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5 Tips for Anyone Who Feels They’re Not Ready to Write Their Book: My Book Story

Hailey Dale


I’m Hailey – content strategist and founder here at Your Content Empire where we help you create more profitable, purposeful and productive content — and hopefully enjoy yourself more while doing it too. Learn more about me here >>

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5 Tips for Anyone Who Feels They're Not Ready to Write Their Book

I’ve always loved to write. I’ve kept a journal ever since I was six. I have so many novels I’ve started and packed away into boxes. I even pursued my English undergraduate degree because I felt most at home reading and writing about books. 

It’s hardly a surprise that from the time I started my business, I considered ‘publish a book’ the pinnacle of achievement. 

Where the idea for this book came from

Your Content Rebellion came out of observations I had of myself and my peers. I witnessed how much pressure we placed on ourselves when it comes to content. This pressure tends to sabotage even the best (and most ambitious) of content planning intentions. We as business owners need content to survive and nourish our businesses. The problem is there are so many choices/pressures/shoulds involved in a business that our relationship to content can best be defined as ‘it’s complicated.’

I wasn’t exactly sure where to even start with a nonfiction book. So I started with what I knew, creating a step-by-step process and turning it into a course. This was the easiest part of the entire book journey. 

The trouble I had taking it from idea to done

Year after year when I set my goals, ‘write and publish a book’ was front and centre on my goal cards that I created as part of Amber McCue’s annual event The Planathon. And every year, I met and exceeded every other goal on those cards EXCEPT the book. 

The book dream became my albatross, my white whale. An elusive goal that I seemed to have no hope of ever reaching – no matter what coaches I hired or booking writing programs I signed up for. In this area, I was a failure. 

What I know now

Even though I’m four years into the process now, most of the book has come together in the last year (besides the bits pulled from the course I created around the Content Rebellion process). 

What this has made me realize is that I wasn’t ready to write the book before. As Amber McCue says, “it’s right on time”. 

I know this is true because of the powerful stories and examples I can write about now thanks to these past years of work. I now have things I am including in my book that I wasn’t even aware of when I first started. Here’s the truth: the book wasn’t ready then and neither was I. 

If you’re writing a book, struggling to write a book or want to write a book, here are some of the very-hard-learned-lessons that I hope will save you some time and grief: 

Tip 1: Get an outside perspective

The thing that finally got me out of my own way was getting an outside perspective from someone I have 100% trust in. I was tangled up in my doubts before this – Do people need an intuitive and joy-fuelled approach to content strategy and creation? Who am I to give it to them? What if it sucks and my dreams of being an author are over?

But I booked an in-person book planning intensive with my friend Jodi Brandon who’s a book coach and editor for entrepreneurs. 

This got me over my sabotaging self for a couple of reasons: 

#1 – We came up with a chapter by chapter plan for the book and a project plan on how to finish writing it. I finally had a roadmap to follow. 

#2 – I got external validation that my ideas were worth sharing on this topic. I know, I know – we’re not supposed to need external validation. We should have enough confidence in our inner voice to push onwards. What can I say? This helped me tremendously. 

Tip 2: Figure Out the Right Questions

I think a lot of what intimidated me about a BOOK, besides the warranted-or-not magnitude I’d given it in my head, was that it’s such a BIG piece of content. Bigger than everything I’d ever written. My 80ish page Master’s thesis doesn’t hold a candle to it. 

What didn’t work for me? Sitting down at my desk to write a book. 

What did work instead? Making a list of questions for each chapter and sitting down each day to answer one of those. 

I tried to make the project as teeny tiny as I could knowing that my small bits would add up to something big.  

I have an unwavering belief that all pieces of content can be written using this approach. Check out this post to learn more about it. 

Tip 3: Content Interviews

Speaking of questions, another tool that I use in my agency all the time and finally pulled out for this project was content interviews. 

These are structured like podcast interviews. I tell my clients to show up and have a conversation with me about a topic they already know a lot about. I’ll ask them questions, dive a little deeper into specific details and pull stories. Then we get these transcribed and turned into pieces of content – usually blog posts, social media copy and emails. 

I’m a naturally curious person so I love getting to do these interviews with my clients. I never thought to turn the tables and interview myself. When one of my longtime clients in the Content Empire Mastermind told me she’d recently gone through the Content Rebellion program, it struck me that I should have her interview me! 

We met for 4 x 1-hour sessions to finish fleshing out the rest of the words needed to finish the final draft before revisions began. It was SO easy and I didn’t feel like a weirdo talking to myself like I do when I try to DIY these content interviews myself. 

Tip 4: Focus on Shorter Pieces of Content

Similar to shifting my focus from writing a whole chapter in one sitting to answering questions and using these answers to create my chapters, I think another great approach is blog posts and other smaller forms of content. 

If a book feels far for you right now, can you decide on 3-4 chapter sections, write them as blog posts instead and then add them into the book as chapters? 

That way you build an audience around the subject and can offer them the book later. 

One of my favourite books by James Clear (Atomic Habits) was written that way. As I read the chapters, I recognize the blog posts I originally read. Do I mind that it’s repetitive? Not at all. I’m absorbing information differently and seeing it framed in the context of a chapter. 

Tip 5: Race to the First Draft

Things moved quickly once I managed to pull together the first draft. It may have been an incomplete and pieced-together piece of crap, but it was a draft that I could work with. 

I stole from the program I created, from blog posts I had and the minimal writing I’d managed to do so far. It gave me a proper appreciation for where I was really at in terms of word count and it became a lot easier to identify what questions I still needed to answer (see tip #3). 

The magic truly is in the editing. As was proven to me when I say the increase in quality from draft one to draft two. 

Want to Check Out the Book?

If you’re struggling to make content work for you and are sick of fighting against yourself, check out my book Your Content Rebellion here!

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