Celebrating Barbara Winter and her joyfully jobless movement

Updated 2024-07-06. Originally published 2013-07-23 on VocationVillage.com

It was a sad day in 2022 when the world lost Barbara Winter. Winter was the author of Making A Living Without A Job, which is a wonderful book that improved the lives of many people. As the book gained popularity, Winter became the de facto leader of a joyfully jobless movement.

Years ago, I attended one of her joyfully jobless weekend events. It was a terrific experience, and here are my favorite seven things I learned:

1. In person, Winter was the same feisty, irreverent, passionate advocate for self-employment as she was in her writing. Her calling in life was to help people leave jobs they hate for self-employment they love, and she spent 20+ years learning to do this effectively.

2. Winter told us that Sophia Loren once said, "I am successful because I was willing to give up being anonymous." This idea really struck me as important because I know how much ambivalence gets kicked up when people put themselves and their work in the world to be open to critique. It is essential to learn to forge ahead despite the fear because, as T. Harv Eker says, you can't go very far when "one foot is on the gas and one foot is on the brake."

3. Many people hate the idea of marketing, but Winter said when you find the right audience for your offer, sales are a natural by-product. If you focus on developing relationships, then there is no need for any obnoxious self-promotion. The goal is to find people who share your values. Winter cited Paul Hawken, the entrepreneur who founded the Smith & Hawken gardening company, who said that gardening is the best training to be an entrepreneur because in both cases, you plant seeds and then nurture them.

4. While credentials might be important for building confidence or networking, many clients or customers do not care at all about credentials. They only care about real world experience and whether you can help them.

5. There has never been a better time to build a business because the demand for products and services is global. Winter told us about Dr. Joyce Brothers deciding that she wanted to teach, but she wanted the world to be her classroom. Since I am already convinced of the advantages of location independence, I love how much this creates infinite possibilities.6. The idea of self-employment frightens many people with salaried jobs, so they give a lot of damaging and negative advice. Winter said to ignore the dream bashers, and learn from people who are happily and successfully self-employed. She quoted Rumi,

When setting out on a journey, do not take advice from someone who has never left home.

6. In the beginning, don't focus so much on "how" you will do things, but on taking action and learning as you go. You cannot possibly know everything in the beginning.

7. Don't struggle alone. In building a business, even introverts benefit from connection. Whether you are brand new to self-employment or you are an experienced solopreneur who wants to meet other joyfully jobless people and learn some new things, find a community of other people building things.


Here is where to buy Barbara Winter’s book, Making a Living Without a Job.

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