of people would’ve edited that part out. Why did you keep it in? What’s the story behind this?

JF: Trailers are the shiny object du jour in book marketing. As someone who helps teach authors how to launch books, I spend a lot of time tracking launches and trailers. With rare exception, they’re all really bad. They don’t entertain, nor do they make me want to buy the book. I didn’t want that to be me, but I couldn’t figure out a concept that was capable of doing both well. And it wasn’t enough for me to just create a marketing piece. If I was going to create content, I wanted it to have standalone value. So I’d resigned myself to not doing a trailer.

Then this idea came to me. I’m obsessed with storytelling. No flash, no glitz. Just one person telling a story in a way that captures people, takes them through an emotional journey. That’s what I wanted to do. So I decided to tell a story about a very brief experience, something that happened shortly after 9-11. There was no script, no storyboard. No special effects. Just me telling it the way I remembered it, then sharing how it impacted my exploration of uncertainty.

I also knew the few times I’d shared it before, I’d gotten pretty emotional. And I wasn’t sure if I’d be able to really keep it together for the shoot. So I thought about telling another story or doing something else. But that didn’t feel right. The book is acting in the face of uncertainty in the quest to create experiences that matter. I had to follow my own message.

The day of the shoot, I sat in a small studio in Brooklyn with two cameras and Chihuahua named Dougie trained on my face. I began to speak and, as I suspected might happen, when I got to the part that creates the strongest visual memory for me, I got upset. I took a few seconds, exhaled slowly, then continued. The cameras kept rolling.

Eleven minutes later, the director yelled cut.

I looked up. That’s it, she said. One take. We’re done. We’ll do it again, but just to get some different angles.

Two weeks later I got the rough cut. I’d surrendered control over the editing to my team. They kept the moment in. I was uncomfortable showing myself that way to the world. Being vulnerable on that level. But, I also sensed it had to be there. That was the most powerful moment in the footage. It’s what made it real.

A few days later, I took a deep breath in as I hit publish on the trailer. Within minutes, emails began to flood in. People were sharing their own stories. Hours later, thousands had watched it, shared it, and commented on it. I sat nearly the entire day, taking it in, embracing the connection that’d been created, lump in my throat unable to speak.

I took a risk with a little piece of my soul, and at least this time around, it’s seems to have hit home.

SP: Thank you, Jonathan. [To see the trailer, click here). Now lemme rethink what I said about Seth …