The Crossroads of Shouldand MustThis is a story about two roads — Should and Must. It’s apep talk for anyone who’s chosen Should for far too long — months, years, maybe a lifetime — and feels like it’sabout time they gave Must a shot

There are two paths in life: Should and Must. We arrive at this crossroads over

and over again. And each time, we get to choose.

Over the past year I’ve chosen Must again and again. And it was petrifying. Andat times it was dark. But I would never, ever, trade this past year for anything.This essay is my three biggest takeaways from the experience. It’s for anyonewho is thinking of making the jump from Should to Must. Anyone looking tofollow the energy deep within their chest but aren’t quite sure how.

Should is how others want us to show up in the world!—!how we’re supposed tothink, what we ought to say, what we should or shouldn’t do. It’s the vast array ofexpectations that others layer upon us. When we choose Should the journey issmooth, the risk is small.

Must is different—there aren’t options and we don’t have a choice.

Must is who we are, what we believe, and what we do when we are alone withour truest, most authentic self. It’s our instincts, our cravings and longings, thethings and places and ideas we burn for, the intuition that swells up fromsomewhere deep inside of us. Must is what happens when we stop conformingto other people’s ideals and start connecting to our own. Because when wechoose Must, we are no longer looking for inspiration out there. Instead, we are

listening to our calling from within, from some luminous, mysterious place.

Must is why Van Gogh painted his entire life without ever receiving publicrecognition. Must is why Mozart performed Don Giovani and Coltrane playedhis new sound, even as the critics called it ugly. Must is why that lawyer in histhirties spent three years writing his first novel only to be rejected by threedozen publishers. He honored his calling, eventually received a “yes,” and that

is why John Grisham is a household name today. Must isn’t exclusively forwriters and painters and composers, though. Must is why, in the early days,Airbnb sold boxes of cereal to make ends meet because no one would give themmoney and every conceivable metric said they should quit.

While working at Mailbox, I came across Stefan Sagmeister’s TED talk aboutjobs, careers, and callings.

He spoke about their differences, and I began to wonder which one I had. Atthe same time, I was also reading a biography about Picasso.

In it, Arianna Huffington describes the joy she felt learning about how Picassochose to live his life:

The more I discovered about his life and the more I delved into his art, the more the

two converged. “It’s not what an artist does that counts, but what he is,” Picasso said.

But his art was so thoroughly autobiographical that what he did was what he was.

Picasso’s life blended seamlessly with his work. It was all one huge swirling mixof bullfights and beaches and booze. And we could tell. Because to look at oneof Picasso’s canvases is quite literally to look into his soul. And this is exactlywhat happens when our life, our essence, is one and the same with our work.It’s when job descriptions and titles no longer make sense because we don’t go

to work— we are the work.

And this lead me to a big hypothesis. What if…

What if who we are and what we do become one and the same? What if ourwork is so thoroughly autobiographical that we can’t parse the product fromthe person? What if our jobs are our careers and our callings?

And this was about the time that my head exploded.

Choosing Must sounds fantastic, right? To step into the fullness of our gifts andoffer them up to the world in the form of our work.

Well, it turns out that choosing Must is scary, hard, and a lot like jumping off aterrifyingly high cliff where you can’t see anything down below.

It was one year ago that I jumped off the first of many cliffs, leaving a dreamjob at Mailbox to make art.

Choosing Must creates the kind of workthat puts ripples through the universe.But it starts as a whisper, a call from somewhere far away.

The path to my Must started with a recurring dream about a white room.

Concrete floors, white walls, and a mattress on the floor. That was it. And Iwould visit this room practically every night. One day, a friend asked thequestion that would forever change the course of my life: “Have you everthought about finding your dream in real life?” I hadn’t, but later, I began towonder…

Craigslist, I thought.

As I scanned the tiny photos of apartments for rent, I felt ridiculous. But then, Isaw it. The white room. There it was, literally right there on the computerscreen!—!my dream— in a tiny image just 72 x 72 pixels big.

And, just like that, my journey began.

Growing up in Texas, I had a vague idea of what it meant to be “called”!—!in the

grand sense of the word!—!although I had never experienced it for myself.Moses was a favorite story of mine, because Moses was the last person on earthwe would choose to lead thousands of people to the promised land. He wasquiet; he had a stutter; and yet, Moses was called.

“Follow your bliss and doors will open where there were no doors before,”modern philosopher Joseph Campbell wrote. But recently, someone asked me aquestion, “But what if I don’t hear the call?” he asked. “What if I want to hear itbut I can’t? What do I do then?”

And two ideas came to mind.

At Mailbox, we adopted a well-known practice from Amazon to write our futurepress release. That’s right, we wrote a real press release about a nonexistentproduct!—!the one that we wanted to exist in the world. We envisioned theheadlines. We dreamed of what would happen if all of our wildest dreams cametrue. We even taped it inside of a magazine and put it on the coffee table. Mostof us do this kind of big scary dreaming with our products, or our companies,but very few of us do it with our lives.

Roz Savage, a management consultant in London living “the big life” was 33

when she sat down and wrote two versions of her obituary:

The first was the life that I wanted to have. I thought of the obituaries that I enjoyed

reading, the people that I admired… the people [who] really knew how to live,” she

says. “The second version was the obituary that I was heading for!—!a conventional,

ordinary, pleasant life. The difference between the two was startling. Clearly

something was going to have to change… I felt I was getting a few things figured out.

But I was like a carpenter with a brand new set of tools and no wood to work on. I

needed a project. And so I decided to row the Atlantic.

Back at Mailbox, it was 8 a.m. on Thursday, February 7, 2013 when we poppedthe first bottle of champagne. There were 13 of us, and we were all wide-eyed,staring at our monitors, watching as nine months of work on the iPhone appwas released into the world. As I looked around at the incredible people in thatroom, and watched the live ticker grow and grow, I knew that this moment wasone of the highlights of my life. But, in the very back of my mind, I couldn’thelp but wonder what any of it had to do with my dream of a white room.

Choosing Must often requires a leap offaith.If you’ve ever peered out over the edge of a cliff, you’ve felt the fear.

Choosing Must raises questions that are scary, big, and often, without an easy

answer in sight. Here are three of the biggest fears I’ve heard, and what to doabout them.

01

Money can be a bridge to the freedom of exploring Musts. And it often doesn’t

require much. But it does require determination. Money can be used to buy youa day, a week, month of time to work on a Must, which may amount to nothing.Or it can be used to buy a sweater, a suit, a car!—!the value of which is obviousand low risk.

Of course, the best way to make money is to figure out what you love and thengive yourself to it. Because the people who consistently choose Must overShould find a way to make it work, and, once they take the leap, they find it’seasier to make money doing what they love than they ever imagined.

02

Finding our calling doesn’t mean we need to quit our jobs. And it also doesn’tmean we need to book a one-way ticket to a faraway magical land where there’sno cell service. As someone who did both of those things, I know first hand thatit’s easy to pack a small bag, wave goodbye, and push the eject button for awhile. But the return, the re-entry phase, can be absolutely brutal.

The harder road, trickier, and more sustainable, is to make shifts every day

within our existing reality. To integrate, not obliterate. For Sheryl Sandberg,Lean In was a tiny yet growing piece of her heart for years until it exploded intothe world!—!all the while she was still running one of the world’s biggestcompanies and raising two children. Weaving our Must into our existing realityis about co-designing small opportunities with our teams. It’s about settingaside quiet time to be alone with our thoughts, and then actually followingthrough. It’s about doing one small thing, anything, to honor our personal truth!—!today.

But while money and schedules are the reasons cited most often for not makingthe leap, I believe the real reason is something deeper and far scarier.

03

While Must comes from somewhere deep inside of us, a beautiful truth thatcalls to us from within, Should comes from somewhere external, a place that’sequally important and powerful. Should comes from the place we call home,the people we love, the world we’ve created—the people, places, and thingsthat define us.

It is here, standing at the cliff ’s edge, peering down below, hearing the siren’scall, that we feel the terrifying prospect of abandonment, failure, andhumiliation. And this is the exact moment when people decide against takingthe leap!—!to avoid that great unknown, that transformative place wherenothing is written, nothing is guaranteed, and everything is possible.

Grab a piece of paper and write the numbers one through ten on the left side ofthe page. At the top, title it “What am I so afraid of?” This is your Worst CaseScenario list. This is your list of things that make you think “They’re all goingto laugh at me.” These are your largest fears, and you’ve got ten minutes towrite them down.

Go.

Line by line, walk yourself through each one. Would they really laugh at you?They would? How do you feel about that? Line by line, have a conversationabout all of your fears. Would you really be homeless? Would you really bealone? Do you really need that much money? This is a list of your tradeoffs. Andthey are the biggest things standing in your way.

Choosing Must is a daily practice,a recurring choice.Just because we chose Should yesterday doesn’t mean we’ll choose Must today.And just because we chose Must today doesn’t mean we won’t slip back intoShould tomorrow.

Dusk was falling as I arrived at the white room from my dreams. It was stark,absolute, white, and a symbol of something new, of beginnings. As I lookedaround, I thought, “What on earth have I done? Why am I here?” And as clear asday, I heard a voice say, “It’s time to paint.”

As time passed, I found myself choosing Must more often than Should. Andover time, continuing to choose Must opened doors into worlds I never couldhave imagined. Here are three qualities I’ve integrated into my daily practicethat have helped me achieve a sustainable Must.

Solitude

Often times, reconnecting with the road to Must is not about doing a lot ofrunning around.

This solo inward journey has been called many things throughout time!—!themyths call it the labyrinth, the abyss, the forest, and the night journey.Culturally, it’s called the “walkabout,” the vision quest, and the pilgrimage. Intech, it’s recently been called “the Struggle” by Ben Horowitz.

Searching for solitude is how I eventually found myself in an Airbnb in Balialone for six weeks, in the middle of the rice paddies, with no phone, no email,and no walls on three sides of the house.

I called my new home “the house without walls.” It was wrapped in palm trees,smelled of jasmine, and over the coming weeks, the geckos and frogs andpeople would come and go as they pleased, because there were no rules and no

walls to stop them. I had long dreamed of being in a place where the inside andthe outside were one and the same.

For six weeks, in “the house without walls,” I slowed down, silenced the voices,and relaxed into a quiet place deep within myself. I dreamed under the palmtrees, night sky, and various phases of the moon.

Focus.

It was in “the house without walls” that I fell in love with the moon. And, oneday, a Balinese friend of mine decided to turn two of my paintings into textiles!—!for the fun of it.

Fast-forward a few months: I was back in San Francisco trying to figure outwhat to do with these exquisite textiles. The batik process of hand-paintingeach cloth was so beautiful, and so close to my own painting practice, that Iwanted to find a way to combine these techniques on a larger scale. So Idecided to go to New York, hunker down in an Airbnb, and figure it out in twoweeks.

A friend of mine once compared focus to the beam of a mag light!—!if you keepthe light unfocused, light shines everywhere. It’s bright, but it’s blinding.

If you focus the light and tighten it, the light becomes a laser beam. Focusedand strong.

Bring others in.

As a former IDEO-er who believes in the power of human-centered design, I

began to wonder, even worry, how this inward journey would connect with theoutside world. And this is what I found:

During my two weeks in New York, I emailed a dozen of the most talented,brilliant women I knew, inviting them to collectively review my work and giveme feedback at the end of my sprint. Of course I needed to bring others in, Isuddenly realized, but not until after I knew what I was working on and why.

The women gave invaluable feedback, leading to significant insights. And this iswhy, the very next week, I found myself Bali-bound again. Except this time,with 200 yards of raw fabric. Working with master batik artists, wehand-painted 100 limited edition pieces of art, inspired by the phases of themoon. We launched the textiles as the inaugural collection of Bulan Project,and sold out in two weeks.

Photo by Michael O’Neal

Those who choose must.When who we are and what we do are one and the same, we are walking theroad of Must. When we choose Must, what we create is ourselves. It is a body ofwork. When we make something because we Must, not just because we can, it isthe difference between disposable products that last a few years andlife-affirming movements that sustain generations.

Choosing Must is Industrial designer David Pierce’s tattoo of a ruler runningthe length of his arm because his craft and his physical body are one and thesame.

Choosing Must is Charles and Ray Eames who designed their entire lifetogether and made their entire lives about design.

Choosing Must is Steve Jobs referring to Jony Ive not as a colleague, nor as acreative partner, but as a “Spiritual Partner.”

If you believe that you have something special inside of you, and you feel it’sabout time you gave it a shot, honor that calling in some small way!—!today.

If you feel a knot in your stomach because you can see the enormous distancebetween your dreams and your daily reality, do one thing to tighten your gripon what you want!—!today.

If you’ve been peering out over the edge of the cliff but can’t quite make theleap, dig a little deeper and find out what’s stopping you!—!today.

Because there is a recurring choice in life, and it occurs at the intersection oftwo roads. We arrive at this place again and again. And today, you get to choose.

WRITTEN BY

elle lunaelleluna.com

Thanks to: First Round Capital, Craig Mod, Kate Lee, Om Malik

Cover photo: Photo by Michael George