Jesse McMillin: Inside Lyft’s Design Process

If you are looking for a dynamic industry that is changing the future landscapes of cities, look no further than transportation. Jesse McMillin, VP Creative Director at Lyft, understands this better than most. Since he joined the company in 2014, Lyft has evolved from a simple ride-hailing company to a leader in developing autonomous technology. And McMillin,  no newcomer to the world of transportation after nearly seven years as Creative Director at Virgin America, where he created there iconic #safetyDance video, is helping Lyft navigate the path ahead.  

99U contributing editor Dave Benton sat down with McMillin to get a better idea of just what Lyft looks like from within and how it stays true to its fun personality while developing a brand sophistication befitting a company leading the way in autonomous driving. 

How is being Creative Director at Lyft different from similar roles you’ve had at other companies?

I haven’t worked at a truly technology-focused start-up before, although I had that “transportation meets experience” world at Virgin America. At Lyft, it’s the combination of being a technology start-up and, at the same time, a human-driven company that is unique and what got me excited about the company in the first place.

Does having your headquarters in San Francisco make a difference in how Lyft operates or the company culture?

There’s the obvious answer that we are in the technology hub and San Francisco  has a history and culture of progressive thinking. A lot of brands draw off that. It’s also one of the more beautiful places in the world with a positive, inspiring atmosphere and that attracts talent from all over the world. It’s a community with an international perspective. When you think about how transportation works, for example, you get insight from people from different places. Also, San Francisco is an interesting transportation city. We don’t have a super easy and connected system, but we do have a dense population who need to get around, so it’s an interesting petri dish for thinking about the transportation systems the future is going to need and the way a young urban person is starting to think about the options they have.

Having started your career in a hands-on design role, what is the biggest difference between directing a brand and making the piece of design you’re crafting?

When you are really trying to think about the creative direction for a brand or a company, you have to be a fan and an avid user of the thing. You have to want to dive into all the little details and experience it as your audience would. You also need to have a clear point of view that you want to communicate. I think a lot of brands fall down when they are trying to do too much for too many people. If you have a singular thought that you want to express and want to keep that at the heart of what you are doing, it helps to align them. The brands I love have strong points of view and know exactly who they are.

There are different types of creative directors. Some are more definitive and lead from a position of “This is my vision and we are all going to do this.” In my experience, those types of leaders have to  inspire people and keep them onboard. Then there is the leader who is an activator and elevator. One who leads from a place of keeping the energy at a certain point and keeping people rallied around a feeling of where the group as a whole wants to go. I fall more into that second camp.

Has the growing size of the design team changed the way you lead the company?

That’s one of the things that I find exciting and challenging at the same time. The pace of growth has been impressive, and it brings so much opportunity with it. A lot of people thrive off that enthusiasm, but it also brings chaos, so as a company we have to watch that we grow smart as well as fast. When I came onboard it was a small scrappy group, but we have got a lot more sophisticated and dynamic with the channels we are talking to people in and we’ve had to grow as a team and bring in the right type of people who are capable of working that way. 

Lyft has changed a lot since you started there in 2014. How has the direction shifted?

For me, it was about helping the brand grow and mature without losing its personality. Take this wild, fun entity that’s been born and continue to help it grow and put some structure around it but do it in a way that doesn’t kill what was good at the beginning. That’s been my mission, and I think we’ve been doing a pretty good job about it so far. It’s not like you get it right and then you’re done, though.

You’re always evolving the brand. We need to keep crafting it, refining the things that can be taken to the next level, continue thinking about the vibe and aesthetic of the brand by keeping it fun but also click that sense of sophistication up a few more notches, especially when you talk about autonomous technology. If we are going to play into that world, as a company we have to think about what the vision will look like. We have a unique opinion about that, as it’s not just about the technology but also about the people. Our vision of the future is one where cities will open up more because you are not building solely around cars, but thinking about transportation as a service. Those conversations are where we are now.

Lyft has an increasing message of social good. Is this new or has this just gotten louder?

It’s gotten louder; the company has always been about values. We have founders that embody a feeling and vibe that they want to show up in the world, and the people who collect around them believe those same things. What we’ve seen is that as the brand grows, it reacts and develops to the world around it.

From a personal perspective, is it hard to see a brand you worked on and were emotionally connected to (Virgin) go away?

I initially felt sad as I obsessed about it for so long. But for me, if it wasn’t going to be done and done great, it’s better it’s not done at all. There’s a cycle of things. Embracing failure and loss is part of that. Probably better that Virgin sunsets than it just peters out. If it’s going to end, it’s better done on a good note.

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Take Back Your Weekends (and Leave the Work at Work)

Weekends aren’t what they used to be. And it’s become a serious problem.

That’s the message of Katrina Onstad’s new book The Weekend Effect: The Life-Changing Benefits of Taking Time Off and Challenging the Cult of Overwork. Onstad, a Canadian novelist and journalist who has written for the The New York Times, starts off by documenting the origins of our 64-hour escape from the office (Thank you: religion, unions, and Henry Ford). Then she dives into the ongoing struggle to step away from our smartphones and make the most of that time, with compelling stats, quotes from progressive CEOs, and anecdotes that will make you nod in agreement or shake your head in recognition.

Not that there’s much chance you’d argue with her thesis. Nearly 40 percent of Americans reported working 50 or more hours per week, putting us far ahead of our European counterparts, with less to show for it. But that’s starting to change. Onstad interviewed leaders who are capping workers’ hours to brilliant effect (including Jason Fried of Basecamp and Dustin Moskovitz, formerly of Facebook). And she offers myriad ways we can reclaim our leisure time with meaningful pursuits, as opposed to another Netflix bingefest that leaves you wondering where the weekend went. Here she speaks with 99U about her findings. 

Early in  your book, you compare the United States and Canada to typical working hours in other countries. What stood out to you?

The one idea that surprised me is that shorter-hour cultures are more productive, and have stronger economies, which seems counterintuitive. But over and over, researchers have discovered that after about 40 hours a week, our productivity drops off. Sometimes people can go through crunch periods, particularly in the creative industries: If you have a big project, you may be able to fight through it and hit 50-60 hours for a few weeks without a degradation in the work.

But it’s not sustainable beyond that. It’s not just the health issues that arise, with exhaustion, substance abuse, heart disease, and all the physical ramifications of overwork, but people start to introduce more errors. So the argument in favor of overwork becomes much more of an emotional and social-status argument rather than what we know about how people work and how to get the best out of employees. Germany has a short-hour work culture and is one of the strongest economies in the world. Mexico and Korea have the longest hours and are among the least productive. The U.S. and Canada are somewhere in between.

It’s really interesting the way a work-first mentality can grip an entire nation: France recently passed “right to disconnect” legislation that essentially says that after 5 or 6 p.m. and on weekends, your boss cannot contact you unless it’s an emergency. We’re so tethered to our workplaces and our devices that that concept seems almost sacrilegious or a sign of weakness, but France is recognizing that asking people to work crazy hours just isn’t helpful economically.

Much of the efficiency research cited in your book relates to manual labor, which isn’t surprising because creative work is really hard to measure. Has anyone tried?

It’s definitely hard to gauge. There’s a whole body of research around wartime industries and mechanized environments that are easy to measure, but with creative workers we have to look at case studies. In the book, I talk about the Electronic Arts  scandal about 15 years ago where programmers in the gaming industry were working 70-80 hours a week and completely exhausted, and not being compensated for overtime.

What happens in those environments is this conflation of work and play. As creative people, we often think of ourselves as artists, and we’re even encouraged to do so—you’re supposed to do it for the love of the job or the love of the art, which sets up a dynamic that’s really open to workplace exploitation and exhaustion.

If you love your work, it’s really hard to turn it off, and there are all kinds of forces at play that are opposed to you turning it off, including your own sense of self. If you’re a creative professional and you’re in a museum and you get a note of inspiration, you might think, This is something I need to post to Instagram. But if we’re always feeding our “work selves,” it takes us out of the present moment, and that has really bled out from the creative class into other spheres—everybody is curating their brand, from the designer to the accountant.

To be clear, I didn’t write this book to scold people, just to point out that it can be a grueling way to live, and it’s a gateway to missing out on so many other experiences of the world, if work is the driving force of every experience, including leisure. For me the lens is the weekend: Can we protect 48 hours, where we’re not just in promo mode? Is it possible anymore, and what would that look like?

And you’re not just asking questions: Your book shares some stories of Jason Fried, CEO of Basecamp, who embraces shorter weeks during the summer, and Facebook founder Dustin Moskovitz, who has had a lot to say about the topic.  

Moscovitz is a really interesting case, because he has spoken so openly, yet tentatively, because there’s still such a stigma around this idea that working less is a strategy for success. When he and I spoke, he talked about the early start-up days being insane and all the typical responses—back pain, living off of energy drinks, and feeling terrible all the time. He’s written about it on Medium, saying, “If we’d worked less, we would’ve done better work,” which is unfathomable to people on the outside. Now he has his own company, Asana, and he has tried to undo a lot of those habits by instilling some progressive workplace practices like not infantilizing workers so they can create their own schedules, and trying to ease up on weekends. And he’s modeling that behavior, which is one of the most important things leaders can do, actually showing employees, “I’m off-line, and that grants you permission to go off-line, too.”

For years, we heard people focusing on the concept of “work-life balance,” but lately I’m hearing more people say that work-life balance is just a myth. Has your research led you to believe that?

It can definitely feel like one of those unattainable goals that may set you up for failure—that thing on the horizon that you’re always chasing. So I don’t know if the concept of work-life balance is a useful idea. Because it’s all life, right?

What I don’t like in that equation is that it almost encourages this masking of our real lives. In the book, I mention a study that focused on men and women in a high-pressure consulting firm: The women would clearly articulate to their bosses, “I need time to take my child to the dentist or to attend a funeral,” whereas the men were doing the very same things, but doing it invisibly, and they were rewarded for not saying it out loud. What I would hope, instead, is that we can shift workplace models to something holistic, where we acknowledge that we’re people all the time, and that our lives are going to infringe on our work and our work is going to infringe on our lives, but when we’re not working, we use that time in a way that’s really healthy, and that we’re not expected to be on call 24-7. Because the idea that work will always be present is just not sustainable.

The last half of your book discusses ways for people to embrace the weekend and really make it count. Are people really struggling with how to spend their weekends?

There’s some real anxiety about free time, and there must be something to this compulsion to fill every minute and commodify it, right?

The original scaffolding of the weekend was obviously religion, and the essential point of congregation was to stop working, and come together. But now, in our secular society, people don’t have that same compulsion. Today, many people spend the entire time “decompressing,” and research suggests those extremely passive forms of leisure don’t actually make you feel better; they just provide instant gratification or quick hits. As part of that Sunday night let-down, people think, “I went to the mall and I got a pedicure—why don’t I feel any better?”

So I was very interested in this category of “active leisure,” which has much longer-lasting benefits, and the biggest piece of it was socializing—finding real human connection. We know that rates of social isolation are higher than they’ve ever been; while we may be really digitally connected, we’re not necessarily connected to one another in a meaningful way, and that’s an urgent problem for our own happiness and for the health of our communities.

That’s why I wanted to talk to people who are doing creative things in their own communities, and they’re palpably happier as a result. I always thought volunteering seems so pious, and who wants to spend their weekend doing it, when it’s so boring? But it turns out that volunteering actually creates the sensation of more time. If you don’t want to spend 5-6 hours every Saturday volunteering at a soup kitchen, then try a one-off event here and there, because there’s incredible value in that.

In your book, you share your own struggle with carving out time, and making weekends feel meaningful. How’s it going for you?

Well, as it turns out, my book is right! Which is incredibly vindicating. The biggest things for me is being attentive to how I spend my time, saying, “No, I don’t need to bring my phone with me when I go to the park,” and “It’s OK if I’m completely off-line for 24 hours—the world is going to continue to spin.” My family has really pulled back on scheduled activities for the kids, which is a huge piece for people who feel crunched. It’s OK to let your kids be bored, and set them loose—you don’t need to spend every minute shepherding them through the city. I’ve started volunteering with a writers collective offering workshops in marginalized communities, started to make more time to enjoy parks and greenspace in the city of Toronto. And I’m forcing myself to not rely on Netflix to fill empty windows of time, but to actually look at the big picture, and ask: What do I want my life to be?  

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What I Wish I Knew at Every Age

When asked what we regret in our careers or life to date, it can be difficult to formulate a response. Not only is it tenuous at best to try to pinpoint the exact moment where we should have pursued this direction instead of that, seized one opportunity over another, or taken a risk over a guarantee, but each decision – whether later deemed good or bad – has led us to where we are today.

Regrets may be futile, yet there is a particular variety of wisdom that can only be gained in hindsight. As we move through each decade and navigate changes and challenges in our career and personal life, we begin to identify our supposed missteps – big and small. We begin to understand how our own doubts, insecurities, self-limitations or expectations may have been getting in the way all along, and take such insight into the decades ahead of us.

Without such experience, it can be difficult to gain such clarity around what we might be doing wrong or what might be holding us back in our work, side projects, relationships or health. But sometimes the experiences of others can help speed us along.

In an attempt to gather the lessons we can only gain through time, we’ve asked several creatives – including Lisa Congdon, Debbie Millman, Tina Roth Eisenberg and Ken Done – to reflect on what they wish they knew at every decade.

I wish I knew in my twenties…

1. To stop worrying about other people…

 “We spend a lot of time in our twenties trying to please other people or worrying if we are doing the right thing. There is something about getting older that just makes you think to hell with that, I’m going to do what I want to do because what have I got to lose? That was definitely my experience – I quit my job to be an artist, and I owed it to myself to try.” – Lisa Congdon, illustrator and author, Portland, Oregon

2. That there’s no rush…

“The pressure to do things quickly or have success happen right away is ingrained in our culture of instant-gratification, but really your real life is so long. There are so many things that you can do and there is no reason to panic when you are in your 20s. Sure, you only live once, but you also have this long life ahead of you.” – L.C.

3. You can create the world you want…

“I really wish I realized sooner that I needed to be an active participant in creating the world I wanted. I was floating and going with whatever came my way – I wasn’t very active about thinking about what type of person I wanted to be, or what environment I wanted to work in. My daughter was my biggest career catalyst, and I wish I had that wake-up call earlier. It never occurred to me that you could start companies sooner – when your life is so much easier and you have fewer responsibilities.”  ­– Tina Roth Eisenberg, designer and founder of CreativeMornings and Tattly, New York City

4. That careers are never linear…

“I used to think my career would be very linear, but even in the almost eight years since I graduated, I’ve worked at a branding studio, done illustration and product design, worked in-house for several large brands, and now as a freelancer. And I don’t necessarily want to be a graphic designer forever.” – Ben Wagner, independent designer and art director, New York City

5. No one has it all figured out…

“Acknowledge that no one has it all figured out – even your mentors, bosses, or design heroes – and that’s okay. The important thing to remember is to keep creating. Spend more time and energy on making your best work, and less on comparing yourself to others.” – B.W.

6. To stop being so hard on myself…

“I wish I knew not to be so hard on myself and not to beat myself up so much. I wish I knew not to take everything so seriously in terms of my worth and my value. I wish I had spoken up more and stuck up for myself.” – Debbie Millman, writer, educator, designer and host of Design Matters, New York City

7. Skills are more important than grades…

“At least as a creative, the skills you acquire in school are more valuable than the grades. I wish I tried to learn more while I still had access to those resources in a safe and nurturing space.” – Adam J. Kurtz, artist and author, New York City

8. Not to worry so much…

“Shit isn’t real yet when you’re in your 20s. Your early 20s problems will feel really insignificant soon. Try a bunch of stuff, be a little reckless, smoke weed one time, kiss someone nice, stop trying to be cool – it’s not working, it never works – and generally let yourself live.” – A.J.K. 

9. Everything will be okay…

“I do wish I could tell my younger, confused, insecure, lost, and angsty twenty-something-self that everything will work out okay. I will meet the perfect person that I can share my life, passion, and work with, and that I will someday get to do something I love everyday with people that I love and respect, that I will get to create beautiful things that inspire people in their everyday lives.” – Angie Myung, co-founder of Poketo, Los Angeles

“If I were to see myself in my twenties, I might say hey, things are going to be okay. Do what you love, work hard. Know that creativity is everything in life. Even in business, creativity is the driver. It’s really what makes you whole, in that inspiration and that creativity.” – Ted Vadakan, co-founder of Poketo, Los Angeles

10. It’s probably not the worst decision ever…

“When I left New York to come to Australia [after falling in love with Melbourne], I think there was a lot of fear in that. When I was retouching images of dog food or working as a kitchen hand, I definitely felt I had made the worst decision ever, but it’s so hard to be in touch with those feelings now, when I couldn’t imagine life any other way! All will be revealed in the fullness of time.” – Jeremy Wortsman, Director of Jacky Winter, Melbourne, Australia

I wish I knew in my thirties…

11. To think seriously about whether I wanted a family…

“I had two miscarriages because I was 39 and 40. I’m fine about it, but I tell women all the time now that if you want to have children later in life, freeze your eggs or start in you’re early to mid-thirties because often it’s too late by 39. I try to help people avoid that if at all possible.” – D.M.

12. That mistakes always count for something…

“I could talk for hours about our failures trying to expand into new areas by solving problems that we only imagined existed, or disasters hiring the wrong type of employee or not putting aside money for tax, but those are lessons you have to directly experience to really learn from, as each business is so unique. At the end of the day, the business itself is your biggest teacher.” – J.W.

13. To take care of myself…

“I recently had spinal surgery for a herniated disc, and it was one of the most agonizing experiences I had ever been through, and while I was in the midst of the experience I was feeling lots of regret. Regret that I didn’t exercise enough, or eat right. That I sat too much at work or in the car. It took nearly two years to fully recover, but in that time I became so much stronger, and I now know my body on a whole new level.” – J.W.

14. No experience is wasted…

“I had a career in education before I turned to art, so I thought I was throwing all this experience away to go do this other thing. But the good news is if you are going to change careers later in life or do something new, anything you’ve done before is going to contribute to you doing a better job at that new thing because you have all this life and work experience.” – L.C.

I wish I knew in my forties…

15. Aging is life affirming, not scary…

“It didn’t take me long to realize you know what, it’s actually affirming to turn forty. You’re always learning and that’s the key – it never ceases.” – T.V.

16. You can’t control everything, but you can adapt…

“You can’t control everything. My uncle used to say to me, that we are like grass; it bends, but it doesn’t break. Even in turbulent times or uncertain times, it’s good for people to adapt, to embrace spontaneity and go with the flow and bend like grass, but not break. Be open to change and accept it with grace.” – T.V.

17. How to balance trust and being accountable…

“There was one instance with Poketo where we maybe put too much trust in a person and we didn’t get what we needed. While I always see the good side of people, at the same time you need to be accountable for whatever needs to get done and not just solely relying on someone else. To grow as a business, you need to find a balance between being the captain of your ship and being able to trust your crew.” – T.V.

18. Compromise, compromise, compromise…

“For Angie and me, Poketo is like our baby. It’s something that we’ve been doing since we first started dating and there are difficulties in growing something together. There will always be disagreements, but what we’ve learned is to talk it out and come to a compromise. We need to be in sync to execute something new, so it’s never one-sided.” – T.V.

I wish I knew in my fifties…

19. To savor…

“Savor every day. Savor every day. Keep experimenting. If you want to do something, do it.”– D.M.

  20. You set your own rules…

“Now I’m approaching my fifties, I wish I knew earlier that you set your own rules. Part of why I worked so hard for so many years was this pressure to keep up. But I realized that was a pressure I was putting on myself – no one else was telling me that I had to work that hard or take on that many projects at once. We invent our own rules and we have control, which is pretty cool if you can orient yourself to it in a healthy way.” – L.C.

I wish I knew in my sixties…

21. To have patience and perseverance…

“Even the things I’m unhappy about in my life have allowed me to persevere and to be patient. I now know that things will take a lot longer than you think they will to achieve. If you don’t have patience or perseverance, you’re not going to be able to work.” – Maira Kalman, illustrator and artist, New York City

22. Wisdom takes time…

“Things get murky and confusing at any age. But you can’t have the kind of perceptions at twenty-five that you have at sixty-five, and I don’t think it would even be good to have that kind of wisdom – it might prevent you from doing all the stupid things that you should be doing!” – M.K.

I wish I knew in my seventies…

23. Every age has highs and lows…

“There are hills and valleys, some deeper than others, some higher than others. In your mid-twenties you’re convinced that you know everything. By your 30s and 40s you’re beginning to understand that this may not be so. For me, the 40s, 50s, 60s, and 70s have been filled with the desire to become a better artist.” – Ken Done, painter and designer, Sydney, Australia

24. You can be 77-years-young…

“I’m surprised to find myself with the chronological age of 77 when really I feel as if I’m still somewhere between the ages of fourteen and twenty-eight. The key to feeling young is keeping your eyes open and trying as best as possible to get the most out of every day.”– K.D.

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Design Director Alex Center Got a Masters in Branding at Coca-Cola

Giant corporations have a certain rep — they’re slow-moving beasts churning out mass-produced goods that ride closer to the center line than the cutting edge. The cool kids all want to work for the niche studios. But not Alex Center. The Coca-Cola creative and design director loves operating in a mass play market. “Transitioning from a small to big company has taught me everything I know about branding and selling products,” he says.

Talking to Center is like peeking through the walls of one of the largest corporations in the world. Over the last 10 years, he has experienced firsthand how the sheer size of a corporation like Coke affects the design process — something he is able to contrast with his days at vitaminwater before its acquisition by Coca-Cola.

A champion of in-house design teams, Center recently spoke with contributing editor Dave Benton about the way a designer can become a central part of a large brand’s journey over time in a way that is not possible for an agency, how Coca-Cola communicates the distinction between strategy, positioning, and visual design within its organization, and how his job changed when he went from working for vitaminwater to Coca-Cola.

Design is an inclusive term. How do you communicate the distinction between strategy, positioning, and visual design within Coca-Cola?

It all comes back to goals and intention: What kind of brands are we building? What do they stand for? And, ultimately, [how] do we want people to understand and feel about them? As a designer working for a company investing a ton of money in the formula of the product — the actual physical liquid that goes into the bottle that is going to reach millions of people— you’re talking about a lot of decisions, so you have to think about how design helps us achieve our goals and our mission.    

As designers, you have to ask yourself what the principals and intention are, and whether the work you are showing achieves that. Companies want people to go post about them on Instagram and feel like their brand is representative of the consumer’s mindset. In order to design things to make people feel that way, designers need to put themselves in the end user’s head. Often non-designers within a company fail to think about what the customer is going to feel when they walk past the product: Does it make them feel understood? Do they want to be a part of the brand? Do they want to pick up the product and try it for the first time and give us their money?

These are the questions everyone should be asking. It’s commercial art. The goal is commerce, but it’s more than the product inside of the bottle. It’s the brand that we want people to fall in love with. It’s the ability to make someone feel that they have to buy a Levi’s denim jacket instead of another denim jacket that’s exactly the same. For me that’s one of the most fun things about it. All the drinks in the cooler are fairly similar at the end of the day. They all quench your thirst.

I’m very romantic about the moment of truth in the beverage category. That moment when you get to that cooler in the back of a deli, you are faced with a choice of at least 20 different brands. I’m fascinated with why you make the decision to go for this, rather than that. You package what your brand is, and you try to charm people through your packaging. The strategy, the positioning, the visual design, and craftsmanship are all equal. At Coke you can’t go in with one without the other. The stakes are too high and the investment is at the highest level.

I’ve stopped saying “good” and “bad.” It’s either successful or unsuccessful. Let’s face it, there is bad design that is successful. You can debate what good design and bad design is until you are blue in the face. But you can’t deny that LaCroix, for example, is effective design. Or Sriracha. The brand of Sriracha is super strong right now, but I don’t think anyone would say the design is particularly beautiful. Branding is meaningful differentiation.

How did your job change when you went from working as part of a small design team for vitaminwater to working for Coke when they acquired the brand?

Everything changed while kind of staying the exact same. When we were smaller we had the advantages of being nimble and quick. When I started designing for vitaminwater, I would sit directly next to the brand director and the creative director would be just two seats down, so the approval process consisted of me simply showing it to the right and to the left. The decisions that were made were in the minds and bellies of the design and creative teams with marketing, and they were all sitting together. That made for some great products that got out to the world quickly.

When I compare that to the process of a publicly traded company like Coca-Cola — the time it takes to get things done, the amount of people involved in everything I work on, and the amount of testing and approvals, it can slow things down. Ultimately, only the best work gets through the funnel. When I was younger and working in a smaller environment, the funnel was super wide and we would throw things into the world that were really questionable. As a result there were some huge wins, but also some really arguable things we put out there.     Transitioning from a small to big company has taught me everything I know about branding and selling products. In the past I would create a design because I felt it was right for the brand and right for the business. Now I have to show that it is and why it is, which has made me a stronger designer. What I am doing has to strategically align with our business goals and objectives. A big part of my job today is getting people within the company to understand that where I am headed is the right place to go.

How has staying at one brand so long affected the way you think of branding?

Having worked for a brand for so long, I know that “branding” is not a singular project. Being a brand is kind of like being a rapper. Not a lot of rappers are loved because of their name and their first album. People love rappers because they put together a body of work over a period of time that they continuously find themselves connecting with. When someone says they are doing a branding project they think they are doing a logo and a look, but the brand is a moving, flowing stream…a marathon…a rap career…it changes!

Every single thing you do, every album, every tour, every tweet, and every decision you make, amounts to people either loving you and wanting to be a part of your orbit or not. The best rappers are the ones that have been able to find new and exciting ways over time to make people care. This pursuit started before I got here and will continue after I’m gone. But during the time I’ve been here I’ve been a part of making things that make people care about these brands. To me, branding is a series of moments: They are our versions of albums and mixtapes.

A lot of designers want to work on niche brands and stay away from the big commercial ones. You don’t work that way. Why?

I like things that are mainstream, and I love operating on a global stage. The bigger and the more impactful, the more exciting. You ask any rapper if they want more people to listen to their music and the answer is “yes.” The way to do that where it feels great is to get the most amount of people to listen to your music and not compromise while getting there. I remember in my earlier days, I physically went to see a billboard I laid out and I thought it was the coolest thing ever. So many people were going to see it!

I want to do work that the majority of people can interact with. My favorite designs are the ones that have the biggest impact, whether that impact is positive or negative. Just making people aware is huge. I’ve been coming in every day for 10 years and working on one thing, and I feel like I’m just now coming into my own. I feel like I got my masters in branding and design at the best school in the world, the Coca-Cola marketing department.    

How is design different working in a company as opposed to an agency and how does this affect the value you and your team provide?

I’ve never worked in an agency so I can’t speak to that experience. I know the client side really well and I’ve seen companies begin to bring design in-house because non-designers in companies are getting smarter and more adept at using design to accomplish and truly understand our business goals. Working in-house you get to be a part of the full picture. In an agency — no matter how close you are with your client — there is always that moment when the client walks out the door.

Agencies will always have influence and always be needed for an outside perspective, but in-house you are the person that drives that car. No matter how good an agency is, there’s always a sense of “inside-outside.” At the end of a day, we are not going to make a decision because our agency tells us to— it’s going to be because we think it’s the right thing to do for the brand and the business. Although it is ideally a real collaboration, ultimately the decisions come from inside.

How have you seen the world of design change in large corporations over your years at Coke?

When I went to school and studied design, being a graphic designer was cool but hardly anyone did it because less people had an understanding of what a designer did. In 2016, professional basketball teams filled stadiums full of season ticket holders just to unveil their new logos and uniforms. People really care about design now. Budweiser changes their logo on their packaging and it’s on late night TV. That sort of arena of “branding as a sport” is amazing. It’s also made the everyday person a bit more critical of what we do. But it has ultimately given us a more valuable spot. If you look at the big companies like Target, Nike, or Coca-Cola, they literally have 100+ people in-house designing and these people are laying out the future of these companies.     Everyone in the design community always said they just wanted a seat at the table. Now the seat is ours. Designers now have positions at the highest level inside of our world’s biggest companies. This is the golden age of design. The flip side of that is that now everyone feels they have the platform to vote “yes” or “no” on something you create. Creativity can be very objective! In this arena there is not a lot of room for error, especially in 2017 where you see businesses who make small mistakes pay so severely.  

Have you had a moment in your career where you feel like you “made it”?

I felt like I had 1,000 percent achieved my goal when I was working with rappers and athletes [at vitaminwater]. We were the hot brand back then and I had the dream job of all dream jobs – doing what I loved and getting to make stuff that people across the world would see. I became confident in myself because I was confident in my job and who I had become. I felt like there was nothing cooler and nothing better than what I was doing.

50 Cent was an ambassador for vitaminwater during your early days working with the brand. Have you got a good 50 Cent story to share?

The most memorable was my first big photoshoot with 50 Cent where I was the art director. We had spent weeks preparing for it. When he got to the set people had built me up as the genius behind the shoot and introduced me that way to 50 Cent. He sized me up and said, “So you think you’re pretty special, huh?” I won’t forget that moment…I’m a huge 50 Cent fan.

You’re a big Hip Hop fan. What is your favorite Hip Hop quote that relates to design?

I end all of my talks with the same quote from Lil Wayne. The quote is from his song Dr. Carter and the quote is “Gotta work everyday, Gotta not be cliché, Gotta stand out like Andre 3K.” It’s one of my favorite Wayne songs where he plays a doctor giving advice to other rappers in an attempt to save the rap industry from its “death.” I love that quote because it’s about putting in the work, trying to better yourself everyday, all while making sure that you’re standing out from the crowd. This is great advice for any designer and something I try to remind myself on the regular. There are a lot of similarities between being a great rapper and being a great designer.

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Designers on Design: Debbie Millman

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In Praise of the Home Office

Early on a Sunday morning I’m sitting in my favorite space, a small outbuilding behind my house, in my favorite chair, a twenty-five year-old, medium-sized Aeron with a few small burn holes in the mesh seat. Even though it’s spring, it’s still cool outside. I’ve got my hoody pulled over my head, keeping the ole brainpan warm. I have nowhere to be but here. The red second hand of the school room clock mounted high on the wall ticks audibly, counting off the progression of moments, every one of which belongs to me.

Through the several windows I can see that the sun has begun to burn through the layer of clouds, revealing a patch of light blue sky—I’ll leave the exact color to my visual artist friends; to me it is reminiscent of the powder paint we used for skies in elementary school. A plane streaks overhead, gleaming and metallic, rumbling through the atmosphere like thunder. In the middle distance, a red-tail hawk circles, searching the canyon for breakfast; hummingbirds hover and dart, flirting and issuing their odd squeaks. A breeze plays through my neighbor’s invasive stand of tall bamboo. The stalks sway and knock together, making woody sounds like a marimba. From over the hill I can hear the throaty engines of powerboats and other personal watercraft churning circles around nearby bay, weekend warriors at play.

Here in my home office, the line between pleasure and duty is blurred. Weekend or weekday, there is no difference to me. Nobody counts my hours. My work is also my hobby. It takes as long as it takes. That someone is or is not paying me at any particular time is sort of secondary. Like most people, I work to live. But I also live to work.

This is where I do it—a 900-square foot patch of universe chock-a-block with photos, keepsakes, books and other familiar objects of personal history, most of it qualified as tax deductible, all of it mine to command.

Like nowhere else, when I am here I know who I am.  

***

Now it’s a little after noon. I’ve just returned from the house, where I threw together leftovers for my typical 15-minute lunch. Afterwards, I folded the whites and stuck the darks in to the dryer.

When I think about it, I come from a tradition of home offices. Both of my grandfathers—a lawyer and the owner of a clothing and shoe store—had offices in their homes, satellites to their more traditional workplaces. I remember being a little boy and swiveling around in their desk chairs, hunt-and-pecking on their clunky antique typewriters. In part I believe I owe my love of writing to the happiness of these times, my unexplainable attraction to the physical act of typing—the wonderful rachet-sound of the platen, the percussive clack of the keys against 20-pound bond, the ding at the end of each line heralding the need for the cleansing physical action of the carriage return. To type is to have the world at your fingertips—twenty-six neutral symbols to endlessly recombine. It is a task that requires both whimsy and precision. Another universe to command.

My father was an OBGYN. He had a home office, strictly for paperwork, in the basement of our rancher, the only place in the house he was allowed to smoke his cigars. The centerpiece of my dad’s home office was a desk his parents bought him for use in medical school—a blonde mahogany, Midcentury Modern kneehole desk with curved drawers by Heywood Wakefield, according to my research on the web. There is a matching Tambour door cabinet, on the back of which is stamped the manufacture date, May 1, 1954, two years before my birth. (The desk is too heavy to move.) As a boy I remember stealing down to the office when my parents were out for the evening. In the deep, double-drawer on the left side of the desk, my dad kept a stash of racy gag gifts given to him by friends—an oversize toothbrush with two plastic breasts instead of bristles, a windup penis with feet, a deck of cards with naked ladies instead of kings and queens.

When I went law school, my Dad gave me the desk and the hutch, for both practical and symbolic reasons. Hopefully, he said, it would see me through grad school with the same kind of success as he.

Of course, law school only lasted three weeks, but I was allowed to keep the furniture, which has traveled with me through forty years of home office incarnations. In Arlington Virginia, the desk was in the second bedroom of an apartment situated just beneath the flight path to what was then called National Airport—the entire building would shake. In Washington D.C., I lived in a basement apartment, and then in a loft, and then in a townhouse, the last for 12 years. My office was on the third floor; the desk had a nook within the front bay window, which looked out on the cityscape of a still-untamed section of town (in present times the Theater District), where hookers and crack dealers worked the dark corners, a different kind of natural show playing at all hours of the day and night.

Now my father’s desk has outlived him. For the past twenty years it’s been in this room, in San Diego, at the bottom-left corner of the continental United States, twenty-five miles north of the Mexican Border. The deep drawer is now full of vintage reporter’s equipment—defunct tape recorders, film cameras, old pads and other office supplies, not nearly so much fun as the booby toothbrush and other naughty bits of yore. In the hutch I have a ton of tear sheets from my years as a newspaper reporter and a few copies of the literary magazines I edited in college. I still remember sliding it open one time and finding multiple copies of a sex manual my father must have given out to patients. The authors were a husband and wife team. The photos were black and white. Naked, and without expression, the authors demonstrated dozens of positions, a sort of humorless kama sutra for the Masters and Johnson set.

In order to better accommodate the various pieces of hardware associated with today’s modern office, I have since added around the desk an eclectic mix of work tables and equipment stands, so that I’m nearly surrounded with surfaces—imagine a closeout sale in the office furniture department at Staples and you get the idea. (My original typing table, which used to hold a used, IBM Selectric typewriter, now holds the laser printer.) Swiveling around,  rolling my chair (over a plastic floor mat), I can attend to the different tasks and projects I have going simultaneously. Sometimes I imagine myself sitting in the command pod of a space ship, all the controls of my great solo enterprise at my fingertips—look at that, another reference to control.

Clearly a theme is emerging here. I am my own man, yes. But that also makes me nobody else’s man. Responsible to, and responsible for, only myself. Powerful and powerless at once.   

***

Nighttime now. These things take time, another reason I suppose I’ve spent so much time in my home office. The sky is dark. Stars have appeared. Somewhere across the canyon an owl is hooting. If I listen carefully I can hear the waves break quietly on the coastline, a half mile away.

After making myself a simple dinner of steak and greens, I’ve put up the dishes and returned the fifty or so steps to my office. Yesterday, I left the house to go to the post office. Today I didn’t leave the house at all; most of my time was spent in this chair. And yes, I am still wearing the sweatpants I put on this morning when I rolled out of bed. I will make sure to shower at the night’s end. I’m a home-based worker but I’m no misanthrope.

For the last few minutes, I’ve been trying to figure out a way to tally the number of hours I’ve spent in proximity to this desk, alone in a room with my thoughts and labors. With all the travel for work it’s hard to say, though I also know that for every week in the field doing research, I’ve generally spent several more weeks at my desk—making calls and arrangements, transcribing, doing further research, composing, rewriting and editing.

Struggling to find the right formula, I went to the doorway and looked into the darkness, in the direction of the hooting. One hot summer evening the owl had overflown me by only a foot or two—the whoosh was palpable in the immediate airspace and kind of freaked me out.

Standing there, I noticed one of the many photos of my son. A decade ago, he was working hard to become a point guard on the middle school basketball team. At an age where many boys dream of becoming pro athletes, he had a Lakers jersey with his name—SAGER—custom printed on the back. He was taking extra practices, working out with a coach, running several miles every day.

One afternoon when he was off at practice, I was sitting here in my home office, thinking I wished I could do something to help. One thing you (hopefully) learn as a parent—the kid has to take the all the practice shots and do all the math problems himself. You can’t do it for him. All you can really do is cheer them on.

In that instant, an idea came to me. I walked over to the desk and picked up a pen. I wrote it like this:

 

Hard work

Well enjoyed

Builds a man

Makes a life

Day by day

 

Though I wrote this with myself and my son in mind, the same can be said for building a woman as well.

It’s what I’ve learned after forty years of sitting in my home office, doing what I love.   

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What We Learned at the 2017 99U Conference

At 99U, we talk a lot  about the creative community and there was no better representation of that than the audience, speakers, and partners of the 9th annual 99U Conference. Together, they represented 661 cities spread across six continents who traveled to New York City for three days and nights of speakers, Studio Sessions hosted by top creative organizations, and rollicking parties.

While most events might wait until their 10th anniversary to throw a big anniversary celebration, 99U fittingly pulled out all the stops for our 9th edition. We had thought-provoking main stage talks from leaders at brands like Instagram, Airbnb, and Pentagram, on everything from the BS of design thinking to navigating career paths in this age of disruption.  

Then there were the Studio Sessions hosted by companies such as Spotify, BuzzFeed, IDEO, Refinery29, the Upright Citizens Brigade, Refinery29, ustwo, Dropbox, SYPartners, and Shake Shack. If you didn’t attend and you’re starting to feel a tad jealous, we apologize for what we’re about to tell you next—our closing party at the Museum of Modern Art went until the wee hours and featured a DJ set by Hot Chip.

The 99U Conference takes an inclusive approach to creativity. Whether you’re a designer, artist, marketer, engineer, educator, artist, CEO—if you approach your work creatively, 99U’s goal is to help you find the inspiration to build an incredible career. And we did have delegates from all of those fields and more, who heard stories of personal triumph in the face of career challenges, participated in hands-on workshops focused on learning specific creative and job skills, and walked away with new ideas that can make a real impact on their work.

To the 1,000 delegates who attended this year’s sold out event, thank you. And to those who are interested in attending next year, we’d love to have you. In the meantime, here are some of the best and brightest ideas we heard at the 2017 99U Conference.

Creativity is medicine.

“People need doctors. People need clean water. Is creative work as much of a deep need? I would say yes,” said Farai Chideya, author of The Episodic Career.

Challenge the world around you.

“You never see a person on a cycling sign. You see one on a wheelchair sign. You’re saying you can’t use that object unless you are that person,” said Liz Jackson, founder of the Inclusive Fashion + Design Collective, as she strode the stage with the aid of a cane. “We are disabled not by our bodies but by the world around us. It is a social construct. Disability is nothing more than a brand, the world’s ugliest brand.”

Speaker Mike Perry / Photo by Julian Mackler

Challenge censorious tendencies.

With his work, artist Mike Perry has challenged everyone from the FCC to 99U (we were asked to strike a ‘no obscene images’ clause from his speaker agreement). Even Playboy had to be persuaded to run one of his illustrations, which they eventually did with adjustments. “Drawing people is like [sex]” said Perry. “If you’re not careful, you might create a new life.”

Design is a foundation, not a fix.

“Initially, design was the ‘fix it’ team. ‘Can you make the experience better?’ But the best businesses are built with design leadership,” said Adobe executive vice president of digital media, Bryan Lamkin, who was product manager of Adobe Photoshop “before Photoshop had layers,” he said to raucous applause from the designers in the room.

Consider your inner Björk.

“Let’s re-envision the incubator model to foster cultural value, not just capital value,” said Julia Kaganskiy, the director of the New Museum’s incubator, NEW INC. “We don’t want to be the next Facebook or Google. Maybe we want to be the next Björk.”

Speaker Ian Spalter / Photo by Julian Mackler

Data doesn’t have feelings.

This is important because users—and investors, and customers, and colleagues—do have feelings about your product. “With data, you don’t know how you’ve made people feel about the changes you’ve made,” said Ian Spalter, head of design at Instagram, who made the best comparison of the day: “Design is about puppies. Data is about politicians. But there is magic to be found mixing intuition with statistics or art with science.”

You can’t plan for everything, so stop trying.

Selling your company often appears like a well-deserved ending to a long journey. But exiting isn’t always the victory it seems. Barbarian Group founder Rick Webb learned that lesson the hard way when he sold his company to a Korean conglomerate that went through an unexpected corruption scandal shortly thereafter. In his 99U talk, Webb candidly spoke about what it’s like to sell your company and then be faced with challenges that you never saw coming.

Keep it simple.

99U founder Scott Belsky, who had early-stage investments in Pinterest, Warby Parker, and Periscope, emphasized making products simple and accessible—and keeping them that way. Users flock to simple products, noted Belsky, then companies take users for granted and adds features to satisfy the power users, which alienates the users who flocked to the original simple product. “Products can be powerful enough for professionals, but accessible to everyone,” said Belsky.

Prototyping is everything because everything is a prototype.

“Every launch is effectively a prototype. No design is ever done,” said Khosla Ventures design partner, Irene Au, in a talk that held up a complex project with her residential architect as a model for all design collaborations.

Speaker Natasha Jen / Photo by Julian Mackler

Post less, critique more.

If Google Image search is your sole barometer, “design thinking uses just one tool: 3M Post-Its,” said Pentagram partner Natasha Jen. “Why did we end up with a single medium? Charles and Ray Eames worked in a complete lack of Post-It stickies. They learned by doing.” Jen lobbies for the “Crit” [criticism] over the “Post-It” when it comes to moving design forward.

Know your design ancestry.

Writer and Postlight founder Paul Ford spoke in exquisite, informed detail about the four user experiences that transformed his life: the Control Panel in Macintosh’s debut System, the Reveal Code mode in WordPerfect 5.1, layers in Photoshop 3.0, and the general dexterity of Netscape Navigator. He also gave a knowing nod to the favorite crutch of newbie designers: the drop-shadow.

He's not wrong… #99UConf http://pic.twitter.com/ZITLJzBkaQ

— Michelle Nickolaisen (@_ChelleShock) June 9, 2017

Friction builds character.

“What do we lose when we remove friction? When we remove all friction, we remove opportunities for serendipity, confrontation, and personal growth,” said Airbnb’s Steve Selzer.

Speaker Debbie Millman / Photo by Julian Mackler

You can’t disrupt the need for hard work.

“Anything worthwhile takes time,” said Design Matters’ Debbie Millman. “Anything worthwhile takes a lot of time.”

The most important user interface is between you and the gym.

“You can’t do good work if you’re not in good health,” said artist and designer James Victore. “I know too many people are basically killing themselves at work. We have to stay happy, healthy people.”

Create the conditions for creativity.

The right environment can make a huge difference in getting a budding idea off the ground, and Refinery29’s co-founder and executive creative director Piera Gelardi highlighted four ways to foster that creative state: know what works for you, laughter unlocks brilliance, do it for someone else, and embrace the uncomfortable.

Real-life prototype as much as possible.

Clients tend to connect and understand the idea you’re presenting to them much easier if they can see the solution, live in their hands, shared the team at Ustwo. It doesn’t have to be the completed output. Just enough for them to understand the route you’ve chosen.

Know the reality of ‘just-a-minute’ thinking.

On average we switch tasks every three minutes and five seconds, said Capes Coaching co-founder Betsy Capes,. “It’s not multi-tasking,” she noted. “It’s task overload. It takes 23 minutes and 15 seconds to get back to an interrupted task.”

This #99UConf studio session slide is on point… guilty as charged @CapesCoaching http://pic.twitter.com/eSqUSmL9ii

— Pollyanna Macchiano (@Poriiana) June 9, 2017

Sweat the right stuff.

Be mindful to sweat the right details and not all the details, when dealing with large projects or many iterations, noted Dropbox’s Aaron Robbs and Collin Whitehead.

Creativity is multi-dimensional.

“A greater knowledge of the materials you can use alters the way you design,” said Material ConneXion’s Dr. Andrew Dent, who works with clients from adidas to BMW on choosing the materials that go into their next best-selling sneaker or sedan.

Shake Shack does a killer lunch spread. 

I knew when I arrived at my @99u Conference session at @shakeshack that I had chosen wisely. #99uconf http://pic.twitter.com/wExCwpRtVy

— Petri Darby (@darbydarnit) June 10, 2017

Data isn’t just for data scientists.

“Everyone [on a team] can and should be involved in the data collection process” said Spotify’s user researcher Caitlin Tan.

Good work doesn’t need trust.

“‘Trust me, this is an amazing idea’ doesn’t exist anymore,” said Verdes partner Greg Matson. “Your idea needs to sell itself. It’s more show me than trust me.”

A delegate takes Google VR’s Tilt Brush experience for a spin / Photo by Julian Mackler

Dwell on the past.

“We believe in a ‘learning loop,'” said BuzzFeed senior producer Erin Phraner. “We loop back to successful videos to try and learn from it and to find new things we can test in the next video. It’s so important to us because it’s a great indicator of what is working.”

Attack your project from different perspectives.

“Sometimes designers needs to step back—be an art director or a production manager—to to find the most appropriate methods or design solutions for the problems. You don’t have to do everything yourself,” said MoMA associate creative director, Ingrid Chou.

Prototypes over presentations!

Prototypes Over Presentations: Fostering meaningful product strategy at our #99uconf Studio Session http://pic.twitter.com/cAUxPmnWjo

— Postlight (@PostlightStudio) June 9, 2017

Intercept your biases.

Why is it so hard to break down biases? Because it only takes 1/10 of a second for our brains to categorize someone by race and about 1.5/10 of a second by gender, said SYPartners managing creative director Rie Norregaard. To increase awareness of these biases and begin to advocate for change, Norregaard recommends creating a space with your team where it’s okay to talk through our biases. 

99U delegates get to work at a Studio Session / Photo by Julian Mackler

Round our your team by perspectives, not jobs.

When designing the dream team for a design sprint, the team at The Design Gym brings a variety of perspectives. What kind exactly? Here’s an easy way to think about it that cuts across industries: have a hustler, hipster, hacker, and heckler.

The Best is Yet to Come

99U has already set the dates for the 2018 conference, taking place May 9 – 11 in New York City. Tickets go on sale later this summer.

DJ Juan Maclean backed by Symmetry Labs’ Sugarcubes light installation at the 99U Closing Party / Photo by Julian Mackler

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