How to support your wanderlust by Barbara Winter

Today I’m bringing you the inspiring Barbara Winter, author of ‘Making a living without a job’ and  also the publisher of ‘Winning Ways’ the longest running self-employment newsletter. She has been inspiring us all to become creatively self-employed, but like me she’s also hugely passionate about Italy and in her article she suggests ways to fund your wanderlust and make that trip to Italy a reality! You can find out more about her on


I grew up in a small town in southern Minnesota where an annual trip to the State Fair in St. Paul was the popular idea of travel. I had other ideas. In fact, I’m quite certain that wanderlust is in my DNA so I unless I found a way to include travel in my life, I was doomed.

Years ago, I read a book that contained this sentence: “For her, crossing the ocean was like crossing the street.” The moment I saw that, I knew I wanted that for myself. I wanted travel to be a regular activity, not a source of frustration.

Over the years, my plans for having an adventurous life were going nowhere. I considered becoming a flight attendant, hoped to win a trip in a sweepstakes, and attempted (unsuccessfully) to save money for a trip. Seeing a plane overhead brought me to the verge of tears, but nothing I did seemed to get me any closer to my vision.

That all changed when I sat down to write out my goals at the beginning of a new year. One of those goals was, “I am going to London.” Then I startled myself by adding, “And it will be a gift.” Since I’d never received such a gift, that seemed a stretch, but I left those words on the list.

Even though I had no idea how this was going to happen, I decided to get ready. I invested in a London travel guide. Then I got really bold and decided to get my passport. At the time, that seemed like a crazy extravagance, but I put it on my bedroom dresser so I’d see it as soon as I awoke in the morning. I’d smile and remind myself that I was prepared to receive a free trip.

Months passed and I continued my preparations. One day in October, I got a call from a friend and after we’d spent some time catching up, she said, “Oh, Barbara, I’ve been meaning to ask you. Do you still want to go to London?”

I laughed and said, “I always want to go to London.”

“Okay,” she said, “I’ve got a bunch of miles. I’ll give you a ticket.”

And so my traveling life began, although surprise gifts weren’t what kept me seeing the world. Becoming self-employed was the key.

I realized early in my business building that I could create a business that paid me to travel. That’s precisely what I did. Unlike corporate travelers, I had total control over where I went and when. As my business grew, it generated plenty of income to include trips far and wide.

In fact, anyone could create special projects to fund their travels. Instead of checking your bank account to see if you have funds to cover that trip to Italy, challenge yourself to create a project that will generate funding in new and different ways.

As popular financial advisor Ramit Sethi suggests, you could begin by selling something on eBay. This serves two main purposes, he says. “To symbolize to yourself that you can sacrifice by selling something, and to symbolize that you can make more money than your standard income. Once you do that, there are many other ways to generate income.”

Late in 2012, my three sister, brother and I decided it was time for a family trip. We decided upon Provence as our destination. We chose Stalking Van Gogh as our theme which made travel planning more focused.

The other project I devised for the trip was to fund it in new ways instead of simply paying for it with the money on hand. I had barely made that decision when my doctor recommended me for a new drug study. After I was accepted, I spent several weeks checking in at the medical center and being monitored. I also earned over a fourth of the trip money.

Although I had done numerous teleclasses over the years, I hadn’t included them in my business for quite some time. I came up with a new series, promoted it and generated another big chunk of the funds.

I did a bit of decluttering and sold some household items that had outworn their usefulness to me, but were welcomed into new homes. I sold a couple of articles to online paying markets.

The closer I got to having the necessary funds, the more eager I became about the trip. Long before our plane took off from Los Angeles, my trip to France was totally funded.

I’ve been slowly building a new fund to support my next adventure.

We all have a choice. We can use lack of money as an excuse or we can see it as a creative challenge. Test it for yourself. You could even start with something small such as a weekend trip that you fund in new ways.

Once you have evidence that such a thing is possible, you’ll be amazed at how often you’ll be crossing the ocean.

Got a current passport?

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