Every blog illustration I create is meant to visually embody the concept of a post.

While each one is different, the style is consistent, so that collectively our blog images help tell the story of the Help Scout brand.

And hidden behind the visual story I present is a backstory: One of tossed experiments, creative blocks (and the process of overcoming them), deadlines, concepts that don’t pan out, and every so often, a moment of satisfaction.

I’ve talked about the technical side of digital illustration before — how to use design tools, perspective, color and balance. But there’s another element to design that is actually the more challenging (and rewarding) part of my job as visual designer and illustrator for the Help Scout blog: coming up with ideas, then developing them into a finished product.

Reading into a concept

Any correlation between the title and the image creates a better, more cohesive experience for the reader, so, naturally, I always look to the post title for inspiration before I begin sketching.

If nothing stands out, I draw inspiration from the post: an analogy, an anecdote, or anything that I think embodies the post and makes a good visual. One example is the illustration for The Psychology Behind the Perfect Customer Interview.

The Psychology Behind the Perfect Customer Interview

The title is conceptual, and I try to avoid illustrating intangibles such as a conversation or a thought process, because they either require too much interpretation or they’re too vanilla. But the introduction included a story about a dress, and since the reference was made in the beginning of the piece, I knew readers would make the connection right away. (If I’m unsure whether an illustration makes sense or connects to the post, I ask for feedback from a randomly chosen teammate or friend.)

The biggest challenge, as it turned out, was illustrating the dress itself.

Illustration Sketch

Time boxing creativity

Though I never really have a bad experience illustrating, some post images are more challenging for me than others.

For example, “It’s Never a ‘Normal’ Month” should have been a quick win, because it was a simple, succinct topic and there were a lot of visual elements mentioned in the post for me to work with. It didn’t take long for me to develop a concept that felt like a homerun, but there was quicksand between the bases.

It’s Never a ‘Normal’ Month

I started with the premise of a calendar, then sketched some examples listed in the first paragraph of things that would go on a calendar, like theater tickets and other to-do list items one might schedule. I went to work transforming the concept into a detailed illustration, and the “Stephen” chant quickly faded as the story I envisioned didn’t translate in practice (and it took several hours to get there).

“U2 albums never get finished; they just get released.” — The Edge

This quote has stuck with me over the years, because I feel that way about a lot of my work; I often want to go back and tweak things. When I work on illustrations days or weeks before, it’s almost too much time, and I end up making perpetual tweaks until it goes live to make it just a little better. And while it can be fun to go down a creative rabbit hole to where the streets have no name, those small tweaks often don’t significantly improve the quality or impact of the illustration.

When you’re on deadline, you don’t have the luxury of being stuck.

That’s why I wait until publishing day to create the post image. It’s a self-imposed creative constraint: I don’t have the option to spend more than a couple of hours on it, which forces me to push through the challenges. So when it’s 10 a.m. and I haven’t sketched anything I’m amped about, I have to step back and ask: OK, do I start over completely on a brand new concept? How long is that going to take?

More often than not, the answer is to put my head down and keep working on it until I can get the illustration to a place I’m happy with. It’s often in those stressed out and sweaty moments that I experience creative breakthrough.

Breaking through the stuck

One post image I struggled with recently was How to Break Up With Abusive Customers. It’s just a broken heart necklace with two identical pieces, but it took me forever.

How to Break Up With Abusive Customers

I felt like this visual would be quickly related to the post concept, and the mental version looked pretty cool.

I just couldn’t get it to a place I was happy about. It was too simple of a concept; no matter what I tried, it always looked unfinished. Eventually, all that time I spent spinning wheels trying to polish it up wore out my creative energy.

Typically my least favorite illustrations are the ones I’ve spent the most time on.

That’s because I’m trying to find the “sauce” that will make it amazing, and I don’t. At that point, I rely on our design standards to get the illustration done. I may not always be happy with it, but I know it’s complete, because it fits with the post topic and lives up to our quality standards.


There are some illustrations that I don’t enjoy creating but I’m happy the end product, and others where I enjoy the process and I’m stoked about how they turned out. The illustration for How Smart Retailers Are Using Customer Service to Drive Loyalty is one I liked for the process and the outcome.

How Smart Retailers Are Using Customer Service to Drive Loyalty

Two concepts in this post stood out to me: always being available to the customer, and making the support experience effortless. The first thing that came to mind was a cell phone in your pocket (always available), and when you reach for it, a hand comes out offering you something you need (effortless). Then it was just about the extra cues like the life preserver and waves rippling on the phone (I also like how the curves and the perspective angle of this phone are even).

It’s different from my normal 2D style, and the technical process of creating in 3D was a fun challenge.

Sure, there are things I would change: The life preserver doesn’t fit through the hole in the screen, the waves could appear more like they are rippling, and I wish the arm shooting out was a little more fluid, but I still feel good about it.

Trying new things

I can’t always explain what motivates me to try something new, but I love when I land on something new that just works. Lately, I’ve been experimenting with opacity — how transparent an element of an image is — and it has been a fun way to push the boundaries of our style. One example is the transparency in The Future of Customer Support:

The Future of Customer Support

It was actually an update of another robot I did in 2016:

Old robot

Historically I’ve avoided opacity because playing with color saturation makes it difficult to maintain your brand style, but I like the results and the excitement of doing something new, so I’m continuing to experiment with it. (Text, on the other hand, is still a no-no for me, because I believe an illustration is stronger when it communicates an idea without leaning on copy.)

Overcoming creative slumps

If I’m not inspired by a post topic and I devote a lot of energy to it, I’m probably not going to love the result. It’s a vicious circle: Spending a lot of time on something I’m not inspired by causes me to produce something I don’t like, and the end result (naturally) is that I feel bummed about it. That can be tough to bounce back from, but it’s the job, and I have to find a way. The slippery slope of feeling like a failure when creative block strikes is usually avoided by reminding myself how amazing it is that I get to do what I love for work every day.

“Aren’t we lucky to be able to punch into design everyday?” — Aaron Draplin

Unicorns and rainbows aside, when I need to get unstuck it helps to go for a walk, make coffee, or read an article on Medium. But the most effective thing I’ve found is to clean. It’s a win-win: I accomplish something while getting myself back in a creative mood! In fact, I normally save busy work, administrative tasks, and so on for later in the afternoon, when inspiration is harder to come by.

Illustrating a brand

In terms of inspiration, I’m more drawn to branding and how illustration is used as part of larger system or visual language than I am to stand-alone illustrations.

What impresses me, and what I aspire to in my own career, are illustrators who can consistently adapt their style to create something unique to support the brand they’re working on. One example of this is Dropbox. They created a set of characters that they use throughout the product and marketing site, so the consistency and unique traits in the style play a vital role in strengthening the brand.

That’s the style goal with the Help Scout blog illustrations I create: Each illustration supports an individual blog post, but collectively, they make up a significant piece of our brand.

The future, by design

Illustrator Mikey Burton says that he needs to be completely overwhelmed to get creative work done. When describing a typical project for The New York Times, Burton says he gets the design brief around noon and has to deliver a finished product by 5 p.m. It’s a fast-paced, high stakes job, yet this is exactly what motivates him: “If I have ten things to do in a day, I’m going to keep working until they’re done. The lack of work makes me lazy.”

This is true for me too, but right now, I’ve got plenty to keep me busy at Help Scout, including a surprise project I’ve been working on that I can’t wait to share with you very soon …


See how values guide our brand

Stephen Murrill

Stephen Murrill

Stephen is an illustrator, visual designer and Help Scout alum. Connect with him on Twitter.