My husband and I walk to the local Farmer’s Market every Sunday morning. My role in this ritual is to stand around, drink coffee, and display the pug while my husband buys produce that he will eventually prepare. This gives me time to watch people. 

Although there are shoppers of all ages in the early morning, a significant number are women who appear to be in their seventies or eighties. Some of these elderly ladies look as if they woke up one sunny day in 1973, dressed in their Sunday best, fell into a worm hole, and ended up on a street in 2006 by accident. Patent leather shoes with chunky heels; textured, patterned polyester cinched with elastic; hose as thick as a second skin. They make me feel nostalgic, images of my grandma out on the town. But there are just as many of these older women who look almost hip, age-appropriate yet updated. As casually dressed as their younger counterparts, they sport denim, jersey cotton, and fun sneakers. What is the difference? Why is a 30-year-old outfit just fine for one woman while the other appreciates the latest color palette from The Gap?

There are a million real-life reasons why anyone wears anything—a love of fashion, limited or excess funds, whatever happened to be clean or dirty that morning, perhaps sentimental attachment. These older women are no different from the rest of us and our auto-pilot routines. I realize what piques my interest has less to do with logic and everything to do with what’s on my mind that week.

As I noted each woman who wandered by with her carrots and berries, I projected as to why some people choose to change small aspects of themselves, in this case shifting their styles to fit current trends, and others choose not to, feeling so comfortable that there is no need to buy new clothes if old ones still do the job. What we wear is just a minor manifestation of how our personalities and behavioral quirks figure and reconfigure over the years. Sometimes the picture changes whether we like it or not. As carbon-based organisms we physically deteriorate—hair grays, skin sags, suddenly words close and far are hard to read. More fascinating than inevitable changes are the conscious adaptations. We choose to shuffle from time to time, we choose to reinvent what doesn’t fit our current scene, and even more compelling than what we give up is what we cling to, no matter how great the pressure to let go. 

Years ago when I was a fledgling middle manager, a store manager called me in her office for a “developmental discussion,” code word in our work for “you are in big trouble.” It seemed that though my performance was generally good, she felt that I used too many big words and sounded condescending. She recommended that I overhaul my communication style if I wanted to be an effective leader. I listened to what she said and then responded, not with my usual hyper-intellectual insecurity, but with surprising instinct. I said that if my tone of voice made people feel disrespected, then I would change immediately. This was not my intent and I would listen vigilantly to catch myself. I also understood the need to be clear. But I would not simplify my vocabulary or “dumb-down” the way I talked. This request veered too close to my core, and I could not believe this was the real problem. 

Fast forward, same company, where today I am in a position that depends on a facility with language–what was once considered too complicated is now considered essential. Yet this same skill set is linked to a careful modulation and warmth of delivery. I am grateful that this manager gave me a chance to fix an immature tendency. A decision to change one behavior, a decision to preserve another—what are we willing to do for a job, for a reputation, for money, for family, for art, for belief, for love? When is the change worth it and when does the loss make us bitter and resentful? My relationship with the staff in my long-ago store mattered to me and my love for words trumped all.

Sometimes personal transformation looms monumental, sometimes we pray it will be easier than it looks, but really, it is just so daily. It happens every moment: do I speak up or sit down, do I eat the cake or go for a walk, do I wear the cargo pants or the skirt? Each instant is insignificant, yet when layered, they stack up to a life. At least theoretically, these accumulated decisions offer us the possibility of evolution, molding a self as acclimated to people and environments as Darwin’s finches. Occasionally the pendulum of our decisions blur, we are defiant like Popeye, “I yam who I yam,” love me as is or leave me, and we become weighed down with what we refuse to see like lumbering, eccentric dinosaurs.  Or we aim to please the masses and change to the extent that we are transparent and flimsy, absorbed by the person who stands next to us. Instead of finches, dodos.

At the crux of each tiny question is recognizing what we truly value in ourselves and our role in the universe. According to OB expert Margaret Wheatley, people and organizations often find themselves in a similar situation to pioneers crossing the prairie with wagons and handcarts. At the beginning of the journey they packed as many possessions from their home as they could possibly carry, dreaming that they would recreate their exact Eastern farmhouse in the Western frontier. All rumbled along fine across the flatlands and then, rising straight up from the grass, they faced the Rocky Mountains. They could not push all that they had brought over the ridges and had to lighten the load by necessity. They had to decide what would be most essential in their new life and what they would have to toss away. Their choices were not always obvious. For some families the English china made the cut and the ticking cloth didn’t. The Bible was wedged between salt and sugar; the extra pair of shoes dropped by the wayside with the washtub.   

I think about my handcart and the debris that lays in my wake. I fear that I have dropped more acquaintances than bad habits. I have less patience and more chocolate. I definitely lost the bad long dresses, somewhere I picked up a tinderbox temper, and we are still hauling along our marriage in spite of some very steep inclines. Over all, as I get older, the load feels lighter; I tend to like more of what’s left and I am getting bit by bit smarter at knowing what is right to do in those blinks of dilemma that push me forward.

At eighty which old lady will I be: the one wearing the same pair of jeans I am wearing right now or the one wearing the Tyvek and spun aluminum space suit? What I hope survives in the next forty years of choices—some considered, some risky, some wrong—will be a mix of qualities and passions that are honed, free of junk and clearly useful to myself and the people I encounter. Ultimately what I wear won’t be as important as whether or not I stoop to pet the pug or goo goo at the baby or find the freshest peaches, celebrating each movement that adds to what may be, by then, a most distinct collection of choices.