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Field Study

An Unedited view of design and thought process:

work, experimental and otherwise by Keenan Cummings

Interview: Proxart Magazine

This interview was done back in November ‘11 for Proxart Magazine. A few details have been updated. 

Much buzz has surrounded Wander, a site which currently boasts a mysterious edge to what the full-site/network will actually be. Some have predicted that it is an inspiration or curation network where one represents themselves through places rather than material goods. Others signed up because they saw their favorite designers do the same. Only time will tell, however, what the site will be when it actually launches. For now, all we can do is imagine.

The creative director and co-founder of the operation is Keenan Cummings, an NYC-based product/UX/UI designer, illustrator, and aspiring front-end developer1.

Initially stumbling upon his then-anonymous blog entitled Log/Transition, he mapped out his thoughts about leaving his traditional design agency job for the exciting and fresh startup world. With pieces of writing that enthralled many with his outlook of present-day digital culture, he continues to write on his blog and actively teaches classes on Skillshare.

Upon revealing his identity, he simultaneously revealed a tip of the iceberg which is his project Wander. Cummings was merely an eager and interested student of the start-up world, and now is an active participant within the culture — there’s no doubt that he is quickly rising in the ranks of the prominent New York City design scene.

Where’d you go for school and what’d you major in?

I went to school at Brigham Young University and majored in design. I had started a fly-by-night screen printing operation in high school. We were burning screens in my closet and screening shirts in our open-air studio (my parents driveway). I went to Korea for a couple years after high school and came back with an open mind as to what I would study in collage. Somewhere along the way I discovered that all these side projects I had been distracting myself with in high school — piecing friends names in an amateurish “wildstyle” (which is some of the most amazing typography out there‚ just Google image search it); giving friends henna tattoos to make some extra cash; creating ghost brands and covering notebooks and lockers in stickers; designing my next shirt to silkscreen — it was all design. That piqued my interest enough to look into Brigham Young University’s design program.

Turns out that this conservative small town university that sits up against the Wasatch mountains in home to a pretty incredible little program. I hustled for the next 18 months to first get myself into BYU. High admissions standards and an unimpressive high school record (all that “design” hurt my grades) meant I had a lot of work to do to prove myself. And since I had taken no art classes in high school, I had to build a portfolio from scratch. The design program at BYU takes 10-12 students a year so competition was stiff. But it all worked out and that education has been foundational to a satisfying career. They push a few basics: concept, typography, and general business and design intelligence‚ and those basics translate very well into real world work.

While working at an agency, were you merely a print/branding designer? Or did you already know code? If you didn’t, what was the last straw that urged you to learn? 

My agency and in-house experience has always leaned a little more on the strategy and concept side, but the end product was primarily print / collateral / merchandise / environmental-graphics based, mostly non-dynamic, limited interactivity type stuff. I had myself convinced that everything I was doing was “high level thinking” that could translate to any medium. When I started doing more dynamic/interactive work I found that that wasn’t the case. In fact, I found that other people had made similar assumptions, but continued to believe that notion and would go on to produce inept interactive work.

My initial attraction to designing for the web was not from client-driven interactive projects, many of which seemed to be high-gloss but low impact. It was from watching some incredible designers, many of whom had pretty traditional agency backgrounds, go on to produce deceivingly simple products that were changing behavior and building communities. It was only then that I found my inability to code a huge obstacle to doing this kind of high-impact work. After messing with code for the past few months I had this thought that I put up on my blog.

“Creatives have an inherent affection for every process involved in realizing their creative vision. No one that likes to design for the web hates code; they hate the pain associated with not knowing how to code.”

I realized that I was getting to a point where I could enjoy crafting code just as much as I enjoyed designing interactions or refining a brand mark. I associated code with so much pain but really it was the pain of having a vision and knowing I couldn’t execute on it. That’s the worst kind of pain for any creative person.

You said you wanted your work to mean something. Was it everything you thought it’d be so far?

In the first weeks of working on Wander, I was blown away by the work flow. We had a product vision but little else, so we were starting from the foundation (naming, concept, product), and adding floors every week (branding, user flows, UX, UI). We were doing nothing but the work. Every minute was spent designing and building. There was no time tracking, no orientations, company emails, training meeting, performance reviews; everything was work. Larger organizations might fall to pieces without some of those guides in place (although I’m a firm believer that many large organizations have held on to artificial tokens of productivity that can be quite detrimental to morale). But working on such a small team with such a focused goal was quite refreshing. I had worried about narrowing my scope to a single project for the next few years, but that too has been rewarding. Rather than a shallow pass over a complex project with several entities contributing somewhat blindly, our team has full view of the problem and it is our mandate to solve it.

After having done this now for a few months I can hardly imagine going back to my old work flow. The problems we are solving have multiplied and deepened and my work has actually seen a huge range despite working on this one problem. The work I am doing will be meaningful to the people that use it (hopefully that includes as many people as possible), but it has also been meaningful to me. I care more than I ever have about the success of this work. And the reward will be happy users that look past what I have designed and find meaning in what they are able to create with it.

What have been the biggest obstacles jumping from the two worlds?

Everyone develops a particular skill set, but you have to be able to work closely with a broader team that will get the project done. The range of expertise within the agency-side design community is more focused. Any designer worth his salt needs to understand print, branding, interactive, and motion. The start-up world requires a different set of fluencies. I’ve had to bring myself up to speed on front-end code (building interaction and interfaces), back-end code (managing data, structuring information, etc.), investing (seed to series-A and beyond), and the social web (the psychology and conventions of building social space on the web). I hardly have enough time to learn everything I need to, but I read everything I can and have picked a few skills to amp up (UX, front-end code, product design). My co-founder has been a great model of someone that absorbs as much info as he can about the skills on the periphery of his particular discipline. He is a product and business development guy but can talk shop about every discipline on the team.

What would you say were the biggest influences to help you make this transition as smooth as possible? People who helped you, classes (even if they are digital), or even role models who you follow via social media?

It’s all people. Everything has been about the people. My interest in pursuing this career path was because of a professional acquaintance that had made the transition from designer to founder and was willing to become a friend and mentor. He led me to other gracious and willing mentors and it continued from there. In a recent blog post, I give a linked list of some of these people.

But I will say that the path was anything but smooth. I worked tirelessly all summer to get to Skillshare classes taught by New York tech scene luminaries, met tons of people for morning coffee and advice, interviewed maybe a dozen times. Some of those interviews extended over weeks and I can’t lie, I felt crushed when a few in particular didn’t work out (now very glad that they didn’t). I was doing design and product work before an interview just to show up with something of concrete value and relevance rather than showing them a portfolio of old and semi-relevant work and asking them to project. It was exhausting and disheartening and even now I have those same feelings in regards to getting this product right. It doesn’t end but the fight to get over the next wall is what makes my work worthwhile and good.

For student designers, what would you say for those wanting to make this jump as early as possible? Do you believe that there should be a buffer period of learning the basics (of print design)? To use as a measuring stick, would you say that a designer would have to spend some time in art school or pay their dues at an agency first?

This is a tough one to answer. In building a company, there are a lot of tensions that may mean that design has to take a back seat on occasion. Sometimes the benefits of a rough iteration process outweigh the benefits of a slow and careful refinement process. For someone coming out of school, working with a very early stage company might lead you to develop a very specific start-up friendly skill-set, but your overall design ability might suffer. These kind of designers can be extremely valuable— they understand user testing, iteration, and the development process. But they often lack an understanding of brand, user experience and refinement. It’s a matter of knowing your goals early on. If you want to craft beautiful experiences that really differentiate themselves on an emotional level, it might be good to spend some time in an agency where design standards are high and you can be mentored by top notch talent. Of course, this is the path I took so I’m biased here.

Wander has been receiving plenty of buzz these past couple months. Do you have a timeline for releasing more info on what it is or will be?

We are building ferociously and will have updates coming soon. I can only promise it will be worth the brief wait.

How big is the Wander team? And how did putting together the team come about? 

Wander is currently six strong. Jeremy (CEO and our business and product guy) had built another service called Dinevore. He brought along his back-end dev from that project, and we recently found our full time front end guy who has an impressive resume of his own. We have a killer iOS dev and a project manager slash community manager. Every member of the team has some legitimate experience or connection to design. 

I was introduced to Jeremy through a mutual friend, another great designer that had changed paths and joined a start-up and is now at Facebook. The rest of team team came about the way everything comes about: connections, relationships, and some relentless hustle.

I’ve wanted to know about how you handle this medium/balance that most cutting-edge startups seem like they must deal with. The world is so “now, now, now,” instant-gratification-hungry and the times are changing rapidly. What is it like having to balance how fast-paced you have to work and adapt to the environment of the world of apps, while still making the right choices and a great product?

It’s always a struggle. But design is foundational to the product we are building so it’s more a matter of editing than cutting corners. There have been things we could build now but have held off because we know we don’t have time to do it right. The core of the product is largely in place and although I see every wonky detail that needs some loving, we do have a pretty refined and beautiful experience.


1 And apparently: he’s an eagle scout, as well.

  1. keenancummings posted this
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