My kids first paying gig and my first paying gig were very, very different

My first paying gig, as far as I can recall, was in 1991 when I performed as the stripper for a bachelorette party in the crew room of a McDonald’s restaurant in Milford, MA. 

I was unexpectedly paid $100 for the unexpectedly humiliating experience.

You can watch me tell that story here:

Since that day, I’ve worked extensively in the gig economy. 

For more than 20 years, I’ve worked as a wedding DJ, performing at close to 500 weddings. I’ve also worked as a minister, marrying more than two dozen couples and performing a handful of baby naming ceremonies. 

Six years ago, Elysha and I launched Speak Up. Since then, we have produced more than 75 storytelling shows and showcases throughout Connecticut and Massachusetts. 

I routinely get paid to tell stories, speak inspirationally, and teach storytelling, public speaking, and writing in venues all over the country. Theaters. Libraries. Universities. Middle and high schools. Corporations. Nonprofits. Bookstores. Churches and synagogues.

Most would consider my writing career a part of the gig economy. When I sell a piece to a magazine or online publication or sell a book to a publisher, it’s not like I’ve been hired by a company in the most traditional sense of the word. I’ve entered into a temporary employment agreement with a publication that may or may not continue beyond the initial job.

This month I will be paid to perform as a standup comic for the first time. 

But it all started in 1991 in that crew room when I took off most of my clothes and was paid to do so.

This is why I was so damn proud of my kids when they informed Elysha and me that they had  prepared a puppet show for us. In addition to making the puppets out of paper and straws, they also produced tickets for the show. 

“25 cents,” Clara said. “Per person,” she emphasized. 

Clara and Charlie collected our money at the door and performed hilariously for us, whispering directions to one another and sometimes whipping up forgotten puppets on the fly.

Sadly, they are more artists than business people, because they left their quarters on the table and forgot all about them.

But I didn’t. I grabbed those quarters and tucked them away for safe keeping. This was their first gig. The first time they were paid to perform. Perhaps they will not go onto a career onstage as their mother and father have, but maybe they will find their way into the arts someday in some capacity.

Someday down the road, when they can appreciate it more, maybe on the evening of their first professional performance, I will give them back their quarters and remind them of the night they performed for a paid audience for the first time. 

It’s a night I will never forget.