How The Pros Do It: 10 Questions With David Kadavy

The only way to reach your targets in life is to get to work. But it’s easier said than done. Only a fraction of people in life are actively working towards their goals. They know how to create and use the right tools and processes to generate progress for themselves. A lot of these people have a ton of interesting things to say. So I thought I’d interview them.

Most of my weekly guests created their own business, and they got where they are today by successfully implementing self-discipline in their life. To each one of them, I ask questions about their life, their learnings, their tools, and sometimes about which celebrity they would like to have coffee with.

There are no rules for success, only consistency in the work you do. None of the people I interviewed are super-humans. They’re just dedicated, and they have a lot of awesome things to teach us.

Let’s get to it.

This week, my guest is David Kadavy. David is the author of Design for Hackers and The Heart to Start, and host of the Love Your Work podcast. He lives in Medellín, Colombia. After working in the startup world in California for a few years, David decided to build his own business around blogging, podcasting, and writing books. He tries to get as much creative output as he can, and to share what he learns along the way. You can find David here on Medium, and on his website at

In 2004, you were stuck in a cubicle in Nebraska. You gained enough courage and willpower to quit and build your own business. How?

Well, it’s not exactly how it happened. At first, I started a blog. Over the next year or so, I worked on that blog and made it better. I won a design award, and I think I remember that helped me get connected with a new client. Then, this founder in Silicon Valley found out I existed, because this new client recommended me to him, and because I had won this design award which was a big international honour. I ended up working in Silicon Valley through that connection. I moved out there, very happy to leave Nebraska. I worked in San Jose for a year, then moved up to San Francisco, worked at another startup for roughly a year.

On July 17th 2007, I got fired. I couldn’t tell you exactly why. I didn’t really ask a lot of questions, because I probably should have quit myself anyway. I didn’t want to be working there, but I just didn’t have the guts to quit. When I did get fired, I remember being in this meeting, I turned to my boss, smiled at her and said: “Thank you very much”. There was no sarcasm in that. I truly meant that July 17th 2007 would go down as a very special day in my life.

What really helped was that I had shovelled a lot of money into a stock portfolio at the time. I got very lucky, because I bought Google, Apple and maybe some other stocks that did well at that time. I ended up having a pretty good retirement account, which was basically enough to make me wonder: “Why am I working this job that I don’t like that much, when I have this money?” I had the option to explore something I was more interested in.

What is the number one habit/routine you attribute the most success to in your life (online and/or offline)?

I would say the weekly review. Sitting down once a week, and reviewing everything that’s going on in the next week, maybe in the next month, and really thinking through your priorities ahead of time. That way, you’re not trying to figure everything out in the moment. That is my number one thing.

The One Book you recommend for self- improvement and/or productivity?

Getting Things Done, by David Allen. It really changed my life, and I still read it regularly. I actually read it the way a lot of people would read a religious text. I will go to a coffee shop on a Sunday morning, get a tea, and review my highlights and favourite passages in the book. I get out of that coffee shop feeling light and free from that process.

Can you tell us about your use of journaling and goal tracking?

I have long been sceptical of goals, I don’t really like them. I wrote a post a very long time ago called “goals are bananas”. The basic idea behind it is to imagine you’re a monkey swinging through the trees, and you’re really focused on this bunch of bananas way across the jungle. But because you’re so fixated on that one bunch of bananas, you’re going to miss out on some opportunities. You’re going to miss branches that you could grab easily, so that you wouldn’t fall and get eaten by a tiger. You’re going to miss other “goodies” you could find in the trees, miss others bunches of bananas.

The world is too random and unpredictable to be focused on goals, especially as a creative. I obviously have things I want to do. But I’m constantly trying to be aware of what opportunities are in front of me and how things are changing. In my opinion, things change too fast to have fixated goals that don’t evolve.

When it comes to journaling, that is something I do a lot. I try to go to a coffee shop with only my journal and write about whatever comes to mind. It can be the most basic and obvious things, that’s where you find the insights. I mostly do it when I have a feeling I’m not on top of things. I use journaling for 2 things:

  • Get what’s in my head out on the paper. Like a writing training.
  • Get a sense of control over what’s going on in my life.

I’m not super consistent with it, and I think part of that is because I used to do it more regularly, so I trained myself to be able to stay on top of things. I can now do that pretty well without journaling too much. I can do it in my head, and I think this is the ultimate goal. To have enough of a system, enough habits and routines set up to develop a sustainable system where you’re going about life and the proper things are getting done and digested.

I do write at least 100 words every morning on my AlphaSmart NEO, before I even open up my eyes. That can be journaling stuff sometimes, whatever is coming to my mind in the morning. When I’m done, I delete everything.

How do you manage your time between your blog, your podcast, and your book projects?

I don’t currently blog a lot, but I do have systems set up for organising everything I’m doing. The point is to get more quality output out of the same 3 resources:

  • Me
  • My Time
  • My Brain

The most formal system I have is with the podcast. I have 2 interview seasons, 2–3 months throughout the year where I try to get an interview a week. I’ve determined that if I do that, I’ll have enough interviews for the whole year. I have identified certain times of the year where it’s difficult to do interviews: summer, and right around the holidays and New Years.

When I book an interview, I have my assistant update a google spreadsheet with a lot of information and tasks related to the project. She then exports everything as a CSV file, and imports everything into Todoist. With this system, I get all my tasks lined up, and I know that if I follow these tasks I will be ready for the interview on time and that the episode will be ready on time. I write the intros for all the interviews and episodes on a monthly cycle, so that the last Thursday of each month I am sending things off to post production.

It’s important for me to break things down into tasks, so that I never have to sit down and do a big block of creative work at once. It is these 5 minute bursts that are spaced apart enough to have incubation take over. Instead of sitting down and trying to write a podcast intro which would take an hour and might be agonising, I break it down into many things.

  • I listen to the podcast conversation while I’m cooking or eating.
  • I take notes, I listen to it a couple times.
  • I do a five-minute brainstorm.
  • I come back to this brainstorm a couple days later and I revise it.

In the end, what would take an hour and would be unpleasant ends up taking 20 minutes of actual “sit down and work” time, one session at a time. It’s a leisurely consumption of the content that helps me get ready. I’m always trying to use incubation as best as I can to get things done.

Another thing I do is having a back burner and a front burner. Podcasts are back burner, because I have systems in place that I follow for those, and it’s automatic. I don’t need my very best creative energy to get the work done. On the front burner, I have things like a book, which is a lot more mental heavy lifting, trying to figure out a lot of stuff. The front burner is the first thing I work on every morning.

Finally, I try to maximise my amount of time spent in reverie, where I am doing what I want, everything is a little more spontaneous. The systems I have set up for myself allow for the spontaneity.

What is the number one productivity item you can’t live without?

My Moleskine Volant Notebook. It is a very small notebook, about the size of a credit card, and I have a Pilot collapsable pen that I use with it. I carry this around in my pocket, and I call it my inbox. Anytime I think of a thing that needs to be done, or an idea that needs to be captured, I quickly pull out my notebook, write it down, and put it back.

Now, the “obvious” thing to do would be to write it in my smartphone. But to do that I have to look at my smartphone, to touch my smartphone, and that is just a gateway to distraction. It’s also cumbersome in a way. With the notebook, I can be confident that at some point in the next 1 or 2 weeks, probably during my weekly review, I will go through the list of things that I have written and then put them in their proper place.

The type of notebook comes down to personal preference. I did quite a bit of research and tried a few different notebooks before I landed on that one.

You mention on your website that you question the mores of the traditional publishing industry. Can you explain why, and what your approach to blog/book marketing is?

Let’s start with the first part of the question. Why do I question the mores of the traditional publishing industry? Well, I feel like you have to. It’s such an old industry. There’s surely a lot of money in it, but a lot of ways they do things is based on a certain scale. You have big authors that sell a lot of copies and because of that, you’re going to have to print a lot of books, and you’re going to need a lot of money upfront to do that printing, and you’re going to have a very launch-focused way of getting books out there.

Now, besides the fact that the world doesn’t have to work that way because now we have print on demand and the internet that can connect people to different ideas very quickly and easily. This whole approach just doesn’t fit my personality, because it’s a very top-down industry. Before you even submit a book proposal, you basically have to write the whole book. After you do that, your book comes out 2 years later.

Overall, I guess there’s a lot of books they put out I don’t really like. In my opinion, they’re just blogposts that are 200 pages of filler. I shutter at the idea of writing one of those books, and this industry just doesn’t appeal to me.

The second part of the question is about my approach to blog/book marketing. My take on this is that I try to do what’s interesting to me. I write about the problems I’m struggling with myself so that I can help myself and others in the process.

I spend money on Amazon ads for selling books, because I feel like I have to do that. Amazon seems to be paid-for-play right now, and I guess I should be grateful that I can break even on my ad-spending. I buy a lot of ads, which sells a lot of books, which seems to increase my influence.

On the future of online marketing. I think that more and more people, including myself, are getting tired of having to prove that we’re not robots, and having to sort through low quality information that was created to appeal to robots. I’m talking about the algorithms that run all those online systems. Somewhere in the middle of it all, there’s hopefully going to be room for more authenticity. I think it’s going to be more and more about personality, people. At my level, I try to be authentic in the most marketable way possible.

How important is time off for you, and what do you do when you take time off?

I am mindful about taking time off in terms of getting enough sleep, spending time with people who are important to me. Beyond that, I try to integrate the recharging aspects of taking time off into my work itself. By managing my mental states, I try to make certain work that will bring my projects forward but at the same time energise me.

For the last 4 years, I have been on this mission to double down on writing and podcasting, and I would like to take more actual time off in the near future. Right now I can’t really afford to that, but hopefully I’ll get to a point where I can do it. It’s probably time for me to take a week or something, but it would still be a week where I’m trying to think higher level about work. Because again, I try to choose what I do so that I don’t want to take time off.

You have an Instagram account for your business. How do you tie the 2 platforms together, what connections do you see between what you have to offer and Instagram?

I don’t get a lot of pleasure out of using instagram. But if I do use it, I can get sucked into it just like anybody else. In that sense, I’m trying to be very intentional about it. This is the way I approach many things that are speculative. I’m dabbling in using Instagram. I’m working at making it better, I seem to be able to have followers pretty easily with it, but I don’t have a clear payoff for growing my Instagram following.

I have enough of an audience right now that I can make some money, and I’m not making nearly as much money as I could be with the audience that I already have. There are a lot more ways I can help these people. Ways that they would be willing to pay for, that would increase my income and revenue. I would like to concentrate on those things rather than growing my Instagram.

I’m just doing a little bit here and there, it’s informal. I don’t have a quota. We were talking about systems before, I try to come up with some sort of a system for Instagram too. If I were to go to this hashtag once a day, like all the posts there, message anybody who shared this book, has this many followers, and then offer them a copy of my book, then what would happen? Should I do it once a week? More? Less? I try to come up with strategies.

At the end of the day, it’s important to not get distracted by social media too much. Trying to stay off social media is much harder to do than to find something you love to do and you want to succeed at. Once you do find that one thing though, it is much easier to disconnect, because the cost of being on social media becomes incredibly high. If you’re on social media, you’re missing out on that one thing you said you would work on.

If you could have a coffee and talk about anything with a personality (dead or alive) you admire, who would it be and why?

It’s funny because the first person that comes to my mind is Seth Godin, but I’ve already had him on my podcast twice and we talked for a couple of hours. But that’s the podcast. It is a formalised way of having a very focused conversation. There are some things that would probably be different if we had coffee together.

I guess I wonder how he navigates being authentic with all the market pressures that are out there. As media changes, different tactics become more fruitful, and not all those tactics are dignified. Seth Godin strikes me as somebody who has maintained his dignity as a creator.

He is very smart about marketing and how he gets attention for his products and markets things, and he is able to do it in a very classy way. That’s incredibly difficult to do with the way media works, what captures people’s attention. It would be interesting to hear more of his thoughts on that. I guess I could just ask him next time I have him on my podcast. Maybe in a couple of years.

There you have it. I want to personally thank my guest for taking the time to provide me and my readers with really insightful answers. I am deeply grateful to David Kadavy. Thanks a lot, all the best in your future projects!

And thanks to you for reading my content!

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