Set the Stage for Your Endless Career: The First Four Steps

California Chrome
California Chrome

Art Sherman talks with his hands as if holding the reins, a distinctive trait left over from his first career as a jockey.

Riding for over 21 years he rode his share of winners, but rarely the big horses in the big races. He’d occasionally supplement his income playing “race-horse rummy,” a card game that was popular in the jockey’s room between races, for 25 cents a point.

Fifty-five years later Art Sherman was in the winner’s circle, as the trainer for California Chrome at this year’s Kentucky Derby, hallowed ground for equine greatness.

California Chrome won by 1 ¾ lengths fostering hysteria for The Preakness Stakes, the second race for the Triple Crown. On another gorgeous Saturday afternoon last weekend, Sherman’s horse won again in a magnificent race.

Kentuckians, far removed in time and space like me, watch the Derby the first Saturday in May without exception. Sure we choke up as we sing ‘My Old Kentucky Home’ because at that moment memories flood our hearts, but when a horse like this comes along we can turn giddy.

California Chrome now has a shot at Triple Crown greatness, but you have no soul if you don’t root for Art Sherman too. His story is an advanced class on finding what you love to do and day-after-day-after-day turning it into an endless career.

This unassuming man is the oldest trainer to have won the Derby. “I never made it with the big, big horses…but I’m thankful for my career,” Art said.

Bring It Home Chrome

Sherman’s second career as a trainer began in 1980 working the California circuit. As was the case with his riding career, most of the victories were small and unremarkable.

Sherman is ‘old school,’ training the same way for over thirty years and it’s for that reason he is now at this astonishing point in an endless career.

“Small barn. Old time. Old school. Old rules. Every horse is an important horse (to Art) and he takes quality time with each one. We knew we had the real deal for this horse,” said Steve Coburn.

Victor Espinoza wearing Dumb Ass Partner's silks after winning the Derby.
Victor Espinoza wearing Dumb Ass Partner’s silks after winning the Derby.

Owners, Steve Coburn and Perry Martin, bred a mare purchased for $8,000 – chump change to the bluebloods of the racing world but not to a couple of working guys. Her first foal was California Chrome.

People called them a “couple of dumb asses” for investing in that mare so they named their partnership Dumb Ass Partners. A donkey is on the back of their racing silks.

Stories about these average-Joe, underdog owners captivate, but it is Art who has become the lovable leading man of this year’s elite horse racing.

The media portray him as the Everyman trainer who just works hard to win the run-of-the-mill races. At 77, he has slowed down; his operation has 17 runners instead of 50. But unlike many ordinary individuals who reach 65 and check out of a career, Sherman disregards the option.

When asked about retirement, Sherman said, “What’s that?”  He’s not being clever, he’s being honest.

“It’s not in my vocabulary, that word ‘retirement,’ “he said. “I love the action. I like the challenge of coming up with a good horse. I like buying 2-year-olds. It gives you something to look forward to.”

Choosing Traditional Retirement is Not Cool

Art Sherman created an endless career by changing paths within one industry to continue work he loves ignoring a traditional path of retirement.

For many of us looking past midlife, Sherman’s story is enviable because we haven’t found work we love and he has. Is it easier to extend a career arc when you’re engaged in work that brings you joy every day?

The answer’s an obvious ‘yes.’

If you’ve unconsciously found yourself stuck in unsatisfying work or grown stale in a vibrant high achieving career, an ‘endless career’ is less definable – and a transition is inevitable. Career reinvention can be chaotic and time consuming.

I think for many it’s easier to retire like everyone else, rather than start down the long, arduous path of “career exploration.”

Plus ‘retirement’ is still a respectable option especially if you tell people you plan to give back to “make the world a better place.”

But soon it won’t be cool. With 30-plus bonus years ahead there’s ample to time to create a life of freedom, work and finding ways to devote time “for the greater good.” The word, ‘retirement’ isn’t in Sherman’s vocabulary for a reason – it doesn’t fit any more.

Vibrant lives, endless careers, travel, freedom – inventing a life you love. That’s the future.

And one other thing.

While the most compelling reasons for a second career late in life are to create meaning and purpose, there’s no reason to surrender financial reward.

Sherman gets paid for the work he does and now, of course, he’ll have more money than you and I will ever have. And he may just use some of it for “the greater good” thus combining an endless career with financial reward and giving back.

“Do what you love and make it pay,” advocates William Keiper, author of the award winning book, “Life Expectancy: It’s Never Too Late to Change Your Game.”

If you are in your 50’s or 60’s the gateway to the journey to an endless career is waiting to be explored. But the majority of people I talk with want to start with the question: “What will I do?”

It’s a good question but the timing is off – way off.

Only 11 horses have won the Triple Crown. California Crown runs The Belmont on Saturday, June 7th. Admission is $10.
Only 11 horses have won the Triple Crown. California Crown runs The Belmont on Saturday, June 7th. Admission is $10.

First Four Steps to an Endless Career

An endless career is not a job change but a career reinvention within the context of life with an expiration date closer than ever before.

While you can’t think yourself into a new way of being, your internal story line – what you tell yourself about you, you-getting-older, work, possibilities, odds, chances and prospects –  either reinforces or grinds down aspects of meaning, vibrancy and direction for your future.

Can you see yourself at 75? How do you spend your days? What is your work? What are you trying to do with your life? Who is important to you? Where do you live? How many hours do you devote to a career? Do you love your life?

Answers to these questions showcase the implicit assumptions you hold today. A deliberate inquiry and deep shift in perspective can change the course of a future life; this is the invisible work to focus on.

Before you craft a list of possibilities for an endless career or invent a future life to take you into your 90s, challenge yourself with these four steps:

1. Own the ‘New Spirit of Aging.’

Aging with vibrancy and good health isn’t a pipe dream any more so there’s little reason to emulate your parent’s or someone else’s choice of how to design life. Your implicit assumptions about aging and productive longevity link directly to what you will allow for your future. Does your philosophy for living past midlife encourage you to begin a new career, become an entrepreneur or continue in your high-achieving one? Do you question the logic of the outdated construct of retirement? Are you heaving yourself into the trend of social purpose as the only pattern for life at 70?

2: Pay Attention to Guiding Figures.

You are a newcomer to a possible new way of living the last thirty years of life where there are few insiders. You’ll find no mentors, but you can find pioneers who are carving out new ways of work and life. While stories like Art’s abound in the media, there are also extraordinary people who are not choosing traditional retirement but inventing awesome lives. Look around and you’ll find them in your company, as colleagues or friends of friends. Ask for a moment to have a conversation and find out how they navigated the choices for late-in-life design. Cultivate ideas to springboard your own. Be inspired.

3: Establish a Firm Persuasion toward Career Reinvention.

Your working identity is an integral part of who you are; the consummation of work at 60 or 65 is only a milestone that reflects what you have done so far. It is not your future. Changes in the kind of work you want, the hours involved and places you can work from create unknown options. While you may not fully embrace the idea of an endless career, be intent to explore one. You may or may not carry through but that’s not the point. Make ‘an endless career’ an undercurrent in possible future life design Post50 to ensure you’ll have no regrets. And so you won’t have to eventually ‘un-retire.’ (ugh)

4. Acknowledge Head-On that Revenue Matters.

Do you buy into the idea you should stop working, quietly retreat to the edges of the cocktail conversation and never receive a paycheck again? Really? How come? While getting out of a demanding career might be a choice, why not choose work that fits an innovative life you design and has the potential to make money?

It’s a new world – one where you’ll need and want the money for yourself or others. A world that is unpredictable and scary. A world where health issues, grandparents raising children and extreme weather events rock lives and the finer things in life you still desire (they don’t just disappear when you hit 60!) cost more than your financial planner thought to mention.


At Belmont Park Art Sherman wears his iPhone on his belt, and when it rings, as it has a lot lately, he answers, “Yo.” He sprints to the track each morning to watch his horse and then rushes back to the barn to supervise the colt’s meticulous bath routine. Sherman feels young again. (Two Horses, 59 Years Apart Inspire One Trainer by Melissa Hopper, New York Times.)

The Van Lear Bridge, Eastern Kentucky. I can't count the times my mother got out of the car on this one-lane bridge to tell the driver of the other vehicle she met head on, "I am not backing off this bridge." And she never did.
The Van Lear Bridge, Eastern Kentucky. I can’t count the times my mother got out of the car on this one-lane bridge to tell the driver of the other vehicle she met head on, “I am not backing off this bridge.” And she never did.



Photo Credits:

 California Chrome,

Art Sherman, Jen Reese, Courier-Journal

DAP Silks, AP Photo, David Goldman

2014 Derby,

Van Lear Bridge, 1950s by Dean Messer


About Barbara Pagano

Barbara Pagano,Ed.S., author and speaker, influenced over 3,500 executives in organizations to achieve higher performance. She is now on a mission to help individuals extend their career arcs and craft lifestyles of productive longevity.
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