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My size too small Gucci interview shoes were similar in spirit to this pair, but with a closed back and beige, more of a narrow loafer in the front. I loved them so and looked at them longingly many times, though likely never did actually wear them again.

Having attended a small, all-girls mostly boarding school, perhaps it's not surprising I made a decision about where to go to college based on how cute the guys on the ski team were. A foreshadowing of a prim teenager metamorphosing into a hippy party girl, using college as the Witness Protection Program. The smorgasbord of unbridled fun and freedom led to excess, which in turn led to Babson gently suggesting I take a year off to think about my future. I knew I'd never go back.

High School yearbook picture. Turtleneck, shirt and sweater was the rage. No jeans or t-shirts allowed

Returning to the NY suburbs where I had grown up never entered my mind, and I was to be on my own financially. So I headed with great enthusiasm to Filene's Basement where I put together a smashing interview outfit that consisted of an inappropriately short, off-white wide-wail corduroy skirt (A size too big. My mother was still buying me clothes I would "grow into"), a grey wool turtleneck, that bad orangey flesh color of L'Eggs panty hose we all wore, and beige Gucci almost-stilettos (a size too small but I couldn't resist those bridle bits). Although I had studied the map about where my first interview would take place, I didn't know Boston and ended up walking up and down and around Beacon Hill until my new shoes were covering nothing more than bloody stumps.

Somehow I got the job and became a secretary in a tax office at a wealth management company. My job was to type in numbers on tax forms, organize files and maintain the copy machine. If you know me well, you may be wondering how that worked out. I had a rusty ashtray on my desk and often craved putting my head down on my typewriter for a wee nap after a somewhat liquid lunch. Living in Needham and working downtown with no car, I travelled an hour each way on the commuter bus. I was going to say that my time on the bus gave me a lot of time to think, and it did, but whenever I rewind to those days, what comes to mind is my falling asleep and waking myself up with a loud snort, only to perceive everyone staring at me, trying to withhold laughter.

Express bus way back then

What I saw on that bus were women a little older than me with real work outfits and brief cases, which no doubt meant they had legitimate, mentally challenging jobs that would lead somewhere. I knew that mine was serving no purpose other than supporting me and that I was stuck, feeling overwhelmed and frozen.

So, I've always felt a strong connection to young women (because there is a gender disparity) in their early twenties encountering a cereal aisle with too many choices and the impossibility of reading all the ingredients and checking all the prices. The expectation hangs heavy that they will dive brilliantly into a new and complex world, reassuring their parents that that second mortgage to cover college tuition was a good idea. If they score a job, shortly after drinking Fireballs at college graduation they're expected to know how to address a board member, speak up appropriately in a meeting and understand all the unspoken rules of a their new place of work.

It's a hard reality that clashes with the long-held dreams that have carried them to where they are. At the Symphony, I met New England Conservatory grads who had spent their lives dedicated to an instrument, only to find out they were never going to make that top10 orchestra. At the Gardner it was Art History majors who found out that it takes 20 years and being published many times to become a curator. It's a lot for a 22-year old to take in.

So when I began to work with an organization in which I was one of only a few people over 30, I found my HR visitor chair often filled by committed and competent youg women trying to figure out how to negotiate their jobs at an organization they believed in, led by a driven, on-the-spectrum Executive Director whose managerial style skewed towards intimidation and shame. I did what I could but knew I was oil to his water. After leaving, I stayed in touch with quite a few people, two of whom have become good friends.

One was the joy in the room. Always a smile, laughter, warmth, she knew the right thing to say to calm someone down. Everyone loved her, smart as all get out (What does that even mean?) at a wide variety of things; equally competent with a complex spreadsheet as with an awkward person-to-person negotiation. With a curiosity about life, she brought enthusiam to whatever was happening, every time. But maybe she wasn't appreciated by her boss. And maybe she had been stuck in the same job for too long. And maybe she was a little unsure of where she was going.

The other woman was driven, so driven. She was continually given more responsibility, rose to every challenge and accomplished, accomplished, accomplished. She was the rising star, loved by the tyrant, meeting all his deadlines, super organized, comfortable bringing up unaddressed issues. And always with a plan for the next week, next month, next career. She was busy, she was wired. But her jaw hurt, she didn't sleep well, she never had fun. She got upset a lot.

While they were both exceedingly different, and at the time, not friends, they shared a sense of uncertainty about which direction to go in that I identified with from a long time ago. When COVID hit, they were in their mid-twenties and while we no longer worked together, the three of us began meeting outside in my back yard to talk about various life-related things. We developed a pod, a cone of silence between the three of us that became an unjudgemental place that allowed us to talk about dreams, fears, frustrations. We read books, held each other accountable, reported back, gossiped, laughed and cried.. Through it all, one moved to another state and negotiated a remote job, achieved significant life goals that had previously been out of her grasp, started painting again, took up soccer again, learned to be a better advocate for herself. The other met and then let go of a boyfriend, reconciled with her mother, put up boundaries with her father, got a new job without a tyrant, got a therapist, met her life love, took up hobbies. And I got the courage to take the next step and become single again.

I get so angry when I hear my generation complain about millenials or Gen Zers being lazy, uncommitted, sloppy, selfish, whatever the other negative traits that are thrown about. That is not my experience at all. We are a funny threesome, unlikely as you can imagine, but I'm incredibly grateful to them both for sharing their challenges and showing me how to bravely face life head on and deal with it, how to make hard but right choices. At our dinner last week, I was shocked to realize that time had marched on and they're no longer post-collegiates, but moving into the next phase of life, with friends getting married, moving to the burbs, having kids. It's my hope that I can continue to learn from these women and be inspired by them as they continue their colorful life journeys.


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