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

Who Would You Want on the Train?

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An old adage says, “Tell me who your heroes are and I’ll tell you who you are.”  We all need living models of success—even if we have to look long and hard before we find those people who inspire us to do more and be more.

When we don’t  actively look for people who inspire us, we lose the capacity for genuine appreciation. That spills over into under appreciating our own gifts and achievements.

Whether you’ve got such a list of people or it’s time to start one, here’s a little exercise to help you pay closer attention.

For years I’ve been saying that my fantasy trip would be a very long train ride—perhaps across Canada—with a stack of books I’d been meaning to read. I decided to take that vision a bit farther and plan a dream trip aboard the Orient Express.

After a visit to their website, I chose the Venice—Prague—Paris route. Now I just had to fill up the train.

Who would I love to have with me? Why did I pick the ones I did? Take a look.

° My family—because we’ve already learned how to travel together peacefully.

° Anne Lamott—because she’s a rare combination of wise and funny.

° Bill Bryson—because he’s a brilliant storyteller who makes me laugh out loud.

° Richard Branson—because anyone whose motto is “Fun is Fundamental” belongs on this trip.

° Whoever writes the copy for Innocent Drinks because they’re wacky.

° Elizabeth Gilbert—because she might be ready for another trip and she speaks Italian.

° Billy Collins—because he turns stories into poems that I love.

° Paul McCartney—so I could gaze at him adoringly and he might give us a few tunes.

° Rick Steves—because he could fill us in on what we’re seeing.

° Alexander McCall Smith—because he’s one of the best storytellers writing today.

I realized as I was making out my list of fellow passengers that every one of them was selected because I wanted to hear their stories. I’d also love to eavesdrop on conversations between them.

You’ll also notice that there are no politicians or overexposed celebrities on the list. In fact, even though many of the passengers are quite well known (and McCartney more than well known), they each have a bit of mystique about them.

Imagine what five days on board with this group could be like.

If you were filling up a train or a yacht or a retreat center, who would you most want to have along?

Make out your list and then don’t be surprised if you find yourself in their presence. It might not be on the Orient Express, nor all of them at once, of course.

As it happens,  I’ve spent time with all but three of the people on my list—and I expect the others will show up in due time.

A Few Things I Didn’t Know 50 Years Ago

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I headed into my birthday week thinking it was time for a fresh inventory. As I was pondering this little project, I realized (once again) what a surprising life I’ve had. It certainly has exceeded my early expectations.

I played around with that a bit and began to wonder what my expectations had been fifty years ago. (No one is more startled than I am that I was an adult fifty years ago!)

Back in 1964, I was 22, newly married and in my second year of teaching high school English and speech. I was still living in the small town [...] Continue Reading…

A Simple Tool to Sharpen Your Focus

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If you are a reader of Joyfully Jobless News, this may be familiar.  When I came across it again the other day, I decided it was worth a second visit. This simple idea has added enormously to my productivity and fun.
The sky was overcast and the wind was frigid, but there we stood huddled together with hundreds of others for three shivering hours. It was our second day in Amsterdam and we were in line to see what we had come for—the Van Gogh Museum.

My siblings and I had been planning this trip for months. Hundreds of emails hammered [...] Continue Reading…

Your Mission, Should You Choose to Accept It

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The message I got about work when I was growing up pointed out that there was good work and bad work. Good work meant you didn’t have to sweat.

Nobody mentioned that sweat-free work probably would involve sitting at a desk all day doing repetitive chores.

It wasn’t until I became obsessed with the role of work in our lives that I began to challenge such limiting notions. Eventually, I came to think that the best work called us to use our minds, bodies and spirits.

That, of course, is also why the concept of having multiple profit centers appeals to so [...] Continue Reading…

Cost or Contribute?

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Life often seems like an endless series of decisions to be made. Chai latte or decaf Americano? Take a walk or sit at the computer? Plant roses or zinnias? Start a business now or wait until you get fired?

Given the fact that we are called upon to make decision after decision everyday, it would seem reasonable to assume that most of us would have given thought to how we make decisions. We’d have our own decision-making tools that we could employ when needed.

If we l lack such tools, too many decisions are simply based on habit. (Chai latte yesterday, [...] Continue Reading…

Why Self-help Doesn’t Help

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Last week I wrote an article for the upcoming  Winning Ways newsletter and mentioned that I’m not fond of the term self-help because it ignores the fact that it’s not truly a DIY project. It involves a teacher as well.

No matter what we call it, not everyone is getting the kind of results they anticipated. Here are some thoughts on how we can make the most of our personal growth excursions.
When I first discovered the literature of personal growth and development, there weren’t many titles to choose from. Today there are thousands.

I always have a self-help book or two [...] Continue Reading…

Listening to a Wise Man

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During the years that I lived in Santa Barbara, I always looked forward to the annual writer’s conference. Although I never attended the entire program, I often showed up for the evening talks given by successful writers.

The highlight for me was opening night when the legendary Ray Bradbury was the conference kick-off speaker. He was so popular that he held that distinction for years.

Members of the audience were often treated to personal information such as the fact that he refused to travel by air and would only go places that could be reached by car or train.

It was also [...] Continue Reading…

13 Ways to Take a Creative Excursion

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Julia Cameron calls them Artist’s Dates. Sarah Ban Breathnach calls them Creative Excursions. Whatever you call them, they are worth making a regular event in your life.

“The Artist Date need not be overtly artistic,” says Cameron, “think mischief more than mastery. Artist Dates fire up the imagination. They spark whimsy. They encourage play. Since art is about the play of ideas, they feed our creative work by replenishing our inner well of images and inspiration.”

The purpose of such solo events is to take time every week to make a visit to a new place to gather ideas or just [...] Continue Reading…

A Step Back

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When Marla decided she wanted to leave her high-paying corporate job and start a small business, she feared it would be difficult to convince her musician husband of the wisdom of her plan. She carefully outlined her vision to him and waited for his response.

He considered what she said about living on a tighter budget and rearranging responsibilities and then replied, “Oh, so you’re saying we’ll move ahead by going backwards first.”

His insight is one that many people, unfortunately, lack.

But almost every dream worth going after demands a willingness to step back. That step can take many [...] Continue Reading…

A Short Story About a Long Success

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On July 15, 1993, I woke up feeling excited and apprehensive. The cause of this emotional turmoil had been years in the making. It was publication day for Making a Living Without a Job.

I had spent much of the previous year writing and rewriting and writing some more. But the story truly began decades earlier when I set out on my own rather lonely journey in self-employment.

My experience was very much like Paul Hawken’s who said, “When I started the natural food business in Boston, my business knowledge was scant. I did the best I could and began reading [...] Continue Reading…

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