What a joy to have Chase Jarvis (@chasejarvis) back on the show. He is the author of Creative Calling, and his second book is Never Play It Safe: A Practical Guide to Freedom, Creativity, and a Life You Love (Harper Business). It’s available wherever you buy books, and if you head to https://chasejarvis.com/never-play-it-safe/ you can get some bonus materials. Trust me. You’ll want them.
Chase was the founder of the pioneering online learning platform Creative Live. He sold the company, and that catalyzed an entirely uncertain path. The book tracks that journey as he embodies the message at the core of the book that playing it safe is most dangerous thing we can do … creatively speaking. Not, you know, cycling without a helmet or courting disaster down a dark alley.
This book leans heavily on conversations he’s had on his Chase Jarvis Live Podcast, the show where he speaks to luminaries across business and art, people like Brene Brown, Roxane Gay, and Seth Godin.
We dig into a quite a bit like how success leaves clues, the conversation he had with Seth that lifted him up, pivoting from the draft he had previously written to what he eventually wrote, and how volume/quantity matters as it relates to trusting your intuition.
I’ve been following Chase and his work for a good fifteen years, dating back to his time as a premier photographer (which he still is), through his entire journey at Creative Live (not gonna lie, feels … empty … without him at the helm, but that’s largely a projection on my part, I think.), to his writing of Creative Calling, and now this latest book.
I’m always weary of self-helpy books because, let’s face it, many of them beat the same drum, more or less. But Chase’s approach, and his charming way of writing his way through the practical stuff, make the book a light and inspiring read. It’s structured well and addresses many of the issues that keep us painted into corners of our making.
TL;DL: On Intuition
Brendan: There was roughly 13 months of work on another version of this book that you entirely scrapped for what became, Never Play it Safe. So, take us to to that moment of having to essentially abandon such a lot of work to totally pivot.
Chase: So I will say honestly, Brendan, so just as a as just being totally honest and transparent, like I have historically, I’ve been sharing a little bit about the book now that it’s out. And, press and interviews and things like this, and I’m usually the one who says those words, right? I worked on this book for blah, blah, blah, and to have you just read that to me, or share that with me, and me receive those words. I felt afraid. I felt like the hair on my arm stood up. I there was a little bit of like, oh shit. I actually did that.
Essentially, when [Creative Live] had been acquired, I was in a really reflective time, as I just articulated based on your the last question that we were working with there. And I have this a belief that success leaves clues. And so what about the last chapter of my life did I love? What about it did I not want to participate in anymore? And how can I make my life look more like that, more like the things that worked?
And writing was a piece of that. I love to write over and over on the topic like, what do I really want? I journal on that almost every day. One of the things that I came back to was just wanting to be of service to the community that has provided so much for me, and that I feel like the world really gets a lot of value from creators and entrepreneurs and people who are building things. And so I knew that I had a book in there, and so writing every day, that turned into some ideas, and those ideas turned into a conversation with my agent, and they’re like, this is awesome. Let’s do it.
And so I started writing. And there was I’d say, five or six months, a discovery, 13 months of writing, like actively every single day, multiple hours, working with a team of researchers and project managers and writing support and just like all kinds of stuff. And then I found that I was sort of writing what my friend Brene Brown calls gold-plated grit. Like you talk about grit, but you’re doing a pretty good job of shining it up. It started not feeling good about six months into it, and yet the words were pouring out. The words were on paper, and we had basically, essentially, an entire book. Then I started feeling sick to my stomach about it.
And there was a couple pivotal moments just about the timing of the book and where I was and what I was thinking about when I would read the book. And sometimes I like to read books aloud to myself, read my own writing aloud, because it’s a different way of experiencing it. And I knew. I just knew in my heart. And there’s a whole chapter on this in the book, which I think is so powerful. It’s the it’s a chapter on intuition and how, just like creativity, is trained out of us culturally. There’s no evil overlord. But the reality is that society, that’s a mass society, needs to put people, I need to look like this, walk like this, talk like this. And that is a very negative outcome of large especially late stage capitalism, that’s trained out of us. Our natural state is wildly creative, and our creativity is trained out of us. And the same thing is true with our intuition.
Our intuition is one of the most powerful things that we know the least about, and that trusting it so many answers unfold before us and that is another thing that’s trained out of us. So when I became aware that, you know what, this is not the book that I’m gonna put out, as soon as I sort of knew it in my bones, I couldn’t unsee it, I couldn’t unsay it, I couldn’t unfeel it. And so in what I still to this day, feel like it took a lot of courage, and this is why I don’t represent that I’m special or unique. We all feel this fear, and that’s what courage is. Is courage is feeling this fear and doing it anyway. And so I called up my agent, and he is so smart and kind and thoughtful and talented, and he’s like, essentially, like, ‘Bro, are you sure?’ And I’m like, ‘I’m sure.’ And he’s just so thoughtful. I can’t say enough nice things about Steve. And when I was like, ‘This is how it’s going to be. I got it. I’m going to take this ball and I’m around with it.’ This is where I’m going. And I need you to believe in me and trust me, and even if I, if I screw up, the thing that I’m sitting on right now is not the thing I’m that’s not the that’s not the gold.
And I need to be authentic, and I need to do this for the people that for myself, and for the people that I’ve been writing this. I write these books and chapters and stories with individual human beings in mind, like I wrote this thinking about my wife and I wrote this, thinking about this particular mentor, and I write so I’m like, I can’t in good conscience put this out and took it to the publisher with the way I wanted to change it. And they were like, well, I mean, there was nothing really to say. I just had to say, thank you. I’ll be back. And so in eight weeks, I essentially rewrote the entire book of the 65,000 words. I think probably 60,000 of them are entirely new, and that’s a lot, and yet it poured out of me. There was no question as soon as I started, as soon as I went to work, that this was the right thing. And it was in the process of doing that that I was like, what about this is, is so valuable that I can’t not talk about it as the title of the book. And it was the risks that I was willing to take, the risks of being shamed, of not actually delivering, of not showing up, the risk of failure, the fear of success, the fear that I was going to let other people down, that I wouldn’t show up with, with the goods, essentially, and yet, doing it anyway, that is where I found, essentially, the reminder that, Oh, my God, this is where all of the best stuff in life is. In relationships, it’s taking a chance in our careers. It’s deciding to go for our dream job. And when you start and you it manifests in 100 different other ways. How we show up every day, showing up as yourself, is so much easier than showing up as a second rate or false version of somebody else. Like when you realize that all the best stuff is on the other side of our comfort zone. It’s so again, you can’t unsee that. And I realized that that in that sort of moment, that it is this act of not playing it safe.
And to be clear, I do not, I say this in the beginning, I’m not talking about seat belts and sunscreen here. I’m not talking about physical or emotional safety. Those are all important attributes, but pretty much everything else is when we play it safe, we are doing ourselves a radical disservice, because the reality is that all sorts of stuff comes up. Mistakes happen. And if mistakes are going to happen either way, going all in on the things you love and how you want to show up in the world or somebody else’s dream. Stuff’s gonna break and things are gonna go wrong in both those situations. Wouldn’t you rather have those things go wrong with the authentic you? With the thing that you know you can fix, that you’re put on this earth to come back to yourself time and again, and that is where it just all made sense. I’m like, the title, this book is never play it safe.
Parting Shot: On the Responsibility of Platform
I’m in a position where I’m thinking about the public-facing component of writing the book. I’m at the point where I hate the book enough to know it’s done. Like, fuck this book. Hate it. It’s an asshole. Go away.
A big, big part of me doesn’t want to engage in the forward-facing shit I see hundreds of authors do on a daily basis. It’s exhausting. On some level it’s just sad how we’re all clamoring for the finite attention of others. Everyone, on some level, is treating their lives like it’s a reality show: book cover reveals, box cuttings, here’s all my events, and wow, look at all the panels I’m on at AWP, and here’s yet another New York Times column I wrote, and did I mention the Wash Post published another essay.
I guess I hate the hustle. I hate the posturing. I hate the posting of messy desks and I love the posting of messy desks. I don’t want to engage in the hustle. If the book is good enough, it should spread, hand to hand, on its own merit. What can I do? I’ll talk about the book here, as I have for a year and a fucking half, longer if you go back to the proposal journey.
But here’s the thing: At some point, it actually becomes selfish to hide. There are scores of people who bring a book to life. There are scores of people who would kill for the opportunity I have with the publisher I have, with the editor who acquired this book, for the agent who sold it. Mainly, it’s a disservice to the community and an insult to the community if I don’t leverage every asset I’m privileged enough to have earned. Not even sure if I’ve “earned” anything, TBH.
It’s like that scene in Good Will Hunting when Will refuses to leave, to hang around the townies, and his friend, Chuckie, played by Ben Affleck tells Will that he’s sitting on a winning lottery ticket and he’s too big of a pussy to cash it in. And what gets me about the scene, when Chuckie says this, Will is all sick of hearing how he owes to himself, to apply his gift etc. But what drives the point home, the real gut punch of it all was Chuckie saying, “NO, NO, NO, FUCK YOU. YOU DON’T OWE IT TO YOURSELF. YOU OWE IT TO ME.”
There’s an army of people I owe this book to and the most important one I danced to “Pork and Beans” to 14 years fuckin’ years ago. [in reference to the intro of Ep. 433]
So, yeah, I’ll be hustling. I don’t owe it to myself. This game stopped being about me a long time ago. I owe it to you, I owe it to her, I owe it to my editor, I owe it to my agent, I owe it to my dementia-addled mother, I owe it to my sister, to my dad, to the twelve legged beast in HankKevinLachlan, so you’ll excuse the hustle and if you can’t do, interview, see ya!
