Working systems - David Kadavy

00:00

... love your work is more of a mantra I tell myself every day, as I decide what I'm going to do, and that's how I've gone the path that I'm on, was after working enough jobs and feeling like, okay, I don't want to work for somebody else, I want to use as my main metric this feeling of being very curious about something, of losing track of time as I'm working on something, of, however, it was I felt when I was in my room alone by myself as a kid, playing with magnets or drawing or counting my change jar, or whatever that just, you forget to eat, the time's going by and you're hardly even paying attention. I've just tried to reconnect with that feeling. And so I'm getting close to 15 years now and I may have made it.

01:09

How do you think our mind gets in the way of us finding our best work?

01:16

For me, I had a lot of different cultural programming that created a lot of baggage around work. I grew up in Nebraska, in the middle of the US, and it was a very different time, or different place before the internet. You literally just only had access to whatever media was funneled to you, and then the people who were around you. And so growing up in a suburban place, everybody around me's got a middle management job at an insurance company or something like that. And there was this, just very instilled in me belief that it's very important to have a job. It doesn't necessarily matter what that job is, that you wouldn't expect to enjoy your work or your job. It's not something that you would mess around with after hours. Our upbringing, our cultural programming, the beliefs that we have, those are some big mental barriers to doing work that we're going to enjoy, that we're going to find fulfilling because we just don't have maybe an example, or somebody that we've met or talked to that we can model ourselves after.

02:47

How did you get over that barrier? How did you end up in Silicon Valley in that circumstance?

02:53

It was a very roundabout and lucky thing. Despite being in an upbringing, I still was always creative as a child. I spent so many hours in my room drawing, and that's what I wanted, I wanted to be an artist. What's the use of being an impressionist painter in the 21st century? I don't know, but that was my idea, but then there was this thing instilled to me like, well, you got to get a job. You're going to go to college and you're going to study something. It's got to be something that you can get a job with. And while I was lucky enough to have parents that weren't like, no, you're going to study business and that's it, it was still instilled in me like, you want to have a marketable skill. And so I picked commercial art at first, it was what it was called.

03:52

That's so funny. Just the slight tweak.

03:55

It was a commercial arts, it's art, but it's commercial. And it later became known graphic, or it was called visual communication design, or something, later became graphic design. I transferred colleges once I started to understand that profession and field and started to enjoy it and became very passionate about it. But it was just one little thing after another, where I was just scared out of my wits to take these steps that I didn't see other people taking. And not just because they were truly scary things, I just lacked confidence, I guess. I was very afraid to go two hours from my home to a college, or to transfer from one college to another in the middle of the year and not know anybody. I was so scared about that.

04:55

It sounds like you lacked perspective too, if you're in that bubble and it's then hard to see what that type of work exists outside of it.

05:04

Yeah. Yeah. And so, if I can make the long story short, I guess, went to college, did a study abroad in Rome, that opened up my eyes to the Pandora's box of all the different ways that there are, are there different ways of living, or seeing the world. And then ended up having to come back to Omaha and work for three years at a job there and made my blog in 2004, put up my design work, put some feelers out there and got discovered by a startup in Silicon Valley. And it was just a miracle to me to get out of Nebraska and move to California.

05:53

It's basically how much the infrastructure and your geography affects your work choice.

06:02

Oh, huge. Especially then, this was 25 years ago, or something. And I've got perspective on this. I live in Columbia now. I know how hard it is for a lot of people who are born here, who just don't have a lot of opportunities. But at the same time, being born in Nebraska, I was born in America. Okay. That was huge. It's like a huge ovarian lottery win, as my former neighbor, Warren Buffet, would call it. And, but at the same time, I remember living in San Jose. So San Jose was the first place I went to, and I was just like, I'm going to California. That's awesome. It turns out San Jose, I don't know. It sucks to live, or wasn't what I was looking, I had envisioned, or was looking for. I had a good first year there, I decided I was going to move to San Francisco.

06:55

San Francisco is what? An hour and a half train ride away, something like that. I figured I would just go ahead and do the horrible commute for a while until I found something else. But I remember going to move up there. And I remember talking to people who were San Jose natives, who were like, oh, wow. Yeah, you're moving to San Francisco. Gosh, I've thought maybe someday I might do that. What? You're an hour away. How could you not? And I'm sure that the, when an immigrant comes to the United States, they're probably looking at all the Americans thinking the same thing. What? How could you? This opportunity's right there. How could you not do something?

07:37

It's absolutely the same when Americans come to the UK and they say, well, you haven't been to Belgium? What's going on? It's so just over there, or you haven't been to Paris, it's like-.

07:47

Yeah, yeah.

07:48

Oh, no.

07:49

So definitely what I hear people say, I think it's all relative, I hear people say, oh, I grew up in Long Island, like it was some hardship that they lived an hour away from the cultural Mecca of the entire world, New York City. But I'm sure that people who aren't from the United States hear my story about growing up in Nebraska or whatever is like, oh, boo-hoo, born in America. But I was scared. I was scared to make changes and do things. But I just did it over and over again until I wasn't scared anymore, I guess.

08:27

Besides the physical nature that you were surrounded with, and the geography that was around you, the physical barriers that stopped you, finding that work, what barriers of the mind did you encounter finding your best work? And what barriers of the mind do you think people typically hit when they're trying to find their best work?

08:59

I think a big one is, should, what you feel like you should do. What the definition of success is. And I had seen enough where say, for example, growing up in Nebraska, there was a certain definition of success. If you go get the job at Mutual of Omaha, or such and such insurance company, and get your benefits and get a stable job for years and years and years, well, hey, you've got it made. And then I remember coming to Silicon Valley and seeing people who, they had gone to an Ivy League school, they had gone to Yale or Harvard or Stanford, places that when I met those people, I just thought to myself, wow, I've never met a person who's gone to one of those schools. That wasn't even presented to me as an option of a thing that you could do. I thought that, that was just for people in movies.

10:05

But at the same time, I could see how they still have this expectation on them, by their family, or their friends, or their social group, where they still had to, they felt they still needed to demonstrate some kind of success like, oh, they chose this startup route instead of being a doctor, or they chose this startup route instead of being in finance, or something like that. And, oh, are they going to disappoint their family? Things like that. And I think it was nice for me to be exposed to that because at some point I just decided, well, hey, I don't have to define my success by anything. I've got no pressure on me. Yeah, my family maybe had certain expectations for me. They weren't overbearing about it, but I didn't have the same pressure as say, those people did, yet I had this opportunity of being in Silicon Valley by accident, surrounded by these extremely motivated, talented people, rich people.

11:19

And so I wanted to make my own a definition of success out of that. But I had to, at the same time, wrestle with taking on some of their definitions of success for a while before I decided that maybe that wasn't for me. So for example, when I started on my own, one of the things I did, I built an app and talked about that I was going to raise money, and start having all these employees and get an office and all these things, but I never made one meeting with an investor.

12:00

And I think ultimately I just decided, oh, that's actually not what I want. I don't want to manage people. I want to just sit and be like when I was a kid, and sit in my room by myself and tinker around with things and follow my curiosity, and see what comes of it, and see how I can repeat that process over and over again, of doing that, make something that makes some money, free up a little bit more of that curiosity, a little bit more of that freedom, and repeat that process over and over again. And so now I've been doing that for 15 years.

12:33

Now that you've transitioned from that narrow perspective to perhaps a wider perspective, if you could say that, you almost now fall into the trap of choice, you have so many things that you can do.

12:51

Yes.

12:52

How do you get over that?

12:56

I hope that I do. I am in that right now. I've got a series of books that has two books in it right now, The Heart to Start and Mind Management, Not Time Management, it's called the Getting Art Done series. And there's one more book that I want to add to that trilogy. And these books are about getting art done. These books are about creative productivity but, and I think that I got interested in writing these topics because these are things that I struggled with myself, but I am also aware of the fact that if I were to only write about creative productivity for the rest of my life, I'd be succumbing to the resistance, or that Steven Presfield calls the resistance, is it's easy for you to just shadow box or, I don't know what a good metaphor is, wrestle with this, almost a straw man of, how do you do creative productivity? How do you create things? How do you get over the mental and emotional barriers to discover what it is that you have to offer the world and put that into the world?

14:15

Well, if I were to do that forever and not actually do that myself, not that I haven't, but then I think that would be bad. I want to avoid that. And so in the meantime, as I'm working on this third book in the trilogy, I'm also working on the side on other projects, they will be a fiction project, or a project with a hobby that really interests me and things like that are happening in the background. And I'm dabbling with those things, hoping that they will pull me in, or reach some level of success by being back burner projects that, are they able to pull me in and away from the things that are already successful? And I recognize that, that trap is there. And so that's what I say I hope that I can escape that trap. Talk to me in five years and we'll see whether I've done it or not, if I'm so fortunate to continue to be alive and healthy and doing these things. Yeah.

15:23

How do you deal with the fact that your, whatever you choose, you are going to miss out on something? And in some ways we all have, it's unfair to say that we all have a one unique thing that we are good at and that we can share. A lot of the time me is we, we have so many different parts to ourself. And the work that we do is therefore so many different things. I could imagine doing so many different jobs and-.

15:56

Yeah.

15:57

... how do you deal with the fact that actually you got to try and pick one, because you know the focus needs to go in a certain direction, but by doing so, you're letting other ideas and other passions not be that focus?

16:13

One way that I try to approach things is, well, I guess, first of all, there's this belief that you have to really commit to one thing, and that is somewhat true, but at the same time, you can actually make a decent amount of progress on different other things just by making little side projects. And I think that this age of media that we live in, where you can make a little Twitter account for your project and just have it sitting on the side and tweet things and grow things and play with it. And then maybe that feeds your original project. And then maybe someday that has grown to an extent where you jump into it. You can actually have a lot of different things going on at the same time.

17:02

And you don't necessarily have to specialize. You can go do something that's totally unrelated. And if you're having fun, if it's successful, it can actually make your other things quite successful too. Look at Elon Musk, how many different businesses is he in? And it's continues to raise his profile and these things feed into each other. And that's something that you can be strategic about, but in some ways it just takes over itself. Every little project I do, I've got secret projects on the side that nobody knows about that I mess around with and stuff. And sometimes things from that, I learn something and then it helps with my main projects. And I think over time, those things can all, they can all feed one another and they can grow into different things.

17:52

Are there any other ways other than working on multiple projects that we can optimize for emergence and accelerating interest?

18:09

Yeah. I think systems not goals, instead of saying I'm going to do this particular project, you create a system that helps you create multiple tiny projects that build into one another. I have easy examples because I'm a writer. And so every tweet that I tweet on Twitter is one of these little projects. It is me sharing an idea, it's me testing something out. And sometimes I spend hours on a tweet. And then I have systems for collecting, which of those ideas went really well? And then they become Love Mondays Newsletters. It might be a 200, 300 word essay that I write about those things. And then from there, it might become a podcast episode where it's 1500 words on my podcast, Love Your Work.

19:06

And then from there, I can keep doing that. And then there starts to become this big body of work where I can say, oh, these pieces fit together. Now that's a book. And so that's my process now for writing books. And I have systems for these things. I have systems. When I like my own tweet on Twitter, I've got a Zapier automation that shares, that saves it to an air table spreadsheet. I can sort them by the number of likes and I can keep track of which ones I've expanded into larger ideas. I've got the system set up where I can add like a book, or a cool tool, or a quote that I've collected from somewhere. And it sucks it all up into a markdown file that I can then just copy and paste into my email system. And that's a system that works. You build these habits, you build these systems, you create what you create, not necessarily just to create those things, but to become the person that you want to be.

20:11

So, because of these things, I am reading constantly. I'm constantly taking notes. I've used this system called Zettelkasten that I've written a short book about, that also has emergent properties where I'm just working on one little note at a time, just this one highlight from this book makes me follow-up on these different elements and make one little note and put some tags together. And then the next thing you know, it connects together with some other note. And the next thing you know, I've got a whole article idea. These things just emerge from these systems and habits that follow the ebbs and flows of my curiosity, that follow the ebbs and flows of my creative energy, and help motivate me to do the things that I would hope that I would be doing.

21:00

If you were to come out of your own circumstance there, how do you think someone could use a systems approach to finding work?

21:15

So, for example, if you were say a freelancer, what are you interested in? What are you really curious about? That's something that I think that a lot of people don't get the chance, or give themselves the mental space to ask themselves, looking for that little dopamine hit when you see something that's extremely interesting to you that is in some field rather than thinking, okay, well, what's going to pay me the most, or what is exactly going to fit my skills and experience? And then trying to reverse engineer those things. So let's say you're in one field and, but you want to get into another field and you find a company that you really want to work for. Well, then ask yourself, all right, well, who is making decisions at that company? And if you look around, you might float around on LinkedIn for a little bit and see where the connections are, and try to see if you can find your way in there, or you can do some kind of a stunt that gets them on your radar, for example.

22:38

So if I were to apply that to a job, I don't necessarily have an idea right off the top of my head for that, but for myself, I recently advertised my book in Times Square. And I found just through what was interesting to me, I found that, oh, you can actually advertise in Times Square for as little as $20. Okay. Well, but if you take a picture of it, it's worth a lot more than $20, because now you've advertised in Times Square, and you can tell other people about it.

23:11

So I advertised in Times Square, hired a photographer to take a picture of it and a video of it, shared it, blogged about it, shared it on Twitter. We got a retweet from Tim Ferris, 1.8 million followers. I got invited to speak at the New York Public Library because of that, because I just got on the radar. It was one of these emergence things where if I would've just like, if I tried to message Tim Ferris and get him to retweet something, he's not going to even see it, or care. If I message the New York Public Library and say, I'm going to speak there. There'd be like why? You don't even live in New York. I don't understand why you would speak here.

23:49

So I think thinking indirectly is one of these ways that you can take advantage of the, those network effects, that complexity that you don't see, that I think is full of untapped opportunities. It doesn't have to be all of your time and energy, but having a little bit of fun, letting some randomness take over, you can have all sorts of exciting things happen that you never could have possibly foreseen.

24:18

Why aren't people more random? What stops us doing that more?

24:25

Well, we want to feel secure. We want to feel like we know what's going to happen. We want to be able to tell our friends and family why we're doing what we're doing. And if you can let go of that, then that becomes, it becomes a lot more comfortable to be random. And this is why something like the barbell strategy works out really well is, maybe you have your day job. You do some really secure thing. A lot of writers, Charles Bukowski worked at the Post Office. Anthony trollop was, I think he also worked at the Post Office. John Grisham was a lawyer. You do some writing on the train on your way to work, or at night when you get home, you write yourself a novel, you put it out there and maybe something amazing happens.

25:17

I think that just that we are afraid of uncertainty, and that's natural. So maybe just do just enough to keep that fear at bay, but also do some things where you're like, ooh, what's going to happen? I have no idea if this is going to work or not. Something exciting is going to happen. I want to see what tomorrow is like. And I think that's a great way to embrace randomness.

25:51

It strikes me that people may not do so because they're worried about failing, looking stupid.

25:59

Yes. That too. Yeah.

26:00

Trying something out and it not working, because in some way we need to say that we were doing something for a reason then we've achieved it. And that kind of more random, sporadic failure mode doesn't really come out.

26:18

Yeah. Yeah. We're afraid of failure. And that's part of the process. And I think this also comes from that upbringing, that programming, cultural programming that we have, that we're used to being in this world where you follow these steps, and if you follow these steps, you'll have this result. You'll often hear people talk about entrepreneurial advice, career advice things, and say, well, that's survivorship bias. You can't just drop out of college like Mark Zuckerberg, or Bill Gates and expect that to work, because they're the survivors. You didn't hear from the people who dropped out of college that weren't successful, but you apply that to any other thing where somebody dismisses some advice, or something that they could possibly do because they look at the person who succeeded and say, well, they were a survivor.

27:14

If you are building a product, a great product often feels like a toy. It almost feels like a scam. It's so obvious to you that you're like, it's strange in the same way that like Airbnb let me host strangers in my house. What? No, I'm not going to do that. That sounds ridiculous. But it's such an obvious idea hidden in plain sight that is so evident to us in hindsight, because it then fits the narrative fallacy. But looking forward, it feels strange. How do we get over that feeling of feeling strange, of embracing those playful kid-like ideas as the future?

28:02

Yeah. And this goes back to what we were, that last answer was supposed to be about getting over failure. And the lesson from that is that failing is a part of the process. And I think it's useful even to do things that you expect to fail, or that you don't know they're going to work, and it's almost like it's a joke. I love the story of Teenage Mutant Ninja Turtles. These guys were sitting in their apartment and one of them doodled ninja turtle, actually if you think about it, that's actually a pretty funny idea. Turtles are really slow, ninjas are really fast. And so the other guy thought that was hilarious. He drew a ninja turtle, and then the other guy wound up and drew four of them in a stance like this and then decided, oh, these are teenage and mutant ninja turtles. And they're laughing to each other. And one of them recalled that he said, oh, this is the dumbest thing ever. They sold a billion dollars in toys, just toys in four years.

29:09

Not dumb anymore.

29:10

Yeah. They went ahead and they self-published their first book, they scraped together maybe $3,000 or something to self-publish their first issue of Teenage Mutant Ninja Turtles. That's the thing it's like these remarkable things that seem dumb that your friends and family might even say are dumb, those are the things that you should be doing. And that's one of the tough things to get over is, are they going to laugh at me? Those sort of things, because those are the things that are remarkable.

29:38

So much of this comes from curiosity and this playful curiosity. How do we cultivate curiosity?

29:48

I think it's there. I think it gets beaten out of us. It was beaten out of me for sure. When I went out on my own 15 years ago, that was, I remember waking up that first morning opening my eyes and it was just like, oh my God, I have nothing on the schedule today. I've resolved that I'm not going to work for somebody else. And I have no idea what I'm going to do, but I was just so burnt out. And so I thought back to when I was a kid and when I would be in my room by myself playing, counting change, or playing with magnets, or drawing pictures of ninja turtles. And I thought that feeling of, oh, I forgot to eat, or just what time is it? Oh my gosh, I can't believe that much time has passed, or just that feeling of being immersed. I just, oh, what? When was the last time I felt that way? Can I still feel that way?

30:49

And so that was the process for me was, that was my main metric. Can I recreate that feeling? And it's not always going to be the same things for me, because I'm somebody who gets curious about a new thing every couple weeks or so. And so that's what I've been doing for the last 15 years, is just chasing that feeling. And part of it was also because down the hallway was Guitar Hero, a video game, which is very fun. And I knew that whatever I decided to do with my time was going to have to compete with that, only I was going to be there to motivate myself, and whatever I chose to do was going to have to be more fun and engaging to me and productive than sitting and learning how to play a fake guitar with buttons on it that doesn't actually even teach you how to play a real guitar.

31:47

Could I finally ask you about meditation and-.

31:50

Sure.

31:54

... what role do you think meditation plays in finding our best work?

32:00

Huge, totally underrated role. And maybe it's one thing that I take for granted, because I've done quite a bit of meditation and I don't, actually if you were to ask me, I wouldn't have even thought to bring it up, but it's actually incredibly important to my work. And when it has been most fruitful for me was when I did a 60 day 60 hour meditation challenge. Picked this up from Naval Ravikant who was an angel investor and very successful entrepreneur. And it basically, he espouses this no effort meditation. And this really appealed to me because sometimes meditation for me can become a toxic productivity thing where I feel like, oh, I'm not doing it right. Oh, I've got to keep my streak up. Things like that.

33:01

And so he espouses you just sit there with your eyes closed, but you have to do it for 60 minutes and you let your thoughts flow, and you don't have any judgments about those thoughts and you're not trying to not think about something you're not trying to think about something. And something really amazing happens right around the half hour mark for that. And it just changes, like this everlasting gobstopper. One of the things I discovered was by creating that time where I'm doing nothing, those crazy ideas that I would normally just forget about, or gloss over, or not pursue, those started to take a bigger presence in my mind, to where I might have had the idea of, oh, maybe I should write a book about Zettelkasten. No, no, that would never work because that's just too obscure. Nobody would really care about that. And I've got other things I want to do.

33:54

Well, when I meditate for 60 hours in 60 days, I started thinking about that more and more, and then it became that much more important where I decided, okay, well I will write this book about Digital Zettelkasten. And it turned out to be this surprise hit book for me, where it was an 80 page book that shares this methodology that I had struggled to learn myself. And immediately was selling quite a few books. I've sold foreign rights deals for it and stuff. And so creating that space is incredibly important. I think that's what's useful for meditation, is if you are to turn it into a productivity thing, which I know is in some ways a bastardization, or a perversion of what meditation is supposed to be about, it actually is quite productive, because it helps those ideas take presence, and being productive these days isn't so much about how quickly can I do this? How many of these can I produce? It's more about what's the quality of this idea?

35:03

I'm so grateful for you taking the space to have this conversation too. And I'm particularly grateful for your insights on systems, as there's such a healthy antidote to the hustle ultra productivity culture. And yeah, I'm really thankful.

35:24

I'm thankful for being on here, Ben. It's an honor to be invited and I think we were going to have a conversation, but I ended up just answering all your questions.

35:38

Loved every second of it. That was really good man. Really good. And I think for me personally, the thing that I will take from that definitely, the way that you talk about that system, it is such a breath of fresh air compared to your other complete focus crap where we all just stay in our lanes and you got to work really hard and do this one thing over and over again until it works in the end. I love it.

36:09

Yeah. There's this unsettling kind of thing lately where people seem to think that the opposite of that type of productivity is to reject the entire idea of productivity.

36:26

Yeah.

36:27

There's these books about, ah, screw productivity, or here's how to do nothing, or your life is going to end anyway, et cetera, whatever. Well, there's an alternative to that. It's called being productive it's something that matters to you, and that you actually enjoy. What do you think you're here for? All right.

36:49

Thanks a lot.

36:49

Have a great evening. Bye.

36:50

You too. Have a great day. Cheers.