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.

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An unrivaled innovator in the digital art and illustration world, Adobe Design Evangelist Kyle T. Webster is best known as the founder of KyleBrush.com, 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.

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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.

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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.

 

 

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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.

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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.

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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.

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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.

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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.”

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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?

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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.

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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.”

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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Looking for a Career Boost? What Creative Coaches Want You to Know

It’s common for athletes, executives, and opera stars to have performances coaches—someone to set goals, benchmarks, tackle potential, and keep them in shape. But coaching has expanded beyond the C-Suite and the playing field to ambitious creatives at all levels of their careers.

Why this expansion? Part of the answer is pragmatic: freelancers and side hustlers now make of 34% of the U.S. economy. These entrepreneurial workers are following trajectories that don’t have built-in career development, pay raises and promotions, or retirement plans; they must create their own career structures. Sans the traditional office environment, an informal network of mentors and service journalism (ahem, you’re welcome) can often be the only sounding board or context to inform that structure.

But it’s not only freelancers who are feeling the pinch of a career without feedback, context, and professional development. During the Great Recession, large companies cut an entire generation of middle management to slash costs. And afterwards? When CEOs saw that workers kept coming in and performing, those managers were never rehired. The dearth of managers could be connected to so many company staffers now feeling adrift at work, just like freelancers, without the typical culture of management and people development from which previous generations benefited. So coaches stepped into the void, working with independent freelancers and self-starters, but also acting as consultants for big companies, serving as a resource for staff and filling in a management gap with feedback, goal-setting, and advice.

Since they’ve seen it all, we asked a few creative career coaches about the most common problems their clients are facing and got some advice on how to cultivate a career when it feels like you’re going it alone.

1. Recognize that tackling career problems may mean tackling problems in your personal life (and vice versa)

For many of us, there are no clear boundaries between our personal and professional lives; pain points in one area affect empowerment in the other. That’s why coaches address both business and personal goals as one.

“People come to me when they want to grow,” says Kristine Steinberg, who started out as an arts psychotherapist before becoming a coach for companies like New Lab, TED, Adidas, and Microsoft. “We work on the future they want to design, the future self they want to live in,” she says.

Since creatives’ future selves aren’t siloed into separate business and personal inboxes, creative coaches often wear many hats: confidante, mentor, and business partner.

2. Take as much care navigating opportunity as navigating hardship.

Contrary to popular belief, coaches are not only called in at times of crisis. In fact, they’re often most useful to those embarking upon exciting opportunities. Their value is that they provide accountability, no matter what the situation.  

“Creatives don’t struggle for ideas,” says Tina Essmaker, who spent a decade in social work before launching a design publication called The Great Discontent, and now coaches both independent and company clients. “They struggle to make them happen and take action.”

Whether you need help navigating a new project idea, choosing between multiple job opportunities, or stretching into a promotion, a coach can be a useful partner, providing perspective at times of paralyzing opportunity. The most powerful support they can offer is tactically breaking down the project into steps, suggesting resources, setting goals, and providing accountability in a vacuum. “It’s like having a partner who’s invested in you succeeding, but not invested in the project needing to be a certain way,” says Essmaker.

3. Remember that uncertainty is water in the creative industry. The only island is being brave.

Creatives live in an ambiguous world that is constantly iterating and evolving. The creative’s challenge is to sustainably manage that uncertainty.

For those times when everything is great on paper, but you’re feeling overwhelmed, Essmaker prioritizes cultivating bravery over agonizing what the right answer is. “Being able to hang out in that state of ambiguity long enough to know what’s next for you [is important],” she says. “If you try to make a decision out of fear or a scarcity mentality, you’re probably going to make the wrong one.”

Essmaker acknowledges that we all have good days and bad days. On the good days, the foundational things that fulfill us and that we value are clear. Trust the compass that comes from those good days to see you through the days that you feel rudderless and frightened. Essmaker advocates taking action while in the optimistic zones. “Make decisions when you’re having a good day and you have the energy to have insight,” she says. On the days when you’re scared, wait and sleep on it before you make that life-changing choice.

4. Don’t go to Bali. Go find the problem.

Getting unstuck is a prime reason creatives reach out to coaches, but often it takes some detective work to get through the layers to find the root of an issue that can manifest itself in a variety of ways: feeling out of balance, finding work all-consuming, or just not being happy without knowing why. A client may be struggling with how to ask for a raise, but a coaching conversation may reveal that the underlying issue is the client’s sense of self-worth. Or, a client may voice a desire to uproot—quit a job, leave a relationship, and move to a new city.

“It ends up being a surface level symptom to a different problem,” diagnoses Heath Ellis, who prefers the title “expansion guide” and works with clients such as Creative Morning’s Tina Roth Eisenberg.

Sure, uprooting and moving to Bali sounds great. But wherever you go, there you are; the desire to drop everything and start over doesn’t tackle the underlying issues which will no doubt resurface, even in Bali. “When people tend to run into the same issues—if it were a relationship, it would be ‘I keep dating the same girl and it never works’—there’s a subconscious pattern that needs to be healed,” says Ellis.

Coaches work on finding small steps and changes that put their clients in the driver’s seat in a more sustainable way than doing a reboot every few years. “The answer is not uprooting your entire life and career,” says Essmaker. “It’s looking at where you are and the changes you want to make where you are.” To do that, do some soul searching to identify the real energy behind your actions or feelings—anything from boredom to aversion to imposter syndrome—and then map that information back to a place where you can make a change. 

5. Own your results.

The common thread in so much coaching, is for people realize how much control they actually have. Most of the time we act unconsciously, responding to deadlines, responsibilities, and a fear of failure or of disappointing others. Ellis works to get creatives to own their results. “If something doesn’t work, it’s not your girlfriend or your boyfriend’s fault. It’s not your company or your boss. It’s something inside of you,” he says. “You’re creating your results. As painful as that can feel if your results suck right now, that’s super empowering,” he says.

Coaches provide the pillars that support a thriving career—feedback, accountability, resources, soul searching, and someone whose ultimate goal is your individual success. As our world of work becomes ever more entrepreneurial, ambitious, and, frankly, overworked, the kind of support they offer is key to preventing burnout and cultivating a thoughtful and empowered career.

Bonus: 

To get you started on exercising those conscious career muscles, we asked Kristine Steinberg to share a few of the questions she asks her clients, to act as soul-searching thought starters. Happy homework!

Are you operating at your highest potential?

• How are you thriving in your career?
• How are you leveraging your greatest talents and gifts in your work?
• Are you living to your fullest potential?
• If so – why?
• If not – what is getting in your way?
• What is your future vision of yourself?
• How can you manifest that vision?
• What is one thing you can do today to drive yourself to the next level of excellence?

Are you looking to get unstuck?

• What patterns in your behavior or actions are becoming repetitive and redundant in a negative way?
• If there was a new behavior or action you could take to break this pattern, what would it be? Can you commit to that?
• How do you think people perceive you? Is that okay with you or do you want to shift that perception?
• What is draining your energy?
• What would give you energy if you had the motivation to pursue it?
• If you were not stuck, what would be possible?

With a bit of soul searching and a commitment to acknowledging your dreams and insecurities, you can be on your way to a more fulfilling career.

 

 

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Meet the Founder of Bev, the Canned Rosé That’s Taking on Toxic Masculinity

Hyper masculinity had better watch out: Alix Peabody is on a mission.

The first-time founder has a plan to shake up the male-dominated alcohol industry with an eye-popping coral canned rosé called Bev. Her secret weapon? A “Break the Glass” message that takes aim at the toxic world of tech parties, date rape culture, and hyper masculinity.

Peabody drained her life savings and bought 300 gallons of rosé to launch Bev in 2018. Now, she arrives at 6 a.m. sales pitch meetings—where distributors are used to seeing men in flannel shirts explain the new Sam Adams lager—with a team of 10 women who bombard the room with decks of memes, boombox-led stretches, and pink donuts. It looks like she’s selling a brand, but really, she’s trying to reshape an industry.

“For so long, the alcohol industry has capitalized on people’s insecurities rather than their strengths,” says Peabody. “It has perpetuated a culture that is so unhealthy and unfair to both men and women. We want to redefine what that culture looks like.”

Now, she’s landed a partnership with Reyes, the biggest beer distributor in America. We got in touch with Alix to hear about going from $12 in the bank to a fundraising round of $2.2 million, and how she’s popping the top off of a beer-dominated market.

***

Q. Bev came about in an unlikely way. Tell us how it started.

A. I’d had these weird health issues that nobody could figure out. I’d had six surgeries in 18 months and was $20,000 or $30,000 deep in medical bills. So I started throwing parties to help pay off my medical bills. They were basically ragers at my aunt and uncle’s house in Sonoma. These were 200-person parties and they were during the day so they were called the Sonoma Daygers. You’ve read all about all the kinds of parties that go on in tech land in Silicon Valley: dingy and creepy, with women flown in from LA and paid to be there. The Daygers were the opposite. We would get crazy costumes, like boas and sparkly hats, and by the end of the night everyone was wearing something random and bright and dancing the funky chicken like nobody cares. If I were to liken it to anything, it would be Burning Man: radical self-expression, inclusive, everyone’s having a good time.

The name Bev is both a shorthand for beverage and a reference to an imaginary brand personality named Beverly.

Q. When did you sense there was a business opportunity here?  

A. I got addicted to the idea of the “female-owned party.” I wanted to build it, but I didn’t really know how. I quickly realized that if I wanted a brand that was going to take flight, I needed something actually tied down to a product. I had this ‘aha moment’ where I realized that the lowest common denominator of every party you’ve ever been to is alcohol. I started to look at the alcohol industry, and that’s when I realized that it’s really screwed up. When you look at what’s for women or depicts women in a strong way, there’s nothing there. You get Skinnygirl Margarita and White Girl Rosé and that’s the end. Everything is by and for men. Date rape culture really stems from a hyper-masculine social scene. The alcohol industry at large is the biggest perpetrator of that culture.

Q. How did you go from a square one idea to launching a company?

A. I cashed my 401(k) and bought 300 gallons of rosé. Then I set out to fundraise. I researched some angel investors and what parties they were going to, and flooded those parties with product. Then three days later I’d say, “Oh I’m raising.” Then they would tell me, “That stuff’s everywhere!” And I was like “That’s so crazy!” Just kidding—I’d put it there. I raised about $2.2 million. Now, we’re launching with the largest beer distributor in America, Reyes. We’re the only product they’ve ever taken on in their history from launch. And we’re their first canned wine. It’s really exciting.

Q. Why do you think your distributor took that leap with you?

A. The reality is, no one’s ever done anything like what we’re doing. I don’t say that to sound cocky. It just doesn’t exist to have an alcohol company that’s women run, women owned, women built and is not just ‘pink it and drink it’.

Q. How did alcohol become so male-dominated?

A. The alcohol industry is weird because of Prohibition. The people in distribution who became powerful at that time were, for all intents and purposes, drug dealers. They were doing something very illegal. Now, distributors are billion-dollar family-owned businesses, started by the same people who were doing criminal activity during Prohibition. That’s who we’re dealing with—people who are really kind of scary, to be honest. I was just talking to one of our distributors the other day who was telling us stories of his childhood and how he’s been stabbed eight times. It’s been a male-dominated industry for so long.

 

The full Bev team makes an appearance when Peabody pitches the brand to distributors.

Q. Why do you think that’s shifting?

A. The liquor industry in America is dramatically changing. Historically, women went to the grocery store and men when to the liquor store.  Which, by the way, is why the liquor store was dingy; it was the place only the man went. Now, in large part because of the legalization of booze in grocery stores, women are buying the household wine. So, there’s a huge hole in the market for something like Bev.

Q. The identity of the brand is a real eye-popper. Where did the design come from?

A. I wanted it to be female without being ditzy. I wanted it to infer a woman’s name, Bev, and try to give her a personality. But it’s also just a cute name for ‘beverage’. We wanted it to be sleek, bright, unapologetic, slightly retro, and personable. My favorite color is bright coral and we were making a brand centered around being unapologetically yourself. So, I said, “I’m going to unapologetically make this can bright coral.” The original logo was just our handwriting. We literally wrote ‘Bev’ and ‘Made by Chicks’ on the side of the can and made a font out of it.

Q. Bev started with 300 gallons of rosé. What kinds of numbers are you looking at now?

A. The Reyes distribution partnership has been huge. We went from pretty much zero accounts to over 100 in two weeks. Bev now has a team of 10 people. And we’re launching in new markets across the country, starting with SoCal, Nashville, and NYC.

Q. For anyone looking to follow in your footsteps, what does it take to be a good entrepreneur?

A. You will face extraordinarily difficult decisions and challenges. Entrepreneurs don’t fail because they fail; they fail because they give up. You’ve got to know that they can throw anything at you and you’re not going to give up. At one point during the fundraising period, I had $12 to my name. It was really awful. And literally, eight days later, I had raised half a million dollars. It was the hardest and also the most beautiful time in my life. It sucks a lot of the time. But, when you feel like your entire world is falling apart, that means you’re close and it’s about to happen for you.

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