From Medium to Book Deal in 12 Months

I’ve been blogging since the 80s. Okay maybe not that long. But starting around 2004, I launched and abandoned many blogs, and would continue to do so over the next decade. My first blog was called TheDirtyDirty.com — referring to the dirty south since I was living in Atlanta at the time, and not porn, as my father thought.

Sidenote: Sometimes I kick myself thinking about how much further along in my writing career I’d be if I hadn’t kept quitting things, but that’s neither here nor there — except to be a lesson to whoever’s reading this: stop quitting things.

I abandoned TheDirtyDirty when co-workers started reading it and tried to blog anonymously — but that was no fun. I started a lifestyle blog or two, a design blog here and there and a few others I don’t even remember.

In 2013, I finally started to take my interest in writing more seriously and committed myself to stick with a blog, any blog. I started Oolalove — a parody of Cosmo and other women’s magazines with articles like “Will He Cheat on You a Sixth Time? Take the Quiz.” I got as far as amassing a good number of finished articles, a long list of article ideas, and even hiring a few writers, before I once again abandoned it.

A year later, while cleaning out some storage, I found an 8-year old notebook from my days at Yahoo!. In it, I had scribbled “how to look smart in meetings.” Below that was the first idea — draw a ridiculous Venn diagram, and, below that, “if someone says 25%, say 1 in 4.” I immediately remembered writing this on the daily commute from San Francisco to Santa Clara, and how I always felt like I should do something with it but never did.

I took the ideas and turned them into a satirical list of things you could do to appear smart in a meeting.

I didn’t have a blog at the time so I posted my article, 10 Tricks to Appear Smart in Meetings, on Medium, a relatively new blogging platform at the time. By the next day it had over 200,000 views.

Sidenote: This all happened from an idea I scribbled in a notebook 8 years ago but did nothing with. Don’t judge your ideas! Put them out there. You have no idea where they could lead.

Did I have any idea it would go viral? Not a clue. Did I do anything special to help it go viral? Nothing. By the end of the week it had a million views and — as anyone who’s ever had anything go viral can attest to — it was exhilarating.

In the weeks that followed, I was rapidly gaining followers on Medium and Twitter and was kicking myself for not having my own blog where I could be building an audience. So about a month later, TheCooperReview.com was born.

I chose The Cooper Review because I was inspired by my favorite show The Colbert Report, and one of my favorite blogs, The Borowitz Report. The name had three things I wanted:

• It held some attachment to my name without being just my name, so if I want to hire writers in the future I can
• It was generic enough so I could write about things other than corporate humor
• The URL was available

Sidenote: Creating something from nothing is hard. You have no idea what’s going to come of it and there’s an annoying voice in your head telling you it’s all a waste of time and no one will look at it. Acknowledge those voices, and then ignore them.

If you’re just getting started, go to a place where there is a built-in audience that has native sharing. Don’t start with a domain. Start on Medium, Facebook, Instagram and experiment. (Chaz Hutton grew his audience on Instagram from nothing to over 100,000 and has a book coming out now, too) When your audience starts to grow and you start to find your voice, then get that domain.

Leaving My Job

Even with the success of my article and the growing popularity of my new blog, the decision to leave Google was hard. My fiance, my friends, my family, even my therapist, thought I should stay. The hardest thing about leaving was that I wasn’t unhappy. I loved my team, my role and going into work with my fiance everyday (that’s where we met, cue aww’s). I also wasn’t sure I was ready yet, considering all I had going was one viral post and a few hundred website visitors.

But as my passion for writing grew, my passion for my job dwindled. And as a manager with a growing team to motivate, I increasingly felt like a fraud.

The success of 10 Tricks to Appear Smart in Meetings continued — soon I was doing a few tv appearances and getting excited about the possibilities. Now, TV appearances isn’t the norm for most bloggers but you never know who’s going to contact you when you put yourself out there.

After working on The Cooper Review for three months while at Google, I decided to take the leap. Looking back, it was probably too soon. There are a lot of things I was doing and could’ve continued to do while I had a full time job, and it was hard to be creative with the mounting pressure of producing income.

I would wake up in the middle of the night with a panic attack not sure if I did the right thing. I briefly had a plan to tell my manager I changed my mind. But in the end I went through with it.

The first few months were the hardest:

• I was worried I’d never write anything as good as the meetings article
• I wasn’t growing my audience fast enough
• I’d agonize over each new thing I’d publish
• I’d agonize over each person who unliked my Facebook page or unsubscribed from my email list
• I had no idea how I was going to sustain this
• I was assuming I’d be back at Google in 6 months (which, honestly, wouldn’t have been the worst thing)

Around the height of my worry, I started putting together a book proposal. It was called “Conquering Corporate America,” and would be a collection of my online posts plus new material. I was planning to go the route of cold-emailing agents on a list when something else happened.

Attracting a Publisher

A few months after leaving Google, I was cobbling together a publishing schedule and learning things like:

• The best way to present my content (I finally chose this Wordpress theme)
• How to create a logo and brand for my site
• What to put on my about page (This example helped a lot)
• The best way to send out an email newsletter (I finally chose MailChimp)
• What to put in my email newsletter and when to send it (I still have no idea)
• How to build my Facebook and Instagram audiences (by posting consistently)
• How to make sure my website was fast (I finally found Flywheel)
• How to make some extra money with merchandise (Zazzle was the quickest to set up)
• The benefits of making sure my content was on my site, Medium, Huffington Post, and anywhere else I could put it

I started studying the success of one of my favorite online comics, The Oatmeal. I really wanted to learn how to draw and make my posts more visual but I absolutely sucked at drawing. I didn’t have the patience for it. When I got a Wacom tablet for Christmas, I began to try to turn my 10 Tricks article into an illustration, but nothing I did looked right.

Finally I decided to simply trace stock photos. You can read about my “technique” here. I was embarrassed that I wasn’t drawing freehand, but at the same time, something about turning these cheesy stock photos into illustrations really worked.

I re-posted 10 Tricks to Appear Smart in Meetings with illustrations on my site on January 31, 2015 and it went viral again.

Sidenote: Don’t be afraid to re-post that text article as an infographic, or that infographic as a cartoon, or that cartoon as a video. I had this voice in my head shouting “No! You need to create something new! If you re-post this people will think you’re a lazy hack!” which, might be true, but if I hadn’t re-posted it as an illustration this lazy hack wouldn’t be writing this article right now.

About a month after posting it, I started getting emails from publishers and literary agents interested in turning the post into a book.

Finding a Literary Agent

Two things will make it easier for you to find a literary agent:

• A publisher who’s already interested in a book
• An established audience

It was tempting to just go with the first publisher and agent who were interested but I decided to take my time and not rush it. I wanted to make sure I considered all my options, so I decided to get as many options as I could.

Sidenote: I only briefly considered self-publishing for this book. I read about some authors who published their first book(s) with a publisher then self-published later, and I read about some who successfully self-published then took their book to a publisher later. You can make a lot more money self-publishing but since my audience was small I felt going with a publisher might help me reach a bigger audience.

My husband contacted a former colleague at Audible (Hi Christina) who knew several literary agents. I sent her my idea for the book and she sent me the contacts of four agents who she thought might like it.

I sent an email to each of them. Only two wrote back, but #1 on the list wrote back immediately and she loved my idea. But she didn’t just sort of love the idea, she loved it enough to have already shared it with her friends and family, get on an hour long call with me to talk about it the next day and meet me for lunch a week later.

When I met her, we talked for 3 hours; about the book, about all the other ideas I had, my goals for my career, and everyday life stuff, too.

Sidenote: It’s important to have a real connection with your agent. He or she is going to be your champion, fighting for you and your work every step of the way. You don’t want someone who’s lukewarm about you. You need someone who wants to be your partner for this book and beyond.

So in the end, I didn’t have to write cold emails to a list of agents.

Advice I can give you based on my process:

• Publish your work everywhere
• Develop your brand and your voice
• Get interest from a publisher
• Ask friends and family for agent contacts
• With those potential agents, share your idea, the publishers who are already interested and the size of your audience (a mini-proposal)
• Find someone you connect with, who is a fan of the book and you

And now a huge shout out to my agent, Susan Raihofer at David Black :-)

The Book Proposal

Susan sent me several book proposals as examples which helped me get started. I shared with her the idea of doing an entire book on meetings and she loved it. So the idea went from “Conquering Corporate America” to “100 Tricks to Appear Smart in Meetings” and I began work on the proposal.

We wanted to make the proposal look and feel like our vision for the book. Since I saw the finished product as a small, squarish book, I laid the proposal out the same way. I put as much sample content in there as I could, as well as all the standard stuff (you can see what goes into most non-fiction proposals here), but I tried to keep the tone of the book consistent throughout, even when I was writing about my audience or competitive titles. It took me about 3 months of working on it off and on to finish it.

In June 2015, it was ready to be submitted to publishers.

Susan handled the entire process of choosing which publishers to submit to and coordinating with the ones who were interested. Twenty-four publishers received the proposal and we heard back from 20 of them.

And here’s where my experience becomes really “non-standard.” So many publishers were interested that it was now up to me to figure out who I wanted to work with.

Money was a big deciding factor, but so was vision. One publisher wanted the book to be as straight satire as possible — meaning some people wouldn’t even be able to tell it wasn’t serious. Another wanted to broaden the topic so it wasn’t just about meetings. Another wanted more text, less illustrations, while still another one wanted the opposite.

A few publishers were interested in another idea I had put in the proposal — the idea for a “corporate coloring book” — where readers could color in low-hanging fruit and someone getting thrown under a bus.

One publisher was interested in that plus a third book.

I had conference calls with about 14 different publishers, and yes, several of them tried to use my own meeting tricks on me.

We ended up going into a few rounds of auctions before I made my decision. (Auctions were basically one round of bids for the book which whittled the list of publishers down to 6, and then another round which left us with 3, based on the largest bids).

The most difficult decision was whether to go with a humor publisher or business publisher. I ended up going with a humor publisher for a few reasons:

• Although I love when satire is accidentally taken seriously, I didn’t want to take that chance with this book. So it was important for me to make sure people knew this book is supposed to make you laugh and very obviously a humor book.
• Long-term I want to write more humor, but not necessarily more business humor, so I felt that going with a humor publisher would help with that.

With that, I signed a 3 book deal with Andrews McMeel — 100 Tricks to Appear Smart in Meetings, Draw What Success Looks Like Coloring Book, and a third to-be-determined book with an equally long title.

Publishing Your First Book

On October 4th, 2016, my first two books will be published and it is exciting and terrifying.

If publishing a book is one of your goals, my advice is:

• Write
• Share your writing
• Build your audience

It doesn’t matter if you are discovered (which, with enough of an audience you will be) or if you put together the beginnings of a proposal and cold-email a list of potential agents, you need an audience. Your audience is more important than your idea.

Over time you’ll start to see what type of writing resonates with your audience. You’ll start to enjoy the creative process more. You’ll start to learn basic marketing to collect email subscribers and build a social following. You’ll stop agonizing over promoting yourself and your work.

And when you show up every day, take your ideas seriously, and focus relentlessly on your goals, book publishers will be fighting to get your attention.

Sarah Cooper is a writer, comedian and creator of TheCooperReview.com. Her first book, 100 Tricks to Appear Smart in Meetings comes out October 4th.

Many thanks to Tam Pham, Katie Fritts and Karen X for editing and advice with this post.