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The Tender Pursuit of Reinvention: And Other Tales From Choosing a New Career

Updated: 19 hours ago

I had the funniest conversation with my brother a few weeks ago. He was retelling his experience of a job interview process with a company interested in hiring him. It was hilarious because of what they were asking him to do: hours of online tests that involved hypothetical problems that needed solutions, long waiting periods of not hearing from anyone, and then an awkward remote interview that was surely botched after a moment of frustration he had with the interviewer.

Spoiler alert: He was offered the job, but he declined a few days later.

As he was telling me this story from his home in South Carolina, I kept interrupting not only to re-up my laughing fit but to say things like: Do they know who you are? His resume reflects decades of international business in a profession that defines the world of high-stakes deals. He is overqualified for this new job by miles, and yet the whole experience felt degrading and disorienting for someone who really should have been the one doing the interview.

I related on so many levels, and I laughed until I cried because this illustrated perfectly the tender pursuit of reinventing yourself at a certain age and level of experience. After a substantial amount of equity invested into a career, a network, a name, a title - one day you get the notion that maybe there’s something else you want to do with the good years you’ve got left. Perhaps other people you want to collaborate with. Maybe learn something new, test new limits, and find new boundaries. But when we do pivot, what gets left behind might be the very pillars on which we are built. It’s a humbling thing to let go and start again.

Much like my brother, starting again is exactly what I did last year. The decision came when I began defining what I was no longer willing to do in my career. It turns out the list was long and revealing. I took it as a sign of my evolving age and also evidence of what I already knew but ignored for the sake of reliability - which is understandable when you have a mortgage and children still at home.

A less risky revelation happened to me when I turned 40. I decided one day that I didn’t wear silver jewelry any longer. I can’t explain where it came from or why the sudden shift, but I realized it while staring at my collection of earrings, bracelets, and white-gold wedding rings one morning. I wear gold now, I said out loud, staring down at them. And they stared back at me collectively nonplused and a little pissed.

A decade later, on the doorstep of 50, something similar happened with my career. I had stayed too long doing what didn’t work anymore and like my jewelry, I was confused and more than a little pissed that I couldn’t just make it work. Get over it, it’s fine. Wear silver, it’s fine. Stay, it’s fine. They need you, it’s fine. You’re good at it, it’s fine.

It wasn't fine. I needed a change and quick. I was enamored (and terrified) at the idea of once again finding new facets of myself at this pivotal midlife time. A few months later I gave my notice, and a few months after that I was free to set out on a soul journey to discover what I wanted to do with my future.

It was one of the most terrifying times of my life.

The question that haunted me in the middle of the night was, WHO DO YOU THINK YOU ARE? It was a pretty ballsy move, and I had some serious hubris doing it that way, especially when the answer came back with a resounding I DON’T KNOW! I silently shouted that answer back out into the night more times than I can count as I swan-dived into the abyss of the unknown. But I really wanted to find out, and thus began this dark night of the soul where I was determined to answer the question.

During the fall months after I left my career, you could find me brazenly launching a podcast with absolutely no frame of reference for doing so. It felt amazing, and like coming home. Something along the lines of what I wanted to do forevermore if I could just figure out how to get paid.

Then the money I saved for this accidental sabbatical started to run out, so I spent January and most of February setting up a LinkedIn profile and trying to wrestle a resume into place. It felt miserable. The job openings for anything remotely close to a revised career in freelance writing or marketing left me feeling panicked and unqualified. The job descriptions were lengthy and unrealistic for even two people and paid half of what I thought I was worth

I spent most of those winter months breaking out in cold sweats, feeling lost and untethered. I began to wonder what all of my career efforts were for - what good did it do me now? If I could manage to qualify myself within the confines of a two-page resume, could I even get a face-to-face conversation with anyone? The market is competitive, and I realized quickly that there are a hell of a lot more people hungrier and more energetic than me.

So, in between fits of panic, I just kept asking myself WHO DO YOU THINK YOU ARE? The question started to feel less aggressive and judgmental and more of an invitation. I also did the hefty task of separating Who Am I from What Do I Want to Do? Not easy, since we are all served a small selection of boxes to fit in and then given a narrow field of careers from which to choose.

I started by naming who I wasn’t. It is a painful and disorienting process that feels a little like killing yourself softly. Which is kinda accurate. But when I had named who I wasn’t, I could then understand who I already was. Not who I wanted to become, but who I have been all along. I had lost sight of my true nature, too busy trying to belong, look good, be successful, and somehow outrun whatever it is I’m really here to do. I was miserable, but it made dinner party conversation easier and that was good enough for me, until it wasn’t.

What I’ve come to land on during this whole thing, now more than a year later, is that what I’m really here to do is hard to pin down. It doesn’t come with a title, or most of the time even a paycheck. It doesn’t even have a linear path. It looks something like an ever-present surrender to what is true for me, and not anyone else. It’s to find my own north star and hold on to it as though my life depends on it because it does. And when I started to claim this, here’s what I learned:

Who I am shows up, but doesn’t hustle.

Who I am no longer pleases others first, but honors her own needs.

Who I am sits quietly to listen, and doesn’t panic.

Who I am is someone who speaks her truth, even when it challenges others.

Who I am embraces her special gifts, and now uses them fearlessly and ruthlessly every single day she is alive.

Without the cloud of things that don’t fit - attitudes, personas, fronts - it makes decisions and preferences obvious and easy. I now know right away what feels right, and what’s in alignment with my true nature. And when something feels off? I recognize that right away, too. How’s that for groundbreaking, loving, counter-culture, and brave? This is the real me, no matter what I decide to do with it to make money.

Pretty big stuff for someone who has spent most of her life as a people pleaser and conformer. Someone who has felt her special gifts and ignored them to make others understand her better. Someone who never felt comfortable in her own skin because she was always trying to wear the skin she thought others wanted her to wear.

But I’m convinced now that when we do it like this – fearless self-knowing first - then there is no waiting around for the future to deliver our deepest desires. They are already ours to claim right now at this moment. No online test questions or awkward interviews required!

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