Maybe We’re Just The Restless Generation

A few years ago, I was interning at the ACLU on Drumm St. in San Francisco. I believed then, that I was going to become a lawyer — tentatively beginning in corporate, but assuredly ending as a nonprofit lawyer that specialized in health policy and redressing the failures of our healthcare system.

Last weekend, over a glass of pinot noir and lamb meatballs, someone who I met then and who I miraculously still know now, reminded me: “Remember when I first met you? You were so sure — I was sure — you’d be a lawyer by now.”

Too many years after all of those tentative dreams, we’ve somehow become less sure, of ourselves, of each other. Much has already been written all over the internet, echoed over basil gimlets and mid-day lattes, on the subject of our generation and our particular and peculiar ways — cohabiting earlier and marrying later; emulating the drifters and the hippies who came before us; our open-to-interpretation, and open-to-experimentation versions of ourselves; our wanderlust and our inability to commit to anything; our interminable search for ourselves and our seemingly endless quarter-life crises.

While looking out at the Golden Gate Bridge from our hike into the Marin Headlands, a friend asked, “Do you feel more or less restless now than when you first graduated?”

It was more, for both of us.

We came into the real world — I’m beginning to hate that phrase — with a hazy understanding of what comes next. We saw the footprints of our parents and their parents, compacted in the soil of the trail they blazed for us. And somewhere along the way, our generation had the nerve to step off-road, outside of the boundaries of the beaten path. And now, where are we? We tried, we tried to follow the path forward, to that white picket fence and three adorable children. But we couldn’t help looking up. And what we saw in the distance — it moved us. It stirred something within ourselves that we thought we had left behind with our beanie babies and our make-believe.

Our day jobs may afford us weekend trips to Vegas day clubs, but, at the end of each day, there is an unsettling sense of being unfulfilled, mixed with longing and garnished with boredom.

You work so hard to get to where you are, only to find that it’s not where you want to be. But how do you leave a good thing? Even if it’s not a good thing for you? Or more accurately, not right for you? We stay, because what moves us, what stirs something unseen within us, also frightens us. It scares the shit out of us.

It’s becoming a tale as old as time. She’s in private equity but she wants to start her own business. He’s a software engineer at a rocket ship of a startup and he’d rather be in the woods up north composing music. He’s in design but when asked if he could do anything? Movie director, restauranteur, maybe a writer. She’s a consultant who’s waiting for her holiday bonus to quit and pursue singing.

And in the meantime, are we all just settling?

Our predecessors climbed Maslow’s Hierarchy of Needs and now, we’re standing at the top, twiddling our fingers and wondering uneasily what this “self-actualization” is exactly. There’s a search for meaning, for purpose, that’s emerged. And with that, there’s a need for a new paradigm, a pyramid beyond self-actualization.

Or maybe it’s just time to jump off. Start at the bottom again. And do the climb for yourself. When we give up everything we have and everything we know to eat-pray-love our way across the world or leave our six-figure jobs to build a company from the ground up, when our expensive restaurants are replaced by Clif bars, that’s exactly what we’re doing. We’re making the conscious choice to work for every future moment, even if we don’t have to.

Maybe life is about doing things that scare the shit out of you.