3 Keys to Leaving Corporate America

It didn’t take the first time I tried. Not really.

After 20 years as a Fortune 500 executive and being “the first woman everything,” I achieved all that I set out to in my career. Yet I wasn’t happy. Turns out I was living someone else’s dream and not my own. It took a 2-year stint as a Peace Corps Volunteer about 15,000 miles (and several centuries) away in Papua New Guinea to learn that lesson.

Upon my return I embarked upon my first start-up — WebMD. It was a good one, at a wild time. Remember 1999? Dotcom heaven. I loved it until a management takeover when the founder parachuted out goldenly. Then it became just another politicized Big Business with little care for anybody outside its inner circle and anything other than quarterly earnings. It was also decidedly unfriendly towards women. It was no longer the sort of place someone with an entrepreneurial spirit could thrive.

So I exited. Departed. Ejected.

Not knowing what I would to do next (yeah, I pushed that big red button without thinking about next steps), I asked family, friends and business associates what they thought I’d be good at. The consistent theme was that my broad business background could help smaller businesses.
 Small businesses? Initially, I didn’t think “Small Business” was “big” enough for me. Then I began looking at the statistics, and they blew my mind: 90% of all U.S. businesses have fewer than 20 employees; 96% of U.S. businesses have fewer than 50 employees; 99.7% of all U.S. businesses have fewer than 500 employees and are “Small Businesses.” I had totally drunk the corporate Kool-Aid that the sun rose and set before Wall Street and the Fortune 500. But I was about to get re-educated.

So I began my own small business helping other small business owners. I’ve become a Small Business Evangelist. My specialty is advocating for women entrepreneurs. We face a different kind of uneven playing field than we experience in corporate. Rather than corporate women competing for the same rarefied c-suite office, we have supportive women entrepreneurs who want to see each one of us succeed. We battle together against entrenched cultural biases that can make this tough. My mission is to help other women who find Corporate America not a good “fit” transition successfully into what IS a good fit.

Unfortunately, I Made Every Mistake in the Book

When I left Corporate America, I wish I’d known some key learnings before landing outside the Never-Neverland atmosphere of Big Business. First, it takes a lot longer than you think it will to start-up a business from a standstill. Moral: Begin thinking, planning, and executing before you press the eject button. 

Second, the business you start will rarely be the one you end up with. Iterations — FAST iterations — are key. You’re not failing — you’re learning! It’s about customers, market research, responsiveness, and revisions. Your persistence and nimbleness are invaluable traits.

Third, “plan” is not a 4-letter word. It is difficult to plan too much, unless it paralyzes you. In my experience with business owners, the converse is more often true. According to most small business owners, “planning” :

●   Takes too much time
●   Is in my head!
●   Won’t help my business
●   Is too hard
●   I don’t know where to start…
(and by all means fill-in your own blank)

With your corporate experience, it is less likely that you will fall into these traps

3 Keys to Leaving Corporate America – Three Things You Can Do

As you begin your journey:
1) Paint the picture of your dream. Write down your destination; it will change.
2) Build a business plan you can use as a working tool. A business plan doesn’t have to be long. And having one will help forestall problems, cut your anxiety, improve your profitability, enhance management of your business, and permit funding.
3) Find a tribe of other women entrepreneurs to accompany you and cheer you on.


  • Renee Walkup

    Coincidentally, 20 years ago, I left my senior executive corporate job and started my own business, too. There have been many ups and downs in 20 years, including 3 “minor” recessions and a MAJOR one, too. What I have learned is that when you have a passion, and are good at what you do, the work/money/excitement all converge. Not everyone will like me. Not everyone will like you. But as women, we need to learn to get over that reality. I’ll bet Mother Teresa had her share of detractors, too. Focusing on what I do best, reinventing my business when necessary, and networking my butt off, have served me well. To all of you new “Fugees”, you’ve got what it takes. Good luck!

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