How to Find the Heart to Start with David Kadavy

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If you’ve ever looked at a blank screen or canvas or an empty rehearsal room or auditorium and felt paralysed with fear and self-doubt, then this week’s interview with David Kadavy is for you.

It’s also for you if you find yourself looking at the achievements of your creative heroes and top performers in your field, and comparing your own situation with theirs, and wondering what you could possibly do to compete with them.

Back in 2004, David was in this position himself – sitting in a cubicle in Nebraska, reading the blogs of successful people he admired, and wondering if he’d ever make it out of the cubicle and create the life he dreamed of.

Fast forward to 2018, and David is a best-selling author and the host of the popular podcast Love Your Work, living the internet dream as a writer and creative entrepreneur in Medellin, Colombia.

In this interview David joins the dots between 2004 and today, and shares how he found the heart to get started – and to keep going in the face of obscurity and adversity.

He also shares practical tips from his book The Heart to Start, including what he calls motivational judo, a powerful and counterintuitive approach to outwitting your own perfectionism and procrastination.

In the course of the interview David talks about his ‘best AND worst blog post,’ which you can find here. And at the end of the interview David sets what I reckon is the strangest Creative Challenge we have ever had from a guest!

If you enjoy The 21st Century Creative then I think you’ll also like David’s podcast Love Your Work, which touches on many of the themes we look at on this show, around using your creativity to carve out an unusual career and find your own security in an uncertain world. In fact, David interviewed me for his show in the ‘return match’ for today’s conversation – you can listen to our conversation on The Heart to Start here.

So without further ado, it’s time for us to get started, by listening to David Kadavy’s advice on finding the Heart to Start.

David Kadavy interview transcript

MARK: David, you’ve written a great book to help people with a challenge that I think we can all relate to, and that’s staring at a blank page or canvas or whatever the equivalent is, and then looking at the amazing achievements of successful people in our industry or art form and being paralyzed with fear and doubt.

So how did you find the Heart to Start in the face of all of this?

DAVID: Well, it was a long process. It was such a long process that I had to write a book about it just so I could get over it myself. An interesting thing about the book that you’re talking about, The Heart to Start, is that previous to writing that book I wrote a different book and then I found myself something like six years later having not written another book yet.

And so that’s where this book came from, was the things that I wanted to instill in myself every time I found myself procrastinating on creative work or on any sort of aspiration, I call ‘aspiration procrastination,’ – that we are familiar with procrastination in a traditional sense such as that we are procrastinating on taking out the trash or in going to the dentist and, there’s not much mystery in why we procrastinate on those things. But then we procrastinate on these things that we supposedly want to do, that we in fact dream of doing.

MARK: Yeah.

DAVID: Yeah. That we in fact dream of doing, right? And for some reason, we procrastinate on those things. So that’s very interesting. I wanted to really deconstruct that and deconstruct the ways that I had personally managed to somehow miraculously create some things in my lifetime and look at the ways that other people have overcome certain mental barriers or paralyzing thought patterns and develop a framework of thinking about why it is that we procrastinate on our creative aspirations.

And I’m finding it useful, I am constantly running up into situations where I’m finding myself falling for the very same traps that I warn about in the book, and then deciding like, ‘Oh, I need to stop inflating the investment. I need to stop falling for the fortress fallacy. I need to crack the whip,’ like all these different concepts that I’ve introduced in the book. And so that, on a very basic level, is how I have found the heart to start, was through writing this book itself, for myself.

MARK: And can we pull out one of those techniques then and give us an example of where it came from and how we can use it?

DAVID: Sure. One I just mentioned, the ‘fortress fallacy.’ This is this thing that I fell for so many times. I still fall for it all the time and I catch myself. And I find so many other people falling for it. And that is that our dreams, the things that we envision creating, they can be a guiding star for us. They can help motivate us and move us forward. But at the same time, those dreams can be very intimidating. And the reason being that we almost without exception envision something that’s well beyond our current abilities in terms of not just quality, but also scope and scale. Say we’ve hardly done any writing and we’re imagining writing this whole novel, and so we imagine then that that is the way that we create that thing is we sit down and we just write a novel.

Well, it doesn’t really work that way. That’s something that I’ve learned from talking to lots of creators, that’s something I’ve learned from creating things myself, is that well, instead of going for the novel, maybe you can sit down and write a short story. Maybe you can sit down every day and write a 50-word story or a 10-word story, you know? Start with something very small and then you start to develop this skill or vision muscle of being able to imagine something in your mind and imagine the steps to get there, and then actually be able to make that happen.

So that’s something I catch myself doing all the time is I’m daydreaming about something and I have this wonderful vision in my brain, but then I feel this paralysis taking over me and I realize, ‘Oh, well, all I need to do is scale down the thing that I just thought about and take action on some other thing, with that guiding star, that dream, still there to guide me, but with a goal that’s in front of me that’s a little more easy to actually achieve.’

MARK: A nice example of this in the book was what you called your best and worst blog post. Could you tell us about that please?

DAVID: Sure. So it was May 2004, I was in a grey cubicle at an architecture firm in Nebraska, and I had been reading all these blogs that I thought were so great, blogs like Seth Godin’s blog. Douglas Bowman had a blog. He was or is the designer for Google and Twitter. He works for Twitter as well. And there were all these wonderful blogs and I felt very intimidated by those blogs, because they were writing brilliant things and they had very well-organized blogs, and I didn’t know how they made them. And this is 2004, so blogging is pretty new at that time.

And so I had been procrastinating on that for many, many months. And so finally, something happened that evening. I was at the office late and I just opened up blogger.com and I’m telling myself as I am trying to think of, ‘Oh, maybe I need to pick a different template,’ or ‘what should I call it,’ or just publish the first post, just publish the first post, just publish the first post. And what I ended up writing, like I said, was the worst blog post I have ever written, in that it is, you can still see it up there. It is a run-on sentence, or a run-on paragraph, really.

MARK: Should I link to it?

DAVID: Sure, yeah. My first blog at kadavy.net is a run-on paragraph. I’ve got a misspelling in it. There’s no point in it. But what I’m talking about in that post turned out to be really prescient. I was just writing whatever was coming to my mind, and the thing I was writing was, ‘I don’t know why I’m doing this.’ Maybe I’m going to write about web design or something. Sometimes I get overtaken by a sort of paralysis where I’m trying to think of how to make something perfect and that keeps me from taking action, but now I’m just going to barf this out and clean it up later.

And that’s essentially what I said in that blog post and I didn’t know at, the time I had no idea, that 14 years later, I’d be still having that blog on this podcast, I guess it’s getting to close to 15 years now, and that I would have books published and have done many things that all stemmed from starting that blog, all stem from that one little start, even if it meant that all I did was talk about the fact that I didn’t know why I was doing it.

MARK: And I love the way you talk about the kind of ‘motivational judo’ that you used on yourself, that you put something out that you knew wasn’t great, but then you say the very fact that you’ve started propelled you to do better.

Can you say something about that kind of judo approach to perfectionism?

DAVID: Yeah. Motivational Judo is one of the concepts that I introduce in the book, and it’s basically getting to understand your own things that tend to hold you back or your own ways of procrastinating and finding ways to overcome that, because as I understand in the martial art of judo, you use your opponent’s energy against your opponent, is that if your opponent is coming at you, you use that momentum to throw them over your shoulder.

And so with Motivational Judo, you’re trying to find those things about your own personality that you can exploit in order to get yourself to keep moving. So for a lot of people that’s going to be some sense of quality, and so by simply starting, even if it is something that’s not up to the standards that you hold in your mind, not up to the fortress that you imagine in your mind, you start with just a little cottage and that’s not a very good cottage. Then you have this living breathing thing out there, especially with something like a blog, is that you can write a bad post today, and you can write a better one tomorrow and then you can write a bad one again but then every day you can add to it. And so it’s this living, breathing thing, and just the mere existence of that thing, by making it exist, by putting the clay on the table in front of you, you can keep molding it and keep moving towards something.

And so that’s something that I was surprised to learn in doing that, in actually getting the stuff out there, and it’s something that I continue to try to catch with myself is that when I’m procrastinating on something, to try to find, ‘Oh, where’s the way that I can kind of trick myself into what’s the action that I can easily take now that will manipulate a certain personality trait that I have that will thus cause me to continue moving with this project?’

MARK: Right, I mean I can certainly relate to this with writing poetry. I think very often when I write, I get an idea for a poem and it’s not completely clear and I’m almost saying to myself as I write it down or I type it, ‘Well, it’s not this, but it’s something a bit like this,’ and I’ll splurge it, and I’ll get it down there and once it’s there, it irritates me because it isn’t right yet, and so I won’t leave it alone.

I’ll keep playing with it, so Scrivener on the phone, I’ll play with it in odd moments, I’ll keep opening it up in between other things when I’m working. I pin current poems up on the whiteboard in the office. So that I have to walk past them on the way out of the office and back in again. And I look at it and I just take a pen and start correcting it or improving it on the whiteboard.

I just find that that really resonated for me, that tip about just get something out, and then your perfectionism can go to work.

DAVID: I’m curious, if I can ask you a question. When you do get that first bit out, is that difficult for you? Is there something that you tell yourself to be able to get over that initial desire for quality?

MARK: There’s got to be something there that sparked an idea or usually a line that comes that I thought, ‘Yeah, okay, it’s going to be… it’ll be a bit like this,’ but it’s almost like I said, that I’m saying to myself, ‘It’s not this, but…’ so, you know, ‘It’s not this.’ I’m giving myself permission to write this down even though it’s a bit ham-fisted and it’s not very well expressed and it just feels a bit awkward, but as long as there’s something there then I feel like I’ve got a bit of plasticine to play with.

DAVID: I always have to feel like I’m being a little reckless in getting that first bit out, it’s that I’m just trying to overcome this feeling of paralysis and I’m just trying to keep moving, and I guess that’s why thinking about barfing it out is something that’s very helpful for me is that I, even on my task management, I won’t put like ‘write a draft,’ I’ll put like ‘write a barf’ of this for like the first initial thing, and that is just priming my brain, giving me permission to just get anything, anything at all out there. And I find that that’s something I have to continue to practice. If I’m not on almost a daily basis giving myself that permission to barf it out, to just really get something out there, then I feel that resistance starts to build up again and then I get caught in my head and I get paralyzed again.

MARK: So 15 years ago, you wrote that blog post, almost in spite of yourself as you say, and you were in this grey cubicle in Nebraska, and here you are, in Colombia? Am I right?

DAVID: Right. I live in Colombia now, Medellin, Colombia.

MARK: Right. And you’re living the dream, you’ve got this great podcast where you get to interview the good and the great, and a bestselling author.

Can you join the dots a little between that grey cubicle and where you are today with your life and your business?

DAVID: I’ll try to do it in a somewhat coherent manner. I guess I’ll try to, I’ll start with short, and then you can dig deeper on if I can keep it short. So thanks in part to that blog, I got discovered by a startup founder in San Jose, California, in Silicon Valley. And then I landed a job as a web designer in San Jose, ended up living in San Francisco, lived in the Silicon Valley area for about three years. The final year of that was a year that I spent on my own, working on my own projects, wandering from café to café, and then I left Silicon Valley in the midst of a boom, with job offers kind of nipping at my tail. Around 2008, I felt like I had something inside of me that I’d wanted to discover and I wanted to figure out what that was and I wanted to get that out and I felt like I needed space and I felt like the Silicon Valley startup scene was, it was just noise to me at that point. It didn’t feel relevant to me.

And so I moved to Chicago, where I rented a two-bedroom apartment in Ukrainian Village for the same price that I was paying for a tiny bedroom in the Mission in San Francisco and gave myself the space and the time to really dig in in some cold winters as well, which as something that I had been accustomed to growing up in Nebraska is those cold winters where there’s nothing better for you to do but sit inside and work on something. And so, through that process after a couple of years of searching, I ended up getting a book deal to write my first book, called Design for Hackers. Through that book doing pretty well, I ended up flying all over the world, speaking in various places, I got to travel quite a bit. And through that experience I discovered how much I enjoyed Latin America, and eventually ended up moving down here to Colombia about three years ago, and that was about the time where I decided that I wanted to be a writer.

Now that’s an interesting conclusion to come to when you’ve already written a book and it’s done well and it’s been a few years since that, but that was the time where I really said I want to double down on this wonderful process of being able to read books and to talk to the authors who have written those books, people like you who are on the podcast or about to be, and learn things, and then share what I’m learning along the way and be able to share the whole process and create products such as books through that.

And that was the time when I finally realized that I wanted to do that and Medellin became a wonderful place to do that. I had already spent time here and found that I did some of my best work here because I can keep in such a good rhythm, the weather is perfect all the time. The sun sets at the same time all year round, which is an interesting feature, because you can always have a regular bedtime and wake up time that is in the rhythm with your surroundings.

And so that was about three years ago, and I’ve really loved the process of getting used to living here, and living here, and it has resulted in what I think is some of my best work that I could do at this moment in time, and hopefully there will be more and better work in the future. And so I guess that is the not so short version of how I ended up here in Colombia from that grey cubicle in Nebraska.

MARK: Well, that’s quite the journey! And one thing that really strikes me listening to that, you could never have predicted that that blog post, like the butterfly flapping its wings in the Amazonian rainforest, would have unlocked that chain of events.

DAVID: Yes.

MARK: It was certainly not obvious that writing the blog post would lead to Silicon Valley, would lead to the book, would lead to speaking, would lead to traveling, to the podcast, etc.

DAVID: Yeah. If you trace back the cause and effect it really does all come right back down to barfing out that blog post, that terrible blog post.

MARK: That great blog post. Right?

DAVID: Right. Yes, so exactly.

MARK: And this is such a great example of what you talk about in the book, that if you actually get started on something, it almost doesn’t matter where you start, as long as you’re, obviously, you’re going to continue and you’re going to improve and you iterate and things start to happen that you could never have predicted.

I had a similar experience with my first blog. I had a very limited idea of what was possible. I thought I was going to be just selling training and coaching to agencies in the London area, and then suddenly I had all these readers all over the world and then all kinds of weird and wonderful stuff started to happen following on from that.

Which leads me toward my favorite themes of your book, is curiosity. So you say, ‘Your curiosities may seem to take you off course, but when they converge, you’ll be untouchable.’ What do you mean by that?

DAVID: Right. So I guess I’ll go back to the point when I really started to be on my own, which was that final year that I was in Silicon Valley. I decided that I wanted to figure out what I want to do. I just wanted to reconnect with my curiosity. I wanted to reconnect with the feeling that I had as a child, being alone in my room drawing and just losing track of time. And I felt like I had really lost connection with that. I felt like I had kind of gotten burnt out from working for other people and working according to other people’s initiatives and what paces they wanted to work at and such. And so I really wanted to connect with that.

And during that time, there was this YouTube video that I watched over and over and over again, and it was the Steve Jobs Stanford commencement address, where he talks about curiosity. He talks about that you can’t connect the dots moving forward, you can only connect them in reverse. And it was that feeling of when somebody says something and you say to yourself like, ‘Oh, I’ve thought that so many times, but I’ve never been able to put that into words. And every word that they’re saying rings so true to me.’ That was the way that I felt. I mean it just brought me to tears. I felt so strongly that if I followed my curiosities, that it would be scary, because people think you’re a dilettante and they want to know why are you doing this thing and you’re doing that thing, etc.

But the big secret of all that is that eventually those curiosities converge and you end up in this place where nobody else can go, because you can work harder than anything on the things that you are curious about. Like if you can find yourself spending an unreasonable amount of time on something, you’re losing track of time, you can spend an entire weekend working on this project and you don’t have any idea why but heck you’re doing it. Nobody else is going to do that. Because nobody else has that fuel that is going to drive them forward. And so what happens is you get a couple things that are going that way, and maybe you’re not the best in the world at this one thing or that other thing, but those things converge and then all of a sudden you have this new combination, and there’s nobody else in the world that can touch you.

So this is something that I experienced with my first book, which was called Design for Hackers, and it was born of my experience: one, being really, really interested in design and studying design, and then I ended up working in Silicon Valley, so I got to understand this entrepreneurial spirit, this hacker spirit of let’s tinker with some technology and see if we can come up with a company, and that’s how companies like Facebook were born.

And so I got to understand that mentality. I had the design theory background, and I had some writing on my blog. I was not the best in the world at any of those three things, not by far, but by the time those things converged and I wrote a blog post and it was popular and then a publisher reached out to me and offered me a book deal, I could feel confident and secure that there wasn’t competition. It’s not like there aren’t other web design books, and there’s other really great web design books and there’s web design books that are out there that are way better than mine in certain aspects. But the way that I ended up approaching it became my own unique way of doing it, and it was wonderful that it resonated with people.

And it was so wonderful to have that experience happen, especially years after the fact of sitting there watching this video, thinking to myself like what he’s saying is totally true. I have no evidence of that in my current life, but if I keep on believing that and keep on moving forward with these things, something is going to emerge from that.

MARK: And I think this is one of the big strengths of having multiple creative interests. I see this a lot with clients and I can certainly relate to it myself. On the one hand, you’re open to being called a dilettante and Jack of all trades and so on, but actually, if you trust the curiosity and it leads you in several directions at once, then you end up having a very unique blend of skills. So for instance with your book, you didn’t have to be the best designer in the world or the best coder in the world, maybe not even the best author in the world, but the fact that you were curious about…

DAVID: None of those!

MARK: … all three of those things, you found yourself in a unique space. And you ended up in what, in the top 20 of Amazon when you launched the book, right?

DAVID: Right, yeah, the first day, amazing for a book in this niche. I remember my editor at Wiley saying, ‘You know, if we can get in the top 20 of the computers and internet category, that’s a really good goal to go for.’

MARK: And that would be great.

DAVID: Yeah, it would be wonderful. And so lo and behold, the book was number one in computers and internet, in that category, and then it was top 20 all of Amazon. I was ahead of Tim Ferris and former U.S. Vice President Dick Cheney and all these great authors, just for some shining moment. And so, yeah, it really struck a chord with a certain group of people.

MARK: So where did you go after that? Top of the Amazon charts, what happened next?

DAVID: Well, I guess that was an experience that it took a while to adjust to, and I don’t think I got it right right away. I hadn’t been in a position like that before where suddenly, you’re not being recognized on the street or anything, but like if you go to a conference, people recognize you and they come up to you and they want to talk to you or, just suddenly, I was the same person, but now I’m a bestselling author or whatever, or that’s the way that people saw me. And it changed the way I saw myself as well. And so that was an experience that took a lot of adjustment, in one because I had spent so many years struggling trying to get that point, not really knowing exactly what I was searching for.

And so in one way, I felt vindicated, like, ‘Oh, well, finally I’m being recognized as this person that I’ve known myself to be for so long, this brilliant creator.’ And so I think in some ways that may have clouded my judgment or made it difficult to see the right next opportunity, because there were a lot of people saying like, ‘Oh, you’ve got to take advantage of this, you’ve got to start a consulting company, you’ve got to start speaking at corporate gigs, and you got to do this and that and the other thing,’ all these things that were activities that had nothing to do with what got me there in the first place.

And so one of the reasons why I think why it took six years before I wrote my next book was I had to reconnect with this idea that okay, just because you had this one book that was successful, that doesn’t mean that people want to hear whatever you have to say about any topic that exists. You’re not just the smartest person in the world, you picked a topic that people were interested in and you had a good way of going about it. So if you don’t want to keep going forth with that topic, which I don’t want to keep going forth with that topic in the same way that I was before. I mean that’s how I ended up there was because I’m a dilettante, right, because I go from one thing to the next. So it took me a little while to reach back and say, ‘Okay, what are you curious about? What are the things that you struggle with? What can you spend an endless amount of time on?’

And so I think that was something that I guess it took another few years before I made that recognition that okay, I really love this experience of writing this book, of really getting deep into a topic and following my curiosity on that topic and trying to deconstruct it in some way that was interesting to people. And I love that activity and so let’s find a way to do more of that. And that was the moving to Colombia, in part because it’s cheaper here, and I knew it was going to take me a while to gain my footing, and I knew that I was going to have to sharpen my writing skills, that yes, I had written a book that did well, but I still had so much more to learn. I didn’t even understand books. Which is funny, because I had written a book and it had done well, but I still needed to learn so much about the book as a product and how to really be a good writer, something that I’ll probably never be done learning.

And so it was interesting that the success of that first product of following my curiosity I think for a while disconnected me from that curiosity, which was fine. It was fun, it was great to travel around the world and speak in different places. But eventually, I had to start saying ‘no’ to opportunities so I could reconnect with what got me there in the first place and see where it would take me again.

MARK: Yes. So it sounds like your curiosity about that particular subject was finite, but the deeper curiosity as a writer is what’s ongoing, continuing.

What motivates you as a writer now? What do you want to achieve with your writing?

DAVID: Sure. I think what you said about my curiosity for the subject being finite I think is absolutely true because, yeah, I was obsessed with design. I was obsessed with typography. And so it was through that obsession that I was able to develop a framework or, a mental framework or worldview about that subject, such to the point that I was able to write a book about it. Now, the thing that happens when your brain operates that way is that once you’ve written the book, now you don’t care anymore. It’s like ‘Don’t ask me about this, I wrote the book. So read the book, I want to get on to something else.’

And so what drives me now as a writer is again, following the, I don’t know if you mean specifically like what is it that I’m curious about, or if it’s a more abstract thing. But I guess on the abstract level, it is the curiosity. It is the trying to connect with that curiosity. And following that and seeing what questions emerge and trying to answer those questions and then trying to digest that into something that I can then present to somebody else and say, ‘Oh, here’s what I’ve learned. This is the way that I think about this.’ Now as far as topics that I’m interested in, I guess this was borne a bit out of my experience of writing Design for Hackers and developing this framework of thinking about design, but then maybe sitting down with a student and the student just being in agony that, ‘I can picture this thing in my head but I can’t make it real.’ I’m like, ‘Well, I wrote the book, this the thing that you just follow this framework for understanding this thing and, it’ll…’

But no, it’s an emotional experience and it’s something that I’ve experienced myself, and so that’s something that I’m trying to tackle now is that I do believe that everybody has some kind of a creative gift inside of them and I’m somebody who came so close to not getting that thing out of me, to, came so close to living the wrong life, that I feel very strongly motivated to try to take what I’ve learned about that process and make it possible for other people.

Because I think this is one of the great crises that we are experiencing right now is that we are moving out of this modality of ‘follow these instructions, get this degree, do this job, everything is going to be fine’. We’ve got AI and automation coming that will make a lot of jobs or a lot of people’s skills obsolete. That might sound like a crisis, but it’s also an opportunity, and opportunity is for us to connect on a deeper level with our own humanity, with our own creativity and to bring those things out into the world. But, ‘Uh-oh, we don’t know how to do that because we’ve programmed it out of everybody.’ So how do we get that back, because we were all born curious, you know? You’ve never seen a child that wasn’t curious. We just have it programmed out of us. So how do we reconnect with that and find a way to get that stuff out of people?

MARK: And this is one of the big questions I see you addressing on your podcast, Love Your Work, where you’re coming up to about 150 people that you’ve interviewed now, isn’t it?

DAVID: Well, I’m getting close to 150 episodes. Maybe half of those were interviews.

MARK: Okay. Well that’s still a decent chunk!

DAVID: Yeah. Like I said about my process is I have the conversations with people, and meanwhile I’m writing articles, and so then every other episode is an article or an essay which tends to end up being about the same themes, about the things that I’m talking about with people.

MARK: And so you’ve interviewed entrepreneurs, authors, technical people, personal development experts…

DAVID: Dancers, a chef, yeah, all sorts of folks.

MARK: Right, right. It strikes me that these are the people who have the kind of skill set that we increasingly need in the 21st Century. These are not people who live by the instructions and color inside the lines.

Could you maybe share some of the big lessons that have come out of those conversations for you about what it takes to thrive in this new world?

DAVID: I think probably one of the most formative conversations I had was with Seth Godin. And that was in the midst of me struggling to write my second book, and in the midst of me getting rejection letters from publishers and in the midst of me writing proposals and spending time on that. And Seth said to me, ‘Hey, the way that you should do this is you’re going to have to be head of marketing of your book anyway. So you need to learn how to market a book and how do you do that? You do it by…’ he said write a book a week on Kindle, which seems like a lot but I get the idea.

And so that really lit a fire in me, and I think it took a few months for it to really sink it. But then when I finally did self-publish The Heart to Start, that was definitely in mind. And note, like it took six years to publish The Heart to Start, and then within that time frame after publishing The Heart to Start, or including The Heart to Start, I published two more books. So it took me six years to publish my second book. It took me six months from that time to then get to my fourth book. And that was really thanks to that conversation with Seth and him talking about how you can’t crave reassurance, but here I am talking to this person who I admire and I kind of want him to tell me that I’m great or I want him to like me, and he’s not going to do that.

And he even says himself like, ‘Reassurance doesn’t work because you need an infinite amount of it.’ And so it’s something that you can’t be looking for. So that was an extremely formative episode for me, and it really led to action. And Seth actually ended up endorsing The Heart to Start a couple of months ago, which was another huge step. But I think that that all started with talking to him on my podcast in the first place and him lighting that fire under me.

MARK: So endorsement is better than reassurance, huh?

DAVID: Yeah! I don’t know. Maybe that’s a little ironic that he endorsed my book when he didn’t want to give reassurance. But I guess I got the book out.

MARK: Yeah. I don’t think he was going to reassure you that hey, you’re going to succeed or whatever, but, maybe once you did it he was quite happy to give you the thumbs up.

DAVID: I mean, you gotta wonder how many people does he give advice to that never follow it.

MARK: Right. Any other particular episodes or insights that stand out for you on this theme of, well, how do we succeed in a world with no rules? Or where we’re making up the rules as we go along?

DAVID: Yeah. I think back to the first episode. Jason Fried, who is the CEO of Basecamp, very well known for being a contrarian thinker, and I loved him telling a story of how when he was a freelancer, he would do these long proposals, and I had done that before. You spend weeks making this 20 or 30-page proposal and then what happens, you don’t get the job. And so he was talking about how one day he decided like, ‘Oh, I’m just going to do one-page proposals.’ Like, ‘What if I do that?’ Because the thing that I’m doing wrong isn’t, I made a long proposal and I didn’t get the job, so, obviously, the long proposal isn’t helping.

So he started making these one-page proposals, he started getting jobs, and I think the switch that flipped for him, and that flipped for me and hopefully for a lot of my listeners as well, was that when he started getting these jobs he realized like, ‘Whoa, wait! So everybody does it this way, but they don’t actually have to do it that way, and in fact it might actually be hurting them? And so you can just do it the way that feels right to you? Well, if that’s true for this, then what else is there that I’m doing the way that people have told me to do, and there’s actually some better way that I could come up with that would feel right for me?’ So, yeah, that was another one that was really formative. I actually just recently had him back on the podcast to talk about his new book, It Doesn’t Have to Be Crazy at Work.

MARK: So question everything!

DAVID: Yeah. I think so and that’s something that I think that I have done a lot in my life, that I do question things, everything. But I don’t always have the confidence to even listen to that question. You have these things that they’re just floating in your head all the time that you think like, ‘Oh, why is it this way?’ But you have to be paying attention to really catch those things. And then you actually have to have the experience of going forth with it and having it go well a couple times to gain the confidence to keep doing it.

Now, unfortunately, or maybe, fortunately, it doesn’t always go well. Sometimes some things don’t work and so sometimes you learn that that’s not the worst thing in the world too, to try something that doesn’t work.

MARK: So is this what you mean by ‘The Voice’ in the book?

DAVID: Yeah, exactly. There’s a chapter in the book called ‘The Voice,’ and it is about that voice in your head, it’s the voice that Steve Jobs was giving voice to for me when I first started out on my own. It’s that feeling that something that you’re consuming, whether it is a song or it’s a book or it’s even a painting, is just giving voice to something that you have experienced or thought yourself before, but that you didn’t put into words. This is why comedians work. This is how comedians work is that comedian says something and you’re like, ‘Oh, that’s so true. I’ve just never been able to put that into words.’ And you see it on a YouTube comment on a song, somebody says, ‘Oh, this is exactly how I feel.’ And they’re putting it into words.

Now, the thing is that if you are too late in giving voice to the voice and in taking those words that are in your head and putting them into some creative work, if you’re too late with that, then it’s a little too late. The work doesn’t have impact. But if you have the courage to stay connected with that and to continue to put those words into creative works of all forms, then I think that that’s where you end up with something that really resonates with people.

MARK: So we should listen in a little more?

DAVID: Yes. And this is something that I am constantly reminding myself of is that I’m constantly having these thoughts that for whatever reason I am afraid to follow. And so I have to remind myself about what I wrote. It’s a little bit Motivational Judo, if you will, that’s actually the phenomenon of cognitive dissonance, right, is that you want to be consistent, so when you write something…

MARK: Right!

DAVID: … that makes you want to be consistent with that thing!

MARK: That’s one of the humbling things about being a writer who’s giving any kind of teaching or advice is just that well, hang on a minute, I can think of plenty of situations where I thought, ‘Well, how can I look my readers in the eye on a Monday morning if I chicken out here?’

DAVID: Yes.

MARK: If I sit around the office procrastinating instead of writing, then what does my book on productivity mean?

I do think there’s something about committing on the page, it helps you to commit in real life.

DAVID: Yeah, absolutely. I find that happening with me over and over again. So that’s something that I experience with The Voice, is that I have thoughts in my head and it’s not necessarily that I have to make it into some sort of shippable product, I have to at least like take the time to jot it down and let it percolate, let it incubate. See if it ends up connecting with some other things later on down the road to create some new impactful thing that I never could have possibly foreseen.

MARK: David, thank you. You’ve really taken us on a fascinating mental and geographical and entrepreneurial journey with the accounts of your various adventures and writings. So I think maybe now it’s time to put the focus on the listener and give her or him something to do that is on theme from this conversation.

So what’s your Creative Challenge, David?

DAVID: This is very relevant to what we were just talking about with The Voice is that I find that one of the times when I have the most interesting thoughts is before I’ve even opened up my eyes in the morning. This is consistent with what we know about creativity, that people tend to be more creative in the mornings where they might still be a little bit groggy. And so what I do is next to my bedside I keep a little device called an Alphasmart Neo, which is basically just a keyboard with a cheap LCD screen on it. Costs about 50 bucks on Amazon used, they don’t make them anymore. And so I grab that, I still have an eye mask on because I sleep with an eye mask, and my eyes are still closed, I grab that and I say, ‘Okay, I have to write at least 100 words every morning before I even open up my eyes.’

Now, my challenge for listeners is to do the same thing. You don’t have to get this device. If you are a decent touch typer, meaning that you can type without looking at the keyboard to some extent, you can just keep a computer keyboard next to your bed, and before you wake up, just one morning, try this, before you wake up, grab that keyboard, put your fingers on the home keys, you can feel the little nubs on there, and just type everything that comes to mind.

Because you’ll find that it doesn’t actually have to be recorded. It’s just that you’re exercising those thoughts in your brain. You are strengthening those connections. You aren’t necessarily coming up with some sort of creative product in the moment, but you’re creating connections that will guide and frame your thinking throughout your day and throughout your work at all times. It’s a little bit like the Julia Cameron morning pages, except for in this case, you aren’t necessarily recording what you’re writing, and you haven’t even gotten out of bed yet.

MARK: I’ve heard of people writing before they’ve had their coffee, which I always thought was pretty extreme, but I’ve never heard of anybody writing before they opened their eyes!

How does this device work? I’m curious. How do you know what you’re typing?

DAVID: Well, I don’t necessarily know. I have an idea. For me, what’s important is the exercising of the synapses of the thoughts in my brain. And actually, when I’m done, I delete it.

MARK: So it’s a bit like the Buddha Board where the idea is to be in the moment…

DAVID: Yeah.

MARK: Making it, rather than to create some timeless artefact.

DAVID: Yeah, you’re in the moment and your brain is always working on your creative problems that you’re working on. So you prime your brain with these thoughts. You can delete the thing. But you find that these things resurface during other times. And so that’s what I find very useful, and part of it is that it’s just permission to… doesn’t matter how strange the thought is, you can write it, and you don’t have to be afraid. And sometimes you actually find something there that’s really nice.

MARK: David, I think you’ve won the prize for the most off-the-wall Creative Challenge! We’ve had a few, so, thank you. I love that!

DAVID: I hope you try it.

MARK: I might try it. So, I just have to get a quiet keyboard so I don’t wake my wife up! So David, thank you very much. I mean this has been a real pleasure talking to you. So you have your podcast, Love Your Work. Obviously, there’s the book, The Heart to Start.

Where should people go for all things David?

DAVID: The place to go for all things David would be Kadavy.net. I’m really active on Twitter at @kadavy and, of course, the podcast that you mentioned, which you will be on I believe sometime in early 2019. So go check out that interview because that was a great conversation as well. So thank you so much for having me on.

MARK: Pleasure, pleasure. And that’s Kadavy K-A-D-A-V-Y.

DAVID: Sure.

MARK: And obviously we’ll put all the links in the show notes as usual. So thank you once again, David.

DAVID: Thank you.

About The 21st Century Creative podcast

Each episode of The 21st Century Creative podcast features an interview with an outstanding creator in the arts or creative industries.

At the end of the interview, I ask my guest to set you a Creative Challenge that will help you put the ideas from the interview in to practice in your own work.

And in the first part of the show, I share insights and practical guidance based on my 21+ years experience of coaching creatives like you.

Make sure you receive every episode of The 21st Century Creative by subscribing to the show in iTunes.