How Wendy Lee Oldfield Stays Creative

Graphic designer/creative problem solver Wendy Lee Oldfield knows how to stay creative when the less creative parts of life get you down. Considering that she coauthored Caffeine for the Creative Mind and Caffeine for the Creative Team, and that she recently participated in a creative activities experiment based on Jim Krause’s D30: Exercises for Designers, it should come as no surprise that Oldfield makes a point to see the world in a creative way no matter what she’s doing.

Her latest experiment in creativity combines Instagram and circles (yep, as in, the shape). For over a year, Oldfield has been photographing circles she’s come across and sharing them with her followers. I had the opportunity to talk with Oldfield to learn more about this unique project, and how it’s helped her to continue living a creatively curious life.

Wendy Lee Oldfield - how to stay creative

For years my grandma has photographed all things heart-shaped, and I always found it interesting that she chose hearts. So, why circles? Why not squares, or triangles?

That’s a good question! This project was actually inspired by an interview that The Great Discontent did with Matthew Smith last year. While he didn’t discuss his Instagram account in the interview, I tend to check out people’s social media accounts if I find them interesting. When I took a look at his Instagram account I was blown away by his collection and study of peaks. I was inspired by his curiosity and wanted to do something along the same lines.

Wendy Lee Oldfield - how to stay creative

The circle was the first shape that came to my mind. A circle seemed like a simple, straightforward shape to document as a beginning exploration—I didn’t want to start off with anything too complex. I emailed Matt and asked him if it would be OK if I studied them like he’d done with his peaks series, and he was very encouraging and enthusiastic about it.

Wendy Lee Oldfield - how to stay creative

Will you ever start a second project with a different shape?

Most definitely! My goal is to reach 200 circles, after which I will be creating a poster filled with all of them that I can hang in my office as a visual reminder of leading a creatively curious life. I will then move on to something different to study, but I’m not sure what it’ll be yet. Definitely something a little more complex than a circle though, I can tell you that.

Wendy Lee Oldfield - how to stay creative

You chose to document this project on Instagram—rather than a folder on your laptop that no one else will see—so that others can follow it. What do you hope others will gain from your project?

Well, to be honest, I was curious about quite a few things when I started documenting this project. I am fascinated by social media and how people interact with each other. Some Instagram accounts are all about selfies. Some are all about a parent’s kid. You also get some super creative accounts, and I’m always intrigued by what people find interesting and what they follow.

Before I started posting my circles, all of my followers were friends and acquaintances. I would usually just post whatever caught my eye, but there was nothing very thematic about it. I had a feeling that once I started working on my circles I would lose a few followers, and not get as many “likes” as my previous, more personal posts. There’s a certain amount of ego attached to putting your work out there. You could post one of the coolest, creative pictures of all time, but in a world riddled by selfies and boobs and popularity, valuable artistic gems can easily be overlooked.

Wendy Lee Oldfield - how to stay creative

Wendy Lee Oldfield - how to stay creative

It was sometimes hard posting a circle that I was very proud of but got no “likes.” But a large part of me didn’t care. I wanted to do something different from the world of selfies. Life is so interesting, and I wanted to explore it.

In short: I wanted my content and what I posted to have value and meaning. I don’t think a lot of my followers understood what I was doing at first, but it opened up a great dialogue and discussion when they asked me about it in person. I was also curious to see what kind of new followers I might gain with a more “arty” project. At the end of the day though, I told myself to not base what I posted off of what other people’s reactions might be. If they didn’t like it, then they didn’t need to follow me. This was a project for me. It was something that I could do to keep myself inspired.

Wendy Lee Oldfield - how to stay creative Wendy Lee Oldfield - how to stay creative

Ryan Booth said this last year and it has really stuck with me throughout this project:

It’s easy to feel like nobody noticing your work is a sign that you should stop, but it’s not. It just takes a certain amount of time for you to acquire the skills to make something with real weight and significance.

circle65 Wendy Lee Oldfield - how to stay creative

A few years ago I coauthored two books on creativity and creative exercises, and in a way, this project has been an in-depth creative exercise for myself. My hope is that this project will inspire others to see the world in a creative way through curiosity and exploration.

Wendy Lee Oldfield - how to stay creative

Circle #1 looks like a mug of tea from back in April 2013, and your most recent circle, Circle #164, posted on Tuesday, June 24, looks to be a logo for a coffee at Starbucks that comes from the Sable Farms in Malawi, East Africa. 164 circles… Have you noticed any themes arising among them, or have you discovered anything about yourself based on what you tend to photograph?

One of the things I noticed quite early on is that there are a lot of common man-made circles out there. I didn’t want my project to be a collection of different types of sewer lids or views of drinks in cups from above. I wanted each circle to be as unique as possible. After all, the goal was to document as many different circles out there as I could; not just the same idea recycled. So I guess the only “theme” that I wanted was that each image had to have a unique circle in it. I didn’t want them to be any more thematic than that.

Wendy Lee Oldfield - how to stay creative

I’ve noticed that I’ve become more meticulous and perfectionistic with the pictures that I take and any editing/filtering I do. I’m sure a lot of this has to do with the idea of making all of these into a poster, but I think it also has to do with valuing something and taking the time to do it right. There have been quite a few times where I had to hurriedly take a picture, only to discover later that it wasn’t quite in focus, or I didn’t capture the full circle, only a piece of it.

Wendy Lee Oldfield - how to stay creative

As tempting as it is to just post what I have, I will omit a circle if I feel like the quality isn’t good enough. If the snapshot that I took during rush hour on a busy walkway was too blurry, then maybe it wasn’t meant to be. But I tend to try to make sure that every picture I post is a good-quality image that I’d be proud to look at.

The other thing that this project has helped me with is to pay more attention to my surroundings. I’m almost always looking around for the next circle to document, and it has helped me to observe some of the smaller details in everyday life that may have otherwise been missed.

Wendy Lee Oldfield - how to stay creative

All of your photographs are wonderful. One of my favorites is Circle #136, which I find just breathtaking. Can you tell me a bit more about where that one was taken?

Of course! This was taken on a trip that I took to Banff, Canada. My husband and I love to explore and discover new things, so one day we decided to explore an awesome castle-looking hotel called The Fairmont. There was a gorgeous lounge that we wandered into, and this window instantly caught my eye. It’s not very often that you see a circular window, and with the beautiful Banff mountain view in the background, I just had to add it to my collection.

Any favorites among your circles thus far?

That’s such a hard question to answer! It’s like asking a designer what their favorite color is. I don’t think I could give you a #1, but my favorites so far are: 35, 62, 80, 88, and 124.

I noticed you don’t add descriptions to your photographs, beyond labeling the circle number. Is there a reason for this?

Most definitely. I took the picture. I know what it is, or where it’s from. I don’t want to spoon-feed people that are looking at them. I like to leave the interpretation up to them. Some of them are very straightforward and obvious. But I especially like the ones that make you think, the ones that make you tilt your head sideways, or stare at it for a while and imagine what it might be. There are also a few where if you stare at them long enough, you might notice that there are circles within circles!

Wendy Lee Oldfield - how to stay creative

Finding all these circles (164 and counting!) and sharing these quality photographs is no small featdo you think it could lead to something in the future, or somehow grow into something even greater?

I started this project with one mission: collect circles to keep myself creatively inspired. I told myself that if something further came of it, then awesome. But I wasn’t counting on or hoping that it would necessarily lead to anything else. Sometimes you need to just make things for the sake of making them. You get to be your own boss where you get to make the decisions about what you’re working on and how it should look.

circle127 Wendy Lee Oldfield - how to stay creative

As time has passed and strangers have stumbled upon my circle project, little things have most certainly popped up in response to it. For one, I’m being interviewed for this blog post. I was also asked to be a part of the creative team for the Circles Conference when the founder, Ismael Burciaga, discovered my circles a few months ago. But perhaps the thing that I’m most excited about is creating my circle poster that I can hang on my wall and look at every day.



You state on your website that although most consider you a “graphic designer,” you really like to think of yourself as more of a creative problem solver. You also state that this circle project has helped you to “look at things in a different way,” and that it’s ultimately helped you with your design work.

Can you share with us a specific example of how the circle project helped you to solve a creative problem by looking at things differently?

I sure can! The first is quite an obvious connection. I had to send off a package to Ismael for the Circles Conference. Most people would put together a package, fill out an address label, and then send it off. But I thought to myself, why not make it more awesome!? I’ve started to explore the world of hand lettering, and I thought this package would be a great opportunity to mess around with some hand lettering and a circle.

Wendy Lee Oldfield - how to stay creative

Wendy Lee Oldfield - how to stay creative

The package was for the Circles Conference, so why not make the address label circular? Of course, this idea came to me when I was buried with a plethora of other projects with tight deadlines. But to me, this seemed like a great combination of creativity and relaxation, and something that I could do while my brain was also thinking about the other projects on my plate. I spent a good three-plus hours on it, but I had one of the most enjoyable evenings in a while, and I went to bed that evening feeling creatively satisfied.

The second isn’t necessarily with circles, but the circle project has helped me hone down on this skill: only post quality. Take the time to make things as good as they can be. Edit. Delete. Question. These actions have transitioned in to how I deal with client communication, blog articles I write, and even social media posts that I publish. Take the time to do things right. Don’t publish something half-arsed.