How I Hacked My Vulnerability

Writing my feelings on the Internet helped me grow in real life.

In the hallway of my condo, there’s a message on my whiteboard calendar. It reads, simply, “Be kind to yourself.” It was handwritten about a year ago by a woman I was casually seeing at the time. We’d go on very unromantic dates that ended the next morning, and talk for hours on the phone at night, occasionally spending the back half of those hours describing in alluring detail what we’d do to each other if we were in the same room instead of the same zip code. The beer-swilling, dog-loving blonde from West Virginia was comical and complex, radiant and dark, occasionally all at once. She was a deeply empathetic, omnisexual crusader for social justice who loved long runs in the rain and was a sucker for a full-bodied stout or porter.

She was also a social worker, but not my social worker. With a keen eye for humanity’s well-being, a hyper-colour personality, and a Cabernet-dry wit, her obsession for digging deeper into whatever sparked her curiosity meant she’d occasionally probe deep into my feelings. She’d ask me things like why I was being so self-loathing before I’d even said a word about myself. She’d often tell me I’d been “misdiagnosed” as chronically anxious and depressed, and that I was more of a Bipolar II with rapid cycling. I never disagreed with her. She bought me my first six-pack of Topo Chico after I decided I’d stop drinking myself to death. She told me I was “working through something.” When I asked if it was my breakup, she was quick to note, “no, this is deeper than that. Something more visceral.” I’d ask her what it was, and she’d say, “only you will know.”

After I stopped drinking, she stopped seeing me, perhaps because she had a girlfriend to get back to, but more likely because I was a five-star grouch while drying out. Indeed, I was. It’d be a solid three weeks before I rediscovered even a single degree of bliss. The intervening days and nights were largely spent balled up on my couch, shaking, sweating and silent. She left without saying a word; I went a long time letting her musings marinate in this broken brain of mine. I never erased her message to me. It felt like she’d written it for a reason.

I’ve centred much of my writing, since we launched the pirate ship 15 months ago, squarely on “how I feel.” It started from a place of desperation. I had some feelings, I was terrible at expressing them to friends, family and therapists, and so I thought by giving myself the freedom to unspool them at a leisurely pace — and with the assistance of editing — I could finally articulate them in a way people could relate to … and in a way people would want to hear. That clause after the ellipses is important.

I did not grow up in a household where sharing your feelings — the negative ones in particular like sadness, anger, frustration — was something you could do openly, safely, without fear of judgment. I never left a heart-to-heart feeling emotionally satisfied. Everyone in the family would either reciprocate by dumping their seemingly darker feelings and problems on me, try in vain to treat the symptoms and not the cause, or tell me I was wrong for feeling the way I did. You would think I learned this behavioural pattern from my dad — as most men’s toxic inabilities to share, name and later even feel seem to stem from. But, no, I could talk to my dad about anything. I just didn’t, you know, live with him, and there were darker personalities and deeper pathologies within much closer proximity — in my own home. It took me until I was 31, and regularly seeing a therapist, that I realized that these patterns of behavior exhibited by my immediate family were pathological: that it’s not normal to cry at the drop of a hat, or reciprocate someone’s opening their soul to you by unloading your brand of upset onto them in an effort to “relate.”

After hitting age 28 or so, I often felt ashamed to even approach anyone — including my dad — with feelings or problems, not because I didn’t feel safe or comfortable, but because, well … I still had so many of them. My dad was a homeowner, married, had a full-time job, and a child (me!) by that age. Clearly, I just needed to sink or swim. Surely, he’d sleep better knowing his son was just fine.

My flaming hot take was this: People do not want to listen to your problems, unless you are telling a story about how you solved them. “You should see a therapist,” they’ll tell you otherwise. “That’s what they’re there for.”

Around the time my parents’ legal union passed the “sell by” date, I started developing a new behavioural tic. I started becoming very emotionally vulnerable with the women friends in my life. We’d talk on the phone for hours — Kerri from the other side of the tracks, Megan from the other other side of the tracks — women who lived far enough away that I wouldn’t be forced to see them in school, but close enough that, if the mood struck us, we could meet at the Dunkin Donuts after 10 p.m. in a town where that was the only joint open that catered to minors.

Every bit of that is instructive when it comes to understanding how I communicate now, some 20 years later. I will be extraordinarily open and vulnerable with people who live far away. Why? There’s no real stakes in play. Like, what’s the worst that could happen? You’ll never see them again? Ha! I’ve been doing it ever since. My first girlfriend was a two-hour drive away. My second a four-hour drive. My fourth was 90-minute drive. My best friends live in New York. Half my Facebook friends don’t live in Texas. 5–10% (estimated) don’t live in the US.

I talk to a woman in New York almost every day, usually for over an hour each time. We laugh. We cry. We think. We feel. We are something approximating boyfriend/girlfriend, brother/sister, BFF/BFF all at the same time. It’s the perfect relationship: low-risk, high-reward, and it sounds like we’re simply communicating our inner monologues to each other, and commenting on them.

My Facebook oversharing is already legendary. I can, through the magic of writing instead of talking, articulate my feelings in ways I could never via just talking to people one-on-one. But clarity is only half the reason for it.

The other reason I’m so transparent on the Internet? It subsidises the risk. My feelings are broadcast instead of discussed, and then they’re divided amongst the audience. To give a more real-life example: This is the same reason I won’t sweat singing for hundreds of people, but if you ask me to play specifically you a song, I’ll clam up. My “vulnerability” is easy when I only have to worry about 10 out of 600 people on the Internet judging me, instead of 1 out of 1, in the same room. The stakes are more distant, more diffuse. It’s in this very 21st Century way that I’m trying to recreate the emotional intimacy I never received as a child, without actually having to risk rejection.

I am often told on here I’m courageous for my “vulnerability.” I want to talk about that for a second. I’ve admitted to things on this blog — using my real name and everything — I wouldn’t feel comfortable telling *anyone.* Substance abuse. Infidelity. Promiscuity. Suicidal thoughts. And I do this to thousands of people per day.

Yet, people relate. Particularly to the dark stuff. I imagine, in my head anyway, that this is part of why people seem to like reading me. The honesty and the universality of what I print. I get a lot of “get out of my head!”-type comments. But readers are even going one step further.

I’ve run an experiment all year, with my phone number as both my pinned tweet and my Facebook cover photo. Half of it is an examination of white male privilege — I’ve gotten no death or rape threats, and only one request to invest in someone’s startup, and I’ll be writing about this experience toward the end of 2018 — but also to see how safe people feel anonymously disclosing their darkness to me. (Answer: very.) I can’t tell you how many people I’ve talked through things like substance abuse, depression, suicidal ideation, infidelity, terminal illness and so on. And while I can’t say for certain if I’ve helped, I’ve noticed an intriguing side-effect: I think those exchanges have helped me grow as a person.

Talking one-on-one with readers, when coupled with my daily writing practice, has helped me name, articulate and really *feel* my feelings in real life, and really show up better for people. Even, finally, with more immediate people who are closer to me. It’s not quite emotional mastery, yet, but it’s a start!

I still overshare. I still write about dark stuff. Some people, particularly those close to me, ask things like “aren’t you worried about your career?” The answer is: no. No, I’m not. This is my career. I get paid to make people feel things with words. My readers, my coworkers and my connections have become far more likely to lift me up, now that I’m a visibly three-dimensional person, rather than if I was a flat approximation of a human — the way so many of us seem to be. People are craving a space where it’s okay for them to talk about their feelings, honestly, and occasionally with gallows humour. I’m proud to help create that space, and I think that’s the best thing I do with the writings you read here. (That and, you know, my right-hooks at the Clickbait Industrial Complex.) I think this world would be better served if more people felt safer being three-dimensional — if people felt comfortable feeling stuff and sharing it.

In that regard, my decision to peel the curtain all the way back was, and continues to be, one of the least risky moves I’ve ever made — it’s helped fill a gap that existed, both in my life and in society at large. I feel safe expressing my feelings, and it helps other people now do the same. Not in an empty “reach out if you ever need anything” or “here’s the number for the suicide hotline” way: in a real “here’s an elephant in the room, we both know it’s here, let’s break out the peanuts” way.

Why do I tell you all this? Because I want you to know it’s okay to be three-dimensional. This world is dark. And getting darker. You’re going to feel some things, and many of them won’t be pleasant. The better you get at naming them, sharing them and processing them, the more you’ll grow. You’re probably feeling things right now you’d never post as a status, or disclose with a close friend, or the public at large. I get it. (Twitter, interestingly, is everyone’s id, and proof that we’re all raging trash-fires so long as we don’t have to attach our name or face to our thoughts and feelings, so it doesn’t count.)

Anyway, if you have stuff you wanna talk about but you think you’ll be judged, if you’re “working through something,” I’ve got peanuts. My phone number is literally public record. You are welcome here, you are safe, and I appreciate having you aboard this pirate ship. I’ll never erase what I’ve written — I realize I’ve been writing it for a reason. Till next time, be kind to yourselves.

This article first appeared on Medium.