The Heart To Start: Win the Inner War & Let Your Art Shine

C U R I O S I T Y F I R S T
It is good to love many things, for therein
lies the true strength…What is done in love
is well done.
—Vincent Van Gogh
O N J U LY 1 8 , 2 0 0 7 ,
I opened my eyes to vastness. I could do
anything I wanted with the hours that stretched out before me – today,
tomorrow, and the day after that. That was as exciting as it was frightening. It
was my first day of self-employment.
I thought about all the things I had dreamed I could do, if only I had the time.
Well, here was the opportunity right in front of me. It was as if I had picked a
fight with a seven-foot giant in a bar parking lot, and my buddies who had
been holding me back finally let go and said, “Okay, go for it.” The woolly
mammoth of the blank canvas was staring me down. I could make something
great, or I could spiral into playing Guitar Hero and eating nachos for twelve
hours a day.
I needed a strategy to fight against distractions. I needed a strategy to take my
mind off the pressure of finally having a real opportunity to follow my
dreams. The strategy I settled on was simple: Curiosity first.
As I lingered under the warm covers of my bed that first day on my own, I
thought back to when I was a child. I would sit in my room alone and draw
for hours. My friends in the neighborhood might come to my driveway and
yell up to my window and ask if I wanted to play kickball. “No thanks,” I
would say. I was busy. The time would melt by so effortlessly I would forget
to eat.
I figured if I could fill up as much of my day with that feeling as possible –
that feeling of “flow” – that would be enough to keep myself motivated. That

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would be enough to get myself out of bed each day.
Your will to start making your art has to fight against everything that tries to
hold it back. You may feel like you don’t have the time. You may find
yourself constantly distracted. You may feel too scared.
But if you have the right fuel, you can bust right through everything. Once
you get moving, that fuel can keep you going consistently.
One of the best forms of that fuel is your own curiosity. If you learn how to
connect with your curiosity, not only will it propel you through the hard work
of getting started, it will be there to keep you moving.
When was the last time you lost track of time while doing something? Maybe
you were mixing a song on your computer. Maybe you were having a
stimulating conversation with a friend. Maybe it’s been different things at
different times.
Now imagine turning that activity into your work. Wouldn’t work be easier
and more enjoyable? Wouldn’t you be able to work longer and harder than
ever before?
I don’t want to create the fantastical impression that you can always be losing
track of time while you’re doing your work. Bringing your art into the world
is always going to be full of uncomfortable moments. Making your art is a
job, just like laying bricks or waiting tables.
But think how much easier it is keep yourself going when you’re curious
about something.
Lots of people write to me lamenting their “disparate interests.” They
understand that their own curiosity is powerful fuel, but they are afraid that if
they follow their curiosity, they’ll never do anything productive.
This is a very natural fear. Ian Leslie, author of Curious: The Desire to Know
and Why Your Future Depends On It, explained on my podcast that many
people resist their own curiosity because once we’ve reached adulthood,
we’re encouraged to exploit what we’ve learned. If you have a skill, Ian
explained, you can make money off that skill, but you won’t learn anything
new. You have to find the right balance between exploitation and exploration.

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I also used to worry whether I would find success by following my curiosity.
It was a lesson from Steve Jobs that helped me trust that it would all work out.
Many times during that first year of self-employment, sitting at the shallow
desk next to my bed, I watched the video of the commencement address Jobs
gave at Stanford in 2005. Every word of that talk gave voice to the feelings
that drove me to strike out on my own. It resonated so deeply with me that it
brought me to tears. That talk gave me the courage to keep following my
curiosity.
“Much of what I stumbled into by following my curiosity and intuition turned
out to be priceless later on,” Jobs said. He told the story of wandering around
his college campus. Because he had dropped out of college, he could drop in
on any class he wanted. So he went to a calligraphy class. He learned about
the details of drawing beautiful letters. “None of this had even a hope of any
practical application in my life,” he recalled, “but 10 years later, when we
were designing the first Macintosh computer, it all came back to me. And we
designed it all into the Mac. It was the first computer with beautiful
typography.”
I felt that, like Jobs, I was creating my own education by following my
curiosity wherever it led me. That first year on my own, I wandered from cafe
to cafe, searching for wifi, electrical outlets, and chai lattes. My hard drive
piled up with unfinished blog posts and mockups for apps. I remember many
dark nights, walking home from a sixteen-hour day in which I hadn’t made a
dime. The temperate air of San Francisco provided a fitting feeling for my
light jacket of satisfaction. But as my retirement savings dwindled, I often
wondered if I was getting off track. Maybe I should stick with one thing?
Whenever I worried, I would return to Jobs’s story. Every day, I was learning
something new. Even if I wasn’t finishing the projects, I was learning new
skills with each one. I was also learning what projects could ignite my own
curiosity enough to keep me moving, and which ones would quickly lose my
interest. It was better than playing Guitar Hero.
Curiosity is powerful fuel for motivation. But curiosity is also a competitive
advantage. That’s because curiosity will take you places where nobody else
can go.
It’s a crowded world out there. Sometimes it feels as if every good idea is
taken. But if you follow your curiosities, they’ll eventually converge into

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something completely original.
Even if you’re not the best in the world at any one of those curiosities,
chances are you’re the best in the world at your particular combination of
curiosities.
When I was a child, as I’ve said, I loved drawing.
One summer when I was in high school, my brother left his college computer
at home, packed in styrofoam blocks in a cardboard box. I took it out, and set
it up, and got on the Internet. Those were the days when Steve Case’s
America Online had these “10 hours free” CDs blanketing the U.S. I even
made my first web page on my AOL account.
At the time, the Internet and drawing had nothing to do with one another.
“Web design” was limited to making blinking text or plastering a website with
animated gifs of comets. But my interest in drawing led me to study design.
My interest in design converged with my interest in the Internet, and I
eventually started learning about web design. I was blogging what I was
learning along the way. A year after starting my blog, I got a job in Silicon
Valley, which was my first contact with entrepreneurship.
When I started my journey of self-employment, I kept Steve Jobs’s
calligraphy story in my mind. I did exploit my knowledge by doing a little
freelance work to pay the bills, but I still made sure to fill up as much of my
day as possible with exploration. I trusted that if I followed what I was
curious about, it would lead to something interesting.
After three years of experimentation, my biggest curiosities finally converged.
My first book, Design for Hackers, was born from a combination of my
interests in design, programming, entrepreneurship, and writing.
Yes, there were books out there about design principles. But they were written
for people who wanted to be graphic designers.
Yes, there were books out there about web design, specifically. But they were
written for people who wanted to be web designers.
Because I had experience as an entrepreneur surrounded by programmers, I
discovered a gap in the market: Lots of entrepreneurial programmers (who
affectionately called themselves “hackers”) wanted to learn design not as a
profession, but as another skill to add to their repertoires. They wanted to
understand what makes the design of their favorite apps beautiful and
functional, and why they struggled to get the same results with the apps they
were building.

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I had the knowledge, and I understood the audience. I could speak their
language, and I wasn’t just a designer and an entrepreneur – I had also spent
six years writing on my blog, learning how to communicate ideas in an
engaging and clear way.
When Design for Hackers debuted, it outsold the latest book by U.S. Vice
President Dick Cheney. It outsold The 4-Hour Work Week, by Tim Ferriss, the
author who had inspired much of my journey. It even outsold Eric Ries’s New