Starting Over… at 65

On my way to a meet a potential client in Manhattan the other day, as I approached Robert Indiana’s iconic LOVE sculpture at Sixth Avenue and 55th Street, my mind played a trick on me. It suddenly whisked me back 38 years, to when I was a 27-year-old aspiring writer ready to make my mark in New York.

I’d spent the previous decade in Philadelphia, getting my bachelor’s and master’s degrees in communications and journalism, and renouncing conventional work life for a romantic but exhausting existence of freelance writing by day and performing as a singer-songwriter at neighborhood bars by night. After several years of burning the candle at both ends, I had three things to show for it: a portfolio full of stories, co-writing credit for a movie soundtrack song that was recorded by a famous Motown artist but stalled just short of the $2,000 mark in royalties (my last check was for 12 cents), and a chronic cough that put a crimp in my folk-singing career.

With my musical ambitions on hold, and my trusty Remington manual typewriter in toe, I hopped an Amtrak train to Penn Station and stepped out into a Manhattan buried in more than a foot of snow and shivering in record-setting cold. Luckily, a cozy, one-bedroom, rent-controlled apartment awaited me just a few blocks away. It had been bequeathed to me by an aunt and uncle who’d retired to Florida. It was then, in February 1979, and there, in that little apartment in the middle of the big city, that my adult life officially began.

Pounding the Pavement

Prepared to pound the pavement as long as it took to get hired as a writer — or so I first thought — I was inspired by the encouragement of an English Composition professor who had called my work “publishable,” and a graduate school mentor who had told me I was one of his top two students.

I considered myself confident but realistic: I didn’t set my sights on becoming the next Philip Roth or Paul Auster, as much as I idolized each of them. I wasn’t pursuing The Great American Novel –just a job writing for a well-known newspaper or magazine.

After a few months of trudging the city’s streets, though, I’d gotten little more from the editors of Rolling Stone, The Village Voice and New York Magazine than invitations to submit stories on speculation. The life of the struggling, starving artist was looking less and less appealing, and I wound up working for a small financial publisher.

The next three years were my incubation period in New York. I found my footing, built a social life with friends from the office and, most importantly, paid the rent. But the work wasn’t challenging or fulfilling. It was in the ball park, but just not close enough to what I really wanted to do.

Then, through an ad in the classified section of The New York Times, I found an entry-level job in public affairs at the U.S. headquarters of a multinational health care company. Given the opportunity to write speeches, position papers and company magazine articles, work with the media and manage crises, I may not have hit the bull’s eye, but this was pretty close. I stayed with the company for 35 years, eventually working in executive positions on both sides of the Atlantic and seeing a big chunk of the world.

When I look back, I have to laugh at the question the hiring manager asked with genuine concern at our first interview: “Why should we take a risk on you when you’ve never stayed in a job for more than three years?”

I told him that once I found a place where I could do what I was good at and be valued and well-compensated for it, I’d stick around. He bought it. And stick around I did, for more than three decades — all the way into the next millennium.

Fast forward to 2017. Now I’m a 65-year-old aspiring writer, ready once again to make my mark in New York, this time after spending the last decade-and-a-half at my company’s global headquarters in Switzerland. I finished my career there last December and returned to New York with a pension and savings account sufficient to support a comfortable life for my wife and me. This time around, I don’t have to worry about starving, but I may well have to struggle to fulfill my ambition of building an encore career as a creator of all sorts of content, from essays and case studies to feature stories and books. Or maybe “struggle” is the wrong word, expressing the wrong attitude. Maybe the word is “strive,” or “persevere.” Coaching types tell me to look at it as an adventure.

Pounding the Pavement, Again

So that’s how I looked at it, as I pounded the same pavement in search of rewarding writing work all these years later. The LOVE sculpture loomed before me on the sidewalk like some monument to the child who’s father to the man.

Just across the street, on the 30-somethingth floor of the stately skyscraper on the corner, a business prospect awaited — the CEO of an investment banking firm in the midst of a rebranding effort and looking for help producing content. A few minutes later, the formidable executive brusquely asked me, without preliminary chit-chat or pleasantries, “So, what do you think you can do for us?”

The 27-year-old me might have stumbled, having less life experience to shore up his self-confidence, and no Google at his disposal to investigate the company and its chief executive before the interview. The 65-year-old took it in stride and earned the CEO’s commitment to give him serious consideration for future projects.

I’m supposed to follow up next week. A paid assignment may or may not follow. Other prospects who promised me work have not come through, and maybe they never will. I had my hands full with work from July through October, and came up empty in November. People in the independent writing business tell me it’s “a life of too’s: too much or too little.”

A Tip from Philip Roth

The too-little part is where the difference between struggling and striving comes in, and perseverance is key. It’s like my idol Philip Roth told Esquire magazine in 2010, two years before he announced his own retirement following publication of his 24th and final novel, “Nemesis.” In an interview I’ve never forgotten, Roth explained how he dealt with the struggle writing can be, but his advice applies to a much wider range of endeavors.

Roth told Esquire he had a mantra that helped him get through tough patches when things just weren’t flowing. “I have a slogan I use when I get anxious writing, which happens quite a bit. ‘The ordeal is part of the commitment,’ ” he said. “It makes a lot of things doable.”

The magazine’s interviewer had a slogan of his own that has stuck in my mind as well: “Mine is from a fat relief pitcher, Bob Wickman,” said the writer, Scott Raab: “You gotta trust your stuff.”

To me it means keeping the faith. Believing in yourself. Hanging onto your confidence in the toughest of times and continuing to persevere and carry out your process, stick with your plan, come hell or high water.

The 27-year-old me hadn’t learned that lesson. The 65-year-year-old is retaking the class, hoping to master it this time.