19 Lessons I Am Learning From Writing My Book (Plus a Note on Honesty and Failing Expectation)

EDIT 08/05/2018: And now for the long-awaited Lesson #20: publishing a book is JUST AS HARD as writing one. But I did it. My debut novel, The Heretic’s Guide to Homecoming, is now out in the world, waiting for you all to jump in and pick it apart for things I say on a daily basis so you can confirm I wasn’t kidding about Lesson #16.

What do students use Reading Week for? Sometimes, as one of my profs said, “Reading Week” is code for “skiing week”; sometimes it’s time to book that trip to Mexico or Cuba to get some much-needed sun after the long dark of Canadian winter. Sometimes it actually is what it says it is–a week of holing up and studying for the assignments that are due once school kicks back in.

But for me, it was less a Reading Week and more a Writing Week.

IMPORTANT: Okay pals, now’s your time to shine. I need you.

Reading Week is this week, and I want to use it wisely. I want to use it as a retreat from my regular unreasonably-packed school/work schedule. I want to use it to read and reflect and do lots of yoga but MORE THAN ANYTHING ELSE IN THE WORLD, I want to use it to WRITE MY BOOK.

The book is pretty much book-sized by now. (It’s at 150k, give or take a few thousand words.) What I need to do–what I’ve needed to do since October–is to go through and edit the draft into a semi-final manuscript. I go back to classes Feb 22, and I’m going to need the weekend immediately preceding that to prepare for exams/assignments, so my deadline is FEBRUARY 19.


I have faith in my own ability to edit that much content in five days. But I’m gonna need some help.

This is a quote from a long post I published on Facebook asking for support–in the whirlwind workweek that followed, I got exactly what I asked for. I had a dozen separate people send me messages asking ARE YOU WORKING ON YOUR BOOK BECAUSE YOU SHOULD BE; I had people keeping me focused and on-track and, importantly, away from distractions. My partner found and posted this comic-guide about “The Care and Feeding of Writers” on my Wall. An amazingly talented musician friend improv’d a song about me and my writing to motivate me.

I had the full and enthusiastic support of probably just under a hundred different humans while I chased the lofty goal of finishing the editing of 150k words of book in five days.

And in the end, it didn’t happen.


1. You cannot edit 150k words of a book (if you want to do it well and proper)
2. You CAN edit 80k words of a book, or just over half the manuscript
3. ‘Editing’ becomes ‘rewriting’ pretty fast when you’re working on 2-year-old material
4. If you can just cut/paste and rearrange the scenes with minimal damage to the plot, the scenes need to be written better
5. Green tea and dark chocolate are as much writing essentials as paper or laptop
6. The middle bit is always, always more difficult than beginning or end
7. Lofty goals are important–and so is failing at them (there’s a bit in the book about that. and by a bit I mean about 76k words.)
8. No matter what, the support of other humans is vital

This is part of the follow-up post I published updating everyone on the status of the editing on Saturday February 20 (AKA one day after I was ‘meant to’ be finished with it.) It sounds the same as I always sound, vaguely educational and vaguely witty and vaguely all-caps-y and pretty definitively self-confident.

But to be really truly honest, I was nervous about posting it. Because it meant that I wasn’t finished. Because it meant that I hadn’t done what I said I would do, that I had propped up this big sparkly goal and then failed to achieve it. Because it meant that I might disappoint everyone who was supporting me to do it. There was actually a moment where I considered flat-out lying and saying I’d finished the editing when I was, in fact, nowhere near completion; it seemed less painful than telling the aforementioned almost-hundred humans hey, that thing I pumped you all up for, it’s not happening the way I said it would.

I worry about disappointing people a lot. And about whether they’ll still like/trust me or find me reliable if I make big, slightly-improbable goals and then fail to achieve them how it was ‘planned’ for me to. And about whether the work I’m doing even matters to anyone other than myself.

So what gave me the courage to be honest about coming up short?

Refer to #7 on the list. Ironically–and very usefully–these issues are extensively covered within the book I’m writing. All it took was a look at my own story to remember the reasons why it was important to be honest about my progress: because it was still progress, still important, still way WAY further down the road than I’d been five days before. All it took was a quick consultation of my characters for them to remind me of the lessons I created them to teach.

Which, I suppose, is why I’m writing it in the end. It’s a good story–but it’s also a compendium of all the lessons I have the most trouble retaining about life and success and society and finding purpose in what you do. So I can have a few friendly faces to nudge me back into the right mindset when I need it. I’m sure most other writers can understand.

So in honour of that, I have for you an extension of the little listpost above.

19 Lessons I Am Learning From Writing My Book:

  1. The more important something is to you, the scarier it is to do it. The closer your art/creation/whatever is to your heart, the more you will fear its rejection or its imperfection or even its completion. So it follows that the art you are most afraid of getting started on/finishing/mucking up is the art you need to work on the most.
  2. You don’t need to take every good idea someone suggests to you. Even if it’s a really, REALLY good one. If it doesn’t fit, it doesn’t fit, and you are under no obligation to try and make it fit. It’s your art; your intuition rules above all. Take what works, leave the rest.
  3. The tools of the trade extend beyond paper/pen or laptop and word processor. They also include sunlight, fresh air, good food, inspiring music, long thoughtful showers, equally long thoughtful yoga sessions, and clean, visually-appealing spaces. These things are not add-ons or accoutrements; they are as necessary to the writing as anything else.
  4. Your writing will change. It will improve as the weeks and months and years go by. And sometimes you’ll look back on something you wrote and think “it doesn’t fit”. And sometimes you’ll look back on something you wrote and think “I could do better than that now”. And you’ll be right.
  5. That is to say: be ruthless with your editing. If you want to scrap 16,000 words and rewrite 35,000 in their place, go for it. If you want to edit out entire plot points, entire places, entire people because they no longer serve the Greater Narrative, do it. Every new version of the story brings it closer to home. Closer to you. Closer to The Point.
  6. Having said that, remember to keep all the old versions. Don’t just delete them altogether. There might be something in there you can use later down the line. You’d be surprised what fights for life and breath, what demands a second chance.
  7. Sometimes, destiny looks like a big shining neon sign above something or somebody and it’s impossible not to notice it. Sometimes, destiny is quiet, unobtrusive, mundane-looking, easy to miss when you’re not primed for it. Both are equally good, but one is easier to chase than the other, and it might not be the one you’re thinking it is.
  8. Trying things that you are uncomfortable with is the only–the only–way to grow comfortable with them. It is the only way to grow, period. And if you can stop taking yourself quite so seriously, you might even have fun doing it.
  9. I’ve already said it, but it’s worth saying again: lofty goals are important. So is failing at them. As I read recently, failure is a feedback mechanism. Better to dream up something totally amazing and impossible and throw everything you’ve got at it regardless of whether you achieve it exactly how and when you anticipated, than to stick to small, ‘reasonable’ goals.
  10. You are dying. Right now, as you’re reading this. Time is slipping by second by second by second by second. And you aren’t getting any of them back. As a friend of my father once said, “life is biterminal–having begun, it ends”. The faster you appreciate the magnitude of this inescapable fact, the faster you can start doing the things that matter to you now.
  11. What you are trying to say is more important than the artform you choose with which to say it. The message is more important than the medium. “The what, they said, it shows up on you easy, shows up bold as sunrise—it is the why that is so well-hidden.” Figure out the why. If you have a good why, the what will invent itself.
  12. The writer’s cycle goes like this: you start, you love it, you’re passionate, you work, you work, you work, you work, you hate it. You think it’s the suckiest thing in the world and that nobody will care because even you don’t care. And then. And then you take  a break, go for a walk, watch a movie, come back to it the next day, and it’s beautiful again. Here’s a tip that took me years and years to learn: when you hate part of your writing, you should probably change it. When you hate all of your writing, you probably just need a snack.
  13. Success is measured in satisfaction, not completion. Did you get what you wanted? What you needed? Then walk away clean.
  14. People have needed art to survive ever since people were a thing. They still need it now. Writing is not a frivolous pursuit, and it does not have to hold second place to more ‘secure’ occupations. It is useful. It is effective. People choose who to marry based on whether they’ll listen to Beowulf quotes or whether they know how to use semicolons (both true stories). People go to war over holy manuscripts. For some people, the right book at the right time is worth hundreds of dollars of therapy. Make art, heal people.
  15. Which reminds me: there are a lot more Anxious Nuggets out there than I ever thought there were. The number of betareaders who have given me feedback that amounts to “but you’re actually writing about me” is still mindboggling. There is truly something to be said about being vulnerable in your art. There is something to be said about revealing the most deeply personal struggles you’ve got on paper. Chances are, you’ll get a resounding “me, too”.
  16. About #11 on this list. The quote is a quote from the book. The day I finally release the full manuscript to the public, all of my friends will realize I quote my book at them daily and just never say it’s what I’m doing. I’m telling you now: I quote my book always, and I don’t think there’s a single self-aggrandizing or egotistical thing about it. The book is my search for questions and answers and life philosophy distilled into little well-worded bite-sized aphorisms–why wouldn’t I use it as a reference? Quote your own writing. It’s one of the highest acts of self-affirmation you can perform.
  17. Sometimes it takes a major life change or a near-death experience to finally learn your lesson. Sometimes it takes a ship across an ocean or a month living in a caravan or an almost-fatal slip into a slot canyon to shake you awake. But sometimes, it’s as simple as someone looking at you, dead in the eye, and saying “You are a good person, and everybody forgives you.” As often as possible, be that person for others. They need it as much as you do.
  18. Apparently, writing a 150,000-word book is a Big Deal. Even one that isn’t completely edited yet. I am still surprised when people are surprised; I am still bemused when they are impressed. I honestly thought it was just what everyone did with their free time.
  19. I almost named this list–and this blog post–“19 Lessons I’ve Learned From Writing My Book”. I changed it last-minute. Because I’m not done learning them yet. I’m still in the process, over and over. There is a difference between understanding, logically, intellectually, and internalizing. There is a difference between knowing and Knowing. I’m not done yet. But I’m well on my way.

What about you? What lessons are you learning from your art? From the art of others? I’d love to hear about it in comments!


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