Who opens the gate?

Because no one is paying me to build block towers

“I hate to be a wrong generation guy but I really can’t believe I missed safe cocaine, car phones, and buying pitches in the room.” - My friend Ben who makes movies (not me, different guy)

In the house I grew up in, there is a “room” we lovingly referred to as The Loft. The Loft is this oddly shaped platform that sits in the back half of the house above the hallway and laundry room. Two sides of The Loft are open to the floor below, the only thing that stops one from falling overboard on these two sides is a railing. A, presumably, custom built ladder drops down into the hallway below with an entrance to The Loft blocked off by a gate.

When opened, the gate makes a bit of a creak and when closed there’s a distinct click. The Loft has served many purposes over the years: storage, cat shelter, and my favorite one: play room. The Loft was a dedicated zone separate from my bedroom where I could play with legos, build block towers, lay down toy train tracks, and so on… It’s where I made my first foray into video games. It’s where I had sleepovers. It was a sanctuary of fun.

I was not permitted to go into The Loft to play willy nilly. I had to meet certain benchmarks in order to be allowed to open the gate. Had I done my chores? Was I on my best behavior? Was I doing well in school? My parents served as the gatekeepers. There was no lock on the gate, but as you’ve now read, it was not easy to sneak past the noisy entry.

That physical space represents a haven of creativity for me. It was a place where I would let loose and build without purpose, creating plans for empires I would rule over and then topple because wooden blocks are fun to topple. In a way, The Loft was the first place where I experienced the flow state: a creative zone where time and meaning falls away and all that matters is the work in front of me. Distraction-free, worry-free, bliss. My dad reminisces fondly of this time because I would unknowingly whistle a tune while I played. It was a reminder to him that I was safe and okay, because I was.

My playtime evolved over the years, especially when I discovered computers. I filmed some of my early videos in The Loft, but I edited on a computer. My passion drifted slowly from the physical Loft to the virtual world. I’m not making block towers anymore, it’s videos for the internet that has consumed my creative attention.

I often day dream about the path I’ve taken to this moment. I knew early on that I liked making videos - I know I knew as early as The Loft Days. I am so fortunate to have had the realization of what I wanted to do for a career so early in my life. It came from following my passion. I kept trying different ways to tell different stories. I experimented with my parents’ Hi8 tape first before I graduated to MiniDV tapes and eventually digital cameras. I had permission to try and fail over and over again.

I no longer have to be on my best behavior, or do well in school, or do my chores for the metaphorical gate to open, but I’ve realized that there are still gatekeepers in my life represented by people and situations.

I saw firsthand what it took to make movies and television. I saw through my own father how much work had to be done on one facet of the production. A Location Manager, simply put, is responsible for… well…. managing the locations (shocking, I know). You can’t make a movie if you don’t have somewhere to shoot it. Not only do you need locations to film movies and TV, you need places for the cast and crew to park. If you’re not familiar with the job, there’s a fantastic piece of media that explains the whole thing here (my dad is Tim Hillman, he’s kind of the star)

I decided in High School that I would not follow the traditional Hollywood path. I had the support system and nepotism working in my favor to go that route, but it was kind of because of it that I zagged instead of zigged.

My personal experience in making movies involved one person: me. I would often be the star of my own movie, the cameraman, the editor, the distributor. I found (and still find) such joy in being involved in the entire process. I was not interested in joining a world where one plays only a small part in a big production.

It looked like it would take a lot of dues paying before I could move up the ranks enough to be able to tell the stories I wanted to tell. I saw Hollywood as Gatekeep City, preventing me from going into The Loft even though I had done all my chores, schoolwork was not an issue, and I was on my best behavior. I love that world, I celebrate it, I want it to thrive and flourish, but it’s not the world for me.

It’s not like I could have just kept playing in The Loft, creating for creating’s sake, without a care in the world. Benny’s gotta eat, Benny’s gotta pay rent, Benny’s not comfortable with people calling him Benny unless he feels super close to you so unless you’re going to pay my taxes, dear reader, it’s Ben.

Since no one was employing block tower builders and I shut off the entertainment business option, I left the door open to whatever else would let me make movies on day one of my post-college career. As luck would have it, I found a place like that in CoachUp, a startup in Boston focused on athletic training for youth and adults. So there I was, making my own worlds, living my dream, getting paid to make movies, and I didn’t have to slog my way through the Hollywood machine.

But just because I escaped the traditional gatekeepers did not mean the work I created was without new ones.

While I’m grateful to have been able to create movies right away, it still has taken me a long time to work on exactly the kind of media that I want to create. There were still dues to be paid. I had to sacrifice the kinds of stories I wanted to tell because my job required me to tell other ones. I don’t begrudge this. It’s logical, it makes complete sense for my labor to be given in service of another’s vision. I also sort of like the challenge of it.

My second job out of college was for a company called (at the time) Price Intelligently (It’s not managing location level of obvious but I’m sure you can figure out what we did). I remember I ended my last interview with:

“I don’t know what does it, but I’m definitely interested in figuring out what makes pricing sexy.”

I don’t know if saying that is what got me the job, but it definitely didn’t lose me the job. And it represents the challenge I had for my early career: I had to figure out how to take topics that weren’t inherently interesting and make them interesting. I wasn’t telling my own stories, I was working with other people to tell their stories.

Yet lately, I’ve been itching to get back into The Loft.

I often wonder what would have happened if I didn’t choose this path. What would have happened if I tried to become a member of the Hollywood elite and make my own movies. There’s no way of knowing what making the other decision would have looked like (the butterfly effect and all that). However, I can imagine I would have found similar frustrations with the gatekeepers over there.

Many of my friends are still in “The Biz”, one of whom, Ben (again, not me), is a creative executive for a production company. I’ve learned from him that telling stories there still requires lots of waiting, people, and, of course, gatekeepers. And if you can tell by the opening of this piece, it has only gotten harder. I wouldn’t know what makes safe cocaine good for getting movies made, but perhaps it would make “buying the pitch in the room” a more impulsive and easy decision.

I feel fantastic writing this column, dear reader (hi Vinny!). Perhaps one day I could do this full time, but that’s only going to come if I continue to show up and earn your time spent reading. I feel like I’ll do that if I continue to get better.

Welcome back to The Loft.

I’m glad you’re here. I’ll see ya next time.