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.”

Although the Labor Day holiday has evolved into a weekend that commemorates the end of summer, it began with a very different intention. In an attempt to appease unhappy workers, President Grover Cleveland proposed a holiday to honor their accomplishments. It was quickly and unanimously approved by Congress.

At about the same time, the United States began to evolve from a rabidly entrepreneurial culture to an employee culture. By the time you and I arrived on the planet the conventional wisdom about the importance of finding and keeping a good job was firmly in place.

Having a national holiday to shine the spotlight on laborers undoubtedly has also had the benefit of keeping workers on the job. After all, it’s a public statement that job holders matter enough to have a special day of their very own.

So where does that leave the joyfully jobless? Yes, I know we know we are diligent and committed workers. I also know that our relatives may regard us as slackers. We are not the ones for whom Labor Day was intended.

Several years ago, a self-employed friend joined her former coworkers for drinks one Friday evening.  Although she was looking forward to seeing them, she soon felt bored and disconnected from the conversation.

“The only thing they talked about,” she told me sadly, “was their desire to stay in their jobs until they reached top pay.”

What was this lofty goal that kept them going back day after day? A whopping $17/hour. “That seems to be their only goal,” my friend reported. She never attended another of those gatherings.

However, she did make a diligent and consistent effort to connect with other self-employed people. Instead of finding herself in conversations about top pay, she now was spending time with people who were going places, doing things and making a difference.

“Sometimes I just need to be reminded,” she says, “that being self-employed is a wonderful choice. These days I find myself sharing ideas, getting good advice, and being inspired to set bolder goals. While I really cared about my coworkers from my old job, I know that encounters with them don’t leave me feeling the way I do after hanging out with my new creative friends.”

“Be with those who help your being,” advised the Persian poet Rumi. I often wonder how much happiness, accomplishment and joy would be unleashed if everyone adopted Rumi’s advice.

Since the beginning of 2010, I’ve spent the bulk of my time working on the upcoming Joyfully Jobless Jamboree in Austin, TX. Right from the start, our idea was to create a two-day event where self-employed folks could be with those who help their being.

When we discovered the second day of the Jamboree just happens to be National Boss’s Day, we knew that was a holiday we wanted to celebrate. According to Wikipedia, National Boss’s Day has traditionally been a day for employees to thank their boss for being kind and fair throughout the year.

Alas, many people who have a boss would have a hard time finding little worth celebrating. On the other hand, we who are the boss need to take time to acknowledge the ways in which we’ve been kind and fair to ourselves this year.

So while we won’t be parading through the streets of Austin and no politicians will be stumping at the Jamboree, we will be whooping and hollering and redefining for ourselves what Top Pay means.


Breaking News: We’re extending the Early Bird enrollment until Labor Day, September 6th. Go to to take advantage of this saving. It seemed a fitting way to participate in the holiday.

However, the special room rate for the Jamboree at the beautiful Lakeways Center expires on August 31.

Since my Do Talk To Strangers Policy is a vital component of traveling, I began to consider how I actually go about it. I realized that some of it is purely intuitive. For instance,  when a stranger plunks down next to me on an airplane, I take a breath, take a look and see if I’m moved to start a conversation. Most of the time I get it right. Once in a while, I know  from my opening question that  my seatmate is inclined toward solitude and I stop there. 

Whether you’re standing in line at the post office or waiting for a train, here are a few ideas to help you uncover the fascinating folks around you.

* Make it a game. Decide ahead of time that you want to find an interesting story or inspiring stranger. I have been on long flights that seemed to pass in a moment  because I had landed next to a great storyteller. I consider that a fine compensation for the annoyances of contemporary travel.

* Don’t wait. Instigate. Be willing to be the one who takes the first step. A friendly smile is a good way to test the water. If it’s not reciprocated, move on. 

* Look for common ground. I often open a conversation with a compliment or observation about something the stranger is wearing or carrying or something that’s happening around us. 

When I hopped into a London taxi that was covered in promotional material for the Rolling Stones, I suspected I had a fascinating chat ahead of me. And I did. I learned that my driver was the only cab in the city promoting the Stones, that he earned an extra £750 a year by putting advertising on his cab, and that he’d once advertised for the South African Tourist Board and got a free trip to that country as a bonus. He was hoping he might get tickets to a Stones concert this time around.

* Be politely curious. Our reluctance to talk to strangers may be caused by thinking it’s about us. Wrong. It’s about them. Yes, you might be subjected to a tedious story now and then, but it’s worth the risk. 

One of my most memorable conversations was with a young man who was a linguistic professor who spoke seven languages. When I learned that, I asked him the best way to learn a language and his reply was, “Be a kid.” I laughed and asked, “What’s the second best ?”

Those are the moments that keep me talking to strangers who unknowingly enrich my life.  And like everything else, it gets easier with practice.

It is not he who has lived the longest, but he who has traveled farthest, who knows the most. ~ Armenian Proverb