Answering Some Q&A About Writing, The Book & More
September 29th, 2024: Greetings from Austin! The audiobook is locked and (up)loaded and should be available this week. I do have a few codes I can give out on audible so if you want to listen and leave an early review, let me know!
October 1st - Digital Launch Party: I’m hosting an online launch party this Tuesday, with special Guest Khe Hy (and maybe others). Join me!
In-Person Launch: If you are around in Austin mid-october and want to join the IRL book launch, send me a note!
If you haven’t grabbed it yet:
Read it already? Feel free to rate or share on Goodreads
#1 Some Q&A About This Book & The Process
#1 How did your process compare to Pathless?
For the first three months of writing The Pathless Path, I was still calling it an “ebook.” I don’t think I had a sense of the overall project until 7-8 months into the project when I finally finished a really good draft.
With this book, I had a good sense of how the project should feel. This was a useful “anchor” throughout the writing. I could remind myself at the beginning: “This is the part where I am far too confident about it being almost ready.” Then later: “Ah yes, this is the part where I have complete doubts about everything,” or “Oh yes this is the same sense of flow I found in my first book.”
The biggest difference was that to finish this book, I needed to design my writing around the new addition to my family, our daughter. In writing the first book, I wrote whenever I wanted. That suited me. I don’t like schedules and since I like writing, it was easy to drop in whenever I felt called to do it. With this book, I had to be much more disciplined. I write about this in Chapter 8, “Solve The Puzzle of Good Work,” where I had to completely reorient my life about 9 months ago to reconnect with writing once again.
One thing that’s remained consistent is my delusional optimism. With my first book I thought I was “one month away” from finishing it for about six months. Again, in March, I was writing, “I plan to release it sometime in April or May but I’m playing with some titles.” 😂
Perhaps this optimism is helpful, helping me get through the moments of doubt that inevitably occur in a project like this. But I should probably try to be a little more realistic moving forward.
#2 How did you arrive at closing the title/subtitle?
Well if you go back to that same post in March, I’m playing with the following titles:
Post-Hustle: My Accidental Quest For Good Work
Hardly Working: How I Lost My Edge & Found Good Work
The Search for Good Work: subtitle tbd
You Don’t Have To Grind: Finding Good Work & Embracing Healthy Ambition
Losing My Edge: The Art of Working Less & Finding Good Work
In the comments, several people resonated with the phrase “Good Work.”
From there, I was playing with:
The Joy of Good Work
The Search for Good Work
The Journey of Good Work
But in testing them, people suggested again that “Good Work” was powerful by itself. So I simplified it down to that.
The subtitle started as “The Most Ambitious Thing You Can Do,” which was a phrase I wanted to work into the book (which I did) but it didn’t seem to connect with good work.
Instead, I stumbled into “Reclaiming Your Inner Ambition,” which was a bit more direct about what the intention of the book was and also pointed to the personal storytelling I’d be doing.
Most of all, it just felt right, so I went with it.
#3 How did the process of this book differ (from a practical standpoint but also any differences in the type of book you were trying to write, and how the experience felt different from #1 to #2)
I felt more confident “doing a book” and that enabled me to take more creative risks.
With The Pathless Path’s success, I also felt as if this second book was a way to move away from the formula that worked in that book. Just like some singers do with follow-on albums, I hope to lose some readers and also find some new ones. The style is different, the writing is more personal, and I had a little more fun with the format of the book. I wrote about seven things I tried here:
#4 What creative depths or edges were you able to access as a writer this time that may have been inaccessible last time? How did you think about your audience this time vs last time while writing?
I pushed myself to become a much better storyteller in this book and to lean much more in the direction of prose rather than as a synthesizer/observer which is more the energy of my first book.
Many passages took a long time to rewrite and since it’s based on my own life, I needed to plunge into the depths of my inner world searching for the memories and experiences that feel “true” and convey what I am trying to say.
Which is intense. At many points, I’d be sitting at my laptop with my eyes closed trying to time travel back to an experience, and overcome with emotion. I still can’t write or talk about the experience of landing on my intro in Kenting (Chapter 6) without tearing up.
One powerful experience came from taking the Ultraspeaking Creator Cohort back in March (which I wrote about here).
Participating in a game they call the “Accordion,” I was trying to work through what I was trying to say about ambition. In it, they do this “accordion” game in which you say the idea in 2 minutes, then 1 minute, 30 seconds, and then 15 seconds. As I simplified my message something else emerged. I needed to talk about the starting point of everything. This led to me writing about the scene in Da’An Forest Park in Chapter 1, which wasn’t about ambition at all.
I’ve since used that technique to help me figure out what I’m really trying to say, the message behind the message.
#5 What was the moment that you decided to write this book? Or when did you decide that you could not, not write this book?
I struggled for most of 2023 tinkering with a draft I was calling “The creator game” at one point and then before I abandoned it, “Experiments In Living.”
I did enjoy writing it but never had a strong feeling like I was headed toward a destination that felt like a finished product. It just felt like an ever-growing document.
In January 2024, I took a trip to Boulder. I was visiting my friends Jonny and Kelly. It was also my first solo trip after having Michelle. During that trip, I reconnected with the “writer mode” Paul that had so effortlessly been at the wheel before I became a father.
In several writing sessions over three days, I started to feel a spark and excitement, like I was heading toward the end of another book again. It felt great. On a walk with Jonny on the side of the mountains, I was filled with passion. I was telling him how much I had struggled with my work over the previous year. I knew what I had to do: I had to go deeper with the personal storytelling. That was the edge I pushed in the first book and it was the edge I wanted to push again.
When I came back to Austin, I had this feeling that the book was now inevitable. I closed the previous draft, started a new one, loosely titled “Relationship to Work” and just let it rip.
I rode that wave of energy for several months and it helped me deepen my commitment to writing, reminding me why I love being on this path. (I detail the reorientation much more in Chapter 8).
#6 I’m also curious about the process—how did you decide the direction of the book, what to include and where to draw the line, how to build it up, and did you write with a specific reader in mind?
I mostly write for myself and if I am writing for any kind of reader, it is the people who have read my writing and reached out over the years.
I don’t write with any intention to please a mass audience or to “convince” anyone to shift their perspective. I also don’t have any general aims at “impact” or however one might measure such a thing.
In my head, I’m writing for people like me, hyper-curious about different ways of seeing the world and who want to keep asking “Why?" like we are children once again.
#6A: Curious about your process as a parent: Do you usually know what you want to write about and then you do it when you have time? Or do you also not know sometimes what you’re going to write about once you have time?
#6B: What did the process of ‘deciding what to write about’ look like?
I think I can answer both of these the same way: I haven’t had a shortage of stuff to write about in years.
I think there is probably a point you reach when you’ve consumed enough information and also created enough that you start thinking about things that you want to explore in writing form all the time.
If anything, after becoming a parent I’ve struggled less with this because I simply have less time.
This has helped me be much more disciplined about pulling Google Docs open and starting to write as soon as possible.
For most of the year, I wrote in three three-hour writing blocks in coworking rooms at my apartment complex or cafes. As soon as I woke up, I’d grab my bike, head out, and start writing as soon as possible.
After a few weeks of dropping into this rhythm, these writing blocks became things I looked forward to (and started to reinforce what the book was all about).
And really, the topic I was writing about in this book, my connection to work, was very narrow. It was a good filter for what to cover but also expansive in terms of how I could explore it.
I think this is why I like writing about work. It touches everything!
#7 How did I grow as a writer and thinker during the process of writing this book?
I think my narrative writing has improved, though I still feel like a beginner. I think I have a better handle on what it takes to bring a scene alive, how to slow or speed things up, and how to bring forth emotions in text. I also think I got a bit looser with myself and was able to be a little funnier in this book.
As a “thinker” or someone generating original ideas, I think I’ve probably become a little less generative, though I feel it starting to come back after finishing this book.
While writing the book I was locked in book mode and my newsletter writing probably suffered, which has always been the place I like to play with ideas a bit more. While I’ve had many great guest essays and some interesting ideas, I have probably had fewer bangers or original ideas than in years past.
I still don’t quite know how to balance it all but I do intend to take an intentional break from book writing for a few months, so watch this space!
#8 What parts did you do by yourself and what parts did you get help with? eg cover design, formatting, prep ebook files etc
What I do by myself:
Writing
Rewriting
Structural editing and overall vision/themes
Formatting & interior design (I use vellum)
From others:
Cover design (though I had to edit some stuff myself in Adobe)
Copy Editing (big hands-on effort from my editor)
Some beta reading & developmental feedback (credit to
and especially) and others who read drafts and gave thoughts
#9 What did it cost?
Overall it is pretty simple:
My time
Copy Editing ($4k)
Other editing & coaching ($500)
Cover Design ($1575 split between multiple people)
So about $6k overall costs. Then gifting books so far has been about $1-2k.
I will likely break even in about a month.
#2 Built My Book Site This Week
I launched a simple book site this week. It’s clean, simple and has a nice testimonial section (you can add yours), has a free copy of the intro, and has this fancy “hit B to buy now” button I copied from Ali Abdaal’s book site:
The cool thing was how quickly I got this up and running. In past attempts at setting up new landing pages, I would get stuck on some CSS issues. Not this time. I just took screenshots, dumped them into ChatGPT, and instantly solved them. I even created this “Press B” button and also the corresponding “click to buy” version on mobile in less than twenty minutes.
Solopreneur win.
Hey! Thanks for reading…
I am not sure how you ended up here but might have stumbled upon me through my writing or podcasting on our relationship to work, a topic that has interested me for years.
If you don’t enjoy the writing, I strongly encourage you to unsubscribe below. There’s so much good stuff on the internet!! A reminder: I don’t check unsubscribe alerts and never look at my subscriber list. So if you feel like unsubscribing, you can do so below.
But if you do want to stick around:
If you’d like to meet others on “pathless paths”, you can join The Pathless Path Community
Buy or listen to my books, The Pathless Path and Good Work. If you’d like to do a bulk order you can do that here for a discount.
You can buy pathless path swag like a hat or shirt here
Subscribe to my podcast and leave a review.
Home Swapping: We’ll likely be using Kindred a bit this winter. It’s a pretty cool home-swapping alternative to Airbnb. If you want to join, use my signup code.
5% Savings: Use this link to get 5% on your savings on Wealthfront and increase your runway on your pathless path
Affiliates: In addition, I recommend all of the following services: Ali Abdaal’s YouTube Course, Collective for setting up an S-Corp in the US (recommended >$60k revenue), Riverside.fm for HD podcasting, Transistor for podcast hosting, Podia or Teachable for courses, Skystra for WordPress Hosting, and Circle for running a community.
Submissions: Want to share your journey with my audience? I accept drafts for submission.