Kyle T. Webster: Build a Community, Not Just a Portfolio

Kyle T. Webster: Build a Community, Not Just a Portfolio

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.


An unrivaled innovator in the digital art and illustration world, Adobe Design Evangelist Kyle T. Webster is best known as the founder of, whose Photoshop brushes have been used by professionals at Disney, Pixar, Dreamworks, and Weta Digital. Kyle will be speaking at the 11th Annual 99U Conference taking place May 8-10 in New York City.

Q. What’s a skill that you believe will be futureproof?

A. The art of conversation. No matter how much we fill our time consuming content delivered via technology, we will always long for meaningful human interaction.

Q. What makes you believe in the power of conversation?

A. There is an abundance of goodwill in our community, but it is not easily accessible if we do not connect with one another on a deeper level than a portfolio review. I had the great opportunity to teach a two-week digital painting course in Berlin in 2015. It was one of the most delightful experiences of my life. And how did it come about? Because I went to the American Illustration book release party in NYC and had a wonderful, hour-long conversation with a fellow illustrator who ran the painting course. He had been looking for somebody to teach it with him. Sure, I was qualified to teach it, but so were hundreds of other artists. By putting myself in a position to meet other people, enjoy some conversation, and make a real human connection, this opportunity came to me. Once I had a chance to prove myself, I made the most of it, but I truly believe this chance existed because I had a pleasant conversation and made a good impression on a fellow human being. I am not discounting the importance of doing good work, but what has kept me advancing in my field is the ability to build genuine friendships with members of my community.

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

A. The world is waiting—get out there. Find people who share your interests and spend quality time with them building meaningful, lasting relationships.

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

from Adobe 99UAdobe 99U

Weighing the Risk: Pitching an Idea Before You’ve Nailed Down the Details

Weighing the Risk: Pitching an Idea Before You’ve Nailed Down the Details

Welcome to our column that explores the one element that affects almost every career decision—Risk, with a capital “R.” Since every choice we make carries a risk, Good F***ing Design Advice co-founder Brian Buirge is going to examine both sides of the equation behind the decisions that creative entrepreneurs have to make. And joining him in this column is GFDA co-founder Jason Bacher who will be designing the visuals that accompany each piece. (Fittingly, the duo lead a workshop in The Art of Risk-Taking.)

In this third installment, Brian reflects on how he and Jason were put on the spot to sell an idea they hadn’t quite fleshed out.


In early 2016, our five-year-old company was hitting all of the appropriate developmental milestones of a five-year old person: our vocabulary was growing, you could leave us alone with safety scissors, we were comfortable in public for short periods of time, and while our ability to do math was lagging a bit, we managed to make up for it in finger-painting techniques.

Our workshop was one of the first things we wanted to revisit with our newfound “maturity.” We began to feel it wasn’t a proper reflection of the direction we were headed. So, for a few months, we stopped offering it entirely, and banged our heads relentlessly on the drawing board of possibility—which my co-founder, Jason, and I often mistook for each other’s foreheads.

We finally zeroed in on an idea for a workshop called “The Art of Risk-Taking.” The concept was built around an approach to help creatives, or entrepreneurs, or anyone really, become more comfortable with being uncomfortable. We believed that risk and uncertainty were key ingredients for us specifically, and for the design process more broadly. Without them, we felt that the best we could hope for (and therefore everyone else) were stale approaches, rehashed concepts, and meager improvements to someone else’s ideas.

Confident that the compass was finally pointing in the right direction, I wrote two choppy paragraphs about the workshop and updated the GFDA website accordingly. From there, we tabled further development in favor of the more immediate fires that demanded our attention.

Rolling the dice with zero experience is quite different than shooting from the hip informed by years of practice. One is reckless, while the other is a calculable risk.

Two very short weeks later, while on a working vacation in Louisville, I received an email from someone at a Fortune 100 company who stumbled upon those two paragraphs, and wanted to know more about our soon-to-be-wildly-successful-but-not-at-all-fleshed-out-much-less-built workshop on risk-taking.

Naturally, our website gave the entirely false illusion that we’d been offering this workshop for quite a while. Consequently the biggest pitch of my life didn’t happen with a suit and tie in a conference room with lots of planning and a fancy deck. It happened in a pair of gym shorts, over the phone, from the breakfast bar of my friend’s concrete kitchen countertop. I asked for more money than I had ever been paid, for a workshop that wasn’t finished, for an event happening in less than a month’s time.

If you can believe it, the pitch was successful. It didn’t happen the way I would have ideally planned it—but then again, nothing ever goes according to plan, does it? Often the biggest and most important opportunities will manifest themselves at a moment’s notice, and you’ll have no time to plan your strategy and approach. In the absence of planning all you’re left with is whatever life has prepared you for until that moment.

While the granular details hadn’t been worked out, Jason and I had previously invested such a tremendous amount of time around the idea, its goals and objectives, that I was well-equipped to act in the moment and decisively sell the idea.

Rolling the dice with zero experience is quite different than shooting from the hip informed by years of practice. One is reckless, while the other is a calculable risk. The difference is having the discipline to know the difference.



from Adobe 99UAdobe 99U

Michael Ventura: Self-Observation Is the Skill of the Future

Michael Ventura: Self-Observation Is the Skill of the Future

The 2019 99U Conference is founded on the belief that when creatives take their rightful seat at the table, the future is bright. As we prepare for the conference in May, and for the larger future, we’re asking our speakers to expand upon the idea that creativity is futureproof and share a skill or characteristic they think is important to cultivate for the times ahead.


The founder of strategy and design firm Sub Rosa, Michael Ventura is a leader in the intersection of empathy, creativity, and business. Michael will be speaking at the 11th Annual 99U Conference taking place May 8-10 in New York City. Since our 2019 conference is all about the future, we asked Michael what skills he believes will be most valuable in the years ahead.

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

A. Self-observation. I know that might sound a little new-agey, but it’s one of the most important skills to develop. It’s the ability to hit pause, take a moment to evaluate yourself, and take stock of where you’re at. Ask yourself,  “Am I breathing?” I mean really breathing, not just panting at your desk while you frantically write emails and hustle to meetings. It also extends to your emotional state. What’s the most common emotion you’re feeling lately? Are you in control of the emotion or is it controlling you? Is it triggered by someone or something? Are you able to manage it? Trust your intuition and check in with yourself frequently.

Q. Has there been a time in your career when you realized the power of self-observation?

A. In my mid-20s I was already on my second entrepreneurial venture. I had started the company that would grow into Sub Rosa today. In addition, I had just launched a magazine. I was burning the candle at both ends. And then the levee broke. I was changing the water cooler one day and herniated three discs in my back. The hospital told me spinal fusion surgery was my only path to recovery. Instead, I found Chinese medicine—acupuncture and tai chi—to be helpful practices. They re-trained me to cultivate a sense of self-awareness.

Since that time, self observation and contemplation have become core principles of my leadership style. It’s not always easy, especially in the fast-paced world we live in, but ultimately it makes me a better listener, collaborator, and, frankly, human.

Q. Why will self-observation be so important in the future?

A. The future isn’t slowing down. Information is going to continue to bombard us from all angles. It’s only going to get more difficult to parse, digest, and respond to all of the newsfeeds, emails, pings, alerts, and push notifications. Self observation is an opportunity to stop the noise so you can gather yourself and act more productively, presently, and ultimately, be more in command.

Q. What’s the best way to get better at this?

A. It isn’t a switch you flip and immediately everything changes. It’s a dimmer that you slide until the ability eventually becomes second nature. Set a few times each day when you’re willing to stop whatever you’re doing, no matter how “critical” or “busy” you are, and take a moment to observe yourself. Ask yourself some of the questions I mentioned earlier. Think about what’s happening inside you and bring it into your awareness. Noticing is the first step in learning who you are and what you are going to do about it.

See Michael Ventura and more creative leaders, entrepreneurs, and artists at the 11th Annual 99U Conference.

from Adobe 99UAdobe 99U

How to Turn Intuition into a Practical Tool to Boost Creativity

How to Turn Intuition into a Practical Tool to Boost Creativity

Imagine if, before you tackle today’s creative work, you first needed to stand by your desk and say this:

Sing in me, Muse, and through me tell the story

Of this client who so excitedly hired me,

To shepherd their story,

And help build their brand,

On this hallowed internet ground.

Ridiculous, right? Well, for thousands of years, people didn’t think so. Creators throughout history, like all of those Ancient Greek poets you learned about in school, would routinely open their works by invoking the Muse. Without it, they believed, they were incapable of being creative.

Although that seems ludicrous, we suffer from distant echoes of that belief today. Of course, instead of the Muse, we now outsource our creativity to other things, invoking them before we feel ready to begin anything: the guru, the industry expert, the trend, the case study, the expert who we just need to meet for coffee to hear about their best practices, and so on.

We search for our answers “out there.” Our creativity is not ours to control. Apparently.

However, we all possess an inherent tool to be proactive about our abilities: our intuition. Unfortunately, we shy away from discussing the idea because it’s often viewed (mainly by those who control budgets) as something no more practical than invoking a Greek deity to do our work for us.

Why intuition isn’t taken seriously in business

In researching for my new book, I found countless definitions of intuition. Albert Einstein allegedly called it “a feeling for the order lying behind the appearance.” Authors like John Naisbitt (who defined it as “deriving meaning from data”) and Malcolm Gladwell (“rapid cognition”) have explored concept, while in business, entrepreneurs like Chase Jarvis, the CEO of CreativeLive, and even Amazon’s Jeff Bezos often refer to it as an internal guide to make better decisions. In research psychology, people like Gary Klein and Gerd Gigerenzer conclude that our ability to pattern match and find coincidences between situations help us either arrive at better conclusions (Klein) or weed out irrelevant information en route to one (Gigerenzer).

Regardless of how it’s defined, intuition doesn’t feel overly practical to use. To hone the skill, we’re forced to — what? — experience a whole mess of things in the world and hope that we’ve improved our intuition? And so, the business world often views conventional wisdom or trendy new tactics or expert advice as far superior to intuition, because it feels more concrete.

The power is real

What if we could make intuition concrete, too? The benefits seem too powerful not to try. You’ve experienced these benefits before, I’m sure: suddenly, you just know. Like an instant clarity generator, you’ve found your answers. Just imagine if we could be proactive about that!

Well, if we revisit the word itself, I think we can. “Intuition” comes from the Latin intueri, which simply means “to consider.” So, consider that the most creative among us don’t possess any gifts or receive special inspiration we lack. Consider that the best among us are masters at considering the world.

We can master that ability too, if only we’d make one switch in the way we make decisions at work: We need to stop obsessing over everyone else’s right answers for us and start asking ourselves better questions.

By improving our ability to ask great questions of the world, we’d stop acting like experts and start acting like investigators. Experts care about what works on average or in general, but investigators care about evidence. They may know the generalities, but they care far more deeply about their unique environment. They believe context holds the clues.

Our context contains three important variables — none of which have been factored into the conventional wisdom or best practice. Those variables are:

  • You (the person or people doing the work)
  • Your audience (the person or people receiving the work)
  • Your resources (the means to make the work happen)

If we informed our work by seeking answers from within that context, rather than searching “out there” for abstract or inspirational ideas, we’d better tailor our decisions to our own situation. I believe that process is the process of honing our intuition. It’s far from ephemeral. It’s quite practical.

Putting it into practice

It isn’t hard to find examples of business leaders and organizations that harness the power of intuition in making creative decisions. Here are just a few:

  • When Merriam-Webster evolved from being a bland presence on Twitter to one of the most beloved and hilarious handles, they investigated that first part of their context, themselves. “Let’s show the world how fun and relevant we are,” said chief digital officer Lisa Schneider. Their self-awareness, rather than general advice, drives their creativity.
  • When Death Wish Coffee exploded from a struggling cafe into a global ecommerce brand, founder Mike Brown investigated his customers. He recognized that they drank coffee for a different reason than the average coffee aficionado, and so the Death Wish brand and product makes total sense … for these specific customers. “Let’s create the world’s strongest coffee,” Mike thought. At Death Wish, the customer is the guide — not the expert.
  • When Unsplash launched, CEO Mikael Cho had precious little time and almost no marketing budget to drive business to his previous company, Crew. He had a few stock photos he’d previously purchased, one afternoon, and knowledge of free digital tools (like Tumblr) and community forums (like Hacker News). He embraced these limited and unique constraints and become more creative. He investigated his resources, and instead of following a “best practice,” he crafted his own.

Through these examples and dozens more, I witnessed the same behavior in creative minds who break from conventional wisdom, act like investigators, and hone their intuition.

They start by asking what I call a trigger question, an open-ended question about their specific situation. These can only be answered through reflection or testing.

Next, they asked a follow-up that I call a confirmation question, which ensures sufficient evidence that their path forward made sense to pursue, even if it broke from the convention (which, almost routinely, it did).

For instance, Merriam-Webster’s leaders asked the trigger question, “What do we aspire to do with our marketing?” They wanted to show the world how fun and relevant they are. Then they asked the confirmation question, “What’s our unfair advantage for reaching that aspiration?” They were witty and warm people, unlike their rather staid marketing tone of voice. They are lexicographers, which document popular use of language, i.e. track pop culture. They don’t set the rules. In fact, they track changes in them.

Whatever specific questions we ask, we can take control of our creativity by honing our intuition. To do so, we can better learn to consider the world around us. In the end, exceptional work isn’t created by the answers others give us, but by the questions we ask ourselves. So the next time you need to be creative, maybe skip the invocation to the Muse and try something far more practical: Trust your intuition.

from Adobe 99UAdobe 99U

The First Five Years: How to Stop Feeling Like a Failure

The First Five Years: How to Stop Feeling Like a Failure

Getting started in your creative career is tough. You’ve got boatloads of ambition and energy, but you lack experience, the kind of knowledge that feels like you can see into the future because you’ve been there before. So we’ve introduced a new column that will allow you to get the benefit of hindsight before you’ve actually gone through the experience. Welcome to “The First Five Years” where Mitch Goldstein, a professor of design at Rochester Institute of Technology, answers reader questions related to the uncharted waters of beginning a career. This month, Mitch answers a question about how to halt the negative cycle of comparing yourself to others.


Q. How do I stop feeling like a failure?

It’s long been said that failure is an important part of growth — a learning experience that is necessary for continuing to move forward with your practice. This is true, and as an educator I have to constantly make my students appreciate that without the insight of making bad work, they can never make great work. Failure can be valuable, but failure is not the goal, it is not something to strive for, it is not the point — it is merely a byproduct of trying new things, taking risks, and learning.

And that brings us to an important point: failure is useful, but feeling like a failure is not. In today’s world, feeling like a failure is incredibly easy; one of the worst parts of the internet in general and social media in particular is the accessibility of people you look up to. The people you admire online may be more established than you, and the ease of being on social media makes comparing your accomplishments to theirs almost effortless.

“Everybody — even the superstar — feels like an impostor at one time or another.”

Enjoy the connections the internet offers you, but don’t let them get in the way of your own development. You are you. You are not someone else, and one of the most destructive things you can do as a creative professional is to constantly compare your work to theirs, your accomplishments to theirs, and your recognition to theirs. Having heroes is fine, and paying attention to people you admire is healthy and can be a nice motivation or inspiration. Feeling miserable about yourself because you have not done the same things in the same way with the same popularity as your heroes is a toxic habit that you must try to stop. They all started somewhere, they have all had good projects and bad projects, they have all felt like failures and felt like successes — just like you.

And then, there is “impostor syndrome,” which is something else that has been exacerbated by the connectedness of the internet. I don’t think of impostor syndrome as a syndrome, I think of it as simply part of the human condition. Everybody — even the superstar — feels like an impostor at one time or another (and most people — including the superstar — feel like impostors often). This is not a bad thing, and leaning into the idea of approaching creative practice as an impostor can be beneficial — you are coming at something with fresh eyes, and may see things the seasoned “experts” might not.

Indeed, design is an abstract profession that mostly exists in the gray area of opinion and interpretation, rather than hard truths and simple facts.  Not knowing exactly what you are doing is a gift because there are no absolute “right” answers, and this is what makes design incredibly interesting. There is a reason why it’s called a “creative practice,” instead of a “creative know-exactly-how-to-do-it-perfectly.”

from Adobe 99UAdobe 99U

Design Debate: Do Illustrators Need Agents?

Design Debate: Do Illustrators Need Agents?

In our newest design debate, Alva Skog, Erin Aniker and Yuko Shimizu explore whether it pays for an illustrator to hire an agent. Ready, set, debate.

1. Having an agent means that you can concentrate on what you do best.
Alva Skog, freelance illustrator

I was considering going freelance straight after university, but the prospect of doing everything on my own was scary. Towards the end of my last semester, I emailed a bunch of agencies with my portfolio and I was lucky that my current agent, Jelly, got back to me.

I had always found it difficult to price my work. Before having an agent, I was concerned that I didn’t know how much an illustration was worth, and I didn’t quite grasp licensing. There’s so many things that you have to think about when you price an illustration: Where is it going to get used? How long will it get used for? Now, my agent does all of that thinking for me.

When a client contacts me with a commission, I direct them straight to my agent. My agent talks to them, and makes sure that the budget matches my time and labor. They usually up the price too, which is something I always found difficult to do on my own. If it’s a big commission, my agent deals with all the client feedback—so I don’t need to stress about that side of things. My agent also writes up contracts, invoices for jobs, and then chases invoices to make sure I actually get paid. All of this means that I can concentrate on what I do best: illustrating.

“There’s no doubt about it: social media, and the growth of online and offline creative communities has allowed freelancers to promote themselves and get their work out there, which has changed the role of an agent.”

In addition to all the obvious admin pros of working with an agent, there are lots of things Jelly have done for me that I didn’t expect. They’ve been extremely supportive of the fact I’m a recent graduate; we talk a lot about what kinds of commissions I would like to do in the future, and how I can make that happen. For example, we’ve been working closely to shape and broaden my portfolio. When I signed, I mostly had portraits; now we’ve been getting together more cityscapes and large scenes filled with lots of people. Working with an agent gives you a support system to explore new ways of working.

An agent, of course, also brings in bigger clients. I’m currently working with Apple, and that came through Jelly. I wouldn’t have been able to handle a big project like what I’ve done for Apple on my own! It’s been extremely helpful to have someone guide me through the process.

2. You learn invaluable skills through representing yourself.
Erin Aniker, freelance illustrator

I’ve been acting as my own agent and it’s been working out pretty well for me. But…over time, the admin and invoice-chasing has ground me down a bit. The more clients I get, the more time consuming that side of things is becoming. If the right agent approached me and we were a good fit, I would definitely consider signing with them.

Sending out emails and updating spreadsheets is definitely not what first comes to mind when you first think about becoming an illustrator. But the reality is, it’s important to be multifaceted as a practitioner. What I’ve personally found is that I don’t necessarily need an agent to find clients. I actually really enjoy connecting with new people, networking, and meeting new art directors and editors. There’s so many aspects of being my own agent that I like and which are important skills to learn, such as communicating and marketing. I also keep 100% of all the profits from my work, since no one takes a cut.

“When it comes to pricing, I’ve been doing quite well on my own.”

I’m very active online and have a tight creative network. We’re incredibly supportive of one another: someone will often recommend me for a job, and I’ll recommend them. I have many mentors and peers that I can turn to for guidance, and I would say the information that I’ve established through them can be just as valuable as an agent’s. There’s no doubt about it: social media, and the growth of online and offline creative communities has allowed freelancers to promote themselves and get their work out there, which has changed the role of an agent. Despite all of this, I imagine working with an illustration agent can help you focus more on the drawing side of things.

When it comes to pricing, I’ve been doing quite well on my own. I’m half Turkish, half British, and my mom is the best haggler I know. From an early age, we’d go to Turkish markets together and I learned the art of haggling, which I’ve now applied to pricing my illustrations. So, until an agency that’s a good fit comes along, I’ll just continue doing what I’m doing!

3. “Don’t stress about getting an agent. Start out on your own, and see how it goes.”
Yuko Shimizu, freelance illustrator and educator at School of Visual Arts

I don’t recommend that anyone starting out in illustration get an agent straight away. It’s a myth that once you get an agent, your career will be set. It’s not true that an agent means everything’s going to be fine and jobs are going to be pouring in. The truth is that if your work is good, you’re going to get work. That’s the only way that things are going to happen.

A lot of my students are international, so they need to get a Visa to stay and work in the U.S. If they have an agent, their Visa gets sponsored, so often international students will get an agent right of school, which makes sense. What usually happens though, is then other students see their work everywhere, and they think the agent is getting their former classmate work. But in reality, the agent has only approached the student because they were already getting work.

“An agent is only necessary when you start doing big jobs, for instance ad work, which needs someone to help negotiate and organize.”

Getting an agent is like entering into a marriage—it’s a commitment. Its their business as well as yours, so they’re only going to work with you if you’re going to be bringing work to them. It’s best to spend the first years of your career gathering clients on your own and getting your name out there, because then you have something to bargain with when the right agent does come along. When I got an agent after around 7 years of working on my own, we agreed that they would only get a cut from new clients that they were bringing to me. If you’re just starting out, how can you make those kinds of negotiations? An agent is only necessary when you start doing big jobs, for instance ad work, which needs someone to help negotiate and organize.

One of the best ways to begin as an illustrator is to do editorial and book jobs, which allow you to experiment and produce a lot of work quickly. You don’t need an agent to get editorial jobs—you send around your portfolio, and once you start to work for certain magazines and newspapers, other art directors will see your stuff, and you get more work. If you then have an agent, and they take a 25-30% cut from the small budget, what’s the point? We live in New York and rent is high, you know?

from Adobe 99UAdobe 99U

Collaborating on a Creative Project? Tips for Making It Work

Collaborating on a Creative Project? Tips for Making It Work

While creativity draws inspiration from many sources, the physical act of creating is often a solitary one. There’s a purity in wrestling a concept into words, or paint, or a photograph by oneself, without the competing influences of others.

But sometimes working alone is overrated. The best collaborations fuse two complementary skill sets and points of view to create something greater than the sum of its parts. When effective, a creative partnership can sustain and push you far beyond the point you would have reached on your own.

Isabel Lea, a UK-based designer, and Aaron Bernstein, a US-based photographer, have found this magic in each other. Both Adobe Creative Residents, the two met through the program last May. They hit it off immediately, and decided to collaborate on a project that combined their expertise and interests: language, in Lea’s case, and food in Bernstein’s. First conceived as a one-off series visualizing food idioms from around the world, the scope has since expanded to become an exploration of the relationship between language and food across a variety of visual mediums. (An initial series of images was published in December, with a second iteration, an editorial commission that explores a subset of English culture, to be released in late winter.)

For Lea and Bernstein, it’s been a validating, challenging, exhilarating process. Recently, the two sat down to interview one another about what goes into making a successful creative partnership. Below, insights from their conversation, including finding the right collaborator, working together across time zones, and why two can be better than one when it comes to breaking boundaries and taking risks.


Ask yourself, ‘Do I like, trust, and respect this person?’

Perhaps this goes without saying, but it’s important to like the person you are launching a creative endeavor with for the sole reason that you’ll be interacting with them a lot. “I talk to you more than I talk to anyone — like my mom,” Bernstein told Lea.

Trust and respect are just as important. Isabel and Bernstein are both intensively creative, but they come from different fields. “We respect the other one’s expertise,” Lea said. “I think sometimes it’s helpful to work with somebody who knows a little bit about what you do but can advise with a little bit of distance as well.”

“We can outwardly admit to each other that we don’t know what we’re doing and where this is going. But it’s fine because the other one will prop it up and keep it going instead of giving up and putting it in our graveyard of ‘almost’ projects.”

“I am not confident in graphic design at all. There’s a lot of trust there where I know I can mock up something really crappy in Illustrator and show it to you without feeling judged,” Bernstein agreed. “Then you can send me an iPhone photo to suggest a composition or something and I won’t judge you for that. But it gives us the space to grow our skills.”

This dynamic — a respect of one another’s expertise and opinions, coupled with an implicit trust that any effort to advance the project, no matter how clumsy, will be taken seriously — creates forward momentum.

“I think you know a collaborative process is working when you feel accountable, but not judged, and you feel like they trust you to do their job,” Lea said. “Maybe the other person doesn’t always understand, but I think we’ve got that point now where if the other person goes, ‘No, no, trust me, this will work,’ that we go, ‘Okay.’ That’s really important for pushing the boundaries of what we want to do.”

A jug of milk with a cap that reads "bad mood" spills over.

Adobe Creative Residents Isabel Lea and Aaron Bernstein are collaborating on a photography project about food idioms.

Make accountability a focus.

As most people who have embarked on a long-term creative project can tell you, at some point you will burn out on the very thing that sparked you into action. “It’s quite easy to give up on a project when you’ve only got yourself accountable,” Lea said. Having a partner makes throwing in the towel that much harder.

The best partnerships offer far more than this, of course. In the beginning, ambitious projects tend to be amorphous. It’s not clear where they are going or how they’ll evolve, which is both exhilarating and overwhelming.

For Lea and Bernstein, what started as a one-off series visualizing food idioms from around the world has morphed into an exploration of the interplay between food, language, and culture, an admittedly broad topic.

“Sometimes when you’re forced to have a conversation with yourself on Slack or iMessage, you solve the problem.”

“Because [this project] is so limitless, it’s not something that I could ever do alone,” Bernstein said. “I don’t think that I would be as willing to keep the end goals so open if it was just me because that scares me. I can’t concept that sort of thing.”

The key is finding someone who doesn’t just support you, but challenges you to push past the point you would have reached on your own. “It’s one of those things you don’t know until you try, and it starts working,” Lea said. “We did this one project, but then it’s spun off so many other opportunities that it seems silly not to run with it.”

Be each other’s sounding boards.

Collaborating with a partner can help with overarching challenges, such as imposter syndrome. “We can outwardly admit to each other that we don’t know what we’re doing and where this is going,” Bernstein said. “But it’s fine because the other one will prop it up and keep it going instead of giving up and putting it in our graveyard of ‘almost’ projects.”

But having someone who understands the bizarre, ultra-specific obstacles you are dealing with can be just as important. When shooting a photo for their second series, which involved mince pies, the package Lea shipped with the ingredients didn’t arrive in time. Bernstein struggled to find everything at American grocery stores.

“I had to be guided by your grandma, basically,” he told Lea. “I think it’s those little moments, too, where it’s like, ‘Okay, Isabel can understand why I’m stressed out about this,’ instead of just internalizing all of these little stressors and problems that drive me crazy in my own individual projects.”

Recognize that a difference in time zones can play to your advantage.

Living and working in different continents presents some obvious challenges. “It’s difficult because we have to be very organized,” Lea said. Anything that requires physical, in-person collaboration must be mapped out far in advance. What’s more, the time difference often made it impossible to share moments of confusion or excitement in real-time.

But the two have found that the distance makes certain forms of communication easier. Being five hours ahead “means that I can leave you with something in the morning,” Lea told Bernstein. He’ll often do work after she’s gone to bed, which means when she wakes up, “progress has been made.”

“Sometimes when you’re forced to have a conversation with yourself on Slack or iMessage, you solve the problem,” Bernstein said. “By the time that I wake up, it’s all sorted.”

“Or the other one where one of us will go, ‘Okay, here are three edits or versions or choices, I think, two, four, and six,’” Lea agreed. “Then we wake up to, ‘Yes, I agree, two, four, and six.’ We kind of already knew it anyway. But it’s nice to get that clarification.”

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