The Caricature Artist!
Making Lemonade Out of Lemons
Estimated reading time: 3 minutes
There you were on vacation at Disney World, or at a Caribbean island resort, or maybe you were at the mall. You were sitting on a stool in front of this caricature artist. He had his easel, a bunch of markers, and he was staring at you! He had this silly-looking smile on his face. You knew he was thinking about how he was going to sketch you in some funny situation.
Hopefully, he wasn't going to overemphasize your big eyebrows or that tiny black mole below your left eye. He didn't want you to see what he was drawing. But your spouse or your kids egged you on with, “This is really funny!” they said. The other tourists waiting their turn were having their laughing fits at your expense! You were worried, but it was okay—you were on vacation!
I was that shabby-looking guy with the long, curly gray hair, the guy with his worn-out rubber flip-flops. I wore my worn-out, frazzled blue-jean cutoffs and a sleeveless T-shirt emblazoned with Jimmy Buffett's “Margaritaville” logo on the front.
Yeah, that was me!
I made being a carefree, overly tanned, single guy living on his sailboat, anchored just off the beach in Key Largo, appear to be the best of all worlds. Most of the time, it was
Back in those days, it was always, “CASH ONLY! No credit cards, please!” I had so many customers that I had to have a take-a-number payment system. My numbered tags hung from a nail I had hammered into the back of my easel.
At one time, I had as many as forty little hole-punched manila paper tags with numbers I had hand-printed myself with one of my black markers!
I charged $15 for a black-and-white sketch or $20 for a colored version. Mostly, I worked on weekends when I was in the city doing a gig at some big convention or a wedding.
But over in the islands, it was all week long, every day, from eleven in the morning to midnight, non-stop. And those “Andrew Jacksons”—$20 bills—just kept piling up in my cut-off jeans pockets!
Business was good, let me tell you.
That caricature business was how I supported five years of living aboard my sailboat. I sailed from beautiful island to beautiful island. It was a good life at that time in my life.
I was in my mid-fifties—a man facing a mid-life crisis and deciding to handle it my own way.
It all started when I discovered that my career was being overwhelmed by a younger workforce willing to work for far less than I had been making as a senior advertising-agency creative director. I was allowed to retire, but the benefit package wasn't exactly what I had hoped for.
So I made a decision.
I bought a beautiful 32-foot sailboat, pulled up my anchor one sunny morning in Annapolis, Maryland, hoisted my sails, and never looked back!
I did it back then.
But now, I've made the big time!
Now I am happily married to my third wife of thirty-two years. I have a nice brick home, a great little dog named Barney, a 10-foot Hobie kayak, a glossy black used 2013 Cadillac SRX, and a full, well-developed beer belly.
I'm healthy and eighty-six years young! Still charting my course. Thank you, Jesus! Life is good!
Middle age? Worried about your future? Woman or man—it doesn't matter, my friends!
Stow away your anchor, hoist your mainsail, and set yourself a new course.
Just do it!
For those who might be dealing with their own mid-life crisis—whatever age that is—remember this:
Sometimes life gives you lemons. Make some lemonade!
A true story by Melton Carr
© 2026 Melton Carr. All rights reserved.