This tale grew in the telling…
J.R.R. Tolkien
Like Samwise Gamgee, I’m curious what happens next in my favorite stories: “And where will they live? That’s what I often wonder.” In this case the story is my own, following up and reflecting on the ten years that have passed since I published The Art Of Troubleshooting in 2014. From highs to lows to a delayed recognition (of sorts), there were unexpected twists and turns when I sent this work out into the world. For creators of all types, I also want to share my winding process and evolving definition of success.
Boredom Meets Purpose
Why did I set out to write the book? The motivation was two-fold: I felt a compulsion to share what I had learned about repair and I was seeking something to fill a void in my life. The business I had co-founded, the source of so many insights in the yet-to-be-written book, had recently been sold. Lightened of my title and authority, I’d “graduated”, but to what?
Soon, I became aware that I needed a new purpose and a way to digest the transformational experience of running a start-up amid breakneck growth. After a period of taking notes and kicking around ideas in my head, in mid-2010 I started writing The Art Of Troubleshooting; about a year later I had laid down the bulk of what I wanted to say. My initial concept was to create a small paperback of pithy wisdom, something like Sun Tzu’s The Art of War or Hazlitt’s Economics in One Lesson.
However, my original idea “grew in the telling”: a short list of topics quickly swelled to a much larger work, where finishing one chapter would prompt two more. I initially thought that most of the ideas could be covered in a few paragraphs, but when I sat down to write, I realized there was much more to say. Plus, I had to address all the situations where a reader would likely ask “What about this…?”
At that point, the book was ostensibly “complete”, but that first rough draft still seemed…very rough. Even though I wrote it, when looking over the endlessly scrolling text, it felt unwieldy and difficult to conceptualize. Words, words, words. What had I created and how would I turn it into something useful?
Blog-spiration
Completing that first draft left me depleted and a bit bored of the topic. The way forward was unexpected: by 2011, the blog format certainly wasn’t new, but the technology was just what I needed to inject much-needed enthusiasm into my stagnant writing project. As a reader of blogs, I delighted in the explosion of human self-expression that blogging tools made possible when they hit the mainstream in the aughts. Launched in 1999, sites like Blogger and LiveJournal made it possible for anyone with a web browser to serially publish their thoughts on…well, any topic under the sun. Sure, it often got pretty niche (see: Burrito Blog), but if you liked to read and wanted to hear directly from your fellow man on topics grand and obscure, it was heaven. The blogosphere fulfilled the promise of Internet version 1.0 and was a more cerebral and decentralized version of the social networks that followed, which consolidated and purified the “here’s what I think…” format into an addictive substance (Twitter and Instagram most of all, shortening our discourse to just 140 characters or a single photo).
On top of flagging motivation, another problem I had was that my theories about troubleshooting were untested: up to this point, no one besides me had read a single word. But my giant unedited word processor file didn’t seem like a good format for soliciting feedback—nobody owed me a favor big enough to read the whole thing! I needed a way to both refine what I had written and make it easier to get reactions from readers.
Poring over the massive “wall of text” I had created, with the last decade of reading blogs in the back of my mind—it clicked! The blog format would be a great way to solve my problems of process, feedback, and motivation: I would take what I had written, divide it up into article-sized pieces, then polish and publish each one serially. Along the way, I could send the individual posts to prospective reviewers and they would know exactly what I wanted them to examine. This interaction with readers would give me fuel to continue, and I hoped there would be plenty of unsolicited feedback: the comment sections of the popular blogs that I followed were chock-full of remarks (spoiler alert: the comment-a-palooza didn’t happen—if I wanted that, I should have started a blog about politics, dating advice, or dogs).
In 2011, I registered the domain name ArtOfTroubleshooting.com and hooked a blog up to it. For the next 2½ years, I would extract a chapter from the rough draft, spiff it up, then push that satisfying “publish” button. This scheme reassured me that finishing the book was simply a matter of routine.
Let’s Collab
The pressure of sharing an excerpt with the world raised the stakes: I didn’t want to waste people’s time with half-baked prose, so I would stick with a topic until it was exhausted and the words felt dead-on. Similar to what happened when I sat down to write the first draft, the blog editing process revealed adjacent topics that needed coverage. To show you how much blogging added to the book, note the word count of my original draft at around 33,000 words, but the book available today is over four times (4x) as long! At some point, I realized that this expansion had gotten out of hand and that the book had to end somewhere. It was a relief to finally draw a line in the sand and, like Picard, say: “This far, no further!”
As suspected, the book’s blog-ification provided an easy hub for collaboration. Bit by bit, I would contact a lot of people about The Art Of Troubleshooting, sending a link to a particular article that I thought was relevant to them. As opposed to dropping the entire book in their laps/inboxes, I found that people were much more likely to respond to these narrower requests for feedback. The blog format also lead to a serendipitous collaboration with a thoughtful and meticulous editor—my aunt! She subscribed to the blog’s email updates and would generously reply to each post with any typos or ambiguities found therein.
Ten Different Opinions
Shortly after starting to write, I had the suspicion that, although my time in the startup crucible had given me many insights into troubleshooting, I needed a broader perspective. My grandfather, a retired auto mechanic, was an obvious person to ask, “Does this wacky scheme for a book make sense?” We sat down to chat and his funny stories about salty customers and hard-won fixes poured out, convincing me that I was on the right track, both with my theories and the hunch to incorporate the lessons of other repairers. As my grandfather has since passed on, I’m grateful I took the time to record him talking about the ups and downs of his chosen profession—even though we were talking about cars, his humorous sense of life shone through (see: “all machine problems are human problems”).
As the scheme of transforming the proto-book into the blog wore on, I wanted to return to the interviews. When I did that first one with my grandpa, my concepts were in their infancy, so the goal was just to orient my efforts and serve as a sanity check. Now that I was further along, there was another kind of feedback I identified as crucial: what did excellent troubleshooters think of my ideas?
To find out, I conducted several more interviews with competent fixers I’d met throughout my life. Having bettered my repair ideas through the book-to-blog editing process, I was finally ready to solicit the thoughts of this select group. The results were gratifying: as suspected, the universal principles I had identified were being employed in many diverse professions, even if these great troubleshooters weren’t conscious of them or used different terminology. If you download the book, you’ll see pithy quotes from these 10 interviews sprinkled throughout the text.
Looking For A Publisher
You know how sea turtles have like a sh*t-ton of babies because most of them die on their way down to the water? Peter just wants to make sure that his money makes it to the ocean…
As the chapters piled up on the blog, I contemplated the endgame and wondered, “Should I show this to a publisher?” After all, that’s what serious writers do (correction: did). Of course, a problem quickly became apparent: how do you even talk to these people? The big publishing houses get so many submissions, I’m inclined to think they’d rather not—talk to you! It was a matter of luck that a friend happened to know a real, live publisher and put me in touch. Their catalog was tech-related and aimed at professionals, so I thought there might even be a fit with their niche.
Before I tell you what the publisher said, I want to note that going into this, I knew that a book deal was a long-shot. That’s why I was grateful to just have an expert extend a few minutes of their time to answer my publishing questions and provide honest feedback. When they declined I wasn’t shocked, but the why surprised me.
First off, I thought publishers were supremely skilled at selecting just the right titles that the public wanted. Further, if they chose your book, that must mean they really believed in it and you could expect unlimited support if it wasn’t initially well-received. My publishing contact quickly disabused me of those notions, indicating that most of the big publishers have a “venture capitalist” (VC) mentality towards the books they release. What does this mean? Well, VC firms know that there’s a significant element of chance involved in the performance of their investments. As a hedge, they spread their money among multiple startups, trying to maximize the return of their portfolio as a whole: one “unicorn” business in their stable can make the rest irrelevant (and expendable).
Apparently, many publishers operate with a similar model: they release a myriad of titles each year in the hopes that a few will make it big. Just like VCs, publishers know that they can’t possibly predict the winners, hence the shotgun approach. From the perspective of the individual author, it’s little consolation that the publisher’s catalog has produced a good result in the aggregate, especially when you find the publisher’s scarce marketing resources going to other titles that are selling better than yours.
Speaking of marketing, I also believed that publishers were pitchmen extraordinaire, skillfully touting an author’s work after locating the perfect readers. I was very surprised when my contact said that publishers were generally bad marketers, but his explanation made sense: how could they be, given the widely differing audiences for each title? Each book is a one-off, presenting a different advertising conundrum. Maybe that’s why niche publishers have a better shot at getting your book in front of interested buyers: e.g., if you only sell cookbooks, you might have a better chance at cracking that specific marketing puzzle. The flip side is that specialized publishers will be laser-focused on making sure a particular title fits their theoretical audience: if your book doesn’t mesh, they likely won’t be interested.
From this publisher’s perspective, identifying a coherent audience for The Art Of Troubleshooting was my biggest problem. For his taste, my elevator pitch was way too broad: how could they possibly create a targeted marketing campaign for a book designed to make everyone better at fixing things? For better or worse, this perceived lack of focus is inherent to a generalist approach: the whole point of the book was to describe the universal principles of repair, common across all fields and industries.
Even if I rewrote my book to appeal to a narrower audience, the final stumbling block was my non-existent “platform”. Apparently, publishers these days like it when you bring an audience with you. Having a plethora of existing followers, likes, comments, listeners, viewers, subscribers, etc. makes it easy to prove that there’s an exuberant horde just waiting for your book. Catch-22 alert: just like proving that you don’t need a bank loan makes you eligible for one, if you have a sufficiently large following to interest a publisher, you might not need a publisher. In our era of easy self-publishing, why give away so much of your royalties? A standard book deal might only pay 7.5-15%, while a platform like Amazon could get you closer to 70%.
Of course, it would have been mighty flattering to get a book deal—if offered one at the time, I probably would have taken it! However, I stopped pursuing it seriously after the problems identified by my friend-of-a-friend in the industry, and was glad to not waste my time composing hundreds of unlikely-to-be answered cover letters. In retrospect, it was all for the better: the book’s broad stance was what made it unique, but was also the thing most likely to be changed by a publisher (“Um, yeah…if you could just go ahead and tweak it to target programmers, that would be great.”). Rewritten to appeal to a narrower audience, it would have been easily forgotten. In regards to my platform, the publisher was right: there were no masses clamoring for my book. Not yet, anyway. I’m glad I retained control because it was going to take a long time for this audience to emerge.
Inconsistencies: Hobgoblins Of My Mind
Alright, self-publishing it would be, but before I could self-pour the cheap champagne I had to actually produce a final version. That was easier said than done, so let me gripe about the layout process and final editing push: I get why most authors prefer to outsource this nit-picky death march.
Before I complain about the software, I will complain about my own capabilities. The level of detail-oriented anal-retentiveness needed to keep a consistent look-and-feel in a long book is beyond frustrating. My source material was the blog articles I had published over a 2½ year period. Over this long stretch, did I always do things the same way? Nope! Of course, I wanted all the components of the book to look uniform: paragraphs, quotations, pictures, captions, citations, headers, footers, etc. I would agree on a standard (for example, picture caption text being bold italic), then have to go back over the whole book, discovering numerous inconsistencies. Worse yet, since I wanted a given blog article and its corresponding book chapter to be exactly the same, any change would have to be made in two places!
If you think my mind was buggy, you should have seen the software I was using. While Apple Pages seemed quite capable for shorter documents, at the time it wasn’t the most stable program to lay out a full-length book. As I poured in the 350+ pages of source material, with all the tables, stylized text, and high-resolution photos, it became unwieldy. Cutting and pasting from WordPress into Pages would bring in all sorts of weird artifacts that were very difficult to detect and fix.
I chose Pages because it was able to produce both an EPUB and PDF version from a single source file and, perceiving a lack of other viable options, I stuck with it for the initial release of the book. However, its fragility and the complexity of having two parallel texts meant this scheme cried out for a better long-term solution. I’ve since programmed a custom PDF generator (using wkhtmltopdf) that references the blog’s html as its source material. To fix a typo, I do it in only one place (the blog) and it automatically propagates all the way to the e-book, which is generated with just a single command. Simplicity!
(image: Library of Congress)
A Big Party, Then Crickets
There’s a permanence in the printed page, which made me nervous to commit to the seemingly irrevocable “dead tree” format. But I was very tired of the process—ready or not, it was time to publish! Thus, in May 2014 I checked off every item in my long editorial “punch list”, then wrangled a final version out of my laptop. After putting the book up for sale on the usual marketplaces, both in printed and e-reader formats, I decided it was time to celebrate with a big bash.
I placed an order for 100 books to give away, rented the Piston & Chain motorcycle clubhouse, and sent out invitations to everyone I knew. The annoying thing about organizing a party for yourself is that it’s kinda difficult to also focus on having fun. From getting the music right, to making sure that we didn’t run out of doughnut holes and shots (my chosen food & drink combo), it was an exhausting night: I understand why people hire party planners. Bringing a multi-year project to completion is bittersweet, and not the type of thing that you can process with a 5-hour blowout (although it felt good to try!).
It was tremendous to see so many people who meant so much to me in a whirlwind of an evening, then send them on their way with a copy of my efforts. Coming down from that high, in the months that followed I began to get a glimpse of what the book’s immediate impact would be: not much. I’m not sure what I was expecting, but it was a letdown to go from the big party to radio silence. But, having watched other creative projects fizzle after launch, I think my experience was typical.
Nonetheless, I wasn’t going to be ignored so easily: every day I made sure to do at least one thing to promote the book. I monitored social media for mentions of troubleshooting, bought search engine ads, wrote to anyone I thought would be remotely interested, and tried to drum up reviews. Tinkering with my pitch was both interesting and frustrating, but nothing I tried boosted sales in any meaningful way. Less than a year after the book was published, I had grown tired of my endless promotional experiments and resulting paltry sales. Feeling defeated, in February 2015 I yanked the book off all the platforms where it was for sale and wrote a blog post announcing that the e-book would be available to download for free. It’s been that way ever since.
You May Have Moved On, But The Internet Hasn’t
Supplied to the world gratis, The Art Of Troubleshooting was now liberated to find its audience, however long it took. Joining the “long tail” of other low-volume cultural artifacts, it would sit waiting like Vladimir & Estragon. I would continue to write pieces for the blog, but after a couple years I mentally put the book in the “done” category and…let it go.
Meanwhile, the Internet was slowly at work in the background… Eventually, I became aware that my site was among the top results for many repair-related queries on the major search engines. I finally had a “platform”—a reliable audience! The recurring stream of visitors from Google et al. was an unexpected yet welcome byproduct of blogging: after all, the original point of the blog was just to help me finish the book! But somewhere between the incoming links I had planted in that first wave of promotion (I would ask people to link to my site) and the mysterious blessing of the algorithm, a trickle of traffic was coming my way. Still, feedback was sparse: only 5 different people left a comment on the book’s download page between 2015 and 2018.
Fast-forward to 2019, and I sensed something special was happening when a community college instructor wrote to me and said that he was going to be using The Art Of Troubleshooting as a textbook for his class. He said that “yours is the only truly generic troubleshooting book I have found.” Receiving this message was a thrilling experience because I had lamented in “The Big Idea” that “I’ve never seen a class offered that was devoted to the topic in a general way.” I was hoping that someone would heed the call and create a course teaching broad repair principles—and they did! This was someone I had never met nor coordinated with: a beautiful moment that underscored the decentralized collaboration made possible by the Internet. Since then, I’ve received more messages from educators who have incorporated my writing into courses designed to teach generic fix-it skills.
Free, First, & Passive Are The Killer Apps
…it sure is a hell of a lot easier to just be first!
Where did I get the idea to give away the e-book? It wasn’t the first time: before putting The Art Of Troubleshooting on sale, I offered up over a thousand free digital copies as a pre-promotion. In addition to a cadre of unpaid crowdsourced editors who would catch any lingering problems, I thought this move would generate some “buzz” and lead to word-of-mouth purchases. Instead, the likely effect was to cannibalize my sales, but it was exciting to watch the download numbers go up quickly—it made me feel a sense of forward momentum!
In 2015, my decision to give the book away again was made with some mixture of pride, a sense of defeat, and idealism. I had worked so hard to write the tome, and couldn’t bear the thought it would languish in obscurity—something that seemed assured based on the meager initial sales and my inability to decipher the marketing enigma. I also believed that the repair concepts I had identified could benefit humanity, hence I reasoned that “free” would spread them the fastest. It would be nice to believe that my lucid prose was the sole catalyst for The Art Of Troubleshooting being used as a textbook, but the economist in me won’t let that stand. What actually gave the book a fighting chance for finding an audience in the crowded media landscape was its uniqueness (the first of its kind?) and the fact that it was free. Especially for educators and students: zero is the right price!
One more bit of irony: it gradually dawned on me that there was a good chance that the blog would totally eclipse the book. You see, while the book had become favorably ranked by the search engines, so too had many of the blog’s articles; these incoming visitors arrive with no effort on my part. A decade later, there’s no doubt about the winner: the blog’s pageviews are 34 times greater than the book’s downloads!
Adding It All Up
Pick a random moment in the last decade, and it’s a coin toss as to whether I’ve viewed this project as a success or failure. After the book’s release, I was operating as though it was going to be a success, doggedly promoting it to whomever would listen. Later on, I embraced failure, acknowledged that it was not going to be a bestseller, and decided to give away the e-book for free.
Whenever I was unsure about how to judge the external results, I always fell back to the standard that writing The Art Of Troubleshooting was meaningful to me. That’s why my message to struggling creators is this: if there’s a chance your work will languish in obscurity, at least make sure you get something out of it! Along the way, I was fascinated and entertained by a richly complex topic that I’ve returned to again and again. Troubleshooting has a familiar story arc that lies at the center of our shared human experience: having our desires frustrated, then taking action to overcome those obstacles.
What about changing the world? Alas, that’s harder (and harder to measure). There’s some evidence I’ve “made a dent”: there are plenty of nice comments about The Art Of Troubleshooting scattered around the Internet, and the book’s reputation has opened up opportunities to reach even more people (e.g., speaking at OSCON). Most of all, I’m touched by the educators who have written to me, saying that my ideas made them see troubleshooting in a new light, finding them worthy of teaching future generations this critical problem-solving skill. Whether in the classroom, garage, office, or factory, understanding repair as a general set of concepts is exactly the intention I sent out into the Universe—and I’m grateful it’s been returned to me in such a positive way.
References:
- Header image: Herbert Ponting (1870–1935), photographer. Captain Robert Falcon Scott writing in his diary, Cape Evans hut. October 7, 1911. Retrieved from Wikimedia Commons, https://commons.wikimedia.org/wiki/File:Robert_Falcon_Scott_in_the_Cape_Evans_hut,_October_1911.jpg.
THE ART OF TROUBLESHOOTING 