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Starting My Career

MAY 19, 2009
This quick sketch shows the car on the parkway overlooking Westville, New Haven.
I just finished teaching for the semester.  Many of my students are graduating this coming week and will soon start to be illustrators without a net.  It's a frightening time for a young artist.  The soft cocoon of a class is broken and and out they flutter, unfurling their new wings but quickly getting buffeted by the swirling winds of life.
We all were in their shoes at one time.  
In 1987, the week of my graduation in late May, I thought it a brilliant idea to paint my hematoma blue 76 Ford Granada gold.  Armed with some house painting money, I purchased 12 cans of metallic gold spray paint and in 'swirling winds', painted this iron giant gold.
Of course, it wasn't quite the bling I was hoping for, but thinking back, it indicates to me just how care free or silly I was at that moment.
The first order of business after graduation was to pack my portfolio and head off to Jellybean photographic.  I needed my work shot for a hard portfolio (the only kind in existence at the time.)  My senior portfolio instructor, Ken Davies said a few things before I graduated.  He suggested I get some nicer clothes and shoes. My pal Steve Brennan and I decided on the first Monday after graduation to drive in my gold Granada to NYC, dressed in our 'Ken Davies' clothes and shoe's we called, 'cachinkas' for the sound they made while walking.
We boarded the S.S. Granada in New Haven and drove on the Merritt Parkway headed for Manhattan.  Just out of New Haven and the incline out of the tunnel I noticed that the car, never too peppy in the first place, was driving in an odd way.  The power was fading.  It was as if it had a extension cord attached to my home town and I was pulling the plug.
"BOOM"
What was that?
Looking at the rear view mirror I could see a huge cloud of white smoke that shot from the back of the car.  The vehicle died.  I steered this glorious golden paperweight to the shoulder and wondered what happened?  Did I blow a tire, hit something or worse?
It was worse.  The car threw a rod and I could see it sticking out from the pan beneath the engine.
We gathered our portfolios and I left the car on the Merritt.  This meant that we had to either walk home (1987, no cell phones) or scamper down the embankment to the houses below and appeal to someone to help us.  We scampered down in our cachinkas and got covered in dirt and nettles to the unsuspecting neighborhood below.  Door after door these two frightening salesmen went, ringing doorbells hoping for a good Samaritan.  Finally, an older couple let us in.  They believed we weren't going to harm them and let us sit in their kitchen and drink ginger ale.

We called for a ride, the car died and that was that.

I lost a certain care-free attitude that afternoon (thankfully).  I was aware of how silly my gold care was, sitting on the highway.  I had to start to think like an intelligent person.
I soon got an agent, received assignments, and with my older brother Dan's help, bought a truck.   I grew up.



I wish my former students well on your journey and I hope you're all ready for how unpredictable it will be.  Work every day on your art, invest in your career, make connections, and don't give up.


Innocent and foolish pride in a pathetic attempt at standing out from the crowd. I laugh when I see this. Details are funny. One, the car in the garage I bought for parts and the wooden speakers on the back ledge of the car. I do look proud though. Sheesh!
Note the intelligence to wear a respirator. I lost those photos.
It almost gleams. This car was called "Neutral" by my friends. You had to put it in neutral at a light in order to not stall.
1987 Paier College of Art Graduates. Steve Brennan, Tim O'Brien and Mark Castellitto. We are sitting at an opening at the Society of Illustrators, our first. This is 1988.
© 2024 Tim O'Brien