How not to write a (non-fiction) book

My Google Drive has five different folders with five different Slides documents that lay out a concept for five different books. Books that never got written. So, in 2016 when I created the sixth one I should’ve known that I wasn’t approaching this book-writing thing in the “right” way. Four years and eleven drafts later I can confirm that my approach was indeed, imperfect.

A few people have said that they’re interested in writing a book and have asked for my advice. With my confession above you’ll understand why although it’s incredibly flattering it is also quite funny to me. I sadly can’t tell you how to write a book — because I haven’t managed to finish mine just yet but I can definitely tell you how not to write a book. I hope that at least my mistakes help you save time, sanity, and hopefully prevent a few unnecessary grey hairs and panic attacks.

Do not start by writing your advice

I thought that if I close my laptop and sit with a pen, paper and a big question to answer I will write the book. I held the belief that the book you need to write is in your head so you just need to find the space to do “deep work”, as Cal Newport calls it, and the book will get written.

What I have learned through this process is that this is an incredible way to get words, wisdom and advice out of your head and into words but it is not how you write a book. A book is not just your processes, beliefs and thoughts. A book has story and narrative. Yes, even a non-fiction book (who knew?). I have learned that to write a book you might be better off starting by looking outwards at the masterpieces of the type of book you are writing to understand what is the story at the heart of a good piece of nonfiction.

This will help you craft your overarching story and the emotional journey you want to take your readers on. If this is your first piece of non-fiction you are likely writing about your own journey. If that is the case, think about what is the journey that you have been on, emotionally, to get to the point of writing this book.

Questions to ask yourself might be:

• How did I feel at the beginning of my journey?
• What were some pivotal moments in this journey I’ve been on?
• How did my childhood and pivotal events throughout my life inform this journey?

Do not “cut to the chase”

We are taught to make things shorter. Snappier. More concise. While this is true for headlines, tweets and billboards it is less true for books. When someone sits down to read your book they have chosen to make an investment in you and expect that by doing so you will grant them a ticket to your inner world and your story.

You might think that it’s better to cut to the interesting bits but if you reflect on your favorite books I’m sure you’ll agree that the majority of the narrative is building up to the “interesting bits” and without the setting, understanding the characters and the wider context those “interesting bits” wouldn’t be so interesting after all.

Writing a good book, I have come to learn, is an act of true vulnerability. You have to be willing to share your story — warts and all — so that your readers trust you to impart your wisdom.

Questions to ask yourself:

• What were the most painful parts of my journey?
• What are the parts that I am embarrassed and ashamed of?
• Where did I falter?
• How did this result in getting me to where I am?

Do not go with the flow

All (good) books are stories and all (good) stories need a strong foundation. The foundation of a good story is its structure. By working with a Story Grid editor, Parul Bavishi, I have learned that aside from the obvious — that the story needs a beginning, a middle, and an end — each of these sections also needs to abide by “The Five Comandments” which are five key components of any scene or sub-section.

Those five are: Inciting incident, Turning point/progressive complication, crisis, climax and resolution. An inciting incident is the event that catalyses the rest of the story. The progressive complications are the events, emotions and actions that add flavor to the incident. The crisis is the fork in the road. A crisis can either be a situation where there are two, incompatible good options or two bad options. The climax is the (surprising!) way that the protagonist responds to the crisis and finally, the resolution is a surprising but inevitable result of the inciting incident. Here’s a very strange example that I wrote without thinking beforehand:

Example Five Commandments of a Story

Questions to ask yourself:

• How could you map out the beginning, middle and end in a sentence or two?
• What kicked off your journey on this path?
• What was the moment that you could not go back? The “point of no return?”
• At the end, what did you “win but lose” or “lose but win”?
• Do you want to learn more about Story Grid’s structure? This is their most comprehensive book.

Do not expect that writing the first 50,000 is difficult

I thought that writing a book meant writing 50,000–80,000 words. Oh how I was wrong. A book is unimaginably more than the words it is comprised of. I think people had told me beforehand that the editing and rewriting was going to be the hard part but I never truly believed it.

I thought that I was different and that this book is different and that I was going to be fine. Honestly, to write a semi-OK “how to” guide of advice it would have been different. However, writing something with vulnerability, story and advice requires multiple layers of thought and writing.

I think of it like a masterpiece oil painting. It simply cannot be done in one sitting. There is the foundational layer, background, multiple layers of color, different brushes needed for different components, additional tools used to add texture, the time needed to let it dry in between and so on. Finally, the image also needs to be curated and displayed. The first 50,000 words are perhaps the first few colours used with no overlapping. I think that if I had truly understood this I would have been better prepared for the emotional and physical journey of writing something comprehensive.

Questions to ask yourself:

• How “good” do you want this book to be?
• What is your objective with the book?
• How much time are you willing to invest in it?

Do not go somewhere hot to write

My lifelong dream was to find a palm-lined surf town to write a book. It seemed idyllic. Ocean breeze, surfing in between writing sessions, tropical fruits and local coffee to fuel my day. After saving as much money as I could, in the summer of 2018 I decided to fulfil my dream and booked four months on the Pacific coast of Mexico to write my book away from the distractions of daily, city life and a job. With the beauty of hindsight on my side I can tell you that having a $20 nightly budget for accommodation, in the middle of summer in an equatorial beach town is not a way to be productive.

Without A/C I ended up waking up at 4:30am, writing ’til 7am — when it got too hot to think — and spending the rest of the day doing not much at all. The memory of my time in Mexico will always be one of the best of my life but it was definitely not the most productive. If you have the luxury to take a chunk of time off of work to go somewhere else to write then think about what you realistically need to make that productive. Probably cool-enough air (whether A/C or naturally), good internet, a comfortable desk-chair workspace and somewhere that is quiet at nighttime so you can get a good sleep. These seem obvious but I think I would have had a better time on my “writers retreat” if I thought a bit more about the practical aspects.

Questions to ask yourself:

• In what setting are you most productive?
• What are non-negotiables for productivity?
• Would it be helpful to be somewhere with a coworking space? If so, Nomad List may be helpful

Do not be set on self/traditional publishing

I was absolutely sure at the start that I wanted to go down the self-publishing route. Traditional publishers can take years to get your book out; they pay you hardly anything; and if you’re a first time author they will likely put very little marketing investment behind you. I figured, if I’m writing a book about how to turn ideas into products/services and make those products/services famous then I should be able to market and sell my own book. Plus, Amazon’s publishing platform makes it incredibly easy to the point that you don’t even need to pay to print books in advance of people buying them.

But then I had to take a step back and ask; what is my bigger life goal that writing this book is contributing to? Personally, I would like to work as an author full-time one day. To do that, having an agent and publishing contract could be a considerable step in that direction. Although elements of the traditional publishing model are outdated and archaic it still is the model. We don’t truly have a Spotify or Soundcloud for books…yet. To be honest, I’m still not sure which route makes most sense for me or whether I even have much of a choice. I’m currently speaking with an agent while also finishing the manuscript and book cover to self-publish so let’s see how each of those options pan out. I’m open to either and can see the benefits of each.

Something else to note is that if you are certain you want to follow the traditional publishing route and do not have a sure deadline then you don’t need to write the manuscript first. You can create a book proposal that you will use to “query” (publishing lingo for pitch) an agent. I personally really loved this book, How to Write a Book Proposal (Amazon link), which helps you lay out your book proposal and effectively pitch agents. Using it enabled me to get two meetings with agents (out of six queries) that I likely wouldn’t have got otherwise.

Questions to ask yourself:

• What is your higher-level goal that writing this book is contributing towards?

Writing a book is a serious endeavor. It’s an emotional roller coaster and a serious test of grit and ego and I’ve needed an endless list of professional resources, support from total strangers and the books I’ve linked to in this article to help me on my writing journey.

Full disclosure, they are all affiliate links. I’ve never used the Amazon affiliate program before and I’m not sure what % of the sale I would get if you made a purchase but as I mentioned, my goal with writing is to be able to do it full time and I’m exploring whether affiliate marketing can help support that. If you’d rather buy direct from your preferred book seller, please do. If you can buy them from an independent bookstore, even better. Good luck with your writing and please reach out if you have any additional questions.