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  • Writer's pictureStuart Sheldon

How To Reinvent Yourself

Small Steps in a Big World, acrylic and antique cookbooks on canvas, twelve 5"x5" squares, 2007, Stuart Sheldon

Small Steps in a Big World, acrylic and antique cookbooks on canvas, twelve 5″x5″ squares, 2007, from the collection of Peay Vineyards, Stuart Sheldon

We so often mistake familiarity for happiness and routine for satisfaction.

Twenty-five, chiseled and ready to party, I stood forearms perched on the railing of a ferry to the Greek isle of Paros. Dance music played and gusts of laughter from fellow travelers engulfed me. The world was mine … but for one thing …

I Felt Utterly Despondent.

How could this be, I asked myself. Then, as I watched dappled moonlight dance on purple-black water, one of those few-in-a-lifetime gongs that changes everything rang inside me. Up until that moment, I’d been living what I call the “conveyor belt mentality.” You step on as a schoolboy and let life happen to you: corporate job, training, promotion, girlfriend, wife, suburb, kid, white picket fence, 2-week vacation, gold watch, et al. My job as a stockbroker had found me, not the other way round. Standing beneath Odysseus’s sky, I saw for the very first time that I could be whatever I chose: a doctor, a paleontologist, a shop owner, a circus clown. My despair at that ship’s rail stemmed from walking on the wrong life path. And no amount of external beauty and youthful revelry could change that.

But I could change that.

On my 27th bday I walked out the door of my Brooks Brothers life as Vice-President of Investments. I started my MFA in Film the very next day, smiling ear-to-ear in shorts and a tee, as I stood on the pedals of my bike and rode toward my actual dream versus the dream I thought society expected of me.

1991 Michael Jackson Black or White image courtesy of

1991 Michael Jackson Black or White image courtesy of

A year later I was in LA holding a production assistant walkie-talkie on Michael Jackson’s Black or White video while scribbling away at home on my first screenplay (which was horrifyingly terrible and will never be shown to anyone). But my reinvention did not end there. Film merged into writing which became magazines which bled into fine art. Now, I’m father and artist, two sides of the same coin, both of which I approach with whimsy and sanctity … and both of which are utterly open-ended.

If you wanna hit the target, you gotta pull the trigger.

Don’t think for a second it was easy. The choice to leave that finance job kept me up at night for YEARS, mortified that I was throwing away a life of certain wealth and privilege and all the things America seems to value most. I thought everyone would look at me with disgust and pity. There’s the dumbass that pissed his life away to write poems and make silly movies. Still, I could not deny the nausea and anxiety I felt EVERY SUNDAY NIGHT knowing that I had to suit up the next day and play a game I loathed (all due respect to my friends still in the biz).

Our stomachs don’t lie!

But what about those with little or no flexibility? The minimum-wage factory worker or the maid who has no choice? Or my single mother, who worked full time as a teacher and got her masters at night? Of course, I have only humble admiration for these selfless HEROES. I recognize that many dissatisfied hard-working souls must pay the bills and feed, clothe and educate their kids today and tomorrow and always. There is never a good time to make a change that introduces hardship. BUT, if you’re reading this, you’re most likely a middle-class person who DOES have more choice. To you I say …

When it comes to doing what you are BEST SUITED for, MAKE IT HAPPEN BY ANY MEANS NECESSARY.

Sad as it is, most of life in America is work. So, devoting 2000 hours/year for umpteen years to something whose sole benefit is money seems not only painful but short-sighted. Sure, I was single and free to act impulsively when I switched gears. If you don’t have that freedom, take baby steps. If you’re selling insurance but really want to be a radio DJ, volunteer at a station at night or start a podcast. If you hate your life as a DJ and want to make real money in sales, put your head down and attack; it’ll take a few years to build a client base, but LIFE IS LONG and plenty of things need to get sold. Oh, but there’s no time … Let me repeat …


What amazed me was that, with the exception of my boss at the brokerage, who felt abandoned after he groomed me all those years, every single person the past 20-plus years applauded my choice. Told me they wish they’d done it. That it took courage to chase one’s own true north. The most courageous step is the one off the diving board. After that one, gravity takes over. So, take that step … and make your life bigger than it might be. You MUST do so if that opportunity exists.


It’s YOUR life. And your joy. I can tell you that I’m feeling happy as Hercules every Sunday night these days.

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