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Got a Girl Crush On: Cassie’s young heart bein’ free

Former GAGC contributor and now vagabond bon vivant, Cassie, recently quit her job, fled NYC, and is traveling to see what the world has to offer in the pursuit of happiness.

Follow her travels and writings here.


I quit my job last month. A lot of people were surprised. To be honest, even I was a little surprised. Since then, though, I’ve fielded a lot of emails, phone calls, coffee dates, and dinner conversations about The Big Decision. 

How does it feel? How did I make it? Was it the right one? (Great. I’ll explain in a minute. Absolutely.) 

What was interesting about those conversations, I found, was that most people we’re probing me for my permission to be unhappy with their own lives, and for a vote of confidence that they could make a change. If there’s one thing that’s surprised me these past few months, it’s how often people struggle to admit they’re unhappy with something unless that thing is objectively, undeniably terrible. Sometimes, things are perfectly fine and you still don’t want them. That’s fine. 

So why did I realize I needed to leave? Part of it was just the city. Working and living in New York was like having swallowed a persistent, unkillable bee of anxiety. Every day I woke up and made a decision to be happy, counting the ways that everything was fine and normal. Unsurprisingly, this turned out to be absolutely exhausting, and emotional incongruity duly followed. As the months turned into years, and the years kept on passing, I grew deeply uneasy, increasingly distressed, and utterly unable to self-psychologize an anecdote. What was wrong with me? 

Now, after a lot of thought, I realize that I was suffering from a kind of mimicry. Rather than thoughtfully defining what I personally wanted, I had absorbed an arbitrary value system from my surrounding environment. Based on that, I had created a set of goals that I had no real desire to accomplish, but felt crappy nevertheless for failing to achieve. I just saw other people around me defining success and happiness as a certain thing, and thought, “Oh, that must be it.”  And I had ended up working in the opposite direction of anything I had ever wanted or that made me feel good, but the further along I got on that path, the more resigned I felt to it. Like: I have to do this now, I am already halfway there. 

Fact: I didn’t like showing up to the same place, five days a week, on a heavily regimented schedule of 12-hour, 9-whenever, workdays. I wanted to work hard, and I liked working hard, but I wanted to do it on my rhythm. I wanted to look up and see stars at night. I wanted to wake up to bird calls. I wanted to spend meaningful time with a small group of people who weren’t always too busy. I wanted to be good at my job. None of these things were happening, the latter point most certainly not helped by the former. 

Fact: I am young. I was the first employee of a hugely successful start-up. I have no significant others. I have savings and no looming financial obligations. If there was ever a time to take a chance, unburdened by accountability or compromise, now was it. Having absolutely nothing to lose, in this very specific instance, placed me in the most unbelievably fortunate position. 

So I admitted I hadn’t found My Thing yet. I admitted that I might step off this cliff and never find it, but that trying was more important to me than whether or not I ultimately succeeded. From that perspective, the stakes became radically different. While fear of failure had seemed dehabilitating before, now I could try and fail and that was still perfectly fine. I also admitted I wasn’t going to settle into life in New York or at Kickstarter and finally accept it and be happy. And, most importantly, I finally forgave myself for feeling that way — because I had been beating the living shit out of myself for it before.

Somebody smart once said to me: “Don’t think about what you want to do, think about how you want to FEEL.” That comment made all the difference. Sometimes it’s hard to make a definitive decision when you’re not 100% sure of what the next step is — where do I go? what do I do? — but that shit doesn’t matter. Just aim for the feeling, keep working hard, keep your eyes open, and the rest will fall into place. It will. 

For me, placing myself in my ideal environment — even just knowing that I am working toward that end — enabled me to be my best person, specifically in terms of what I can give back to my family, my friends, and my work. And being on the move, having absolutely no stuff, and having agency in what my daily surroundings will be? That is my ideal environment.  I focus better, I work harder, I am more satisfied by my work, I make better choices, etc. So I’m doing it.

No doubt that freestyle work has its own set of challenges — a little bit of uncertainty, a whole lot of hustle — but these aren’t battles I have ever minded fighting. In the end, I really don’t think that life is about finding The Best Thing, but just about defining what battles you will be OK fighting for the rest of your life. Not in a bad way. In a great way. Fighting for what you care about is one of the best feelings in the world, to me, even when it exhausts me.

It may not last forever, but I am going to do it until it doesn’t feel right anymore. 

There are a lot of other reasons I left, of course, but these are the ones that really matter, and the ones I built my decision around, and the ones I will build (hopefully) the rest of my life from. 

That’s all, and here’s hoping.