Leaving the Corporate World: 4 Lessons to Know Before You Leap

Marisa Torrieri

leave job riskIn today’s “Lean In” culture, we’re encouraged to climb the corporate ladder, bust through glass ceilings, and achieve our executive dream jobs.

But what if—after rising to the top of your field, complete with a fat salary—you find yourself fantasizing about leaving it all to strike out on your own?

Even those of us who haven’t jumped ship certainly have pondered the idea on an idle Tuesday—which is why we asked two former corporate workers who struck out on their own, then came back to the mother ship, for lessons they learned in the process.

In the late nineties, Gail Silverman, a now 49-year-old MBA, landed the perfect job in NYC: marketing director for daytime programming at a major TV network. Her nearly six-figure salary allowed her to do and buy many things. Yet the Renaissance woman always yearned for more time for two of her passions: music and yoga.

So when the company decided to move her position to the West Coast, she took a $30,000 departure package so she could stay put, hoping that she could make money as a freelance marketing contractor while ultimately turning a profit by doing something related to music.

In 2008, after several up-and-down years of balancing bread-and-butter, contract-based freelance marketing work with music-related pursuits (including the launch of Girls Rock & Girls Rule, a nonprofit organization devoted to promoting women in rock ’n’ roll), the economy started taking its infamous downturn. And while Silverman had generated a lot of buzz for that venture, not to mention her own recorded music, she started seriously considering going back to corporate life.

“I was doing it for the love of it, but the hope was that it would become something sustainable,” says Silverman. “Starting in 2008, it became hard to pay the bills.”

Call it the “Eat, Pray, Love” fantasy: While there isn’t an exact figure, it seems anecdotally that hundreds, if not thousands, of men and women, like Silverman, leave salaried positions to launch independent ventures. And while some are successful—and even write books about it—many, if not most, are not.

For those who are still eager to take the risk, here are four essential lessons learned from those who made the leap, and didn’t achieve the success they’d envisioned—so you don’t follow in their footsteps.

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  • Ashley

    I agree. As someone who is about to go out on their own for the first time, it’s really scary but a solid plan and a lot of savings make a gal feel a bit more secure.

  • Lynne R

    Great Article.