In honor of completing my second book's transcript and shipping it off to the editor, I figured now was as good as ever to share a few insights on the writing and self-publishing process. I’ll start this article with a quote from C.S. Lewis that will (probably) begin every book I ever write: I write to you, not as an expert, but as “one amateur to another, talking about difficulties I have met, or lights I have gained.”1 It also goes without saying, but these insights have been colored by my own non-fiction writing experience (and informed by a couple of conversations with some fellow men of letters); my insights are by no means the insights—everyone’s process and preferences are different to a degree.
Consider this my disclaimer on the advice contained herein: your mileage may vary.
Now, with what remains of this article, we’re going to look first at the writing process itself before turning our attention to the self-publishing process in the second part. If your interests in this article incline more in the direction of self-publishing, feel free to skip the first part and scroll roughly halfway down. There you’ll find the section you’re looking for (though I make no promises you’ll find anything useful).
(1) The Writing Process
There are a great number of things I could write in this section, but for the sake of brevity, I’ve limited it to four: (A) find enough inspiration to start; (B) outline your answer; (C) take it bird by bird; and (D) be prepared to battle resistance at every stage.
(A) Find Enough Inspiration to Start
Before I wrote my first book, there was a long list of those I prematurely killed because I thought I had no right to talk about the subjects I wanted to write about. Even if I made it past my awareness of the Dunning-Kruger effect2 from my college psychology class (which tended to convince me that all thoughts of being equipped to create were the projections of self-delusion) there was always Impostor syndrome3 waiting to wipe out whatever ambition was left.
I knew I needed to come up with some sort of solution to thread the needle: how do I read and gather enough information and knowledge to start writing without overwhelming myself with all the information out there on a particular subject?
My solution? Pick three books that I want my book to be like to serve as my reference guides. Avoid the temptation to fall into the cycle of reading one more book before you start. Because if you wait until you’ve read everything, you’ll never start. To use my second book as an example, the three I picked were: (1) From Homer to Harry Potter: A Handbook on Myth and Fantasy; (2) The Hero with a Thousand Faces; and (3) Maps of Meaning.
After picking three books—typically ones I’ve read at least part of and can identify as covering similar material I want mine to cover—I’ll think about what was missing from those books or what’s the next evolution of those books. How can my book be a synthesis and addendum to these books? What do I wish they would have done differently and how I can work that into mine?
From there I’ll move on to the outline.
(B) Outline Your Answer
WARNING: This is probably my most idiosyncratic piece of advice that I’m certain others will disagree with me on, but it’s a process that is tried and true for me. Proceed with caution.
In law school, we’d have 2-3 hours to take an exam that would determine our entire grade in a class. Some classes had mid-term tests; others didn’t. So how well you did in the class turned on how you performed compared to your classmates in those hours. Needless to say, it was high pressure. Sometimes there were multiple-choice questions but typically most of the tests required answering analyzing some hypothetical fact pattern from a legal perspective and answering in essay format.
Some advice I was lucky enough to get early in my law school career was to spend about 25% of the time you had to answer an essay question outlining your answer. So if you had 45 minutes to answer an essay, 10-15 minutes of it should be spent outlining. Every time I took a test, I had to resist the temptation to just start writing (which is what most other students did) and force myself to write an outline first (like I did for this article). I’m convinced this accounted for most of my law school success.
Over time, what I realized was that outlining is writing. A good outline gives a snapshot of the core. It reveals the dots and makes the act of writing itself so much smoother when all you have to do is flesh out the details and connect those dots. If done right, it can be used as a north star to guide you through the process.
To this day, if I’m stuck writing in circles on something, I know that it’s because I didn’t take enough time to outline (or that I need to re-visit the outline). That’s not to say I still don’t write in circles from time to time—I definitely do; it’s just that I do it much less if I’ve taken the proper time to outline the main points of what it is I want to say.
IMPORTANT CAVEAT: It’s important that you don’t get stuck procrastinating at this stage, thinking that you have to have every detail perfectly plotted out and organized before you start writing. You don’t. When you write the original outline, you’re taking your best guess at what you think your book is about. And then, if you’re like me, you get about 30-50% through your first draft and realize the book is actually about something (slightly) different. So you go back and tweak your outline accordingly. Like my point on sources of inspiration above, you just need enough to get you headed in the right direction.
(C) Take It Bird by Bird
Once my outline is complete, the first thing I’ll do is go back to the three books that I picked as my reference guides and re-read them, highlighting text and placing sticky notes on any material that I think is relevant to the book I’m writing. Once I’ve harvested what appears to be the relevant material, I’ll find where I think it best fits in my outline and drop it in.
Then the real work begins! Waking up and attacking the outline one day at a time. For me, this typically means dedicating a week to each section, subsection, and sub-subsection. For example, in my second book, each of Hercules, Perseus, and Theseus are subsections within the section on Ancient Greece—so each of them got a week’s worth of research and writing.
At this stage, I usually leaf through the pages of Bird by Bird by Anne Lamott to remind myself of two timeless pieces of advice contained therein. The first is advice that seems to fly in the face of me saying to outline your answer but I trust you’ll find a way to reconcile the two:
E.L. Doctorow once said that ‘writing a novel is like driving a car at night. You can see only as far as your headlights, but you can make the whole trip that way.’ You don’t have to see where you’re going, you don’t have to see your destination or everything that will pass along the way. You just have to see two or three feet ahead of you. This is right up there with the best advice about writing, or life, I have ever heard.4
The second is a story that explains the title of her book and this section:
[T]hirty years ago my older brother, who was ten years old at the time, was trying to get a report on birds written that he’d had three months to write, which was due the next day. We were out at our family cabin in Bolinas, and he was at the kitchen table close to tears, surrounded by binder paper and pencils and unopened books on birds, immobilized by the hugeness of the task ahead. Then my father sat down beside him, put his arm around my brother’s shoulder, and said, ‘bird by bird, buddy. Just take it bird by bird.’5
This advice always stays close to my heart when I’m staring down the seemingly unscalable mountain of work that stands in front of me. It also always reminds me of a story my high school football coach once told our team: as the legend goes, back when he played football at the University of Northern Iowa, he and another lineman were running sprints. At one point, they had 16 left to do. Looking at the other lineman with a face full of doubt, my coach voiced concern regarding his ability to do 16 more. Staring sternly back at my coach, the other lineman responded: “you don’t have to do 16 more; you just have to do one more.” So one more they did. 16 times over. Until the workout was complete.
Just like you complete a report on birds one bird at a time and complete a workout one rep at a time, you eat an elephant one bite at a time and climb a mountain one step at a time. So too is it with books. You write them one word at a time.
At the end of this process, you’ll emerge with a rough draft. In terms of time, for me, this typically means I am slightly less than halfway done (see editing / proofreading below).
(D) Be Prepared to Battle Resistance at Every Stage
Just like I’ll return to the wisdom of Lamott when in the early stages of writing, I’ll usually re-read Steven Pressfield’s War of Art to prepare for a battle with Resistance (typically at the first sign of being discouraged with how things are progressing).
The writing process, like all creative endeavors, is a question of who can endure the ups and downs. Typically, the endeavor starts with all sorts of enthusiasm before passing into something called the Valley of Disappointment (read about that in On Creative Endurance), where the initial energy of a new enterprise has worn off and you’re stuck with the mundane work. The below graphic shows something of the peaks and valleys you must be prepared to persist through in the creative process.
In the lows points, you’ll meet what Pressfield has famously coined as Resistance:
What is Resistance? It’s our own tendency—yours and mine and everyone’s—to yield to procrastination, self-doubt, fear, impatience, self-inflation, self-denigration, distraction, laziness, arrogance, complacency, and perfectionism. It’s our inability to focus, our incapacity to press on through adversity. It’s our terror of finishing and exposing our work to the judgment of the marketplace. It’s fear of failure. It’s fear of success. Fear of humiliation. Fear of destitution. It’s our inability to defer gratification, to acquire and act with self-discipline, self-validation, and self-reinforcement. Resistance is our tendency to self-sabotage, fail to start, and fail to finish.6
Resistance is a force you’re going to face every day you wake up to write so you better get familiar with it. Some days it’s going to swing harder than others. And it tends to get strongest just when you’re about to finish.
The way to beat it? Just keep showing up until the job is done. As many days of making little to no progress as it takes. Eventually, the walls will fall and the work will come together. But you have to keep showing up and chipping away.
(2) The (Self) Publishing Process
Once the book is written, it’s time to start thinking about how to go about getting this thing out into the world. In a prior world, there were really only two options: find a traditional publisher or try to source your own printers and market your book on your personal social channels. Needless to say, this prior world made it very difficult for anyone wanting to self-publish on their own to produce something that would be high quality and taken seriously.
But with the rise of platforms like Amazon KDP, the process of self-publishing is now easier than ever and slowly becoming (in my opinion) the preferred method of publishing for many creators. Eventually, I will write a longer article on this subject, specifically, but for now I want to give you just the essentials.
(A) The Traditional vs. Self-Publishing Debate
The first decision you need to make is whether to try and find a traditional publisher or self-publish. As someone who has chosen to go the self-publishing route, my take here is obviously biased. After hearing Hugh Howey tackle the topic on Knowledge Project four years ago, I knew self-publishing was the direction I wanted to go (especially because I was quite certain it would take way too long to find a publisher, if I ever did, and I wasn’t willing to wait that long to start publishing).
But before we dive into the elements of self-publishing, I’ll give you a little color on why I chose this path. Others (Hugh Howey, Scribe, Paul Millerd ) have made a much more extensive case as to why self-publishing is the way—I’m just going to hit the high points.
With traditional publishing, if you manage to emerge from the time-intensive process of finding a publisher, you’ll find yourself with an offer: accept an advance (typically $5K - $50K for a first-time author; sometimes as high as $500K for folks like Ryan Holiday) in exchange for the rights and royalties associated with sales of the book and some assistance marketing and placing your book in stores.
With self-publishing, you keep the rights and the royalties (excepting any nominal percent shared with the platform you use to sell) and are on your own when it comes to marketing and distribution.
That’s effectively the difference between the two. And at risk of straw-manning the case for traditional publishing, it seems to only make sense for the top 1% of the writing population: celebrities, athletes, politicians, and professional writers interested in status, best-seller lists, or the up-front money. For everyone else—entrepreneurs, coaches, aspiring creatives, professionals, and everyone else who just wants to release a book—self-publishing seems to make more sense for a whole host of reasons (summarized in the table below).
(B) Elements
Assuming you choose self-publishing, there are a few elements you’ll want to address before your book goes live. (If you pick traditional, I’ll assume you have good reasons for doing so and you have my well wishes—but know the rest of this article is basically worthless to you.)
(i) Writing (Free*)
This one is obvious. But it’s worth including. The best marketing tool is a good book. One that others feel good about recommending to other people. It is the first and most important ingredient of your book and the easiest to procrastinate. Don’t bother spending a bunch of time figuring out all the other details of the other elements until this element is well underway (or completed).
(ii) Editing / Proofreading ($1K - $3K)
This is where the real work begins. After my first draft, I typically take a pass at editing myself (which is a brutal, but beautiful, process that ends up with me re-writing many sections and takes just as long, if not longer, than the drafting process).
From there, I send off to a “professional editor.” I’ve had success using Fiverr for this purpose. Note that there are four different types of editors: (1) manuscript critique (high-level feedback on the flow and structure); (2) line editors (comprehensive edit looking at style and language); (3) copyeditors (reviews for technical flaws and grammatical issues); and (4) proofreaders (looks at the final copy for formatting issues or obvious errors). I made the mistake of only getting a copyedit (and no beta readers) on my first book; from here on out, I will be including line editing and getting feedback from beta readers.
(iii) Book Cover Design ($250 - $500)
You can do a design contest through 99designs or find someone (like I did for both books) on Fiverr. After trying a few folks on Fiverr, one thing I’ve learned is that you want to take the time to: (1) find 5-6 pictures or book covers for inspiration; and (2) describe in as much detail as possible what you’re looking for. The times I’ve included clear instructions, results have been great; the times I’ve given more creative freedom and less-detailed instructions, the work product suffered.
(iv) Book Formatting ($100 - 200)
There are two things you’ll have to format: the book cover and the interior. Typically, the person that designs your book cover will format the cover consistent with whatever platform you plan to publish on (in my case, I make sure that the designer I select will deliver dimensions that work on Amazon KDP).
For the interior formatting, I know people that have done it themselves using something like Reedsy. But after attempting, I caved and hired someone through Fiverr for a couple of hundred bucks to do the two formats I needed: paperback and Kindle. (Like my advice above, you’ll want to ensure the person you hire can format in a way that’s compatible with the platform you’re publishing on.)
(v) Other
Much of the above has assumed Amazon KDP as the publishing platform, but there are, of course, other options (like IngramSpark). Within Amazon KDP, eventually you’ll have to decide how to price your book and whether to enroll in something called KDP Select and, regardless of the platform, you’ll also need to consider things like: ISBNs, keywords, book descriptions, metadata, etc.). Eventually I will do an article covering all of these items in detail, but for now, just know that these considerations wait for you at the end of the process.
(vi) Distribution / Marketing ($0 - Infinity)
In full transparency, this is one area I’m still painfully deficient in. After I published my first book, I only really made a few haphazard efforts to market: I did a small book launch party with close friends, made a social media and a website (like all the guides tell you to), posted about it a few times, and paid $100 to someone of Fiverr to pepper my book into a bunch of philosophy-related Facebook pages. Needless to say, the results were as weak as my efforts.
So this go around, I’m choosing to focus on a more intentional marketing effort which has and will involve: (1) building this newsletter; (2) going on podcasts; (3) remodeling my website; (4) seeding my book in the community by gifting to friends; (5) building a Twitter presence; and (6) tapping other writers (like
) for their wisdom and guidance. Stay tuned for the fruits of these labors.(3) Why You Should Write a Book (Even if You Lose Money)
Writing books (especially at the beginning) is probably going to end up costing you more money than it makes (especially if you put a minimum hourly rate on the time it takes you to write the thing). Of course, there are exceptions like
— people who are extraordinarily talented and have an existing audience to leverage. But that’s not most of us. The 2018 survey published by The Authors Guild found that “[m]edian incomes of all published authors who were surveyed—including part-time, full-time, traditionally published, self-published, and hybrid-published authors—for all writing-related activities was $6,080.” That’s the median.And first-time authors usually fall below that median. Take my first book, for example. I published it in March 2022. A year and a half later, I’ve sold 233 copies.
Royalties-wise, that equates to $474.62.
My out-of-pocket costs to get the book out (cover design, editor, formatter) was ~$1.5K. (I opted for a grammar-only editor on the first book, which was about half the price of the editor I’m using on the second book.) Say I price in a minimum opportunity cost for the ~1,000 hours I spent on it at $10/hr., that adds another $10,000. That means we’re looking at about $11,500 into the book and only $474.62 back (a loss of ~$11,000). Not exactly a great return on investment… IF you’re looking at it purely from a short-term monetary perspective.
But it was also the most rewarding thing I’ve ever done and you can’t put a price on that. The reward was the work. The treasure was who I became in the process. There is no substitute for accelerated growth that occurs during the period of intense self-examination required to give birth to a book. There is no better way to invest in and bet on yourself over the long term.
It is, without exception, the most meaningful thing I’ve ever done.
To me, that makes it priceless.
C.S. Lewis, Reflections on the Psalms.
The Dunning-Kruger effect is a cognitive bias showing the tendency of people with low ability, expertise, or experience regarding a type of task or area of knowledge tend to overestimate their ability or knowledge.
Impostor syndrome is a psychological occurrence where people doubt their skills or talents and have an internalized fear of being exposed as frauds.
Anne Lamott, Bird by Bird, p. 17.
Anne Lamott, Bird by Bird, p. 18.
Steven Pressfield, Put Your Ass (Where Your Heart Wants to Be), Note to Reader.
Thanks for sharing—this was really timely as I heard the FS <> Hugh Howey podcast for the first time this week and it got me really excited about self-publishing. I'll be revisiting this post as I go through the process 🙏🏻