How to Use Creative Exercises to Build Happy, Healthy Teams

by Katy French

We feel so lucky to get to do creative work every day. Writing, designing, coding—whatever our hustle, it’s pretty great to get a paycheck for what we do. But even when we produce solid work and our partners are happy, we know we should never rest on our laurels. Experiment Often is one of our Five Columns values, but it’s not just a fun phrase. We see it as integral to our personal and professional evolution.

In creative work, it’s easy to get into a rut—even if you don’t think you’re in one. If you fall into the same patterns or produce the same stuff over and over, you only stagnate. Stagnation = creative death, so our creative departments are encouraged to mix it up every now and then to try a creative exercise totally out of the norm—just because.

Experimenting Through Creative Exercises

These types of creative exercises come in many forms. Sometimes it means the whole company closes up shop to host a Hack Day. Sometimes that Hack Day inspires a crew of C5ers to spend an entire weekend creating a video game from scratch. Sometimes that means we grab a conference room and let our creative freak flag fly.

Our design department is particularly big on these creative exercises, making it a point to do them once or twice a month. We wanted to share a few examples of their challenges in case it might inspire you to come up with some for your own team, no matter your particular skill or industry. 

Design Department Creative Exercises

Where do the ideas come from? The team has a ton of skills—calligraphy, papercraft, animation—and a ton of stuff they wish they could do better, but their work doesn’t always allow for that. The ideas for creative exercises are usually based on their creative passions, interests, or yearnings. These challenges are the perfect way to funnel that energy, encourage creative thinking, and let loose for a bit. Here are some of our favorite challenges.

City Flag Redesigns

After noticing the interesting albeit sometimes hideous design of city flags, we challenged our crew to give city flags a minimalist redesign. Naturally, we chose cities near our Orange County and New York offices. 

Column Five creative exercises

It was tons of fun, and it ended up giving us a little press too. We shared them on our blog, and even Wired picked them up.

Column Five creative exercises

Check out all of the designs here

Type Fight

The alphabet is a great source of inspiration for typographers and hand-letterers (of which we have a few in house). So we challenged our team to create their own interpretations of specific letters of the alphabet, based on a randomly chosen theme. The first challenge was to design the letter “L” with themes like XXX and Sugar, Spice & Everything Nice. (They got a little freaky.

Column Five creative exercises Column Five creative exercises

You can see all the designs to judge for yourself.


For this one, everyone had their own piece of paper and had 20 seconds to draw whatever the moderator said—in whatever style they said: “Draw a tree.” “Now draw a different tree in perspective.” “Now draw a tree with only fill and no strokes.”

It was a simple, silly way to flex our illustration skills.

Design for charity

When the Cancer Research UK was soliciting Comic Sans-themed posters for an exhibition, our team collaborated on a design for the organization.  

Creative Exercises Column Five

Sketch Telephone

We took it old-school with this one, turning the childhood game into a funny but tough design challenge, wherein 10 people sat around a table with blank pieces of paper in front of them. The first person came up with an image in their mind (based on a theme) and told the person next to them, who had to illustrate the image. The person to their right then had to write down what they thought the image was depicting, then pass it to the next person as their prompt to illustrate. Needless to say, what started out as “Santa eating cookies,” ended up as something we can’t say here, which is why we don’t have any pictures to share of this one. 😉 

3 Reasons Creative Exercises Keep Us Happy and Healthy

For us, these little mini-challenges or creative exercises are the best way to stay on our creative toes—and ultimately help our business.

1) They stretch our creative muscles 

The challenge might make us think in new ways, experiment with a medium we’ve never tried before, or totally surrender everything to some crazy idea. These all help us become better creatives, and they filter into our work. We might experiment with an animation style that we feel more confident pitching to a client down the road. We might get super inspired by a coworker’s ridiculous (but also genius) design. It all feeds itself.

2) They make us more productive

The whole point of this exercise is to get together to try new things and learn about how to be better creatives. In addition to our creative challenges, we meet once a month for a “tool time” meeting where we share our favorite tips, tricks, tools, and hacks for getting stuff done. It’s a time to figure out stuff we were too busy (or too shy) to ask, and it helps us do everything better. (We do this with the whole company too—our finance manager once shared a presentation on email hacks that was seriously enlightening.)

3) They create a stronger community

Some exercises require the team to work toward a specific goal together, which certainly brings us closer together. But the individual projects do that too. We might be trying something we’ve never done before, practicing a skill we’re not totally confident in, or making a total mess. The wins are awesome, but the bombs are what really bond us. Even when we fail, look dumb, or do something we straight-up suck at, we’re doing it together.

Now that doesn’t mean we’re always working as a group. Sometimes these are self-directed activities based on a prompt. We believe these are just as important because they cultivate trust and an environment of creative freedom, which are invaluable to our company culture. (We’ve all worked at places where this was not a value—and, surprise, none of us work at those places anymore.)

Even better, these exercises also allow our department directors to take off their “manager” hat and join in the mayhem—not judge from afar—which is a particular treat.

How to Make Creative Exercises Work for Your Team 

Throwing up a fun flyer and patiently waiting in a conference room for everyone to file in doesn’t mean your team will be on board. There are very specific elements you need (and you need to communicate) for these types of exercises to work.

Designate Free time

There’s always something you can be doing in your down time, but as soon as an email or edit comes through, you have to abandon ship to tend to it. We find the best, most relaxed environment comes when no one has to check email or be distracted by something else they shouldn’t be doing. That’s why we do these before work, after work, or during the lunchtime block.

Make it zero pressure

The point of these exercises is to stretch your skills. This can feel uncomfortable in a larger setting but not when everyone else is game to try it too. We make it clear that we are all welcome—if not encouraged—to fail.

Remember Fun, Fun, Fun

Yes, “fun” sounds a little cheesy, but one of the most important things we want is for everyone to let their guard down a little bit. Creating a fun activity that doesn’t feel boring or like a burden means everyone is more cooperative and enthusiastic. (They’re also more likely to give up their free time before or after work.) When we see people laughing and having fun, we know they’ve ditched their self-consciousness and self-doubt. That’s the ultimate goal.

No matter your industry, we believe you can always find some way to challenge yourself in small or big ways. We hope this encourages you to try something new today.

For more Column Fives projects:

If you need some help with your own design inspiration, we’d love to hook you up.

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