How to choose your career: Interview with Barbara Winter
In 2018, I published a book about how to choose your career. In 2024, I moved the content to this site. Below is the interview with Barbara Winter. Ms. Winter passed away in October 2022, but her wisdom lives on.
Why do you think career decision-making is so challenging for so many people?
I blame the Industrial Revolution. Prior to 1900, 9 out of 10 Americans worked for themselves. But you can’t build factories with people who are happy doing their own thing. Everything changed, including education and work.
Seth Godin talks about this, that we are now trained to be efficient in a factory. Having a predictable life became the American dream. But eventually people started asking, “Is this all there is? Is work just to pay the bills?”
I grew up in a small town in southern Minnesota. Most people, by the time they were 21, had made all their major life decisions: where to live, whom to marry, what type of job to have, what church to join, which bowling league to join.
As a child, I knew from a young age that I didn’t want that. I had an extraordinary circumstance in my family: My grandfather was a stern German Lutheran minister who had three sons and six daughters. They were all born before 1920. Astonishingly, he decided that all his daughters should be educated and have careers but not his sons, which was a total role reversal at the time. His sons, one of whom was my father, had very difficult lives and unsatisfying careers. But all my aunts did wonderful, interesting things with their work and their lives. One of them was an army nurse who lived all over the world.
Because I had fabulous role models, I grew up assuming I could have an interesting life, too, and I saw that the work you choose has a great deal to do with how interesting your life ultimately becomes. It was a gradual awareness. It wasn’t quite as simple as saying, “Now that I’ve graduated from school, I am going to have an interesting life.” It took more than a decade for me to start asking questions.
When I see people in my seminars who are in their 40s and 50s, and they are starting to ask questions, I have a great deal of empathy. They tried to do what they were supposed to do in life and they still have nagging questions. Psychologist Abraham Maslow said that if you don’t live up to your potential, you will be miserable for the rest of your days. Many people discover this, one way or another.
In my seminars, I tell people we knew what we wanted to be when we were children and then we got “guidance counseling.” That’s misnamed. It should be named “misguidance counseling.” We get very little encouragement to discover ourselves.
My granddaughter was two when it became obvious she was an artist. Even as a tiny child, she would sit down to draw, and I was astonished at her focus. I decided that, as her grandmother, it was important for me to help protect that and make sure that no one took that away from her. Her mother, my daughter, says to her, “Zoe, you are an artist. Not everyone will understand you and that’s OK.” There are millions of artists who have not had that type of encouragement.
Your “joyfully jobless” approach teaches people how to make a living without a job. Can you tell us more about that?
I first started Making a Living Without a Job seminars in Minneapolis. I started locally before expanding nationally. I was doing a lot of speaking and getting interviewed a lot. People would say, “You’re that woman who talks about not working,” and I would answer, “No, I am the woman who talks about not working for somebody else.”
I was doing a radio interview, and I used the phrase “joyfully jobless,” which is a different thing from being unemployed. Usually, people view joblessness as a bad thing, but I wanted to introduce joy to it.
Many people view work as just a way to make money, but I say, “We get paid in multiple currencies and some of it happens to be money.” There are all sorts of other currencies that I never experienced when I worked for somebody else. For example, seeing the fruits of what you’ve done.
In contrast to the gurus who want to enroll students in coaching programs that go from Silver to Gold to Platinum and want to make people lifetime students, I want something different. From the beginning, I wrote down what I don’t want to do. I don’t want to create dependency relationships.
I see myself as Johnny Appleseed. I plant seeds, but I don’t stay around to see if the tree grows. I just want to get people to the point where I was, asking if there could be more. Then, hopefully, if resistance doesn’t take over, you start exploring and you discover that it is possible, and that there are resources and tools for making it happen.
I use words like “business” and “entrepreneur” because there aren’t better words, but I really mean something different.
You mentioned resources and tools. So many people struggle with the implementation part of what you are describing. Could you please say more about that?
When I started, I read books about business, and it was all so conventional. There was an assumption that you would have financing and employees. That didn’t feel right to me. I wanted something different. I wanted to be independently occupied.
Then I read books about freelance writers, and that appealed to me. That was closer to what I was seeking. My seminars do suggest specific resources. Also, for 25 years I have published a newsletter, Winning Ways, that helps people to identify the best resources.
When I started working at my electric typewriter on my card table in my TV room, I didn’t anticipate what a huge phenomenon the home business movement would become. That wouldn’t have happened to the degree it has happened without the technology to support it. Technology has made it so much easier to work on your own and to connect. I wrote an article several years ago called “Another Barrier Down.” I had an epiphany that we are the first people in the history of the world for whom geography has nothing to do with running a business. That’s powerful! It is so new. Even 20 years ago, if you were going to run a business, you had to physically be able to connect with your customers in some way, unless you were Sears Roebuck. Now you have people like Marianne Cantwell who may be in London or Australia or wherever she happens to land. It is a whole different universe that we are creating.
I know you share some of my beliefs about just how secure a supposedly stable job is. Can you elaborate on what you have learned about the comparative security of salaried jobs vs. self-employment?
If paying your Visa bill is your biggest goal in life, then a salaried job might be the perfect fit for you. But there is so much conflict for people who have been taught since childhood that security lies in “stable” jobs, and yet it isn’t true. In America, we have had a love affair with the giant corporation. People equate “big” with “successful.” People want to hitch themselves to a large corporation and expect to stay for a full ride. But since World War II, this hasn’t been the case. These jobs with big companies are not a lifetime contract. The old paradigm is gone, but people want to bring it back. They want to recapture the lost security, but it hasn’t happened.
My mantra is “Work with the willing.” I don’t evangelize. Until people challenge their assumptions, they can’t be converted. Stepping outside of a routine and predictable life can be terrifying, even though there is a party going on if you just go to the other side of the wall. All you’ve got to do is climb over and you will be welcomed and supported and encouraged. But until people get there on their own, you can’t convince them.
Even when security vanishes right out from under them, people want to believe in the old way. When the recession started and people getting laid off were in a panic, my self-employed friends felt as if they had so many options and could adapt.
However, people who become entrepreneurs can’t bring the employee mindset with them. The same qualities that make you Employee of the Month don’t work for entrepreneurs. I taught a seminar, What Would an Entrepreneur Do? I have a chart with side-by-side comparisons. Employees think about tax refunds; entrepreneurs think about tax deductions. My favorite is this one: Employees commiserate. Entrepreneurs brainstorm. Many entrepreneurs who go back to hang out with friends who are still corporate employees say, “I can’t believe how boring that life is.” It is hard to see when you are in the middle of it. The last thing that fish notice is salt water.
Many people say they couldn’t be self-employed because it sounds scary to them. What are your favorite strategies for dealing with fear?
What is wrong with being scared? It is a normal response. What we call fear (which is a helpful emotion that keeps us out of harm’s way) often isn’t fear ... it is self-doubt. If you get honest, you may see that you aren’t feeling fear, you just aren’t sure you are good enough. You’ve got some work to do, and it is doable work.
I came to self-employment through the back door. I was swept up in the human potential movement, the personal growth and development stuff. At age 30, I discovered marvelous books like Think and Grow Rich—in my heart, I knew it already, but no one had ever said it to me before.
An important part of the entrepreneur’s journey is to develop high self-awareness. Be willing to say, “I’m scared, but so what?” Fear is normal. Acting in the face of fear is an incredibly powerful thing, when we see ourselves being scared but doing something, anyway.
I was attracted to public speaking because it scared me so much. Every time I came through it, I grew a little bit. That was empowering. I did it a tiny bit at a time. I work with fearful people by asking what little steps they could take right now.
People make things too big and that scares the daylights out of them. I do an Establish Yourself as an Expert seminar where I help people who say their goal is to be on Oprah next week. That’s not the way it works. First, you go out and talk to everyone in your community, for free. Be willing to apprentice yourself to your dream. We don’t talk about apprenticeship very much anymore, but we should. It takes a lot of the fear away to be in the learning phase. Pay attention and see what you can learn.
Break big projects into small, manageable steps. I like 90-day timelines. Take inventory at regular milestones, and see what you know now you didn’t use to know, and what you want to know next. Figure out what is working and what isn’t. Review and revise. It is both heady and terrifying.
Some people say they can’t imagine themselves self-employed by explaining, “I just wasn’t raised that way.” My favorite response is, “Would you wear your mother’s clothes?” If not, it means you were willing to change. We’ve lost generations of creativity by not teaching openness to it.
Do you think anyone can be self-employed, or do you think it requires specific characteristics?
I think everyone can, but not everyone will. It requires a willingness to learn and grow. I remember in the Human Potential movement some people would say, “I don’t want to look at myself. I am afraid of what I will find.” But if you don’t encounter your dark side, it takes over.
Your business becomes a reflection of who you are. Years ago, I really loved the book Minding the Store by Stanley Marcus. Books by Paul Hawken also. I wrote about this in my newsletter. Who can be an entrepreneur? Anyone willing — kids, people 50+, people who love people, misanthropes, old grumps. Being an entrepreneur is flexible and adaptable. It is the willingness to step into the role that is key. I love the British word “bespoke.” We get to create a bespoke business that fits us, that is not off the rack.
Look at all the immigrants who come to the United States and they don’t even know the language and they start their own business. What sissies are we that we stand around quivering and talking about risk?
What we call failure is often just running out of patience. Entrepreneurs don’t give up when they fail ... they just try again. Imagine if there was a story about a person, “Once upon a time there was a woman who got an idea and turned it into a wildly successful business the first time she tried.” If that were a movie, you wouldn’t go see it, because it would be so boring! And it is boring to live it, too.
How can people learn the skills of entrepreneurship?
Many people who want to be entrepreneurs are just missing a few tools. If you get those tools, you see how things are possible.
First of all, hang out with a bunch of entrepreneurs. If you have always worked for someone else and you don’t know people who are self-employed, they seem like yeti, like mythical creatures. But they are out there. I wrote an article called Field Guide to Genus Entrepreneurus: Where to Find Them. Entrepreneurs hang out at Starbucks, seminars, adult education classes, Meetup, online. Once you start to look, people will connect you to other people. Until you enter this world, this parallel universe, you won’t realize how vast it is.
The home business revolution has been a quiet one. You can’t drive down the street and know which people have businesses in their homes. You have to seek out people. I’ve seen articles about people and called them up and told them I’d love to meet them, to have coffee.
I tried things that didn’t work for me. I went to the Chamber of Commerce and Small Business Association (SBA) workshops, and those weren’t a fit for me. SCORE stands for Service Corps of Retired Executives, not Service Corps of Retired Entrepreneurs. But I kept looking. I joined Toastmasters, and I found every group has a different personality. I found one that fit. This is all part of wonderful exploration.
Dr. Jess Lair says that every entrepreneur needs four or five people whose faces light up when you enter the room. Those are the people you call on the day you get a new client and the people you call on the day you lose a client. I had a huge disappointment a few years ago that I found out about via email one morning, right before I had to fly to Denver. My friend Karen picked me up at the airport and we went for lunch and I hadn’t yet talked about the disappointment with anyone, but I talked with her. She asked me if I had cried and I said, “Yes.”
She said to me, “You know, Barbara, deep mourning lasts about 48 hours for an entrepreneur.” I realized, “That’s so true!” I move past disappointment so quickly now. Previously in my life, that type of big disappointment would have put me out for a year.
I get upset with the numbers thing: 17,000 connections on Twitter are meaningless if you don’t have that core group of people who are your tiny tribe. Those are the people who make the big difference in our lives.
I have seen people come to my Making a Living Without a Job seminar and a group of people meet on a break and then decide to do a project together. They didn’t know each other two hours earlier. But they put themselves in a place to meet others. There’s a great Stuart Wilde quote: “There’s no use saying you want to be in the movie business and you’re living in Kansas.” The movie business isn’t coming there. Putting yourself in the company of others is so important ... you have to build your circle. At first it can seem daunting, but once you start, it gets easier.
Where do you teach seminars?
In many different cities, most recently Las Vegas, Sedona, Arizona, and the Lake District in the UK. I usually do two-day retreats. Something magical happens when you get people together in a room with people who share your interests and your curiosity. This is something more than what you get when everyone is home alone reading information online. It feels different. There is a very different dynamic that goes on.
What one or two variables have you found to be most predictive of self-employment success?
I know almost immediately who is going to have a robust run and who isn’t. Attitude is a huge factor. The two qualities that are most important are curiosity and a really strong commitment to lifelong learning. Also important are understanding the role of inspiration and the willingness to do the things that inspire you. This is such a personal thing ... we are all inspired by different things.
I’ve lived in Santa Barbara, California, and also Boulder, Colorado. So many people say the beauty of the ocean or the mountains inspires them, and I certainly agreed they were beautiful, but I wasn’t pulled by these places. I joke I must be inspired by concrete because I love cities.
When I wrote my book, my editor asked me to change the section where I admitted I didn’t love Boulder. She said, “Careful, Barbara. We sell a lot of books in Boulder.” But it was such a powerful story to tell readers I had to try something to know how it would feel. People cross things off the list, but they haven’t even tried those things. Then their world gets smaller and smaller and it is very sad.
Years ago, I remember you said that the people who stay in a job just for the health insurance benefits are the people most likely to need to use them. I totally agree that the stress of being in the wrong job can make someone sick, but concern about health insurance is a huge impediment for many who would like to pursue self-employment. What do you currently tell clients about health insurance?
I wrote an article once that I was tempted to name The Last Damn Thing I’m Ever Going to Say About Health Insurance. Most people have never gone shopping for health insurance ... they have just taken what they have been given by employers. I suggest people go shopping and see what they discover.
We have a Neanderthal system in the United States. That’s the bigger problem. The only time I’ve ever been in an ambulance was in the UK. I tripped on a sidewalk and ended up having to go to the hospital. They took care of me, handed me a bottle of aspirin, and wished me well, and I wasn’t even a taxpayer there. That was my glimpse of how other countries do things.
When you are just starting out and you are building up your cash, unless you have a pre-existing condition, get major medical insurance so that if you have a catastrophic crisis, you are covered. Then pay out-of-pocket for visits where you just have a sore throat.
I have a self-employed friend in Minneapolis whose wife was diagnosed with cancer. They had to shop around for health insurance and even in that extreme case, they found a solution that they could handle.
The insurance industry has done a brilliant job of keeping us confused. They make the paperwork complicated and mind-numbing.
In addition to concerns about health insurance, so many people have cash flow issues, so they stay trapped in jobs they hate. Do you have favorite strategies you recommend for clients to bridge financially between their current work circumstances and new and better ones?
I was just ranting about this on Facebook. Most families have not learned to set goals as a team. You need a plan. If you want to earn as much from a business as your job, you have to find out if that is even possible and how to get there.
I met a man who started a voice-over business, and he wanted to take the business full time and earn the same thing he earned at his job that paid him $250,000 per year. I told him he needed to find out if it was even possible to earn $250K as a voice-over artist, because I suspected it might not be.
I teach a class, How to Support Your Wanderlust, because the impulse to travel and the impulse to be self-employed are very similar. Rick Steves has a great manifesto: “Drive that old car another year.”
I ask seminar attendees if they agree with this statement: “Experiences have a higher priority for me than things do.” If your life is about accumulating stuff, then maybe you should stick with your job. This is about way more important stuff than building a pile of crap.
I have a sister who worked for a large publishing company for 25 years. When the company started laying people off, she was working two jobs. They had a sales conference, and they told everyone they had to work harder. I hung up the phone and wondered if there was a management training school for emotional abuse because abusers all seem to know what to say and they sound the same. Domestic abusers and corporate abusers say the same things: “You better stay with me or you won’t have anyone. You’ll end up in the gutter.” This is so very fear-driven. People who have bought into this type of thinking are going to have a very hard time with decreased cash flow.
But there are so many ways to make things happen if you really want them to happen. Read Julia Cameron’s Walking In This World. She says that when you are really focused on something, all sorts of things start happening to support it. Also read Mike Dooley’s Notes From the Universe. He says to pay attention, but most people are oblivious.
I know you are a huge fan of travel and sabbaticals for creative inspiration and renewal. What do you think is especially effective about this for helping people with life decisions?
I have a sister who is an archeologist. We had a meeting in London one time and we had just arrived and she said, “I am thinking of taking a year off and I want you to help me plan it.” We started brainstorming. She lived in Athens, Greece, and she went back home. Within six months, she had grants lined up, she had sublet her apartment, and she had permission from museums in Europe to come do research for them. She seemed so happy, so I asked myself, “Why are academics the only people who get to take sabbaticals?”
Every person I have ever met has said that taking a sabbatical was the best thing they ever did. So I started doing workshops and teleclasses on how to plan a sabbatical. You don’t just say, “Next month I am going on sabbatical.” You say, “I am going on sabbatical next year.” You need time to plan.
Matthew Fox in The Reinvention of Work asked, “What if every 22-year-old went on a spiritual quest for a year after graduation from college?” That would change the world. But we don’t do that ... we shuttle them into corporate jobs.
I’ve been on sabbaticals that were extraordinary experiences and I’m ready to do it again. I’m a big advocate of changing the scenery. Otherwise, it is too easy to fall into an unsatisfying routine.
You have to be intentional about it. I love the idea of entrepreneurial excursions. Something happens to us when we are in a different place. The first time I ever went to Europe, I was in Paris alone on the Metro one night and a couple of drunks came up to me. I said, “Get the hell out of here.” I got on the next train and I realized that if I had been in Minneapolis, I wouldn’t have had the courage to say that. We discover things in a strange place that were dormant at home. It adds to our self.
When I was traveling a lot, I always had a theme. Some examples of themes: “Always taste the crème brûlée.” “See all the Monet paintings.” “Find all the ways to eat chocolate and raspberries together.”
You inspire so many people. Who inspires you?
It inspires me when I see someone doing their work with joy. I have been inspired watching Paul McCartney on stage or a waiter who makes me feel like he has been waiting all day for me to come in.
I saw Pavarotti at a sad concert where he just phoned it in. Then two months later I was back at the same auditorium and I saw McCartney perform and it was like he was singing for the first time. The newspaper said it was like a class reunion with Paul McCartney performing. It was an astonishment. McCartney seemed as if he was having a ball. It was such a contrast, so delightful.
What are the next steps for Barbara Winter’s joyfully jobless journey?
I am doing more retreats to inspire people in beautiful places. I am writing an eBook that has 25 years of compiled tips from my newsletter, Winning Ways. I have a couple of other book ideas. I will continue to be a great grandmother. I will travel more.
I want to live in a world where everyone wakes up excited about how they will spend their day. I want to plant seeds. I want to turn on more lights. I want there to be an epidemic of success.
That sounds great. Thank you, Barbara!
Barbara Winter, we miss you!
Barbara Winter is the author of Making a Living Without a Job.
