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David Kadavy: Mastering Creativity

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David kadavy

Writing is so central in David Kadavy’s life that he organises his weeks to optimise creative output.

He writes mainly in the mornings. And he writes more at the beginning of the week than towards the end of it. That’s because he has more creative energy on Mondays than on Fridays.

So in his grand schedule of creativity optimisation, he tends to plan podcast sessions on Thursdays. I was lucky to get him on a Wednesday, though. So who knows, maybe I caught him on a more creative moment than other podcasts.  

More podcast hosts

The more significant decision for his writing career was moving from San Fransisco to Chicago, and later, from the USA to Colombia. And even though he has now been living in South America for nearly six years, surrounded by coffee, David doesn’t consume caffeine. 

You can read all about these decisions in his books The Heart to Start and Mind Management, not Time Management. But I’ll give away one of the unique benefits of this move: he writes in English during the day and talks Spanish at night.

Switching between these languages triggers a disconnection that makes him think more deliberately about language. 

By translating the Spanish word desayunar back to English, David found that “breakfast” literally means “to break your fast”. Pretty straightforward, but strangely it’s something I also only discovered after learning Spanish. 

Writing Design for Hackers

Everything up until signing his first book deal was smooth sailing. But then came the hard part. The publisher wanted a tight deadline. Six months was all he had to get the book ready, and within a few weeks, he already had to present 25% of the book. If he didn’t make the first deadline, they could cancel the deal and claim their advance back.

Even though he was well-prepared for this, something didn’t work. He had already fired clients, and he had set his mind on not dating or going to parties for a while. Yet, despite all the free time, nothing came. 

The truth is, he didn’t know how to write a book. He had never written more than a long blog post.

As the days went by, stress and anxiety increased. He felt physical agony. But everything changed when Noah Kagan invited him for a retreat in Costa Rica.

When Noah saw him struggle, he came in with some advice:

“Draft, outline, polish. Break each chapter down into those three phases. Divide up your timeline. Put it on the calendar. Stick to the calendar. You’re done.” 

It sounds so simple, yet it was life-changing for David.

Visual Noah Kagan quote to David Kadavy

Now, he has a system in place which is controlled by his mind and not his time. Yes, things are on his calendar, but they’re optimised for the right state of mind at specific parts of the day.

On a micro-scale, he goes through four stages of creativity while working on a book:

  • Preparation when he researches at night.
  • Incubation during his sleep.
  • Illumination while he’s writing in the morning.
  • Verification when he edits later during the day. 

You can read more about this in his book Mind Management, not Time Management.

“Organise your tasks not by project, but by mental state.”

Mind Management, not Time Management

A few other great techniques from this book are motivational judo and inflating the investment.  

Motivational judo means you start with something unnegotiable, like writing 100 words in the morning. Even when you don’t want to, you need to hold yourself in a firm grip and get started. Once you make it to those 100 words, you’ll often feel happy enough to continue.

Inflating the investment means we can’t get started on something because there isn’t enough time. So we just scroll social media for 15 minutes. However, every small amount of time is enough to make some progress. It’s just about finding low-commitment activities where interruptions don’t matter much. 

David, for example, reviews some of his Zettelkasten notes when he’s waiting for someone and highlights the highlights. (See Tiago Forte’s Progressive Summarization.)

Traditional publishing and self-publishing

Back to the days before David’s first book. He had been blogging for a while when he wanted to use writing as leverage to secure a speaking slot at South by Southwest®. Despite his great effort, he didn’t get the slot he wanted. But he did get contacted by a few publishers.

It all went really fast after that. He hired an agent and without even completing a full proposal, he signed a deal with Wiley. Having the support of a traditional publisher gave him money in advance and the confidence to complete this arduous task. Without a publisher, he probably wouldn’t have had the guts to write a book back then.

When he was ready for another book, he wanted to go this way again, so he started looking for an agent.

How does that work, you wonder?

You sign up to Publishers Marketplace and start looking around for similar books. Which agent works on what kind of books? Which publishers do they work with? Which topics does this publisher cover?

When you’ve connected the dots, you reach out to your selected agent. Why? Because they can negotiate a better deal, they know how to handle contracts and they support you. In return, they do take a cut of the money, of course.

So far, so good for David. But then it got harder. He aimed for another publisher this time because he had a different type of book in mind.

This time, however, no one was as enthusiastic as the first time. Now, he did have to write a full proposal. And after having two 60-page proposals rejected, he realised traditional publishing wasn’t for him anymore.

He felt like he had to write what they wanted to hear, not what he wanted to say. It was uncomfortable. And the fact that he wasn’t a high-authority figure, such as an Ivy League Professor, Fortune 500 CEO or famous consultant, didn’t help either. 

These types of people guarantee sales, and publishers won’t give you a good deal unless they know you’re going to make many sales. 

But if you know you’re going to make many sales, you’re better off self-publishing actually, unless they give you a 6-figure sum, of course.

So David gave up on traditional publishing and started looking for other options. The breakthrough happened when, on the 77th episode of his podcast, David was talking to Seth Godin about his struggle. And Seth wouldn’t be Seth if he hadn’t given him some life-changing advice. 

“You learn by doing,” he said. And he advised him to start writing and publishing weekly. David followed up on that symbolic advice and wrote a few short reads as well as his second book The Heart to Start as a self-published author.

After that, he discovered more benefits of self-publishing, such as higher royalties and real-time insights. You run your own ads and see how they perform. You don’t know anything with a traditional publisher, and it can take nine months until you get paid.

Finally, he realised something else about traditional publishing. It’s more of an ego thing. It’s for people who want approval, reassurance, validation. And yes, some people will respect you more for it, but you won’t be better off. 

The AlphaSmart, David Kadavy’s oldskool secret

Most of David’s tools have one thing in common: they’re optimised for writing without interruptions.

His favourite tool is the AlphaSmart. This is a portable word processor with a typewriter-like keyboard and calculator-like tiny screen. Only four to five lines are visible and it only stores twelve files that can’t sync with Google Drive or anything else.

It’s the perfect tool to write without thinking. Editing is possible but it’s so painful you just keep moving. David uses this wonderful tool to capture his first thoughts in the morning. 

Sometimes he even reaches out for his device before taking off his sleeping mask. Then he types until it feels like he has reached at least 100 words about anything. When finished, he usually deletes everything. It’s not about producing something to publish but about making new connections. Sometimes, he even uses the devices when it’s out of battery. Since he doesn’t care about what it looks like, writing is still happening. 

“If you write for about an hour a day, you’ll become a better writer. If you read for about an hour a day, you’ll read a lot of books.”

David Kadavy

His second writing tool is an iPad hooked up to an external keyboard. He feels that it’s harder to get distracted and move away from your writing programme on an iPad.

In the past, he used Scrivener for his books. And even though it’s great because of its storyboard and formatting options, he switched to simpler software.

On his iPad, he uses 1Writer, and on desktop, he also prefers writing in markdown via Ulysses. It’s straightforward to use, and you can easily export full articles to WordPress, where it automatically uploads and formats.

David Kadavy’s writing tips and secret

  1. Allow yourself to suck. Don’t worry about misspellings, changing topics in the middle of a sentence, using bullet points or adding brackets. WRITE REAL SHIT. But don’t spend too much time on it.
  2. Embrace the power of incubation. Your mind is a passive genius; it’s incredible. During the off-time, your mind figures out complex problems, especially if you get good sleep.
  3. There are three c’s to being a great writer. Deal with one at a time:
    1. Consistency (have a regular schedule)
    2. Courage (put it out there)
    3. Craft (work on wording and style) 

The combination of tips one and two will take a lot of wasted time and pain away. Tip three only works if you focus on one aspect at a time.

And his secret? He never thought of himself as a writer. 

David still has a lot more to share. You can find more information via the links below. 

Books: Design for Hackers, The Heart to Start & Mind Management, not Time Management
Author: David Kadavy
Newsletter: https://kadavy.net/mondays/
Resources: https://kadavy.net/tools
Twitter: @kadavy
Amazon: Full profile (Book also available elsewhere. Previews below)
More by David:

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