While there are many ways to measure success, one of the best is adding up the number of Firsts in your life. When we’re children, everything is a first. As time goes on, many people simply cease doing anything that is not a repeat of a past performance.

It’s the path to early senility.

How can you experience a life filled with Firsts? How can you find yourself exclaiming, “I’ve never done that before” ?  It may be easier than you think.

Every day living offers an abundance of opportunities to do something you’ve never done before. Drive a new route. Eat a new food. Get to know a stranger. Pick up a book from a section of the library you don’t usually visit. Try a new marketing approach. Write a poem. Wear a color that’s  been absent from your wardrobe. Take a public speaking class.  Plan a business project with a new partner.

While ritual and tradition may be comforting, making a conscious decision to pile up Firsts can be addictive. Doing so can also lead to larger adventures since it’s a guaranteed confidence builder.

In order to bring more Firsts into your life, your imagination needs to be fully engaged. While we all have  random first-time experiences, they can be far between if we don’t instigate them ourselves. Learning to think in new ways, in turn, is vital to growth.

“It is one of the paradoxes of success,” Charles Handy discovered, “that the things and the ways which got you where you are, are seldom the things to keep you there.”

You’ve got to keep creating Firsts if you want to see progress.

The enemy of living this way is the undeservedly popular comfort zone.  While that zone is different for each of us, it’s the place where there are no surprises, nothing unexpected.  It doesn’t build brain cells, it doesn’t stir the imagination. It’s the place where we keep the remote control and emotional control.

Parents often encourage their adult children to live in a comfort zone, thinking it’s a place that prevents worry. There are very few Firsts for those determined to preserve  comfort—which is truly worrisome. The comfort zone is a holding tank; it doesn’t lead anywhere.

No matter where you are nor how old you are nor how long it’s been since you’ve had a First, come up with one right now and do it. Then find another and do it again. Expect that you’ll experience discomfort and welcome it as an ally in creating a richer life, not a sign that you should turn back.

“Those who try to do something and fail are infinitely better than those who try to do nothing and succeed,” said Richard Bird. That’s an invitation to a life filled with Firsts.

My first visit was decades ago when I participated in a whirlwind tour of Europe. We zipped through Venice, were escorted to a glass factory store specializing in selling over priced goods to tourists and whisked away.

I was not impressed.

It wasn’t until 1999, on a short stay with my daughter, that I began to uncover the charms of Venice. Suddenly I understood why artists, poets, writers and musicians kept returning for fresh inspiration.

In its’ heyday, it was a rich and powerful center of trade and business. Poised between East and West, Venice became a city of merchants, many of whom ran their empires from exquisite palazzos designed to serve as their business headquarters, as well as the family home.

A typical Venetian house had an elaborate facade facing the canal since visitors and clients usually arrived by boat. The house was tall and narrow, with the ground floor serving as an office and, perhaps, a warehouse.

The second floor was used to entertain visitors, while family quarters were kept on the third floor.

Many houses also had additions on the street side that were used as offices, but frequently evolved into personal libraries.

So, you see, the homebased business movement isn’t such a new idea after all. The Venetians, who did it more elegantly than anyone, were running international enterprises from their homes hundreds of years ago.

Ponder that on your next trip down the Grand Canal.

Although I think that my siblings are all fascinating people, I sometimes forget what a uniquely adventurous group we are. Until three years ago, getting together was a rare event that insured we were all on our best behavior when we congregate, but I think it goes much deeper than that.

Our siblings are, after all, the longest relationships most of us have. That shared history, no matter how good or how bad, lays a foundation that can’t quite be met by any other relationships that follow.

My sisters and brother aren’t just my longest relationships, however. They are each intriguing people in their own right.

What I like best—and admire most—is that each of them has designed a life that reflects their personal passions and talents.

Just imagine a family gathering with this cast of characters.

Nancy is two years younger than I am and the one who always had the most clarity about her path in life, it seemed. When she was in junior high school, she decided to become an archaeologist.

That’s precisely what she did, becoming a leading authority on Etruscan architecture.

She lived in Athens, Greece, for most her adult life, then spent a decade in Rome before moving back to Santa Barbara at about the same time I moved to California.

We tend to think of her as the scholarly one—she is Dr. Winter—but that’s not the side we see.

Continuously curious, she is always up for new adventures and just paid her first visit to Universal Studios accompanied by my grandchildren.

My next sister, Becky, had the difficult situation of being born the middle child. Maybe that’s why she has a natural ability to organize things. Much of her working life has been spent in libraries, but her organizing skills show up in everything she does from trip planning to running her house.

Like the rest of us, she’s an enthusiastic traveler. The only one of us who is married, she is also the only one of us to have appeared in the Today Show window.

Jim is the lone male in our tribe, but he’s learned to manage it well. Besides being a genuinely nice person who often reduces me to hysteria, he also has seemed the most paradoxical.

A longtime employee of Southern California Edison, Jim is also a talented painter and enthusiastic surfer, continuing to surf as often as the waves cooperate. His gorgeous painting of Italian rooftops hangs above my fireplace, a lovely reminder of one of our family trips to one of our favorite places.

Margaret is the youngest and has a well-earned reputation as the Scrabble player to beat. Besides sharing a love of books, Margaret and I were also single parents of a single daughter each.

Like our father, Margaret is a walking encyclopedia of useful information. If i want to know how to fix something or cure a malady, I check with Margaret after doing preliminary research on Google.

Her home is a testament to her skills as a gardener, woodworker and decorator. She also makes stunning hair fascinators.

Although Becky, Jim and Margaret have spent most of their lives in California, our relationship has evolved even more now that Nancy and I are in the same neighborhood.

Whether we’re gathering for our monthly Second Sunday dinners or planning a museum outing, I always come away thinking, “I really like these people.” Then I notice that my creative spirit feels well-fed.

As Jane Howard reminds us, “Call it a clan, call it a network, call it a tribe, call it a family. Whatever you call it, whoever you are, you need one.”

I laughed and said I knew exactly what he meant. After all, when I was in high school my mother had warned me by saying, “Your problem, Barbara, is that you wear your heart on your sleeve.”

It was not intended as a compliment, of course.

Although I decided not to become a professional poker player, I have created a business that is all about letting me wear my heart on my sleeve.

I’ve been publishing Winning Ways newsletter for 27 years without getting bored. I’m certain my enthusiasm has remained high  because it’s a perfect vehicle for sharing the treasures I uncover in my own Joyfully Jobless Journey.

In fact, a really good business is simply a way to repeatedly share what we love with others.

So it always startles me when I get a friend request on Facebook from someone I don’t know with no profile picture, no biographical information, or, even, a mention of where they live.

In ordinary life, we become friends with people who share our interests or make us laugh or enrich our lives in some way. Over the years, my closest friends have all introduced me to new pleasures and inspired new explorations of things I knew nothing about.

That couldn’t have happened if they kept these passions private.

One of the things I love most about social media is that it becomes another outlet for sharing passions. Anyone of my Facebook friends who is paying attention knows that I am passionate about books, treehouses, and Venice, in addition to being fervent about self-employment.

So this month, I’m going to write about some of those passions on this blog and want to suggest that you consider how things that seem to have nothing to do with your business can actually inspire it.

I love the way Robert Weider puts it: “Anyone can look for fashion in a boutique or history in a museum. The creative person looks for history in a hardware store and fashion in an airport.”

And then they wear it on their sleeve.

Here are a handful of easy ways to get your dreams off to a great start.

° Passion must be present. While a dream may be born in passion, it’s up to you to keep it alive. If you’re halfhearted and lukewarm about them, your dreams will never come true.

One way to keep passion high is to spend a few minutes every day visualizing the successful completion of your dream. How does it look, smell, taste, sound, feel? Allow your vision to keep pulling you forward.

° Take good care of the boss. It doesn’t matter how great a dream is if the dreamkeeper is too tired or uninspired to bring it to life.   Sometimes the easiest things to do are also the easiest to overlook—like drinking plenty of water and avoiding toxic people.

Dreamkeepers have an obligation to create the healthiest and most balanced life possible.

° Make your workspace a place that inspires you. Whether you work on a beach with your laptop or in an extra bedroom in your home, make it inspiring as well as efficient.

Burn incense, play classical music, have a tabletop fountain, and/or cover your walls with art or an inspiration board that pictures your dreams. And if you’re sitting on a beach, pick one with a great view.

° Take responsibility for staying inspired. There are three ways to run a business: Inspired, Uninspired or With Occasional Flashes of Inspiration.

You can identify those things that inspire you and expose yourself to them frequently.   Whether it’s music or the words of a particular author or the company of another entrepreneur, know where your Inspiration Well is and go to the Well often.

° Create your own Hall of Fame. Ask a successful actor or musician who inspired them and they’ll probably answer quickly. Ask a would-be entrepreneur the same question and you’re apt to be greeted by a shrug of  the shoulders.

If you’re going to succeed, you need to be inspired by real people. Read biographies or interviews of successful people and pay attention to the philosophies they share.

° Be open to being inspired at all times. You never know where a great idea or solution to a problem will come from.

Carry a notebook with you at all times so you can jot down ideas as they occur. If you spend a lot of time driving, you may want to carry a voice-activated recorder to capture your thoughts.

° Notice what catches your attention, what makes you happy, what causes an emotional response. These are all clues. Don’t miss them.

° Collect entrepreneurial friends. There’s almost nothing more rewarding than spending time in the presence of kindred spirits who can add their own creative ideas and encouragement to what you’re doing.

Cultivating such friendships will be one of the best investments you can make.

° Change the scenery. There’s nothing that dulls the creative spirit more quickly than daily routine. You can counteract the dulling effect of that by taking a field trip or creative excursion at least once a week.

Take your laptop to a coffee shop, visit a museum or walk in a Japanese garden. Challenge yourself to come up with new backdrops that feed your soul.

Marnie loves the symphony, but with a business in its infancy season tickets are a bit out of reach. That didn’t stop her from enjoying the full spectrum of concerts last year, however.

She became an usher at Symphony Hall and heard every note. In addition, she was paid a tiny amount of money for her services so she was following a favorite rule of the entrepreneur’s unwritten code: find ways to get paid to do what you want to do.

Thinking this way is new to Marnie. She says, “Before I had my own business, I just assumed  I could only do things that I had the money for. Now I look for ways to make things happen in the most creative possible way. Sometimes that involves no money at all.”

There’s a silly scene in Wayne’s World which finds Wayne and Garth lying on the hood of their car at the end of an airport runway reveling in the wake caused by planes taking off.

Mike Myers says this scene was inspired by a favorite pastime in his family called No Money Fun.

The idea was to come up with entertaining activities that didn’t cost a cent.

When I heard Myers tell the story, I thought, “No wonder he’s so creative. What a great thing to learn early in life.” No Money Fun is a terrific way to activate the imagination and it comes with the built-in reward of all that free fun.

There are two ways to bring more No Money Fun into your life.

You can take advantage of all the free things around you such as strolling through a beautiful public garden or museum.

The other option is to use alternative currencies. No, I’m not suggesting you take up counterfeiting. I am, however, challenging you to become as creative as possible about finding alternative routes to have and do more of what you want.

This is not about becoming a certified cheapskate, however. In fact, you’ll notice that the wealthy are masterful at using alternative currencies in place of cash.

Cheapskates, on the other hand, pride themselves on deprivation. The other caution is that you only use alternative currencies to acquire things you actually want or need.

So how can you cultivate alternative currencies? Begin by refusing to ever, ever use lack of money as an excuse. You can only master this if you understand that this is a practical exercise in creative thinking and living.

Start looking for options—and open yourself to offbeat ideas.

Let’s say you want to live in a gorgeous home. Most people think that their options include buying or renting. Don’t tell that to Joe.

When he was in his early twenties, he found himself drawn to the ocean and wanted to live as close to it as possible. He got the idea to offer his services as a yacht sitter and almost immediately found himself living in luxury.

Or perhaps more travel is on your Dream List. Jan is a bookworm who published a newsletter for cozy mystery lovers. Next to books, her other great passion is England.

For nine years, she organized and led Cozy Crimes, Cream Teas and Books, Books, Books tours to the UK creating a free trip for herself and a delightful experience for other mystery lovers.

When creating innovative ways to get more of what you want, it’s essential that you design mutually beneficial arrangements. For instance, Joe didn’t just get a great place to live, he provided security for the yacht owner.

There’s an even bigger benefit in all of this, one with longterm rewards. Mastering No Money Fun is first and foremost an exercise in learning that there’s never just one way of accomplishing things.

It can banish uninspired thinking and open up a new world of creative possibility.  Best of all, you’ll be living your life from a position of abundance and imagination.

What business wouldn’t be better with that kind of thinking running it?

Marianne asked me and several others to answer in a sentence or two the question, “What do you wish you had known when you were eighteen?”

I began thinking about my eighteen-year-old self and realized that like most people that age, I was busily trying to figure out what I thought.

What kind of life did I want to have for myself? Was it easier to settle for an uninspired life or listen to the promptings of my heart?

I do not recall anyone suggesting that I should learn to think for myself.

As I began to jot down ideas for Marianne’s project, my list got longer and longer. How would I ever be able to pick one thought that summed up all the missing pieces of my puzzle?

What did I wish I’d known when I was eighteen?

Here’s my partial list:

Adventure Trumps Comfort.
Forget the Notion of a Single Lifetime Occupation.
Invest Wildly in Your Self and Your Dreams.
You Can Have Your Excuses. Or You Can Have Your Dreams. You Can’t Have  Both.
Caution is Highly Overrated.
Take Every Opportunity to Astonish Yourself.
Fun is Not Frivolous.
What Makes You Different May Be What Makes You Valuable.
Don’t Waste Time Solving Problems You Don’t Have

I knew none of those things when I was eighteen—or twenty-eight. While I was deliberating about which of these things I wanted to share, Marianne came to my rescue and said to use them all and she’d decide which were the best fit for the project.

That got me off the hook, but doing the exercise had triggered a new thought.

What would happen if such radical notions were adopted early in life? What if  we were encouraged to define adventure, dreams and opportunity for ourselves? What if we assumed that a lifetime was well spent if we kept stretching ourselves?

My question was answered when I happened upon a story of Justin Churchman, a CNN Hero. Justin set a goal to build eighteen houses in Juarez, Mexico before his eighteenth birthday.

After he participated in a building project with his seventh grade class, Justin got busy writing letters, giving speeches and working to raise more than $48,000 for Casas por Cristo. He also picked up a hammer himself and finished building his eighteenth home on his birthday.

Inspiring as Justin’s story is, I suspect that plenty of people who saw it reacted by thinking, “Well, that’s fine if you’re eighteen, but I couldn’t start such a thing at my age.”

Ah, age. It’s often the scapegoat for our fondest excuses. That’s not the way a card-carrying dreambuilder thinks.

Dreambuilders are apt to prefer this reminder from Robert Pirzig: “There is a sanity within me that reminds me that to regret that a journey wasn’t started sooner only delays further its beginning.”

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The aforementioned Marianne Cantwell was featured in a nice piece in London’s Daily Mail. Read more about her journey from cubicle dweller to free range human

In 1951, he taught himself to type with two fingers and began writing down his stories. His wife corrected and retyped the book. Then Swan optimistically sent his manuscript to several publishers. They all turned him down.

Discouraged by the rejection, Swan packed the manuscript away for ten years. But the dream of publishing success wouldn’t go away and Swan got the idea to publish it himself.

He mortgaged his house, bought a computer which his wife learned to use, and bravely ordered 1,000 copies of  his book titled  Me ‘n Henry.

His exhilaration dimmed somewhat as he tried to interest shopkeepers in carrying his beloved journal and found few takers.

He managed, however, to sell his first 1,000 copies and that was all the encouragement he needed. There’s got to be a way to sell even more copies he reckoned.

What if he opened his own bookstore? He scouted around the near ghost town of Bisbee, Arizona and found an empty space next door to the town’s only bookstore. It was just what he was looking for.

Before long, Walter Swan became a bit of a celebrity. His One-Book Bookstore brought him loads of national publicity. Tourists began going out of their way to meet Swan, buy his book and have their picture taken with the author. Swan’s creative problem-solving might be the best story of all.

Many years ago, Ralph Waldo Emerson observed that everything has its price and if that price is not paid, you will not receive the thing that you desire. Walter Swan figured out the price of his dream and made the necessary sacrifices to achieve it.

Do you have dreams that don’t seem to be coming true? Maybe the price of your dream is to be open to more options.

When people go from being an employee to being an entrepreneur, they often bring along a belief that doesn’t serve them well. Having spent years having a single source of income, they think their business will also come in only one way.

That’s not the way it works. The excitement of being an entrepreneur is that no such limitation need exist.

So remember Walter Swan the next time all doors seem to slam in your face. You may just need to keep exercising your imagination and opening yourself to fresh options until you come up with an original and unorthodox approach to solving your problem.

As long as you don’t stop believing that there’s always a way, your own tenacity will lead you to far greater things than you first imagined.

It appears that anyone who ultimately achieves their dreams has a clear idea what the trade-off was that was needed to accomplish it. It’s a characteristic often lacking in those who attribute their lack of success to bad breaks, circumstances over which they had no control or lack of money.

Money, in fact, becomes a popular scapegoat in stories about failure.

Most often, however, our dreams are created out of time, not money. In Jean-Louis Servan-Schrieber’s The Art of Time, he makes this startling observation: “We think much more about the use of money, which is renewable, than we do about time which is irreplaceable.”

Here’s the fascinating—thought often overlooked—truth about what we get in life: everything we have, whether we are living our dreams or not, is acquired by making a trade.

We trade our time, our talent, our experience, our attitudes for the lifestyle we create. Sadly, many people also trade in their dreams, settling instead for a less than satisfying life because it may seem easier or quicker to achieve the ordinary.

Nowhere is this more poetically illustrated than in Paulo Coelho’s little gem The Alchemist. The hero of this tale is Santiago, a young Spanish shepherd, who has already traded in his parent’s dream for him of becoming a priest for his own dream of traveling.

Along the way, he encounters a wise man who prods him to achieve his personal destiny. To add motivation, the wise man points out a number of people who traded in their dreams for a seemingly secure life.

One of them is a shopkeeper who resists his lifelong dream of a trip to Mecca. At one point he says to Santiago, “Today, I understand something I didn’t see before: every blessing ignored become a curse. “

What the shopkeeper demonstrates so poignantly is a universal truth. When we trade off our dreams for a lesser life, we are doomed to unhappiness.

On the other hand, if we trade off our fears and doubts for our own dream quest, satisfaction and joy that we have never known before are inevitable.

So is there anything you still need to trade in order to be living your dreams? Since all life is a trade anyway, why avoid what you really want? You’re already spending your time and energy doing something. Make it count.

Don’t you think dreams are a better investment than drudgery?

I remember that I loved the seminar but really was at a place where I thought the ideas would work for anyone but not me. I had very low self-esteem in the area of work because I kept choosing jobs that were a poor match.

This was how I thought my life was going to be: just grin and bear it and accept that I would never live my life from a more authentic place. So I kept working these draining jobs, going to therapy, completely stressed about money all the time.

And yet, there was a part of me that would not give up.

My husband saw an ad for an innkeeper. At the time, I was working at a hotel as a front office manager on Cape Cod and was so miserable. I called and the owner said he was really not looking for an employee, but a business partner.

We were not ready to lease the inn, so we offered to run the inn as independent contractors and had a legal agreement drawn up. Now, basically, we work for ourselves and get a decent percentage of what we bring in.

We run the inn how we want to and we are truly having the time of our lives. We both get to use our skills and because they are so different they compliment each other well.

My husband says that he feels alive in a way that he has not in a long time. We just discovered new space behind the inn that we will be turning into retreat/meeting/yoga    space.

It is so funny because now I am never sure how much money will be coming in week to week and it is the thing I worry about least.

I am having way too much fun working hard and now believe that the Universe will provide me with everything that I need because it already has.

Cheryl Bagangan, Onset, MA