9 Rookie Mistakes I Made When I Wrote My Very First Book Proposal (Don’t Do This!)

I'm the first to admit I love doing things trial by fire. Such a masochist! But it's true: I love being thrown into a tank full of sharks and then yelling, “COME FOR ME!” while simultaneously trying to figure out how the flipper to get out of there. (Haha, funny/sad?) I learn best this way—and in fact, it's one of my favorite ways to make progress faster than any other hobo out there. Don't start before you're ready: start before you've had time to decide either way.

So of course, what other approach would I have taken to writing the first draft of my very first book proposal back in 2015? While that first draft was absolute mediocrement, I learned a lot by writing it—and by subsequently working with my literary agent and editors to revise it. The end result? A six-plus-figure book deal with the world's biggest publishing house on the planet. (Yes, I almost fucking fainted.)

So what are the nine biggest rookie mistakes I made when I wrote that first draft? LEMME TELL YOU ALL ABOUT IT.

  1. Rookie Mistake #1
    Not being 100% clear on your message (and just knowing you want to “write a book.”) You musttttt get clear on this first. And I know, it sucks! You want to write! But you've gotta find your focus first. TRUST ME ON THIS. Don't try to make a million points with your book: try to focus on one big idea. When someone asks you “what's your book about?” you should be able to respond with one big idea. Other ideas can have their own book later.
  2. Rookie Mistake #2
    Not understanding that you can't just have a message—you need to have an argument. (See previous post on making 50% of your readers hate you.)
  3. Rookie Mistake #3
    Trying to make something “original” that would impressively marry multiple genres—such as memoir, self-help and business—not realizing that if an editor can't clearly figure out where your book fits, or how they can market it, it's a no. They're looking at your book and trying to determine where it goes on the shelf, and #PROTIP: that means that they'll be looking for a similar word count, look and feel, too.
  4. Rookie Mistake #4
    Trying to squish the content into a creative container/structure that feels forced and hackneyed. When done correctly, this can be awesome, but if it doesn't add to the value of your book, it's detracting from it. And the whole thing will feel disconnected and strained.
  5. Rookie Mistake #5
    Not wanting to spend the necessary time really fleshing out the entire book outline with care. Your proposal requires a proposed table of contents, with proposed chapter titles, and descriptions of each. It's a BIG job. And you know when you will procrastinate this? When you aren't 100% clear about what you're writing, what your book is about, and what your argument is. 🙂
  6. Rookie Mistake #6
    Trying to fit too much into one book. You need to keep it focused and pointed. My editor advises that you start with your main message and argument, and then reverse engineer your chapters from here—rather than sitting down and randomly brainstorming chapters you want to write and then trying to find a common thread.
  7. Rookie Mistake #7
    Not being direct enough with your readers. It's tempting to tell a story or an anecdote and assume that the lesson is implied, but you need to spell it out: what does this mean for them? What does this mean for any of us?
  8. Rookie Mistake #8
    Trying to be too cute and clever with the subtitle. Keep this to ten words or less! I AM THE QUEEN OF BEING TOO WORDY. Don't do that.
  9. Rookie Mistake #9
    Spending too much time not leveraging your strengths. At first, I wanted my book to be the most serious project I'd ever done in my life, so I took it very seriously and I tried to say serious things and write serious words. I ended up not sounding like myself at all! If you say “donkey balls” in real life, here is permission to say “donkey balls” in your book.

Foaming at the mouth for more insider tips? Here are ten more rookie mistakes that will royally ruin your shot at a book deal.

Want to take my course on how to get a six-figure book deal? Check that out over here!

Want to just buy the damn book already? Pre-order here.

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Quit your job. Work remotely. Travel the world. Find your f*cking self.

Every weekday morning at 8am Eastern you’ll get 3 ideas to help you make big moves and big money. Written by Penguin Random House author, entrepreneur & digital nomad, Ash Ambirge, who likes to believe she still has standards.

The Middle Finger Project has helped over 500,000+ unconventional subscribers ditch the crock pot & go on an adventure. Established 2009 from Santiago, Chile.

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