Adventure Calling? Or Same Old, Same Old?

It’s foolish to spend your life not becoming an expert at your passions.

~ Richard Branson

Postcard from Barbara

Reminder From a Handyman

Countdown to Launch

Coming Joyfully Jobless Weekends

Postcard from Barbara

When Nick Williams and I were first getting to know each other, I asked him, “So are you a writer who speaks or a speaker who writes?” He smiled, shook his head and admitted he wasn’t sure of the answer. 

I knew my answer, however, since I’d been pondering it for a very long time. When I began my first business, The Successful Woman, my vision was to create personal growth seminars for women. It was a radical notion at the time when all such material was written by men, for men.

It wasn’t long after I launched that I realized participants could benefit by having on-going support once the seminar was over. And so The Successful Woman newsletter was born. I knew nothing about creating such a publication, but found a helpful print shop owner who explained the mechanics. 

The bigger challenge, of course, was that I had never considered being a writer. I jumped in reminding myself that I could only learn by doing. Before long, I had a substantial list of subscribers (who kept me going) and some surprising national publicity that brought more opportunities. 

As you may have noticed, we live in a world that seems to run on routine. Most of us grew up with a Life Planning Program that went like this: 1) get an education, 2) get a job, 3) stay put, 4) live predictably ever after.

Happily, more and more of us are exchanging that Routine Life Plan for something more exciting and satisfying. That something more frequently involves trading predictability for discovery.

Running an evolving business gives repeated nudges for not staying put. You quickly learn, if you’re paying attention, that new skills and perceptions lead to new invitations to explore and learn.    

Best of all, you learn that who you are today is not who you have to be tomorrow. 

Reminder From a Handyman

Although I’ve told this story before, I still think about it often since it’s a great reminder that some of the best rewards of self-employment go beyond earning income. Here’s what happened.

The dishwasher in my apartment in Minnesota wasn’t working properly so I reported it to the manager. A couple of hours later, a cheerful handyman showed up. I led him to the kitchen and as he began looking for the problem, we started chatting. 

He told me that his wife had died in a drowning accident and he had spent years as a single parent. In order to be available to his kids, he quit his job and began buying up houses and renovating them. He and his family would live in the houses while the work was being completed. Once a house was sold, they’d move on to the next one.

Eventually, he began investing some of his profits in stocks which also did well. Meanwhile, his kids grew up and it was time for his next chapter. 

“So do you work for the property management company?” I naively asked. He looked insulted.

“Noooooo,” he said, “I have my own business. I get to drive around in a truck with my name on the side. I get to fix new problems all the time.” Then he laughed and said, “You know that thing I just did to your dishwasher? I’ve never done that before.”

Can you imagine a life filled with days doing things you’ve never done before? That hardly leaves any time for boredom.

Countdown to Launch

As the time draws nearer, my excitement grows stronger. My wonderful Collaborators and I have been working for the past several months to launch our upcoming Joyfully Jobless Weekends. 

Whether you’re contemplating starting something of your own or already building your own version of a small business, you won’t get very far without ideas and information and inspiration. 

That’s where the Joyfully Jobless Weekend comes in. The Weekend begins on Friday evening with Becoming a Great Idea Detective. The exploration resumes on Saturday with Making a Living Without a Job and I Hate Marketing. You can find more details about each of these programs at

However, there’s a bigger reward with attending that goes beyond the information. As Seth Godin points out, “I  believe that it’s our urgent obligation (and precious opportunity) to learn more and make things better for those around us. What we’ve found, though, is that it’s the lifelong journey of connection that powers that learning. That surrounding ourselves with others on the same path is at least as useful as learning something new."

So if you’re ready to add some adventure and exploration to your own portfolio, while surrounding yourself with others on the same path, claim your spot now. This is a small group event so seats are limited. 

You can register for just one or join us for all three and give yourself a nice discount. That’s not just the best deal, it’s also a great investment.

Coming Joyfully Jobless Weekends

Although more locations are under consideration for later in the year, here are the ones currently scheduled. 

Seattle, WA
March 27 & 28

Bucks County, PA
April 24 & 25

Niwot, CO
May 29 & 30

Houston, TX
June 12 & 13

Minneapolis, MN
September 11 & 12

Note: Don’t see one close to you? If you’re self-employed, your travel expenses plus the enrollment for the event are a tax deductible business expense. 

Buon Viaggio,  

Barbara Winter

On occasion, I may receive a commission or compensation when you participate or purchase a product or service I recommend. That being said, I strive to always offer useful content and resources in each issue of Joyfully Jobless News. 

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Copyright 2019. All rights reserved.

Joyfully Jobless

PO Box 800971
Valencia, CA 91380