The Crossroads of Should

and Must

This is a story about two roadsShould and Must. Its a

pep talk for anyone whos chosen Should for far too long
months, years, maybe a lifetimeand feels like its
about 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 Ive chosen Must again and again. And it was petrifying. And
at 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. Its for anyone
who is thinking of making the jump from Should to Must. Anyone looking to
follow the energy deep within their chest but arent quite sure how.
Should is how others want us to show up in the world!!how were supposed to
think, what we ought to say, what we should or shouldnt do. Its the vast array of
expectations that others layer upon us. When we choose Should the journey is
smooth, the risk is small.
Must is differentthere arent options and we dont have a choice.
Must is who we are, what we believe, and what we do when we are alone with
our truest, most authentic self. Its our instincts, our cravings and longings, the
things and places and ideas we burn for, the intuition that swells up from
somewhere deep inside of us. Must is what happens when we stop conforming
to other peoples ideals and start connecting to our own. Because when we
choose 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 public
recognition. Must is why Mozart performed Don Giovani and Coltrane played
his new sound, even as the critics called it ugly. Must is why that lawyer in his
thirties spent three years writing his first novel only to be rejected by three
dozen publishers. He honored his calling, eventually received a yes, and that

is why John Grisham is a household name today. Must isnt exclusively for
writers 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 them
money and every conceivable metric said they should quit.

While working at Mailbox, I came across Stefan Sagmeisters TED talk about
jobs, careers, and callings.

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

In it, Arianna Huffington describes the joy she felt learning about how Picasso
chose to live his life:
The more I discovered about his life and the more I delved into his art, the more the
two converged. Its 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.

Picassos life blended seamlessly with his work. It was all one huge swirling mix
of bullfights and beaches and booze. And we could tell. Because to look at one
of Picassos canvases is quite literally to look into his soul. And this is exactly
what happens when our life, our essence, is one and the same with our work.
Its when job descriptions and titles no longer make sense because we dont 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 our
work is so thoroughly autobiographical that we cant parse the product from
the 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 and
offer 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 a
terrifyingly high cliff where you cant see anything down below.
It was one year ago that I jumped off the first of many cliffs, leaving a dream
job at Mailbox to make art.

Choosing Must creates the kind of work

that 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 I
would visit this room practically every night. One day, a friend asked the
question that would forever change the course of my life: Have you ever
thought about finding your dream in real life? I hadnt, but later, I began to
wonder

Craigslist, I thought.

As I scanned the tiny photos of apartments for rent, I felt ridiculous. But then, I
saw it. The white room. There it was, literally right there on the computer
screen!!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 earth
we would choose to lead thousands of people to the promised land. He was
quiet; 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 a
question, But what if I dont hear the call? he asked. What if I want to hear it
but I cant? What do I do then?
And two ideas came to mind.

At Mailbox, we adopted a well-known practice from Amazon to write our future

press release. Thats right, we wrote a real press release about a nonexistent
product!!the one that we wanted to exist in the world. We envisioned the
headlines. We dreamed of what would happen if all of our wildest dreams came
true. We even taped it inside of a magazine and put it on the coffee table. Most
of 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 popped

the 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 app
was released into the world. As I looked around at the incredible people in that
room, and watched the live ticker grow and grow, I knew that this moment was
one of the highlights of my life. But, in the very back of my mind, I couldnt
help but wonder what any of it had to do with my dream of a white room.

Choosing Must often requires a leap of

faith.
If youve ever peered out over the edge of a cliff, youve 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 Ive heard, and what to do
about them.

01

Money can be a bridge to the freedom of exploring Musts. And it often doesnt

require much. But it does require determination. Money can be used to buy you
a 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 obvious
and low risk.
Of course, the best way to make money is to figure out what you love and then
give yourself to it. Because the people who consistently choose Must over
Should find a way to make it work, and, once they take the leap, they find its
easier to make money doing what they love than they ever imagined.

02

Finding our calling doesnt mean we need to quit our jobs. And it also doesnt
mean we need to book a one-way ticket to a faraway magical land where theres
no cell service. As someone who did both of those things, I know first hand that
its easy to pack a small bag, wave goodbye, and push the eject button for a
while. 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 into
the world!!all the while she was still running one of the worlds biggest
companies and raising two children. Weaving our Must into our existing reality
is about co-designing small opportunities with our teams. Its about setting
aside quiet time to be alone with our thoughts, and then actually following
through. Its 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 making
the 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 that
calls to us from within, Should comes from somewhere external, a place thats
equally important and powerful. Should comes from the place we call home,
the people we love, the world weve createdthe people, places, and things
that define us.

It is here, standing at the cliff s edge, peering down below, hearing the sirens
call, that we feel the terrifying prospect of abandonment, failure, and
humiliation. And this is the exact moment when people decide against taking
the leap!!to avoid that great unknown, that transformative place where
nothing 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 of
the page. At the top, title it What am I so afraid of? This is your Worst Case
Scenario list. This is your list of things that make you think Theyre all going
to laugh at me. These are your largest fears, and youve got ten minutes to
write 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 conversation
about all of your fears. Would you really be homeless? Would you really be
alone? Do you really need that much money? This is a list of your tradeoffs. And
they are the biggest things standing in your way.

Choosing Must is a daily practice,

a recurring choice.
Just because we chose Should yesterday doesnt mean well choose Must today.
And just because we chose Must today doesnt mean we wont slip back into
Should 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 looked
around, I thought, What on earth have I done? Why am I here? And as clear as
day, I heard a voice say, Its time to paint.

As time passed, I found myself choosing Must more often than Should. And
over time, continuing to choose Must opened doors into worlds I never could
have imagined. Here are three qualities Ive integrated into my daily practice
that have helped me achieve a sustainable Must.

Solitude

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

This solo inward journey has been called many things throughout time!!the
myths call it the labyrinth, the abyss, the forest, and the night journey.
Culturally, its called the walkabout, the vision quest, and the pilgrimage. In
tech, its recently been called the Struggle by Ben Horowitz.

Searching for solitude is how I eventually found myself in an Airbnb in Bali

alone 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 and
people 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 and
the 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 palm
trees, 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, one
day, 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 out
what to do with these exquisite textiles. The batik process of hand-painting
each cloth was so beautiful, and so close to my own painting practice, that I
wanted to find a way to combine these techniques on a larger scale. So I
decided to go to New York, hunker down in an Airbnb, and figure it out in two
weeks.

A friend of mine once compared focus to the beam of a mag light!!if you keep
the light unfocused, light shines everywhere. Its bright, but its blinding.

If you focus the light and tighten it, the light becomes a laser beam. Focused
and 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 the
outside 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 give
me feedback at the end of my sprint. Of course I needed to bring others in, I
suddenly 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 is
why, the very next week, I found myself Bali-bound again. Except this time,
with 200 yards of raw fabric. Working with master batik artists, we
hand-painted 100 limited edition pieces of art, inspired by the phases of the
moon. We launched the textiles as the inaugural collection of Bulan Project,
and sold out in two weeks.

Photo by Michael ONeal

Those who choose must.

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

Choosing Must is Industrial designer David Pierces tattoo of a ruler running

the length of his arm because his craft and his physical body are one and the
same.

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

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

If you believe that you have something special inside of you, and you feel its
about 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 distance
between your dreams and your daily reality, do one thing to tighten your grip
on what you want!!today.

If youve been peering out over the edge of the cliff but cant quite make the
leap, dig a little deeper and find out whats stopping you!!today.
Because there is a recurring choice in life, and it occurs at the intersection of
two roads. We arrive at this place again and again. And today, you get to choose.

W RITTEN BY

elle luna
elleluna.com
Thanks to: First Round Capital, Craig Mod, Kate Lee, Om Malik
Cover photo: Photo by Michael George