Meet Barbara Winter

Barbara J Winter is a pioneering self-employment advocate, writer and teacher who has spent the last twenty-five years pondering the question, “Why aren’t we all self-employed?” Helping others discover the Joyfully Jobless life is her favorite occupation. To readers of Read more


Buon viaggio….good journey. How nice to have you along. This blog has been a long time brewing. Hardly a day passes when I don’t come across a fascinating new business idea, inspiring story or useful resource and want to pass Read more


Barbara Inspiration Galore Join the Conversation!  

I make no secret of the fact that I’m in the midst of a love affair with Venice. It almost didn’t happen.

My first visit was decades ago when I participated in a whirlwind tour of Europe. We zipped through Venice, were escorted to a glass factory store specializing in selling over priced goods to tourists and whisked away.

I was not impressed.

It wasn’t until 1999, on a short stay with my daughter, that I began to uncover the charms of Venice. Suddenly I understood why artists, poets, writers and musicians kept returning for fresh inspiration.

In its’ heyday, it was a […] Continue Reading…

The Lucky Siblings Club

Barbara Inspiration Galore 2 Comments

Almost anytime I mention my siblings to someone who’s never met them, they smile and say, “You have the most interesting family.”

Although I think that my siblings are all fascinating people, I sometimes forget what a uniquely adventurous group we are. Until three years ago, getting together was a rare event that insured we were all on our best behavior when we congregate, but I think it goes much deeper than that.

Our siblings are, after all, the longest relationships most of us have. That shared history, no matter how good or how bad, lays a foundation that can’t quite […] Continue Reading…

Heart on Your Sleeve?

Barbara Inspiration Galore 1

Several years ago, I confessed to the participants in my Making a Living Without a Job seminar that I was mysteriously drawn to learning to play poker. A man, who looked as if he might have sat at a few poker tables himself, shook his head and said, “You won’t be good at it.”

I laughed and said I knew exactly what he meant. After all, when I was in high school my mother had warned me by saying, “Your problem, Barbara, is that you wear your heart on your sleeve.”

It was not intended as a compliment, of course.

Although I […] Continue Reading…

Building a Hothouse For Your Dreams

Barbara Dreambuilding 101 Join the Conversation!  

What many people fail to realize is that dreams are extremely fragile—especially in their early days. Dreams need to be nurtured and surrounded by support.

Here are a handful of easy ways to get your dreams off to a great start.

° Passion must be present. While a dream may be born in passion, it’s up to you to keep it alive. If you’re halfhearted and lukewarm about them, your dreams will never come true.

One way to keep passion high is to spend a few minutes every day visualizing the successful completion of your dream. How does it look, smell, taste, sound, feel? […] Continue Reading…

Creating Perpetual Prosperity

Barbara Dreambuilding 101 2 Comments

                     They’re your dreams; it’s your life. No one else is going
              to make things right for you. Only your actions can provide the
              kind of life you want.
                                                           Harry Browne

Marnie loves the symphony, but with a business in its infancy season tickets are a bit out of reach. That didn’t stop her from enjoying the full spectrum of concerts last year, however.

She became an usher at Symphony Hall and heard every note. In addition, she was […] Continue Reading…

The Best Day to Begin

Barbara Dreambuilding 101 3 Comments

Early last year, I got a request from Marianne Cantwell to participate in a video project she was putting together.  It seemed simple enough  when she first proposed it.
Marianne asked me and several others to answer in a sentence or two the question, “What do you wish you had known when you were eighteen?”

I began thinking about my eighteen-year-old self and realized that like most people that age, I was busily trying to figure out what I thought.
What kind of life did I want to have for myself? Was it easier to settle for an uninspired life or listen […] Continue Reading…

There’s Always a Way

Barbara Dreambuilding 101 1

Walter Swan was a 75-year-old retired plasterer and eighth grade flunk out who conceived a wild dream. For years Swan had entertained his wife and their eight children with stories about growing up in the deserts of Arizona. Although he could barely read or write, Swan had a dream of turning his memories into a book.

In 1951, he taught himself to type with two fingers and began writing down his stories. His wife corrected and retyped the book. Then Swan optimistically sent his manuscript to several publishers. They all turned him down.

Discouraged by the rejection, Swan packed the manuscript […] Continue Reading…

What Would You Trade for a Dream?

Barbara Dreambuilding 101 4 Comments

Several years ago, a television interviewer asked Sophia Loren the secret of her success. The actress didn’t hesitate for a moment. “I am successful,” she replied, “because I was willing to give up being anonymous.”

It appears that anyone who ultimately achieves their dreams has a clear idea what the trade-off was that was needed to accomplish it. It’s a characteristic often lacking in those who attribute their lack of success to bad breaks, circumstances over which they had no control or lack of money.

Money, in fact, becomes a popular scapegoat in stories about failure.

Most often, however, our dreams are […] Continue Reading…

From Miserable to Marvelous

Barbara Catch the Spirit Join the Conversation!  

I recently moved and came across the materials from a seminar that you hosted with Valerie Young in western Massachusetts. I found the Work at What You Love workbook and now I am living the life I wrote about then. I’m actually doing even more creative stuff than I could have dreamed of back then.

I remember that I loved the seminar but really was at a place where I thought the ideas would work for anyone but not me. I had very low self-esteem in the area of work because I kept choosing jobs that were a poor match.

This […] Continue Reading…

The Key to Having a Magical Life

Barbara Catch the Spirit Join the Conversation!  

Here’s another postcard from the field that caught my fancy.
I think so often in this world people think that being good at business is about being clever, but the thing about business is that it involves people—and people are interested in what’s in your heart.

I have worked at many different things, but one that gave me incredible insight was being a children’s entertainer. Children will automatically want to join in with whatever activity you want them to engage in as long as you look like you’re having a magical time.

If you are following your bliss, they will join in […] Continue Reading…

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