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

Would Winning the Lottery Make a Difference?

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On the morning of August 25, 1997, the big story on the morning news shows was the Powerball lottery drawing happening that evening. For the first time ever, a lottery jackpot had reached the $300,000,000 mark. Lines were forming outside convenience stores, people were planning a lavish future. A mathematician assured the Today Show interviewer that someone would absolutely win based on the finite combination of numbers..

Although I’m not a lottery player most of the time, I decided that if I didn’t buy a ticket or two I’d miss the excitement when the drawing rolled around that evening. I purchased five tickets, I recall, and didn’t give it further thought until the big moment.

Sitting in front of my television, I laid out the tickets and began checking them as the numbers were called. One of my tickets matched the first number drawn. Then the second, the third, the fourth, and the fifth. Then the Powerball number was called and it wasn’t a match for me. I thought I was going to throw up.

Several minutes later, I called my friend John, a regular lottery player, to share my trauma. He commiserated with me and then cheerfully pointed out that I had won $5000. Moments earlier, I had lost $300,000,000. Now $5000 felt like a huge windfall.

The next day I drove to the Minnesota Lottery office and claimed my prize. I was giddy.

I had my picture taken holding a gigantic check with my name on it. I promptly deposited the actual check into my sabbatical account. Less than two years later, I was enjoying eight months of travel and discovery. Traveling first class would not have enriched the experience one bit.

I hadn’t thought about this little episode until a month or so ago when someone reminded me of it. “Do you ever think about how your life would be different if you had won all that money?” he asked. I told him that I hadn’t ever done that and couldn’t imagine that I’d be doing anything other than what I do now. He seemed skeptical.

Honestly, I hadn’t told him the truth. I had considered what winning that money meant and realized that had I become the recipient of this huge fortune, my time would have shifted to being a full-time money manager. But that wasn’t the worst part of it. How could I have maintained any credibility in helping folks become self-reliant and self-employed? I would have forfeited my platform.

One of my all-time favorite episodes of the Actor’s Studio is the one with Dustin Hoffman. At the end of the show, a student asks him what he would be doing if he wasn’t a movie actor. Hoffman teared up and gives a passionate answer (which I’m paraphrasing here.) He points out that his movie career, while bringing him fame and fortune, was a bit of a fluke. If that hadn’t happened, he says, he’d be teaching theater in a college in the northwest or acting in community theater somewhere in the country. “I cannot not do this.”

It’s a sentiment echoed by Elizabeth Gilbert who points out that while the success of Eat, Pray, Love was thrilling, she would be equally devoted to writing had it not happened.

Could it be that it’s not about size, scale or success? Could it be–at least in the well-lived life–simply about the doing? You don’t need $300,000,000 for that.

A Holiday Suggestion

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Facebook reminded me of this post from three years ago. I think it is equally valid this year.

I’m pretty sure I broke out in a big grin this morning when novelist Jonathan Odell posted a link on Facebook to an interview with him that appeared in today’s Huffington Post.

Of course, I’m always delighted when someone I know is bringing their dreams to life, but this particular dream is one I first encountered when it was a tiny gleam in Jon’s eye.

I’m not certain that I was the first person he’d shared this with, but years ago he told me […] Continue Reading…

Inspiration at Your Fingertips

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When it comes to inspiration, we must invite it in—and seek it out. The more aware you are of the things you find inspiring, the easier it is to tap into those sources.

Don’t wait until you’re feeling stuck or frustrated or cranky before you get a lift.

Inspiration is highly personal so know what feeds yours.

Here are some simple ways to help you live from an inspired place.

° Practice meditation. Practicing meditators tend to have better access to their inner fountain of wisdom and inspiration.

° Build a small collection of movies that you find inspiring and visit them from time to […] Continue Reading…

Do You Use This Power Tool?

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Recently I got an email with a familiar question. It said, “Your book is brilliant. Is there an update planned?”

I wrote back explaining, as I always do, that Making a Living Without a Job is about philosophy, not how-to, and updating isn’t necessary.

Upon further consideration, however, I realized that Winning Ways newsletter really is an on-going update to the ideas in the book.

Are you a candidate for this bi-monthly publication?

Here are some signs that it would be a perfect fit for you:

You’re interested in new resources and stories that inspire.

There’s room for one more on your cheering squad.

You sometimes […] Continue Reading…

Ready to Accomplish More?

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When I first became a practicing goal-setter, I wasn’t very successful. I’d write down big goals and then have no idea how to even begin. Eventually, I made a discovery that seems so simple I didn’t believe it would work—until I tried it.

It now is firmly established as my most dependable operating system. It starts with picking a number, any number.

You don’t have to be a math whiz to put numbers to work for you. Assigning a number to a project can help you focus and, also, give you a finish line.

Open-ended goals have a way of never reaching completion, […] Continue Reading…

Time for a Creative Excursion?

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Julia Cameron calls them Artist Dates. Sarah Ban Breathnach calls them Creative Excursions. Whatever you call them, they’re 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 away regularly to visit a new place, gather ideas, or just feed your soul. Although it’s […] Continue Reading…

Do Talk to Strangers

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Author Bill Bryson talks about being on a train and thinking about fellow travel writer Paul Theroux who wrote about fascinating conversations he has with strangers. This perplexes Bryson because he finds it difficult to strike up conversations with traveling Brits.

That got me thinking about a conversation I had with an enthusiastic traveler who wondered how I managed to open a dialogue with someone I’d just met.

Since my Do Talk To Strangers Policy is a vital component of traveling—and being entrepreneurial—I started to consider how I actually go about it. I realized that some of it is purely intuitive.

For […] Continue Reading…

Building a Hothouse for Your Dreams

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Dreams are extremely fragile—especially in their early days. Dreams, like babies and seedlings, need to be nurtured and surrounded by support.

Here are a handful of 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? Allow that vision […] Continue Reading…

Musing on Motivation

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Those of us who write with the intention of motivating others, constantly deal with an enigma. What, for goodness sake, does the word “motivation” really mean?

My thesaurus lists all sorts of possibilities including “tempt, seduce and bribe.” That’s hardly what I had in mind here at Buon Viaggio.

After years of thinking about this word, I’m still not certain that I have a clear definition myself. I do, however, know what it means personally.

Motivation to me is when an inner force is moving me in the direction of an outer result. I also know that it needs to be nurtured […] Continue Reading…

Change of Plans

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So here’s how my week has started. Got up to an email that involved a change of plans for a fall seminar.

My daughter and her family left for a two-week road trip. The road they were planning to take is closed due to a bridge collapse. They rerouted themselves, but forgot to leave a housekey for the sitter.

Fortunately, I have a key to their house and live close by so delivering it was not a big deal.

However, this has me thinking, yet again, about how flexibility is a valuable stress management tool.

This is not something that comes easily for […] Continue Reading…

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