An Interview with Keenan Cummings

There are three types of designers in this world: Those who do design, those who do good design, and those who get design. The first two are pretty common, but it’s rare you’ll come across someone who really understands what design is all about. Having spoken with Keenan Cummings for just the smallest amount of time, it’s clear to see that he’s one of the elite – Keenan doesn’t just design, he communicates. He communicates brands. He communicates emotions. He communicates ideas.

And he’s pretty darn successful at it too – You’ve heard of Keenan Cummings Interview

Hey Keenan, thanks so much for joining us on The Industry. Tell us a bit about yourself and the work you’re doing.

I’m the creative director and co-founder of a startup called Wander. My role covers everything from product design, UX, UI (web + mobile), and branding. And then I pitch in on content strategy and copywriting as well. It is intense, and the most compressed and rewarding learning experience I’ve had in my career.

How did you get into design? Was it a case of being a creative kid, and that evolving, or did you only get into it later on?

Design came later for me. I skirted the required art classes in High School. Somehow a semester of choir (a weird time in my high school years) and an electronics class covered the Arts requirement. It says something about creative education. Sir Ken Robinson talks about the need to discover creative talent as early as possible and tailor education to fit. I didn’t have much creative encouragement coming from teachers or mentors. What I did have was a couple of parents who supported my schizophrenic forays into one new hobby after another. Every six months or so I would sell my soul to a new pastime — pots, yo-yos, skating, BMX, Magic The Gathering, Star Wars, Football, Basketball, guitar, wildstyle graffiti (my first brush with typography, all done on sticker paper — I wasn’t all that deviant). It was frenetic and they supported every change whole-heartedly. I would be buying new gear or materials, plastering my room with stickers, digging dirt jumps in the yard, waxing curbs, and annoying the neighbors with band practice. One of my later hobbies was building a small T-Shirt brand. They helped me get a couple bottles of emulsion, some wood frames, and a few blanks shirts. I did the art, printed negatives on acetate sheets, stretched and coated my own screens, developed them in my closet, and printed on the floor of the garage.

For me the most valuable thing I came away with was an ability to search, to never be satisfied, and to follow my gut. Sometimes passion and wisdom don’t quite align, and being too careful, too frugal, too conservative, and too wise can mean you miss the chance to explore what you really love. I got to college, took a few design classes, and fell in love. There was no hesitation to jump in and learn as much as I could as I had done many times before.

Wander Postcard Project - Keenan Cummings Interview

Let’s talk Wander. What is it, why is it, and how did it come to be? How beneficial is it, in your opinion, for designers to have projects to call their own, rather than simply doing client work all the time?

Place is a really interesting and powerful component of who we are. Everyone has places they tell their story, that provide a setting for potent memories; places they feel ownership of, where they might call themselves a regular; places they aspire to visit, or just follow, and read about and are forever curious about. Where you’ve been, where you are, where you are going, and where you aspire to be all say a lot about you.

Sure, I’m a designer, but the fact that I was at one time a skater, a Star Wars geek, in a rock band, and the fact that I am interested in trying my hand at film and photography and writing in the future — this extended timeline on identity that reaches into our pasts and futures matters as much as where we are now.

Wander is about expressing and telling that personal story through place. I care deeply about this idea that the person we aspire to become is as important as who we now are and who we have been. There is something deeply rewarding in living our lives in the context of a broader story, and feeling like we are directing the arc of that story. At it’s core, Wander is about storytelling.

I was lucky enough to find and team up with Jeremy, a co-founder and mentor who shared these views and wanted to build a strong product that combined distribution and experience, growth and depth, tech and brand.

I did spend a few years doing client work, and there is a lot I loved about it. Whether you are in an agency or building your own company, I’d say personal projects are invaluable. No one has time for them, but some people manage to get them done. Being in a position to vet and hire, I’d say that personal projects and writing are the first things I look for. The things I am most impressed by, and the work I am most proud of in my own folio, are those projects that may lack the polish and budget and big name client, but are self-initiated, passion driven, and thoughtful. That is where you see who a person really is.

Now, when the first Wander splash page was launched, it received a bit of criticism for having no real information about the service, but still encouraging users to sign up. Now, there still isn’t much information about the service, but it’s getting a lot of praise because of all the awesome artwork over on the blog. Can you share the reasoning behind these marketing decisions? How effective have you found them to be?

We’ve undoubtedly been lucky with how well our early marketing has worked. But it also came with a lot of careful consideration and planning. The first launch we did was the Utterly Pointless Leaderboard. It had no real information about the product, but offered people 100 points for signing up, and then more points for sharing on social networks. There was also a cow at the bottom of the page that you could click for a single point per click. The response was amazing. It worked because it was a tongue-in-cheek jab at the launch pages that tried to build in viral loops by promises of early access or other uninteresting rewards. The users were in on the joke.

Ultimately, it is about respect for the user. We make sure that each time we ask something from our users, we give them something valuable in return. That Leaderboard was a good laugh and people were happy to share (our highest scores reached ~15 billion points). We’ve done other campaigns since then, and each time we work to repay the users with a rewarding experience that matches the value of their contribution.

This type of brand building is very much a part of my background working in agencies, but it is counter-intuitive to a lot of people in the startup world. The technological veil that has long surrounded tech companies is withering. It’s an artificial contract to believe that a brand built on an internet product is any different than a brand making jeans. There are differences in execution, but the principles are universal. Users are ready for a tech product that has a strong brand that transcends the functions of the app itself. I think we’ve already seen how people identify with the ethos of Wander before they’ve even seen the product. That is a powerful way to build a long term relationship with a user and web companies haven’t done that very well yet.

Neighbourhood - Keenan Cummings Interview

You’ve worked in all kinds of roles, starting out in a small agency, before going in-house at a big corporation, and then back into the agency world, only a much bigger one this time, and now Wander. Which of these has been the most creatively fulfilling? And for balance, which has been the least creatively fulfilling?

I’ve been in almost every kind of creative job this industry has to offer, and I look at it as an iterative process on what I want out of my career. The two-man shop I co-ran was the closest thing to a startup and I learned to run a business, and left with an understanding of how critical it is to trust the people you work with.

Then I went in house at Johnson and Johnson, and learned to love the social, economic, political, and even scientific depth a design problem could have. I did a lot of strategy work, which fed my brain in a way that the aesthetic work had not. It prepared me to think about and design product, where the considerations go much deeper that the execution. Once I had gone that deep into a problem, I was no longer satisfied dressing up the surface. I also learned how amazingly difficult it could be to get work done in a corporate environment. Too many conflicting interests.

Then at VSA, I got to do high level work for some of the biggest brands out there — Sony, Converse, IBM, Chicago Cubs, etc. I learned to do really solid work and to do it fast. But ultimately, I wanted to get deeper into the problems I was tasked to solve, and I wanted to own the project in a way that client work wouldn’t allow. Each of these jobs trended toward me building something from the ground up. I’ve finally found where I fit.

Where do you see yourself, and the industry, in, say, 5 or 10 years?

I enjoy thinking more about the macro economic trends that will reshape our lives. I happen to think the creative industry is ahead of the curve on this (of course a biased view). But overall I think we are moving into a new era, akin to the shift from the pre-industrial town to the industrial world. Jobs are being displaced by the efficiencies of technology, and we are going to find ourselves without enough “productive” work to keep ourselves employed or occupied. The solution will not be to create more factory jobs or entice us to consume more. We will have to rethink our notion of what productive work is. Think about it this way: 150 years ago, the work we do would have been considered an irrelevant waste of time. If you weren’t feeding the population or advancing science, you were a non-contributing dreamer. Similarly, the next generation will see people dedicating their lives to things that look to us live unproductive time wasters. Some people will play video games for a living (sounds absurd, but 10 years ago so did blogging for a living). Our job will be to create the economics that support this.

That is why I think our industry is ahead of the curve on this. People are starting to ascend Maslow’s Hierarchy of Needs. When food and shelter, safety, community, and self-confidence are a baseline condition we can provide to everyone*, the only thing left is self actualization and creation. More and more people will become creators and makers. We will button our shirts, tie our ties, and hop in self-driving cars on our way to the office to write poetry, play games, draw and paint and mold and build.

It might be longer than 10 years but already companies like Etsy are changing the notion of what it means to have a career. Interestingly, advertising (in its current form) seems less relevant in a world where more and more people create and have a direct connection to their end user or customer. The economic loops are getting tighter and there isn’t much from for these arbiters of commerce.

* I have to acknowledge the unfortunate truth that many are left behind in the process. As William Gibson said, “the future is already here — it’s just not very evenly distributed.” But I am also optimistic about the pace and fluidity at which technology is able to be distributed. It’s not perfect or fair, but always getting better.

Icons - Keenan Cummings Interview

If you could change one thing about your career to date, what would it be?

Early on I put a lot of faith in a system that would take care of the dutiful worker. Put in the time, do good work, wait for the promotions and opportunities. I thought talent was everything, and a better career was continent on better work. I quickly realized that talent is merely a prerequisite. If you work in an industry where everyone is good, everyone cares, everyone works long hours, you can’t expect extraordinary results if your hard work is the ordinary. It was only when I started to build an entire body of work and reputation outside of my 9-5 that thing really started happening. It is almost like having two careers simultaneously, but it really is late nights and weekend projects that define you. Now I pour myself into Wander, but I make sure I make time to write, and am even working on a project to benefit the interactive design community. All of that stuff feeds into itself and makes everything better.

My advice to my freshly graduated self would be to not expect anything from the industry. Everything and anything is available, but it will not come to you. Go get it!

If you hadn’t become a designer, what do you think you’d be doing now?

Anything that allowed me to reinvent myself regularly. Design allows that. I’d probably just do something new every few years. Design is a very loose tie that holds together so many different things I’ve been able to do over the past few years. It’s an extremely flexible career.

And finally, for those looking to get started in the big bad world of design, what tips or advice would you give?

I wrote this article on my blog almost as a manifesto. Here is an excerpt:

“There are no tricks of any trade. There is volume and consistency. There is kindness. That’s it. You have found something that you are pretty good at, and that you care a ton about. That gives you options to create any kind of career you want. Really. Honestly.

Start now. Be relentless. Write. Read. Make. Mimic (but credit your sources). Just don’t buy into any advice that tells you to be loyal, pay dues, bide your time. That is old-timey wisdom that has no real substance. Think about it. Is the price of entry into a creative economy boring, soul-sucking, back-breaking, passionless labor? No! There will be pain, but you’ll learn to deal with it as you go because you love the end result.

Unless you know exactly what you want out of the rest of your career, I recommend you don’t slow down, don’t follow the wisdom. Learn to learn fast. Learn to love something and do the crap out of it.”

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