Recently, I was browsing in some back issues of Winning Ways newsletter and found myself rereading letters I’d published over the years. I decided to share some of my favorites this month.


I found your book, Making a Living Without a Job, about three years ago. I read it, thought it was inspiring, and put it on my “keep” bookshelf. After a few weeks, I read it again.

Since that time, I have read that darn book at least six times.

When I bought it, I was in a high-pressure, unrewarding job as a foreman for a masonry construction company. Today I am Joyfully Jobless!

I’ve been on my own for almost two years and could not be happier. Not that life is easy: it’s just more rewarding. My relationships with everyone in my life have improved as a result of following my passions.

What do I do? Well, I have several profit centers. I build ponds and waterfalls as one profit center. Another is upgrading concrete patios and garages with coatings. I also trim very tall palm trees. I enjoy climbing way up there!

In addition, I install landscapes, still do masonry projects and sell things on eBay. I am constantly thinking up new ideas to try out.

I could go on and on. You and your book helped me find the courage to step out and change my life—and that of my family too.

Incidentally, I believe in supporting things and people that have a positive impact which is why I decided to send the $36 for the subscription. It’s the least I can do to thank you for what you have done for me.

Sean Williams, Mesa, AZ

In Rosamund Pilcher’s long, luscious novels set in England and Scotland, all sorts of relationships are explored and celebrated. In Coming Home, set against the background of World War II, all of her characters show consistent thoughtfulness.

The smallest favors are greeted with, “Thank you. You are so very kind.”

As I read that, it struck me that adding that bit of applause to a simple “thank you” could start a positive avalanche of kindness.

Unfortunately, kindness nearly met its’ demise when Assertiveness became the buzz word. “Don’t let people take advantage of you. Assert yourself!” we were counseled by the assertiveness brigade.

While I would never advocate being a doormat, I think the concept of assertiveness has been twisted into a dangerous perspective.

Nowhere was that more apparent than one summer when I was returning from a trip to Toronto and had a short layover in Detroit. When I got to the gate for my connecting flight, there was a sign saying the flight had been delayed.

Moments later, the customer service representative announced that it had been canceled.

Immediately, an uproar began. Two biker guys were especially obnoxious, threatening the airline employees and shouting obscenities.

The people at the counter not only had the enormous task of finding new flights for over a hundred passengers, they were also the recipients of endless verbal abuse.

Since I’d recently spent hours in airports due to canceled and delayed flights, I found the news upsetting. I’d been gone for several days and was eager to get home.

When I told the couple waiting in line with me that I thought I was going to cry, the man said, “Oh, please don’t. I can’t handle tears.” We all laughed and began chatting like old buddies.

Another man next to me in the line said, “I’m going to see if they can put me on another airline.” I decided to do the same.

When we finally got to the counter, he and I put down our tickets and the frazzled young customer service woman looked up and said, “Are you together?”

“We’ve been in line so long,” I told her, “that we’ve gotten engaged.” She smiled her first smile of the afternoon before booking me on a flight which departed six hours later than my original one.

By this time, I was resigned to waiting and decided to appoint myself as the social director for all the bumped passengers. I struck up several conversations with strangers and took a 14-year-old girl under my wing.

If I was stranded, there was no point in spending the time being mad and miserable. There seemed to be no shortage of opportunities to cheer people up.

I actually began to enjoy myself.

After the long line of people from my flight had all been rebooked, I walked back to the counter and asked the woman who had helped me forty-five minutes earlier if I could be wait listed for an earlier flight

“I’ll see,” she said as she began typing on her keyboard. “That was Winter, wasn’t it?”

I was astonished. “How can you possibly remember my name?” I asked.“You’ve had so many people in this line.”

She shrugged and said, “I remembered you because you were nice to me.”

At the very same moment, the biker guys were cursing the customer service representative next to her. She probably remembered them, too.

Without realizing it, this woman taught me a lesson I don’t ever want to forget: in dealing with other people, would you rather be remembered for being kind or cruel?

The impression you leave is up to you, of course.

Oh, yes, and she also bumped me up to first class reminding me that kindness is, after all, positively contagious.

Participants had the pleasure of meeting the delightful Marianne Cantwell at the Joyfully Jobless Jamboree in Austin last October. It was the first time I’d met her, too.

According to her Website, Marianne Cantwell is a Free Range Human, and an unconventional career change expert who helps people escape the 9-5 and do what they love (even when they have no idea what that is yet).

I would describe Marianne as one of the most grounded free spirits I’ve ever met. Smart, creative and devoted to helping others escape the cubicle cage, she’s also the only person (besides myself) I’ve heard use the term “bespoke careers.”

Marianne is living her own entrepreneurial dream and she’s eager to share what she’s learned. Do yourself a big favor and spend a few minutes watching this video and getting to know this amazing woman.

Click Here to Learn More

When  speaker Jerry Gilles told his audience of would-be writers that they should buy one hardcover book every week to support the industry they were part of, there was an audible gasp in the room.

What Gilles was suggesting wasn’t radical at all. It is just one way to put into action  the idea to  “Support That Which Supports You.” Successful people do that all the time.

As entrepreneurs, we have numerous opportunities every day to spread the entrepreneurial spirit. Here are a few ways to do just that.

°  Be joyful in the world. Make other people wonder why you’re so happy. As you go about routine errands, think about those you interact with and how they’re part of your success team. The postal clerk, bank teller and print shop are helping you accomplish your goals, after all.  Let them know they’re appreciated.

°  Adopt a protégé. Even if you’ve only been in business a short time, you’ve probably learned more than you realize.  Helping someone who knows less than you do can serve a dual purpose: besides making their journey  smoother, you’ll also see how far you’ve come.

That can be a huge confidence booster. Coach, encourage and support someone who’s just getting started. Ask them to pass it on.

°  Share what you’ve learned. Write a What I Learned From Starting My Own Business article and get  it published in a local business paper or post it on your Web site.

What do you wish you’d done differently? What was the best surprise you got in starting your own business? Pick six or ten key lessons and find a way to share them.

° Talk to the media. Local media is always on the lookout for stories about interesting folks in their midst. Let them know you’re there. Don’t just be a publicity seeker, however. Come up with an angle that’s newsworthy.

Artist Greg Evans had a great piece written  about him in  Colorado Avid Golfer magazine after he sent out a press release titled “From Corporate Life to Creative Life.”

Might your personal story be of interest? Or do you have expert advice to share that could add to your  visibility?

° Do  the opposite. The entrepreneurial path is not about following the crowd. One way to keep your creative muscles tuned up is to find ways to do things differently than everyone else.

Thinking in opposites is an easy starting point for finding a unique way of doing even simple things.

° Be a student of success. Eavesdrop on conversations and you’ll hear how many people are clueless about success factors and the behavior that leads to genuine success.

Teachers like Jim Rohn devoted their lives to studying winners and their findings are documented in books, in seminars and on CDs. Be more than a casual student of what they have to say.

° Conduct regular interviews with entrepreneurs. My niece Gretchen is associate business editor of the Ventura Star. She was telling me that one of the best parts of her job is talking to passionate entrepreneurs. “If they know you’re interested, they love to talk about their business.”

You don’t have to  be a newspaper reporter to take advantage of all this enthusiasm. Seek out entrepreneurs and be genuinely interested in hearing their stories. Easy as that.

° Support small business whenever possible. There are numerous ways to do this beginning with patronizing the entrepreneurs in  your community. You might pay a little more at your local hardware store, but you may also discover you’ll get useful advice along with your purchase.

And don’t overlook opportunities to form alliances and create joint projects with other entrepreneurs. Collaborations can create positive synergy.

° Help a kid. One of the most common regrets I hear from adults is that they weren’t exposed to entrepreneurial thinking earlier. So cheer a young upstart on.

° Connect with your tribe. While some old organizations, such as the Chamber of Commerce, may not be a fit for the new creative entrepreneur, look for places where the joyfully jobless congregate and join them.


Several days ago, I recorded a podcast with One of the questions I was asked was about how we go about finding the essence of our livelihood. Here’s part of what I said:


You know, that was also a huge learning for me: learning the difference between essence and form. Essence really starts by becoming aware of when you feel the most creative and the most powerful and the most inspired, and what are the situations that lead you to feel that way. Finding the essence often is about looking for the intangible quality.


As we identify those kinds of things that really enhance what we’re doing, all of sudden, the possibility starts to explode because it goes way beyond just a single way of making that happen. And we realize, for instance, that the essence of what I love to do is help other people. Or the essence of what I love to do is inspire other people. Or the essence of what I love to do is teach other people. And then we can start asking ourselves the question, “How many different arenas can I create for doing that?”


As if to confirm my thoughts, a mailing arrived today from Rick Steves who is best known as a travel expert. However, I once read that when he’s asked to fill in his occupation his answer always is “teacher.” So here’s a bit of his story:


I’ve always taught what I’ve loved. 


I spent my high school years as a piano teacher. I was well known among parents in my community for taking kids with tear-stained cheeks to my piano bench, starting them out with boogies and pop songs…and eventually getting them turned on to Bach and Beethoven. 


Eventually, I had my own piano studio with a recital hall. In 1980, while I was teaching a piano lesson, a truck dropped off 2,500 copies of my first guidebook — Europe Through the Back Door. During that year’s Christmas recital, parents sat on boxes of travel guidebooks while their kids banged out carols, boogies, and Bach. 


By the following Christmas, I’d let my piano students go. People were still sitting on boxes of books, but now that recital hall was a travel lecture hall filled with eager students preparing for their European adventures. 


From that point on, I would be teaching European culture off the keyboard…to otherwise smart people who assumed Toscanini was a pasta and Botticelli was an intestinal problem. 


For twenty-five years I led our tours while apprenticing hand-picked tour guides. Before long, they would apprentice another “generation.” We carry on that personal-passion-for-teaching tradition to this day.


Do you know the essence of your ideal livelihood? If not, that’s your next assignment. It’s so much easier once you know.

Haven’t I been telling you that self-employment is the best personal growth seminar ever invented? Pamela Rutledge has written a terrific piece that is on the Psychology Today’s Web site called  The Positive Psychology of Entrepreneurship which affirms what I’ve been saying. If you need another reason to be joyfully jobless, see what she has to say. It’s my favorite find of the week.

Siblings Megan and Chris Hurley have a terrific Web site called Finding Benjamin which aims to teach kids about money. They share ideas for business ventures kids can start. And they’re looking for article contributions.

If you’ve been paying any attention, you know that I’m a huge fan of Twitter, which enriches my life every day. Simply don’t understand folks’ reluctance to get into the conversation. However, if at first glance it looks like a high school popularity contest, read this sane article,  The Value of Twitter Followers: Quality Over Quantity which opens with this observation, “Twitter followers have become the status symbol of 2009, but how valuable are they, really? I think we’re placing too much importance on the numbers and paying far too little attention to the actual reasons why followers can be valuable to us.” By all means, take a look at this article and, if you haven’t done so, give Twitter a chance.

I’ve long been fascinated by meaningful coincidences, so I took note when I had not one, but two, requests to do radio interviews arrive within an hour of each other. This was the invitation that came first:

I’m sure you won’t remember me, but my name is Holland Cooke, and I attended your  seminar “Making A Living Without A Job” in Washington DC.

YOU CHANGED MY LIFE…and I’m hoping you’ll let me return the favor.

I’ve been HAPPILY without-a-full-time-employer since January 1, 1995.

Mostly, I’m a media consultant, specializing in talk radio.  And soon, I’ll be moonlighting ON talk radio, when I guest-host the syndicated Jim Bohannon Show on 300+ stations, Monday 7/27 and Tuesday 7/28.  As you may know, Jim took over what-used-to-be The Larry King Show, when Larry moved from radio to TV years ago.

I’m writing to invite you to appear with me.

Back in the 80s, curious-and-entrepreneurial-as-I-was, your book and topic were of REAL interest to me personally.  Now…times-being-what-they-are-economically, I think your message means more than ever, to everybody…and I think it’d be a great hour of radio, outlining some of the principles you told our seminar way-back-when, and fielding listeners’ calls.

The next invitation was from Terri in MN, a woman who had attended a workshop of mine there a couple of years ago. She now has her own radio show. It delights me to get these invites from former students who are giving me a nice opportunity to talk about my favorite subject. 

Summer is the  time of year to catch up on my reading. I have uncovered some real treasures and will be writing about some of them in Winning Ways. One of my new favorites is The Big Leap by Gay Hendricks. It’s not a perfect book (he spends way too much time telling us what he’s going to tell us), but it’s basic concepts are revolutionary.

In many ways this book is a challenge to live our lives from a different state of awareness. The chapter on Time is astonishing, but there’s a line from the book I can’t stop thinking about:

The art of commitment should really be called the art of recommitment. Commitment gets you started and propels you through the early stages of any game, but it’s recommitment that ignites your reserves when you feel like you’re going to give up.

Although trendspotter Faith Popcorn’s best-selling The Popcorn Report came out in 1991 (and is out of print), the ten top trends she alerted us to seem remarkably fresh. Here’s what she told us would move that decade:

Cashing Out: Looking for satisfaction, more of us will opt out of corporate life for a simpler way of living.

Cocooning: In an increasingly unpredictable world, our homes will become important sanctuaries.

Down-Aging: Nostalgic for their childhood, baby boomers make retro pursuits and products popular.

Egonomics: The sterile computer era breeds the desire to make a personal statement.

Fantasy Adventure: Modern age whets our desire for the roads not taken.

99 Lives: Too fast a pace, too little time causes societal schizophrenia.

S.O.S. (Save Our Society): The country rediscovers a social conscience of ethics and compassion.

Small Indulgences: Stressed-out consumers want to indulge in affordable luxuries.

Staying Alive: Awareness that good health extends longevity.

The Vigilante Consumer: The consumer uses protest and politics to keep the marketplace inline.

Popcorn spends a fair amount of the book pointing out the opportunities that come with each of these trends. My favorite exercise in The Popcorn Report is the Universal Screen Test. This is a simple way of taking an idea and holding it up against the major trends. Is the idea of being Joyfully Jobless, for instance, riding the horse in the direction the horse is going? Let’s look.

Cashing Out: Absolutely. The movement away from working for large corporations and doing work that is satisfying is the wave of the future.

Cocooning: Right on-trend again. Creating a homebased business gives us more time in our own cocoons.

Down-Aging: There are many aspect to this trend including a sense of playfulness. Down-agers want a sense of fun about their work and will ignore ideas about retirement age. On trend here, too.

Egonomics: What could be a more personal statement than creating work that’s an extension of who you are? Pass again.

Fantasy Adventure: Our new desire to test the unknown in ways that are safe but exciting makes stepping out on our own a perfect way to live our dreams. On trend.

99 Lives: Regaining control of our time and lives leads us to self-bossing as a partial solution.  We’re going for balance here. Pace will be less frantic. A+ on this one.

S.O.S.: What better way to put your values, passions and social concerns into action? Yes, to this trend.

Small Indulgences: Every successful entrepreneur learns the value of rewarding their progress in small ways. This trend also suggests many product ideas.

Staying Alive: Knowing what we do about job-related, stress-induced illnesses, how could any health conscious person not work for themselves? Major on-trend.

The Vigilante Consumer: Changing the way things are done sometimes involves doing it yourself. Some Vigilantes will discover their most effective weapon is being an honest  businessperson.

According to my calculations, being Joyfully Jobless scores a perfect 10. How do your ideas fit into the trends Popcorn predicted?

$100 Hour: Popcorn also points out that our franchised, repetitive marketplace will spawn a backlash with more folks looking for unique, even custom made products. How might you create one-of-a-kind experiences for your clients?

Explore More: John Woods certainly passes the Universal Screen Test. If you don’t know him, add his Leaving Microsoft to Change the World to your reading list.

The seeds of great discoveries are constantly floating around us, but they only take root in minds well prepared to receive them. ~ Joseph Henry

Everyone going down the road to making a living without a job immediately encounters a sign saying, “Exit Your Comfort Zone Now.” Not surprisingly, many would-be explorers turn around at that point and return to whatever cocoon they have left. Since many people dislike being uncomfortable—even temporarily—they never discover what’s on the other side of their discomfort.

Is it possible to live your dream and stay in your Comfort Zone? It doesn’t appear so. I’ve been unable to find a single instance where that’s been done. Even those who have achieved a large part of their dream are constantly having to stretch a bit farther by checking out the unfamiliar.

Last week, I stumbled upon a public television documentary about Andrea Bocelli.  As you may know, the Italian tenor lost his eyesight at the age of 12, but his willingness to go outside his Comfort Zone remained. The program showed Bocelli in a number of sitiuations that most would consider challenging. Besides a passion for windsurfing and horseback riding, we also saw Bocelli skydive. But his bravado wasn’t confined to physical feats. After becoming an international sensation, he went after his lifelong dream of performing in opera. 

But there’s a larger purpose at work in Bocelli’s life. At the end of the program, he said that his intention is to show people that no matter what horrible or sad things happen in our lives, there are still thousands of reasons to be joyful. 

Stewart Emery once said, “Sometimes making a difference looks like making waves in the complacency of another.” It’s equally true that making a difference in our own lives often involves making waves in the comfort we’ve created for ourselves. 

While life sometimes pushes us into situations that are outside our Comfort Zone, don’t wait for it to happen spontaneously. Every so often, purposely move into unknown territory. If you do, there will be times when you feel like the world’s biggest klutz. Don’t let that stop you. After all, the more frequently you leave your Comfort Zone, the more your horizons will expand. 

Dr. Alan Gregg summed it up in his observation about the rewards of travel. “The main value of travel lies not in where you go, but in leaving where you have been. Go to a new place. Have your former gods challenged. Re-examine your axioms. Find out the evidence for your assumptions, and you will begin to set a true value upon the environment from which you came. I never tire of Sir Oliver Lodge’s way of saying this: ‘The last thing in the world that a deep-sea fish could discover is salt water.'”


Since I am a big fan of Ode magazine and Huffington Post, imagine my delight when Susan Corso, who is a blogger for both, shared my piece on change. You can read it on Susan’s Huff Post blog.