Barbara Winter: Making a Living Without a Job

When I surveyed a group of my newsletter readers about what they loved most about self-employment, the overwhelming majority said, “The freedom.”

• My work is no longer challenging. It’s time to do something creative. More and more restless souls are questioning the assumption that once they’ve been trained for an occupation or have acquired years of experience in it, they must do it for the rest of their days. Several years ago, a group of California environmentalists adopted as their slogan “Just Because You Can Doesn’t Mean You Should.” It’s an attitude that many are now taking about their work. Why, we wonder, should our lives be limited to a single occupation?

Dr. Cleve Francis would understand this questioning completely. After running one of the largest cardiology practices in Virginia, he’s now on his way to a second career as a country music singer. “When I started out in cardiology, I couldn’t wait to see the next patient,” he says. “Now there’s not that much excitement in cardiology. But I think that my music can bring just as much joy into people’s lives as pills and medicine.” It’s important to have the courage to act on your ambitions.

• I’ve spent the past ten years helping other people achieve their goals. Now I want to go after my own dreams. Barbara T. Roessner, writing about career changing in the Hartford Courant , has this to say: “There is a feeling that life outside the office has suffered, that what we have given up—time for our children, our spouse, ourselves—has not been worth the payback. If we have worked this hard for this long, should we not have more to show for it, at least in a nonmaterial way?” Knowing that you’ve helped someone else succeed in business is rewarding only when you have benefited as well.

Few jobs make it possible for us to pursue other, personal goals. The best interests of the company are frequently not in sync with your own, business or personal, and often can sabotage the furthering of your personal goals. “If only I had more time,” we sigh wistfully. Besides identifying your goals, you need time, the wherewithal, and the commitment to making them happen. No one else can do it for you.

• I’ve lost my job and haven’t been able to find another. After massive layoffs and downsizing, more of those who hadn’t previously considered self-employment are beginning to investigate. Some former jobholders are seeing their loss as an opportunity to try out an idea they’ve had for years. Others are discovering that once they start asking themselves if they could make a living in another way, they begin to be newly aware of services or products for which demand outstrips supply. Maybe, just maybe, they could be the one to fill the gap, they think. I frequently hear from folks who had been too timid to quit their jobs but once they were fired found the confidence to create something on their own.

My self-employed friends and I were horrified to see a newspaper story that declared, “Current job market forces people to consider self-employment.” Those of us who practice this way of working know that nobody succeeds if they think this is the last resort—a desperate measure. However, if you take the opportunity to explore alternatives to having a job, you’ll be amazed at the resources to help you every step of the way.

You’ll also start connecting with people who are facing change with optimism, people like Michelle:

Downsized for the third time, which has provided yet another opportunity to do those things that I love. The child in me is a little scared but the stronger entrepreneur in me is terribly excited about the possibilities before me. I have already tapped into people in my network for projects as a Personal Assistant, Personal Chef, and of course my own venture, Winning Proof. The 3 r’s define me: resilient, resourceful, and rewarded. Thanks to you, Barbara, I already have a running start.

Two days before I got laid off, a good friend told me that my way of thinking had outgrown having a j-o-b. It was an ah-ha moment that I wholeheartedly agreed with. Now it shall be put to the test, which I have no doubt I will pass—bad economy or not.

• I’m tired of working with negative people. Discontented coworkers can be toxic to your aspirations and your soul, and too many organizations are loaded with unhappy people who can ruin the finest career. A self-bossing friend of mine recently wrote about a visit she made to a teachers’ meeting where the teachers did nothing but complain about their jobs—and this was before school had opened for the year. An atmosphere of negativity can sap your energy and destroy your attitude and self-esteem. As a self-bosser you will find a new desire to surround yourself with healthy people who energize and encourage your efforts. Becoming self-employed connects you with a new cast of characters, people who are in your life by choice, not chance.

• My job pays me a good salary, but I’m miserable doing it. There’s got to be more. These days, if you mention dissatisfaction with your job, you’re bound to be reminded that you’re lucky to have a job. That only adds, of course, to the frustration of working at something you hate. Simply suspecting that life can be richer and happier than it has been can be a crucial starting point for exploring other options. In fact, dissatisfaction can be downright healthy if it leads you to positive action. Trust that your suspicions are correct and let your discontent be a catalyst for moving you in a new direction.

When I was a freshman in college, I took the requisite speech class my first quarter. Although I didn’t deliver any memorable talks, I enjoyed the class so much that I decided to make speech my second major. Shortly after I’d made this choice, I met my speech professor in the hall. Thinking he’d be flattered that his class had inspired me, I told him about my plan to get a speech degree. He smiled patronizingly at me and said, “You won’t like it.” I knew that he really meant, “You won’t be any good at it.” In that moment, my motivation shifted and I became more determined than ever. I was going to prove him wrong! That wasn’t, of course, the most mature reason to go ahead with my decision, but it’s been oddly satisfying. I approach every speech, every seminar, thinking, “This one’s for you, Dr. Meisel.” His unkind words may have been wiser than I knew at the time.

Whether your motivation is to spend more time with your kids or to see the world or to become the eccentric neighborhood inventor puttering around in your garage, becoming joyfully jobless can help you realize those dreams—and more. The time you spend now giving thoughtful consideration to your goals, your motivations, your priorities, will be valuable preliminaries to making specific plans. The best way to begin is by getting to know your new boss.

• What do you think is your primary motivation for wanting to be joyfully jobless? This question can be difficult to answer and, in fact, may generate different responses at different times in your life. Knowing what motivates you, however, can be helpful in making better choices for yourself. For instance, a woman I know would say she’s motivated by a desire to help those who are less fortunate. Observing her behavior shows that another factor is at work. When she is in a group, she has a strong desire to be the center of attention. Perhaps her true motivation is to receive recognition—albeit through helping others.

Look over the following list of possible motivating desires and check those that are true for you.