Should. Must. And Our Lives: Five Questions with Author, Designer Elle Luna

Crossroads_LUNAElle Luna and I met several years ago via overlapping friend circles. The last meal we shared, several years ago, she departed accepting a ride in a pedicab piloted by a man in a spiderman costume. That kinda summarizes how wonderful her journey of the past several years have been.

Hunter Walk: Your book, The Crossroads of Should and Must, has really reverberated with the creative community. Did you originally write it for yourself or for others? Did it feel like a risk opening yourself up in that way?

Elle Luna: I got to a place in my life where I was asking a lot of questions. While I didn’t have the answers, I wasn’t really sure if I needed to because the questions in and of themselves were valuable. I wanted to understand what kind of work I was doing and why. Did I have a job, a career, or a calling? I wanted to know what my passion was, find my personal myth, and still keep a roof over my head. So I collected these questions, hit “publish” on an essay and within two weeks, it was shared to over five million people on Twitter. It turned out that a lot of people were asking similar questions. The blog post became a book and here we are.

Prior to publishing the blog post, I had been working at Mailbox, launching our iPhone app. I was the design lead and our mission was to revolutionize email for the mobile phone. Our launch was an unmitigated success, and I recall the deep joy and gratitude I felt about being a part of this team that built a tool that we felt would lighten the loads of people who were burdened by email. While things were going really well with our product launch, I was exhausted. Really, really exhausted.

I needed a rest, a retreat. Not just for a weekend or a week, but I needed to step away from it all. What I wanted was more than just a literal rest, but also a restful mind—free from all of the busyness of life, free from all of the hecticness that comes from goal-orientedness and meetings meetings meetings and all of the trappings of the corporate world. Which, admittedly, I adored, but I realized was causing a lot of trappings for me in my life.

Aristotle has a great name for this, he called it the tabula rasa. It means blank slate. I needed a tabula rasa where I could go and hear myself think, free from all of the external voices telling me how I should and shouldn’t live my life.

This was the moment that the crossroads appeared very clearly in my life: Should or Must? I was looking down two roads, and they were both appealing in their own ways, but they were different, and I had to choose. I reviewed my finances and saw that I could buy myself a window of time to step away from my job. In true blank slate form, I did not know what the future held, but I knew that I needed to leave, and so I put in my notice and quit.

I went home to my tabula rasa, a studio space in San Francisco, and my journey with art began to unfold. Along the way, I started to accumulate these questions, and once these ideas grew larger and more solidified, I shared them.

I’ve come to realize that the reason the post spoke to so many people is because we all arrive at this crossroads between Should and Must over and over again throughout our lives. Sometimes it’s a really big crossroads, and other times, it’s smaller. But we are constantly faced with the same question, again and again, and it is this— obey Should or honor Must?

HW: I’m sure you’ve gotten a ton of notes from people saying how Crossroads helped them take a new step in their lives. Any consistent fears in what was holding people back?

EL: The most common question I get is this one: “What if doing what I love doesn’t pay?” It’s a great question. I once watched this TED talk by Stefan Sagmeister that just blew me away. He talked about the differences between Jobs, Careers, and Callings. Jobs are activities we typically do from 9-5, for pay; Careers are systems of advancements over time where rewards are used to optimize behavior; and Callings are activities, or hobbies, even, which are pursued for intrinsic value, either with or without pay. This really caught me because I had never thought about the different modes of work. Have you? It made me wonder what I had… a job? a career? a calling? Or perhaps some mix of the three. It turns out that really wise people throughout time have combined these activities in different ways, which was inspiring. TS Elliot, for example, had a calling to be an author, which is why we know about him today. But did you know that he was also a banker? He was a brilliant financial mind in London. And I imagine that having a career as a banker created the space for him to pursue his passion. Similarly, I recently heard Elizabeth Gilbert give a talk where she said that she told her art that she would never, ever ask for it to put a roof over her head. She worked odd jobs until, one day, her books began making money and putting a roof over her head. It’s a good question to ask our callings: “Hey calling! Do you want to be responsible for paying the rent?” You might have a job 9-5 while you pursue your calling on nights and weekends. Or, you might pursue your calling 24/7 and make a living from it. There’s no right answer. And there’s dignity in all work. Just because you do something for money doesn’t make it dirty. You get to decide what’s right for you and your life.

While we place the blame on money, time or space as reasons for not pursuing our Must, I think the real reason we don’t go for it is something else. Something scarier. Something spoken about a lot less.


Should is how other people want us to live our lives. It’s all of the expectations and obligations that others layer upon us. Sometimes Shoulds are small, like “You should check out this movie!” Other times, Shoulds are large and insidious, like “You should sit in the back of the bus because of your skin color” or “You should not be educated because you are a girl.” When we choose Should, we can feel it in our bodies. Our muscles constrict, our body tenses. It’s an awful feeling. And the part that’s really hard is when culture at large says that we Should do something that we deeply, inwardly know is really wrong for us. When we live our lives in Should, we are essentially choosing to live our life for someone or something other than ourselves.

And the reason Should is so tricky is because Shoulds are put on us from the moment we’re born. This is an evolutionary process because we are essentially born wild creatures. Ask anyone with a toddler, they know! And parents place Shoulds on their children so that those wild creatures will know how to survive in this world. This is the process of socialization, and that’s what Shoulds do, they teach us how to survive.

Now, as the child grows up, it is a healthy process for them to examine those Shoulds, to question them, and to shed the Shoulds that do not serve their unique, evolving truth as a person. These are the Shoulds placed on them by family, community, and culture at large. This is the process of individuation, and it is very important. But sometimes, this process is delayed, or, at worst, doesn’t happen at all. We might even find ourselves as adults still living in a world of Shoulds from childhood that we inherited but never consciously examined.

When I talk about the process of shedding Shoulds, there seems to be a shift, a very palpable shift. Just this past week, I spoke at ALT Summit in Salt Lake City, and as I talked about how to bring our Shoulds into consciousness, I could feel the energy in the room relax, or was it release? As though suddenly there was a way to move forward, a way to bring those outdated belief systems to the surface and bring love to what had previously been hidden or shamed into not being seen or heard.

Where I’m headed now with my work is uncovering more about what Shoulds are like as a woman. Now, whether you’re a woman, a man, Latino, African American… are there Shoulds keep you categorized as that? Shoulds that keep you imprisoned? As I bring my Shoulds into consciousness, I’m asking: what Shoulds do I feel that society holds me accountable for? What are women obligated to do? This process has been a tremendously beautiful one, and in the book, I share a few methods that you can use to examine your  own Shoulds. But the reason this works, the reason it brings so much liberation to our lives is because Should is the doorkeeper to Must, the counterforce that works against even our very best intentions. So long as Should has a grip on us, our Must doesn’t stand a chance! And if our Must is strong and powerful without having dealt with Should, just wait until you’re really set loose! It’s like that great Janis Joplin lyric, “Freedom’s just another word for nothing left to lose.”

If we want to be free, we first have to understand why we are not free, what keeps us from being free. As we bring Shoulds into consciousness, they loosen their grip on our lives. That which was previously painful and avoided is now understood and served. That which once roused fear and anxiety is now transformed and inspires compassion. To bring our Shoulds into view is a miraculous gift, not only because your load lightens and your spirit becomes brighter, but also to know that your superpowers, your truest, deepest, most unique gifts, the light that you have been carrying and nurturing your whole life, is now ready to come forth and shine, shine, shine. If I have learned one thing from this journey, it’s that choosing Must, honoring who we are and why we are here, is the greatest thing we can do with our lives.

HW: From your Instagram feed, I see you doing a lot of international travel. Have you found differences across cultures in what it means to be creative?

EL: I recently had the tremendous privilege of being around some seriously brave, radiant and courageous people. I was at a girl’s school in rural Uttar Pradesh, India, which is the base of the base of the base of the pyramid. Here, where having a toilet is a luxury and being able to properly nourish your family and animals is practically impossible, there is a haven, a utopia for girls to get an education, which is equally unthinkable in a place where child marriages are all too common and the thought of educating a girl child simply doesn’t make economic sense to a frightening number of families. This school, called Pardada Pardadi, provides education, meals, doctors, education on rights, computer access… you name it… to girls pre-K through 12th grade. The founder, an incredible man named Sam Singh, decided to return to his hometown village and build this school after making what he calls “a dollar” as an SVP at DuPont. He chose to use his success to uplift his childhood community. It was his Must, even as people doubted his vision. It was his Must, even as angry disbelievers showered his car with bullets in Delhi (he was unhurt). It was his Must as four girls turned into fourteen hundred. Sam’s advice for anyone trying to make change is to just keep moving forward, to just keep going, to not stop, no matter what.

Just a few weeks ago, Sam Sing was on the “Jimmy Fallon Show” of India being interviewed about this incredible school that is changing the paradigm for girls. A school that was at first such a threat to the status quo is now being heralded as the future for education in India! Amazing, right? And to think, it all started because Sam believed, unwaveringly, in his Must. It makes me wonder if our journeys within don’t ultimately guide us back to our communities, a place to use our passions and talents to serve one another?

HW: From your experience as an author, what does the publishing industry feel like? How did it compare to your work as a designer in tech?

EL: Well, I suppose there are obvious differences. You can’t fix a bug in a printed artifact and you can’t push an update if something isn’t clear. A book is a snapshot of time, it’s of a moment, mistakes and all. Luckily, I haven’t caught a mistake, and I haven’t wanted to push any updates, but it definitely gave me serious pause before hitting “print.” I couldn’t shake the thought that if I had kids one day, they’d find this object in their library. Isn’t that funny? That was one of my biggest concerns: is what I’m about to say going to help our littlest people to live more joyful, peaceful, fulfilling lives?

A similarity between publishing and tech is that both have this incredible opportunity to create vehicles for ideas that help people. This begs the question, what happens when the vehicle is gone? For example, like anyone else who launched Mailbox today, I saw the sad message that it will be shutting down in a few days. Does this mean Mailbox is gone? Of course not. We have all of the lessons learned. We have the beauty of the dance between our design and engineering teams. We have the experiential elements that enabled an interaction that, in my own opinion, was magical. I see Mailbox everywhere—in other products, in how teams are being built, and in company culture. I suppose this is sort of a Buddhist idea, that things never really die—that there is an inter-being amongst all things. I believe in that. The same thing is true for the book. Once you plant a seed in someone’s head about Should and Must, once they begin to wonder if they’re living their life for someone or something other than themselves, once they begin that miraculous inward journey of reconnecting with their own voice, their own beliefs, and their own most authentic self, their heart is changed and you can see it. Their actions change. The person is evolving. It is unspeakably beautiful to experience someone seeking their personal truth, their personal myth. As Thoreau once said, “Convince me that you have a seed there, and I am prepared to expect miracles.”

HW: Any more books in you?

EL: Yes! I am finishing the art for my dear friend’s memoir. Keep your eyes peeled! In the meantime, you can check out The Crossroads of Should and Must here.