David Kadavy On Unleashing Your Creative Genius [Podcast Ep. #23]

September 29, 2020

by Ravi Raman

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David Kadavy joins me on this episode. David is an independent writer, blogger, and podcaster. He has written several books, including the best-selling “Design for Hackers”, “The Heart to Start” and the soon to be released “Mind Management (Not Time Management)”.

In this conversation, we explore David’s career journey and intuitive call to step off a promising career track in Silicon Valley to become an independent creator, the nature of creativity, and why it matters that we unleash more of our full potential as artists. We also explore a few strategies for doing more great creative work that are relevant for everyone, even if you don’t consider creativity a vital aspect of your job.

Follow David on Twitter and at https://kadavy.net

Get “Mind Management (Not Time Management)”, David’s latest book, here.

Watch A Video Of This Interview

Full Transcript


Ravi Raman (00:19):
Hello, I’m Ravi Raman. Welcome to the Motivated Life podcast. On today’s episode, I bring you David Kadavy. David’s someone who I’ve been following for well over 10 years. Back in the days when blogs were cool, I subscribed to his blog, kadavy.net and used to read it regularly. I was fascinated by his various interests, his journey into self-publishing, which at the time was relatively new, his success in self-publishing and also his thoughts on psychology, creativity, and lifestyle design. I was also fascinated by his decision to, several years ago, four or five years ago, work from Medellín, Columbia and be in some ways a digital known man, but actually just make his home a place that he enjoyed and find a way to make a living from there.

Ravi Raman (01:17):
David’s a very transparent guy. If you read his blog, he shares his monthly income reports. So you can understand how he makes a living and what that’s like. On this podcast, we explore a few things. We explore his life journey and the insights that led him to lead what was a promising potential career in Silicon Valley, as a designer, having both coding experience and design experience back in the arts, the mid 2000s in Silicon Valley. He had a number of potential opportunities to join leading companies at the time. But he decided to take a path less traveled that to him just felt right. For me, I’m always fascinated by what it is that leads people to follow a calling and take their lives in a direction that is not necessarily the linear or logical path but is right for them. So we talk about that.

Ravi Raman (02:18):
We also talk about creativity. David’s written several books. They’ve sold well, and they’ve been self-published. One of his books, The Heart To Start is all about how to be more creative and to bring one’s art into the world. He also has a new book coming up called Mind Management, Not Time Management. It will be available… Well, you could preorder it now as I have on Amazon, and it will be published just within a few weeks. So by the time many of you listen to this episode, you’ll be able to get it or at least preorder it on Amazon.

Ravi Raman (02:55):
So we explore creativity, time management, and what it means for anyone to bring their creativity into the world, whether you are an independent creator or if you’re a middle manager in a tech company just looking to be more innovative. We discuss how to make that happen and why it matters that you make that happen. So I hope you enjoy this episode. Of course, it would mean a lot to me if you would share this episode with people in your network that you think would be benefited by it, and it’s always helpful to leave a review wherever you’re listening to this episode. It’s through your reviews that people are able to discover and find the various interviews and insights that I’m sharing. With that, I bring you David Kadavy. David, thanks for joining me.

David Kadavy (03:49):
Ravi, thank you for having me. It’s an honor to be here.

Ravi Raman (03:52):
It’s not often I thank social media. But I’m going to thank social media. I’m going to thank Twitter right now because I’ve been following your work for a long time. I’m losing track of time now, but sometime in the mid 2000s, I stumbled upon kadavy.net.

David Kadavy (04:07):
The 00s.

Ravi Raman (04:09):
Yeah. The 00s. That’s right.

David Kadavy (04:10):

Ravi Raman (04:15):
Kadavy. Good. So I stumbled upon your blog, and I started reading your blog and then you had this book, Designed for Hackers. I wasn’t a designer, but I worked in tech. So I got that. I was like, “Oh, this is pretty cool.” Then kept following some of your passive income stuff and then your move, which we’ll get into. But then I got back on Twitter recently, and I realized perhaps the most important use of Twitter, which is to actually make real connections. I started following some of your tweets and some of what you’re putting out, and I thought, “Wow, wouldn’t it be great to bring David on and just explore some of the things that you’re about that we’ll get into, creativity and more?” So thank you, Twitter for helping us actually connect.

David Kadavy (05:03):
Yes. Thank you, Twitter. Twitter is really wonderful if you use it the right way.

Ravi Raman (05:09):
Yeah. Your journey, maybe you can paint the arc for me because my memory tells me you’re someone who started working in the Heartland in a cubicle, found your way somehow into Silicon Valley and then took a leap and moved to South America, where you’ve been for a while. It’s pretty interesting journey. Why don’t you start by just connecting the dots for us on how you got from point A to Z?

David Kadavy (05:37):
Yeah. There’s an interim in there, even that. So I did grow up in Nebraska, Omaha, and I never really felt like I fit in there. It’s kind of hard to describe what that was like pre-internet. You can’t even go see indie movie really. I think it’s probably you could live in Nebraska now and it would be fine. The world is so connected. But that was where I grew up. I didn’t really have good examples around me that confirmed or affirmed the ideas that I had in my head. I was very curious, and I just didn’t really feel that that environment supported that necessarily.

David Kadavy (06:28):
So after college, I did end up going and working in a great cubicle for a few years at an architecture firm, and during that time, I decided to start a blog. I was reading all this blogs. I was reading Seth Godin’s blog. I was reading various web design blogs. One day I finally said, “Yeah. I’m going to do this.” I opened a blogger.com, and I started a blog. You can still see the first post. It’s terrible to run on paragraph. It has a misspelling in it. Within roughly a year or so, that blog helped me land a job in Silicon Valley. So I moved out to Silicon Valley, the Bay Area. I worked at startups for a couple of years. I spent a year working on my own startup.

David Kadavy (07:17):
About 2008, I decided to leave the Valley. I came to realize that while I had learned a lot from the Valley about how to believe in my ideas, get that confidence that I didn’t really get growing up in Nebraska and being somebody with strange interests. While I realized that it had helped me with that, I also realized, well, I was paying really high rent for basically access to venture capital and access to talent. These were two things I realized I didn’t need at all. So I moved to Chicago, and I rented a two bedroom apartment for the price that I was paying for one bedroom in an apartment that I was sharing with a bunch of other people in San Francisco.

David Kadavy (08:03):
I really just felt like I had something to offer. I had some ideas in my head. I didn’t know what they were. But I wanted to give myself the chance to cut out the noise and to explore what that was. After about three years of that, I got an email from a publisher asking me if I’d like to write a book. I had never-

Ravi Raman (08:28):
How does that happen?

David Kadavy (08:30):
Well, I had-

Ravi Raman (08:31):
Is this just the blog. Were you sort of hustling on the side to make connections and make it happen?

David Kadavy (08:37):
Well, I had written some blog posts that were popular on the topic of design. Basically, I was trying to get… What I was trying to do was get a talk at South by Southwest. I wanted to go do a talk at South by Southwest. So I engineered this long blog post with a lot of detail in it to try to get votes from my panel and became number one on Hacker News, this news aggregator website. I didn’t get the South by Southwest panel, but then I got this email for the book deal. Then by getting that book deal, I did end up doing a talk at South by Southwest.

David Kadavy (09:16):
So yeah. I get this email asking me if I’d like to write a book, and I’ve been blogging for six years at this point off and on sporadically. I’ve written a couple of blog posts here and there. They’re 2000 words long or so. But I’m not a writer. That was not a thing that I ever thought of myself as. I specifically hated writing as a child. Growing up in school, I liked to draw. I was an artist. But I did decide to take on the challenge and write this book, and I did that. The book did very well, top 20 on all of Amazon, and I started getting flown all over the world to speak. I spoke in-

Ravi Raman (10:00):
This is Designed for Hackers.

David Kadavy (10:02):
Designed for Hackers. Yes. I got flown all over the world to speak. I spoke in eight countries. In that process, I ended up traveling to South America, to Latin America. I liked the culture a lot. I then just kept coming back during the winters, after the winter that I spent writing Designed for Hackers. I never spent another winter in Chicago again. Eventually, I decided, “Well, I want to do this again.” I liked this process of being curious about something, learning a lot about it, trying to teach somebody else about it through writing a book. I said, “Well, I want to do that again. I want to double down on this writing thing. How am I going to do that?”

David Kadavy (10:55):
Well, one thing I wanted to do was reduce my expenses. Another thing was I just happened to notice during these winter trips that I took to South America, I was looking at the work that I was doing during those trips, and it was like, “This is my best writing.” I don’t know why, but let’s go figure it out. So I once again sold everything that I owned, which is what I did when I moved away from Silicon Valley and moved down here. That was about five years ago, and here I am sitting in Medellín, Columbia in an apartment with furniture that I own. I did spend four years in a furnished apartment just to try to clear as many distractions that it could for my life.

Ravi Raman (11:47):
I’ve seen photos of your desk. I don’t know if it’s still as sparse as some of the photos you’ve shared, which is basically a laptop.

David Kadavy (11:54):
Yeah. Well-

Ravi Raman (11:55):
This looks like the most sparse desk you can imagine.

David Kadavy (11:57):
It’s a more complicated setup now, and I actually have several different setups that I kind of switched between based upon the type of writing or work or thinking that I want to do. That’s part of what I’ve been doing down here last several years is really experimenting with how to make creative work happen. Because one of the things I discovered writing that first book was that everything that I had learned about productivity up until that point, I had been a productivity enthusiast, I was into getting things done, I was into time management, I was always talking with my colleagues about, oh, how I’m going to get [crosstalk 00:12:34]-

Ravi Raman (12:34):
You created a time management app, right? You created a app around time management and calendaring, right? I mean, that-

David Kadavy (12:42):

Ravi Raman (12:42):
So you’re not just a productivity geek. I mean, you went a bit off the deep end.

David Kadavy (12:47):
Well, what happened there was after the smoke cleared from the process of writing that first book, six months, it was actually a really dark time in my life, a winter in Chicago locked in my apartment by myself with a tight deadline, finish this book, hit these deadlines, or give back the money that they sent and tell all your readers and friends and family that you failed basically.

David Kadavy (13:22):
But once I finally got through that process, I started to look back on it and realized that I had kind of developed these ways of making creative work happen. A lot of the time I… The beginning, I was just banging my head against the wall 12 hours a day, trying to get this 15-minute window, where suddenly all great writing would come. So I wrote a blog post called Mind Management, Not Time Management, basically about manage your creative energy, instead of managing your time.

David Kadavy (13:59):
There’s a great behavioral scientist named Dan Ariely, author of Predictably Irrational, has done a lot of tremendous work in behavioral science, and he saw this blog post somehow. He reached out to me and asked me if I wanted to help with the design of this productivity app that he was working on called Timeful. I said, “Well, I’m not moving back to Silicon Valley, but I can work with you remotely.” We basically arranged for me to be a design advisor, worked with the design team, experiment with the app that they were building and experiment with the intersection of that app and my mind management philosophy that I was working on.

David Kadavy (14:46):
So we worked on that, and then Google ended up buying that app, Timeful. So some of those features from Timeful are now in Google Calendar. So it’s a pretty cool thing that this stuff that I learned writing the book, writing this Mind Management, Not Time Management blog posts, some elements of that are in Google Calendar now being used by millions, maybe hundreds of millions of people.

Ravi Raman (15:17):
I mean, who would have thought that the decision to start a blog and just start writing, I mean, would have… I suppose that’s just part of the way the world works. It’s very hard to connect the dots looking forward.

David Kadavy (15:29):
Yeah. Exactly. I was just going to say, like you said, connecting the dots, right? You can’t foresee that things are going to work out the way they do.

Ravi Raman (15:38):
So I want to actually wind it back a little bit. Before we talk about creativity and mind, time management, I’m curious about that Silicon Valley experience because I spent my career in tech, I left the corporate experience to go forge my own path. I worked with lots of clients in transition who are considering making a move. I would imagine someone with design skills back in mid 2000s.

David Kadavy (16:04):

Ravi Raman (16:05):
2008. Okay. So even if it was during the financial issues, I mean, there was-

David Kadavy (16:13):
It was right before it.

Ravi Raman (16:13):
Oh, right before. Okay. I would imagine that you could have had opportunities at a number of companies. What was it that gave you the insight that you wanted to do your own thing, and what was that like to make that choice? Because you’re saying no to what everyone else was doing in the Bay Area.

David Kadavy (16:34):
Exactly. I mean, I had tremendous opportunity in front of me. Imagine design skills, coding skills, startup experience, I’m in Silicon Valley, it’s 2007, 2008, and I leave. Crazy. Even as I was going through it, I’m thinking, “This is nuts. Why am I doing this?” But there was at least one startup CEO who literally begging me, “Please come work for us. I got contacted by a Facebook recruiter.” There was plenty of opportunities right there for me. But I just wasn’t interested in any of them. I had already been through working for one social startup, which was a green social network. Then I tried to build my own startup, another social startup.

David Kadavy (17:35):
One of the things I was realizing was, “Hey, this isn’t a very good model.” As far as like, it’s not really a good way to make money doing this. The things that we’re trying to do are good. That was one of the exciting about being in Silicon Valley and arriving in 2005 was that was the revival. That was Web 2.0. That was, “Oh, wow. Look, we can connect people using technology basically to have parties to tell your friends which bar or restaurant you’re at right now so they can drop by and say hello.” We were very optimistic about that, all of us.

David Kadavy (18:15):
But after kind of being through that, one, trying to do it to try to have a good impact on the world, and second, try to have a good impact on the world, but also try to figure out how to make money doing it. I kind of came to the realization like, “This isn’t going to work.” Along with it was also programming, cultural programming. There was the cultural programming that I had driven into me living in Nebraska that you got to have a job, and you want to have health insurance, and you like a more fiscally conservative way of life, and I was rejecting that, and I went to work in Silicon Valley, and then I came to realize that I was being programmed by Silicon Valley too, this idea that, “Oh, you’ve got to raise VC money, and then you’ve got to hire a bunch of staff, and you’ve got to get them all in a room and move fast and break things and all that stuff.”

David Kadavy (19:20):
Like I said, it was great in that it helped me believe in myself and believe in my ideas in ways that I never could have if I had stayed in Nebraska because I just didn’t have that influence. But once I gained that confidence, I came to realize, “Well, the goal that I’m going for isn’t actually the goal that I want. The goal that I want is I want to go into this curiosity and see what’s there.” Now that I had the confidence, and now that I had some idea how to do something, how to make something out of nothing, then I just wanted to get out of the noise. I just wanted to get out of the hype.

David Kadavy (20:02):
I mean, this was the height of… This was before Silicon Valley became a bad word, right? These are the days when Theranos was trying to be like Apple and work in the media to do this kind of Hollywoodish thing. This is before the scales fell off the eyes of the public.

Ravi Raman (20:27):
Right. I mean, what I’m hearing in you is you had some clarity on wanting to move things in a different direction. What I’m fascinated with is, where’s that clarity coming from? Were you inspired by a talk? I get the sense that from your roots in Nebraska, you saw where it was going, and you wanted to follow your curiosity.

David Kadavy (20:51):
Well, I wasn’t totally confident in. I mean, narrative fallacy, I can look back on it now and say I made the right decision, or maybe that’s also reverse rationalization for [inaudible 00:21:02] as well. At the time, it was just a gut feeling. I felt it in my bones that I wasn’t going to be able to get what I wanted out of being in Silicon Valley. Now that you mentioned a talk, you probably know this, is that I did sit and watch the Steve Jobs Stanford commencement address over and over again, where he’s talking about connecting the dots. He’s talking about following your curiosity. He’s talking about having the faith, that it’s all going to work out in the end.

David Kadavy (21:37):
I guess maybe that’s the part of Steve Jobs if I can use him as sort of a symbol of what caused things to go wrong in Silicon Valley, in some ways. That’s the part that I think maybe a lot of people missed was this message of really dig deep into your strange, weird ideas, especially if it doesn’t make any sense to you why you’re doing it, especially if it’s not clear where it’s going to lead and follow that and see where it takes you. So that was something that I felt in me that made me do this thing that all the while I was like, “Wow, I can’t believe I’m doing this.”

David Kadavy (22:34):
Part of it also, I think, and maybe this is part of what makes it difficult for maybe some of your clients or other people in Silicon Valley was remember, I grew up in Nebraska. I statistically should be selling used cars or mowing lawns, or at best, sitting in a gray cubicle at an insurance company doing some middle management job, at best. So when I was in Silicon Valley, and suddenly, I was surrounded by these people who from the day they were born, they were going to go to an Ivy League university and their parents expect them to be doctors and lawyers or do investment banking, and they’re shaming their family by working at startups, basically.

David Kadavy (23:31):
To be around those people who had maybe that kind of pressure, I didn’t have that. I wasn’t really supposed to be in Silicon Valley in the first place. It was kind of a chance thing. I wanted to get out of Nebraska, but I wanted to go to Chicago or Minneapolis and work at a design firm or an advertising firm or something. Somehow, I ended up working at startups in Silicon Valley, which was a fantastic experience and wonderful.

Ravi Raman (23:57):
Right. But you didn’t have a… What I’m hearing is you didn’t have the pressure since day one that, yeah, we’re supposed to be a certain way, and you were able to navigate a more malleable path for yourself.

David Kadavy (24:10):
Yeah. I didn’t have as much… I mean, certainly, there was my family being like, what are you doing? When are you going to go get a job?

Ravi Raman (24:22):
Are they still asking you that?

David Kadavy (24:24):
No. No. There was that. But I realized at that point, I had recognized that the constructed reality of the collective consciousness in a place such as anywhere, but I could at least see the matrix in Nebraska or the parameters of that thinking and see that people had constructed their own reality about what was true and what was right and that if I felt differently, then I should go with that. Because there were so many things where when I was in Nebraska, especially as a young professional, I remember my boss coming to my desk almost every day and asking me two questions. When are you going to get married? When are you going to buy a house? Why would he want that? Because then I would be more beholden. It would be harder for me to get away.

David Kadavy (25:37):
I’m thinking, “I’m 23 years old, and my friends around me are buying it.” They’re drinking the Kool-Aid. They’re saying, “Buying a house is the best investment you can make since 2003, 2002, 2004. Buying a house is the best investment you can make.” In my head, I was saying to myself, “That’s ridiculous.” I’m 23 years old. If I buy a house, if I ever want to move, I have to sell the house. The best investment I can make is in myself. Now, I wish I would have had the confidence to write that on my blog at the time years before Choose Yourself by James Altucher. But once I did get out of that matrix and did go to a place like Silicon Valley where people valued my ideas, where if I had a weird idea, people be like, “Oh, yeah.” Well, get to actually watch your mouth, what ideas you come up with because people will make you do it, or at least they would then.

David Kadavy (26:41):
So after seeing that, after seeing the way that the matrix, the cultural matrix, the water that we as fish all live in, after being outside of that, enough, I got better, I think, at being able to separate reality from constructed reality. Or I mean, it should be a little more modest than that. I mean, I’m sure that there’s all sorts of things that I take as reality that aren’t really reality. But you know what I mean, I think.

Ravi Raman (27:13):
I absolutely do. In my work with leaders, a core conversation is how we’re all living in a movie of the mind. We’re living in a creation based on our psychology. There’s incredible both peace of mind and actually potential that comes from having a new relationship, where we’re not just stuck in the structures of our mental story but more connected with whatever is really going on. Right? So I absolutely understand what you’re saying and what you’re pointing to.

Ravi Raman (27:47):
So from there, you were able to carve a path, and you’re in Medellín, Columbia, and you’ve written a few books, Designed for Hackers. You’ve written The Heart To Start, Win the Inner War & Let Your Art Shine. [crosstalk 00:28:05]-

David Kadavy (28:04):
Now, it’s called Stop Procrastinating & Start Creating. I always give you-

Ravi Raman (28:10):
Oh, is it?

David Kadavy (28:10):
… some permission to change things halfway through. Yeah.

Ravi Raman (28:12):
Okay. Great. Great. So you’re adjusting the title. That’s great. And self-published, right?

David Kadavy (28:16):
Self-published. Yeah.

Ravi Raman (28:17):
Okay. And you have a new book coming out, Mind Management, Not Time Management.

David Kadavy (28:23):

Ravi Raman (28:24):
Right. So what I want to transition, just talk a little bit about is, let’s start with creativity, because for me, it seems like just getting started is the hardest part, which is why your book is so interesting. It talks to a lot of ways to get over that initial procrastination or starting point. But it does beg the question, why does it matter that people are creative? I mean, do people have creative genius? Is it even important? I mean, are you writing this book for everyone? Do you think everyone should unleash their creative genius, or do you think… I mean, I’m curious what you think. Does everyone have some potential waiting to be unleashed?

David Kadavy (29:04):
I think that everybody does. I think that almost all of us have this feeling at some point, and maybe it’s been pounded out of us by the time we’re adults that I had something to offer. There’s something that I could contribute to the world that would be an expression of my curiosities, of my interests, of my passions, and that would have some use to other people. So I think that we all have that. Now, why be creative? I mean, if you want to come up with a more logical reason, I would say that the coming of AI and automation, we’ve been living in this world where humans are turned into interchangeable parts to do certain jobs, and you can change out this regional manager of operations and then replace that person with a different regional manager of operations, and they’ve got the same education, and the world isn’t that way, or it’s becoming less and less that way.

David Kadavy (30:17):
If it can be done step by step, then there’s not really much point in doing it, because a computer can do it. So being productive or being useful in this world isn’t about like, “Oh, I can type faster.” Or, “I can type 50,000 words to make a novel faster.” It’s like, “Well, can you come up with the great idea? It doesn’t really take any time to have that idea.” So I do think that we are transitioning into an age where this is becoming more and more important for us to find what [inaudible 00:30:51] calls specific knowledge, this thing that only you can do it. You’re the best in the world, not a one thing, but your combination of things. I think that we’re entering that time right now, and we need to figure out how to make that transition.

Ravi Raman (31:13):
Even amongst my peer group and people I’m working with, the conversation tends not to be, how can I be more productive? It tends to be, how can I innovate better? How can I help my team innovate better? How can I solve a problem that we haven’t solved before? How can I think differently? So perhaps we’re maybe on the cusp of a new wave of conversation about creativity and effectiveness versus, let’s just be more productive, which I know in the ’90s and the 2000s, there’s book after book, after book. So I’m right there with you. I’ve never considered myself a creative, but here I am doing a podcast, and I have a blog. So I’m with you.

Ravi Raman (31:56):
So let’s talk a bit about what it takes to have someone if we assume that we’ve got creative genius inside for a second. What does it take to unleash that? Now, I know this is a whole book. But what are some of the key things that you think someone listening who might be running an engineering team or running a marketing team, what do you think would help them unleash more of their creative potential?

David Kadavy (32:24):
I think probably the first thing is getting comfortable with there being kind of gray areas. I think that we’re living in a mechanical world. We’re moving from the mechanical world to an automated world. That’s something that Marshall McLuhan talks about his book, Understanding Media. It’s from 50 years ago. It sounds like it’s from the future. He talks about civilization being mechanized and how automation makes civilization more organic. So one of the things you have to be comfortable with then in that process is things being not quite so binary. It’s not, “Oh, I can’t write. I’m not a writer. I can’t program. I’m not a programmer.” It used to be, you’re not these things, unless you have secured a job doing these things.

David Kadavy (33:28):
Instead, there’s a spectrum that you are dabbling, and you’re doing a little bit of programming. You’re doing a little bit of writing. In that process also, your projects aren’t… It’s not necessarily start, finish. It’s not necessarily not done, done. There’s areas in between there. So when you give yourself permission to have a place where you explore your ideas and where you manage your ideas, and when you give yourself permission to do little tiny projects before you get to the big vision that you have, then you start to actually make a little bit of progress. Now, where to find the ideas. How do you be innovative?

Ravi Raman (34:20):
Can I ask you?

David Kadavy (34:21):
Yeah. Sure.

Ravi Raman (34:22):
Before we go there, curious for you. So you’re a writer.

David Kadavy (34:24):

Ravi Raman (34:24):
I mean, I had this vision of, you’re toiling away at your little keyboard. I recall you have some special device that you use to keep your mind focused. But you’re toiling away at your keyboard. But my guess is you have some interests that have inspired you and informed your work, I’m guessing. I mean, in the same way my yoga and meditation practice and my love of technology have come together to inform how I approach my work, do you feel like there is… What are the other interests in your world that are informing your vision for how you’re writing your work? Is there anything, or is that not-

David Kadavy (35:03):
I mean, it’s just limitless, really. I mean, everything is fascinating to me. So I do a Latin dance. I used to play golf a lot. Haven’t been playing a lot lately. I used to love to lift weights and learn about fitness. I read books on all sorts of different topics. There’s really no limit to it. I guess it’s really just wanting to understand the world. Like you talked about meditation or yoga practice, I meditate regularly. I’m trying to do an hour a day right now and trying to separate my perception of reality from reality is a big thing.

David Kadavy (36:00):
So I think part of that process is learning about behavior and learning about psychology. Psychology, I guess, would be a thing that really interests me. It’s kind of a selfish interest because I want to make it as a creative. I want to find my specific knowledge, my thing that I can do and share with the world. That’s an ongoing process. I’ve obviously written some books and each one is hopefully a little better than the previous one, and some future ones will hopefully be better as well. But it’s an ongoing process to do that. So yeah. But that’s a-

Ravi Raman (36:54):
You seem to have an innate curiosity. I mean, I’m hearing you’ve got an interest in psychology, an interest in perception and a curiosity that’s been with you.

David Kadavy (37:05):
Yeah. Let me pick up, I lost my train of thought earlier. So I am trying to share this thing that I believe that I have with the world, and hopefully, some people will find it useful. But I realized that in that process, you’re in a house of mirrors, right? There’s all these distortions going on. When you’re trying to discover who you are and to share that with the world, there’s all sorts of mental distortions. Now, we all experienced different weird psychological quirks and biases, and it’s hard to see those things in normal everyday life.

David Kadavy (37:54):
But when the stakes are that high, when the stakes are so high that it’s like I’m trying to figure out who I am and bring this into the world and make my avocation, my vocation, then the stakes are really high, then it becomes, okay, I really want to know if I’m fooling myself. I really want to, the ways that I’m lying to myself. I don’t want to know the ways I’m lying to myself because somebody can tell me I’m wrong about my political views or whatever. No. I want to know the ways that I’m wrong so that I can see myself as I really am and to hopefully make this thing happen.

David Kadavy (38:34):
So that’s something that does drive my work a lot, I think is trying to find some sense of the truth, trying to find the ways that I am fooling myself, the ways that I’m wasting my resources without being aware of it, the ways… Yeah. How can I be effective? How can I take my very limited resources and focus them in a way that helps me figure out this thing that is very hard.

Ravi Raman (39:12):
Right. Now, you’ve written, and as I’m listening to you, I hear a lot there that would be relevant for a lot of people. How can they see more objectively and clearly? How can they focus their energy on something that’s hard? We’ll talk a little bit about maybe some ways to look at it. One I want to just talk to you about is some of the things you’ve done. You’ve done a lot of experiments that you’ve blogged about and talked about that I think would be just interesting to get your perspective on why they’re important and maybe what they might do for others.

Ravi Raman (39:45):
One you’ve written about, why creatives need to live in extremist stand, sort of cribbing on Nassim Taleb extremistan versus mediocrestan. You shared a bit about what it was like to live in extremiststan. Can you just capture what you were trying to do with that experiment and why it matters that creatives live in extremistan? What is that, and why does it matter?

David Kadavy (40:10):
Yeah. This is something I’ve come to realize. As you try to navigate the world, and you try to find information that’s useful for advice that’s useful for you to do the thing that you want to achieve is that, as Taleb talks about in The Black Swan, there’s two places. There’s mediocrestan and extremistan. Now, mediocrestan is the world that we’ve constructed with our civilization, right? I mean, this is one thing that I’m keenly aware of. I’m an animal that has lived live in this world, and I’m surrounded by things that were made up by people before me that make my life really great. There’s flush toilets and food that I can get, and I have health insurance.

David Kadavy (41:15):
So yeah. I’m making money. But if something bad happens with my health, and then it’s there to help with these sort of extreme events that happen in the course of living. That’s what civilization is, is let’s smooth out the risk in everyday life to make things just go more smoothly. So there’s kind of a safety net. In order to do that, there can be some volatility in the way… Obviously, we have natural disasters and weather changes, and things happen in the political world. Hopefully, we can withstand those shocks.

David Kadavy (41:58):
Take a company like Starbucks. Go get a job at Starbucks serving coffee. They’re going to pay you by the hour. How can they do that? That’s actually kind of amazing that they can do that. They can say, “Here’s a contract. Go to work, and I’m going to pay you this much every hour.” How can they do that? Because they have a bunch of data, and they pretty much know, what does coffee cost? What does it cost to run this location? How many customers are we going to have across all these, I don’t know if millions of locations? If we pay people this amount per hour, we’ll make a profit, and we won’t go out of business, and the whole thing won’t just come crumbling down like a house of cards. That’s actually pretty amazing.

David Kadavy (42:52):
Now, if you’re a creator, if you’re trying to be innovative, and this is something that you see a lot when people try to measure things in startup advice or business advice. It’s sort of like, “Well, what’s your run rate?” What is your monthly revenue? What is this idea of something that goes on and on and on in a steady way.” Yeah. Maybe there’s some ways to do that with creative work. But as Taleb talks about, the turkey, the black swan, you take a turkey, and you ask it, “Do you think that humans are good?” “Well, humans come and bring me food every single day. So humans are great. Then Thanksgiving comes along, and all of a sudden the humans aren’t so good.” [crosstalk 00:43:40]-

Ravi Raman (43:40):
I’m vegetarian, so I’m still for the turkey. But I get it.

David Kadavy (43:41):
There’s this event that comes along, and suddenly, everything changes. Now, that can have negative consequences. It can have positive consequences as well, where I can sit and look at the conversion rate on my website for how many people who come to my website sign up for my email list. Maybe if I work really hard, I can increase that by 10%, or I can try to write a blog post that’s based on a really new idea and maybe do some strategic things to kind of target it towards a certain group of people or whatever. All of a sudden, I get this huge traffic spike, and then I get a book deal, and then I’m speaking at South by Southwest, and then I’m getting flown all around the world.

David Kadavy (44:37):
It’s these explosions that happen. That’s how success really happens in innovation and creative work. It’s not, A, is this happening a little bit more than it was happening yesterday? It’s this explosive event. That’s extremist stand. That’s the world of black swans, of these sort of one-time events that you can’t foresee and that we also have a tendency to reverse rationalize. So even when I tell you how I [crosstalk 00:45:08]-

Ravi Raman (45:08):
Like your blog post. Yeah. Like your blog post.

David Kadavy (45:10):
It’s a narrative fallacy. You can’t actually engineer a black swan. As Taleb has said, this coronavirus pandemic is not a black swan. It was an inevitability. What the black swan is, is like, oh, we have insurance for the twin towers in case there’s a fire. What happens? Something completely different, that nobody, first of all, at all, that wasn’t in the contract for insurance or whatever. These events that just kind of happen. Well now, how do you make that happen then if it is unpredictable, if we tend to reverse rationalize these things and explain them away with the narrative fallacy in reverse, well, then what can you do to make extremist stand stuff happen? I’ll stop talking at the moment right now and let you chime in if you want.

Ravi Raman (46:11):
Well, it sounds like you’re speaking to an element of what people colloquially would say take risks, but it’s different than that. It’s that in some ways, mediocre stand is sort of risky because then it’s like the average. If you want to have an opportunity for something to happen, then these things that might seem like fringe is actually a way to be “extreme”, but actually open yourself up to chance. So playing with risk, playing with chance and understanding that creativity comes from that, playing in that world, which is different than say the Starbucks job or something.

David Kadavy (46:57):
I’m glad you mentioned risk. I do want to say also mediocrestan, it sounds derogatory, but it’d be great to live in a society where people could be mediocre and get by, I think. This isn’t what we’re talking about.

Ravi Raman (47:12):
Well, I like waking up and knowing I have a roof over my head and that my water is running

David Kadavy (47:21):
… there are things that government is supposed to do for us to help you have a safety net and all that, stuff like that’s all good. That’s not what we’re talking about. We’re talking about becoming great, right? We’re not talking about whether it’s fair or not to have to become great. We’re talking about becoming great, this is what we want, and risk. Risk has risk and is risky are two different things. So if something is risky, crossing the street is risky. It’s amazing how many cars come within feet or inches of us in our lifetime at speeds that could kill us without it happening. It’s risky. The downside, the potential downside of crossing the street is enormous. It’s everything. You could lose everything crossing the street. Has risk is different. Yes. Is it risky, or does it have risk to start a blog? Yes. You risk and likely will have nothing to show for it.

David Kadavy (48:36):
I can’t say likely will. Most people should start a blog probably. But you do risk investing a lot of time and energy and getting nothing out of it. You’ve risked something. Is it risky? Not really. There’s not a lot of horrible things that can happen because you started the blog or have much likelihood that they’re going to happen. So the way that Taleb about it again, and he doesn’t talk about it necessarily in the context of creative work. This is the way that I think about it is the barbell strategy is if you imagine a bar bell. One side of a bar bell has a weight. The other side has a weight. The middle is thin. That’s the bar that you hold onto.

David Kadavy (49:24):
So on one side, you’ve got your sure bets. For me, that’s passive revenue. It’s like every month, I kind of have some money coming in that I don’t really have to actively work to make happen. For some people-

Ravi Raman (49:35):
Through book sales and-

David Kadavy (49:38):
Through affiliate revenue, through book sales as well, but especially affiliate revenue. I kind of have a recurring revenue padding going, and people can see my income reports and see what I’m talking about of like, every month, I could just completely stop doing anything, and for a while, there would still be money coming in. Other people have different strategies for this. Somebody like I think Anthony Trollope, I can’t remember where… He might’ve worked at the bank or the post office. Lots of different writers have worked at the bank or the post office, and they’ve got that thing. That sure bet.

David Kadavy (50:15):
Then on the other side is the sort of black swan plays, these things that you can do that have unlimited upside, but very little downside, asymmetric opportunities, right? So if you’re investing, one side of the barbell is the… I’m not a financial advisor.

Ravi Raman (50:37):

David Kadavy (50:37):
I’ll say that. One side of the barbell is bonds or something safe. Other side of the barbell is cryptocurrency, Bitcoin, is things that maybe an angel investment, things like that. I said this on Twitter, and I know that Nassim Taleb says that not to talk about black swans as thinking of winning the lottery, because the lottery does have… You know the odds. But I’ve thought, well, if I could automatically buy a lottery ticket every month or every week, that would be one side of the barbell possibly, is that, yeah, it doesn’t. So well, it cost me a dollar a week at a certain level of income. That doesn’t matter. But there’s some small chance that you’ll have some huge upside thing.

David Kadavy (51:31):
Then it’s the barbell in the middle, and now, like I say, I’m not a financial advisor, but I’ve heard some people say, “Well, the old tried and true index fund that people think is so safe, well, maybe it’s not so safe because you can lose 30% in a year.” I guess they want to work out over time. But anyway, when it comes to creative work, then yeah, you have some sort of secure thing kind of making the bills paid, and then you have this other side where you’re just making these small bets, making small bets that are kind of crazy and weird, and they might have a huge upside or likely most of them nothing will happen.

Ravi Raman (52:13):
Just in our last few minutes, I want to bring in the fact that you’ve had a podcast, love your work for several years now. You’ve had several hundred episodes. Just if you were to capture, I know this could be hard to do, but if you were to capture the essence of, what are a few things you’ve learned in interviewing hundreds of people, I mean, Seth Godin? You’ve had a number of folks on your podcast. What have you learned through those interviews that’s really impacted your life and your work for the better?

David Kadavy (52:49):
I’ll try to just be really specific about it and say that I’ve learned a lot from Seth Godin personally on those interviews I’ve had with them. I’ve had two interviews with Seth Godin. The first one is kind of a big breakthrough because that is a time when I have decided that I’m going to double down on episode 77 on Love Your Work. It’s the time when I have decided I’m going to double down on writing, and that’s a period of time where I’m still trying to go the traditional publishing route. My first book was traditionally published. I was changing genres. I was struggling to work the traditional publishing route on a new book in a different genre and a different topic.

David Kadavy (53:40):
I kind of did jump through some of the hoops and trying to make that happen. I didn’t go through the 40 rejections or whatever that some people go through. I got in patient much quicker than that, and I was talking to Seth on the podcast and kind of waffling about that. He’s saying, what’s the holdup? You can’t see this authorities is to somebody else because they’re not going to do a good job. If you want to be a good author or writer, then you’re going to have to do the marketing for your book anyway. So why give away 85% of your income and right to a publishing house when you’re going to have to do the marketing anyway?

David Kadavy (54:34):
So what you should be doing is publishing and learning as you go and getting better and better and better at it. I can definitely track that back to that conversation. I mean, this is not narrative fallacy. I don’t think that that was what flipped the switch in me. It wasn’t too many weeks later that I finally did publish The Heart To Start. I guess it was a few months after that that I finally did publish The Heart To Start, self-published. Then actually, once I started doing that, I then published some short reads. I basically went six years between publishing my first book and my second book. But once I published my second book, I published three books within six months. I mean, a couple of them were short reads.

David Kadavy (55:24):
But that really just opened the flood gates, and I started really learning about publishing. I started really learning about books, and I started really learning that a lot of the ideas that we have about books, about what a book is and what a book should be like and what a book launch should be like and who should be an author and who shouldn’t and what does a bestseller mean and what is the bestseller not, I started to realize that a lot of these ideas that we have are actually quite old, and they’re left over from sort of economic mechanics that don’t exist anymore in the world books.

David Kadavy (56:04):
So now I’ve just not even… I don’t even attempt to traditionally publish at this point anymore. So I’ve got this next book coming out, my management, not time management, and it’s the biggest project I’ve ever had. I’m very excited to get it out there, and it’s coming out in a month, and I’m not going crazy because I don’t have a publisher breathing down my neck and trying to get me to kill myself with my launch or anything like that.

David Kadavy (56:36):
I guess I didn’t mention that my second conversation with Seth was after The Heart To Start had come out. Seth had endorsed the book on his blog, which was wonderful. That was when he was reminding me that nobody can predict what’s going to be a bestseller when it comes to books. If publishers knew what was going to be a bestseller, they would only publish the bestsellers. They wouldn’t publish thousands of books to only have a few of them be winners. So it’s always a surprise. It’s idiosyncratic. So you should do the weird thing that feels right for you. That was episode 177. I think that really helped me dig in to this Mind Management, Not Time Management book.

Ravi Raman (57:36):
I suppose that gives us a leg up against the AI machines. If things are less formulaic, if they are more black swan oriented, we’ve got a shot. David-

David Kadavy (57:46):

Ravi Raman (57:47):
… I feel like we can have two or three more podcasts perhaps in a future month. We’ll-

David Kadavy (57:52):
[crosstalk 00:57:52]-

Ravi Raman (57:52):
… have you back on to explore mind management, time management in more detail. Everybody check out The Heart To Start, which is now called… What’s the new title.

David Kadavy (58:01):
Well, it’s called The Heart To Start: Stop Procrastinating, Start Creating, which is a subtitle.

Ravi Raman (58:06):
Got it. Gotcha.

David Kadavy (58:08):
Because it’s not a binary world. You can publish a book, and you can later on decide, you know what? I should have changed that part, and you change it.

Ravi Raman (58:17):
Gotcha. New book coming out shortly, Mind Management, Not Time Management. They could follow you on kadavy.net and Twitter.

David Kadavy (58:26):
Twitter @kadavy. I’m on Instagram as well, @kadavy, but Twitter is my true love.

Ravi Raman (58:31):
Wonderful. Well, thanks again, David. Take care.

David Kadavy (58:34):
Thank you!


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