Making a Living Without a Job: Interview with Barbara Winter

Making a living without a job

The Path to Self-Employment

Barbara Winter grew up not knowing exactly what she wanted to do for a living. After college, she worked many different jobs, but never felt she had found her true passion. Eventually, Baraba became interested in personal growth, and she found more confidence in herself and her ideas. She decided she would start her own business, The Successful Woman, which was focused on personal growth for women. She began hosting a class called “Making a Living Without a Job.”

Here are a few key takeaways from her interview:

  • A good starting point is to try out numerous different ideas you have – we often don’t know which idea of ours is the best at first

  • To get started, one of the most important things is connecting with others who are self-employed, and take note of their processes and ask questions!

  • One sign of working with passion is that the longer you do something, the more interested you become

  • The business you start out with isn’t the business you’ll end with. Self-employment helps us learn our own strengths and talents -- it’s an ongoing learning experience 

  • It’s important to know what times of day are the best time to focus on different things - maybe in the mornings you’re more productive with writing, and in the evenings you have more energy to working on other tasks

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Barbara J Winter is a pioneering self-employment advocate, writer and teacher who has spent the last thirty 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 Winning Ways newsletter, the longest-running self-employment publication of its kind, she is editor/publisher. Readers of Making a Living Without a Job, a book that’s been in print since 1993, know her as the author. Participants in Barbara’s seminar of the same name, along with others including Establish Yourself as an Expert and How to Support Your Wanderlust, know her as a passionate teacher.

She also leads retreats to help small business owners bring creative thinking and fresh ideas into their work. She is convinced that small is still beautiful and loves working with one-person enterprises. Barbara is also an intrepid world traveler and curious lifelong learner. When she isn’t out exploring the world, she can be found blogging at JoyfullyJobless.com, connecting with other entrepreneurs on Facebook or reading a really good book.