Getting comfortable with being uncomfortable

To take one step is courageous;
to stay on the path day after day,
choosing the unknown, and facing
yet another fear, that is nothing
short of grace. 

—Excerpt from Sangha, by Danna Faulds¹

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Believe it or not, about 15 years and 30 pounds ago, I used to run marathons. Yes, the 26.2 mile kind of marathons. The crucial part of training for marathons is the weekly long run. Each week over the course of a 4 month training period, you add one more mile to your long run than you ran the previous week. Near the end of your preparation for the race, you’ll probably have logged three runs of 20 miles or more. The rationale of this type of training—or madness, depending on your point of view—is getting your body used to being comfortable with feeling uncomfortable. After all, there’s really no way to avoid being uncomfortable at some point during an endurance race that covers 26 miles.

Two cases in point. During my first marathon in the Fox Valley, we were treated to 40 degree temperatures and a 20 mph tailwind for the first 18 miles of the course. At mile 18 we turned back into that cold wind, at which point my entire body immediately cramped up—with eight miles to go. Uncomfortable is not the word. Excruciating and soul-destroying come to mind. But I eventually finished the race and was given the customary finisher’s thermal foil sheet, medal, and long-sleeve t-shirt. Two years later at the 1996 Grandma’s marathon, I absolutely cruised for 25 miles, until I hit a complete power outage. But with only 8 minutes of exertion left, I knew I could easily gut out those last moments of discomfort to get my finisher’s medal.

Uncomfortable circa 1996

Now that I’m older, I run much shorter distances, but I’m still faced with many days when it just feels flat out uncomfortable. I have to actively remind myself in those instances that eventually this feeling will pass, and I’ll be better conditioned because of it.

So what does this have to do with what we usually write about on this blog? Okay, confession time. The last three years have been the most uncomfortable period of my professional career. Allow me explain.

In late 2008, I decided I had enough with advertising. I had done everything I wanted to do. Got in all the important award annuals, won multiple best of shows, and worked in Minneapolis for an agency I had always admired. But I didn’t love what I did anymore. In fact, it had become boring and tedious. Campaign after campaign after campaign. Telling clients we actually affected their business, but what we really did was just delivered was marketing materials. Great ads with great thinking, but in the end they were ads.

There were still things I liked about my profession. I loved design, more so than ever. I had discovered a design blog called Grain Edit, and I started tinkering with the simple “mod-style” of illustration that Charley Harper and Saul Bass pioneered, and that shops like Invisible Creature carry on today. I loved thinking and strategy—I just didn’t want that freedom of thought to be limited to ads. I had gotten my first taste of digital, and loved all the moving parts, and the need for collaboration that was talked about often but rarely put in practice at traditional shops. I had an idea for a creative school for special needs kids. I had ideas for businesses. And I really liked this thing called social media. But what was I going to do with all that?

With no finish line in sight, I pushed myself to be uncomfortable. I admitted what I didn’t know. I was willing to learn, in exchange for sharing the valuable things I did know. And I was willing to give up a position of respect in an industry that I had worked in for over twenty years, in exchange for something unknown, for psychologically starting over. There are lyrics from an old Yes song that say “don’t surround yourself with yourself,” and that’s basically what I did. All I had was experience, guile and my work ethic.

I was really good at making stuff like this. And then I walked away. (sorta)

Nothing would come easy. I moved back to Milwaukee from the Twin Cities (something I swore I would never do—heh) to work for Fullhouse, which at the time was a fast growing digital shop. It appeared to be a good match. They were interested in my experience developing creative and working on brand strategy. I was interested in taking that and applying it to digital, and learning as much as I could about digital, social, and technology.

I tell this story often. Having been spoiled by some of the strategic and creative minds I had worked with while in Minneapolis, I doubted I would find that back in Milwaukee. Call it snobbery, but when you work with some of the best, your expectations are forever changed. On my first day at Fullhouse, I was put in the third floor conference room with @deziner. I remember 15 minutes into that meeting I caught myself wondering about her: “What on earth are you doing here?” She belonged in New York or Minneapolis or London. I knew in a 30 minute meeting that Cindi Thomas was someone I wanted to work with and learn from for a very long time. I got the chance to work with a lot of other really smart people there as well. Perhaps some of you have heard of guy named @augieray who went onto Forrestor, and is now VP of Social Media at USAA. There was also @cullenob, still one of the most driven professionals I have ever met, and the wicked smart digital strategist @gkalantzis. I’m not sure what was more amazing about James Newell—his front-end development skills, or his ability to remain so centered with all the talent and intellect he possessed. I often commented it was a little bit like working at NASA in the late 60s. There was a similar attitude of just figuring out how to do things.

If you haven’t heard, things did not work out at Fullhouse. Ironically, ownership could not get comfortable with being uncomfortable at a time when the industry landscape was changing for everyone. Twelve months after I started, Cindi and I along with Andy Wright, left to start Translator. Within the span of just over a year, I was not only back in Milwaukee, but I was back to being involved in a startup agency. Add to that I felt a bit like an insect in mid-metamorphosis. I was completely out of traditional, but still not embraced by digital.

Translator got off to an unexpected slow start—a large local client that promised to bankroll our first year if we left Fullhouse, backed out after we quit. This was financially devastating to the three of us, to say the least. (See mile 18 of Fox Valley marathon above). The immediate setback challenged why we had started the agency in the first place. Was it the promise of money, or our belief system?  In a variety of rather surprising situations, my abilities were second guessed. This led to a stunning loss of self-confidence, something I hadn’t experienced in over 15 years. After only five months, we went through a partnership change at the agency. This contributed to us losing control over the product idea Translator had created—Meet-Meme.

When work finally did start to come in, it wasn’t a trickle, it was a flood. The zero to 120 mph pace led to more issues. I was left thinking, maybe I made a mistake. Maybe I’m too old for all of this. Maybe I can’t change.

It was all extremely uncomfortable.

But at the same time, progress was also being made. Through our former Fullhouse colleague (and all-around good guy) Micah Eberman, Cindi and I got a chance to work on a huge project for R/GA, an agency we both greatly admire. The work we did was extremely well-received, and it provided validation for the type of thinking the two of us had been collaborating on since we first met at Fullhouse. That style of thinking—what I would describe as a mash-up of the Diageo brand essence wheel, user-based behavioral research, and creative storytelling—is really the key to our current success. It results in complete stakeholder buy-in at the highest levels, and is what continues to attract new clients to Translator.

polish moon

Mod-style illustration and packaging hits the shelves soon.

We started to have success. My confidence came back. Not only in myself, but in delivering on the vision that Cindi and I had for what it meant to be a modern “agency.” We executed in what we believed in, even if that was outside the defined norms of what it is to be an agency. The compliments we receive from our clients are not ordinary. “You took what was in our heads and finally made it clear and actionable.”

Earlier this year, we were fortunate to be recommended to Brendon Thomas, who had an idea for a crowd-powered music booking platform. Shindig is about to launch in beta, and today we are closing on first round funding (w00t!). The hard lessons we learned on the first product partnership didn’t stop us from trying again. This time around the partnership was built upon mutual respect, and the experience has been vastly—and pleasantly—different.

We’re funded. Dig it.

My old ad colleagues ask me what Translator does, and when I explain it to them (without getting into deliverables), they say “I still don’t get what you do.” And that’s okay. We’re not defined by our work. We’re defined by how we think. Our clients—who are often C-level or company founders, are drawn to that and like it that way. Our approach to idea architecture and experience design is focused on transforming their entire business—not just their marketing.

In addition to morning lab sessions, we started the Translator XSMKE series. Rather than start or join yet another local committee to try promote creativity, we just decided to do our own thing. So far we’ve put on 5 events this year, including a live performance for the launch of Nineteen Thirteen’s first EP, a screening of the documentary Miss Representation, and a live staging of The 3six5 with @LenKendall. We’re interested in promoting and cross-pollinating all forms of creativity, in art, music and technology. It has nothing to do with being a typical agency—and everything to do with being us.

It’s often said about marathoners and professional endurance athletes that there’s no talent gap between winners and losers; rather, it’s the mental trait of not accepting your limits that decides who wins. Whether it’s growth, progress, innovation, change, none of it comes without a price. It’s human nature to stay away from things we don’t think we can pull off. Failure is embarrassing. And so we stick to doing what we know how to do. It’s safer that way.

Not that long ago, I seriously thought my best days were behind me. This weekend, I will turn 50 years old and I am here to say I survived being uncomfortable. I got through it, and I love what I do again. I’m better now than I was at 40, plus I can do a lot more things I never thought I could do. And what’s best, is that I especially love the people I work with everyday at a single long table we all gather around at Translator—Cindi Thomas, Kirsten Corbell, and Ben Leisch.

Yes, some days are still uncomfortable. That’s part of growth. As with running, I try to remind myself to breathe, ask myself why it’s uncomfortable, and remember that I am on the path day after day for a reason. When I stick to this the sky is the limit, and there’s never any finish line.

I’d love to hear if you have a similar story, or maybe if you’re going through the trials that come with being uncomfortable.

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¹Special thanks to my Kripalu Yoga instructor Heather Burkart for reading this during class on the night of November 2, 2011. Roughly translated, Sangha means a community with common goal, vision or purpose.

As @deziner has taught me, there are no coincidences. None.