A Talk with Barbara Winter

Author of MAKING A LIVING WITHOUT A JOB

MAKING A LIVING WITHOUT A JOB has never been out of print since you first published it in 1993 and is now more salient than ever.  Why do you think your message resonates with so many people? 

There are so many diverse reasons, I think.  When we go through a time like we’re in right now, there’s the obvious explanation: more people are finding themselves unemployed.  Some of those folks have been contemplating self-employment for a while, may have an idea they’ve been considering and see their job loss as an opportunity to try something new.  Even when they don’t have an idea, they might be so frustrated in their new job search that they start considering new options.

However, there’s another phenomenon, less visible perhaps, that I think has fed this new interest in self-employment.  I first noticed it during the seventies when the Human Potential Movement was raging.  Over and over again, I’d be at personal growth seminars and hear people talking about their dream of starting their own business.  I realized that there’s a connection between self-esteem and self-employment.  People who have gone on a spiritual or personal growth quest reach the point in their studies when they need to have a laboratory to try out new ideas.  As it happens, making a living without a job is the best personal growth seminar ever invented.  It challenges us every day to be more and do more, to discover capabilities we didn’t know we had.  That’s both terrifying and exhilarating.

How has the entrepreneurial landscape shifted since you first emerged onto the scene? 

Nobody needs to remind us that we’re living in a time of enormous change, but when I think back on what was happening when I first wrote the book in 1992 and what’s happened since, it takes my breath away.  Technology has opened so many new doors to self-employment that it’s quite dazzling.  At the same time, folks who aren’t particularly passionate about running an online business need to know that there are unlimited opportunities to make a living without a job in other ways.  So in the updated version, I aimed to give an overview of all kinds of businesses.

One of the biggest changes has come about simply because more and more people have decided to explore the world of self-employment.  A few years ago, I spent six weeks as a Junior Achievement volunteer teaching fourth graders about free enterprise.  On the first day, I asked the kids how many of them knew someone with a home based business and almost two-thirds of them raised their hands.  That wouldn’t have happened twenty years ago.  As more and more of us work this way and share what we’ve learned, the easier it gets for everyone.

Millions of Americans are out of work, and millions more are worried about losing their jobs.  Many of us may have to learn how to make a living without a job, whether we want to or not.  In today’s economy, what reasons are there for voluntarily going jobless?

The potential rewards can be huge—and not just financially.  Spending our days doing what we do best and sharing it with others is heady stuff.  I have a good friend who recently started her first business after years of toiling in a less-than-satisfying job and she’s still wondering if it’s okay to get paid to have as much fun as she now enjoys.  For the first time in her life, she is being creative and loving this business she’s designed for herself.

Sometimes it seems to me that the rewards of self-employment are the best kept secret in the country.  While most folks immediately mention “freedom” as their greatest reward, there are others that are personal to each of us.  For instance, I spent the first part of my life living in a small town that I found stifling.  One of my incentives for being successfully self-employed was so I could live in different places.  Thanks to having my own portable business, I’ve lived in very different, but wonderful, parts of the country.

People with young families often cite having more time with their kids as a benefit.  Another reward that was a surprise to me is the ability to work odd hours.  I’m not nocturnal, but I know a number of entrepreneurs who happily work late into the night.

And, of course, creating the perfect business might also be about the things you can eliminate—like traffic-clogged commutes, unpleasant co-workers, uninspired activity.

We often forget that the free enterprise system is accessible to anyone willing to use it.  Over and over again, people who are joyfully jobless say that their only regret is that they didn’t start sooner.

Striking out on our own must require some start-up money or assets, or at the very least a little bit of risk.  How did you get started, and how do you advise others to do so?  Why do you say that having too much money can be an obstacle to being “joyfully jobless”?

While risk is a relative concept, new entrepreneurs need to understand that launching a business may require some trade-offs.  One of my favorite stories came from a student who had left her job to pursue her passion as an artist.  She called me one day and said the biggest surprise for her was how much less money she needed when she was doing the work that she loved.  She went on to say that when she had a job she loathed she’d spend every weekend shopping, hoping to buy something that made her feel good enough to go back to work on Monday.  I think there’s a huge connection between over consumption and unsatisfying work.

I know so many people, myself included, who started on a shoestring—and a very thin one at that.  One of my favorite entrepreneurs is Robert Stephens, the founder of The Geek Squad, who started his little computer service business with an investment of $200.  He says (and I completely agree), “In the absence of capital creativity flourishes.”

Paul Hawken, another favorite entrepreneurial hero, points out that when people start a business that’s highly capitalized, every time they have a problem they tend to throw money at it.  Eventually, they still have all their problems but their capital is exhausted.  So one of the great lessons of building from the ground up is learning to be a creative problem-solver.  That also can be enormous fun, by the way.

What are the advantages to working with a smaller business than a big-name corporation?

Many people have learned, from their bad consumer experiences, that dealing with big corporations can be an exercise in frustration.  While there are companies like Zappos that are making customer service an art form, if you look at their methods you see that they operate more like a tiny business than a big one.  They’ve thrown away the conventional model and given their employees autonomy.

If you are the business, your investment in doing a good job is high.  In my marketing seminars, I urge students to make smallness their biggest asset.  And everyone seems to get what I’m talking about when I suggest that.

What the most common obstacles people face while trying to pursue their passions?

For starters, many people claim not to know what their passion is.  Sometimes they really don’t know, but very often their true passion is hiding in plain sight.  Often it’s something that comes so naturally and easily to them that they don’t realize it is valuable to others.  I’m thinking of a woman I know who is a natural organizer, but didn’t see that she had the makings of a great business because she was convinced everyone could do what she does.

Once people have some idea about the kind of activity they’d like to build a business around, the next hurdle is often in the form of erroneous advice from people whom I call "uninformed sources.”  The Persian poet Rumi said, “When setting out on a journey, do not seek advice from someone who has never left home.”  Same thing is true about self-employment.  If you listen to Uncle Joe has worked at the same job for 30 years and whose only goal is to retire, you may get advice that reflects his fears and has nothing to do with your actual potential success.

So connecting with other joyfully jobless people right from the start can accelerate progress dramatically.   I also tell my students that they need to focus on what they want to accomplish and be flexible about how to get there.   Our business tends to open up paths that we couldn't foresee until we got going.

What are Multiple Profit Centers?

When you work for a salary, you have a single income source.  As an entrepreneur you can create several or many income sources.  Every time you add a product or service to what you’re doing, you create a new profit center.  Most businesses, big and small, have different income sources. Some are the main cash flow generators, while others may be occasional or smaller.

How has the internet revolutionized self-employment?

In every possible way.  Not only has the Internet become a global marketplace, but it’s also a primary source of information for most of us.  Personally, I love the ability it gives me to connect with other self-bossers from around the world.  That’s been happening for quite some time, but these days I’m wildly enthusiastic about the folks I’m meeting thanks to Twitter.

In MAKING A LIVING WITHOUT A JOB, you talk about the $100 hour.  What is it, and have you actually successfully employed the $100 hour?

The $100 Hour is an exercise I first created for myself when I was revamping my business.  I had a large project that was taking up much of my time, but I wanted to keep generating ideas so I’d have other things in place when the project ended.  Later, when I began teaching my Making a Living Without a Job seminars, I realized that this was a valuable tool to get people started coming up with ideas on a daily basis.

It’s simple really.  You set aside regular time every day and challenge yourself to think of a way to generate $100.  Then you start setting your idea in motion.  That might mean writing a quick e-mail or making a phone call or putting an ad on Craigslist.

This is also the way to prevent huge cash flow ups and downs when you’ve got things launched.  I still do this exercise, although I’ve raised the hourly amount.

What’s next for Barbara J. Winter? 

One of my greatest passions is to spend time with creative entrepreneurs in beautiful places.  I started doing a 3-day event last year called Compelling Storytelling, which came out of my desire to help entrepreneurs discover and tell their own stories in the most fascinating possible way.  This year, I launched another retreat program called Follow Through Camp to help people get their ideas moving ahead.  But the form doesn’t matter so much to me.  I just get up every morning and ask myself, “How can I spread some entrepreneurial spirit today?” and then I follow my hunches.