Going Long - Part 2

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.”

The Choice

Tsilli's story illustrates the real challenge that befalls almost everyone with the opportunity to make a major career change and go it alone: finding a way to build systemization into the business, and deciding what role the business will play in the rest of their lives. Sooner or later, every successful business owner — accidental or otherwise — faces a choice: Where are we going with this thing? As described throughout the book, many of the members of our group made a deliberate decision to stay small, creating a “freedom business” for the purpose of having the freedom. Others chose to grow by carefully recruiting employees and going all in.

Here's how three people faced this critical choice, resolving it in different ways.

Option 1: Stay Small

No one is truly a born entrepreneur, but Cherie Ve Ard probably comes close. Working on her own since she was twenty, she's now thirty-eight and has never looked back. Her father was also an entrepreneur, starting the family software business that Cherie eventually took over. The company develops custom software solutions for health-care providers. In 2007 she hit the road with Chris Dunphy, her partner, and they traveled by RV across America. Being on the road while running a software company led to an obvious expansion: Cherie and Chris started a side business making mobile apps.

Business is good, but Cherie has purposely declined to pursue a number of expansion ideas. Here's how she puts it: “Without a doubt, the smartest decision I made was to set a specific intention to not grow the business.

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