Thoughts From The Road - Part #6

Every December is busy. As a service entertainer I’m typically in high demand for holiday events. This year is no different, but I’m doing a mix of in-person shows and virtual events. (It still feels weird to qualify what sort of gigs I’m working, even though we’re nearly two years into the pandemic.)

There are two stretches of hard days, then the year is over.

First, I’m off to the northwest for an event in the middle of nowhere. The closest airport is three hours away. I take the first flight in and immediately hit the road, with only enough time to stop for a quick meal.

This client is poor at communicating and has left me in the dark on most of the details for tonight’s event. You’d be surprised how often that happens.

Many years ago I flew to an event not knowing the exact venue, showtime, or even the phone number of my contact. But, they’d already paid me so I had to go. Luckily, they pulled through and I made the show happen. I prefer to know everything weeks in advance so I’m not stressed the day of an event. Unfortunately tonight is nothing but stress.

I can’t get ahold of the client, so I pace the grounds pulling on doors of conference rooms. Eventually I ask an employee and they direct me to the correct room. I have an hour to set up before the audience arrives. We’ll be okay.

The audience is great and everything goes smoothly. The client barely says anything to me and I hit the road again. I have to drive three hours to be back by the airport for another flight early tomorrow.

The entire exchange has been so weird with this client that I don’t even ask about the hotel room they neglected to provide me. Sometimes you have to pick your battles.

I break the drive up into sections and sleep in my rental car at a rest stop. It’s not the first time this has happened…and it won’t be the last.


I always get lucky with my flights this time of year and never seem to have cancellations. But, that doesn’t mean I’m not exhausted. These rest stop naps and early mornings have worn me out.

After the show in the northwest I’ve spent the past three days hopping across the country. Six states and four time zones later, I’ve almost neared the end of this stretch.

I catch myself getting frustrated. Little things are bothering me, like the longer wait times at the airport or slow drivers. I’m too exhausted to pull myself together and I end up taking that negativity onstage tonight.

It’s a wasted opportunity to connect with an audience and I head back to the hotel dejected. I can’t sleep so I stare at the ceiling, playing back tonight’s show in my mind. I regret the sarcastic jokes I made and my poor attitude. I promise myself that I’ll make the next show better.

I wake up and get back to Chicago for the last show of the week. And I keep my promise, erasing the previous night’s outing with a phenomenal show.


It’s time for the final week of shows for 2021. I do seven virtual shows in two days, before hitting the road for one last out-of-state event.

I’m still frustrated by last week’s show, so my wife texts me a few minutes before I take the stage: “Stay positive and have a good show!”

It’s exactly what I needed to hear and exactly what I do.


In over ten years of professional entertainment I have NEVER cancelled a show. I’ve performed events around the world and never missed one. I’m very proud of that fact.

Five years ago a fire broke out at the airport in Chicago the night before a show. They shut that location down, along with the other airport here, too. Since it was suspected arson every airport within five hours cancelled their flights out of caution.

Around 11pm I got a text from the airline saying my flight has been cancelled. There were no flights available on any airline and I was dismayed that I might have to cancel the next day’s show.

As a last resort I checked the driving distance. It was 17 hours from Chicago to make it to the East Coast, but I had to leave by midnight to make it happen.

So that's what I did. I drove overnight to get to Boston with only 30 minutes to spare. But I made it, did the show, and didn’t have to cancel. I’m super proud of my track record on reliability for my events and clients.

But somewhere along the way this month - somewhere across the U.S., somewhere at the airport or a Starbucks, somewhere in-between a good show or a really bad one - I got Covid. Always willing to share, I brought it home and gifted it to my wife - an early Christmas present.

She had obvious symptoms or I wouldn’t have known I had it at all. I had no symptoms myself, just a general feeling of tiredness from being on the road. But, to be safe I let my final client of the month know that I couldn’t make it to their event this week. It’s the first cancellation of my entire career.


There you have it.

That’s the entire last six months of my return to live shows put together into six blog entries. I hope you enjoyed this “Thoughts From The Road Series”. Now I’ll be getting back to some standalone essays and thoughts in the coming weeks and months ahead.

I love starting a new year and there’s absolutely no way that 2022 can be any where as bad as 2021 was. Right? I mean, I hope so.

Every year I document every day with video clips and compile it into a video recap, with one second of video for each day of the previous year. I’ve been doing the project for seven years running.

So as we reach the end of last year and the start of another, here is my 2021 Year In Review: