Going Long - Part 1

Going Long

Going Long

“Nothing will work unless you do.”

— MAYA ANGELOU

Among 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.

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