Creativity is inherently risky, or so people think. But when you reach a certain level of skill in a creative profession, you learn that’s not always true.

As a designer for 15+ years, I can produce lovely designs that I really don’t give a damn about. I can go with a design approach I know will get quick approval or that won’t rock the boat for the intended audience.

Or, I can choose to invest myself into my work and chase a greater sense of accomplishment. For some projects, I do push myself to do something daring, different, and a little risky.

When I go the creative route and take a risk, sometimes it backfires. Sometimes people email me and say “that design made my eyes water” (yes, that really happened, and I don’t fault the person who said it). And because of that I might hesitate a little more next time.

But there’s really no relief either way. When I go the safe route, there’s still this nagging doubt in the back of my mind that I could have done more—that I wasted a chance to do something amazing.

I oscillate between these approaches and chastise myself no matter which I take.

If I play it safe, I call myself a sellout who is too scared to take a stand for my perspective.

If I go creative, I call myself overly self-indulgent and impractical. A fool for taking a risk when I could have had a sure thing.

So this week I sat down to decide once and for all: which is the best approach, creative or safe?

I wrote a pro-con list. I categorized past designs by whether they were creative or safe and wrote down how successful they were. And I found something that’s going to disappoint you:

Out of dozens of projects, the safe approaches almost always did better, with only 1 or 2 exceptions.

Disappointing, right? Don’t worry, I’m not going to tell you to start playing it safe all the time.

When I looked back over that list of projects, I realized that the safe approaches were about other people while the more creative approaches were more often about me. Safe approaches worked well because I was thinking about how other people would react instead of what I wanted to do.

The few exceptions—the creative projects with good outcomes—really didn’t outperform the safe designs either.

I hate that realization so much. I want to do work that’s fulfilling for me, and the evidence seems to be saying I shouldn’t. I am so tired of people telling me about user research, UX, and job stories. Sometimes I just want to sit down and create something I love.

But when I look back on those creative projects, they weren’t as satisfying as I thought they’d be. If anything, what I remember most is how many of them failed and how the temporary feeling of shipping something I liked was quickly eclipsed by the poor reception.

We’re creative professionals, and for some of us the whole reason we got into this was to do fulfilling work we love. The idea we can’t do that—that we have to play it safe—is disheartening.

But when I use design work as a creative outlet, it often comes back to bite me. This is a lesson I keep having to relearn. Design is usually more effective when it’s based on research and data rather than my personal preferences and vision.

More and more I feel that this intellectual approach to design is winning out over the more emotional, creative approach that got me into this profession in the first place, and it’s sad.

Sometimes I think “Well, I’ll just save that creative energy for another outlet or pursuit”, but that’s even more sad. Design was supposed to be that outlet. But design isn’t always the job I thought it would be.

I’m not writing this article to tell you to play it safe, stifle your creative energy, and avoid risk. On the contrary—I want to tell you the exact opposite! I want to tell you to get out there and make daring, amazing things.

But I want you to succeed, and I know that design isn’t art, as much as we sometimes want it to be.

I also know that if we designers all played it safe, we’d all collectively be missing out on great things. Those few exceptional, special designs—you know the ones—came from that daring spirit to do it anyway and the refusal to let failure bring creativity to a halt.

So what do we do with this conundrum? I don’t have a good answer. I think we keep wrestling. We keep testing out those daring ideas when we can, and play it safe when the stakes are high. We keep looking for balance, if there is such a thing.

We choose to acknowledge both approaches for their merits, and maybe finally stop calling ourselves failures on every design because it’s either not creative enough or not safe enough. Maybe we can just use the approach we deem best, and let that be enough.

I for one am not willing to give up on my creative concepts for good. They don’t all work out, but I still want to try to find the few that do.

But I certainly don’t mind an easy win, now and again, and there’s nothing wrong with that at all.


Check out my latest risky design, Mod&Dot. It’s a browser DevTools extension for capturing design edits then sharing them with your team. If you sign up for the waiting list, I’ll know the risk I took on this design was worth it.


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