In the second part of this blog series, I shared how I treated my book as a series of small projects culminating in a final product.
The same was true for each of the 10 chapters it contained: each one was its own project, with a deadline and a goal for what that chapter was trying to achieve. Each chapter had its own project folder (according to my PARA Method), where I collected everything I would draw on – notes, sources, supporting materials, stories, action steps, and key details.
These projects guided me over the 14 months it took to finish the manuscript. Here are the five pillars of my writing process that I depended on to make consistent progress, each one building on the one before:
- Pre-existing blog posts
- Morning writing sessions
- Writing retreats
- Outsourcing my life
Let’s dive into each one.
#1 – Pre-Existing Blog Posts
The single most important resource I drew upon was my blog, where I’d published almost 500 articles containing more than 700,000 words since 2014. I always viewed these articles as research for a book I would write one day, and that is exactly what they became.
On average, about 70% of each chapter in the book was made up of writing I’d already published on the blog, though it often had to be extensively rewritten to conform to its newfound style and purpose. I can’t overemphasize how crucial it was to be able to start each chapter with 70% of the background research already done.
The remaining 30% came from notes I retrieved from my Second Brain. In total, I drew on 254 notes (saved as long ago as 2015) to round out the manuscript. Trying to digest all of those at once would have been a nightmare. By breaking them down into 10 chapter-specific groups, I only had to load an average of 26 notes into my head to complete each chapter. Totally doable!
Here’s what the project folder for Chapter 4, on how to capture information in one’s Second Brain, looked like:
That’s only 10 short notes encompassing the vast field of “knowledge capture”! And it was more than enough material for my needs. In fact, I didn’t even use all these notes and had to cut out a lot to get it to a reasonable length.
Here’s an example of one of the notes from this folder, containing my responses to a Q&A about knowledge capture. The bolded passages are the ones I thought were good, and the highlights in yellow indicate points that were important enough I considered incorporating them into the book. (You’ll notice that this is my Progressive Summarization technique in action.)
Here’s another example (view the public note) of how I deconstructed a publication from Microsoft called The Innovator’s Guide to Modern Note Taking, turning it into a highlighted chapter-by-chapter summary that was easy to reference in the flow of writing.
Treating each chapter as its own self-contained project also made it easy to go back and cite all my sources once the writing was complete. All that material (whether I ended up using it or not) remains available in my Second Brain in Evernote for reuse in future projects I may take on.
#2 – Outlines
After I had compiled the notes I thought I might want to use in a project folder for a chapter, my next step was to turn them into an outline. In my book, I call such a “digital outline” that links to other notes an “Archipelago of Ideas.”
Writing is inherently hierarchical, taking the form of:
- Point 1
- Supporting point A
- Supporting point B
- Supporting point C
- Point 2
- Supporting point A
- Supporting point B
- Supporting point C
Which means that the outline I used as the “scaffolding” for my writing also had to be hierarchical. This is where outlines can be so powerful: since they mirror the logical structure of the writing they will ultimately turn into, outlines can serve as a kind of “map” of where you’re going as you put down one sentence after another.
For example, here’s part of my outline for Chapter 1, where I draw on my past notes about what it feels like to be disorganized. Note how the green links lead to the original source, while the points indented underneath them contain the specific excerpts from that source that I thought might be worth using:
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:
- 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.
- 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.
- 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).
- 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
- 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.
- 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.
- 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
- Exercise regularly before and during the retreat, because you’ll need the physical stamina to stay in flow for such long periods.
- Set a rule that you’re only allowed to remove things, not add things, which helps you avoid the temptation of “doing more research.”
- 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.
- 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).
Here’s how I spent the 58 hours of one 3-day retreat (notice that even with all the focus I could muster, less than half the time was actually spent writing):
- 24 hours of writing and editing
- 16 hours of sleeping
- 3 hours resting
- 3 hours taking and reviewing notes
- 3 hours eating
- 2 hours exercising
- 7 hours miscellaneous
#5 – Outsourcing My Life
The fifth and in many ways most important pillar of my writing process was essentially outsourcing my life during the period I was most immersed in writing.
Early on in the process, it became clear that I simply didn’t have the bandwidth to manage my quickly growing business, conduct my busy personal life, care for my new family, while also writing a 65,000-word manuscript. It just wasn’t physically possible.
I made the decision to lean on all the people in my life who supported me. I know it was an incredible privilege to be able to do so. As I wrote in The Psychological Toll of Writing a Book, some of the steps I took included:
- Limiting myself to two activities – focused writing and recovery – and eliminating, outsourcing, reducing in scope, or postponing everything else (including signing up for a daily meal delivery service for our family, hiring someone to do all our housekeeping and laundry, and letting my team handle most decisions).
- Leaning on our families – my wife Lauren and I made more requests of our families during this period than ever, for food preparation and babysitting and home projects and much more, and I discovered how fortunate we are to have such generous, caring families behind us.
- Spending money to save time – we were fortunate to have an online education business that was booming during the pandemic, and I used the money that was coming in with abandon to save even the smallest amount of my mental energy, from buying a new minivan to hiring a personal assistant and personal trainer to getting everything we needed delivered.
- Getting feedback constantly – I didn’t have enough mental horsepower to make all the decisions that needed to be made for the book, so I drew heavily on the ideas and contributions of everyone around me. I would discuss thorny writing challenges late at night with my wife, get feedback from the team on key decisions, talk through my thinking with friends, collaborators, and advisors, and even run polls on Twitter to test different options.
- Trusting my publishing team – early on I realized that I either needed to trust the people I’d partnered with to bring this book to fruition (my agent, publisher, and editor) or else I’d have to fight them every step of the way. I knew I didn’t have the energy for that, so I decided to trust them even when I didn’t understand or agree with their advice.
In the next post, I’ll share how we marketed and sold the book that emerged as a result of this process, leading to a spot on the bestseller list.
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