How To Balance Joy & Loss? A Young Creative’s Life In Fashion Provides Clues We Can Use

Note: This post was contributed by Bill Dixon, wise grandfather and former journalist.

Joy and loss. They go together more than we would like to admit.

We pursue objects and experiences in hope of achieving joy. But all too often, the achievement slips through our fingers, leaving behind a sense of loss. If we are fortunate, we learn to accept that our joys are fleeting. And if we are really lucky, we find in ourselves the ability to hold onto our joys and put our losses into a healthy perspective.

Some of us need many years to make that discovery. I put myself in that group. Who am I? Kylee’s 70-year-old grandfather, whom she has asked to contribute to her blog. My first contribution is inspired by someone who found the joy-loss balance as a child and cultivated it for the rest of his life.

Bill Cunningham was a designer and fashion photographer who became a global cultural icon before his death in 2016 at age 87. I first encountered Mr. Cunningham’s work through the New York Times website, which posted his self-narrated videos of everyday life in the city for many years. These were a revelation, allowing me to experience New York through its changing seasons and clothing styles, played out on sidewalks and in parks.

Each story was told with gentleness and wonder. When Mr. Cunningham’s memoir, Fashion Climbing, was published this summer, I ordered a copy.

What I found in the book was a man who combined creative brilliance with courage and hard work throughout his life. I also found lessons that I hope to apply in my life.

From loss, carve the path to a new joy

As he tells it, Mr. Cunningham fell in love with fashion as a 4-year-old. He started by wearing his mother’s dresses. When a vigorous spanking showed him the limits of that enterprise, he began designing costumes and staging pageants for family holidays. He found ample inspiration during weekly Mass, where he spent much of his time observing what fashions the women of his native Boston were wearing.

As soon as he was old enough, he went to work for a department store, where he learned how good clothes were made as he delivered them to the display racks. After high school, he enrolled in Harvard but was miserable.

To the dismay of his parents, who had wanted him to become a priest, he dropped out and moved to New York. There he found a department store job and started making hats for fashionable women in his spare time. In less than two years, he built a successful millinery business.

This was a pattern that he was to repeat throughout his life: He shrugged off a temporary loss and refocused his creative energy on bringing joy to others.

Mr. Cunningham’s next opportunity came at the age of 21, when he was drafted into the Army and lost all that he had built.

Persistence and joy go hand in hand

As he puts it, he was “heartbroken.” But instead of bitterness at his abrupt change of fortune, he found new inspiration. During basic training, he made a name for himself -- and got lots of punitive guard duty -- by decorating his helmet with flowers. After basic training, he was posted to France, where he took side jobs making hats for a Paris designer and organizing bus tours around Europe and North Africa for his fellow soldiers.

Mr. Cunningham says in the book that he was never one to dwell on a setback. Instead of focusing on the loss, he looked for the opportunity.

After the Army, he rebuilt his hat business and became a leading designer. When hats went out of style, he became a fashion reporter, covering style trends coming out of the leading American and European designers. When his boss at a fashion magazine refused to run a Cunningham article that criticized on of the boss’s favorite designers, Mr. Cunningham quit and became a free-lancer.

Hard work/hardship is its own reward

In the late 1960’s he sensed that fashion no longer was under exclusive control of the design houses and expanded his focus to people on the street. He spent the rest of his career chronicling both. And his focus was always on telling the fashion story his way.

He lived much of that time in a studio apartment, sharing a shower with other tenants and sleeping on a cot. He rode a bike all over the city. He did everything he could to live frugally because he believed that depending on money would destroy his independence.

And did he ever work. To chronicle the city’s evolving fashions he went out in all kinds of weather, and spent hours making sure he had the shots he needed.

It wasn’t an easy way to make a living. Thirty of his bikes were stolen or wrecked. He had to dodge the city’s notorious traffic, and once was hit by a truck. But he kept at it enthusiastically.

Mr. Cunningham’s life is full of examples of this extraordinary fellow making a creative success out of repeated setbacks and outright poverty. And doing it with grace. How does that happen? How does a Bill Cunningham hold onto his joy and put his setbacks into healthy perspective?

Cultivate a sense of duty and frugal mind

I believe part of his success can be found in his faith. All those hours in church as a child shaped more than just his eye for style. They shaped a belief system that included duty to a higher calling. Fashion’s higher calling was to better the lives of everyday people, to give them “the armor to survive the reality of everyday life.”

Another part of his success came from his non-materialism. By not striving for a sumptuous lifestyle, he remained free to create authentic fashions and stories. If he didn’t get paid, that was the kind of setback that left his unique vision intact.

What an irony that this faith-based non-materialist succeeded outlandishly in a field that is an exemplar of materialism. And here’s the thing, if Bill Cunningham can do it, so can we.

Not without a struggle, however. Everywhere we turn, there is a new anxiety that can be remedied by spending money. A new sense of loss that must be eliminated for the sake of a joy that cannot be sustained. The effect is corrosive.

Anxiety begets anxiety which begets suspicion and alienation. The more energy we spend on spending, the less we have to spend on our own lives, the lives of our families, the lives of our communities. The greater the alienation, the less engaged we are in the duties of citizens, in finding solutions to common problems.

Each of us can work to break the cycle of anxiety -- to tilt the scales in favor of joy. I try to do my part by setting aside time each day for activities that benefit others. Maybe it’s editing an essay about Romeo and Juliet for a grandchild. Maybe it’s going door-to-door in the neighborhood to build support for a safer street. Maybe it’s helping other volunteers build a woodworking shop to reduce isolation among senior citizens.

You will do your part, too, in a way that works for you.

Perhaps, like Bill Cunningham, you will share scenes of joy that remind us of our shared (if fragile) bond of humanity.