Adobe MAX is right around the corner! As a Creative Resident, I’ll be giving a presentation (twice!) called Adventures in Book Publishing. It’s a dream for many designers, illustrators and writers to see their name on the cover of a book. I’ll be giving an hour long talk where I share my story as well as answer some questions to help aspiring authors get started. Questions like…

Do I need an agent? Should I go with a traditional publisher, or self-publish? How much money will I make? How long does it take? What can a book do for me? Should I share my ideas online? What’s the difference between a query and a proposal? …and more.

I hope this provides clarity to what can seem an ambiguous, arduous undertaking.

Not going to Adobe MAX? Sign up to view the keynotes online. I’m going to try to Periscope my talk. Will keep you posted! Follow the fun. 


Hi Brooklyn,

Please join Adobe, Makeshift Society and me for a night of Exquisite Totes next Thursday, September 24 from 7-9.

We’re paying homage to exquisite corpse, a surrealist game dating back to the early 20th Century. Artists would pass around a piece of folded paper and write a word that would become part of a collaborative sentence. The name comes from one of the first sentences, translated to, “The exquisite corpse will drink the young wine.” It’s also fun to play with pictures, and now totes.

I created a series of monster heads, torsos and legs. During the event you’ll be able to pick one of each to create your own monster for a tote. There will also be drinks and light bites.

Purchase your ticket here. Even better, take 50% off with coupon code ‘friendsof’. 

See you soon!


Only a couple more weeks left of my September Tattly bonus! I designed this pup with the Adobe Creative Residency. It’s the next best thing to having a real tattoo, and you even have the opportunity to reenact this scene. How it works: order any Tattly(s) from the site and you’ll receive this pup with your order for free.

If you’d like to see how I created it, check out this tutorial I wrote for the Tattly blog.

becky-simpson-flower-tattlyPhoto by Tattly, worn by my groovy biz mentor, Nic Annette Miller

Hello, all! I’m leading a workshop at Yellow Conference this week and here’s a handy list of resources I’ll be directly or indirectly referencing. I hope you find them helpful!

TED talks
Your Body Language Shapes Who You Are  Amy Cuddy
How Schools Kill Creativity Ken Robinson
On finding meaning in your career Steven Tomlinson

Blog posts
The Most Important Thing I Ever learned (Life unfolds in moments) David Cain
Focus on the Growing Heap, Not the One Coin Gretchen Ruben
The Complete Guide To Not Giving a… Julien Smith
Productivity Hacks Tim Ferriss
1000 True Fans Kevin Kelley

Mindset Carol Dwek
Breaking the Time Barrier by Mike McDerment and Donald Cowper (I read this on my flight home and I can’t recommend it enough. It’s a must read for all small business owners)
4-hr Work Week Tim Ferriss
The E-Myth (Revisited) Michael Gerber
Rework Jason Fried & John Heinemeier
99U books

Online classes
B School

Apps (for designers)
Adobe Shape (vectorizes projects from your phone)
Adobe Color (capture real life color palettes)
Adobe Draw (drawing pad for ipad or iphone
Scanner Pro (awesome scanner from your phone)

Time management & organization
Harvest (time tracking)

Virtual assistants:
Fancy Hands
Virtual Miss Friday
(also, just search “creative virtual assistant” or “design virtual assistant”)

Posts on book publishing
Adventures in Book Publishing Pt. 1
Adventures in Book Publishing Pt. 2
From Blog to Book
“So you want to write a book” video from Jay Papasan (so good!)

Howdy, lettering and drawing nerds!

I finished up 100 Days of Getting Started last week. This is the first completed project during my creative residency.

Celebration is lovely in theory but most of us hardly make time to commemorate important milestones because we’re too busy moving on to the next thing. Not this time! I decided to celebrate with a rousing night of illustration at Studium. Lucky for me, Justin David Cox had hosted a lettering night in the past and was looking to do another. We combined forces and created a super party: Drawing/Lettering Night.

It was a real hootenanny. We drew, lettered and drank.

In case you missed it, fear not. We’re going to have another in September. Stay tuned!


I finished my 100 day project last night (if you haven’t read about this concept, head over to The Great Discontent to learn more). My project? 100 Days of Getting Started, inspired by Mark Twain’s quote, “The secret of getting ahead is getting started.”

I recently read this Tweet by Ugmonk founder, Jeff Sheldon:

Top 5 Mind-Blowing Secrets of Successful Entrepreneurs:

1. They don’t read clickbait articles all day.

2. They do the work.




(Slow clap)

We live in a world of information overload. We’re constantly forced to curate our lives, because we know that if we don’t, someone else will. We have more opportunities than ever, and we’re better than ever at sifting through said click bait links and YouTube videos. Those of us who have found our home in creative industries are also learning how to hone our skills, manage our time and coddle the vision that got us here in the first place.

We’re dreamers!

But that’s the double edge sword. We like to dream.

It’s easier to dream than work.

I feel a sense of FOMO rush over me every time somebody posts a book/blog post/podcast that was “life changing.” I want to drop what I’m doing so I can acquire this fruit from the tree of knowledge instead of doing the work that will instill valuable lessons of my own.

Before I started working for myself several years ago, my dad told me, “Your biggest struggle will be staying focused. Every business owner has to learn focus.” I didn’t know what he meant because I always thought my vision was clear: I wanted to work for myself doing graphic design and illustration. I wanted to be my own boss. What else was there to figure out?


After a couple of years I realize exactly how right he was. Productive procrastination runs rampant in any workplace. Crossing tasks off the to-do list welcomes a lukewarm adrenaline rush that can only be satisfied by crossing off more lukewarm tasks.

As I reflect on the last three months of art I’ve been creating for 100 Days of Getting Started, I’m oddly surprised by how much I learned by experience (those specific lessons learned will be on Adobe Inspire later this week).

Perhaps the biggest lesson of all was the reinforced advice my dad gave me that December: learn to prioritize focus.

The beauty of 100 day projects is that they don’t allow room for petty excuses or lack of direction.

At the end of the day, the only question that matters is: “Did I do the work today?” If the answer is yes, then you are inching closer to victory. If it’s no, then you have failed. However, knowing that each day is a fresh start is the most redemptive part of the project (side note: this is also how I survived golf in high school—new hole, fresh start). Doing this over and over makes you feel like Tom Cruise in Edge of Tomorrow for pretty much three months straight, and that’s cool because he saves the world from aliens…but I digress.

100 day projects don’t have to be complex, but they should be challenging. They’re meant to be practice, after all. With healthy practice, process and growth are celebrated, not perfect performance.

Projects like this teach us to hunker down and do the work. Unexpected consequences arise (a.k.a. lessons learned), but only those who do the work will be able to internalize these game changing lessons. It’s the ultimate, “You had to be there” for personal growth. The good, the bad and the ugly are all agents of change. They’re the warriors to bring us to the finish line.

What else is nice about working on something for 100 days?

You have 100 more of anything you want. In my case, it’s a slew of new illustrations.

Remember: baby steps.

What’s your project?

I need your help!

I’m nearing the end of my 100 Days of Getting Started project with my Creative Residency (reminding me that three months is not long at all). I’m excited to bring some of this art to life. Below are a few images I may print. Several of them would be edited / recolored / resized appropriately. Do you have any favorites? If you give me your feedback by Thursday morning (August 6), you may win a print of your choice from my shop. Also note: anybody who leaves feedback will receive 25% off the next round of prints (email to redeem). Let the games begin!


Welcome to the second installment of Adventures in Publishing. I know it’s been a little while since the last post on this subject, but it’s only because I’ve been working on The Roommate Book and 100 Days of Getting Started. Here I will go over some of the frequently asked questions in regards to book publishing. Note: these questions are tailored to traditional publishing, not self-publishing. Here we go!

When approaching agents, do I already need to have an online presence? Do I need to be popular?

The quick answer is yes and maybe, but not necessarily. The longer answer is this: publishers need to know that their author is invested in selling the book. You need to prove yourself. You have to show that you’re the book’s #1 fan when you’re promoting. If you don’t have a huge presence online, that’s okay, but the next best thing is showing that you’re invested in growth, or you have an audience that’s accessible to you.

When I was talking to agents about representing I’d Rather Be Short, I had 200 Twitter followers. Two agents didn’t care about the number of my followers—they said the idea was good enough to sell on its own. Another agent was skeptical. He said that in 2007 a good idea was good enough, but now publishers need to see followers and numbers. A friend connected me to a popular lit agent. This agent told me to call him when I had 15,000 Twitter followers. I said, “I don’t know how to get 15k in a couple of weeks.” He responded with, “On the Internet you can go from 0-60 in 15 seconds. You’ll figure it out.’” Needless to say I did not go with him, but he’s right. It matters. But it’s not the only thing that matters…so some would say he was also kind of wrong. My only blog readers at the time were my mom and Facebook friends. I didn’t report the readership in my proposal, but we did say that the traffic spiked whenever I posted a new I’d Rather Be Short drawing (this is true). It was sincere and it showed that even on a micro level, the project was building momentum.

If you do have a big following, that makes it much easier for agents and publishers to say yes. It shows that you’re already committed to the project and there’s already a market for your work. T-Rex Trying started out as a popular Tumblr blog and has been a wildly successful as a published book. My pal, Alida Nugent also had her work on her blog, The Frenemy before it became a book. She’s a fantastic writer (I can’t tell you how many times I laughed out loud while reading Don’t Worry, It Gets Worse…order it today).

Every situation is different, but as a rule of thumb I’d say this: you don’t need to have a huge following, but you do need to show that you can get your book in front of lots of eyes, and the best eyes come from your tribe.

Should I post my work online first? Or keep it quiet until I find an agent/publisher?

Again, there’s no “right answer” here. As a fast and very general answer, I’d suggest showing what you can without showing too much. You’ll hear arguments both ways. I say that because it’s safe and I think you can have your cake and eat it too. I posted a few “I’d rather be short” drawings on my blog as just a “side project” while I was looking for agents. I didn’t want people to know I wanted it to be a book because that’s way too much pressure for my tender heart. But I do think the accountability and momentum is important. I’d lean more towards oversharing than undersharing. There are plenty of ideas to go around. 1. Nobody is going to steal your idea and 2. You are not going to run out of good ideas. Tucker Max was rejected by over 500 agents, but he put his content online and it exploded. He soon had a book deal and remained on the NY Times Best Seller list for over 150 weeks.

Ultimately you know what the best route is for you and your project.

How do I know if my idea is any good?

Obviously “good” is subjective. Are you interested in every book at Barnes & Noble? No, but every book in Barnes & Noble was good enough to be published, according to at least a few people.

Just because what we deem uncool, boring, bad or lowbrow gets published does NOT mean that every idea—good or bad—is destined for publication. The question is, how do you know if your idea is good for publishing?

We’ll start with the obvious: your content is already gaining traction. Perhaps you already have a project, series or blog post that is connecting with a lot of people. This is a good sign.

What if you just have an idea that’s good, but no exposure to prove that other people think so too? Your turtle portraits haven’t gone viral, but YOU really think there’s something special to them.

It helps to ask the simple question, “Who would buy this?” or better yet, “For whom could this make the perfect gift?” In my case, everyone has a short friend. I’d Rather Be Short is a niche book. It feels unique—unique enough that a potential buyer could instantly think of a specific friend. For my second, The Roommate Book (comes out next spring), we’re shooting for the graduation crowd (hence the publication season). For the gals headed to college or leaving college to live in a new city with a new roommate, this is the perfect book. The net can be cast as wide as “friendship” and as narrow as “high school graduation gift for girls.”

Not every book is super niche. Some books have a broader appeal, and that’s okay too. Those probably connected or were sure to connect with a lot of people who thought it was really beautiful, funny, helpful or interesting.

I’ve had a lot of good and bad book ideas. One time I think I pitched an idea to my agent that was a book of quotes by famous people but on the adjacent page to the quote, the people where illustrated mermaids and mermen. It still sounds terrible and hilarious at the same time. It could have been great, but I couldn’t get past the initial question: who would receive this as a gift?

And that concludes our second installment of Adventures in Publishing. Thanks for stopping by! Do you have a book you’re dreaming about writing? Do you already have a book and want to offer further insight? Do you have any questions that haven’t been addressed? Leave a comment below or holler on Instagram or Twitter.

Want to read more on publishing? Check out the first post where I answer a few other questions.


Hello all! I’m chipping away at The Roommate Book one spread at a time. Here’s a modified version of said spreads.

I want to let you know that I’m regularly updating the home page of with new art that I’m creating for 100 Days of Getting Started (the 100 drawings I’m creating for my first quarter in my Creative Residency.)

Here’s why it might be relevant to you:

1. New art in any capacity is cool, right?

2. I’m jotting down my process / tools used for every new piece from now on (including the last nine).

3. I also include the original scan, unedited. It’s easy to highlight our process—to show on Instagram what we want people to see. This is the raw footage.

My hope is for this art to become a resource for aspiring illustrators or those looking to compare notes. Check out the rest of the page. I’m still deciding if I want to make the animals black or keep the white cutouts. Thoughts?

If you’re interested in these updates being delivered to you via email every other week, sign up below. I promise I will never send something just to fill the space. Also, a newsletter that’s 90% pictures? TOO EASY.

Biweekly art & notes

* indicates required

web-beach-people 1modest-pinup-girls

Do you know about the 100 Day Project? Read about it here on the Great Discontent.

We can accomplish great things when we do a little bit at a time consistently over time.

The first quarter of my Creative Residency is devoted to making art.

How do we make the best art? How do we make the worst art? How do we make any art?

We get started.

Like I said before, if there’s one thing I know it is that it’s better to start somewhere now than it is to start somewhere later.

And this is why I’ve been posting #100daysofgettingstarted on Instagram.

Mark Twain said it best: “The secret of getting ahead is getting started.”

My 100 Day Project will display 100 illustrations in varying degrees of completion. I’m updating the home page of my website (almost weekly) with new work, complete with original sketches and tools/process used. If you want to see more, check that out or follow me on Instagram.