12 Most Valuable Lessons Learned in the Long Write

12 Most Valuable Lessons Learned in the Long Write

I’ve always loved books. My idea of deviant adolescent behavior was to sneak a book under the covers with a flashlight. Much of the square footage of my home is still put to use keeping books warm and dry. Thus, when I was invited to write a book, a real book on paper between two covers, I was overjoyed. After all, it’s possible these things may go the way of vinyl LP’s, in which case I’ve had my opportunity to make an addition to the world of books.

Up to this point I’ve written numerous blog posts, a few articles, and like most people, thousands of emails — but never anything quite as extensive. Everything I’ve learned about writing hadn’t prepared me for the “long write.”

1. Outlines are your friends

Outlining is invaluable. Of course, the book started out with a top-level outline. Eventually, I outlined the contents of every chapter. Then, I looked at each and every paragraph, and wrote a sentence summing up the paragraph, and placed that in the outline. If it made sense there, I knew I was on the right track. The online tool WorkFlowy was a great help, as was the document map view in Word.

2. Interviews don’t give you word count

In a book project, you’re typically given a target word count. I confess I thought that by interviewing some of the smart people I’ve met, I’d get an instant bump in my word count for less effort than actually just writing. If anything though, it turned out to be more work, carefully reading and rereading the transcripts. On the plus side, though, I received the stimulation of hearing other’s ideas which turned out to be invaluable.

3. Transcribers are your friends

I didn’t start this immediately but after a few interviews, I found someone on Craigslist that would do transcriptions for a reasonable rate. Not only did it make my work so much easier, but now I’ve also got some nice material to edit into blog posts. I wish I had done it from the start.

4. Know your golden hours

I didn’t know it, but I discovered that I write best in the morning. I can sometimes get more done in the first two hours than I can in the rest of the day. I can still do great phone calls, brainstorming sessions and work with the team quite successfully in the rest of the day. What this tells me is that those early morning hours are precious and they shouldn’t be frittered away checking email.

5. Moving around helps

I like the stimulus of working in different places. For a while I went to NYC, planted myself in my apartment there, would spend part of the day at the library, and even went to the Metropolitan Museum of Art on one occasion. My most memorable moment was spent editing one chapter in the Temple of Dendur.

6. You’re going to use a lot of paper

Get over it. You need to constantly print out your pages on real paper so that you can mark them up. Looking at a computer screen just isn’t enough sometimes. I have a foot-high stack of paper to be recycled now.

7. Let’s get physical

I like getting physical. Scissors and tape became essential tools, as I would cut up the chapters, and rearrange, taping them together in new configurations. All of a sudden, the flat two-dimensional words became sculpture.

8. Embrace the Cloud

Dropbox is my friend. At first I worked in Google Docs as a means of having my manuscript available to me wherever I went. Ultimately, the non-Word formatting wasn’t helpful, as the ultimate manuscript had to be sent in as Word. I love Google Docs — but in this case I felt the added features of Word were what was needed — and being able to have those documents in Dropbox — and thus on my laptop or Desktop PC was perfect.

9. How many words?

The book project had a requirement of 60,000 words. Most book chapters come in at around 5,000 words (of course there are many, many exceptions). I took my book outline and placed it into a spreadsheet. At the end of each day’s work I would update the word count for each chapter. I worked on the book in a very non-linear way — more like a painting, in fact. Perhaps even more like a Jackson Pollock painting: all-over. I color-coded my spreadsheet so that different spreads of word count (i.e., 1,000 to 2,000 words, versus 2,000-3,000) would have different colors.

10. The writing of not writing

Not-Writing is as valuable as writing sometimes. When I got my original deadline, I was like “hey, this is easy — I just have to write 500 words a day, and I’ll be fine.” 500 words a day sounds easy — but at times squeezing out 500 words could feel like a home root canal kit, or an auto-trepanning session. I had some events that fell into place on my calendar, most notably Blog World, where I had a forced five days off. After that event the writing went so much smoother for a period of time. There really is such a thing as recharging your batteries.

11. Long is different

Writing a book and blogging aren’t the same. Some days, when I’d be pounding my head against the wall trying to eke out those 500 words, I’d take a break and write a blog post of 1000+ words. Effortlessly. Go figure.

12. Keep social but avoid avoidance

Staying somewhat active in social media was essential in the writing process. While sure, I’d lapse into obsessively checking my Twitter stream, sometimes, that Twitter stream, or Facebook, or Google Plus stream gave me new ideas that became part of the book. I know from my experience as an artist that many of us engage in avoidance tactics when it comes to the creative act. Sometimes, just as things are getting good in the studio is when the brain is screaming at you to go and sweep the front walkway. I’m not sure why this happens, just that it does — and that with experience, when we know these patterns are occurring, to acknowledge them, and move on. Sometimes, the avoidance activity actually helps — sometimes it’s just avoiding.

Every single one of these lessons came as a self-revelatory surprise. Reading, re-reading, and re-reading my own manuscript was often grueling, like a slog across an arid desert. But out of that difficulty emerged another surprise, and that was that the effort was incredibly gratifying. With the topic of social media it’s as though I’m writing about the advent of electricity during the age of Edison, or steam in the age of Stevenson — we’re living in a time of remarkable change. That, the thinking process, the interviews, and the research all came together to be one of the most stimulating learning experiences of my life.

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Featured image via Stock.Xchng.

Ric Dragon


Ric Dragon is the author of Social Marketology (McGraw Hill June 2012) and the DragonSearch Online Marketing Manual [http://www.dragonsearchmarketing.com/online-marketing-manual/]. He’s also a painter, drummer, and the eponymous leader of DragonSearch, a boutique online marketing agency in New York. He is a frequent speaker on the convergence of social media, information architecture, and business history, and has been a featured speaker at Blog World, SMX East, Conversion Conf, BrandsConf, CMS Expo, and other events.

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@RicDragon I can't tell you how many times I've started a book on a legal pad, or scribbles on bits of paper and then realizing the enormity of the task, shelved the idea. I love your ideas and the organization that you developed for yourself. One day, the day will come when I have no choice but to start and then complete a book; a short one, probably!


I liked #4 and #5 the best. You have to know your peak performance hours - and it is great to change the scenery once in awhile.

Nice suggestions, Ric.

PegFitzpatrick moderator


So thrilled for your 1st 12 Most post! I got little glimpses here and there as you worked on this project through social media. So much hard work!

Congrats on your achievement and much appreciation for sharing your journey here.

Kneale Mann
Kneale Mann

Ric, thank you for this wonderful post! It's so easy to say "I could write a book" or "Some day I wanna write a book". Well, like mountain climbing or alligator wrestling, saying it and actually doing it are two distant cousins of the same dream. So I will get back to you once I write my 90,000 words. Bravo!


I know many songwriters (myself included) that feel - for lyric writing especially - that the morning (after you first roll out of bed) is a very free association and productive period. I have a good friend who wrote many hit songs who made himself take one or two naps during the day so that he can have a few of these precious, inspired periods per day. Some songs can happen instantly - but some songwriters might spend the same amount of time on a great song as someone might spend writing a whole book. That all being said - for creative artist type writing - when you have to write something for a film or TV show ASAP, or have a deadline to get a song to an artist - you just have to do it and not make such a big deal out of it all. After you do it a number of times you gain confidence and no longer doubt the inevitable favorable outcome of your efforts - in fact you totally enjoy the intense focus and process. If you are getting freaky, overwhelmed, stressed or grumpy about any aspect - that is writer's stage fright - eventually you will find that to be unnecessary & counter productive. (...and it will make your friends & family wish you find a new profession!!)


My ultimate goal is to write a book. Your post is so informative and encouraging regarding the process, which scares the stuffing out of me. Thanks for sharing this, I will bookmark and keep as a reference!


@Kneale Mann oh, Kneale; not so bad, 60k will do :-) - or 30k for an eBook. But in the end, VERY gratifying experience.


@emaileboy That last sentence is priceless! "If you are getting freaky, overwhelmed, stressed or grumpy about any aspect - that is writer's stage fright - eventually you will find that to be unnecessary & counter productive. "


@sharongreenthal Thanks Sharon. Would love to see that happen! And it really is so gratifying. Tiring, yes, but oh so gratifying.