Always hit on 15

The pain in the ass of being authentic.

Not that I’ve been recently, but when I go to Vegas, I love to play black jack. Like, I can sit at a table for an entire night, nursing some free bottom-shelf drink, throwing down chips, and telling my life story to people I’ve only just met. I live for a $5 table where I can make $40 stretch for hours.

I’ve always been drawn to black jack because it’s so inherently social, but not in a rambunctious way, like craps, or heart-palpitating like roulette. A good table always has the feel of a local bar, a real schmoozy spot to make the best friends of your life for approximately three hours.

To me, black jack is a communal experience because dealers, and other players, are allowed to help you decide what moves to make. They can’t tell you what to do, but everyone is allowed to remind you of the rules and best practices. For instance, I remember one of the first things I was taught by a stranger at a table was to be consistent whenever I was dealt a 15. If you’re unfamiliar, in black jack, 15 is a a bit of a soft hand; you could play it two ways––stay to be conservative, or take a risk and hit for another card, in the hopes that you’ll make it closer to 21. The advice was to always make the same choice, because the consistency increases the odds that you’ll win over time.

I decided early on to always take the hit, and have never wavered since.

The intimacy that comes with showing all your cards is a unique characteristic in a card game. There’s vulnerability when there are no secrets and individual wins never result in a loss for someone else. There’s no competition in black jack! It’s the players versus the dealer, and they have no real skin in the game. Everyone wins together, and everyone loses together.

I’m an excellent black jack player, and I believe it’s because I’m someone who always shows their cards. I’m totally me no matter the context.

I would say this personality trait is to my benefit about 85 percent of the time but, man, that 15 percent when it’s not reciprocated really stings. For the most part, being open, honest, and transparent creates a sense of authenticity that other people can trust. This way of interacting with others often creates a safe space for mirroring my openness.

You show me your insides, and I’ll show you mine for collateral. That’s how I do relationship building. Whether it be with friendships, romantic partnerships, or work relationships, this how I operate.

Again, this works out in my favor most of the time. However, sometimes, it crashes and burns pretty badly.

In a romantic partnership, it’s always been sad and perhaps a little embarrassing. But, in the end, I’m never mad at myself for opening up to love. Friendships that go sour feel similarly. It hurts when vulnerability isn’t reciprocated, but again, I don’t blame myself for trying to make a connection. I accept that I can’t force anyone to love or like me.

At work, it’s a different story. Instead of feeling sad, I get M-A-D. I’m hurt in a way that feels like it IS my fault. In a professional setting, an unwillingness to match vulnerability feels like a big fat fuck you. And, when the other person not only doesn’t return the kindness, but takes advantage of your generosity of self to make you look bad, it can seem like betrayal.

This has happened to me a few times, and I feel stupid every time. Did I not learn anything? Why do I have be so damn… ME all the time?

Years ago, I was given a new manager. She was hired from outside the organization by my boss at the time, whom I trusted very much. He had too many people reporting to him, and I was chosen to be offloaded onto someone else. But, if he thought this person was the right fit to manage me and my work, then I thought she must be great. On her first day, we grabbed lunch from a food truck. I excitedly, and generously gave her the lay of the land, the ins and outs, and tips on how to navigate departments and leaders––the good, the bad, and the workplace drama. I shared what felt difficult for me, what I wanted to do, and where I felt I could be of service.

I showed every last one of my cards and, having been at the company for a few years, I had a pretty good hand. And, I just gave it all away.

She offered me nothing in return. Just a polite head nod. In fact, she ultimately used everything I freely gifted against me. This person gaslit me, talked down, diluted my work, cut down ideas, purposely put up roadblocks to opportunities, and consistently found ways to make me feel small and stupid.

I swore I would never make that mistake again. But, of course, I have. When this happened, I was younger and at an earlier stage of my career, so it affected me more deeply. But, being in a more mature and seasoned place doesn’t shield me from being hurt and doubting my ability.

Look, I’m not above constructive feedback, continually working on myself, and being more discerning about how I present different parts of myself in different environments. But, not at the expense of changing who I am. I don’t want to be someone who squashes their authenticity. I don’t want to be someone who doesn’t put implicit trust into the people around me.

I don’t want to put on a poker face, when I’m really a black jack player. It’s not about winning or losing for me; it’s about learning, getting better, and having a positive experience.

But, the workplace is generally an inherently competitive environment, which is why I’ve struggled in past positions. It’s why freelancing has always been attractive to me, even though I crave a team. No matter what kind of kumbaya culture you have, everyone is there at will, and can leave whenever they want for something better. It’s easy to forget that nobody owes you a thing. People don’t have to like you, and they certainly aren’t obligated to be nice and help remind you the rules of the game. But, it would be nice if they did, right? Maybe I’m too pollyanna about it all.

I’d like to say I’m trying to work on being more judicious about who gets every part of me, but I don’t think I am. That’s ok. While, I am always looking to work on becoming my best version in any relationship and context, I’m going to double down on being my freaky self.

At the end of the day, I’d rather lose all my chips than any part of myself.