Barbara Winter: Making a Living Without a Job

Comedian Jon Stewart said, “The big break for me was when I decided this is my life.” This new epidemic of self-employment is being driven by an increasing awareness that we can all create our own big break. In an economic climate that teeters on uncertainty, thoughtful people are seeking fresh options—options that honor their creativity, add meaning and purpose to their lives, and allow them to go as far as their imaginations will permit.

While the Internet and other technologies have opened the door to self-employment for many, the basics of being joyfully jobless haven’t changed at all. Nevertheless, this updated edition will show you how to integrate the basics with new tools and resources.

If you are ready to stretch your mind to the idea of making a living without a job, you’ll find plenty of encouragement and practical information here. Designing a lifestyle for yourself that nurtures and supports who you are and what you value won’t happen instantaneously, but this book will certainly make the process simpler and easier. Becoming joyfully jobless begins with a commitment to self-discovery, a curiosity about your potential, and a willingness to acquire the information and skills that will enhance your work. Your way will be unlike anyone else’s, although you will share a deep camaraderie with others on this path. Being your own boss is both heady and humbling, but it’s seldom boring.

The joyfully jobless who make a living without a job defy easy descriptions and pigeonholing. Ours is a lifestyle that’s full of paradoxes. We have gone beyond being employees, but we’re not conventional entrepreneurs. Our bottom line is measured by our character as much as by our profits. The joyfully jobless often pursue lines of work that make a difference to the rest of the world, that are more than just a way to earn food to eat and a roof over our heads. We see our business as a natural extension of who we are and what we love to do. We have spent time and energy exploring and understanding ourselves so that we could find ways to earn a living by being ourselves. Some of us think of ourselves as working artists of life, although our work may not fit traditional concepts of artistic endeavor.

You’re going to meet some wonderful people on these pages. Keep in mind that wherever you are in your journey, these folks have already been there. They’ve made it over the wall and they’re eager to have you get over too. There’s a party going on on this side, and you’re invited!

No matter why you’ve decided to consider making a living without a job, you’ll find enthusiastic support in the pages ahead. I’d like to suggest that you read this book with pencil or highlighter in hand. (You do own this copy, don’t you?) Jot down ideas as you go. Notice, too, that you’ll find exercises at the end of each chapter that you can work on when you get to them or come back to after you’ve finished the book.

I’m delighted to have you along.

When I answered the phone, I was startled to hear a man whispering, “Hi, this is Scott. I’m calling from work, but I had to talk to you.”

“Sure,” I said.

“I want to be JJ,” he whispered back.

“Jay Jay?” I thought. “Who’s Jay Jay? Why’s he telling me this?”

Before I could ask, he went on to explain that he loathed his job and longed to be “joyfully jobless.” We made an appointment for him to call back when he could talk out loud.

Scott’s not the only one, of course. One memorable message arrived in my email box with the title “Cowering in my cubicle.” Every day I hear from people who have come to the same conclusion. Some have no idea what they want to do instead of having a conventional job. Others have an idea but don’t know how to get started. And recently, more people who find themselves without a job are looking at alternatives and options they may not have considered before.

My own journey began when I was in the midst of a second career and found myself as miserable as I had been in my first job. Ironically, I had landed a position as a job counselor, working for the Minnesota Department of Employment Services. Shortly after arriving there (and already realizing I was not cut out to be a bureaucrat), I discovered a gigantic book called The Dictionary of Occupational Titles. This book contains tens of thousands of job descriptions. “Surely,” I thought, “if I read this book, I’ll find my lost career.” In any free moment, I’d grab the dictionary and begin reading. The more I read, the more discouraged I became. “There’s nothing here I want to do,” I lamented. I feared I was doomed to a life of drudgery.

That’s not how my story ends, of course. I discovered that I could create my own work, be my own boss, and eventually get paid generously to do the things I loved. Along the way, I made wonderful new friends and plenty of mistakes. There were moments when I thought I had taken leave of my senses—and many more moments when I could hardly believe my good fortune. What I never imagined back at the beginning was that I’d end up teaching thousands of people how to leave behind the nine-to-five world and start building something on their own.

Of course, the people coming to my self-employment seminars and teleclasses bring plenty of questions with them, but the one I get asked the most seemingly has nothing to do with making a living without a job. The most frequently asked question I’ve ever received came after I relocated three years ago. “Why did you move to Las Vegas?” is the one I hear over and over.

The runner-up is “Do you actually think anyone can be self-employed?” Almost always, the person asking the question sounds shocked or at least skeptical. I have several answers to the first question, but my usual response to the second has been “Yes, I think anyone can be self-employed, but not everyone will be.”

As of this writing, there seems to be another topic that’s grabbed everyone’s attention: the current and confusing economic recession. Everything, from news stories to personal decisions, seems to be filtered through this growing crisis. So, of course, the question I’m hearing more often these days is “Isn’t this a dangerous time to start a business?”

That’s certainly a fair question, and I can answer it as only a Las Vegan might: “Have you considered the odds?” Unlike the rest of the world, here in Las Vegas our casinos boldly post the odds, warning that they’re not in your favor if you’re about to gamble. That doesn’t deter folks who hope to beat those odds.

One of the common assumptions about self-employment is that it is intrinsically risky. I’d like to suggest that you think about the odds of success if you are making a life change. How do you calculate odds? Not being a gambler myself, odds weren’t something I gave much thought to until I was fretting about the possibility of a giant calamity, such as being devastated by an earthquake or some natural disaster. I mentioned my qualms to my sister Margaret, who calmly asked, “Don’t you know the odds are always in your favor?” I was startled by that answer and shook my head, so she explained further, “Haven’t you noticed that even in large catastrophes, more people survive than don’t?”