In Spinster, Kate Bolick references a 1950 New York Times article that describes “coolness” as “that perfect mastery (or numbness) of self that enables the ‘hipster,’ the cool cat, to listen to the loudest and most throbbing jazz without displaying the least sign of emotion.”

I was so struck by this definition of coolness in light of recent conversations and realizations that I had to put the book down, record the quote, and reflect before reading on. Bolick’s point was that no one would have mistook her for cool–and it was because she got far too excited about things, invested in things, for that mistake to happen.

Suddenly, something I’d been wrestling with in therapy and in coaching became perfectly clear to me. Not only am I not cool, but I never will be, and nor do I want to be.

Holy shit, hallelujah.

In my second session of therapy, before we really started digging into stuff, I told her I wasn’t sure I knew how to “do” interpersonal relationships. I’ve never been good at maintaining friendships or relationships; I often feel very isolated and unfulfilled and I think it’s because my relationships aren’t as intimate as I want them to be. Later, we would find out I had bad selection criteria–or nonexistent selection criteria–or at least selection criteria that was far removed from the person I am actually am and closer to the person I kept trying to be for most of my life.

But before this, in the last training weekend of my coaching program, we played this game for about fifteen minutes every day. I can’t give it away because we are sworn to secrecy, but in the game, I had a profound moment of basically realizing that I disengaged from my own life sometime around 5th grade when I started getting bullied. And I have been disengaged ever since.

Being disengaged–not getting emotionally involved or invested–meant everything would hurt less because I would hardly feel anything at all. Numbness and apathy were infinitely more preferable than rejection and failure, especially when it came to judgment by my peers. My poor, sweet little 5th grade brain didn’t know any better–and no one ever told me, or at least I didn’t get the message–that it was totally okay to be my own nerdy self with my own nerdy passions. To me, social acceptance–coolness–was the ultimate goal. It was instilled in me as a major value.

By disengaging, I avoided hurt, but I also distanced myself from myself–from what I really wanted out of life and cared about. If the things I wanted or cared about didn’t seem to be cool by the standards of the dominant social group wherever I was, I kept them locked down. I stopped expressing opinions. And, most crucially, some time after one of my most hurtful relationships in college, I started seeking out people who seemed as emotionally disengaged as I dreamed of being.

It was my unconscious dream to live an emotionless life.

Not having emotions meant never being hurt and humiliated and separated from the pack, being seen as weak or a failure or unfit.

And therein was the great disconnect I began to feel when I started the healing process and learned how to feel again, both the ugly and the delightful.

At my core, I don’t have the perfect mastery or numbness of self required to go through life without betraying emotion. I care about a lot of things, things that some find totally weird. I feel a lot of emotions, and I want to talk about them. My therapist asked me about my most fulfilling relationships, and I recognized that they were the ones in which we could bare our souls to each other, unfettered by the shackles of coolness. We would talk expansively, limitlessly, asking questions and giving space and wrestling with problems about life’s deeper meaning together. Never have I felt closer to something resembling “myself” than in those instances. Never have I felt truer intimacy with another human being.

So I take a risk in expressing my newfound desire because I haven’t really drawn any conclusions about it. It’s still in progress. But I’m through trying to be cool. I’m not and I don’t want to be. Trying has barred me from deep, intimate connection with others and with myself.

If you, like me, have lived a life in which you’re constantly bombarded with the directive to BE YOURSELF but you’ve received very little guidance on what that means or how to do it, I urge you to think of what choices you’ve made that are truly yours vs. those that are closer to what other people want. It’s certainly been easier for me to imagine choices I made for other people as my own choices. The tradeoff of making your own is you might get hurt but at least you’ll be fulfilled and connected.

The way I’ve been able to relax in the short few days since making these connections has been a relief. I’m also excited to read Brené Brown’s new book, Braving the Wilderness, because it’s all about this stuff: finding belonging in yourself before worrying about being cool, and of course, letting yourself feel all the emotions instead of walking through life pretending you’re immune.