Joyfully Jobless: An Interview with Barbara Winter

A couple of years ago, a friend of mine told me about a book titled Making a Living Without a Job: Winning Ways For Creating Work That You Love by Barbara Winter. That book literally changed my life.

As I started reading the book, I got excited and by the time I got to the fifth chapter, I was so pumped I decided to leave my job. So, when I started this blog, it was a natural for me to want to interview Barbara, but I wasn’t sure how she would respond to it.

I was hesitant to ask her for an interview, specially with my blog still in the formative stages. But if there was one thing I learned from reading Barbara’s book, it was to make a decision and take action. So, I sent her an e-mail explaining my intention to interview her. She responded with an open willingness.

After giving the matter some serious consideration and forming and reforming the questions, I finally sent her a list of 10 questions and held my breath. Soon enough I received an email from her acknowledging the receipt of the question and praising me for asking good questions. Wow! I was flying high now.

What was really surprising to me, was the fact that despite her busy schedule, which she had mentioned to me earlier, and despite the fact that we were getting into the Holiday weekend here in States, I got the answers back the very next day.

Thank you, Barbara. You Rock!

1. As I understand, you have been living life on your terms for quite some time now. What does that entail for you?

For me, this has really been about figuring out the kind of life I wanted to live and then making it happen. For instance, I realized into my second experience working for someone else that I wasn’t very happy being an employee. I also had always dreamed of living in different places and it wasn’t until I got the idea to start my own business and run it from home that I realized I could live anywhere I wanted. Surprisingly, I figured that out long before we had the kind of technology we have today that makes it even easier to be mobile.

2. How did that all come about, and how long ago was that?

I started my first business when my daughter went off to kindergarten. This year her daughter starts school, so my entrepreneurial life has spanned over three decades. When I started out, I didn’t know another soul who worked from home and went to great lengths to conceal that. It was years before the Homebased Business Movement got to be trendy.

3. Did you face any fears or concerns about leaving a steady paycheck behind, and if so, how did you overcome them?

Not really. I had read a wonderful book called SUPERGIRLS: The Autobiography of an Outrageous Business that so inspired me I didn’t doubt that I could create income on my own. Of course, that also led me to explore my relationship with money and all my unhelpful beliefs around it.

4. For those wanting to get started today, to become what has been termed as Location Independent, or what you would refer to as Joyfully Jobless, what advice do you have for them?

First of all, I’d have them memorize my favorite line from Rumi: “When setting out on a journey, do not seek advice from someone who’s never left home.” Getting rid of employee conditioning is one of the trickiest bits, but there are so many generous writers, bloggers, seminar leaders who are willing to share what they’ve learned. Connecting with others who are self-employed is essential. It’s also essential to do your own homework, read books, attend classes and be willing to take responsibility for your own growth and learning.

5. I love that term “Joyfully Jobless”. Tell us how did that come about and what it means to you personally?

Years ago, I was being interviewed by a reporter from the Hartford Courant and in response to a question she asked, I called people who were working on their own Joyfully Jobless. I had never even thought those words before; it just came out. I think she used that in the headline and it stuck. To me it’s about more than not having a job: it’s equally important to create a livelihood that engages your spirit and creativity. Just working for money is working for the booby prize.

6. What are some of the benefits of becoming Joyfully Jobless as you see it?

I wrote a list of 29 Things to Love About Being Self-employed and I find new things to add all the time.

A couple of years ago, I did an informal poll and the vast majority of those answering said that “freedom” was the biggest reward. For me, it’s also the thrill of creating something that didn’t exist and wouldn’t have been done in exactly the same way as I would do it. And a huge bonus is connecting with other passionate self-bossers who are curious, creative and adventurous. They enrich my life immensely.

7. Would you be kind enough to share your favorite memory of an event or a happening, that you believe may not have been possible had you not decided to become Joyfully Jobless?

There are so many. I spent 10 days in London and Rome this spring and since I was doing a couple of seminars in London got to meet new folks who are eager to make a living without a job. But it also is a treat to get paid to travel and do what I love. For years I longed to travel and could never scrape the money together (when I had a paycheck). Now I regularly travel to great places and am nicely compensated. And, of course, I never have to get permission to take time off when something important happens like the birth of my grandson a year ago.

8. What are some of the remarkable places you have visited over the years?

I’m a longtime Anglophile so working in the UK has been a treat. I am madly in love with the Lake District where I’ve taught a couple of retreats. And my other mad love is Italy, especially Venice and Tuscany. I also have enjoyed visiting many great cities and their museums in the US and Canada. I’ll be doing a retreat this fall in another of my favorite spots, Sedona, AZ.

9. If you were to start today, I mean if you were in the same place where you were back then, what are some of the opportunities available today that you would take advantage of?

When I sat down and wrote out a list of what I most loved, it included “talk, travel and read books.” I’d still have the same list. The biggest difference today is that we can communicate so quickly and connect with people in far-flung places with more ease. So I’d still do the same thing, just use different tools.

10. Thank you, Barbara. You have been so kind and generous with your time and expertise, I sincerely appreciate it, as I am sure the reader’s of this blog will as well. Do you have any final thoughts for us?

There’s a wonderful quote from Sir Richard Branson that I love. He says, “The world is a massively more hospitable place for entrepreneurs than it was twenty years ago.” It’s also massively richer in resources. Finding the inspiration is the real starting point, however.

Once again, thank you, Barbara, you are a gem.

Barbara has a revised and updated edition of her book available here.

Please visit her website and subscribe to her Buon Viaggio Blog.

Note: I corrected my misquote of Barbara’s Brand, “Joyfully Jobless”, for which I had originally used the words Joyously Jobless. My appologies for the error.

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