I Wanted to Be a Cowboy for Halloween

Earlier this month, I attended the Immersive Industry Summit at Esalen organized by Alison Raby and James Hanusa of Digital Raign. It was billed as an AR/VR for Good event, and it was noted that diversity and inclusion would be on the table. Mid-summit, Alison, Melissa Sutor, and Ashara Ekundayo led an evening discussion about diversity and inclusion for the broad Esalen community.

In that discussion, Ashara presented of a checklist of privileges from Buzzfeed based on a number of factors, including socio-economics, race, age, appearance, sexual orientation, disability status, and more. Examples include “I have never been the only person of my race in a room”, “I have never been catcalled”, and “I have never had to worry about making the rent.”

Ashara encouraged us to keep score, counting one point for each privilege that we experience. As the list proceeded, I came to realize on a profound level how much privilege I experience as a hetero-normative African American male of which I am mostly oblivious. When I think of this, I feel more empathetic and compassionate. When I think of this, I feel more connected.

It was a very long list. And Ashara didn’t even read them all.

As I awoke from a nap this weekend, I realized that I needed to point out a new item for the list Ashara was reading. Probably just one of many seasonal privileges that many of us may or may not be aware of.   


I am not a huge fan of Halloween but I do recognize that it can have its moments. Without spirit and nutrition, in my mind, the tradition pales in comparison to the rich and culturally significant Dia de Los Muertos. When I was young, I loved to trick or treat, with fully realized expectations of all treats and sugar rushes, amassing huge bags of candy and consuming them over the following months.

Now, for me, the magic of Halloween is in the costumes and the opportunity to role play in public with strangers. Role playing can unleash parts of ourselves that long to be experienced.

My Halloween foray this year was Daybreaker’s Halloween Boat Cruise leaving from Pier 3 in  San Francisco on Friday morning. My friend Jonny bought me a ticket as thank you for shepherded his Jeep when he was shooting a film overseas about Syrian refugees in Europe.

He had sent me text several days beforehand, asking if I had wanted to go. My first inclination was no, given that it left the dock at 7:10a. But I sat on it, and realized that it was an opportunity to do something different and meet people I might not otherwise. Despite the gloomy skies and the rain coming down the day before, I texted Jonny Yes without even checking the forecast.

The morning came way too early but at least there was no rain. I wore an eye mask reminiscent of the Kubrick film, Eyes Wide Shut. I wore the black four button suit I was married in. I started out being a member of a secret society and  evolved into that wild side of you that is wanting to be expressed.

When I hopped into the aforementioned Jeep that morning, I saw that Jonny was a cowboy. He was wearing a rugged leather cowboy hat, boot leg jeans, a slightly ornate belt buckle, old cowboy boots, a cool western shirt, and as I noticed when stepped down from the Jeep upon arrival, a holster with two plastic guns. Obviously plastic guns.

Seeing him and his costume in full regalia, I was a bit jealous. It was stylish, cohesive, and just the right amount over the top for Halloween. It was working. At that moment, I wanted a cowboy costume. I imagined how much fun he could have with his prop guns. I imagined him pointing them at people, arresting people, shooting at cute girls’ feet to make her dance, put a hand on a holster to convey alarm, blowing gunsmoke in someone’s direction…

I like play acting especially when others are into it. I knew that those prop guns in the Cowboy context were the ticket. If only I could be a cowboy, maybe next party… no… not ever… in this country at least.

Seconds later, I told Jonny what a cool costume he had and how the guns took it to the next level. And then I told him it was cool for him, but I couldn’t rock the guns. Not in this country, not at this time. He agreed and we chuckled at what a silly world we live in.

Buzzfeed, feel free to add “the privilege to wear whatever you want to for Halloween” to your list (~;