Mission Uncomfortable: Embracing the Breakups & Breakthroughs of Creativity
Michelle Mattar / WNW Member
I was about to start a business. In November 2016, I was laying the groundwork to start my own studio… and then Trump got elected. The world felt different: not dramatically and overnight, but like it had always been different and I just hadn’t fully accepted it yet. My best laid plans no longer felt best; I was trying to start a relationship on a bad note. It was a moment when I needed real gusto, determination — and maybe even some dreamy optimism. But that feeling just didn’t exist anymore: going in apprehensive and half-heartedly wasn’t an option, or at least, it wasn’t a good option. So I broke up with the idea.
I wasn’t sure how to come to terms with the best thing no longer feeling like the best. At that point of my life, I was considered young to be freelancing in the way that I was: creating holistic visions for brands to launch with and build their futures around. I had just launched a project called Ritual a month prior, and the response was overwhelmingly positive. Finally, my age was not a point of skepticism. Potential new clients had trust right off the bat and let the work take the spotlight. After all I had been through on that front, an excited “Finally!” should have entered my mind, but it didn’t. The high point never came.
This wasn’t a low point, either. There was no depression or feeling unsuccessful; instead, I was at a personal high point but unable to lean into that moment and take advantage. My indifference took the wheel and I realized quickly that I was in a rut. Which is hard to survive when you’re self-employed– just sliding by would mean a quick spiral into mismanaged projects and a massive headache. I had to think quickly, so I drew on how I’d get unstuck creatively. It’s cheesy and obvious, but something I stick to: “Look outside of the category for inspiration.”
“I was at a personal high point but unable to lean into that moment and take advantage. My indifference took the wheel and I realized quickly that I was in a rut. Which is hard to survive when you’re self-employed.”
I thought I was bound to get a different perspective on what to do if I took a path that led me to an entirely new vantage point. My own category was independent – I had very personal relationships with clients and built work that was collaborative at times, but largely created in quiet isolation in my Brooklyn apartment.
An opportunity knocked at my door that was not independent. It was a job as an in-house Creative Director at a fledgling startup in Los Angeles. I had actually said no to this very offer just a month before. Now, I knew it would be uncomfortable and discomfort became my new mission. I was willing to turn everything upside-down in order to get my motivation back.
Illustrations by Michelle Mattar
This was the environment I thought I’d never belong in. Before Mission Uncomfortable was even an idea, I’d left Agency World. It might sound regular to some, but to me, being full-time with just one project had always felt completely alien. I launched myself into this foreign territory very quickly, not allowing myself time to debate the pros and cons.
My choice to take the job and move to L.A. confronted me with two big teachers: one was the job itself and the other was the entirely new (friendless) surroundings. In the job itself, I was coming from a place where I’d always been carving out big visions and territories. Very rarely was I nuanced in day-to-day work.
In being on the ground every day inside of a company, I gained a better appreciation of the smaller steps towards a greater whole. That's something I wasn't empathetic to before I went and worked in-house. I would build a concept in a way that I thought was appropriate, give it what I thought was a reasonable expectation on timeline– but it was all from the outside looking in. The reality? The way an idea actually operates to become realized internally made my work feel painfully ignorant to the teams I served. I wasn’t building work with the right toolkits, or the right strategic foundation to fully empower the company to fearlessly dive into the deep end of a concept or brand vision.
“In being on the ground every day inside of a company, I gained a better appreciation of the smaller steps towards a greater whole. That’s something I wasn’t empathetic to before I went and worked in-house.”
That was my first learning in Mission Uncomfortable, and it stung a little when I looked back at old work. I realized that in my previous place as a creative, I’d never truly, fully valued the position that I was in: I’d get to present a larger-than-life concept. Then, a group of 10 people (in some cases 30, in some cases 80) would all work together for a month or more on something that I had put in front of them. I never appreciated what that meant, how lucky that was. In fact, I would be sitting on the other side of it wondering, "Why was that implemented so poorly?”
My next lesson was being in a totally new city and expecting to feel inspiration come back from that. I imagined an awesome adventure. Myself, a free spirit, easily navigating past hoards of Gjusta crowds towards new, uncharted territories. The reality: it was kind of boring. It was slow. My life was not unlocking itself and I needed to learn how to unlock it. Especially in my situation, where I barely knew anyone.
Illustrations by Michelle Mattar
I thought to myself, "Okay, I'm here. I can’t leave this soon. I'm not that miserable, but I need to start making excitement myself. It’s not finding me.” So, I didn’t sign a lease for months. Instead, I would try out different neighborhoods for a week each in a new Airbnb and make it my goal to rack up as many Google Map stars for places I’ve been in the area. I lived out of a duffel bag and relied heavily on a portable battery charger. I would ask New York friends to set up blind friend dates or I’d cold email people at Los Angeles companies that I liked, take them out for coffee, and ask them where they were hiring from. That was another difficult development in Mission Uncomfortable: I had to learn how to hire with my network starting over from scratch. I had somehow found the end of the Los Angeles rainbow of internet searches for creatives. So, I boldly asked people I didn’t even know: “Where are they hiding?”
I am a Myers-Briggs confirmed introvert, so this was wildly out of character. My uncomfortable decisions brought more challenges that prevented me from staying within the comfortable edges of myself.
It made me realize: When you're comfortable and have been somewhere for a while, you stop truly exploring. You stop reaching out to people, making new friends, trying new things. Maybe you try something new on a personal level, but I don't think you test your surroundings as much you could. I didn’t realize it at first, but I was developing a new skill: making my environment work harder for me.
More than anything, getting uncomfortable helped me interrogate what was irking me about my position in the world. Why did I feel stuck? As a designer, you're constantly trying to raise the question of, "Where in that line between art and commerce do I want to sit?" That was something I was pretty insecure about. Even before the election, I was always tossing myself back and forth. "Am I doing something good for the world?”
It was in making my environment work harder for me that I woke up to a realization that gave me back my inspiration. I thought to myself, painfully obviously, of just how strongly commerce is tied to the world we live in. So all I had to do was figure out how to make that environment work for what I wanted, which was to put something positive in the world. For me, that meant that an attainable (and even inspiring) way to create something real and meaningful would be through business.
This was a turning point for me. It made me feel better about the fact that I do want to work closely with businesses – but it also made me realize that I needed to get even more involved on the what. So I gave myself the title of Strategist, and decided that from that point on I would implore my clients to not just use strategy as a tool for identity, but to commit to answer the tough questions with me and resolve to do things with great intent. If they weren’t up for it, I wouldn’t be up for the work.
Eventually, I left LA and the job because, oddly enough, I got too comfortable. The questions I was solving for weren’t pushing me as hard as building brands would, especially equipped with this new insight. Nothing about building a brand is ever truly comfortable, at least for me.
“I wasn’t following up on my own work – which is awkward to say, but I don’t think the majority of people in this industry do. My old style was to hand it off and hope for the best, largely because the deliverables were designed for that. Lately, I don’t hand off and hope.”
Before my Mission Uncomfortable, I stayed within the edges of my deliverables. Since, I’ve began reworking my whole process as I merge “how ideas actually happen” and “why.” Now, I’m working towards delivering something that’s mindful to multiple teams and much more multi-faceted, which has required me to grow my skills accordingly. Style guides are one helpful tool for particular groups within an organization, but I now see an opportunity to roadmap a future brand that involves so much more. Work like this isn't about the harvest; it's about sowing the seeds to thrive day-by-day, piece-by-piece, and person-by-person.
There are some new challenges, like the understanding that this kind of work requires a very long-lasting relationship, even through inevitable bumps in the roadmap. Which has showed me that I wasn't following up on my own work– which is awkward to say, but I don't think the majority of people in this industry do. My old style was to hand it off and hope for the best, largely because the deliverables were designed for that.
Lately, I don’t hand off and hope. It isn’t optimism that keeps me going; it is a different feeling than one based in hope or happy musings about a better future—it’s about what I can do right now, what I can learn right now, and what it will mean tomorrow, immediately. Mission Uncomfortable landed me right back where I started, but with much less “hoping for the best.” This time, I’m finding inspiration in seeking out what’s needed to make my work more meaningful and more successful, and I'm not uncomfortable asking for it. I’ve gotten cozy with the idea of never stopping myself before I reach the next level, whatever it brings. I broke up with one idea. Breaking up is hard to do, but I think breaking through was worth it.