In December 2020, while living in Mexico, I decided I would write a book. 

It had been a thought lingering in my mind for quite a while.  It wasn’t that I desired to be an author or someone that had written a book but really just something that I assumed would happen if my love of writing did not dwindle away.  

The first time I took the idea of writing a book seriously was after reading Amy McMillen’s Reclaiming Control in the summer of 2020.  Her book was powerful.  I finished it in less than 24 hours and while her story was unique and different it gave me the feeling that I had a beautiful conversation with a friend who saw the world in a similar way.  I told her in a conversation that I wished there were 100 more books just like it.  When I told her that, I knew that I would have to walk the walk.

My Writing Journey Started Ten Years Ago

The first time someone told me I should write a book was in 2012 when I was sharing my struggles with Lyme disease.  I had decided to write because I was in a bad place and was really struggling to understand what was happening to me or how to explain it to others.  I tried to inject humor and playfulness into otherwise depressing posts about me not knowing if I’d ever get better.  When people told me they loved my writing, I didn’t really think anything of it.  All I cared about at the time was resuming my career.  

Looking back, however, that moment is just one of many throughout my life where writing seems to appear.  In high school, I had a ton of fun writing an article about five of my friends and me who drove minivans.  I argued that we were victims of our mothers, all of whom had decided to upgrade to cooler crossover SUV vehicles that were emerging.  In college, I wrote a satirical essay about my friend Martha and her time as a safety patrol officer in her high school.  There was no point to the article other than I thought it would be a ton of fun to write.  It was.

After college, I dabbled blogging on Tumblr, writing reflections on leaving New England for the first time and starting my career in Cincinnati.  I wrote all sorts of stuff which if I looked back now would likely be embarrassing and childish but I was writing. Consistently.  In business school, I kept a student blog about the experience, and after school is when I started writing about my health challenges.  After I recovered I wrote increasingly in public – first on Quora, and then on Medium, LinkedIn, and then on my own sites Careers With Paul, Boundless, and StrategyU.

@pmillerd From blogger to book. Just a casual 12 year journey #books #writing #blogger #blogs #writing ♬ original sound – pmillerd

Steady writing for almost twenty years yet I never saw it as an important part of my life until the past few years

Committing To Writing As Something That Mattered

I never noticed writing as something important in my life until after I stepped away from my full-time career path.  While I wrote more than I had in the past during my first year of self-employment, something was unleashed when I moved to Taiwan in the fall of 2018.

I would make coffee in the morning and wait for the inevitable call to write. This period was absolutely delightful. Through writing, I continued to make sense of my shift from an impressive career towards the pathless path as well as the noticeable gap between this new culture and mine back home.

In those months something was unleashed – unstoppable creative energy that had been bubbling beneath the surface but never quite had the space to emerge.  That energy told me: keep writing.  I decided to commit.  I didn’t know where writing would lead me but I had a deep sense that it was going to become an important part of my life.  I came up with a rule: “write, most days.”  It was enough.  I prioritized it and notice that when I have the time and space to think and write, I’m quite content and happy with life.  When writing starts to drift out of my weekly rhythm, I know I need to make changes.  

So I wrote, most days, and for the past three years, writing has become one of the most vital parts of my life.  I also tapped into a virtuous cycle: sharing continuing to write and sharing it publicly, it made my life better.  Putting writing first helped me realize it was work I liked doing and wanted to keep doing, led to making friends and having meaningful conversations with people from all over the world, and helped cure a residual cynicism that remained from my time in the corporate world.  Eventually, it also led to the most meaningful project of my life: writing The Pathless Path.

Finding My “Conversation” – Letting Ideas Emerge

My book emerged organically from hundreds of conversations, hundreds of posts, and hundreds of days of contemplation.  There was never a goal to publish a book until the day I realized it was time.

That time was somewhere in November of 2020 and it was a result of three key things happening.

First, in 2020, millions of people suddenly had existential crises about work at the same time. Having been writing about this kind of experience for several years, this led to a sharp uptick in my interest in my writing.  I had been casually doing no-agenda “curiosity conversations” with people from around the world for a few years at that point.  I typically had zero or one call each week.  By May of 2020, I was talking to seven or eight people a week and having many more conversations through Twitter, via my newsletter, and with friends and family.  My writing is fueled in large part by this “creative engine.”

The second was reading Amy McMillen’s book Reclaiming Control in August 2020.  I shared with her in a conversation: “wow I wish there were so many more of these kinds of books – of these sort of transitions in life.”  

That feeling was reinforced visiting Barnes & Noble that same week and seeing the highlighted autobiographies of several older white dudes:

  • Ray Dalio: Age 72 Billionaire
  • Richard Branson: Aged 71, Billionaire
  • Bill Gates, Aged 66, Billionaire
  • Steve Schwartzman, Aged 75, Billionaire

While I may have been pulled toward this kind of book when I was younger, I knew that Amy’s was likely much more useful than the stories I would find in those books.  We think we should learn from people who have “made it” but often we can learn a lot more from people dealing with the same things as us right now.   “People like us do things like this” as Seth Godin says.  I realized that I needed to turn my beliefs into action and decided that I needed to share my own story.  

The final trigger that pushed me over the hump of committing to the book was a series of three or four “curiosity conversations” I had with people from around the world in November and December of 2020.  Each of them said something to the effect of “I wish you had a book about all of this stuff and I would read it.”

In December 2020, I decided to commit to a book

I started slow, compiling many of my past blog posts into Word and trying to organize them around key themes.  I didn’t actually announce it publicly until the beginning of January when I buried it at the bottom of 10 reflections on 2020.  Here is what I said at the time:

In terms of work goals, when I reflected on 2021, StrategyU kept emerging as something to focus on but I couldn’t find a reason other than “make more money.” Given that I have enough right now, that really isn’t a good reason and generally, I’ve found that when I go against the default options, interesting things happen.

The thing that does keeps emerging is writing, so my intention for 2021 is simple:

Try to write, most days.

That’s it. And to raise the stakes, I’m announcing a scary goal, a book.

This was a scary commitment.  While being self-employed I had never spent more than a couple of months creating anything.  

My first stated deadline to publish my book was March 2021.  Looking back it’s clear that I didn’t know what I was getting into.  It’s also funny to look back and see how scared I was of just calling it a “boook”  Here’s my conception of the project from when I finally built up the courage to announce it boldly on my newsletter in January of January 2021:

This e-book will be a collection of essays from Paul, perspectives on the modern state of work, and some potential ways to think about navigating the new world of work, designing your life, and managing uncertainty while on a “pathless path.”

Here is what the initial outline looked like in January 2021

If you look at the titles and have read my book you’ll notice that many of the themes made it into the final form.  However, what you can’t see is how poorly all these pieces fit together.  One challenge with going from blog to book is that blogs are much more interconnected with other materials than a book.  A book needs to stand on its own but a blog can backlink to previous mentions of things and other references.  

It took me about a month to realize this project would be a bit more challenging than polishing a number of past essays and newsletters.

Leaning Into My Emotions & Letting It Rip

About a month into the project, I had a call with Sasha Chapin.  I was inspired to reach out after reading his Twitter bio: “I am fucking good at writing coaching.”  (Short aside here: it’s taboo to say stuff like that but as someone who really did want help with writing, this was exactly what I wanted to hear!) 

Sasha went through my initial writing and had a number of helpful suggestions but one big thing changed my conception of what the book was about.  I’ll paraphrase his advice:

“when you leaned into sharing your emotions it was powerful.  You are a really good analytical writer, which tells me you’re never going to fall into the trap of sharing too much.  Lean into that as hard as possible.  Let it rip”

I don’t know if he said let it rip exactly, but I like to think he did.  It connected with something I had read a few years earlier from the famous writer William Zinnser:

Sell yourself, and your subject will exert its own appeal. Believe in your own identity and your own opinions. Writing is an act of ego, and you might as well admit it. Use its energy to keep yourself going.

I had embraced that in 2019 but only was now starting to understand what this meant.  I knew I had to go much deeper.  Deeper into myself.  

So that’s what I did.  I gave myself time and space and tried to dig deep into how it really felt along the way: going from good student to enthusiastic prestige chase, landing my dream job at 23, losing my grandfather, and having everything I thought I wanted taken from me, as I was forced to stop working and take time to recover due to a health crisis. 

As I leaned into these experiences, I learned more about myself and my writing became better.  I have always been a good technical writer but this opened me up to new ways of sharing what I was trying to say.  It also helped me understand what people mean by “show, don’t tell.”

I realized that the book I was writing was much more of a personal story than one where I had any clear answers, how-to’s, or best practices.  I wasn’t going to tell people what the future of work was going to look like, I was simply going to share how I was thinking about it in my own life based on where I came from and where I want to go.

Seeking a Publisher To Save Me (May to July)

Around May and June, I was feeling pretty good about the shape of the book.  It had two clear parts: my personal story (in much more depth by then), and my take on an alternative to our default scripts: the “pathless path.”

Despite feeling good about it, I wasn’t sure how I’d get it to something I’d call a “book.”  The path from there to the finish line felt extremely uncertain.  This is when I started looking for someone to save me.  

I reached out to a few indie publishers to see if they would work with me.  In my head, I wanted to believe that these people using the word “publisher” would be able to give me a magical formula that would erase my uncertainty about how to finish the book.  What I heard from them instead was that I was on the right path and the decisions they might help with were ones I would need to make anyway.  

This didn’t stop me from searching for a savior.  Based on a recommendation from another friend, I checked out a company called New Degree Press.  They allow you to submit your manuscript for admittance into their “Creators Program.”  This is a five-month program for people that have a written manuscript.  

I used their requirement of a manuscript as a chance to push hard for two weeks towards my first official “draft” and then submitted it.  When I submitted it, I thought that it was going to be a very hard thing to get into and that if I was approved, it was likely a really good opportunity for me.

In the four weeks, it took them to respond, however, I realized from reviews that they were not what I was hoping for.  They seemed to accept most of the books that were submitted and many people found their sales tactics and later support less than impressive.  As my interest was fading, I received an email that I was accepted.

In a call with Here’s a preview of the costs of their program.  For comparison, my total costs (I’ll break this down later) were about $5,000 to publish a paperback and hardcover and I did it on my own timeline and own terms.

A call with the CEO confirmed that this was not the program for me.  In what I later realized was likely one of many back-to-back sales calls, he was much more focused on getting me to commit to the program than talking about why I was writing the book.  On top of this, their approach to book sales stressed me out – it focused on breaking even by charging $39 in the pre-sale and trying to sell several hundred before launch.  

While their service is likely a good fit for people that don’t like figuring things out on their own, the experience was a reminder that was exactly what I like doing.  

Thus, there was only one path forward – to do it on my own, on my terms.

Going On My Own & Beta Readers (Aug – Sep)

I kept writing and editing for another month and when I was feeling good about another “draft” version.  The thing about taking your own path with self-publishing is that at least the first time you do it, you have no idea what you are doing.  I was telling people that I was about 90% done at this point.  The reality was that in terms of total time editing and writing I was likely closer to 60-70% done.

This is when I decided to ask friends for help.  I transferred my book from Microsoft Word to google docs and asked several people for feedback.  The majority of the feedback came from four incredibly generous people:

  • Ranjit – someone who has taken a similar “leap” out of law
  • Oshan – a fellow history of work ned
  • Valerie – an overall curious human who loves reading
  • Maria – a former consultant who has been following my journey

I asked them to follow a simple system as they read my book in google docs:

  • If they liked a certain part, highlight it and put +1
  • If they were confused, tell me
  • If they wanted more, tell me that too

This really helped me understand which parts were resonating with people.  It also was the first time I started to get real feedback from this project – they were all really excited about the book and encouraged me to keep going.

Editing, Round 1 & More Magic From Sasha (Sep – Oct)

After I decided to finish the book on my own, it helped me level up my own seriousness about the project.  I had shifted away from thinking about it as a “collection of essays” and an “ebook” towards a real book, one I would be proud to ship.  

I also realized that outside feedback would be helpful.  I started looking for editors.

With some initial searching, I landed upon John Adamus, who runs a site called The Writer Next door.  After an initial conversation, he seemed exciting about my book and I ended up hiring him to do what is called a “developmental edit.”  This meant he would go through the text and call out things that don’t make sense, make obvious tweaks to mistakes, and try to make broad suggestions about the overall book flow.

I gave him access to the same google doc I had sent to my beta readers and told him the only thing I wanted him to pay attention to was where anyone put “+1.”  I wanted to keep all those parts.  

He went through the book pretty quickly and gave me a lot of good feedback.  He charged me per chapter – I think I paid him about $100 for each chapter, so about $1000.  After the beta-reader feedback and his, I realized a few things:

  • Someone else who had read a lot of books was telling me it was good enough to publish
  • I had done a better job of structuring the content than I expected (something I’ll get to in a second)

Despite this, something still felt off.  I knew the book was good but I still wanted to push it that extra distance to attempt to make it great – I wanted to pour my heart and soul into this thing.  

This is when I called Sasha again.  

He skimmed the book again and somehow conjured up the five things I needed to hear.

First, the best reason to find someone like Sasha in your corner is that they’ll tell you something like this: “The book is in really good shape, you should be proud of it.”  I think most of us underestimate how powerful someone else believing in us can be.  This comment from Sasha made me feel good and it made me motivated to keep pushing. 

He also gave me four powerful suggestions:

  1. Trim personal history 10%: “Your personal history is really great, but I think it could be compressed a little bit…in terms of the proportion of the book, it could be shortened.”
  2. Telling people what the book was about: He thought it would be good to say something like “This story is not a how-to guide but instead urging people towards a place of individual experimentation.”  This was really powerful and a lot of the feedback from the book mentioned that they LOVED how it wasn’t a “how-to” book
  3. Adding an intro to the work chapter: “Your chapter three about work was good, but it was a bit abrupt.”  In chapter three I take a detour from the story into a deep dive into the history of work.  With his advice, I added a short intro to the chapter and then tied the content a little more into my own story to make it feel natural.
  4. A better closing! He said, “Although you aren’t giving a “how-to guide” the end of the book is an opportunity to “ham it up” and give a rousing speech about what to do next.”  My ending was very light when I talked with him and with his support, I added a little rah-rah and built out a deeper list of ten things people could do.

I’ve always been the type of person that is hungry for feedback, especially from people that know what they are talking about.  As soon as I listened to his voice memo with these ideas, I had the sense that Sasha had magic powers.  He was able to turn my vague discontent with the book into four specific things that I knew I needed to address right away..

After this, I worked non-stop for a week or two, editing and rewriting almost eight hours a day.  This is also why I think if I were to do this again I would be a lot more intentional about finding professional writing coaching and/or editing help sooner in the process.  If you can find the people that can identify areas that you can improve that are also aligned with where you see the book going, it is priceless.  

Inspired by Sasha’s confidence in my book, I was also starting to feel better about finishing the book.  

Yet deep down I still knew I hadn’t written the best book possible.  So I started searching for another editor.

Getting To The Finish Line With Paula (October – Jan)

The downside of doing things on your own the first time is that you basically learn by trying things out and muddling through things you don’t know how to do.  For me, I see this as vital to my journey.  If I can figure out how to do things, I become a lot more confident about doing those things in the future as well as being able to help others (which is fun for me!).  

John’s initial edits were great but after working with him I felt like I needed someone that wanted to be a little more hands-on and work with me in a more dynamic way.  Someone that could give me advice on the overall structure and flow of the document but also someone that saw my vision believed in it and was comfortable pushing me outside of my comfort zone.  

This is when I found Paula Trucks-Pape and I am so grateful that I did.

When I say I “found her” – I really mean I started searching through my email.  I had remembered that a couple of newsletter readers had offered editing support throughout the year as I was talking about writing the book.  One of those was Paula.  I quickly shot her a note, we jumped on a video call, and I knew she was exactly what I had been looking for.

I hired her on the spot and she started diving into my book.  Lucky for me, Paula has been on her own pathless path, working as a freelancer for many years and living abroad in Germany.  My vision and story resonated with her and she even emailed me at one point and said she wanted to go “all-in” on the book and didn’t care about keeping track of her time.  

This, of course, was a bit of good luck on my side.  Looking back, I realize I should have put a lot more thought (and budgeting more money) into finding an editor sooner in the process.  I don’t think it was necessary for the first few months but I could have used an editor as soon as I had that first draft version (about 45k words when I submitted it to New Degree Press.)

Paula helped me with a number of things:

  • Making sure the timeline of events was easy to follow throughout the book
  • Helping me simplify some of my writing and ideas
  • Simplifying several of the mini-chapters from 2-3 ideas to one clear idea 

I worked closely with Paula for all of November and December and by the beginning of January she had handed off her final edit.

Designing The Cover

Designing a cover for a book is another thing that comes without a roadmap.  Pretty much everything with a book starts out the same.  You ask “how do I do this?”  You google around and get 10-15 ideas and a bunch of marketing trying to convince you to do a certain thing.  Then you ask people who have done the thing and they each give you a slightly different response.  Eventually, you realize you have to just try stuff and figure it out.

I had helped run a 99designs contest for a logo for a company as a consultant a few years back and decided it might be fun to do a contest for my book cover.  At a minimum, it would help generate a lot of ideas.

This more or less ended in disappointment.  There were a lot of interesting submissions, but almost all of them were not quite right.  Here is one hilarious submission that is too good not to share:

Fun!

Here is a sample of some of the better covers that I selected as “finalists.”

While they were the best of the bunch and some people really liked them, I toiled for a week or so not happy with the outcome of the contest.  Eventually, I trusted my gut and decided to consider the contest a failure.

One thing I didn’t realize when doing a contest is that you have to pay a lot more for the “top-level” designers to participate.  I mostly only got submissions from “entry-level” designers – meaning they likely didn’t have much background in design.  

On someone’s suggestion, I decided to hire a specific designer on 99 designs.  I went straight to top-level designers and ended up stumbling upon this guy: tintodeverano – I really liked his cover designs, hired him for about $450, and got started.  

I sent him my pitch and after a couple of days, he sent me several suggestions.  I was immediately relieved.  I liked almost all of them!

After some advice from good friend Nate Kadlac on how to think about design, colors, fonts, and book covers in general, I decided that #4 and #5 were my favorites.  They gave me a feeling that resonated with what I was trying to convey.  I asked the designer: “can I get both of those covers?”

He was happy to do that and that’s how I ended up with two covers – one for the paperback and one for the hardcover.  Why two different covers?  There is no deeper motive here – it’s just something I thought that might be fun to do.  Why not?

After some additional feedback on how to pick colors from Nate (his general advice is just to try all sorts of color shades and see how they make you feel – I used https://coolors.co/ which was very helpful), I landed on color #127EA2.  This is the final cover design:

Where I Got All The Ideas For The Book – My “Second Brain”

In the summer of 2018, I discovered Tiago Forte’s writing on building a “second brain.” I read a couple of his articles and realized that I could dramatically improve my writing by implementing his approach.

The simplest way to describe it is that it’s a note-taking step between input and output where you collect ideas. I’ve since thought a lot about my creative process and you can see what it looks like (second brain and all!) here:

If you dive into Tiago’s world you will find many hyper-productive people with incredibly detailed and advanced note-taking systems. I am not one of those people.

I embrace something you might call a “curiosity-first” approach to building a second brain. I trust my curiosity to send me in an interesting direction and depend on consistent creation to help me come back to interesting ideas and naturally connect the dots over time.

Instead of having a detailed system, all I do is automatically sync notes from many sources into a central note system (I use Roam but also had success with Evernote). I don’t spend time summarizing or organizing those notes at all. Instead, I use the search function, often triggered by a gut instinct or an impulse that a certain book or idea I’ve read in the past has something to add to what I’m already writing.

The key to all this is finding an idea worth exploring and then consuming a lot of information. For me, that topic has been working and I’ve probably read hundreds of articles and essays, 50+ books, listened to hundreds of podcasts, and talked to hundreds of people. Paired with consistent creation, this led to the natural emergence of many original and creative ideas. For example, I coined the terms Boomer Blockade, Hustle Trap, Accidental Meaning, and many more.

If you create consistently AND consume large amounts of information around a narrow set of themes, you will inevitably write yourself into your own original ideas.

Through talking to people about these ideas, and writing about them in my newsletter I became more confident about them and I started to develop a better understanding of my own personal philosophy on the modern relationship to work.

As I wrote the book, many of the blog posts and ideas were the core building blocks and starting points for going back and reviewing notes on many books, ideas, and articles that inspired me.

The process of writing a book is its magnetic force as well. Throughout the year almost everything I consumed seemed to have something relevant to the book. I was constantly taking notes and leaving comments to myself in Apple notes to look at later while writing.

Balancing Structuring & Research – Shifting Between Bottom-Up and Top-Down thinking

The approach I used in writing a book was very similar to how I worked on projects while I was working in the consulting industry.  I thought this would be worth sharing because part of what made this so enjoyable as a year-long project was that it felt very similar to working on an ambiguous business problem – one where you don’t know the answer until diving into the process.

In consulting, you are usually focused on solving a problem.  You often spend weeks defining the problem and fine-tuning this over and over again with the client.  After that, you develop a set of hypotheses and start testing out all sorts of different questions.  This kickstarts a process between high-level questions and bottom-up research and analysis.  This back and forth is something that is incredibly uncomfortable when you first learn it and if you don’t find some joy in this way of working, you end up leaving consulting pretty quickly.  

The more projects you work on, the more comfortable you become with this back and forth.  You learn to see the uncertainty about where the project is headed as a normal thing and start to trust the process – mostly iteration, getting loads of feedback, and then shifting between research rabbit holes and stepping back to restructure the deck.  Here’s how I think about this kind of process in consulting:

Writing a book is essentially the same thing and being able to shift between these two modes is vital.  If I had to alter this, here’s what it might look like for writing a book:

And if I mapped it to my own experience, here are some of the key moments in my own book-writing process:

From a top-down standpoint, here is how the overall storyline and structure evolved throughout the process:

I’m leaving out a lot of detail of course, but if I were giving advice to someone thinking about writing a book I’d suggest the following:

  1. Think about the structuring of the book as an independent activity from the writing.  These are two different ways of thinking and it’s not easy to shift between them.
  2. Extended breaks from writing can be useful in thinking about the book in the top-down mode.  This is because it will help you brain shift into “diffuse mode” type thinking where you can start making connections between ideas.  Often when I was stuck, I would stop writing for a week or two and the answer would emerge.
  3. The whole process is supposed to feel frustrating.  You need to have the sense that despite making 5 rounds of edits, making an addition 15 more edits to the same section is something worth doing.  Without this, you will struggle.

From my consulting experience, I had a deep belief that more iterations, especially if you can get feedback from great people, is almost always better.  With this idea, you really can think about the process of writing a book as a process of continuous editing, tweaking, and improving.  The biggest challenge is that if you don’t have experience working in this kind of environment, the process will be really stressful and annoying the first time you are lost in the weeds without a good sense of where you will end up. 

Formatting The Text In Reedsy

Formatting the text was something I assumed would be easy that was a bit more complicated than I imagined.  It turns out that you have almost unlimited options for colors, spacing, formatting, fonts, and so on.   Luckily, a friend had recommended Reedsy, which has very limited options (only three fonts).  I like to keep things easy so I decided to go with Reedsy.  They have a very easy-to-use editor which can turn Word docs into a book-ready form.  Here is what their interface looks like:

As well as some of the formatting options they give you.

One weird thing I didn’t know about books was that most books use no spacing between paragraphs and indent each line.  If you go open a book on your shelf, it almost undoubtedly looks like this:

When I uploaded my book into Reedsy, I hated how the indents looked.  Yet when I looked around for the reasons it was that way, I couldn’t find any good explanation.  It’s just the way it is.  The spirit of my book was all about questioning defaults so naturally, I was questioning this as well.  I then polled people on Twitter:

By a margin of almost 10 to 1, people seemed to love the blocks.  Since half my audience was on Twitter, I went with blocks.  On Reedsy this meant manually going through the entire book and hitting enter before every paragraph, but I like how it came out.  Here is a comparison from my book.

Formatting the book is also something that doesn’t come with instructions.  I mostly figured this out by using a free book formatting editor (Reedsy) and looking at other books.

I’m always a fan of keeping things simple and Reedsy was perfect for helping to add constraints to the process.  

How To Figure Out A Cover Size

Walk over to your bookshelf again – start to notice how many different sizes of books there are.  If you are like me, this will be the first time you’ve noticed this.  It turns out in addition to writing a book you have to make judgments about how a book should feel, look, and be sized.

Here are the options Amazon offers for book sizes:

What the!?

Luckily, Reedsy only gives you four options:

The best way to figure out what size book you want likely depends on what you want the book to feel like.  When I did 6” x 9,” the book came out to 172 pages.  I printed a book copy on Amazon and didn’t really like how it felt.  When I did 5.5” x 8.5” it came out to 220 pages.  Holding that version felt better and it also looked more like what I thought a book should look like.

I really don’t know any way of figuring this out other than trial and error, finding books you like the feel of, and playing with your editor (like Reedsy) to see how many pages you end up with.

Rights & Ownership: Getting The ISBNs

I wanted to fully own the rights to my book and that meant buying ISBNs.  Each country has a different place to buy this but for the US, you have to go through a company called Bowker.  One thing I didn’t realize is that you need to have an ISBN for each format you produce.  This means at least five if you want EPUB, Kindle, PDF, iBook, Paperback, and Hardcover.  Then another one if you want to publish your own audiobook.

So I bought the package of 10 ISBNs for $295.

The book publishers will give you an ISBN if you don’t want to purchase your own, but they also make you sign one of those massive legal forms that never feels good.  My feeling is that the future of content still has a lot of unknown upsides and I want to own all the rights to my material for the indefinite future, not Amazon.

You will need these for the covers so that Amazon (or your designer) can add an ISBN and barcode to the final version.

Formatting The Cover

You can’t design your cover for submission until you have the ISBNs and figure out how many pages the book is and the options you are using for various publishers.  I initially launched my book with two print publishers: Amazon KDP and Ingram Spark.  They each have different requirements for covers but both have template generators you can give to a designer.

For example, here is the cover generator from Amazon

You’d think that switching from cream paper to white paper would be the same book dimension, but apparently, that is not the case!

After formatting, covers will look like this for Amazon

And like this for Ingram Spark (their cover templates are a little more complicated!)

Naming Myself Publisher!

This is a trivial thing but something that may stress you out, especially if you are insecure about not going through a formal gatekeeper or publisher.

No worries!  It turns out you can declare yourself the publisher!  

Simple, and cool.

Pre-Sales: Gumroad & Then Amazon

Where you sell your book, for how much, and when are all decisions you’ll need to make when self-publishing your book.  I’m certain that I did not take the optimal approach but I’m also not sure what the optimal approach is, there are so many options!

I pre-sold my book on Gumroad.  This let me put up a page and allowed people to support me as I shared progress throughout the year.  It was also a way to hold myself accountable.  The more people that bought it, the more excited I became.  When I launched, I had 103 people that had bought the book on Gumroad.  

One unique thing about gumroad is that it allows people to offer a give above and beyond the price.  Several people paid much more than $10 for the book (one person even paid $100!)  I reached out to all these people asking them for ideas along the way and also gifted these people multiple printed versions of the book.

I finished the book in the final week of January and had everything ready to upload.  At the time, I thought that I’d set a release date of February 1st and try to build some hype before the launch and sell more copies on Amazon.

To start this process, I uploaded the versions for the physical book on Amazon on January 13th. The next morning I woke up to the following e-mail:

Oh shit.

I had noticed there was no pre-sale option when I uploaded the book but assumed I might be able to fix it later.  I was wrong.  It turns out if you are self-publishing, you cannot pre-sell print copies, only the kindle version.

So I decided to just go ahead and leave it.

I had been planning to do some research on optimizing launches and figuring out how to hack the Amazon algorithm to boost sales but when I realized it was already live, I was too excited to wait.

I don’t like marketing, and I don’t like pushing towards extrinsic goals, so I just had not spent much time thinking about my launch anyway.  However, I wasn’t completely naive either.  I had lots of proof (100 pre-sales, thousands of newsletter subscribers) that people were going to be interested in the topic. 

Part of the spirit of the book is about learning to trust that if you align your actions with things you actually want to do (and care about) it might lead you in an interesting direction.  I had a sense when writing this book that it was either going to resonate with people or not and if it resonated it was going to be the kind of book that spread slowly and consistently over a long period of time.  The challenge with this belief is just being patient and trusting the process.  Trusting the process can feel like ineptitude.  Luckily, with the launch anyway, my own ineptitude forced me to move forward.

I did pre-sell the kindle book for a few days and ended up pre-selling about 53 copies of the Kindle edition.  I officially launched all the versions on Amazon, IngramSpark, and Gumroad on July 16th.

It took a while longer for me to get everything set up on Ingram Spark and my first sales on those platforms did not happen until the second week. 

After the first week, counting pre-sales, I sold about 200 books which was pretty exciting! 

“People are buying my book, wow!”

Amazon has been the biggest sales channel and I’ve sold at least one book each day for the first month and a half which has been way better than I expected!  This article from 2004 seems to suggest that only 4% of books each year sell more than 1,000 copies. I’m guessing that number is a little higher with the explosion of self-publishing, but still seems to be a pretty cool accomplishment.

Here is what the sales look like in early March

Based on some shoutouts from people with big audiences, several podcasts, and other ways people found out about my book, I did pretty well on Amazon.  The kindle was the top release for multiple weeks in a few categories and at a time was close to Tim Ferriss’ 4-Hour Workweek at one point which was pretty cool.

Uploading to Apple, Google & AppSumo Later

One limit of printing books with Amazon or IngramSpark is that they don’t have coverage for lower-income countries.  What this means for people in India (which I have a decent audience) is that you can only ship printed books from the US which makes them absurdly expensive.  Luckily, I recently stumbled upon Pothi where I should be able to set my book to sell for as little as 249 rupees which is about $3.50.  This is great news!

In my rush to get set up on IngramSpark and Amazon, I forgot that since I owned the publishing rights, I could publish the ebook on any platform.  

I’ve since added my e-book version to Apple iBooks (this was hard to find but the site is http://authors.apple.com/) where I earn about $7 on every copy, and then recently to Google books (the link to do that is here: https://play.google.com/books/publish/u/0/).  I also put my book on AppSumo because Noah Kagan sent me a nice DM halfway through writing my book (link here).

Self-Publishing In India

One challenge to self-publishing is getting the books in countries people want them for prices that are reasonable in those local markets. This is likely something that publishers are good at. I received a DM from someone in India that was trying to get a printed copy of my book but only could find copies shipping from the US. The price plus shipping was more than $25. The person told me that typical prices tend to be about $5-6 max in India.

After some searching, I found a company, Pothi, that offers self-publishing in India. They sell the book on their own platform and also on Amazon.in and Flipkart. The only challenge with this was that I needed to re-format the cover (they didn’t have a good template maker) and then use another ISBN (it can’t be the same as the US version. So I did that, downloaded a new barcode from here, and uploaded the new version. By mid-march, my book should be available via Amazon for only 334 rupees (the minimum I was allowed to offer, about $4.35 USD).

How I Priced The Book

I’ll answer this one pretty quickly: I more or less looked at what other books were selling at and picked prices.  I decided on the following:

  • E-Book: $9.99
  • Paperbnack: $17.99
  • Hardcover: $24.99

The biggest challenge in pricing is the kindle version on Amazon.  If you want a higher royalty rate of 70% you have to price within 3.99 to 9.99 (hence why I picked $9.99).  You can also opt your book in for expanded distribution but you cannot sell an ebook on other platforms.  Maybe this is leaving money on the table?  To me, I’d rather have more convenience and reach more people than optimize for sales.

One nice thing about Amazon and IngramSpark is that they automatically estimate prices for different regions.  Here is what it looks like on IngramSpark and the royalties for each region:

One final pricing thing: apparently you can set library pricing on IngramSpark too – they recommend anywhere from 2-3x the ebook price, so I chose 2x the price.

It looks like my book is in a few libraries already too!

How Much Did This All Cost?

The costs of the process were pretty straightforward:

Direct Book Costs: $5,142

  • Cover: $742 ($270 for cover contest and $472 for designer)
  • Editing & Coaching: $3,900
  • IngramSpark Costs ($250)
  • ISBNs: $250

Additional Spend: Promotion & Marketing: $2,425

  • Self-purchases of about 152 books: $994
  • Sending ~200 gift copies of books around the world: $1,170
  • Advertising Experiments on Amazon: $125
  • Promotion in the Joy List Newsletter: $100
  • Instagram Ad Experiment: $36

Total spend: ~$7,567

Will I Get Rich Off This Book?

Short answer: probably not.  However, I have already broken even which means that every book I sell for the rest of my life will be profitable. This is probably one of the biggest upsides to self-publishing.  While you may get a big advance with a publisher, typically they sell your books at a discount and then only give you $2-3 per book.  

This is compared to the pricing and structure I’ve taken, where I’m getting about $8 per book.

Here’s the breakdown of my sales, royalties, and total earnings as of March 2022. 

As you can see there is a wide range of royalty rates, with IngramSpark being the lower.  Those should actually get higher because I switched the discount from 55% to 30-35%.  They suggest you have a higher discount for book stores that may want to purchase your book.  But after reading some people talking about this on Reddit, I realized that most of my existing sales are just readers buying the book on sites like Barnes & Noble and the equivalent in Australia and the UK and that I was giving money away to the company selling it rather than driving any incremental sales.  So those should jump to about $8-10 for the paperback and hardcover going forward

How I am promoting the book

While I’m not doing much traditional marketing, I am talking about the book and sharing my progress with sales – that seems to be something that has been exciting for people.  In addition, I’ve been sharing testimonials from people.  This seems to be the best way to “sell” a book.

One of the hardest things about writing a book is writing a summary of the book. I literally wrote a book because I couldn’t figure out a shorter way to say this!

Luckily, readers have shared their thoughts!

I’ve been blown away by the responses from readers and I am not lying when I say that the reception has been much more positive than I expected.

Here’s some of my favorite reader feedback:

“I could easily see this book having the cultural impact of Rolf Pott’s Vagabonding.”

“Like the 4-hour workweek but attainable”

“It’s a rare book in that it is tangentially about careers and being more focused and productive, but unlike almost every other book I have read about these topics, I finished this one and felt better about myself and my career.”

“The themes are timeless. The content is expertly written. The advice is refreshingly non-prescriptive.”

“If you have questioned your own path or a nagging lack of intention in your choices you need this book. If you have felt a gradual loss of agency in your direction you need this book. You are in the grip of an invisible script that was not written for you.” 

“The writing is fantastic – Paul’s writing is approachably poetic; a quick read that weaves together his own experience moving from a ‘default path’ overachiever to a ‘pathless path’ seeker of passion and curiosity, deep research into the history of work and collections of perspectives from years of podcasting, friendship, conferences, and meetings with other ‘alternative path’ life-livers.”

In addition to sharing on Twitter, Facebook, LinkedIn, and Instagram, I’ve also been doing a few things proactively:

  • Going on different podcasts: (used this as an excuse to reach out to some bigger name podcasts – may be some news on this soon!)
  • Gifting books to friends: Many people are excited about these ideas and/or are doing similar things. I’ve been gifting the books with

More Questions (Will update this as more come in!)

What were some fo the unexpected challenges you faced?

One interesting challenge was that I got a lot better at writing as I went on.  What this meant was that if I was working through the book in the flow of the book, the ending would be better than the beginning.  In the first few months of committing to writing, I noticed that I hated most of my previous drafts.  It was also fun to keep going back and knowing that I had improved.

Writing a book was probably the best thing I’ve ever done to improve my writing.  Highly recommend if you like writing!

How Does It Feel To Publish A Book?

I didn’t have an expectation of how I was supposed to feel when I launched my book. When people asked, I said things like “it feels good!” but to be honest it really doesn’t feel like a big deal to me. All the most exciting parts were during the writing. Small moments like tweaking a paragraph over and over again for a couple of hours and then magically finding the right words to make it work.

This book feels like a natural summary of a lot of what I’ve written about over the last five years. Instead of pointing people to a collection of blog posts, I now have something I can give to people that might be a little more helpful or inspiring.

The biggest thing I felt was free. Throughout the entire last year, I was always thinking about the book. Whether it was spotting ideas in things I read, noticing things in everyday life, doing the writing, or rounds of editing, I finally shipped the biggest creative project I’ve undertaken.

This week I’m going to be spending a ton of time reflecting on 2021 and starting to think about what comes next.


Just published! The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here



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