What It Takes to Turn a Hobby Into a Career at Age 40

At 51, Lisa Congdon is the picture of a thriving freelance artist.  Her client list includes Fortune 500 companies (Facebook, General Mills, Hewlett Packard), tech companies (Airbnb, Sonos), and art museums and universities (MoMA, Harvard), among many others. In addition to her commercial work, she makes, exhibits, and sells fine art, teaches online classes, and has published eight books, including the forthcoming: Find Your Artistic Voice: The Essential Guide to Working Your Creative Magic.

If you’d told her any of this in her early 30s, she would have laughed at you. Growing up, Congdon wasn’t even the creative one in her family (that would be her sister). After college, she went into education: first as an elementary school teacher and then as a staff member at a nonprofit working with public schools. Her life path seemed set.

But at 32, she experienced “a bit of a life crisis” after a long-term relationship with a woman she’d been dating since her early 20s imploded. In a depressive rut, she started seeing a therapist, who helped her begin the the terrifying process of figuring out who she was and what she wanted from life. Congdon didn’t have a lot of answers but, spurred by an unfamiliar urge to make things, she began taking community drawing and painting classes.

In the beginning, art was purely something she did for fun on the weekends. It stayed that way until, in the mid-2000s, she started a blog in which she posted pictures of her work. Congdon met other makers online, some of whom made their living from their art. It was a life she wanted for herself.

The transition wasn’t quick or easy. It wasn’t until 2011, at the age of 40, seven years after she began drawing, that she left her job to focus on her art career. “I did in phases,” she says, seizing opportunities as they came and slowly building up momentum and clients.

Here, Congdon looks back at her unconventional path to freelance success and why she’s glad she found art later in life.

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Q. When you started drawing and painting, you did it solely for fun. Looking back, did that mindset help you professionally?

A. To a certain extent, because I wasn’t thinking, ‘I need to make work that’s really conceptual, or totally unique, or groundbreaking.’ I just drew what was around me, and then tried to make it interesting in terms of color palette and how I was arranging and rendering things on the page. My own style developed out of that.

Part of the reason I’m able to make so much work is that I don’t have voices in my head necessarily telling me that this is right or wrong. I just kind of try things.

Lisa Congdon is known for her colorful, abstract designs.

Q. You also started in your early 30s. For creative industries, the perception often seems to be: if you haven’t established yourself in your 20s, the ship has probably sailed. Were there advantages to finding art later?

A. There are probably a lot of artists who are starting out who don’t necessarily have a strong set of interests yet because they are only 22. I’m not saying all 22-year-olds don’t have a developed sense of interests, but I think one advantage to starting later in life is that I knew who I was already. I understood what I was drawn to, and that really helped me not trip too much about the meaning of my work. I just started drawing the stuff I was interested in and I didn’t overthink it. It freed me a little bit.

“Just because someone else you admire has some amazing accomplishment doesn’t mean that your work has any less value, or that your path is any less significant.”

I also think that because I came at this at an older age, I have patience with the art-making and creative process that I wouldn’t necessarily have had when I was younger.  In order to get good at something you have to work at it. I had experienced that in other areas of my life, and that’s how I approached my art practice.

Q. How did the way you thought about your work and process change as people began to pay attention to it?

A. When I started out as an artist, I was really free because I didn’t have any expectations for myself, nor did anyone else. That definitely morphed into more self-judgement, or more, ‘am I doing this right?’

When I’m working, I try to stay focused on my own vision. I think so often now, what happens to people who are trying to make it in the art or illustration or design world is that we get overwhelmed by what other people are doing. You become part of this community of artists online or in your actual community where you live. You are inadvertently bombarded by their work; we all follow people we admire. But I understood early on that I had to tune that out. That I could admire those people and I even learn from them, but I needed to stay focused on my own vision of what I found interesting or beautiful or weird that I wanted to communicate in the work that I do.

Q. What are some of the strategies you’ve developed for finding inspiration without getting overwhelmed by the work of artists you admire?

A. There have been periods of time that I’ve had to unfollow people [on Instagram]. Not because I didn’t like their work, but because I liked their work—I was feeling a sense of competition or jealousy. I do it less and less because I feel more confident in my own career, but there was a time when I had to block out the stuff that didn’t make me feel good.

“Some things we think are going to be life-changing for us end up not being [that way], and other things that we never would have imagined are absolutely transformative.”

I also had to work on embracing this idea that there is room for everyone. Just because someone else you admire has some amazing accomplishment doesn’t mean that your work has any less value, or that your path is any less significant. It’s a really important mindset, and I had to work really hard to get there.

More of Congdon’s artwork.

Q. What has your career taught you about the importance of professional benchmarks?

A. You think, ‘Oh, if I only had this client on my client list, I will have arrived.’ I just announced that I did a collaboration with [fashion brand] Commes des Garcons. Everyone is like, ‘That’s amazing!’ But is my life or my illustration process any better because I’ve had this giant client? No, not really. You learn over time, even when you get these great client jobs, that a) sometimes they are hard work and b) they don’t necessarily make you a happier person or make your career any more or less significant.

The more you do something that you want to do in your life, the more you have perspective about it’s true meaning. Some things we think are going to be life-changing for us end up not being [that way], and other things that we never would have imagined are absolutely transformative. I never imagined that all the personal work I do would have lead to the more gratifying projects that I’ve done in my career. In the beginning, I was like, ‘I want to build this cool client list and do cool projects with clients.’ I’ve done that, and while a lot of it has been really fun, it’s not necessarily where I’ve gotten the most satisfaction and meaning.

Q. You kept your full-time job for years after you started selling your art. Is this a path you recommend for other people who are hoping to break into a creative industry?

A. Definitely. The minute you put all of the pressure on your art career to feed you is the minute it becomes extremely stressful. I talk to people all the time who have part-time jobs either as illustrators or artists who work for bigger companies or as a barista or a social worker because they don’t want that pressure. It allows them to take jobs that they want because they want them, not because they have to have them.

“We have this image of the successful entrepreneur or the successful artist as someone who makes their full-time living doing it, who is thriving and gets all this work. There isn’t one way to be an artist; there isn’t one way to be an entrepreneur.”

If you already have a bunch of work coming your way and you have [multiple] income streams, then quitting your job is fine—do it! But there is this period of time where you need to do three or four different things.

Q. It can sometimes feel like the ultimate goal for any aspiring creative is to do what you’ve done: develop your art career to the point where it sustains you financially. Is that the only option, or can keeping a part-time job work in the long-term?

A. I have a lot of friends who do that to this day. That’s their comfort level. We have this image of the successful entrepreneur or the successful artist as someone who makes their full-time living doing it, who is thriving and gets all this work. There isn’t one way to be an artist; there isn’t one way to be an entrepreneur. There are lots of ways to do it, and to do it well, and to live a happy life, because ultimately that’s the goal. The goal isn’t to have a successful career. The goal is to be happy.

 

 

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The One-Word Question That Never Goes Out of Style

When we set the theme for our 2019 conference — The Creative Future — we imagined a future where creative skills are more pervasive and prized, and how that might reshape the world around us. As we prepare for the event in May, we’re asking our speakers to share a skill they think is important for all creatives to navigate what’s to come.

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For Thaniya Keereepart, head of product experience at crowdfunding platform Patreon, asking “why?” is a timeless skill with huge payoff. Thaniya will be at the 11th Annual 99U Conference taking place May 8-10 in New York City.

Q. What’s a skill or characteristic you’ve cultivated in your career that you find to be futureproof?

A. Curiosity. I ask a lot of “why” questions. I love to get to the bottom of things—to understand what motivates us. Why we come to believe something. Why we choose what we choose. Why some people see the world differently. A big part of what I do is read people’s reaction to these “why” questions. Not just what they say, what they click on, or what they look at, but why. Through listening and observing their articulation, I am able to understand intention more deeply. It makes me feel more connected and more empathic, personally and professionally.

Q. Why will it be so important in the future?

A. We are consumers of information. Algorithms spoon-feed us with the next thing we should read, watch, or listen, where we should spend our time. Someone (a curator, taxonomist, etc.) or something (a machine learning algorithm) is deciding all of this for us. Our worldview gets shaped by what we’re exposed to. If we don’t take a moment to ask ourselves why our attention is spent on something, we stop challenging our own cognition. When we stop challenging our cognition, we starve ourselves of perspective, imagination, and ultimately, empathy.

Q. What’s a time in your career that you’ve seen that skill or characteristic at play in a way that made you realize its power?

A. Last year we received a request from one of our creators to fix our group messaging bug. It was more or less a typical request coming in through our logging channels. When you spend enough years working on consumer-facing products, you have to learn what’s critical vs what’s “nice to have” and prioritize the team’s focus accordingly.  

I took time to get on a call with this creator to talk through why this bug was important to her. She shared with me that the bug caused her to miss a few deliveries to her customers, but our system didn’t warn her and so she didn’t know. As a result she began receiving hate messages from her customers which escalated quickly into death threats. She creates art for the 18+ space. In this space, online bullying can get very scary very quickly. She had lost a few customers along the way, which affected her ability to make enough money to pay her rent on time. But more than that, she got scared.

A to-do ticket is a ticket. We can quite quickly forget the livelihood of folks using our products sometimes when don’t spend time asking why.

Q. What advice would you give to anyone looking to cultivate that skill or characteristic?

A. I’d start with something more casual and fun. When you come across a conversation that sparks your curiosity with friends, try asking why five times. See where your conversation leads. See if you can get to their intention. At work, when you come across differences in opinion and you’re needing to justify your decision, try writing down why you decided on whatever. Trace it back five times. You’ll learn so much about yourself and you’ll be more prepared for the future.

Hear from Thaniya and other creatives shaping the future at the 11th Annual 99U Conference, May 8-10, 2019 in New York City.

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What Creative Visionaries Do That Most People Overlook

“You keep using that word. I do not think it means what you think it means.”

So spoke the character Inigo Montoya in The Princess Bride. While Montoya was referring to the word “inconceivable,” he may as well have added another word to the list: “visionary.”

As a society, we adore creative visionaries. We follow them on social media, praise them in blog posts, and eagerly listen to them on podcasts. In this influencer-obsessed era, we’ve reached Peak Visionary, creating idols out of people whom we believe can see the future. .

But that’s where we’re wrong. Visionaries don’t see the future; their magic is that they’re able to see the present while the rest of us are busy looking at the past.

While researching for my book, Break the Wheel, I stumbled on a psychological issue which causes most of us to base our thinking on the past instead of the present. It’s called “cultural fluency,” which is your behavior when the world unfolds as expected, based on past precedent. When someone shrugs and explains, “That’s just how we do things around here,” they’ve fallen victim to this form of mindless decision-making triggered by cultural fluency.

On the other hand, those “visionaries” we admire are more willing to question conventional wisdom. They understand that best practices are lagging indicators, and so they ask, “What if we made decisions based on leading indicators instead?”

Sure, an innovative thinker can more easily extrapolate their ideas from today into the future, but it’s only because they start by understanding the present so intimately. Like building a skyscraper, their foundation is strong enough to support the heights they reach. Meanwhile, we’re too reliant on details pulled from a bygone moment instead of updating our knowledge using our present context.

“Despite how innovative a supposed ‘visionary’ seems, we need to embrace the truth: Innovation requires clarity, not prescience.”

We often learn of great artists, builders, and scientists who were rejected by their peers only to be revered today. We conclude, “They were ahead of their time.” But consider that their contemporaries were merely stuck in the past. History shows us that it might take decades, even centuries, for people to look back and say to themselves “Ya know, that fella was really onto something. Maybe that whole ‘clasp him in chains’ thing wasn’t the best move.”

Weren’t people from olden times so silly? Yes. But we’ve only gotten goofier today. It’s easier than ever to base our decisions on the past thanks to the endless amounts of supposed “right answers” shared publicly online. In the end, we need to set that information aside—if only for a moment—to inform our decisions using the present. Despite how innovative a supposed “visionary” seems, we need to embrace the truth: Innovation requires clarity, not prescience.

There’s an old quote often attributed to the great investor Charlie Munger of Berkshire Hathaway fame, which he borrowed from the British economist John Maynard Keynes: “I’d rather be vaguely right than precisely wrong.” This idea is simple to understand but hard to execute: it’s more effective to continually update your knowledge rather than profess to know “the” answer all the time. When you routinely course-correct as you acquire new information, you shape your thinking and thus your work to the present moment. Whereas best practices provide security in their absoluteness, it’s dangerous to base a decision on something that precise. Any mandate or blueprint must be contextualized to your unique and present situation to be as relevant and effective as possible.

“Visionaries aren’t more creative than us. They’re more mindful. “

As Keynes first suggested, we should embrace a more zig-zaggy truth than best practices offer: To succeed in the real world is to admit that the world changes, every day, all the time, and thus we should act like lifelong learners. If we adopt this idea of being “vaguely right” instead of “precisely wrong,” just as Munger later did, we might see visionaries for what they truly are: Investigators. They regularly update their knowledge as the context changes. In this way, I suppose they do possess a kind of “vision,” but it’s not the kind we usually imagine. It’s not foresight at all. It’s the ability to see the world around them more clearly. What if we did too?

I’ve written before on this very site about how to do exactly that. Today, I’d challenge each of us to rethink the absolutism proliferating around the business world. That glut of prescriptions has turned all those “how-tos” into “have-tos,” but the only thing we have to do is find the right approach for our current and unique situation. Visionaries are investigators, not experts. That’s not a gift they were given. It’s a skill each of us can hone.

Seeing the world as it really is—today, right now—can help us make better decisions in our work. It can snap us out of cultural fluency, that tendency to lapse into stale patterns because “that’s how we do things around here.” Visionaries aren’t more creative than us. They’re more mindful. They’re more focused on developing the self-awareness and situational awareness they need to see the world as it really is—then act accordingly.

My challenge to you: Let everybody else place visionaries on a pedestal. Let them agonize over understanding their “secrets” and how they peer into the future. The next time you start assuming that those people see something you can’t, I hope you’ll smile and shake your head. Because it’s inconceivable.

“Visionary.” Ugh. You keep using that word. I do not think it means what you think it means.

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How This Underrated Skill Can Help You Thrive in the Future

When we set the theme for our 2019 conference — The Creative Future — we imagined a future where creative skills are more pervasive and prized, and how that might reshape the world around us. As we prepare for the event in May, we’re asking our speakers to share a skill they think is important for all creatives to navigate what’s to come.

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In these fast-moving times, Jamal Dauda, global head of music at WeTransfer, says it’s more important than ever to sharpen your listening skills. Jamal will be speaking at the 11th Annual 99U Conference, taking place May 8-10 in New York City.

Q. What’s a skill or characteristic you’ve cultivated in your career that you find to be futureproof?

A. Empathy. It might sound a bit airy, but taking the time and energy to truly cultivate understanding amongst colleagues and creative partners creates an environment where the best ideas can find life.

Q. Why will it be so important in the future?

A. There are a lot of sections of culture and society that feel more segmented than ever. We now live in a time where there is an endless number of micro-communities that have unique tastes across music, film, art, and other media and are able to digitally congregate. As time marches on, creators are being asked to tap into and authentically speak to a more diverse group of people and the only way to do that is by actively listening and consciously incorporating the input, feedback, and belief systems of the people you are hoping to connect with. The best parts of our civilization have always thrived in the light of shared understanding and I don’t foresee this changing soon.

“Being quiet and being present are often mistaken for being the same thing.”

Q. What’s a time in your career that you’ve seen that skill or characteristic at play in a way that made you realize its power? Please describe the event, and what you thought to yourself at that time.

A. It’s something that happens on a reoccurring basis. A large percentage of my job is talking to and coordinating with people tasked as representatives of the artist: managers, record labels, creative directors, etc. However, I find that my best work has always come from direct contact with artists or creatives in a space where they have the freedom to convey their thoughts and goals in an unfiltered way. There is a real magic that comes from just being able to listen and absorb pure creativity at the source. It often changes and reshapes all parties involved for the better and I find that to be an understated, yet very powerful experience.

Q. What advice would you give to anyone looking to cultivate that skill or characteristic?

A. Ernest Hemingway really had the best advice on this. He said, “When people talk, listen completely. Most people never listen.” It really does put you in a hugely advantageous position to listen more than you talk. Being quiet and being present are often mistaken for being the same thing.

Hear from Jamal and other creatives shaping the future at the 11th Annual 99U Conference, May 8-10, 2019 in New York City.

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5 Rituals for More Productive, Creative, and Resilient Teams

Teams have life cycles: they are born with a mission, they grow and sustain themselves, and they dissolve as their mission ends.

But not all of these cycles are happy. Teams go through fights. They get “re-org”-ed and end up with new leaders or changed missions. People get fired or quit.

One of the ways to make these transitions easier is through rituals, deliberate actions that bring higher meaning into an experience. Often thought of in a religious or spiritual context, rituals can be any series of activities that helps connect people to something bigger than what’s directly in front of them. In our work on ritual design and teachings at Stanford’s d.school, my partner Margaret Hagan and I found that rituals can give a safe space for individuals and teams to experiment with new ideas while reinforcing values and connection despite cycles of change.

Rituals, of course, can come in many forms. In researching for my book, Rituals For Work, I’ve seen many that can help teams become more creative, productive, and adaptable. Some of the most common ones are daily scrums, weekly share-outs, and team-bonding events such as shared lunches and retreats. Here are five other rituals that managers and individual contributors can employ for healthier, more adaptable teams. 

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1. For improving performance

Research shows that rituals help people regulate their emotions, get closer to their life and professional goals, and live by their values. Emotion regulation is a fascinating aspect of rituals. For instance, athletes such as tennis player Rafael Nadal use rituals to calm and focus on the game. Teams like New Zealand’s rugby teams, on the other hand, use a dance ritual called Haka to amp up the team’s emotions for confidence.

In our research, we came across the “Moment of Reverence,”a small ritual to do right before a big event. It’s taken from the operating room, where doctors and nurses, right before they begin a surgery, intentionally stop and take a moment to remind themselves that the surgery they’re about to perform is on a real person, who has family and friends and a whole life to live. It’s a moment to reflect on how important the surgery is for this person. This small moment of reverence is a way to stop from getting burned out or empathy fatigue. It’s a way to ensure that the team is also tuned in, and performing with flow.

You can see effective use of this ritual in high-stakes business situations. Often times, in the grind of production, teams might lose touch with people on the receiving end of an offering. To avoid this, teams can take a Moment of Reverence to remember the end user that they are serving before launching a new product or initiative. By taking that moment to connect, it’s a way of gut-checking yourself that the work you’ve done is sound.

2. For creating a deeper sense of purpose

What makes a team a healthy one is connectedness and a sense of belongingness among its members. When it’s attuned to its members’ values, community rituals help a manager create a whole which is bigger than the sum of its parts.

The pinning ceremony from Stanford d.school is a good example for community building. It is a special ritual when a team has really come together and achieved something. When students are at the end of a class, at the very final moments of the final class, the teaching team leads a pinning ceremony of all the students. They pass around a box where there are five different pins, each with a different symbol of the school. Each student gets to choose a pin, with the symbol that they prefer. Then, the teaching team leads the students in saying a final script that recognizes that everyone is now part of the d.school community and that they have completed this class. Ritual finishes with pairs pinning each other.

You can adapt this ritual for the business world in multiple ways. One example could be when employees upskill their work profile with new roles such as data scientist, or design thinker, they need ways to feel accomplishment and a sense of new identity. At the end of their training, a similar pinning ritual can reinforce their identity and help them build their new role. This can also be applied when you form new teams and in need of a shared identity and purpose. The chosen symbol for pinning can crystallize the identity of the team.

3. For navigating transitions

When an employee starts off new position anxiety is there, or your team experiences a re-org followed by layoffs/firings, fear among the team members is paramount. To ease these kinds of transitions is possible with rituals. Ritual lens brings the acceptance of the emotional overload & awareness of the situation. It then creates a safe space to embrace it, even express it.

To give an example, our students created “Crash the Desk,” which focuses on onboarding an employee. Crash the Desk, is to welcome new hires with a surprise treasure hunt. When the employee is distracted away from the desk, their team-mates fill up their sad, empty new desk with personal objects. Then the employee must go on a hunt, talking to all their new co-workers to try to find the objects’ owners, and hearing stories about why they’re special.

4. For getting through conflict

When a conflict happens between team members, there are several ways to handle it, including ignoring it, going nuclear about it, or mitigating it. The last option is often the hardest one, however, once it’s handled with care, it can help a team bounce back, and even get better than before the conflict. That’s where rituals come into play again.

A conflict ritual fits mitigation scenario and utilizes the safe space quality of rituals. Such a ritual usually starts with reflection and continues with letting-go-of-negative-emotions, ending part might be a refresher for a new start, or more utilitarian and focuses on problem-solving. Depending on the team dynamics, a neutral outside facilitator can help run such a ritual for the team.

“Burn the Argument” is a conflict ritual, to deal with a fight that might have broken out on your team or in a meeting. It comes from one of our designer friends. She was addressing difficult emotions that emerged after a conflict between team members. A few days later, a manager ran this ritual with them, to help them move past the bitter feelings and also get the rest of the team back on track. Like the title says, it involves writing down the argument and feelings about it on pieces of paper, then tearing it up, and as a team, bringing it together. It’s a small symbolic act, but an explicit way to call out that conflict happened and that the team is deciding to move past it while still recognizing the emotions at stake.

5. For boosting creativity

Rituals are already woven into the fabric of peer-to-peer and peer-to-team relationships. However, to continue to grow, a team has to go beyond the usual, and get creative in its own capacity. Creativity rituals come into play for that purpose. In our work, we’ve found creativity particularly challenging as the concept often comes with a baggage of pre-conceived notions of creativity. Creativity is almost a taboo among engineering or bureaucracy-heavy cultures. You can introduce rituals into the existing routines as a way to infuse creativity.  

“The Daily Drawing” is a small and easy creative ritual, that comes from designer Ayse Birsel. She starts each day by giving herself a short amount of time to do any kind of drawing at all, as long as the pen is moving across the page. The goal is to wake the brain up, but not to think too much, and not to let the blank page intimidate you. By having this little ritual of just doing any kind of drawing at all, you get yourself into a creative flow and stop all the anxieties from blocking you.

 

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The Joyful, Messy, Sometimes Lonely Uncertainty of Pursuing a Creative Life

Career paths are rarely linear. Many of us are unable to accurately chart out where we will end up professionally years, much less decades, out.

In some respects, Julia Bainbridge’s course has been straighter than most. A freelance journalist, podcast host, and author of an upcoming book on non-alcoholic cocktails, she’s been interested in writing and telling other people’s stories from a young age. She wrote for the school paper in college, and one of her first jobs out of school was in journalism. Since then, she’s worked for national outlets including Food & Wine, Bon Appetit, and, most recently, Atlanta Magazine, where she was the food editor.

But beneath this curated trajectory lies twists and unconventional turns. Bainbridge started in food journalism, but her interests have since expanded to include human connection and loneliness—she started a podcast exploring these topics in 2016—and her own shifting relationship to alcohol, which helped land her a book deal last year.

With more than two decades of experience as a professional writer and a bevy of interests and ongoing projects, Bainbridge is at a crossroads: she’s not sure where her writing or life will take her after the book comes out, which is exhilarating on good days and terrifying on bad ones.

Here, Bainbridge reflects on a lifetime of pursuing evolving interests, the solitude (and sometimes loneliness) of freelance life, and why creative uncertainty can be a blessing and a burden.

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Q. How did you first get interested in food writing?

A. When I first realized food is one lens through which we can study people. As an anthropology major in college, I learned there was this academic side of food writing and authors who were looking at other cultures through food: what they eat, what they don’t eat, and I found that connection between cooking and identity fascinating. I said, ok! I can combine with the interest in food and studying people and go work for a food magazine.

Q. Which you did, first at Food & Wine, and then stints at Yahoo, Bon Appetit, and Atlanta Magazine. But in 2016, you started The Lonely Hour, a podcast about loneliness and solitude. What drew you to the topic?

A. Food and dining is really about connection. Loneliness is the other side of that. It’s an area I think about a lot: connection and the lack of it. At the time I was 33, living in New York, looking for partnership and not finding it. The video-gamification and commodification of dating people through apps made modern romance seem pretty bleak. Was I going to be alone forever? It’s certainly not the sad single girl show, but my personal interest combined with reports detailing increasing social isolation. I was observing the ways in which technology is distancing us from one another. I saw more and more people freelancing and otherwise working alone. I learned that more people are living alone and aging alone. I wanted to explore what all of that looked like.

“There is a distinction between aloneness and loneliness. Aloneness is a state; loneliness is a sad feeling about that state.”

I’ve always been acutely aware of how imperfect we are. How hard it is for humans to connect, and feel sated by that connection. We all struggle with personal demons that prevent us from being honest, from being ourselves, for asking for love and then, if we get it, feeling truly worthy of it. It’s why I talk about loneliness the way I do on the show: This is part of the human condition. It’s something we all deal with. It’s a simple message but one we seem to need to hear over and over again.

Q. How does solitude and loneliness inform your creative process?

A. I am my most creative in moments when I am alone—when I’m on a quiet walk, not listening to anything on my iPod. That’s when I come up with ideas. I want to underscore how important this time is for us all. We are constantly entertained today. If there is a void, we are taught to fill it. We have these technologies that are so good, that we’ve just gone with them. I wonder what we’ve lost, and what we want to recover.

There is a distinction between aloneness and loneliness. Aloneness is a state; loneliness is a sad feeling about that state. I do think loneliness can be a rich place from which to write, like any of our dark places can be rich places from which to write. But it can also impede creative work. Sometimes if I am lonely and depressed, I will shut down and isolate and not want to do anything. I just want to numb out. It’s where drinking was helpful and it’s also where shitty reality TV is helpful. So it can also impede work, and it can impede my social life.

It’s a balancing act. I need a significant amount of alone time, but I also need to be around people. I am a social person—we are all social creatures.

“It’s unfortunate that alcohol does such a great job at quelling anxiety, in the moment at least.”

Q. You’re working on a book that includes recipes for non-alcoholic cocktails. Alcohol and creativity are often linked—was that the case for you, and how has your relationship to alcohol evolved over the years?

A. It’s unfortunate that alcohol does such a great job at quelling anxiety, in the moment at least. (Laughs.) It’s helped me be free and loose on the page, and loose and free with people. I have a complicated relationship with alcohol that I’m still figuring out, and while I do so, I’ve removed it from my life. I’m not always successful at keeping it there—I have slipped—but I am committed to trying. For now, I am a happier and sharper person, and a better friend and colleague when I am sober.

Q. You recently moved from Atlanta back to New York to write your book and work on your podcast. What was behind that decision?

A. I am in a place right now where I’ve burned it all down and I’m finding out who I am now, and what I care about. I left my full-time job as an editor to focus on these projects that mean something more to me. It was a risk; New York is expensive. But returning also meant being around my people who remind me of who I am. Sometimes other people can know us better than ourselves, or reflect us back to in a way that is clearer. New York is a grind and a hustle and you have to push, but it’s also my home. It’s where all my people are, some of whom I’ve known since I was five years old, who love me warts and all.

This interview has been edited for clarity and length.

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To Survive the Future, Get in Touch With Your Inner Child

When we set the theme for our 2019 conference — The Creative Future — we imagined a future where creative skills are more pervasive and prized, and how that might reshape the world around us. As we prepare for the event in May, we’re asking our speakers to share a skill they think is important for all creatives to navigate what’s to come.

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After a 25-year career at Disney that included a role as head of innovation and creativity, Duncan Wardle now spends his time coaching companies on how to increase their capacity for creativity. Duncan will be at the 11th Annual 99U Conference taking place May 8-10 in New York City.

Q. What’s a skill or characteristic you’ve cultivated in your career that you find to be futureproof?

A. This one’s easy—the ability to draw on the traits we are all born with. It sounds simple, but it’s true. We are all born creative (remember how, as a kid, you’d play with that box your birthday gift came in?). We all have an amazing imagination (remember that crazy dream you had last week?). We were all curious once (you may not remember, but you probably spent your childhood asking “Why, why, why?”). And we are all naturally intuitive (like it or not, we make most of our decisions as consumers by going with our gut). These are the skills that will continue to push you forward in the future.

Q. Why will these skills be so important in the future?

A. Because they are the four skill sets that cannot be replicated by artificial intelligence. You cannot program creativity; you can tell the robot what to paint and it will create a masterpiece, but only once programmed. You can’t program imagination or curiosity, and you certainly can’t program intuition, so simply by dialing up the skills we are all born with we can become far more useful in an era where most skill sets will give way to AI.

Q. What’s a time in your career that you’ve seen these skills at play in a way that made you realize their power? Please describe the event, and what you thought to yourself at that time.

A. I believe that some of the most creative ideas are often the simplest. One example that comes to mind is when we were launching our Twitter account at Disney and I blurted out, “Let’s do it with 140 characters.” Everyone was like, “Duh?” No one realized what I had actually proposed—launching with 140 actual Disney characters! So we did it. We lined 140 Disney characters to form a gigantic hashtag and took a photo from a crane. It was a simple idea that came from a place of play. The image went viral very quickly.

Wardle believes that simple ideas can be powerful. Case in point, the 140-character hashtag he helped put together for Disney. Photo courtesy of Disney.

Q. What advice would you give to anyone looking to cultivate these skills?

A. Be playful when you are looking for that big idea. For many of us, our best ideas come to us when we’re in the shower, when we’re jogging, when we’re on the train—in other words, when we’re anywhere but at work. Why? Because we can only access our subconscious brain when we are relaxed. When we’re stressed, all that stimulus back there is waiting to connect the dots with the challenge in front of us, but it’s off limits. So what does that mean, in practical terms? If you’re holding an ideation session, run an energizer—an activity that gets people thinking and moving and interacting. You’re only listening for laughter; once you have that, it’s a sign that everyone in the room now has access to their subconscious brain. Alternatively, you can do what many great innovators did such as Walt Disney and Steve Jobs: go for a walk!

Hear from Duncan and other creatives shaping the future at the 11th Annual 99U Conference, May 8-10, 2019 in New York City.

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How Do You Find Clients? Designers Share Their Best Advice

There’s never been a better time for enterprising creatives to turn their passions and side hustles into a career. This is especially true for would-be graphic designers, as new and intuitive software becomes commonplace and the ability to share work with your network via social media have made marketing a portfolio as easy as pushing a button.

But as the field becomes more accessible, how do individual designers and firms get their work seen and, more importantly, commissioned, at a time when freelance marketplaces such as Upwork, Fiverr and 99Designs have thousands of designers competing for work? We reached out a handful of entrepreneurial graphic designers to learn how they command attention and snag clients.

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1. Be shameless about outreach.
Tala Safié, whose clients include AIGA Eye on Design and The New York Times

“When I was living in Beirut the design scene was relatively small, so I would often get clients through word of mouth and friends of friends. This wasn’t the case when I moved to the US. It was obviously harder for me to attract clients as I didn’t know anyone, so I had to do what every designer dreads doing—updating my (then expired) website and putting a proper online portfolio together. I also tried posting more of my work on Instagram (and fewer pictures of my roommate’s dog), but that didn’t last. What actually helped was shamelessly emailing people I was interested in working with directly, asking to meet or grab a cup of coffee. This is how I started working with Eye on Design. It gets easier—one job often leads to another. My advice would be to reach out directly to people you’d like to work with and see what happens. Care about the work that you do but, at the same time, don’t take your designer-self too seriously. And don’t be shy about money.”

 

2. Do what the apps cannot.
Louis de Villiers, whose clients include Nike, AT&T, and the Brooklyn Nets

“When I first moved to New York, work came slowly and it was difficult, but the longer I was here, and the more I worked at agencies and with clients, the wider my network grew. The opportunities began to flow in. Professionals move around a lot, so if you can show people you’re a solid worker and not a total jerk, you can be sure your name will come up wherever they go.

“Selling clever design, nuanced thinking, and positive human experience—that becomes a freelancer’s greatest assets. We like to think we (graphic designers) are unique, but similar crowdsourcing trends are happening across the board, with apps and companies offering cheap-to-free alternatives for everything from guided meditation to dubious medical diagnosis. Consumers are accustomed to cost-efficient options, but the reality is that these alternatives only provide for fundamental, rudimentary needs—Band-Aid solutions, you could say. The adage says ‘You get what you pay for,’ and that’s absolutely true.”

 

3. Put a zany idea out into the universe.
Pinar Demirdag of Pinar&Viola, whose clients include IKEA, Google, MTV, and Adidas

“Highlight your uniqueness—this is the only answer. Digital design is fun, quick, requires no investment. It is a volatile medium which takes no space, meaning it’s the top profession of our times—everyone who can use a computer and has an eye for aesthetics can claim to be a designer. We had a mad dream: in a sea of countless designers, in the age of easy access to design tools, we would go against the current and work as an image experimentation lab, favoring quality over quantity, decoration over pragmatism and wisdom over false advertising. We started launching image collections with themes from the zeitgeist and aesthetics from the future, with the idea that these cutting-edge experiments would attract us the best clients, brands, and companies in the top echelon of their practice. Without realizing, it turned out to be the best business plan.”

 

4. Don’t overlook the power of stickers.
Kenzo Minami, whose clients include Mercedes-Benz, Microsoft, Kidrobot, Raf Simons, VH1, Ace Hotel

“I think the most effective tool for promotion, and to connect with clients, might be shifting back to physical and analog promotional items, like stickers, posters, stationery, as well as your physical self—just showing up. You also cannot underestimate the power of social media. When everyone is connected, and we all equally have a medium to express ourselves and release our work, it’s easy to imagine that the media is oversaturated and everyone is numb to “just another piece of cool artwork,” but we are circling back to creativity outside traditional media and guerrilla promotional methods. Unless you are very skillful and nuanced, or have already built your name, you need the combination of both worlds—digital social network as well as the physical and real world.

“In the beginning of my career, when I was in the broadcast design business and the type of work I was involved in was becoming less creatively satisfying, out of frustration and to keep my sanity, I stayed at the studio for extra hours to do my own thing. This was before social media, so everything I was making stayed inside of my cubicle. One day, I made my first sticker, just for fun. This sticker eventually made it to Portland—my roommate at the time was in a band, and when she went on tour she took some with her—which ended up in the hands of Matt Clark and Alex Calderwood, who had just opened the first Ace Hotel and were also part of Neverstop, which was handling Nike projects. They saw the sticker, and contacted me and asked if I would paint the 50-foot mural for the new Nike Art Space they were opening in SoHo. This kickstarted my solo career, and taught me not to underestimate the small things we make.”

 

5. Take a Swiss Army knife approach to services.
Rachael Yaeger of Human NYC, whose clients include Flour Shop and Saturdays NYC

“I didn’t know it at the start of my career, but over time I developed a keen sense of seeing and understanding how the many moving parts need to come together to make for a successful project or product. I fell into what would now be described as product management, mixed with production, all with my own creative and curated lens. Today, Human NYC’s services range from research, positioning, strategy, naming, branding, art direction, content creation (photo, video, copy), packaging to digital design and development. We have a holistic understanding of our clients’ needs.

“At the end of the day, most of our work comes via word of mouth. After we work with a client, people essentially ask them who worked on their site, and we’re referred. Word of mouth is the luckiest position to be in since it establishes a ground level of trust. It’s like being set up on a date by mutual friends—there has to be some reason we were paired up!”

 

6. Develop a strong social media presence.
Melissa Gutierrez, whose clients include Univision and the ACLU of Florida

“As a designer, I find that sharing your work publicly is a very important part of the design process. It’s not the easiest thing to do, but it’s been incredibly helpful so far.

“Overcoming the anxiety that comes with vulnerability has allowed me to build networks, gather feedback, and feel connected to both designers and viewers alike. Sharing my work also helped remind me that the design process is iterative, so there’s always room to improve or modify a project. I’ve been asked to work on several projects because someone happened to see my work on social media. There are a lot of designers out there, but staying true to your style will drive opportunities your way and serve as an advantage that allows you to pave your own path.”

 

7. Take the ‘one-off’ gig.
Amy Globus and John Clark of Team, whose clients include Red Bull Arts and Marlborough Contemporary

“Most of our extensive client relationships were born out of personal relationships or small “one-off” design gigs. Taking on a design project for a friend or colleague can come back as a large corporate brand project in a short matter of years as friends rise in the ranks along with their career paths and move around to different companies, they put us forward with the strong recommendation because they have been through it with us before and trust the relationship.

“Partnering with other agencies with adjacent skill sets has also been a successful ‘feeder’ for our business. Later, when we engage in a project with a new or existing client who needs a strategic setup to ground our design work, we recommend that partner to lead the charge.

“As for Upwork, Fiverr, 99Designs, Canva, Squarespace, etc, we genuinely don’t view those platforms as competitors. Individuals and business owners considering those solutions are after the cheapest and fastest solutions. And that’s okay—sometimes it’s the right solution for the task at hand. We work with clients who value our expertise and guidance. We are constantly helping our clients figure out something that they can’t figure out on their own and as of yet, we haven’t been up against an online platform that can offer that.”

 

8. Keep evolving (like Madonna).
Emily Suber, whose clients include Netflix and AMC Networks/IFC

“My clients have always come through word of mouth. I do a lot of networking (mostly through friends) and I have found that it has just worked for me. Also, most of my clients are in film, so it’s a more defined group with defined needs. I should probably post more on Instagram, but because of proprietary issues, I can’t usually show anything until it’s been released in the traditional entertainment sense (released in theatres, Netflix, etc).

“Has it gotten harder to be a creative professional? I think it depends on your particular field—I know my friends in editorial design have taken a hit. My graphic design career has evolved from publishing/print to interactive to film design/motion graphics. If anything, I feel like I am living my best life in a field that I adore. It’s all about evolving, Madonna-style, throughout the ages. If something doesn’t work, either emotionally or financially, you have to search for that next step. Although it can be lonely, you will eventually end up on the right path. Talk to people from all walks of life—you wouldn’t believe the advice you can get. Join as many design networking groups as you can (I currently bounce around 3 or 4). Don’t worry about what other people think of you because they probably aren’t thinking about you. Rejection and perseverance are essential, aim to hear “no” once a day. Find your support system and keep them close.”

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How Deep Listening Can Help You Be More Creative

When we set the theme for our 2019 conference — The Creative Future — we imagined a future where creative skills are more pervasive and prized, and how that might reshape the world around us. As we prepare for the event in May, we’re asking our speakers to share a skill they think is important for all creatives to navigate what’s to come.

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Jessica Orkin is the President of SYPartners, a consultancy that helps organizations transform into more vibrant versions of themselves. Jessica will be at the 11th Annual 99U Conference taking place May 8-10 in New York City.

Q. What is a skill you believe to be futureproof?

A. To navigate the edge of the unknown, both with Fortune 500 companies and with my SYPartners team, I have cultivated a practice of deep listening—an intentional quieting of the ego and the desire to apply past patterns or jump to solutions. The result is an openness to a much richer, less obvious world of information: the energy of a room, the connections between people, the things unsaid, the voices missing in a conversation, ideas that jolt and jar rather than fit in. From that place of deep listening, I start to sense what lies beneath the surface of things, and often a different understanding of the “problem” emerges, giving rise to radically different ways forward.

Q. Why will deep listening be so important in the future?

A. Design thinking has inspired many people, particularly those who don’t self-conceive as “creatives,” to recognize their creativity and generate ideas at high volume and velocity. I think of this as the “creative exhale”—emitting ideas into the world. But as more interconnected, complex human challenges and opportunities emerge we will all need to get better at the “creative inhale”—attending to the information we take in, the signals of the future we are sensing, the voices and perspectives that may be missing, and how we define the problems we solve. Listening deeply and differently changes our creative exhale, enabling us to generate fundamentally new solutions.

Q. Has there been a time in your career when you saw the power of the creative inhale?

A. In my work with companies, I’ve seen inspiration happen when leaders seek out new perspectives and focus on their creative inhale before jumping into the exhale.

For instance: What does a luxe Danny Meyer restaurant and your local CVS have in common?

They are both pursuing purpose-driven service and hospitality. CVS executives saw this firsthand on a recent visit to Manhattan. SYPartners had organized a tour of hospitality experiences to inspire new thinking about customer-centricity. It would have been easy for the pharmacy leaders to dismiss the restaurant’s extra-mile hospitality as irrelevant to CVS. But they didn’t. By leading with curiosity and suspending skepticism—in other words, practicing deep listening—they came away with insights that are changing how they think about their culture, not just their approach to service.

Q. How do you get better at deep listening?

A. I took a fairly radical approach—three years ago, I became a student of sound meditation with Sara Auster to learn about the science and practice of deep listening. This led to some wild adventures (ask me about studying raga in India for 10 hours a day, with no musical background). This path is decidedly not for everyone. Some easier ways in:

1. Pursue curiosity. Ivy Ross, head of design for Google Hardware, once told me, “I pay attention to what gets my attention.” That awareness has taken her on intellectual and creative adventures that led to new products and paradigms.
2. In the beginning of a new project, cultivate the art of the beautiful question. Observe how leading with questions instead of answers changes your understanding of the problem you are seeking to solve.
3. Wake up your senses. Move your body, go to a museum, attend a sound bath. Do anything that gets you out of your head for a while and activates all the other ways you take in information.
4. Meditate. If nothing else, it will quiet your ego and help you hear others in ways that creates room for new possibilities to emerge. I recently meditated for 20 minutes in a hallway before going in to meet with former President Obama, so I could listen as deeply as possible instead of trying to get my point across or, worse, trying to impress. It worked. Mostly.
5. When creating, be aware of the mode you are in—inhale or exhale. Ask yourself if you have given enough time or space for the inhale. Do you have enough rich data? Have you sat with it long enough? Have you gotten under the skin of things?
6. Conversely, don’t get stuck in listening mode. Convert insights early and often into thoughtful action. Take a prototyping step forward and then observe its effects. Listen and make…inhale and creative exhale… repeat. It’s the interplay of these modes that gets to somewhere interesting.

 

Hear from Jessica and other creatives shaping the future at the 11th Annual 99U Conference, May 8-10, 2019 in New York City.

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