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Of all the big decisions we make, what to do for a living is often the most vexing. Do you go for your dream job or security? Should there even be a difference between a calling and your job, anyway? These are questions at the heart of designer, painter, and writer Elle Luna’s book The Crossroads of Should and Must: Find and Follow Your Passion. In this conversation, she describes how this visually innovative and inspiring book was informed by her own trajectory and why she walked away from plum jobs at IDEO, Uber and Mailbox.

Debbie: You started out studying film but switched to design and then finished your degree with a major in conceptual storytelling. At that point, what were you hoping to do?

Elle: I don’t know. That’s when you begin to panic, right? Yet I had heard about this magical little place that seemed off in the forest somewhere called IDEO, where there were all of these people from diverse backgrounds, solving pressing global problems. Whatever company that enabled that kind of collaboration, I wanted to be a part of it.

Debbie: You saw a job opening for a storyteller in the Chicago office of IDEO. Two weeks after you saw the ad, you started working there.

Elle: I quickly got an interview and I presented a lot of unresolved work. I presented more about the questions I was asking than answers because I was young and I wanted to learn. I wanted to be surrounded by people who were also asking interesting questions. I felt like I was able to find my people.

Debbie: You were there for several years. What was the most important thing you learned at IDEO?

Elle: Teamwork. You’d have an engineer, an architect, a writer, a graphic designer—you get those folks around a table, all looking at the same challenge, and everyone sees the answer differently. At first, this causes a lot of strife. What then begins to happen is the magic of iteration, the magic of things beginning to become larger than the sum of the parts. That’s when ideas can really take off. The end product is so much greater than just one person’s ideas.

Debbie: Eventually, you decided to leave IDEO without another job in the wings. At this point you had moved to work in their San Francisco office. What made you decide to leave?

Elle: When I got to San Francisco, I fell in love with the spirit of entrepreneurship—the startups that could go from an idea to an implemented product in six months. We had been working with major clients at IDEO, and to create change within those massive organizations often took years. To work with a small team became very interesting, so I started doing freelance here and there to see if I had what it took to be part of startup culture. When I began doing a lot more work on nights and weekends that was getting me up in the morning, I decided, “Okay, we can either do more of this work at IDEO, or I can go do that work with startups.” I talked about it with IDEO and they said, “We’re not doing that work actively at the moment, so go play and have fun.”

Debbie: Then you got a consulting job at Uber, and the app you developed beat out the Mars Rover and Tesla for the 2013 Fast Company Innovation by Design Award in the transportation category.

Elle: Thank you, thank you.

Debbie: You were in and out of Uber at that point and went to take a full-time job at Mailbox. What were you hired to do there?

Elle: Mailbox was this other product called Orchestra, which was a shared to-do list app for the iPhone. They needed extra design support, and very quickly I began to realize that maybe there’s something else here. Maybe there’s an idea beyond this idea. I started to fall in love with the idea of redesigning email from the ground up for the iPhone. At the time nobody had done it and it was really a silly idea; we were a small team that wanted to go up against Apple and Gmail and these monstrous teams with huge budgets. I joined the team full-time, and I was there for about a year.

Debbie: Mailbox was then acquired by Dropbox and you decided to leave again. At this point, you’re 31 years old. What made you create something wonderfully successful and then again say, “Thank you, bye”?

Elle: Are you seeing a pattern here?

Debbie: I am. And I want to understand it.

Elle: Mailbox was going so well and, from the perspective of having a brand at your fingertips, having a product that you’re bringing to life screen by screen, having a website that you’re also bringing to life—getting to touch all of those visual elements from a design perspective was exhilarating. You are literally defining how people spend time on their phone every day. Except somewhere along the way I started having this dream. It was a recurring dream and at first I couldn’t make much of it.
This is what the dream was: I would walk into a room that had concrete floors and really, really tall white walls, and it was like lights were inside the walls—they seemed to be glowing There was a stretch of warehouse windows running the length of one of the walls and a mattress on the floor. That was it. And in my dream, I sat down on this concrete floor, and I would just sit there and do nothing. I had a deep feeling of peace in that space, and then I would wake up.

Debbie: How often were you having these dreams?

Elle: I had a couple a week for months.

Debbie: I’ve done a little bit of reading about your dreams, and you write about how Mary Shelley wrote Frankenstein because she dreamt it; the tune for the song “Yesterday” by Paul McCartney was something he heard in a dream. What did you think about this dream? Did you feel compelled to bring it to life?

Elle: I was telling a friend about the dream and she asked the question that totally turned my life inside out. She said, “Have you ever thought about looking for this dream in real life?”

Debbie: So, what did you do?

Elle: I went and looked for the dream in real life.

Debbie: How do you find an apartment with concrete floors, warehouse windows, white walls, and a mattress on the floor?

Elle: To be totally frank, I had no idea what I was really looking for. I didn’t know if this was a studio space, if this was a business space, if this was a roommate’s house, if this was where I was intended to live. I didn’t know, but I had this instinct that it was inevitable. I didn’t tell anybody about this search because it felt ridiculous, right?

Debbie: What was the search criteria you were using?

Elle: Oh my goodness—any and all search criteria. One day, I’m scrolling through Craigslist and I saw it. I will never forget the feeling. I even have chills right now: experiencing something that you experienced in a dream is a very weird feeling.

Debbie: What did you think you were going to do in the white room?

Elle: I didn’t know until I showed up. On my very first night there, I reenacted the dream moment. I thought if I sit down on the floor, I’ll feel that peace. I sat down and instead I began to panic. I looked around at the entire absurdity of the moment, and not knowing what I was doing, or why, or what it was all about came crushing in on me.

I asked the room, “Why am I here?” As clear as day, the room replied, “It’s time to paint.” I had painted often as a kid and all through grad school, but somewhere along the way using my hands to make work was replaced by predominantly working within the computer. Somewhere along the way, the paints were put into a box and never moved to that next apartment.

The next morning I woke up, I went to the art supply store, I rebuilt my toolkit. All of these memories came racing back as I’m scanning the colors, the brushes. I went home and I began painting, and I basically painted every instant that I wasn’t at work. It was highly unsustainable. If I wasn’t at work making icons and working on Mailbox, I was at home covering all of my clothes in paint.

Debbie: Did you feel at this point the time was ready for you to make the leap?

Elle: There was a very specific moment. We were launching Mailbox. There were balloons everywhere, Twitter was humming, the launch was wildly successful. I will never forget sitting at my desk thinking, I’m getting older, I can do anything with my time. Anything. Is this what I want to be doing? Do I want to take these ideas and now put them onto Android and onto the web and onto all these other platforms? I can do it, but is that what I really, really want to be doing with my time?

It was just crystal clear. I had to go paint. I looked at my finances and figured I could buy myself a little bit of time to see if I could make a living as a working artist or if there was another option that got me closer to that reality. I felt so liberated by how clear the choice was. Choice is the wrong word—it was just so obvious. Then it was simply a logistical series of decisions: getting things lined up, getting things in place.

Debbie: Then you met the street artist and gallerist Ian Ross, and he helped push you in this direction. What happened when you met Ian?

Elle: Ian and his wife, Daniele, have a space in San Francisco where they bridge gallery and street experiences. I am not a street artist, but Daniele reached out to me and said, “What are you doing with all of this art? I see you posting it on Instagram.” Because I was posting all of it, for better and for worse. I said, “Well, I’m either painting over it or throwing it away.” “Stop that immediately,” she said, and she invited me to mount a pop-up show in the three days between exhibits. That moment taught me how important it is to get our work out of our studios and to see what larger story is being told. That particular show was titled Far from Shore, and it had 60 pieces of new work created in about six weeks.

Debbie: What made you start putting the work up on Instagram to begin with?

Elle: I had a friend who came over to my studio, saw the giant mess I was making, and said, “Elle, I have to break it to you. You’re doing terribly interesting things in here, but you keep posting photos of wine glasses and Sonoma. When are you going to start sharing your real life?”

Debbie: What was the most challenging thing that you had to confront in yourself?

Elle: The most challenging thing I had to confront in myself was this little voice in my head that said the most unthinkable things.

Debbie: Like what?

Elle: This is awful, this is awful, what are you doing? Why would you do that? Other people haven’t done it that way. You stole that from somebody else. You’re not original. It goes on and on and on. It’s a monster that continues to grow, because we continue to feed it. I got to a point where it had to stop. And you could see the duel in my head. The early paintings were broken and brutal and intense.

Debbie: The Crossroads of Should and Must: Find and Follow Your Passion started as a post on Medium. What was your motivation?

Elle: Remember that day, sitting at my desk at Mailbox? That was the feeling of being at a crossroads between what I should do and what I had to do, what I was compelled to do unavoidably. Choosing to paint was my must moment, it was a very big crossroads moment in my life.

Debbie: The post that you wrote went viral nearly instantaneously. I remember being very moved when I first read the piece online. Did the piece going viral surprise you or scare you, or both?

Elle: It totally scared me, because I thought there was something wrong with my phone. I share things online every day; the fact that this one hit caught me off guard. After seeing what a fast read that was for folks and how the images and the text could play together so well, I decided to extend the post into a book. That happened probably six months after the Medium post went out into the world and again, that the book should be half words and half pictures felt obvious, inevitable.

Debbie: Elle, why don’t we choose must every day?

Elle: Must is just on the other side of should. Should is this world of expectations, and it’s like a camouflaged force: it can creep in there when you’re not looking.

Debbie: It’s easier.

Elle:It is easier. Should is the river going one way. Even if you want to swim in a certain way, you have this force against you. Should oftentimes comes very early on in life, too. It can come from the time into which we’re born, the society or the community into which we’re born, the body into which we’re born. It could be the advertising, it could be a lot of different things that happen early in life that have us off and running a different race than the one we were intended to run.

Debbie: I contend that you have to work as hard at doing something you don’t like as something you love. Somehow it’s the choice that feels more difficult.

Elle: I love that. Living the life of should can be very pleasant, because you’re satisfying a lot of objectives. You’re usually satisfying a lot of systemic beliefs, and you’re usually making a lot of people very happy. If you feel like you or someone else is living in the world of should but they’re happy, cool. This book is for the folks who begin wondering what else is out there. It’s for that itching, that beginning of dissatisfaction.

Debbie: You write how must feels inherently selfish at first. Why is that?

Elle: Because the journey is within, the journey is inward. That can feel, conceptually, selfish.

Debbie: What is the role of solitude in following your must?

Elle: Considering technology’s role in our day-to-day lives, solitude is missing—it’s all but gone. We are so busy and we are so addicted to being busy.

Debbie: It’s a badge now.

Elle: It is. Solitude is so important if we want to connect to our must, if we want to begin to hear that voice inside. If we want to connect to our intuition, to the force of must, then we have to find solitude.
Finding that space doesn’t have to involve a white room from your dreams. It could be a park bench, it could be a spot at the public library, it could be a candle that you light that marks a sacred practice. It also has to be a psychological safe space. You can’t be interrupted, for which you might have to ask for help: I need to carve out this time; I need to be alone for my own health and wellness. Even if you have a family, even if you have a partner, claiming time for yourself is so important, because that’s the time you can connect to yourself.



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