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.

36 thoughts on “How To Reinvent Yourself

  1. Inspiring as always Stuart! A moment of reflection, a big smile and a mental seed that who knows will grow into a big hairy tree one day. THANKS!!!

  2. Stu,

    I learn so much from your postings. Today I learned new words like “dappled” and “whimsy” and always thought “dumbass” was two words. Seriously, you are the best and you do have courage and more importantly you are a first class human with thoughtfulness and creativity. Having known you all your life I am exceedingly proud of what you have accomplished with so much more in the forefront! Keep it up and L’ shana Tova!


  3. I ALWAYS love your writing and look forward to it!
    You certainly have braved a beautiful and inspiring path for yourself and your family.
    I often question mine! Happy New Year… LOVE

  4. Every day I face my own internal critic, fearful of the world believing: “There’s the dumbass that pissed his life away to make meatballs.”

    But it is friends like you that show me we are to be admired for taking the pay cut. We are appreciated for the sweat and grime we accumulate in pursuit of a vision. We are not summed up by the perceptions of others, nor the internal critics in our minds. We are only our self. And as we near its true authenticity, we approach peace.

    AZ (MKOSF)

  5. Bro – another great thought provoking piece that not only shares who you are, how you ripened and blossomed over time but allows each reader to step back and reflect on themselves objectively. Your writings should be read by a broader audience, NY Times or Washington Post is my vote….. college campuses…. you have a knack….share it with others. La Shana Tova and Love You,
    Mark & Beli

  6. Stu: Inspiring words to hopefully be able to live by. I was always a bit too dumb to ever have a career that involved a suit. It was either salad bar boy at the Chart House or be an artist. Both paid about the same in the beginning of my career.

    Oh, and thanks for turning me on to Michael Jackson. Cool video. That guy’s gonna be big someday!


  7. Stu,
    Another provocative, even jarring piece. Thanks for the jolt. For most of my years in technology I have loved what I do. I recently have found my self searching… Thanks again for the encouragement!

  8. Stuart,

    We worked for a brief time together at IPFONE. This post is ultra-inspirational and really makes people, like me, who work in the everyday corporate world think twice about letting dreams slip away as we conform to the norm. I commend your courage and wisdom you attained. Money can make you happier but it is not everything.

    1. Victor,

      You’re on the right track recognizing the decisions and choices that lead people to escape their chains. But, I might add that it isn’t money that makes people happy. It’s appreciating what we have, at any time, and always, that leads to true happiness. If you happen to have money, then you find happiness in the things you have then. But even those who don’t can be equally blissful merely by being content as they are. It’s the longing for what we do not have the breeds UNhappiness.

  9. There are a lot of blogs out there and only so many hours in a day to read them so I’m choosy. Stories of inspiration like yours help me as I move along my plan timeline: waiting for my daughter to leave for college in 2 years, actually 19 months (not that I’m counting or anything…), finish restoration of my sailboat, and sail it to Key West (from Texas) where I will reinstate my captain’s license. For now, it’s a cubicle where I work on my tan from fluorescent lights humming overhead. Glad I subscribed to your blog, Stuart. You’re a great writer.

    1. Right on, Dave! Call a brother for a coldie and we’ll trade “take-this-job-and-shove-it” stories when you port in Miami.

  10. You just keep doing it – awesome post. Learned a lot about how you got to where you are now, and though my “journey” was more gradual, it was exciting, invigorating and I’m convinced I’m now doing what I was put here to do. No regrets, no looking back (except in gratitude for having made the switch), and I still LOVE what I do, almost 13 years later. You just rock, that’s all.

  11. “Life is long.” BRILLIANT! What a refreshing read and way to start the day. I relayed your blog aloud to my husband over early morning coffee as he prepared for another day chipping away at a career as a developer. We launched into a conversation about our dreams. Star athlete at 48 may be out of reach for him but Sportscaster on ESPN Gameday? Mike IS a dead ringer for Chris Fowler. Perhaps one day soon he can win some contest and sub in! As for my earlier ambitions? I used to tell my grandmother that I wanted to be a maid when I grew up. That or a movie star. Be careful what your wish for! Immersed for sixteen years in a full-time “Domestic Engineer” career after 11 years in advertising, I’m raising (and cleaning up after) two teenage boys and providing more than enough female drama for one suburban household. I’m happy to report that I’m LOVING (almost) every minute of it! Keep ’em coming Stuart. (And GO GATORS!)

    1. Carol – I was a full time domestic engineer the 1st two years of our first child’s life – one of the most critical jobs going. I too loved it and have profound respect for anyone who devotes themselves to sustaining the homestead and the kids’ basic well-being. Bravisimo!!!

  12. Stu, I compltely enjoyed your post as always. I love your inspiration radiance.

    During my senior year at Cornell, while everyone in my business mgt. major was dressing up in business suits and interviewing for Wall St jobs, I was coming to classes in my purple North Face down vest and Merrell hiking boots after roadtrips with friends to concerts and rock climbing trips. I already had clarity at that point that I wasn’t getting on that corporate conveyor belt. I already knew then that I wanted to get a Masters Degree at “Collecting life experiences”, and have proceeded to do so ever since. Now that I’m turning 45 this week, and I have traveled a lot, lived in amazing places in the world, came back to the roots and traditions of my tribe and live in a neighborhood with an amazing international community , have a 13 yr marriage that’s growing strong, am raising and enjoying 4 healthy thriving children, own my home with a beautiful garden, and have close friends that are always learning and growing and are truly inspiring in their own lives…what about the pension? (ROAR of laughter). Seriously, that’s the one unpainted piece of my canvas – I’ve always enjoyed my various jobs, including my current one, but they’ve never included a pension. The price of my life diversity, flexibility, and choices has come with the price of no pension, and just a really modest savings for my kids’ futures. From your vantage point of “going for your dreams” what would you say about the pension? (I’m chuckling as I write)

    1. Dalia, Thanks for sharing! Your journey is rich and dense with adventures, both internal and external. Glad to feel the optimism in your words. As to the pension, that’s a tough one. Money sure helps grease the skids of life. But living on a houseboat showed me I need much less material items than I suspected.

  13. I found your blog through a mutual friend in the Bay Area (Leslie Allen) and have thoroughly enjoyed your posts. Very inspiring and often hilarious. I love to be inspired and to laugh…. thank you!

    (formerly Mill Valley)

  14. I didn’t leave my Sunday night dreading Monday lifestyle until I was 47. The beauty of it though, was that it was a re-birth…to look forward to every day doing what I love doing. I so much enjoy living for each day than just for the two weeks off every year. You write extremely well. I’ve noticed with artists, creative talent spills over into everything. Glad to know you!

    1. Thank You Mace! And bravo to you for getting onto the right track. 47 is plenty young to grab life by the horns, hop on and RIDE!

  15. I’m with you, Sheldon! Instead of going out and getting a job when I graduated from college, I spent five years hitchhiking around the entire globe, finding jobs wherever I could to further me on my way. My daughter Lucia did the same. After college at Harvard and grad school at Yale, she decided to become an actress rather than a Wall Street stockbroker like many of her classmates. Pursue your dream, brother, not the dollar!

    1. RESPECT … tripping around the world is my kind of “post-grad” education. and you instilled that wanderlust in your daughter – BONUS!

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