The 5 Pillars of My Writing Process

Outlines also serve another purpose: they’re markers for where you left off. That is an important function when even a single chapter might take many weeks to complete, spread across dozens of writing sessions.

#3 – Morning Writing Sessions

I was used to writing multiple thousand-word articles since I’d been doing that for years on my blog. But each chapter in my book was about 6,500 words long on average, and after I’d finished a first draft of the first couple of them I quickly realized that this was an entirely different scenario.

Writing a single stand-alone article, all you have to remember is the main points of that one article. But when writing a book, you have to keep in your head 10 or 20 times more information. Every time I wanted to make an edit – whether it was changing the spelling of “note-taking” to “notetaking” or a much more substantive one like changing how I framed the purpose of a Second Brain – I then had to consider all the implications that change created.

Changing the spelling of a term is easy – all you have to do is perform a “find and replace” search. But for more subtle edits with unexpected side effects, it’s far more difficult. How could I detect that an edit in Chapter 7 to broaden the examples of “self-expression” I provide, also requires a different set of examples in Chapter 4 for which kinds of content they should save in their notes in the first place? (This is a real example).

Essentially, the “mental model” of the book you have to keep in mind is always growing, which means as the manuscript grows in size, the cognitive load needed to “hold it in mind” compounds exponentially. 

To overcome this challenge, I decided to do everything I could to make my weekday morning writing sessions as immersive as possible. I canceled all meetings and commitments before lunchtime, sequestered myself in our home office with noise-canceling headphones, and started each morning by picking one problem I would dedicate myself to that day. 

A “problem” could be deciding which term to use for a concept, choosing a metaphor to explain a technique, deciding on the exact sequence of points to build an argument, deciding which details in a story to include and which to remove, etc. It would often take an entire morning just to solve one of these problems, which explains how writing a book can take years.

I would typically sit down to work on my chosen problem for the day first thing in the morning, to give myself the longest possible runway for “cognitive liftoff” before I got tired or interrupted. But sometimes as I began to unpack the problem it would dawn on me that I couldn’t resolve the problem that day. Either because I didn’t have enough source material to draw from, or there were other more fundamental problems that had to be solved first, or because I simply didn’t have the energy.

In those situations, as soon as I recognized I wasn’t going to succeed on my current mission, I tried to switch as decisively as possible to preparing my tomorrow self to be able to solve it: distilling the notes I would need, getting feedback from others, listing my options, reducing the scope of the problem, and gaining clarity on what I was trying to achieve and why. My goal was to eliminate “thrashing” – the torturous process of trying to force myself to reach a goal that I wasn’t ready to reach.

#4 – Writing Retreats

Most of the writing problems I faced could be resolved in a morning writing session or two using the approach above. But some challenges were so great that they required larger blocks of time.

For those handful of major challenges, I turned to a more heavy-duty approach: off-site multi-day writing retreats. I ultimately went on 3 writing retreats over the course of about a year, and they were crucial to overcoming critical bottlenecks in my writing process. I chose the locations carefully:

• An Airbnb apartment overlooking the beach in Malibu
• A high-end hotel near the waterfront in Marina del Rey, in Los Angeles
• A rural inn in the wine country of Temecula in Southern California

These retreats had to be as efficient as possible because I was leaving my wife and infant son at home, and because each one cost thousands of dollars. Here are 12 guidelines and rules of thumb I used to make them as productive as possible:

1. Choose a place 1-2 hours from home, so it feels like “a world apart” but you don’t waste too much time in transit.
2. 3 nights and 4 days seemed like the ideal duration – long enough to get into deep flow, but not so long that I got lonely or felt like I was away from my family too long.
3. Choose hotels, because you want everything to be provided for you and to not have to think about bedding, food, etc. during your time there (for one of my retreats I stayed at an Airbnb, but I noticed the higher cognitive load of having to think about these things).
4. The ideal writing spot is minimalistic and quiet to avoid distractions, but also comfortable so that discomfort doesn’t become a distraction; hotel rooms are best because you can control every aspect of the room without needing permission
5. Do the prep work and planning for what you will tackle before you get there, otherwise you’ll spend the first day just getting your bearings.
6. Make sure you’re well-rested and well-slept before the retreat, otherwise you’ll be too tired to focus and just spend the days sleeping.
7. Ergonomics are important for such long writing stretches, so bring a laptop stand or external monitor, and external keyboard and mouse, and make sure your chair and desk are comfortable
8. Exercise regularly before and during the retreat, because you’ll need the physical stamina to stay in flow for such long periods.
9. Set a rule that you’re only allowed to remove things, not add things, which helps you avoid the temptation of “doing more research.”
10. Use long walks in nature and immersion in water (swimming pools, hot tubs, or a lake or ocean) to “reset” after a long day of writing.
11. Pay close attention to your diet, since you need to maintain your energy levels for the long haul; avoid one-time energy spikes like sugary coffee

Make sure you have everything you might possibly need for the duration of the retreat (at my retreat in Marina Del Rey, I had to go into town to get a bathing suit because I’d forgotten one, and it somehow ended up consuming half a day by the time I got back to writing).