10 books that will make you a working writer. (And why.)

Books that will help your literary start-up take off.

Shaunta Grimes
May 27 · 9 min read

I’ve been thinking a lot lately about the idea that every writer owns a small business. We’re all start-ups. Only, we’re also artists, and it can feel weird to do things like market your work.

I’m working on a new project that’s all about the idea of writing as a business.

Even when you’re doing a kind of writing that fits more neatly into a business model — like blogging — it’s so tempting to just publish and let the universe (and readers) dictate what happens.

It can also be super tempting to just decide you’re not ready for the whole publishing thing yet at all and skip the whole scary putting-your-work-out-there part.

But, once you get the mechanics of writing down, it’s time to think about why you’re doing all that work.

Chances are pretty good that you’re telling stories for other people to read and enjoy. If that’s true, then the bare bones truth is that you need to start thinking of yourself as not only an artist — but a business person.

Here are some books that will help you get a handle on that.

The Dip by Seth Godin

“A woodpecker can tap twenty times on a thousand trees and get nowhere, but stay busy. Or he can tap twenty-thousand times on one tree and get dinner.”

This is a tiny little book that packs a huge punch. It manages to be equally about sticking and quitting — and why each one is important in it’s time.

This is especially relevant to writers, because I see this happen so often: we get started on a new idea and as soon as we don’t know where it’s going or when the next great idea pops up, we abandon it.

There is only one hard and fast rule when it comes to writing. You have to finish writing the book. But also, sometimes, you have to know when it’s time to move on. (Just not too soon!)

The One Thing by Gary Keller

“Extraordinary results happen only when you give the best you have to become the best you can be at your most important work.”

Gary Keller’s book gave me goosebumps. He calls out things that either hold me back or make me feel so guilty that I quit as lies.

The huge one for me (and I bet for tons of his readers) is multitasking. He literally says: Multitasking is a lie. He gives scientific data to back that up.

It’s okay to choose your one thing (writing?) and pursue it like it is your ONE THING. In fact, you owe it to yourself and to the world. And if you frame your life around the idea of your one thing, then other things fall into place.

Turning Pro by Steven Pressfield

“The amateur dreads becoming who she really is because she fears that this new person will be judged by others as “different.” The tribe will declare us “weird” or “queer” or “crazy.” The tribe will reject us. Here’s the truth: the tribe doesn’t give a shit. There is no tribe. That gang or posse that we imagine is sustaining us by the bonds we share is in fact a conglomeration of individuals who are just as fucked up as we are and just as terrified.”

Steven Pressfield has a serious talent for saying what he has to say in a sticky way. In Turning Pro he makes the case for a mindset shift from amateur to professional. In a series of very short (mostly shorter than one page) chapters, he lays out his case and then tells writers how to make this free, but not easy, shift.

The Creative Habit by Twyla Tharp

“I guess that’s the real secret to creative preparation. If you’re at a dead end, take a deep breath, stamp your foot, and shout “Begin!” You never know where it will take you.”

My favorite chapter in this book is called “Before you can think outside of the box, you have to start with a box.” It just sings to the analog girl that I am. Tharp talks about how she starts every project with an actual box and fills it with things. And now I want to do that. I bet you’ll want to, too.

The Creative Habit is a beautifully written book about creativity and business told from the point of view of a woman who has had a spectacularly creative career.

How to Make Money with Your Writing by Joanna Penn

“Stop asking permission. You don’t need it. Stop waiting to be chosen. Choose yourself.”

Here’s what I love about this book: It’s super transparent. Penn talks about her own path to earning a living as a writer. And the punch line isn’t something like: Then I made Oprah’s book club . . .

This book is about hard work, and income streams, and looking at your writing work as a business. Penn breaks down where her income comes from, then talks about how other writers can build their own profitable businesses.

Make Art, Make Money: Lesson from Jim Henson on Fueling Your Creative Career by Elizabeth Hyde Stevens

“In many ways, Henson was a slave to his artistic gift — but to no one else. This is the ideal state for an artist.”

Stevens lays out ten lessons for artists (that includes us, writers!) from Jim Henson. Seriously, anytime you can learn from Jim Henson about having a creative career, jump on that bus. That’s really the magic of books, right? You can learn from masters for the cost of a sandwich.

Contagious: Why Things Catch On by Jonah Berger

“Marketing is about spreading the love.”

Marketing is a strange bird. I don’t know any fiction writers who enjoy it. If we had our way, we’d all spend all of our time creating new stories — and then people would just buy them. By magic. By osmosis. I don’t know. Just because we want them to.

Only it doesn’t that work that way.

We all know that. Jonah Berger’s book is a good primer on why.

If you’re a writer with any desire at all to have your work read, you need to know how virality happens, so that you can work with it.

The Art of Asking by Amanda Palmer

“Asking for help with shame says:
You have the power over me.
Asking with condescension says:
I have the power over you.
But asking for help with gratitude says:
We have the power to help each other.

Okay, so an undeniable punchline in Amanda Palmer’s story is this: and then my uber-famous husband Tweeter my Kickstarter link . . .

But, really, she has an important message here that writers (and all creatives) sometimes struggle with. Writers often hate asking to be paid. Sure, we want a big, faceless publisher to cut us checks. Or we want to put our book in a store with a price tag on it.

But actually asking our fans to become our supporters.

Ugh.

That’s HARD. Amanda Palmer makes the case that asking for support is really the art of letting our fans support our work.

Write to Market by Chris Fox

“If you want to succeed as an author you need to work your ass off.”

It’s really, really hard for me to even consider writing a book that’s just like other books that my readers have read, so that they’ll buy and read mine.

It makes the artistic part of my brain go a little explodey if you want the truth.

In fact, if I hadn’t met Chris Fox at a conference and actually heard him speak, and had the chance to talk to him myself, I wouldn’t have even considered reading it so that it could make it here at all.

Fox acknowledges in his book that writing to market is divisive. It’s a little scary. And some writers will hate on the idea without fully understanding it. He thinks it’s an important enough concept to have written the book anyway.

Fox is a data scientist. He’s figured out how Amazon works to get books in front of readers who want them. He talks about writing to market as paying dues, building a readership, so that later you can be more inventive and you’ll have readers already lined up to take that trip with you.

The number one problem that I hear from writers is that they’ve written a book they love, but no one is buying it. Write to Market does a good job of explaining why.

Amazon is the biggest book store in the world. Kindle Unlimited is the second. Seriously — it doesn’t make any sense not to understand how they work, regardless of how or what you choose to write.

Scratch: Writers, Money, and the Art of Making a Living by Manula Martin

“The reality is, more and more and more, being a writer is running your own business. While I’ve had salaries, and I’ve been an employee, overall and ultimately and certainly increasingly so, being a writer is running a small business.”

Scratch is a collection of essays about earning a living as a writer, written by people who are in the trenches, doing it.

There are essays about the early days of starting a career, being in the trenches, and what happens after you hit your tipping point and you’re actually DOING it.

It’s not like stories about writers and money are laying around on the ground. It can be really difficult to find transparent information about the nitty gritty stuff in this business. If you’re looking for that, you want this book.


Here’s my secret weapon for sticking with whatever your thing is.

(DISCLAIMER: This post includes affiliate links.)

Shaunta Grimes is a writer and teacher. She is an out-of-place Nevadan living in Northwestern PA with her husband, three superstar kids, two dementia patients, a good friend, Alfred the cat, and a yellow rescue dog named Maybelline Scout. She’s represented by Elizabeth Bennett at Transatlantic Literary Agency and her most recent book is The Astonishing Maybe. She’s on Twitter @shauntagrimes and is the original Ninja Writer.

The Write Brain

Posts about productivity, business, and systems for right-brained creatives. Ideas aren’t enough. We actually have to do the things!

Shaunta Grimes

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Learn. Write. Repeat. Visit me at ninjawriters.org (My posts may contain affiliate links!)

The Write Brain

Posts about productivity, business, and systems for right-brained creatives. Ideas aren’t enough. We actually have to do the things!