How to Know When It's Time to Strike Out on Your Own

Seven Criteria to Consider Before You Leave Corporate Life

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My heart ka-boomed as we prepared to sign the lease. I turned to my business partner, Jean Robaire, and said I couldn't go through with it. In that summer of 1998, the $2,000-per-month lease was higher than my salary had been only three years earlier.

Jean had an extraordinary business track record. I'll never forget his words: "I know how you're feeling. But if you want to be successful, you'll have to get used to this feeling. This is risk. And if you ever want to take big steps in your career, you'll have to get used to risk."

Needless to say, we signed the lease. Robaire & Hogshead was born, and with it came my first step in a career of running my own business.

I soon learned that working for yourself isn't quite the sexy gig it appears. Suddenly the bills arrive in envelopes with your name on the front. There is no benevolent "sick-day policy" that covers your salary when you can't work -- and no health insurance, for that matter.

Yet there are some nifty rewards. By working for myself, I can handpick the best opportunities in freelance copywriting, corporate speaking and innovation consulting.

But back to you. Your decision to strike out on your own can't be based on a temporary "Screw you people, I'm outta here!" mood; it must be a carefully considered business decision.

That said, if you meet all or most of the criteria below, it might be time to turn away from the milky, warm teat of corporate life:

1. The entrepreneurial flame burns within.
You feel a need to fulfill an ambition to create and develop something of your own. You're willing to roll the dice, staking yourself on the bet.

2. You're ready to live or die your own rules.
You've been frustrated and limited over the years, feeling forced to march in lockstep with hierarchical structure.

3. Your talents and skills demand new challenges.
You want to grow into a new area, such as branded content, and you're finding that a traditional agency can't give you that opportunity.

4. You can subsist without a steady income.
Running your own place means that you might have to pay employees out of your personal checking account.

5. You have a sugar-daddy client.
Ideally you'll have a client waiting in the wings, ready and waiting to hand their account over to you.

6. You have a sturdy stomach and appetite for risk.
You can balance the terror of an un-ringing phone with the grunt work required to make it ring.

7. You can exit without burning bridges.
Otherwise the stench of smoky ash will follow you wherever you go.

You can always go back to agency life. What you can never return to is a time when you wished you could create a company -- and your own career -- on your own terms.
Sally Hogshead is a freelance writer and a professional speaker for companies. Read more at
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