The Picket Fence Dilemma

Being an entrepreneur has its advantages. There’s flexibility, the ability to do work that aligns with your vision and values, the challenge of generating new business and balancing sales with service. Every day, an entrepreneur gets to choose what action steps she needs to take that day to meet her goals and objectives.

Being an employee has equal advantages. When you work for someone else, you have the satisfaction of being part of something larger than yourself and working with a team. While there may be politics, and no company is safe from change, working for a company typically provides stability that includes a steady paycheck, benefits and other perquisites.

What, then, do we do when we can’t decide between the two–entrepreneurship or employment?

Picket FenceI call this “The Picket Fence Dilemma.” You might also call it The-Grass-Is-Always-Greener Syndrome. People who are employed have wild fantasies about what it would be like to work for themselves. “Isn’t it great being your own boss?” people asked me when I left my job as vice president of marketing for a hospital to launch my coaching practice full-time. “Don’t you just love the freedom?”

“Yeees,” I would reply cautiously. How could I communicate the cost, and benefit, of being an entrepreneur? How could I tell people who are dreaming of bolting from a corporate cubicle that running your own business isn’t really being your own boss? Running a business is like having dozens of bosses, and they’re called “clients.”

When I work with career coaching clients, one of the first things we have to discern is which side of the fence they are choosing: employment or entrepreneurship. Getting a job and keeping it involves a host of skills and talents that are quite different from running a business. Choosing self-employment is not, I would venture to say, the easier choice. Gratifying, yes. Challenging for sure. But not easy.

The worst thing of all is to be on the fence about that choice. Whether you want to be employed or grow a business, choose. Pick a lane. Then give it all you’ve got. Otherwise, you’ll end up straddling that picket fence. And that’s gotta hurt.