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.