The Ne'er-Do-Well

The Ne’er-Do-Well is a literary magazine that publishes what they lovingly refer to as “misfit lit.” The magazine is operated by Sheila Ashdown, a professional writer and editor, and proudly self-proclaimed book nerd.

My contributions to this project include: Creative Direction, Visual Design, Web Design, Illustration, Character Design, and Photography.

Sheila wanted to create a website and brand that spoke to the “oddly universal experience of feeling like the odd one out,” and the challenges writers often experience in pursuit of their craft (things like writer’s block, crippling self-doubt, “get a real job” mentality, and other writerly tribulations).

So, we embarked on a journey to discover how to convey that in a way that was clean, cute, lighthearted, and contemporary (desired traits identified in our discovery phase). 

The concept that hit all the desired targets was that of a black sheep pirate named “Black Baaa.” The concept is literary (pirates), personifies the feeling of being the odd one out (a black sheep), and represents the ethos of “misfit lit” (also pirates). 

Skull & Crossbones

How do you visually combine the pirate theme with the experience of frustrated writers? With a skull-shaped crumpled-up typewriter page over broken pencil crossbones, of course! I whipped up some sketches of this concept, showed it to Sheila, and got an enthusiastic “YES!”

The Birth of Black Baaa

So, what does a black sheep pirate look like? Who knows?! I consulted my sketch pad for the answer. What you see below are some of the sketches that became the final design for Black Baaa the Pirate. 

The Kraken

Every good hero needs a villain, and what better villain for a black sheep pirate writer than a discouragingly critical kraken? 

During the discovery phase, Sheila realized that she's drawn to sites that have “scenes.” So I created a scene for the footer of her website with Black Baaa’s ship battling a discouraging kraken (who apparently only reads bestsellers and thinks Black Baaa’s writing sucks). 

That kraken is clearly kind of a butthead. This was the process of creating him. 

Updated Kraken Illustration

When we updated Sheila's website to launch v.2 I reworked the footer illustration for use as a hero image.

Website Design

Facebook Cover Image


  Sheila Ashdown  Founder & Managing Editor

Sheila Ashdown
Founder & Managing Editor

  Grace Gallagher  Editorial Assistant

Grace Gallagher
Editorial Assistant

Client Testimonial

Before I started working with Ryan, I felt aimless and stressed about my website project. I’d worked with three other designer/illustrators and was never completely happy with the outcome—mostly because I wasn't able to fully articulate what I wanted. (I’m a writer—not so great with the visuals.)

Then I found Ryan, and he totally rescued the project for me. He started with a thorough discovery process that was unlike anything I’d experienced with a designer. He asked all the right questions and had a seemingly magical ability to draw out ideas that I didn’t even know were inside me. And he really listened. The theme he came up with (a literary black-sheep pirate) was totally spot-on. As soon as I heard it, I thought, 'I didn’t know that I wanted a black-sheep pirate theme, but hell yeah, that’s exactly what I want!' I laughed with delight for about 5 straight minutes when he presented it to me.

Honestly, I get a little emotional looking at my website, because I’m just so thrilled and delighted with it, and have gotten nothing but enthusiastic feedback. He put such heart and care into my project, and I feel grateful to have found him.

Sheila Ashdown
Professional Writer and Editor