There are plenty of Wealth Gurus around insisting that we should all aspire to millionaire status. Maybe that’s your goal. Maybe it’s theirs. What I know for sure is that prosperity consciousness involves getting rid of limiting notions about our own worth and that’s best accomplished incrementally.  Small daily actions add up, after all.


Here’s a Get Rich Slowly exercise that I’ve seen help many people launch and build their enterprises. 


$100 isn’t a huge amount of money—and that’s the point. It’s not so large that it scares us and not so small that it’s insignificant. Approached properly, it can be a useful tool for building abundance.


Here are some suggestions for putting those Ben Franklins (or whatever the equivalent is in your currency) to work.


° Use it as a test for your ideas. One of my favorite $100 ideas comes from Phil Laut in his book Money is My Friend. He suggests that every time you start a new profit center, you make a commitment to stick with it until you’ve earned your first $100 from it. When you reach that milestone, evaluate whether or not you wish to continue. 


Sometimes it takes a big investment of time to generate the first $100, but once there  you can see how to repeat it more rapidly. Other times, you’ll find that you enjoyed earning the money less than you thought you would. 


The brilliance of this idea is that you are making decisions from a wiser position of experience—not frustration or fear.


° Always carry $100 bill in your wallet. It’s a powerful tool for eliminating thoughts of lack and limitation. When you go to spend your last small bill, instead of thinking, “I don’t have any money,” you’ll find yourself thinking, “Oh, I have another $100.” Only spend the bill if you have an emergency or know that you can replace it immediately.


For all its convenience, many of our modern ways of dealing with money involve not actually having much contact with it. Credit cards, online banking and the like make money a distant set of numbers. Cash in our pocket has a different effect on us.


° Be consistent in practicing the $100 Hour. Whether business is booming or slow as a snail, one of the best things you can do on a daily basis is to focus for an hour (if possible) on creating your next $100. Once you’ve mastered consistently creating new sources of cash flow, you’ll probably want to raise the hourly amount. (If you need some idea starters check out the Getting Ideas chapter of Making a Living Without a Job.)


° Spread entrepreneurial spirit $100 at a time. Become a micro-lender at or give the gift of livestock through Heifer International. You might even send an anonymous $100 gift to a friend who’s launching a business. Look for ways to seed worthwhile enterprises and support them.


Want to see $100 Hour idea-generating in action? There’s a terrific example on Barbara Sher’s bulletin board. Thanks, Tituba, for the Twitter alert on this.


Every time my UPS driver delivers another case of Making a Living Without a Job books, I am reminded that this idea almost didn’t happen. In fact, I was downright clueless about how big an idea it was.


Several months after I moved to Minneapolis, I discovered Open U, our local independent adult ed program. I thought this might be a good place to try out some ideas I had for seminars so I sent them a proposal. Making a Living was one of those ideas, but I didn’t think it was the biggest. Although I’d met a number of people in my new hometown who seemed intrigued by my joyfully jobless lifestyle, I suspected it was too radical to be popular. Maybe I’d do a session or two, I thought.


Thousands of seminar participants and tens of thousands of readers later, I am still astonished at how excited I get every time I walk into a meeting room to talk about my favorite subject. Helping others become self-employed has been a continuous source of joy and satisfaction for me.


So here’s a little secret about ideas: we can’t possibly know ahead of time which of our ideas are the real winners. The only way to find out is by putting them out into the world and seeing what happens.


Sometimes ideas arrive too early for the marketplace. Sometimes we discover when we try something out that it’s not as much fun as we thought it would be. Sometimes we don’t get the response we’d wanted, but still love the idea so much that we start looking for better ways of delivering it. It’s all a fascinating experiment.


We can’t know until we get into the game. It’s as simple as that. As Paul Hawken points out, “Owning a business and working for one are as different as chalk and cheese.” Surmising, fretting and musing about being an entrepreneur may be an interesting mental exercise, but it’s only by doing what an entrepreneur does that you can know what it’s really like.


I’m not the first person to discover this, of course. One of my favorite entrepreneurial role models was the late Dame Anita Roddick. Here’s what she had to say about her journey:


There are no rules or formulas for success. You just have to live it and do it. Knowing this gives us enormous freedom to experiment  toward what we want. Believe me, it’s a crazy, complicated journey. It’s trial and error. It’s opportunism. It’s quite literally, “Let’s try  lots of this stuff and see how it works.” 


My thinking was forged in the 1960s and in those days I would rather have slit my wrists than work in a corporation. So we had no organizational chart, no one-year, five-year plan. What we did have was management by our common values.


Entrepreneurs want to create a livelihood from an idea that has obsessed them. Money will grease the wheels, but becoming a millionaire is not the aim of the true entrepreneur. In fact, most entrepreneurs I know don’t give a damn about the accumulation of money. What gets their juices going is seeing how far an idea can go.


And I only know one way for that to happen.



The brilliant Chris Brogan talks about Overnight Success and Excuses. Check it out.


Longevity was the furthest thing from my mind when I started my first business 35 years ago, but when I do an inventory of those years, it’s obvious that creating things with a lengthy life span has been part of the process. Nobody is more surprised than I am that Winning Ways newsletter is in its twenty-third year of publication. Or that Making a Living Without a Job has never gone out of print since 1993. Not all projects have lasted so long, but the things that have are the real core of my business.


Although I’ve been busily promoting and hand-selling for the past twenty years,  there are some other aspects to my entrepreneurial life that are also longevity factors. These are things that I think have made all the difference and kept me moving forward. They’ll help you, too, no matter what the current age of your business.


Passion and Right Livelihood are essential. According to the Buddhists, who coined the lovely term “right livelihood”, there’s a simple test to know if your work qualifies. That test is this: the work becomes more, not less, interesting the longer you do it. Avoiding boredom is only possible if passion is present. Best of all, practicing right livelihood keeps pulling us in the direction of mastery, urging us to learn more, do more, be more.


Understand cycles. Every business in the world, no matter how big or how small, goes through cycles. Down is followed by up—and vice-versa. It takes a year or two of entrepreneurial effort to discover the particular patterns inherent in your business, but once you do, you can work around them. For me that’s meant learning what times of year are most conducive to scheduling seminars and then using the down times from that profit center to work on creating new projects. Cycles also teach us about financial management, if we’re paying attention.


Willingly defer gratification. I have advertising whiz Bernice Fitz-Gibbon to thank for teaching me this one. In her marvelous autobiography, Macy’s, Gimbels and Me, she wrote, “It’s smart to defer gratification. Be willing to take less at first in order to have much, much more later.” I believed her and discovered she was absolutely correct.


Stay focused on the big picture. There’s a temptation to declare failure when a project disappoints or, even, falls flat and fails. However, too many new entrepreneurs confuse a project with a dream. Know the difference.


Evolution is your friend.  Anyone devoted to preserving the status quo shouldn’t embark on the joyfully jobless path. I constantly remind folks that the business you start out with isn’t the business you end up with. If you’re doing it right, you’re growing and changing and your business is a reflection of that. It’s equally important to make wherever you are in the process as exciting a place as possible. Now.


The real key to longevity was expressed perfectly by Paul Harvey whose broadcasting career spanned seven decades. He once said, “I hope someday to have enough of what people call success so that I’ll be asked, ‘What’s your secret?’ to which I’ll reply, ‘I pick myself up again when I fall down.’”




If you want more longevity-enhancing tools, join me for one or more of my upcoming teleclasses. We open on Wednesday, October 14 with The Thrifty Entrepreneur: Doing More While Spending Less. That’s followed by Outsmarting Resistance on the 19th and A Beginner’s Guide to the Seminar Business on the 21st. Can’t attend in person? You can still sign up and receive the audio download for any of the classes.

One of the things Malcolm Gladwell discovered after researching outstanding achievers for his book Outliers is, “What we call talent is really the desire to practice.” He’s not the first person to point that out.

Three years ago, Tiger Woods told the audience of 60 Minutes that he’d been working with a coach to change his game and hadn’t mastered it yet, but said, “I am willing to lose in order to get better.” Then there’s my all-time favorite observation from Mick Jagger who said, “You’ve got to sing everyday so you can build up to being like, you know, absolutely brilliant.”

The willingness to sing every day in order to get better is as important to entrepreneurial success as it is to selling out concerts or winning golf trophies. Yet many adults recoil at the thought of practice, thinking that it leads to boredom. That’s only true if what we’re practicing doesn’t come from our passion.

What may also not be obvious is that we’re all practicing daily and whatever we practice most is what we master. We can excel at stinginess or generosity, originality or mediocrity, boredom or adventure. It’s just a matter of where we’re putting in our time and effort.

I’ve been thinking about the power of repetition since many of the people who ordered copies of the updated

Making a Living Without a Job
had already read the original version. I decided to send an advance reading copy to Sandy Dempsey, who I knew was intimately acquainted with the book, to see what she thought. She sent an e-mail after she’d read about 50 pages raving about the changes. Then she wrote this review in her
Dreaming Cafe mailing.

I’ve had a sneak peak at the newly revised Making a Living Without a Job: Winning Ways for Creating Work That You Love by Barbara Winter and it is going to knock your socks off. I am blown away and even though I have read the original numerous times, the new edition has so many new stories, ideas and resources to inspire, my head is spinning.

I even thought about sending a copy to the President. He could use it as a blueprint to empower and inspire the nation – a nation that was founded on the entrepreneurial spirit.

In reality this book should be mandatory reading in every high school and college and every adult education program This book could change your life!!

Needless to say, Sandy’s review knocked my socks off and I was immensely grateful.

I also realize, of course, that someone who reads this book before they begin their joyfully jobless journey will notice very different things than they would a year or two after opening their business. To paraphrase Clifton Fadiman, “When you reread a book and find more in it it’s not because there’s more in the book. It’s because there’s more in you.”

While we’ve all heard that practice makes perfect, that’s not quite true. Practice makes permanent, but we can only get better if we’re paying attention while we do it. Then we begin to notice where our practice is leading us. We discover only weeks after starting a yoga practice that we can turn our heads farther when backing up the car. Or we find that our fifth media interview is smoother than our first. Sometimes we see that we’re farther along than we thought and sometimes it shows us we need to practice more diligently.

Are you willing?

Making a Living Without a JobOn February 29, 1992, I woke up in my New York hotel room scared to death. I was about to teach Making a Living Without a Job to 125 students at the Learning Annex. Although I’d taught the class dozens of times before and had done so on three previous occasions in NYC, this was different. Two publishers were sending editors to watch me in action. I was auditioning and I was a nervous wreck. Since I hadn’t met either of those editors, I wouldn’t be able to pick them out of the crowd. My trembling self caught a cab and took a deep breath. I reminded myself that all I could do was give it my best shot.

Fortunately, I had help. I am quite certain that the Universe handpicked my audience that day. They were amazing. Not only did everyone listen intently and take copious notes, they asked wonderful questions. I wasn’t the only one to notice that.

At the break, a woman came up and introduced herself, told me she was from one of the publishing houses and said she was loving the class. After she left, another woman introduced herself. Her name was Leslie Meredith and she was the editor from Bantam. The rest of the class is a blur.

To my astonishment, the following Tuesday I received calls and offers from both publishers. I hadn’t considered that I might have to choose and it threw me into a small tizzy. I decided to create a list of questions to ask each editor and see if that made my choice clearer. I called them both on Thursday and as soon as I’d finished, knew that Bantam was the right publisher for me.

Later that day, I called both editors to give them my decision. The losing editor was downright nasty, which took me by surprise, but also reinforced my decision. I called Leslie to tell her that I wanted to work with them and she hollered to a co-worker, “Matthew, we got the Barbara Winter book?”

”The Barbara Winter book?” I thought. I liked the sound of that.

There’s a lot more to this story, of course. There’s the back story about how I spent several years building a base, generating publicity and creating a seminar series that was among the most popular in adult ed programs throughout the country. I did all that before committing to writing a book. I knew that first time authors can have a long wait until publication. My plan–which worked better than I’d expected–was to have a publisher find me, instead of me seeking them.

Then there are all the doors that have opened because of the book. I’ve heard from people all over the world who are enjoying their new lives as inspired, creative entrepreneurs. That’s an incredibly humbling experience for an author.

When I was writing the book, I had a different subtitle that had the word “nineties” in it. Leslie suggested I change that. “This book is going to have a long shelf life,” she predicted. Never in my wildest dreams did I think it would still be in print 16 years later!

This time around, I had a new editor, the delightful Angela Polidoro. Here’s a glimpse of some of the changes you’ll find in the spiffy new edition of
Making a Living Without a Job:

  • How to find opportunity in a chaotic economy
  • Why smart, small, and spunky is the 21st-century business model
  • Using the internet and social networking to open the door to fresh opportunities
  • The best resources to help you create and grow a business that is uniquely your own
  • How to leave “Employee Thinking” behind and build an “Entrepreneur’s Mindset”

As I write in the introduction, “Despite the fact that change is often unsettling, these are exciting times, for those who are paying attention…In an economic climate that teeters on uncertainty, thoughtful people are seeking fresh options—options that honor their creativity, add meaning and purpose to their lives, and allow them to go as far as their imaginations permit.” And as my publicist wrote, “This is the book that can help you get started, and the timing couldn’t be better—so get ready to let your imagination soar.”


If you want to know more about
A Beginner’s Guide to Getting Published
, join me for my upcoming teleclass on Wednesday, August 26. Can’t attend in person? You can still sign up and receive the audio download.

Every Wednesday my suburban newspaper shows up in my mailbox. I always look forward to reading it since the editorial staff seems to think that the most fascinating folks in our community also happen to be joyfully jobless. 

This week there’s a story about a woman who decided to turn her parents’ home into an art and music center, rather than renting or selling the house. There’s another about a man who became an artist at the age of 68. His creations are built out of pieces of wood attached together to tell a story. One is called Out of the Box and represents his lifelong desire to work out of the box as an artist. His works, which sell for $250-$1000, are currently being exhibited at a local gallery.

The front page of the Summerlin View is dominated by a story about Jordan Kelley, 22, and Lawrence Vaughan, 24, who started a free Internet job search Web site called Under the large color photograph of the smiling pair is a story of how they saw a need and set about filling it. But it’s the sidebar quote that got my attention.”We like to innovate and create. We didn’t want to be in a cubicle,” said cofounder Kelley.

In the introduction to Making a Living Without a Job, I said, “I became an entrepreneur because I was curious about what I could become. It was a curiosity not shared by any employer I ever had.” Not surprisingly, I’m also curious about why others have chosen this lifestyle. Here are a few reasons that others have given.

I really love to go places and see new things. Even opening the door to a new hotel room has a feeling of anticipation. I just love it. I could spend my life arriving each evening in a new city. ~ Bill Bryson, travel writer

To me the desire to create and have control over your own life was very much part of the human spirit. What I did not fully realize was that work could open the doors to my heart. ~ Anita Roddick, Body Shop founder

See,my trick in life is to get away from having a job. That’s been my guiding light. ~ Paul McCartney, musician

I get excited about small businesses that are run with passion so that’s what  I recommend in my guidebooks. ~ Rick Steves, travel teacher

I wanted to make my store something a corporate mind would never dream up and that a large company could never sustain. ~ Collette Morgan, Wild Rumpus Books

I became an entrepreneur when I discovered there was not barbed wire surrounding my cubicle! ~ Pat Blocker, Peaceful Paws dog training

But for those who think that an eternal escape from work would be paradise, don’t forget that we all need a playground, and your own company is one of the best playgrounds of all. ~ Derek Sivers, musician and serial entrepreneur

I come from a long line of people who run little businesses to support their art.~ Sophia Coppola, entrepreneur and film director

I became an entrepreneur because I didn’t want to be beige. ~ Maureen Thomson, Memorable Ceremonies

Seems to me that many folks choose the Joyfully Jobless Journey because of a vision of a more congenial life. Along the way, they discover rewards they hadn’t even anticipated. What about you?

This week I’ve been reading the galleys for the new Making a Living Without a Job. I came across this story (which you’ve seen if you’ve read the book) and knew it was worth another look.

When you are willing to invest in yourself and your ideas, you have put your money and time into the one thing that lasts a lifetime and can never be taken from you. Businessman and author Bob Conklin told this story that I’ve never forgotten: “Twenty years ago, my wife and I evaluated all the ways we had spent and invested money. Stocks, cars, insurance, real estate, furniture and all other major investments were scrutinized. Do you know what investment outdistanced the others by an enormous percentage? Ourselves. Any investment in growth or self-improvement had paid incredible returns. Books, courses, seminars, conventions— whatever the learning experience—had always returned far greater rewards than any other investment. The best investment in life is in your own self-development. It will pay off the greatest financial and emotional rewards.”

Echoing that advice is a new study that’s gotten a lot of attention because of the radical discovery that Experiences Make us Happier Than Possessions. Really?

The movers and shakers that I follow on Twitter are frequent participants in seminars and conferences. Chris Brogan has a great article called Build How-to Material to Grow Relationships that was inspired during a conference.

Got wanderlust? So does Gary Arndt and all sorts of other folks featured in Christopher Elliott’s article The Secret to an Endless Vacation

Follow Through Camp is only two weeks away and I am anticipating great things will be happening for the participants. I’ve been seeing so many blog posts and conversations about getting unstuck…and that’s exactly what we’re going to be tackling at Camp. Even though there’s not much time left to make travel plans, we still have room for two more campers. Want to be one?

Finally, I’ve been savoring Twyla Tharp’s The Creative Habit and came across this bit of advice: If it’s true that who you are now and who you will be in five years depend on what books you read and which people you meet, then you need to think more aggressively about those you invite into your creative life…In my career, I’ve collaborated with artists from David Byrne to Milos Forman to Jerome Robbins to Phillip Glass. This didn’t happen by accident. But it made good accidents happen.

It always startled me in the early days of my Making a Living Without a Job seminars when someone would raise an eyebrow and say, “But you don’t actually do this yourself, do you?” Long before I turned my attention to sharing what I’d learned about creative self-employment, I had taken a vow to never teach what I hadn’t learned. Apparently, many folks didn’t think firsthand knowledge was required in order to teach.  In fact, my business plan (if it could be called that) was to be a guinea pig in my own life and pass along what I had discovered.

Teaching what you’ve already learned is on my mind today for a couple of reasons. I am increasingly aware of the growing population of experts, coaches and other authorities who don’t seem to share my commitment to learning first, teaching second. The Internet is full of instant experts, rehashing and repackaging other people’s material. I’ve watched other snake oil salesmen over the years and most of them have a short shelf life so seeing a new batch of them is disheartening. 

Teaching what you’ve already learned is also on my mind because the opportunities to pass along life lessons and skills remains enormous. That’s what sisters Mary Russell Sarao and Barbara Russell Pitts have done to share what they learned as successful inventors.  

Then there’s maverick coach John Williams who is doing some great work in the UK. When his Freestyle Success mailing arrived this week with the following article, I promptly asked his permission to share it with you. He said yes so here it is. 

10 Entrepreneurial Myths

How many of these do you believe?

1. I need a 30 page business plan before I can do anything

2. I’ll need a load of money right from the off

3. I’ll need a team of staff to make it work (slight problem – no money to pay them)

4. I need to know all about finance, management, marketing, sales etc to go into business

5. I’ll need to quit my job (and I don’t have any savings to live off)

6. It’s too risky with the current state of the economy to think about doing something on my own

7. I’ll have to dedicate my life to this one business and never do anything else

8. You’re either born an entrepreneur or you’re not – and I wasn’t

9. If my great idea turns out not to work as a business, I’ll have to stay in the rat race

10. Being an entrepreneur is all about making money at any cost, not about creativity, or doing something worthwhile

None of these are true and yet most of my clients hold at least one of them as a belief when they start working with me.

The truth is all you need to become an entrepreneur is a desire to avoid being stuck in a job and a willingness to learn from other people how to make a business work. You don’t even need your own idea for a business!

If you know you want to start something of your own this year, whether it’s freelancing, consulting, a business online or a just a sideline in your spare time, all you have to do is start. Because if you can start it (without too much risk), and keep an open mind, you’ll learn along the way. And even if your first idea turns out to be a turkey, you’ll find other opportunities start to appear.

I want to encourage more creative people to think entrepreneurially. Because if you can make money out of the stuff you’re most passionate about, imagine how much more of it you can do. And the more you can do it, the more people can benefit from it.

Monday was a National Day of Service and Seth Godin offered 18 creative service ideas that could be a worthwhile way to spend some time whenever you’d like to offer it.

For the past several years, Kiplinger’s magazine has run an annual feature called What $1000 Can Do. Every issue has been filled with ideastarters ranging from be a philanthropist to save energy with a front-loading washer. Although these usually appear in August, you can see previous $1000 roundups online. 

If you’re new to Twitter (or not new, but still perplexed) there’s some terrific info on TwiTip including a helpful piece called 7 Ways to Be Worth Following on Twitter

Everyone who’s been around me knows that I’m a passionate fan of Cirque du Soleil. Besides their breathtaking shows, I’m also a fan of their philosophy of merging business and art. The first Cirque show I ever saw was O and I love it so much that I’ve returned five times. Naturally,  I was excited to hear that Dave Taylor had written about his behind-the-scenes experience (complete with photos) at O.   It’s a rare glimpse into the support system behind the awe.

In case you missed it, take a look at Demi Moore and Ashton Kutcher’s I Pledge video. Then create your own pledge and say it out loud. 

I’ve also been alerting everyone to Rick Steve’s briliant PBS program on Iran. It’s running throughout the country now and into February. If your local station has yet to show it, make a point to see it. It’s a stunner.

When I made my first visit to Austin, TX after my daughter moved there, I wrote about some of the fun and funky businesses there. The new issue of Budget Travel magazine echoes my enthusiasm in their 25 Reasons We Love Austin. 

Stop and Kiss, the fun card game for couples, is offering free love coupons you can download from their Website just in time for Valentine’s Day.

Finally, I know there were more great ideas floating around this week, but I’m on a really tight deadline to finish the updated version of Making a Living Without a Job so that’s currently taking over my life. It’s only temporary, I believe.

It has taken me three decades to unlearn the impulse to be practical.  Just imagine what you might have accomplished if only you’d been encouraged to honor your creative reveries as spiritual gifts. ~ Sarah Ban Breathnach

Buon viaggio….good journey. How nice to have you along.

This blog has been a long time brewing. Hardly a day passes when I don’t come across a fascinating new business idea, inspiring story or useful resource and want to pass it along. Up until now, I haven’t had a vehicle for doing so. That’s where Buon Viaggio comes in.

Here’s what you can expect if you come to visit often. There won’t be much ranting, but there will be lots of raving. I’ve also taken a vow of brevity since I know how distracting and time-consuming it can be to keep up with all that’s happening in Cyberspace. And I promise you that I’ll never blog about what I’m having for lunch.

After all, you’ve got dreams to build and that’s where you should be spending your time and energy.  I’m going to do my best to add momentum to those dreams in many different ways—without taking up a lot of your time. 

So if you need a daily shot of inspiration, this is the place to find it. Benvenuto!

It is when we all play safe that we create a world of utmost insecurity. ~ Dag Hammarskjold