Case Study: Designing a Banner for Jack the Wrinkly Writer

Our design process for creating illustrated profile banners.

Mar 13, 2026

We are a mother-and-son illustration team. Our drawings are hand-drawn and traced in the computer. Our goal is to help Substackers illustrate their publications with fun and simple drawings. We’re trying to restore the human creativity that is being lost from the progression of technology and AI.

In last week’s post, we announced a new AJ Doodles service: Illustrated Social Media Profile Banners.

This week, we will take you behind the scenes and into the design process for a profile banner made for Substack writer: Jack Harmer the Wrinkly Writer.

Through Substack, Justin and I have been connecting with Jack for several months now.

You know how it is, when you’re reading someone’s publication, you start to get to know them. You recognize their tone, what they are passionate about, their sense of humor, etc.

From reading Jack’s publication, we were aware of his tell-it-like-it-is writing style. As we worked with him, we learned more about the direction he wanted to take his writing and his intended audience.

Before we getting into our design process, we asked Jack to share about his writing.

Jack the Wrinkly Writer

by Jack Harmer the Wrinkly Writer

My Substack newsletter has two main focus areas:

Young men under 30 who struggle with speaking to people in person.
Retirees who’ve lost their sense of usefulness and identity after leaving their careers.

My interest in writing for these two groups comes from a lifelong urge to help others find their purpose. Whenever and however I can. Over the years, I’ve given business advice to hundreds of clients, and in doing so, became fascinated by how differently people think, act, and make decisions.

Later in life, while studying for a degree in secondary teaching, that curiosity only deepened. I’ve always loved watching people grow, change, and find their footing. Being even a small part of that process.

Since retiring, I’ve also been learning the craft of fiction writing. My favourite genre is detective mysteries and thrillers—no surprise, really, since I’ve always had a curious, analytical side that likes to dig beneath the surface.

The Design Brief and Goals

We gathered information about Jack’s preferences through Substack direct messaging. Jack had clear ideas about the color and text. He gave a couple of ideas for the illustration.

1. A cartoon of an “old bloke” on a soap box talking to a bunch of “young blokes”

2. A cartoon of Jack sitting in an arm chair

3. A cartoon of Jack talking to some friends

As we messaged about his illustration ideas, it became clear that Jack’s preference, as well as ours, was #2—Jack sitting in an arm chair.

Here’s a list of our design goals:

Communicate Jack’s authentic style and wisdom.
Make his profile feel friendly and inviting.
Design a unique banner that was personal to Jack.
Give Jack a banner he was happy with.

My First Sketch

by Amy

As with all my illustrations, I started sketching with a pencil. Once I felt good about my lines, I took out my black felt-tip pens, traced, and added details.

When I asked Jack what he thought about it, he said, “The concept is great. But if it matters, I slump/slouch when I sit. I just chat, never lecture. Your great sketch made me think I was either sitting in a dentist waiting room or waiting for judgment outside the school principal’s office.”

I appreciated Jack’s honesty. For me, I thought the sketch made him look eager to chat, but for Jack, if felt like waiting for the dentist or a principal. Yikes! Art is all about how it makes us feel. I certainly didn’t want my illustration to evoke those feelings.

Jack sent an additional message saying, “I do love the socked feet.”

And I did too. 🧦💕

So with a this feedback, I drew another sketch.

My Second Sketch

I asked, “How’s this?”

Jack said, “Love it. Still love the socks.”

It was time to hand over my drawing to Justin.

Know a friend who would enjoy this post?

Tracing and Sketching

by Justin

Tracing over the sketch lines is a tedious task. I connect my basic drawing tablet to the computer and draw the new lines.

As I’m tracing, I adjust the lines, making them smoother and neater. I choose different sized strokes to add character and differentiate between elements.

This process makes the original drawing digital and editable.

Once the outline is complete, I then add color.

Colors, Fonts, and Layout

Jack told us that he wanted to use a midnight blue in the design. Midnight blue represented a new beginning to him.

I added a rectangle with the optimal dimensions for a Substack profile banner.

Next, I colored the illustration.

It’s important to add the background color first, then make color choices for the illustration based on the background. This way the colors all harmonize. Nothing stands out like it’s not supposed to be there.

At this point, Jack looked like he was just floating in his chair. I needed to add something.

To fix the problem of the floating chair, I added a couple of rectangles to act as a floor and baseboard.

Keeping colors to a minimum for the sake of simplicity, I made the floor tan.

One last thing, the text.

I wanted to use a serif font that felt slightly old-style but still clean and readable. I went with DM Serif Display. To complement the header font, I used DM Sans.

Here’s the final design…