There are numerous ways to become an entrepreneur. If you’re Italian, you might be born to it. Just as homes stay in the same family for generations, Italian businessowners commonly pass their enterprises down to their children.

If your family made wine, there’s a good chance that you’ll make wine. Even some Venetian gondoliers are following the career path of their fathers and grandfathers.

As much as I love the Italians, I’m grateful that finding a career by inheritance isn’t such a common practice here. If it were, I’d be an electrician.

Paradoxically, there’s a Tuscan proverb that says, “Whoever does another’s trade makes soup in a basket.” Perhaps that doesn’t apply to family endeavors.

Although there are people who happily take over the family business, having one foisted upon you can be a disaster.

I met a man in one of my seminars who told us he’d spent his life grudgingly running a family business that he loathed. His sadness was visible, but even though he was no longer young, he was working diligently to make a new start and bring to life an idea of his own.

Even though families may not hand down a business, family pressure still plays a huge (and often unsavory) role in career choice. I frequently have people tell me, “My parents always told me I should work for someone else because it’s more secure.”

I want to counter with, “Would you wear your parents’ clothes?” Their thinking may not fit you either.

Every day I encounter people who are making soup in a basket, who are bored, inept or downright hostile because they are doing work that comes from a place other than their heart and soul.

Finding our personal right livelihood is too important to our well-being to overlook. We may choose to follow in our family’s tradition but only if we’ve come to know ourselves well enough to know that this is a perfect fit.

Clothiers talk about bespoke garments, meaning made-to-order clothes that are fitted to the wearer. I think it’s time to talk about bespoke businesses, one of a kind undertakings that are perfectly suited to the owner’s values, talents and dreams.

It takes a lot more time and energy to create such a business, of course, than to just pull one off the rack. Like a master tailor, we can only produce a bespoke business by knowing our personal measurements, making numerous adjustments, and investing pride in our work.

In a world that often seemed determined to do everything fast, creating a bespoke business requires a willingness and discipline to slow down, take things a step at a time, and pay loving attention to details.

The rewards for such willingness are huge, although they may not be quick.



When a man in one of my How to Support Your Wanderlust classes told us that he was interested in writing travel essays, I asked him what it took to be a successful writer of travel exposition.

Without hesitation he said, “You can’t be a good writer without being a good reader.” I’ve heard many other successful writers say the same thing.

On a road trip, I happened to hear John Tesh’s radio program. He had e-mail from a 15-year-old boy asking how to make it in the music business. Surprisingly, Tesh didn’t suggest more practice.

He said his best advice was to listen to great music everyday and study what other musicians do.

In a fascinating appearance on the OWN’s Master Class, Simon Cowell talked about his early days working in the music business. Cowell said he was a sponge soaking up the advice of those around him who were more experienced.

This advice seems so obvious to me that I’m always surprised to discover that everyone isn’t an enthusiastic student of success. When I ask participants in my Establish Yourself as an Expert seminars to name a favorite expert, I am often greeted by silence.

When I edit manuscripts, it is often apparent that the would-be writer is not an active reader.

Would-be entrepreneurs have never had a conversation with someone who is successfully self-employed about how they got started.

Years ago, Timothy Galway wrote The Inner Game of Tennis and cited studies that showed that players could noticeably improve their game by watching great players in action.

Galway suggested that our subconscious minds absorb useful information and details without our even being aware of it.

So where do you want to succeed? Study those who have done what you want to do.

Absorb the lessons of success, not failure.

Be a keen observer. Identify with excellence at every turn. It will make a huge difference in your ultimate results.

The amusing Quentin Crisp once noted that it’s no good complaining that you really wanted to be a ballet dancer if you continued to spend your life as a pig farmer.

C.S. Lewis said it a bit more elegantly: “Good things as well as bad are caught by a kind of infection. If you want to get warm you must stand near the fire; if you want to get wet you must get into the water.

“If you want joy, peace, eternal life, you must get close to, or even into, the thing that has them.

“They are a great fountain of energy and beauty spurting up at the very cente rof reality. If you are close to it, the spray will wet you ; if you are not, you will remain dry.”


“Too much money, not too little, is a bigger problem for most small businesses,” says Paul Hawken. “In a business, money does not create anything at all, much less ideas and initiative. Money goes where those qualities already are. Money follows, it does not lead.”

Here are a few ways to pump up the initiative.

° Create attention-getting devices. Your business name, tagline, or vehicle call all get you noticed for the right reasons. If you need inspiration, study how the Geek Squad did it.

° Adopt a protégé. Since we learn best by teaching, what better way to sharpen your skills than by helping someone else? The satisfaction of encouraging and supporting someone else’s success is immeasurable. Ask any teacher who’s had a student go on to do great things.

° Become a media darling. Radio, tv and Internet programs are always on the hunt for interesting people to interview. So are local newspapers. Be one. Don’t just think of this as a way to promote yourself, however. Offer useful information to the audience. You never know who’s listening.

° Join forces with a bookstore. A friend and I once spent an evening at a local bookstore listening to two women who were feng shui consultants. Although they were not authors themselves, the store had publicized their talk. A nearby table display was piled with the store’s inventory of books on the subject.

Another variation of this came from a career coach who did a reading list of books for career changes printed on her letterhead. The list was placed on a display table at the bookstore along with the recommended titles.

° Add a personal touch. In this noisy, often indifferent world, looking for memorable ways to distinguish yourself can make a huge difference. Use your photo on brochures and your Website, have a trademark color, do something that nobody else is doing…like sending handwritten thank you notes.

° Show up on stage. Give talks to local groups, volunteer to be part of a panel discussion at a conference. You may not get paid for these gigs, but you’ll be creating connections.

° Participate in community events. A dogsitting business expanded their visibility and customer base by marching in a local parade wearing t-shirts emblazoned with their business name.

You might donate a prize to a local fundraiser, volunteer for a community project, talk to a local high school on career day. Opportunities exist whether you live in a small town or large urban area. Look for them.


The other day someone posted a link to this blog post by Jon Morrow. Since I’ve been following Jon on Twitter for quite a while, I decided to see what he had to say. I couldn’t have been more surprised to learn his story.

I quickly posted it on my Facebook page and the people who took time to read it left comments that pretty much sounded like one big AMAZING.

This one’s going in my permanent files. You might feel the same way about it after you take a look. Incidentally, it’s been retweeted almost 2000 times as of this writing.

How to Quit Your Job, Move to Paradise, and Get Paid to Change the World by Jon Morrow.


In her autobiography, actress Joan Collins revealed that she ended her affair with Warren Beatty because of his annoying habit of accepting business calls in the midst of their lovemaking.

While you may not share Collins’ problem, interruptions can plague anyone who is trying to accomplish a dream. This seems to be especially true for those who are running a business from home.

Years ago, my mother called to ask me to run an errand for her and prefaced her request by saying, “Since you don’t work, dear….”

Your family and friends may think the same of you if you’re running a business from home. Such disruptions can not only impede progress, they can cause you to lose sight of your most important goals.

An interruption occurs when a lower priority intrudes on a higher one. We usually think of interruptions as being caused by another person who distracts us from what we are doing, but  we can also interrupt ourselves by letting petty things take up our time and attention.

Consider this confession from author Jessamyn West: “Whenever I’m writing a book I never get out of bed, because if I do get out of bed I always see something that needs dusting.”

The best way to handle interruptions is to prevent them before they happen and that requires taking a proactive stance. If you sense that distractions are sabotaging your efforts, keep track for a day or two of every interruption you encounter.

Is there a pattern? Are there people who keep showing up? What causes you to be distracted?

If people are causing the interruption, your first line of defense is to establish boundaries with those people who may have gotten used to your availability.

“No, I can’t run over and help you turn your mattress right now, but I will be glad to help you this evening,” is one way to handle requests that interfere with the project you need to complete.

The people who live under your roof also need to understand your need for uninterrupted time. One woman with teenaged children took to wearing a hat  when she was working to signal her family that she was to be left alone. Another gave her children permission to interrupt her only if someone was bleeding.

Don’t assume that other people will know that you don’t want interruptions. Tell them when it is and isn’t appropriate to contact you.

Whether it’s your family or friends, you’ll lower your frustration level considerably by explaining in advance that you are serious about your business and will be unavailable at certain times.

Preventing unnecessary interruptions falls under the general heading of Good Time Management. “Without the management of time,” said William Reiff, “you will soon have nothing left to manage.”

People who are highly productive tend to guard their time carefully. Your work matters, too, and deserves your full attention when you’re creating, inventing or planning.

Yet many people seem oblivious to the importance of limited accessibility and the mobile phone has made it possible to reach them anytime, anywhere.  Unless you deliver babies or repair computers, there’s probably no reason to be on call twenty-four hours a day.

Since the telephone is most frequently the instrument of interruption, it makes sense to be its master. Some people find it easiest to have a regular time to receive and return calls. Your answering message could even explain to callers that you will get back to them between 2 and 4 , or whatever fits your schedule.

Keep looking for creative ways to limit interruptions. Consider a quiet location other than your office for doing some of your work, for instance.

“Things that matter most,” said Goethe, “must never be at the mercy of things that matter least.”

Start every day with a brief review of what you want to accomplish and determine what has the highest priority.

Knowing what matters most is what makes it possible to finish that novel while the dust piles up—or to give your partner your undivided attention because you’ve finished your work for the day.


Ever since I read Paul Hawken’s marvelous Growing a Business, I have looked for metaphors in the plant world to help me solve problems and find better ways of growing my business.

Even though I never lived on a farm, I grew up surrounded by small family farms and went to school with kids who lived on those farms. I didn’t realize they were teaching me many things that would serve me well as a non-farming entrepreneur.

I noticed that even though side-by-side farms endured the same weather conditions and shared the same soil, they didn’t necessarily produce the same results. The human factor had a great deal to do with a farm’s success or failure.

In most places in the Midwest, spring is for planting, summer is for growing and autumn is for harvesting.

So what does a farmer do when the crops are in the ground, but not ready to come out?

A smart farmer works on growing the business.

Your business may resemble a garden more than a farm, but here are some lessons gleaned from good farmers that will also work in a small garden.

Make business a daily practice. Eastern disciplines such as yoga and meditation talk about the power of daily practice.

Paul Hawken says, “Business is no different from learning to play the piano or to ride a surfboard. With most activities there is no presumption of excellence in the beginning, but many newcomers suppose that they should sit down at the desk on the first day and become Superbusinessperson, in full command of the situation.”

Even if you have not made the transition from employee to entrepreneur, having a regular time every day to move closer will bring big results over time. For instance, if social media is part of your activity, spend a few minutes every day rather than a big chunk of time posting once a week.

And if you are years into running a business, be diligent about cultivating new ideas. Complacency is the beginning of the end of even the best business ideas.

Get rid of the weeds. After a seminar I taught on thinking like an entrepreneur, I received an e-mail from one of the participants telling me that her first project after the seminar was to get her home office in order. That involved removing nine large bags of trash.

Even if the clutter’s gone, spend time every day pulling weed or two. Get rid of a self-limiting thought. Cancel a project that no longer excites you. Eliminate what you don’t want to make room for the things that matter.

You get the idea.

Build a Seed Bank. Like a regular bank, a Seed Bank is a physical place where you store ideas.

The best way I know to build such a collection is to constantly be on the lookout for ideas and write them down when they come. Cocktail napkins should only be temporary; your Seed Bank deserves its own special place.

Challenge yourself to see possibilities. If you faithfully did this for the next 90 days, you’d have more ideas than you could use in a year.

Don’t be afraid to get dirty. The Joyfully Jobless life is participatory, not a spectator sport. Try things. Be willing to do things badly. Reconfigure. Learn to find creative solutions.

Keep watering and nurturing. Staying inspired and creating an excellent business requires on-going attention. Know what inspires you and refresh yourself often.

Connect often with people who fan your own creative spirit. Once you’ve spent time with a group of creative thinkers, it’s a pleasure you’ll want to repeat. Accept invitations—and issue them, too.

As Goethe said, “To know someone, here or there, with whom you can feel there is understanding in spite of distances or thoughts unexpressed–that can make this earth a garden.”


It’s no surprise to me that so many people who embark on the Joyfully Jobless Journey are also travel enthusiasts.

Since I’ve been seriously nesting for the past five months, my wanderlust is feeling a bit neglected. I’ve hardly set foot on an airplane during this time, for goodness sake.

So when I was moving some things in my office this morning, I noticed a traveler’s journal someone had given me and decided to take a quick look. Every page has a travel quote on it and I couldn’t bear to keep them to myself.

Here’s a short sampler of some of my favorites. It’s easy to see how they can also be a metaphor for self-employment.

I hate a room without an open suitcase in it…it seems so permanent. ~ Zelda Fitzgerald

Traveling, especially traveling light, teaches you the difference between what is important in life and what may be an onerous burden. ~ Rick Berg

The man who goes ahead stumbles, so that the man who follows may have his wits about him. ~ Kenyan saying (This is also true for other pioneers.)

The traveler was active: he went strenuously in search of people, of adventure, of experience. The tourist is passive: he expects interesting things to happen to him. He goes “sight-seeing.” ~ Daniel Boorstin

I was once asked if I’d like to meet the president of a certain country. I said, “No, but I’d love to meet some sheepherders.” The sheepherders, farmers and taxi drivers are often the most fascinating people. ~ James Michener

Someone said to Socrates that a certain man had grown no better by his travels. “I should think not,” he said, “he took himself along.”

Travel is transformational, the thing that keeps our world vibrant and alive. It’s one’s duty to travel, to keep moving, to expose oneself to foreign cultures, foreign landscapes, foreign ideas. ~ Brad Newsham

And, of course, I have to add my two all-time favorite quotes which were not included in the journal.

The world is a book and he who stays home reads only one page. ~ St Augustine

When setting out on a journey do not seek advice from someone who has never left home. ~ Rumi



My definition of job security is having a strong, healthy entrepreneurial spirit. That can only occur if you feed yours regularly with activities and thoughts that are nuturing. Here are some of my favorite ways to do just that.

°  Give yourself a change of scenery. It may be efficient for factories to standardize their production lines, but our creative selves thrive on variety.

Take a different route when running errands, take a sabbatical, take a vacation, take your laptop to the park. You can be productive without being routine.

°  Tithe your time. Don’t just send a check to support things you care about. Find ways to share your time.

When Joe started his own insurance agency he decided he’d spend 10% of his time doing volunteer work. Eventually, he worked his way up to 50% volunteer time. Did his business suffer? Not at all. He made so many contacts along the way that his insurance business grew naturally.

This is another way to back up your personal values with action.

°  Create a research project. What would you like to learn more about? Look for a way to fund your research.

Start by checking the grant directories at your local library. You may have a project that someone is eager to fund. Get clear about how this will enhance you personally and entrepreneurially.

You could  find yourself photographing  mosaics in Morocco or interviewing artisans in Ecuador. Use your imagination to come up with a fresh research project that excites you.

°  Share what you already know. Write a tip sheet and get it published—or publish it yourself and distribute it. Mentor a new entrepreneur or a kid. Put your experiences together and teach a seminar.

There’s no better confidence builder than sharing your unique insights and experiences.

°  Find  great entrepreneurial stories. On a flight, I read about a mother and her daughters who started a fascinating business called Junk Gypsies. I was so enchanted by their story that I logged onto their Web site the next day and became a customer.

There are thousands of inspiring stories out there. Make it your hobby to find them. After all, it’s your tribal history.

°  Offer praise. Master the art of writing the exquisite fan letter. Let other people know that you noticed.

After I read Monica Wood’s breathtaking novel Any Bitter Thing, I began planning a review for my local library Web site as well as Amazon. And the author deserves a letter of thanks as well, I decided, to know that her writing has touched her reader.

Catch others doing something good and let them know you noticed. It’s good for them and good for your soul.

°  Learn how to synthesize ideas. We should have learned how to do this in school, but I fear many of us haven’t.

For instance, I was reading Jim Miller’s Savvy Senior column in my local paper. He was asked by a reader how to find a reliable handyman. He offered dozens of suggestions.

As I read what he had to say, I thought that anyone wanting to have such a business could find some great suggestions for marketing themselves using the suggestions in Miller’s article.

It’s equally important to look at enterprises that are nothing like yours and figure out what you can adapt from their way of doing things or their overall philosophy.

° Attend with a friend. I always like to see pairs of people showing up together in seminars. I realize that sometimes a friend comes along hoping to discourage their companion from doing anything foolish.

However, sharing a learning experience with an entrepreneurial friend can be a great way to extend and deepen the lessons learned. There’s nothing like building dreams with someone who gets it.

° Record your journey. Keep an illustrated journal of your entrepreneurial life. Don’t just include the big events; do a photo essay of an ordinary day in the life of your business.

The sooner you begin this, the better. It might become your grandchildren’s favorite storybook. Even more importantly, when we record and acknowledge our own lives, it raises our self-worth.


Although I’ve never conducted a scientific poll, I’m pretty certain that most people would deny that they intentionally set out to have a life of failure. On closer inspection, it’s painfully obvious that many people do just that.

One evening I was having dinner with an inventive woman who had created a successful business in the past. When I first met her, it appeared she was looking for her next good idea.

New ideas weren’t where our dinner conversation headed that night, however. Without any prompting from me, she began a long monologue about why it wasn’t a good time for her to start another business. The list of excuses was extensive.

I listened quietly and when it seemed she was done, I said, “Your excuses aren’t even original!”

Afterwards, I wondered how many people are operating from the same excuse list. I decided to keep track and discovered my suspicions were correct: few original excuses exist.

Hardly a day passes when I don’t receive an e-mail that begins with, “I hate my job,” and then goes on to list all the impossibilities that keep them there. There’s fear, of course, although when pressed to explain, it’s usually a rather vague (or irrational) fear.

Some people have gone a step farther and created an imagined scenario that is filled with dreadful outcomes. To paraphrase Lady Holland, “Fears, like babies, grow larger with nursing.”

If someone truly was committed to failure, I mused, what would they need to do? Here’s a Plan to Fail Formula that I came up with.

° Picture it. Consider this observation from Dr. Rob Gilbert: “Losers visualize the penalties of failure; winners visualize the rewards of success.”

Keep your eyes on all the horrible outcomes that could happen to you.

° Build a team. Who’s going to help you fail? Once you identify those people, spend time with them as often as possible. They’ll convince you that you are undeserving.

Misery really does love company so there will be plenty of candidates for your losing team. Should you accidentally encounter a bold dreambuilder, make your scorn evident.

° Rename things. For instance, don’t tell yourself you’re full of excuses. Call such behavior Being Practical.

Got a job that’s driving you crazy? Remind yourself how fortunate you are to even have a job “in this terrible economy.”

° Collect evidence. We all know somebody who took a risk and it didn’t work out. These stories can be extremely useful when you are tempted to take a risk of your own.

° Take a defensive stance. As Richard Bach points out, “Argue for your limitations and, sure enough, they’re yours.” Make a strong case against yourself.

° Avoid exposure. Don’t investigate new things. Keep your reading list short. Make mundane tasks a high priority.

° Make money the boogie man. Money craziness is rampant. It’s a wonderfully handy excuse. Up your commitment to never having enough.

° Amass unsolved problems. The more, the better. If you keep a problem around long enough, you’ll be able to convince yourself that it’s a permanent member of the family.

° Ignore this. Psychologist Abraham Maslow is remembered as the father of the Human Potential Movement. By all means, pay no attention to this observation from him:

If you deliberately plan to be less than you are capable of being, then I warn you that you’ll be unhappy for the rest of your life. You will be evading your own capabilities, your own possibilities.


The other day my sister Becky sent me an article from her Santa Barbara paper about a creative young entrepreneur named Michael Lewis. His business, Suite Arrivals is an interesting idea, but his entrepreneurial mindset is what got my attention.

One of the things he’s done since setting up shop in his adopted hometown is to create a MeetUp group to connect other self-bossers. “When I started StartUpSB, I knew I wanted to cultivate an entrepreneurial community based on camaraderie rather than business card swaps at networking events,” said Lewis, saying that he’d attended a few such events when he first arrived in town and “they were a nightmare.”

The concept is pretty simple. Participants “show up and make friends with each other, which is far better for the community’s long-term economic growth,” Lewis said. “I spread the word via Twitter and word of mouth at coffee shops, where many local entrepreneurs  work during the day. Now we have 140 members and will soon have the fifth gathering.”

“StartUpSB isn’t big,” Lewis says, “but it’s potent. You can’t measure that potential, all in one room.” He’s passionate that everyone attending has something to contribute. “Each entrepreneur is like one of the X-Men, each with a special forte.”

Later in the interview, Lewis mentions how sad it makes him to see businesses that don’t move forward. He’s convinced that those who make the effort to show up in places that connect them with others on the same path can make all the difference.

It’s something I learned long ago when I watched a tiny little network marketing company grow into a national organization. This was not a get-rich-quick venture and many of those who ultimately succeeded invested a great deal of time before seeing much money.

Because the company was founded by a man who understood much about personal growth, he invented many ways to help people grow from the inside out. One of those tools (although it wasn’t ever called that) was organizing regular company events and meetings.

Since the sales force was scattered across the country, most people had to incur travel expenses to attend. Repeatedly, I noticed, those who invested their time and money were the ones whose businesses continued to grow and flourish.

By regularly gathering with others who shared their vision, they were sending a strong message to both their conscious and subconscious minds that this dream mattered.

This kind of inspiration isn’t vaccination, of course. Repeatedly making the effort to connect and share is an on-going activity for the truly committed.

Sometimes, of course, resistance gets in the way and keeps us away. Who knows what we miss by giving into it?

Comedian Martin Short wrote a wonderful essay in Time magazine about the turning point in his life. He had moved to Los Angeles, but was adrift.

On the day that his own doubts and fears were the strongest, someone invited him to go to an improv show. To be polite, Short accepted, although he didn’t want to go.

He writes, “That show changed my life.The actors were improvising and my mind was going with them. For the first time, I realized that I could channel the way I could be funny at a party into my onstage role. But before that evening, I had never put the pieces together. I had never seen my potential.”

“Isolation is the dream killer,” Barbara Sher reminds us. Fortunately, there’s something we can do about that.

Want to see more of your dreams come true? Transplant yourself into a dreambuilding environment as often as possible.

Gather with others who are passionate and proactive. Make idea gathering your favorite hobby. Listen to inspiring speakers and read eloquent authors who have taken a higher path.

Share ideas with forward-thinking people. Refuse to believe that you aren’t a good investment.

When you regularly show up for your dreams, they’ll start showing up for you. Or, as Steven Pressfield so eloquently reminds us, “There’s power in putting your ass where your heart wants to go.”