My Freelance Mentor: Mr. Dressup

Photo Credits: CBC

As freelancers we’re always on the lookout for some great advice. As for me, nothing beats the advice from a man known simply as Mr. Dressup.

Ernie Coombs, or Mr. Dressup as he was known to his closest friends, was an American turned Canadian who starred in a long running children’s show in Canada. During his 27 years on television he dispensed some valuable life lessons that I’ve incorporated throughout my freelance career.

Here are a few of them.

Being ready for anything

One of Mr. Dressup’s best known qualities was that he was ready for anything. With the use of an almost magical box that he called the Tickle Trunk, Mr. Dressup could become whatever he wanted.

The Tickle Truck was like a door to another dimension. Later in life I would wonder if it was similar to Dr. Who’s TARDIS. The things he could pull out of that box were never ending.

Was there a need for a fireman? Why look! Here comes a fireman suit out from the Tickle Trunk. How about a dancer for Swan Lake? A leotard and codpiece appears!

The man could be anything.

What mysteries lurk inside the heart of the Tickle Trunk?

So what did that teach me about freelancing?

First, you don’t want to let your clients know you have something called a Tickle Trunk at home. You’ll probably be arrested.

Second, it’s handy to get comfortable wearing a few different hats. Some days you’ll need to be a fireman to put out projects that have blown up. Other days you’ll need to dance around deadlines like Mikhail Baryshnikov. Just reach into that trunk and pull out what you need.

Face your fears

Mr. Dressup lived in a bright and cheery house that well stocked for all types of fun and enjoyment. But it was what was lurking outside that struck terror in my heart every time Mr. Dressup opened the door to his backyard.

I am of course talking about Casey.

You see, Mr. Dressup let out the treehouse in his backyard to a very strange puppet called Casey and his mute dog named Finnegan. What was so strange about Casey is that we could never tell if this ginger-haired puppet with dead eyes was a boy or a girl.

I’ve been having the argument with my brother for over 20 years on whether Casey was a boy or a girl. It’s been so long now that I can’t remember which side of the argument I fall on. Either way, Casey is one scary looking kid.

The eyes...they look right through me

But the fact that he had a clearly unsupervised child living out in his backyard never seemed to phase Mr. Dressup. He would go outside and sing songs or play games with Casey and Finnegan, and I never saw him once ask for the rent or worry about inviting them inside during a particularly cold Canadian winter.

It taught me a lot about facing my fears in freelancing. If I had something like Casey living outside my back door I would probably want to stay inside rolled up in the corner moaning softly. But not Mr. Dressup! Out he would go everyday to face the boygirl.

Walking away from bad clients

No matter how tough Mr. Dressup was, he still knew when enough was enough.

While he no doubt put up with Casey’s hi-jinks for as long as he could, one day, they were gone.

Mr. Dressup said they went away to kindergarten, but I don’t know of many schools who accept mute dogs or strange kids that live in treehouses as students.

I try not to think the worst.

Either way, it was time to move on, and there’s been many times as freelancers that we have to bid a client goodbye. Take a page from Mr. Dressup’s book and send them off to “kindergarten.”