A young designer asked me this question during the Q&A session after one of my talks at a conference: "What is the most important skill to have as a designer?" After pausing for a beat, it dawned on me that the most important skill to cultivate as a designer isn't sketching, modeling, research methodologies, leading workshops, or presenting—it's dissatisfaction. Getting into the state of having just the right amount of dissatisfaction is the glue that holds all of my work together. It is something that was taught to me from the very beginning in school, and it is something I hold onto today.
At RISD we practiced what they like to call a "critique culture" where students were encouraged to look critically at the world around them and discuss those criticisms. This practice is meant to help you do two things: first, to look for opportunities all around you that you can work to improve and second, to turn your critical gaze onto your own work to try to improve it. If you didn't follow through on the second, a fellow student would be sure to bring it up in a critique of your work in front of the professor. Everything was subject to be questioned, from major design concepts to an instructor asking why your print was hung 5 degrees off level, or why a corner was dog eared, or why all of your tacks were not the same color. What we learned was that the only wrong answer was not to have one. To have not thought critically about your own work and how you presented it was a major faux pas.
If you are happy with something the way it is, you may not find the motivation to search for a better solution.
Later in my academic studies, I took an exchange semester at the Cleveland Institute of Art. The program there offered a bit of a different spin on RISD's critique culture. Their students were encouraged to walk around to see what their classmates were working on and to ask if they could do an "overlay" where they took a clean sheet of paper and quickly ideated their feedback and thoughts on your project. This practice built a strong sense of camaraderie and taught us that getting to the best idea was the most important thing—not our egos. By pushing our egos to the side, we opened ourselves up to the ideas of our classmates.
Whatever your creative output is, you have to have a measure of dissatisfaction to work on a problem. If you are happy with something the way it is, you may not find the motivation to search for a better solution. Sometimes creative people get a bad reputation for having a bit of an attitude, but this might be because we are constantly identifying everything that is wrong with the world around us.
If you have too much dissatisfaction, however, you may find yourself in a state of paralysis. Having overloaded on dissatisfaction, I know it can lead to a bad place where nothing feels good enough to show anyone. It has taken a long time to learn how to control that emotion and find the right amount of dissatisfaction.
When I am in that perfect state of dissatisfaction, I feel like the ideas and iterations flow more freely. I'm able to look at research more objectively and create patterns out of insights. I'm able to review work in a constructive way, and I'm able to receive feedback with the assumption that the person I'm talking to can help me make the solution better. I remember when I was working on the Air Jordan XXI PE I, was showing an early prototype to Gentry Humphrey, who was the head of product line management for footwear at the time. I was working on a complex lacing system that hid most of the laces under a second tongue for a very sleek look that differentiated the product from the production AJXXI. There can be a bit of tension between product line management and designers, and Gentry very carefully suggested that perhaps there was a little too much white space in the composition and that a molded lace keeper at the top of the tongue would add that extra bit of polish. He was surprised by how much I lit up with my response as I said, "that is exactly what it needs".
If you have a critical mindset to your own work, you find that good ideas can come from anywhere. When you ask other people to look at your work, they will give ideas to you. You have to apply that same critical thinking to the feedback you have gotten. You have the hard task of deciding what bits to leave behind and what nuggets can be turned into insights.
In my professional career, I've tried to hone that critical gaze into a healthy level of dissatisfaction. When people ask me what project I love the most that I have worked on in the last 20+ years, I tell them the real question is what project I dislike the least. I've learned something with every project—I see the mistakes, the learnings, the battles lost, and I love that. To me it means I have grown and that I could do even better now.
If you can take a critical gaze at your surroundings as you walk through the world, you will never be at a loss for work. There are so many solutions that we take for granted because they have persisted for so long. They are waiting for a dissatisfied designer like you to come along and make them better.