BECOME AS BIG AS YOU WANT TO
BE
(AND NO BIGGER).
“Nothing will work unless you do.”
—MAYA ANGELOU
A
mong the people we’ve met in our story thus far, a few are active risk
takers, charging ahead to storm the castle, career or finances be damned if
they fail. But far more common are those who carefully take the time to
build a business step by step. It’s a myth that all those who choose to go it
alone are Type A motorcycle riders, betting it all on the success or failure of
one project. Entrepreneurs are not necessarily risk takers; it’s just that they
define risk and security differently from the way other people do.
Tsilli Pines, an Israeli-American designer who now lives in my
hometown of Portland, Oregon, exemplifies the group of cautious
entrepreneurs. Over the course of eight years, she crafted a business making
ketubot, custom-designed Jewish wedding contracts. During most of that
time, the business was a night-and-weekend project she worked on after
coming home from the design studio where she was employed. With a
regular paycheck from the day job, Tsilli felt safe experimenting with the
business and learning as she went along. She also noticed an important side
benefit to working this way: With limited hours to spend on the business,
she had to make them count.
Thanks to referrals from happy couples, the business grew slowly but
steadily, with more orders each year. Each ketubah was a labor of love,
priced at $495. As 2009 drew to a close, Tsilli felt prepared to make the
leap. She gave notice to her boss and colleagues and prepared to go full-
time. This was it! She had jumped!
Except … the view on the other side wasn’t all she had expected. The
first week of freedom felt great; the second week she began to wonder,
What do I do all day? “I underestimated the value of having some work that
was collaborative and not self-directed,” she said. Over the next few
months, the business earned less than expected. Orders were still coming in
and the situation was far from desperate, but Tsilli felt trapped, drained of
the creativity she had thrived on while starting up.
“The all-or-nothing paradigm was too much pressure,” she continued.
“I’m running a creative business, but it’s a creativity killer for me to define
my whole income on the need to continuously deploy my creativity.” It was
a hard decision to make, but six months after leaving the design firm, she
approached the owners with a proposal: How about coming back part-time?
They said yes and were happy to have her.
Moving back to the studio three days a week was the right fit. When she
had left six months earlier, she had a lot of responsibility as the lead
designer; there was no way she could stick around in a lesser role without
first leaving for a while. Coming back in under the radar gave her the
security of having a certain amount of fixed income while retaining the
freedom of working half-time on her other projects. Also, Tsilli now
worked as a contractor instead of an employee, and that gave her an
unexpected but important sense of still earning all her income “on her
own,” with roughly half coming from the studio and half from her business.
It was right for her to leave, and it was right to go back. The business is
still profitable, but without the pressure of needing to rely on it exclusively.
Tsilli summarizes it like this: “The feeling I have is that I’m still laying
brick after brick. The different pieces interlock, and over time they may
build to critical mass. But right now I’m in a good place.”
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