An Interview with Barbara J. Winter

Twenty-Five Years of Entrepreneurial Adventures:
An Interview with Barbara J. Winter

(This interview was originally published at The Dreaming Cafe on April 9, 2009)

I met Barbara Winter for the first time in 1996 when I read her book, “Making a Living Without a Job, revised edition: Winning Ways for Creating Work That You Love”.

Her inspirational book and ideas helped me to start two businesses a few years later.
Safe Schools Safe Kids sold see-thru back packs filled with school supplies and Kids Mail Time was a monthly gift subscription service for children. Neither was very successful from a monetary standpoint, but I had tons of fun and I learned a lot.

Twelve years later I met Barbara in person when attending her Compelling Storytelling Workshop in Las Vegas in July of 2008. Since then she has become a supportive friend and mentor. She is incredibly open and honest. Her enthusiasm for the Joyfully Jobless life is inspiring and contagious.

But, she has no time for whiners and complainers. If you are ready to make the leap to a Joyfully Jobless life she will encourage you, share information, and point you in the right direction. She will not hold your hand, coddle you and do your work for you. If you are to succeed as an entrepreneur you have to know what you want and be willing to do the work yourself.

Barbara’s come a long way since she started. She wasn’t raised in an entrepreneurial household and like most of us she started out her adult life by following society’s rules. She went to college, graduated, found a job teaching high school English, got married and had a baby.

But, when we begin to listen to our inner voices, to that small whisper that calls to us, following society’s rules don’t work anymore.

And, when Barbara listened she embarked on an incredible journey. She is an inspiration to millions, and to me.

The Dreaming Café was born from a seed planted during that Las Vegas workshop. I will be forever grateful for her help and encouragement.

Barbara generously agreed to be The Dreaming Café’s first interview/profile for our Inspiring People to Know section. I hope this interview with her inspires you as much as it did me.

Interview

(TDC – Sandy from The Dreaming Cafe; BW – Barbara Winter)

TDC: When did you realize that the life you were living wasn’t working for you anymore?

BW: I always felt like one of Cinderella’s stepsisters trying to jam my foot into a glass slipper that didn’t fit. But somewhere in the middle of college, I must have made a decision to follow a path that wasn’t really my own. Undoing that decision took a very long time and, I think, was a gradual process. I also realize that when I first learned about goalsetting, the only goals I set were aimed at getting me out of situations I’d gotten myself into.

TDC: What spark led to your decision to work for yourself? Was it a gradual dawning or to you have an epiphany? Was there a pivotal moment or incident?

BW: Even though my thinking was moving in that direction, the big epiphany came from reading SUPERGIRLS: THE AUTOBIOGRAPHY OF AN OUTRAGEOUS BUSINESS by Claudia Jessup and Genie Chipps. It was the first time I realized that a business could be a creative adventure and didn’t have to involve opening a shop. I was hooked. I must have reread the book 4 or 5 times in a row.

Quote from “Making a Living Without a Job, revised edition: Winning Ways for Creating Work That You Love”Pg 12 (original version)
“In my fourth year (teaching) came what I now think of as My Horrible Moment of Truth, when I realized that I could predict with absolute certainty where I was going to be and what I was going to be doing every hour of every day of the year. I was doomed to go through life saying, “If this is March, it must be Macbeth.” It was a terrifying prospect.”

TDC: Who inspired you? How? Who were your mentors?

BW: The above-mentioned authors of SUPERGIRLS, of course. I also realize that I grew up in an unusual family. My grandfather was a strict Lutheran minister who was the father of 3 sons and 6 daughters born in the first 2 decades of the last century. For some reason, all of his daughters were encouraged to have careers so I grew up with this flock of aunts we seemed to have wildly fascinating lives. It was a long time until I realized how powerful their influence was.

Years later, a man named Bob Conklin, a successful entrepreneur in Minneapolis and a personal development junkie, became my first real mentor. I have also a long list of authors I think of as my mentors.

TDC: Are there some you’d like to mention?

BW: Many of my early mentors wrote books which are no longer in print so I usually prefer not to mention them. I was really influenced by EF Schumacher’s SMALL IS BEAUTIFUL. On the personal growth front, a huge influence was Stewart Emery’s ACTUALIZATIONS (also out of print) and the writings of Abraham Maslow, the father of the Human Potential Movement.

TDC: Who were the most influential people in your life when you first started out? Today?

BW: When I first started out, I was doing personal growth seminars for women and there weren’t many female entrepreneurs to use as role models. Mary Kay Ash was one of the few I could study. My first influences were people in the human potential movement, especially a guy named Stewart Emery. Today, I have kind of a changing list of entrepreneurs who fascinate and inspire me. My latest one is Tony Hsieh, the young innovative founder of Zappos.com.

TDC: Can you tell me why Tony Hsieh, of Zappos.com is one of your current favorites?

BW: Because he’s building the most imaginative company where creativity is encouraged and customer service is being elevated to an art form. Tony’s also a lifelong learner himself and a visionary.

TDC: What are some (or one) obstacles that you have faced and overcome?

BW: The biggest personal obstacle (which, of course, interfered with my business life) was coming to terms with alcoholism. When I got sober, I actually began to feel sorry for people who hadn’t had to overcome a huge challenge. The growth from that experience was enormous and continues to inform who I am today. Last September I celebrated 25 years of sobriety and continue to be astonished by my life.

TDC: Wow, I didn’t know. Congratulations. Thank you for sharing something so personal.

BW: I don’t talk about my sobriety much, not because I’m ashamed of what led me there, but because it feels like so long ago and not even my life, if that makes sense.

TDC: What was it like raising a child while also pursuing your own goals?

BW: Sometimes, of course, it was frustrating, but I realized so early on that one of the biggest gifts I could give Jennie was the example of someone who was joyfully jobless. It’s made a lifelong impression on her and when she decided to change course a couple of years ago, I’m pretty sure she knew that I’d be wildly supportive. I assume she’ll pass that along to her children.

TDC: If you were just starting out today, what things would you do differently? The same?

BW: I can’t really answer that question. I’d certainly start small and grow slow again. But today we have such amazing tools that didn’t exist when I was starting out. So it’s really hard to compare.

TDC: What five words would you use to describe yourself?

BW: Curious, funny, complicated, passionate, unfinished

TDC: What has the Joyfully Jobless life provided you that you would not have had or experienced if you had continued teaching or continued to be an employee?

BW: Oh, I could make long lists of answers here. Besides joy and sanity, I would never have amassed over 1,000,000 miles on one airline alone (and probably another 500,000 on other carriers). I wouldn’t have met the diverse and fascinating people I’ve met. I wouldn’t have ever become confident about my own talents nor found a way to share them with the world.

TDC: Do you have a new dream or goal you are pursuing currently?

BW: I always have new projects, but I don’t talk about my goals when I’m in the building stage.

TDC: What motivates you? Keeps you going?

BW: Knowing how many problems there are that need solving in the world and knowing how many people are unaware of their own magnificence.

TDC: What does a sample or typical day in your life look like? Do you have any daily practices or rituals?

BW: I don’t have a typical day, but if I’m writing, that usually happens from about 10-2 PM every day. I am very aware of my own biorhythms and work around them. Love mornings, afternoons not so much, rebound in early evening.

TDC: You have recently revised and updated your book. Any sneak peaks? Any new chapters?

BW: Yes, there is a new chapter inspired by Las Vegas. It’s about putting the odds in your favor. Of course, the new material also includes the Internet (as a tool) and there are new stories from seminar participants who I’ve met since the original book came out. The resource section is also totally new with lots of great book recommendations.

TDC: What is the target publication date for the revised and updated “Making a Living Without a Job, revised edition: Winning Ways for Creating Work That You Love”

BW: August 4, 2010 is the official pub date.

TDC: “Making a Living Without a Job, revised edition: Winning Ways for Creating Work That You Love” is now available!!

TDC: Do you plan on writing a second book? What new products, workshops, etc do you have planned for the future?

BW: I have a couple of things I’m considering turning into e-books. I also am thinking a great deal about expanding my How to Support Your Wanderlust material. That could be because I am currently experiencing a bout of wanderlust myself.

TDC: How is your “current bout of wanderlust” manifesting?

BW: I’ve been a bit of a homebody for the past couple of years, but am not really looking at new travel adventures. My theme for the year is Inspiring People in Beautiful Places and so I’m planning a number of special events. And, of course, my upcoming trip to London is a living example of how I support mm wanderlust.

TDC: Do you plan to retire? What does retirement that mean to you?

BW: Never. That word is not in my vocabulary. One of my first goals was to create a life that was totally integrated and not chopped up into Work, Play, Family, Friends categories. Just me flowing through my life, moving from one interesting project to another. Why would I retire from that?

TDC: Has having grandchildren changed your life? How? What do you most want your grandchildren to know about you, to remember?

BW: I always thought it would be wonderful to be a grandmother, but it’s been even better than that. I remember when Jennie was little and we’d go to a movie or read a book and I’d think how glad I was to have had that experience, which wouldn’t have happened if I didn’t have a child to share it with. I’m kind of back at that place with Zoe right now and loving it. I want her to know that her Grandma Vegas did what she could to make the world safe for her dreams.

TDC: You were able to sum up your Twitter bio in 140 characters or less: “AKA Barbara Winter, passionate about creative self-employment & personal growth”. What advice in 140 characters or less would you give to someone today, regardless of age, gender, economics, or education, to someone desiring to embark on the Joyfully Jobless life, journey, adventure?

BW: (I typed this on Twitter and hit 140 exactly.)

“Nothing is more exciting, adventurous, creative than the Joyfully Jobless Journey. Find a guide and get going. The world needs your gifts.”

TDC: Thank you Barbara for such a wonderfully inspiring and candid interview. It has been a joy to get to know you better!!

You can find out more about Barbara J. Winter at her website: JoyfullyJobless.com and her blog Buon Viaggio. And don’t forget to check out Barbara’s Book List

Barbara also has both a FREE email newsletter, as well as, a print newsletter. Both are unique and full of inspiration and ideas. If you haven’t already, I would suggest you sign up for BOTH right now. You can sign up for her FREE Joyfully Jobless newsletter on her homepage. But, don’t forget your subscription to Winning Ways. It is one of the best investments I’ve ever made!

Read my review of the newly revised “Making a Living Without a Job, revised edition: Winning Ways for Creating Work That You Love” HERE.