Over the past several weeks I’ve been visiting a personal coach in San Francisco. I was expecting a mentor, someone who’d show me the ropes to the profession so I could see if I’m cut out for it. At the time I thought that’s what I was missing in my life: a career to work towards. However, looking at my life from the outsider perspective, there’s a lot of work that needs to be done:
Young man, single, living with his parents, and working part-time.

We started off on the “Single” part.

I protested at first, figuring that my main concern ought to be my means of employment. After all, that’s what most people would tell me. My coach had a different plan:

“Your job won’t mean a shit to you if you aren’t happy with your life. You’re just waiting for conditions in your life for it to be okay to express yourself. I’m telling you – it’s not going to happen.”

He was right and I knew it. It wasn’t just about the getting the job or the girl, though. I’ve always been a bit too reserved, too afraid to rock the boat if people found out what it is that I truly wanted. So I agreed with his idea, and we proceeded with the coaching.

We started off light, just by connecting with people in general. Once a day, I’d have to be a bit more intrusive in my interactions with people than I’d usually be. “What was the most difficult part of your day?” was the question I asked people to find out more about them. It was easy enough and got some momentum going for the assignments in the upcoming weeks.

Catching on that this wasn’t much of a challenge, my coach upped the ante a little bit: the next week I’d have to make some sort of remark to a girl I’m interested in.

The week flew by without me taking part in this assignment. I realized that if I didn’t act soon, I’d come back empty-handed. One night I set out to have at least one win, one interaction where I express my attraction to someone.

I arrived at a cafe at around 9pm. I sat down with a book and laptop, pretending to something important. Looking around I could see almost everyone was working on something, whether it was for school or their jobs. It was quiet, which in my case wasn’t really a good thing. Either way I knew I’d committed to this assignment, and had to follow through.

She was sitting at the table across from me. Headphones plugged in, studying for school and texting on her phone. Thoughts came up right away:

“You’re being creepy right now.”

“Maybe you should just call it a night.”

I decided to go through with it anyways. I decided that for the night I’d let people think what they want about me. I gathered my things, put my jacket on walked up to her table. Tapping on it to get her attention I said quietly:

“Hey before I leave I just wanted to say I… think you’re really pretty.”

Her face went from confused to disturbed as she said: “Okay…”
I nodded my head and, turning towards the door walked straight ahead, without averting my eyes to see who was looking.

Once I got out I laughed and said to myself “I don’t care.”

I had just made a bad impression on a room full of people, and I was okay with that. After all, they probably only had time for one thought about me, before they went back to work or Facebook.

I was excited to tell my coach about the experience, but I was less thrilled about my next assignment. I was to do the same thing, this time on the street. Seeing as how last time I headed straight for the door, I wasn’t allowed to move from my spot this time. I was to wait for people to come to me, as if I had some nonprofit job, asking people for donations.

Standing there on the street corner, some of the same thoughts came up for me. I was ashamed of myself: Didn’t I have anything better to do? Shouldn’t I be at work like everyone else? Probably for the first time in my life I didn’t have a solid sense of identity; I wasn’t a student, worker or homeless man. I was just some dude on the street. It took some convincing, but I came to realize that this really was a worthwhile endeavor. I wasn’t ashamed of myself because of my circumstances; I was ashamed of myself, period. Recognizing this and the fact that I had all but disowned my sexuality for the sake of being comfortable, I found this assignment to be really deserving of my attention.

And so I carried on, standing at the street corner, occasionally stopping the women that walked by to go through the clumsy little script that I was using:

“Excuse me, can I say something to you?”

As expected, most just walked on by, pretending they didn’t hear anything. Others just said no, which I was also okay with. To those that stopped I would say:

“I’m learning how to communicate more courageously, and so I’m supposed to stand here and wait for someone to walk by that I think is pretty, and then tell them so. So here it goes… I think you’re pretty.”

The intent was to be disarming, to be honest and clear that my agenda was to learn how to communicate. Overall, their reactions were somewhat positive: one wished me luck in my learning, and another asked me for directions to a clinic. It really wasn’t as big of a deal as I had made it out to be, and no one was actually offended by my comments. Little by little I expanded into this area of my life that I’ve been so uncomfortable in. It was a slow start and it felt like something I should have gone through years ago, but I was determined to go through the process and grow as a person by doing so.

That concludes part one of my chronicles in learning how to speak my truth, and communicating what it is that I really want. There’s a lot more to it and I hope you’ll stick around!

Thanks for reading,

Rolando