Friends often ask me how things are going with my book, Eating Glass: The Inner Journey Through Failure and Renewal, which I released in March 2021. For those unfamiliar, the book aims to help readers navigate the aftermath of a failure experience and find new life on the other side.
In this 5000+ word mega-post I’ll share some reflections, which might be relevant if you’re curious about my process as an author, curious about the book, or want to know what it’s like releasing a book of your own into the wild. There are no secrets here; I’ll share the good, the bad, and the ugly. I’m not claiming to be an expert; you should look elsewhere to learn about marketing. But based on data I’ve seen, my experience is pretty typical, especially for a newer self-published author.
Publishing this book was one of the most rewarding experiences of my life, but it’s extremely rare for a standalone book to gain financial success or a significant readership without being part of a much larger strategy. Eating Glass has consistently received glowing reviews from readers. Sales, however, have been lackluster; I’ve sold around 500 copies, mostly to people who know me. I knew this would be a difficult book to market but it hasn’t gained traction in any of the niches I expected it to. I will admit that I have not been nearly aggressive enough in marketing it, but it seems like every marketing attempt I’ve tried has failed to yield significant returns. I’m still trying to crack that code.
Fortunately I am being compensated in other ways—in deeply personal emails and phone calls from people who were moved by the book in the best possible way. The book had exactly the impact I hoped it would, on the people who needed it.
As I forge ahead, I’m doing three things: (1) Doing my best to not let the low sales get me down (2) Cherishing the positive feedback and (3) Putting on my entrepreneur game face, studying what’s working and what’s not, and taking pragmatic lessons on how I need to grow as an author-entrepreneur.
The Road to Publishing
I should back up and talk about my goals for the book. Eating Glass began as a series of cathartic reflections I wrote purely for myself, while navigating the aftermath of a startup failure. Over time, I saw the potential for turning them into a book that could help others. Even so, I agonized for months over whether or not I should publish such a vulnerable book. Maybe I was oversharing. Maybe I was in too raw of a place, and would look back on my experiences later with different eyes. Maybe I’d damage my reputation. Maybe the vulnerability on display would make others cringe.
In the end, I chose to publish two reasons: first, I was tired of being afraid, and needed to fully embrace my own journey. As I’ve written before, publishing the book was one of the most empowering experiences of my life.
Second, I wanted to help others. I wrote the book that I wish existed when I was struggling. Nobody, to my knowledge, had written anything quite like it. I also knew that I was hardly alone in my journey. I periodically read reflections from failed founders and other high achievers who suffered soul-shattering experiences. I knew the book would speak to them.
In the end, I wrote this book for people who needed it. Even if the world at large found the book mystifying, I would be satisfied if it spoke to the audience that needed it.
Positioning a Book About Failure
Once I made the decision to release the book, that still left numerous tactical decisions. How would I publish the book? How would I position and market it?
These were hard questions. I wanted to create an artistic masterpiece, but the tension between artistic quality and commercial felt real.
Too many artists blow off the business side of writing, and then pout when they don’t sell. I made this mistake with my self-published military SF novel The Lords of Harambee, which I’d spent a decade writing. I still think it’s a good book—certainly better than a lot of what gets published—but I only sold around 250 copies. I largely have myself to blame for that, because I designed my own cover (a huge no-no) and did almost no marketing.
This time, I wanted to set my book up for success. I researched extensively. I tried to get smart on balancing artistic integrity with commercial sales appeal. (For what it’s worth, Ryan Holiday’s Perennial Seller is the best I’ve found on this).
Still, this is a hard balance to strike. I repeatedly found myself facing decisions that would probably increase sales but undermine the book’s artistic integrity.
For example, the market is full of books with titles like “Fail Your Way to Success” or “Fail Big: Fail Your Way to Success and Break All the Rules to Get There.” If I ran market surveys or A/B testing to arrive at a title, the market would ask for more of the same. This is how you convince people to read a book about failure—by appealing to the deep, human thirst for guidance about how to succeed beyond your wildest dreams.
But this branding trivializes the painful reality of failure, which is the core of what I wanted to write about. Eating Glass was in many ways a reaction against this genre of pep talks. I designed every part of the book to convey to the reader that we would embark together on a serious, thoughtful journey through the underworld of a high-achieving life… from the title to the black matte cover with cool colors to the phrase “inner journey” in the subtitle. The word “renewal” promised an arrival and an inner transformation, but also suggested it would be subtle, perhaps wiser, and perhaps not quite like the “success” other titles promise.
If I was optimizing for commercial success, I also would have replaced Eating Glass with multiple smaller books targeted at different niche audiences. I would have written one short, practical book specifically for failed entrepreneurs and another for struggling graduate students. By focusing on niches, both would probably have outsold Eating Glass. But I was after something larger—a commentary on the universal human journey, with all its ups and downs, which spans an entire life through all its stages. The book’s most important but subtle themes, about growth from “first half of life” concerns into “second half of life” living, would have been lost.
In the end, Eating Glass is exactly the book I wanted it to be. I refused to compromise my vision for the book, but I was clear-eyed about the consequences of my choices. Eating Glass would probably not be a commercial success, but I hoped that it would be a hidden treasure for those who did read it. I hoped that struggling high achievers would pass old, dog-eared copies around when they met someone else walking a similar path. They would say, “Dude, you need to read this.”
Traditional vs. Self-Publishing
My next decision was about how to publish. I believed Eating Glass was high-enough quality to traditionally publish, so I put months of effort into writing a proposal, building a marketing plan, and sending query letters to literary agents. I built a platform—to include my website, blog, and mailing list—so I could show publishers that I was serious about helping Eating Glass reach readers.
I sent roughly a dozen query letters, in two batches separated by a couple months. A few wrote back form rejections, typically one or two months later. Many never wrote back at all.
This is pretty typical, and a dozen agents is not a large number. Authors routinely have to query far more than that, for far longer, before they get a lead. Becoming a writer takes a thick skin. With that said, I found this process infuriating, dehumanizing, and borderline abusive. There is no reason an agent or publishing house can’t take twenty seconds to send a form rejection letter, instead of leaving an author on the hook for months, until their hope slowly fades and then dies. The fact this is considered acceptable testifies to the power imbalance between writers and the publishing industry, and the desperation of most aspiring authors to be published.
I already have some deep life wounds related to rejection, so pitching a vulnerable book like Eating Glass wasn’t easy. The rejections (and silences) felt like a referendum on my life. I knew this dynamic would get even worse later, because even if an agent agreed to represent the book, I’d face another round as the agent pitched to publishers. The process would take years. And unlike most nonfiction books, which are sold based on a proposal and outline, Eating Glass was finished.
The more I researched and learned about the industry, the less sure I felt about the benefits of being traditionally published. Most of us view books through the lens of “survivorship bias.” We only know the books we see on the shelves at Barnes & Noble or on Amazon bestseller lists. The vast majority of traditionally published books never reach those shelves, or attain any level of fame at all. Furthermore, everything I’ve read says that in today’s world traditional publishers largely rely on authors to do their own marketing—and won’t even consider publishing your nonfiction book unless you already have a following of thousands.
After a few months of playing this game, I had to think carefully about my goals. I was frustrated and annoyed at the process. I had no desire to wait three years to hold a book that was ready for publication today. The agent dating game only fed my sense of rejection, when what I really needed to move forward was to embrace my story, get it out into the world, and move onto a new writing project. Furthermore, I was spending a huge amount of time building my own marketing plan. If a publisher wasn’t going to do much other than tell me to execute my own plan, why would I give them the lion’s share of my royalties?
What I really wanted was creative autonomy, agility, and the ability to tell my story the way I wanted. Self-publishing appeared increasingly attractive—not as a second-rate alternative to traditional publishing, but as a creative choice that gave me full control over my artistic vision and allowed me to work with agility and speed.
Self-publishing has become highly professionalized in the last few years if you do it right. James Altucher argues that the critical distinction today is no longer between traditional publishing and self-publishing, but between professional and unprofessional publishing. What he calls “Publishing 3.0” entails professional author-entrepreneurs leveraging freelance designers, editors, etc. to professionalize the self-publishing process.
I likely had enough access to my target markets—entrepreneurs, graduate students, creatives, and other high achievers—to reach them on my own. However, this would put a huge burden on me to market the book. Nobody would know it existed unless I told them.
Releasing the book
In keeping with Altucher’s philosophy, I tried to self-publish Eating Glass in the most professional way possible. I hired a professional cover designer through Reedsy. The result was amazing and exactly what I’d hoped for. I did deviate from best practices by doing my own editing and typesetting, but these are areas where I already felt strong, and I still relied on a team of early readers to provide feedback. I went through multiple rounds of paperback proofs from Amazon KDP. When everything was ready, I went through the Air Force’s media review process—then released the book in March 2021.
My initial advertising mostly consisted of social media posts on Facebook and LinkedIn and my small mailing list. I figured I would start with friends and family, then start a more intentional marketing campaign later. (In retrospect, I should have had a much more ambitious marketing plan at launch)
Friends and family embraced the book with great enthusiasm. I sold a couple hundred copies during launch week. I received many kind notes and affirmations from friends. After my months of fear leading up to the release, I found this hugely rewarding. Over the next couple weeks, friends texted photos holding their newly arrived copies. Those were priceless.
However, once I exhausted my own immediate network, sales practically stopped. That was hard emotionally but also exactly what I expected; nobody will know a book exists—especially a self-published one—without marketing.
The warm reception
The good news is that many people who read the book love it. Even as I struggle to sell books, I continue to receive kind, thoughtful notes from readers who feel deeply touched. They see their own experience reflected in its pages. “It’s like you’re reading my journals,” one reader wrote.
What I love is that each of these readers is on an entirely different journey. One recently left Los Angeles after a couple decades failing to build a successful career in the film industry. Another is an incredibly successful professional who struggles with hidden traumas that most people know nothing about. One is recovering from divorce, while another is a military NCO who has been on his own journey of healing from childhood trauma and combat PTSD. Eating Glass spoke to all of them, which is exactly what I hoped it would do. Something in the book speaks to a universal human experience.
For at least some readers, the book also has a timeless quality. One reader emphasized that he would return to the book again and again in his life, trusting he would continue to find new insights. Another reader told me the book now sits on a special bookshelf along with four or five other classics that he returns to continually throughout his life.
These personal notes mean the world to me. I have to think back to my original goal: Even if this book does not sell widely, I wrote it for those who need it. I love receiving individual notes affirming that the book has exactly the effect I hoped for. This is the success I want, although it is a very different metric than we usually think about. It is a metric about touching individual lives, not necessarily selling at scale.
The scaling challenge
With that said, I do want the book to sell widely. I have a message I want to share. I want to touch more lives. I have also invested thousands of hours in writing, with few readers and little financial return. This has entailed considerable opportunity cost, and it would really be nice to earn a return commensurate with my efforts.
However, scaling has proven to be an incredible challenge. I have tried a variety of methods to promote the book but none has made a significant impact. It is entirely possible that I just haven’t tried hard enough on any of these fronts; I will share more on that below. The book is also intrinsically difficult to market.
One of my first efforts was to use traditional advertising. I tried Amazon ads, which can be carefully targeted. I configured my ads to appear on the pages of books by authors who write on similar styles and themes—like Jerry Colonna, David Whyte, Parker Palmer, and Richard Rohr. I also configured ads to appear on the pages of other books about failure. The ads resulted in very few clicks and no sales. Because I only pay for clicks, and was receiving barely any, I stopped following the campaign. I just checked again, and apparently Amazon shoppers have seen my add 3500 times in the past year, clicked 11 times, and purchased 3 times. I suspect that because my click rate was so low, Amazon’s algorithm stopped showing my ads entirely.
Later, I tried using Google ads. I triggered these ads to appear for terms like “startup failure”, “founder depression”, and so forth, thinking these would lead to the exact niche I wanted to target. I was a little amused when, a few days in, Google’s dashboard informed me that most people were finding my ads by googling terms like “can you eat glass.” I did my best to exclude glass-eater terms but I’m not sure this ever fully worked; Google’s ad dashboard is highly opaque. By the time I was done experimenting, 158,000 people had seen my ads and 192 had clicked the link, which took them to my book’s Amazon page. However, zero of those 192 purchased the book.
A 1 in 1000 click rate didn’t sound unreasonable to me, but the zero sales were concerning. That could indicate two things: (1) something about the product page was turning people off or (2) the people seeing and clicking on my ads were not the people I was trying to target.
Option 1 was a possibility. The cover was (I thought) beautiful and the book had 4.9 stars with dozens of thoughtful reviews. However, the product description was focused on my personal journey. Perhaps that didn’t catch people’s interest? I rewrote the product description to emphasize the universal journey through hardship towards richer, wiser living. The new blurb focused on what the book could do for readers. I continued the ad campaign for another week but still sold no books.
Option 2 looked increasing likely. Maybe the glass-eaters were seeing my ads, not startup founders; when they realized that my book was not, in fact, a manual for how to eat glass, they bounced. Given that I was losing money on each click, I shut down the campaign.
I initially hoped my blog would gain readership if I shared blog posts on Facebook or LinkedIn, but almost every post only receives 1-2 likes. My suspicion is that the algorithms on these platforms significantly downweight posts that link to articles on external sites.
Blogging is hard work and it can take years to build a following. I have no doubt that if I blogged three times a week for years, I could build a following of thousands. The problem is that this becomes almost a full-time writing commitment, and what I really want to do is write books, not blog posts. The most successful blogs also have a tight focus on a specific theme, but I like to write across a range of interests—a common situation that prevents many aspiring writers from finding commercial success. My difficulties resolving these tensions have been the hardest aspect of trying to launch a writing career, and explain my erratic presence on the blog and social media.
Given the small size of my own readership, I experimented with writing guest posts for other blogs with large readerships. For example, I am friends with the editor of From the Green Notebook, a wonderful blog about leadership and personal growth, which has over 17,000 email subscribers and a large social media footprint. I sent him a free copy of Eating Glass, which he read, loved, and reviewed on his mailing list. He also gave me the opportunity to write two different posts for his blog and mailing list. The net result of all this activity was around 10 book sales.
I also wrote a lengthy article for Failory, a site that specifically shares resources about startup failure. This is as close to my target niche as you can get, but I sold zero books after the article went live.
I’m pretty good at connecting with live audiences, so webinars and podcasting seemed like a great way to draw people into my story. I did a book launch webinar with the Defense Entrepreneurs Forum and have done ten or so podcasts so far. The webinar drew perhaps 10 people, about half of whom were family.
Some of the podcasts presumably reached hundreds or thousands of people. Each of these engagements was a positive, intimate, and heartwarming experience. My podcast hosts loved my books, and we had sincere, authentic conversations. However, after the release of each podcast episode, I typically only sold a few books.
I have also actively engaged in relevant startup-centric forums for discussions about startup failure, impostor syndrome, burnout, and other themes my book addresses. The primary site I monitor each day is Hacker News (incidentally, my favorite place on the Internet), where a lot of entrepreneurs hang out. In addition to talking about coding, the site features surprisingly frequent and rich conversations about how to construct a well-lived life.
There is a danger of coming across as sleazy and self-interested in forums (repeated posts that say only “buy my book!”) so I have tried hard to make each post value-adding. I personally address the original poster’s issue, share a link to a free chapter, or even offer to send a free copy of the book to the original poster. When a conversation about loneliness appeared on Christmas, I wrote a post making the e-book free to anyone who wanted it for 48 hours.
I have similarly reached out to strangers on Facebook in groups focused on graduate student mental health.
Each of these engagements typically yields between 0 and 2 sales.
HackerNews also has a feature called “Show HN”, which allows users to showcase new creations that might be of interest to other HN members. These posts can go viral, generating a windfall of interest and support for compelling projects. I thought “Eating Glass” could do quite well, given the composition and interests of the readership. I spent weeks preparing my website with abundant free content. Unfortunately, my “Show HN” post failed to gain any traction and was swept downstream immediately. I sold no books.
Releasing an audiobook
The best thing I did for Eating Glass after its original publication was record an audiobook version and release it on Audible. Although not really a form of marketing, it created a second product that made the book accessible to those who might not have time to read. In a few months I have sold more than 100 copies of the audiobook.
I recorded the audio myself. In keeping with Altucher’s philosophy of professional self-publishing, I spent considerable time researching quality microphones, tweaking settings, and setting up a recording space with good acoustics. By the time I had finished, I’d recorded every chapter two or three times to get the level of quality I wanted. I also did extensive post-processing, using automated filters and then doing the manual, painstaking work of removing breath noises and lip smacking.
The learning curve was steep, but in the end, I think the book sounds terrific. Listeners have commented on its professional quality. Now that I’ve done it once and developed a workflow, it will be much easier to do again for future projects.
Hitting my networks
Part of my marketing plan was to reach out to networks I’m a part of, such as my high school alumni network, the USAFA alumni network, and a large national security listserv that I’m a part of.
My messages to the alumni networks led to a decent number of sales in the first weeks, probably all from people who personally knew me.
As for the national security listserv, the moderator loved the book and enthusiastically recommended it to the entire list. Net result? Possibly 1-2 sales, along with a personal email from one member about why most members of a national security-focused group would never read a book about personal reflection.
My biggest line of effort has been reaching out personally to individuals who I think might like the book and sending them a free digital copy. When that didn’t yield the results I’d hoped, I switched to mailing physical copies along with handwritten notes on elegant, personalized stationary.
I have written to numerous failed founders who have taken the brave step of writing publicly about their experiences. I have written to venture capitalists who run mental health programs for their founders. I have written to psychologists who specialize in entrepreneur mental health, and CEO coaches who specialize in vulnerability. I have written to authors I cite and podcasters I listen to.
I like doing this kind of advertising more than anything else, because it is far more personal and feels more like a mutual exchange. I am writing people I respect, whose work I have read and loved. However, it can also be the most demoralizing form of advertising, because the rate of engagement still remains low, even among people I thought would absolutely love the book. I suspect the vast majority of these people are simply busy and overwhelmed. For every 20 notes I send, I might get two or three polite dismissals and one lead.
The rare wins
The key words here are “one lead.” That seems to be where the magic is found. I mentioned earlier that I put a great deal of work into reaching a friend’s mailing list of 17,000 but only sold 5-10 books. One of those 5-10 people was an Army NCO named Mike Burke who runs a podcast called Always in Pursuit, about leadership and vulnerability. He is the guy who now keeps Eating Glass on a special shelf with his other classics, and he quickly reached out to arrange a podcast interview. He now shouts about Eating Glass from the rooftops, so I sent him a box of free books to give away. I, in turn, get to tell you about how much I love his podcast and the way he is inspiring more authentic, introspective leadership in his listeners.
His enthusiastic support for my book led me to a few other supporters, each of whom led me to more. Compounding interest is at work here, but I have to fight for it aggressively.
Some of these leads have also led to enjoyable moments of connection. Dr. Michael Freeman, a psychologist and psychiatrist who focuses on startup founder mental health, read the copy I sent and sent a nice note. So did Dierdre Wolownick Honnold, a rock climbing hero I discuss in the book (although, embarrassingly, she informed me I’d made a couple factual mistakes when I told her story… another lesson learned, about fact-checking during editing).
Even as I consider how to generate more sales, I try to stay focused on these interpersonal relationships. I have to remind myself that Eating Glass achieved my original goals, and that each of these one-on-one moments of connection is its own reward.
Where do I stand today? A year after publishing Eating Glass, I have sold around 400 books and just over 100 audiobooks. I continue to sell 5-10 copies a month. People who read the book seem to love it; it has 4.9 stars on Amazon and receives heartfelt praise, but getting people to read it often feels impossible.
It is easy to get discouraged. This is the point where many writers quit, but the writers who succeed mine their experiences for lessons, learn, and get back to work. So what can I learn from all this?
- As a writer, I have the privilege of making my own choices… but I also live with them. Eating Glass is exactly what I wanted it to be. I did not compromise my artistic integrity in creating the book I wanted. I knew from the start that I was making choices that would hurt its commercial viability, but I also knew it would speak deeply to the audience that needed it. Both predictions proved to be true.
- I think ‘failure’ is a negative emotional trigger. The science around advertising is fascinating. A single word can activate powerful subconscious forces that lead a consumer to buy or avoid a product. I can’t prove it, but I now strongly suspect that the word ‘failure’ is a negative emotional trigger that most consumers recoil from.
- Marketing experts are right: work that doesn’t fit neatly in a genre is a hard sell, and memoir is among the hardest genres to sell. Eating Glass sits between a personal growth book and memoir. That ambiguity enriches it but also makes it hard to position. Also, I may have branded it too much as a memoir. What’s become clear is that selling memoirs is hard, because people are most inclined to read memoirs of celebrities or people they know personally.
- Writers must fight for every reader. When I was running my nonprofit, an advisor who had expertise in fundraising told me that he had to court each individual donor personally, no matter how big or small their donation. That advice stuck with me. It’s tempting to wait for a magic bullet that will generate waves (Brené Brown, if you’re reading, you’re welcome to endorse my book!) , but most writers need to fight for the heart of every reader. Even if I’m only selling 1 or 2 books each time I engage with an audience, I should embrace that audience.
- Exponential growth is slow in the beginning. Almost every writer has to slog their way through years of slow growth before they reach a bend in the curve. This is normal. Breakout writers keep putting in the work.
- Writers need to be persistent and aggressive in marketing. I have admittedly fallen short here. I tend to market in intermittent waves, rather than maintaining a consistent pace. Successful writers spend as much time managing their business as they spend actually writing. This is my biggest growth area as a writer. It’s not too late for Eating Glass; there is a lot I still need to do.
- Building a writing career is a strategic enterprise that plays out over years. Writers often say that your next book is the best marketing for your current one. If you build a readership over years, hungry readers will look to your backlist. Professional writers to continually produce new work in order to grow a career. I won’t be able to assess the performance of Eating Glass for years or decades.
Lessons for Others
Readers who have made it this far, and are considering publishing their own book, should know that my experience is pretty typical. According to Scribe Media, the average self-published digital only book sells roughly 250 copies in its lifetime. The average traditionally published book sells 3000 copies. These are not large numbers.
This doesn’t mean you shouldn’t publish a book; you should!
It just means that you should have realistic expectations about what publishing a book will or won’t do for you. A standalone book probably won’t make you a fortune or catapult you to fame, but it can serve many ancillary purposes: satisfy your thirst to create, give you pride in a difficult achievement, grow your skills and confidence, help you build relationships with readers, demonstrate your expertise, attract clients or customers to your other business services, or usher you into new relationships and communities.
Anyone considering self-publishing a book should also get smart both about the self-publishing process and the business of writing. One of the best places to start is with Joanna Penn’s website, The Creative Penn.
Once you publish one book, it becomes much easier to write a second. I learned a ton with Eating Glass. I know how to publish an e-book in minutes. I know how to hire freelance cover designers, typesetters, and editors. I know how to obtain ISBNs and make my books available for distributors to major bookstores through IngramSpark. Although I haven’t quite cracked the code on gaining value from paid ads, I know the basics of how to use them. With these skills in hand, publishing a second book will be much easier. I can see how highly productive author-entrepreneurs become engines for continually delivering new books and services.
In summary, releasing Eating Glass was a milestone for me. It was one of the most empowering experiences of my life, and I love knowing that I have touched at least a few lives through the magic of writing. However, publishing a book is only one milestone in its journey, and it’s an even smaller milestone in an author’s career. I have to continually navigate feelings of hope, disappointment, and exhilaration, even as I have to keep doing the hard work of connecting the book with the world.
As I consider my lessons learned about publishing and marketing, two stand out. First, creators operate in a realm of exponential math and compounding returns, which is not necessarily intuitive. It is easy to get demoralized when our mailing list grows by 1 person a month, our posts only get one or two likes, or our sales numbers hover near zero. But each additional connection we make links us into an ever-deepening web of relationships and opportunities. As exponential magic goes to work, a rise might come any time. I’m learning that the hard part is staying committed to the work—to producing—regardless of what the numbers seem to indicate.
The second thing I’ve learned is the primacy of individual, personal relationships. That is where I’ve found my value as a writer lately, as I shared in my post about Messages in Bottles. That is what keeps me going. All of us want to make a difference with our lives, so there is no higher pleasure than receiving a note about how my words have positively influenced somebody. As long as I continue to receive occasional notes like this, I know I am succeeding.
The real magic is that these two lessons fit so well together. In a world of compounding returns, it is individuals who matter. A new relationship with a single reader is not merely an additive increment to a sales chart. A new reader is a unique individual with his or her own passions, perspectives, and community of relationships. Each new reader connects a writer to a much broader community and an entirely new web of relationships. That is exhilarating and scary, but it’s also… well, magical.