8 Lessons I've Learned By Self-Publishing 3 Kindle E-books

Book publishing back in the day

When I was in my 20s and 30s, my dream was to publish the Great American Junk Novel. I had no illusions about my ability (or, rather, inability) to write something profound, but I truly believed I could write a Bridges of Madison County or Da Vinci Code. I was wrong. After innumerable efforts, I gave up. I have no imagination, no sense of character, and I’m incapable of writing dialog.


Thanks to the blogosphere, however, I discovered in my 40s that, while I’m not and never will be a novelist, I am an essayist. Over the past decade, I’ve written over 11,000 essays, which easily qualifies me for “expert” status. My blog has become a vast repository of my thoughts on just about everything: politics (mostly politics), parenting, education, Hollywood, social issues, national security, travel — you name it, and I’ve probably written about it.

Considering how many hours I’ve spent at the keyboard, I’ve always hoped that I could monetize my blog. Unfortunately, while I’ve got a solid, and very dear to me, following of readers who genuinely like the way I think and write, I’ve never leveraged my way into the Big Time amongst conservative bloggers. Not being in the Big Time means that any monetization I’ve done has earned me just enough money to buy a few books, not to make a mortgage payment or two.

A few years ago, it occurred to me that I might be able to make some money if I took my writings to a new readership. That’s how I decided to try my hand at self-publishing. I saw it all clearly:  I would assemble my essays, package them attractively, upload them at Kindle Direct Publishing, and sell them for a profit on Amazon. It seemed so easy….

Sadly, it wasn’t easy, at least not the first time around. That didn’t deter me from publishing a second e-book and, just recently, a third. Each book has been easier than the one before, so I’d like to share with you some lessons I’ve learned, many of which I learned the hard way.

Self-publishing Lesson 1:

Don’t fall in love with yourself.
Every word you write needs to earn a place in your book before you foist it the public.

To assemble my first e-book, I read over 7,000 of my old posts. Although it got somewhat tedious, I’m narcissistic enough to have found the experience rather enjoyable. One of the things I noticed immediately is that my writing has improved tremendously over the years. In my case, practice hasn’t made perfect, but it’s certainly made better. Learning that I’ve grown as a writer was a rewarding experience in itself.


I also learned that I’ve often been prescient how American and world events, although that’s not saying a lot, considering that both politics and politicians tend to be predictable. Lastly, I learned that I’m a really lousy proofreader. I often slam out posts during the interstices in my day. That’s meant snatching reading and writing time in the minutes between legal work, child care, household maintenance, family vacations, elder care, exercise, surgeries, and whatever else my days have thrown at me.  The results weren’t always pretty.

As I read through those 7,000+ posts, every time I found one that I thought would work in an e-book, I copied it and pasted it into a Word document. Eventually, I had a 564-page Word document. Hmmm. Some trimming seemed in order. It took me months to do the trimming, and I still ended up with a 155,000 word file. Even I, in love with the sound of my own authorial voice, knew that this was too long. I went through all the material again, and finally brought it down to under 100,000 words. I would have done better at that point to remember that brevity is the soul of wit — or at least the essence of readability — and to have made another cut.

One-hundred thousand words is way too many for several reasons: (1) It’s difficult to impose an organizing principle (i.e., chapters and sub-chapters) on that much material; (2) It’s difficult to proofread that much material; and (3) Even the most well-intentioned people get bored when faced with that many words in a huge batch. People who will read the same essays with pleasure when spread out over a period of years get tired of them when they’re clumped together in a single book.

Self-publishing Lesson 2:

Before you start formatting your book, brush up on the ins and outs of Kindle formatting.
It will save you a lot of time, effort, and frustration.

After I’d finally figured out what essays I would keep, I carefully formatted the whole collection, so that the final product would look as I like a book to look. That was really dumb. The first thing I should have done was to read up on Kindle formatting advice. Had I read this information first, I would have known that, while it’s a fine idea to write your e-book in Word, that doesn’t mean that you can format your work as you usually do. In order for books to appear properly on a Kindle (or Kindle app), you need to follow very careful formatting requirements. Otherwise, you end up with a mess.  I ended up having to reformat all 100,000 words, which was a tedious process made all the more frustrating by the fact that I could have done it right the first time.


I highly recommend Amazon’s own publication, Building Your Book for Kindle for all of the basic formatting information you’ll need. Additionally, for a simple approach to stylish formatting, you may want to get Aaron Shepard’s From Word to Kindle: Self Publishing Your Kindle Book with Microsoft Word, or Tips on Designing and Formatting Your Text So Your Ebook Doesn’t Look Horrible (Like Everyone Else’s).

Self-Publishing Lesson 3:

If you’re not artistic or, worse, have no visual sense at all, do not design your own cover.
You will just make a fool of yourself.

The next big mistake I made with my first book was to design the cover myself, starting from scratch. I am a person who lacks any artistic aptitude whatsoever. Undeterred by that handicap, I went ahead and came up with the ugliest cover you’ve ever seen:

Bookworm Turns cover

For those potential purchasers who judge a book by its cover, it was instantly clear that they were looking at the worst book ever. Not only was it ugly, the cover was also incoherent. The landscape photo I used had been, for many years, the image at the top of my blog, but only my loyal readers would know that. For anyone else looking at the cover, it gave no hint as to the book’s contents.

I finally figured out that an ugly, meaningless cover is not a selling point. Since I was still too cheap to spend money on a cover, I came back with a different homemade design. It was cleaner and, I thought, made more of a statement because it had an angry “[book]worm” looking backwards (a bookworm turning, right?):

Book cover2

I was delusional, of course. That is still one ugly and meaningless cover.

Self-Publishing Lesson 4:

There’s a magic price point out there, the one at which the book sells and the author still makes a profit.
Unfortunately, I have no idea what that price is.

Eventually, I did get my book published and, thanks to the good offices of friends in the blogosphere, it gained a little bit of traction. After several months, it had brought in enough money that I could sit back and say “Yup, I earned a good 75 cents per hour spent on that book.”

And speaking of money . . . pricing the book was a challenge. That was mostly because of my ego. I’d poured so much of myself and my time in the book, I couldn’t bear to price it at 99 cents or $1.99. After all, it was almost 100,000 words long! Surely that was worth something. I therefore priced it at $4.99, blind to the fact that no one is going to buy an overlong book of essays with an ugly cover by an unknown author. When I figured this out, I dropped the price and did get more readers.


My largest batch of sales occurred when two things happened simultaneously: (1) I marked the price down to zero (which Kindle Direct Publishing lets one do for short periods of time for marketing purposes) and (2) Instapundit gave the book an “in the mail” nod. Electronic copies flew off the cybershelf. It was all very exciting, but when the price popped back up to real money, people instantly stopped buying again. My book simply didn’t have what it took to gain traction.

After reading everything I’ve confessed here, if you are the kind of hearty soul who would still like to read this huge collection of my past essays, all hiding behind an ugly cover, the book is The Bookworm Turns: A Secret Conservative in Liberal Land. I can honestly say that it won’t just give you hours of enjoyable reading but will, instead, give you days, weeks, and possibly years of reading pleasure.

Self-Publishing Lesson 5:

Unless you just like writing and formatting books,
don’t bother self-publishing if you don’t have a marketing plan.
Even a small-scale marketing plan is better than none at all.

My second book went somewhat better. This time, I decided to write a short book that built upon my posts about parenting, a subject near and dear to my heart. Riffing off the lessons I’d learned the hard way with my first book, I kept the second book short, reviewed Kindle’s formatting requirements before I began to do the formatting, and didn’t design the cover from scratch. That didn’t mean, though, I was going to stop looking for a cheap way to create a cover.  After all, I’m as cheap as they come and I didn’t expect to make real money from this effort.  I therefore went to Shutterstock, purchased an image (it cost $8 or $9), and then personalized it. The resulting cover wasn’t great, but it was better than my first two efforts:


The image still has nothing to do with the book’s content, but it’s bright, eye-catching, and it admirably shows off the title — a title long enough to give the casual Amazon browser a good idea about what’s inside.

In terms of formatting, I didn’t learn anything with book no. 2 that I hadn’t already learned with book no. 1. In terms of marketing, I learned a lot, all negative. I had no idea how to market this book, since all my blog friends write about politics, not parenting. Because the topic didn’t mesh with any I know and because I was too diffident (and my life too busy) to try to promote it outside my circle of blog friends and readers, the book just sat there, going nowhere.


I’m actually rather fond of my own parenting advice (there’s that narcissistic ego again), so I’m happy to do a little marketing here and recommend to you my second book, Easy Ways To Teach Kids Hard Things : The fun way to teach your children important life principles. At the very least, it has a cheerful cover.

Self-Publishing Lesson 6:

Images brighten up a book, but be sure to research carefully how the image size
and number of pixels, as well as the way to insert images into the file, to save them with the file,
and to upload them onto Kindle Direct Publishing.

Undeterred by my two previous forays into self-publishing, I decided this year to try yet again. I’ve mentioned before that I’m cheap, and part of being cheap is having a “waste not, want not” mentality. Using perfectly good essays only once just seems like a waste. The logical thing to do is to recycle them into yet a third Kindle book. The experience this time was so effortless (almost), that I can envision a fourth self-publishing effort.

By this third outing, I knew to (1) keep it short and (2) get the formatting correct out of the gate. With those hurdles cleared, I decided to add two different elements to increase saleability. The first new thing I did was to include images. (Because I’m very paranoid about copyright issues, all of the images are public domain images.)

When I first decided to use pictures, I assumed that I would just insert the images into the Word text, format the book as usual for Kindle publishing, and that would be that. That was not that. I learned that Kindle doesn’t handle images well, and that there are very specific ways to format the image files, to insert images, to save book’s file for publishing, and to upload both text and pictures. After a lot of head-scratching, I had the wit to search up the images chapter in Building Your Book for Kindle. If I were to do it again, I would also buy Aaron Shepard’s Pictures on Kindle: Self Publishing Your Kindle Book with Photos, Paintings, Drawings, and Other Graphics, or Tips on Formatting Your Images So Your Ebook Doesn’t Look Horrible (Like Everyone Else’s).

Self-Publishing Lesson 7:


If you can, have a professional design your cover.
It will catch potential readers’ eyes, telegraph information about the book to them,
and make you feel better about your product.

The second new thing I did was to hire a professional graphic artist to design the cover. It was a hard step for a cheapskate like me, but I feel it was worth it. So far, I’ve sold enough books to cover half of the cover’s cost. A few more books sold, and everything else will be gravy. As you can see, the cover isn’t just visually appealing. My clever designer also signaled that the book is patriotic (the nicely balanced red, white, and blue theme), scholarly in a lighthearted way (the pince nez), and whimsical (the little worm):

Bookworm Returns

(If you would like to touch bases with the designer, who is a friend of mine and a lovely person, please email me at bookwormroom *at* gmail.com.)

Self-Publishing Lesson 8:

Self-publishing means self-promoting.
You’re going to have to reach out to your friends to help you market your book.
Let them know that you will, of course, be delighted to do the same for them one day.

I’m now in the final phase of my latest e-book, which is the marketing phase. Before I even uploaded the book to Kindle Direct Publishing, I sent PDF versions to friends who agreed to write reviews (like this or this). That way, as soon as I uploaded the book, I was able to include their reviews in the product description. I also included in the product description good reviews for my previous two books. When curious readers check out the Amazon page, they’ll see that I have a track record. I also updated my author page to ensure that all three books appear there.

My next step was to send out an announcement (I like MailChimp for mass emails) telling all of my blogosphere friends, both near and distant, that I’ve published a new book. Many of them have been kind enough to link to my book at their sites. PJ Media also extended an invitation to me to write about my adventures in self-publishing. In a few weeks, I’ll irritate all these friends and acquaintances by sending out another email asking them, if they read and liked the book, to write a review at Amazon and give it some stars. Those reviews and those stars make a big difference in sales. I’ve also put out regular announcements on Facebook, Google+, and Twitter informing friends and followers that my book is out there.


And now comes my last act of self-promotion here at PJ Media: If you’d like to show me that this effort in marketing outreach has worked, I invite you to buy a copy of The Bookworm Returns: Life in Obama’s America for only $2.99. Then, settle back, read, and enjoy.


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