What I Learned Writing My Book

Write Now!: The Guide to Making it in Freelance Writing is available on Amazon. (Photo: Matt Osgood)

Before I get started, I have to make two confessions.

First, I wrote my first book when I was 23. It was called Chasing Sunsets and I attempted to make sense of my year spent traveling around the country chasing love, adventure, and meaning. It was an audacious move, typical of a 23-year-old who believes that everything they’ve experienced meant something in the grander sense. I had life figured out. Why not share it with the world?

There are successes and failures in the book, which I recently picked up to look through as I was prepping the new book to launch on March 8th. It reads more like a diary than a story though there are scenes that work really well. Perhaps one day I’ll revisit and revise the book.

Still, I’m mostly referring to Write Now as my first book.

Secondly, Write Now was not the book I set out to write in the fall of 2018. In fact, I had another book outlined. I had done a fair amount of research and have a few files of sample chapters still in my computer. The book, which I will write some day, was at the starting line and its completion hinged upon a few contingencies coming together. They did not.

I began the fall relatively disappointed before I started putting together chapters for what began as maybe a PDF for followers of my blog or even just a series of articles for Medium. I didn’t really know. It wasn’t until I started piecing the book together and noticed that I had about 25,000+ words of writing that I considered to be a book.

Here is what I learned along the way:

(It’s in this space that I’m going to make a very emphatic note that these things were lessons I learned as I wrote, edited, revised, planned a launch, marketed, etc. for a non-fiction book. These worked for me. Maybe they’ll work for you.)

1. Organization is key: I started a completely new folder with the title of the book, which was originally “…Or Perhaps,” a title I still quite like. Each chapter (introduction, chapter one, and so forth) was clearly demarcated in the title of the file and what it was about. For example, “Chapter eight — Finding the correct publication.” The files were worded precisely and on purpose so that I knew what each contained. Additionally, I made a file called “Master,” which was — you guessed it — the master copy.
2. Open these files every day: I can’t be the only one who has their book tucked away in its own folder, but I found it helpful to open these files every day. Maybe not all of them, but a couple each day. It helped me build a relationship with these words. Often, as writers, and especially those of us trying to build up the nerve/have the audacity to write a book, just doing some of the work seems to be enough. There’s a file. It’s there. I don’t have the motivation — or inspiration or time — to get into that today. Don’t let this happen. Even if it means opening up one file and re-reading the first paragraph of the introduction chapter for the 34th time in a row. Open these files. Build those relationships.
3. “None of my friends or family will care about the content of this book:” That’s okay. People in my family will buy it. My friends will buy it. Do I care if they read it? No. Of course I want them to read it. I want them to read it and love it and recommend it to Peggy in accounting and all of Peggy’s friends, too. Our audience is our audience. Figure out who that is and write for them.
4. Write for that audience: Piggybacking off that last bit, I spent the first couple of chapters of Write Now really focusing on tone and language. I was concerned about prose and remaining detached from the story. I couldn’t help but include myself in some spots of the narrative, but I really tried to stay on the outside as the narrator of the story. But then that switched. When I realized the book was becoming both a practical “how-to” and a kick in the ass to writers, I thought about what it was that provided that kick in the pants for me: It was real, honest conversation. There were curse words and casual language. And so that’s why the tone of the book is so conversational. It’s exactly what I was say in the words I would use to say them if I were sitting down with these readers instead of writing a book for them.
5. Flexibility is the best ability: I remember passing along the full first draft to a friend of mine with an email that just said, “Now what?” It was nerve-wracking. Am I really taking this step? Then there was also this part of me who thought, “Alright, I’m going to get a response that tells me how great it is and how it should be published now.” That is, of course, not what happened. I got some praise, but also advice on cleaning language up, switching this or changing that, adding chapters here and there. This is missing. That is missing. And so I went back to editing, writing, and rearranging.
6. Find a team: You’re trying to publish a book here, not post a response to someone in your local newspaper’s comment section. Everything matters from content of the book to cover to marketing. Find advisors. Call in favors. Pay people if you have to: Editors/readers, graphic designers, marketing/PR friends who can offer advice. A ton goes into this endeavor. Surround yourself with people who know what the heck they’re talking about.
7. Plan a launch day: Don’t just publish willy-nilly. Have a day to send your book out into the world. This was you can plan everything around it: Facebook countdowns, emails, texts to friends, promotional material. Everything hinges upon this one day. Pick a date. Find it intentionally. Why did I choose March 8th? Quick story: I was on the phone with a PR friend of mine and I was doing this hypothetical scenario: “Blah blah blah book comes out March 8th blah blah.” She stopped me and asked why I chose the 8th of March. “No reason,” I assured her. “It was literally just saying a random day while I made my point.” She went on to tell me that she had just worked with a Vietnamese woman and they had discussed how in Vietnamese culture, the number 8 is seen as good luck because, on its side, it shows the infinity symbol. Thus, many Vietnamese weddings and business openings take place on the 8th. “You have to release it on March 8th,” she said, “I’m too superstitious for it not to be that way.” See? Good PR folks.
8. Email everyone you know: I went through address book in my email letter by letter (a, b, c …) and sent a BCC to everyone I actually knew. It didn’t matter. Old friend, best friend, cousin, cousin’s friend that was on that bachelor party email chain for 2007, and so on. Everyone got an email. “Book is coming out.” Give them the date. Give them a countdown. Email them every week and don’t feel badly about it. You know how you buy Girl Scout cookies from Kathy’s daughter every year? Remember the charity donation when Scott ran the Boston Marathon? Do you recall that the “about me” page you did for that friend, pro bono? This is your turn to ask for something.
9. Be a perfectionist: This is your book. Order proofs. How do the margins look? Does the design of the spine bleed over to the front or back? How do you feel about this? How’s the font? Too big? Too little? Should it be a different font altogether? These things are pains in the ass, but entirely necessary. You want to be happy with the whole product. If you’re looking at the spine of the book on the bookshelf and it bugs the heck out of you that the spacing is a little off but you can’t put your finger on it? Fix it. It was literally be the only thing you notice about your otherwise perfect book. And while literally zero other people will notice or even have an opinion, it’s worth doing.
10. Have extra eyes: On the back cover of my book, it read “indefinite” when it should have read “infinite.” These words, in a collection of literally tens of thousands, look very similar. However, they are different words with different meanings, conveying the opposite of what is intended. I don’t want “indefinite” opportunities (opportunities that don’t — but might some day — have a limit or conclusion); I want “infinite” opportunities. I had read the back of my book roughly 967 times and we were about four weeks from launch. The cover was finished and approved. I proudly showed off the final proof to a friend who’d never seen it before. Now, I love my friend Mark — named changed to protect the innocent — but I’d never ask him to be a proofreader. Maybe I should have. He read the back and asked, “Hey, did you mean ‘infinite’ here?” Face, meet palm.
11. Mention your book all the time: Be that annoying friend, but I also think there’s a psychological element to this. It is said that if you write a goal down, you’re more likely to achieve it. Similarly, if I’d told no one I was publishing a book, I wasn’t beholden to anyone. No one would know that I took the coward’s way out and just didn’t do it. But I told people and they were expecting a book, so a book I had to give them. When they asked, I had a date. And so on and so on. Make the title of your book appear in your social media profiles. Let people know it’s happening. Make yourself accountable.
12. Be humble, but persistent too: Look, it’s easy to finish it all and be humbled that a few people wanted to buy the book. Why bother more people? Don’t give into this temptation. Hit up your email list. Remind them the book is ready to be purchased. Remind them to head onto Amazon and write a review. Don’t be pushy. Thank them over and over. Use your manners. Even your good friends and family get caught up in other stuff. Life is demanding. You shouldn’t just expect everyone you know to have purchased your book right away. Maybe they need a little reminder. This is not being a pest. You should be proud of your work. Be persistent in getting people to buy it.
13. Find a way to get as many eyes on the book as possible: I want people reading my book on the train as they commute into the city or on airplanes. I want people to read my book in public places. I’ve put copies of my book on display at book stores and at Target. I’ve placed them in the library, all autographed. There’s no such thing as bad publicity when you’re selling a product. “Why does this book just keep popping up all over the area?” I don’t know. Maybe I’ll buy one. Might work. Might now. But find a way to get your book on the minds of as many people as you can.
14. Be positive & set realistic goals: We all have those days of self-doubt, but remember this: This book might sell 100 copies. Maybe 500. But you know what happens next? The next book sells 1,000. After that, your third book sells 10,000. The fourth makes you a $100,000. Let’s go!

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