We last chatted with Brennan for the blog eight years ago, and since then things have really popped off. For those who don’t know (though it’s hard to believe anyone drawn to our camp wouldn’t), Brennan is the creator and executive producer of Dimension 20, which is an actual play tabletop RPG show, as well as a performer and cast member on the streaming service Dropout. And he’s great at it! He and the Dimension 20 team have had an extremely successful tour of the US and UK, and recently SOLD OUT Madison Square Garden! He can hardly believe it: “It’s nuts and that’s my job,” he told us, but we really don’t think so. We knew Brennan was going to do amazing things.
Brennan’s been impressing us with his world building skills since he was very young. Like many of the people interviewed for this blog, he has brought numerous Adventure Games to life; for a time he even had the record for most written Adventure Games, though he was recently dethroned by another staff member (Go Mike!). Brennan’s Games have had a major impact on this community. One that holds a special place for him, and MANY other community members is Finals, a modern day magic school Adventure he co-wrote with his brother in 2006. Finals’ legacy is still felt today, having spawned an additional five Games written by Brennan and other staff (the most recent being run just last summer), and influencing many more. We weren’t surprised that Brennan’s found so much success because his work has impacted our community for so long.
Brennan has put so much into this community, but he often attests to much he’s gotten out of it as well. He was the Story Overseer at our Advanced Camp many years ago where we ran five Adventure Games in twelve days. He helped the other four writers get their games on their feet, as well as his. This task gave him a great place to jump off from for his professional career. “The fact that by the time I was in my twenties, I had what felt like a centered and stable emotional relationship to working very hard and fast on something creative and how to not be precious about your creative self. Like, game is gonna start Wednesday night come hell or high water. So you need to stop thinking of creativity as precious, it’s not a little feathery thing that dwells in the soul. It is the craft of getting the work done and making it as good as you can with the time and resources that you have. And I think that that is a very welcome gift to anybody that wants to pursue creative endeavors of life.”
Brennan has worked very hard to get where he is today, but his path hasn’t been easy. Right after our last blog post, he moved out to LA. The crew of Wayfinder friends who all shared an apartment in NYC disbanded. Recently dumped and having some cash from being on Who Wants to be a Millionaire (go watch the episode), he chose to move. Having nothing left in NYC, he felt ready to take a risk; but he might not have felt ready if not for another lesson he learned at Wayfinder.
“My first staff game,” Brennan told us, “was a zombie horror game. I remember being deep in character and moving around. It was one of the first times that I wasn’t being led around by a PC leader. I was walking down the road and I had a flashlight on ’cause I was walking in the dark and I needed a flashlight to see. As I had this flashlight on, I heard zombies down the road. They run up and a lot of people [playing zombies] just jump on me and kill me. And I remember thinking, ‘oh, I had my flashlight on.’ I was totally visible from everywhere. I think that there was a moment of growth. I was like, ‘oh, even though the light is comforting to me, it’s gonna kill me. And for me to be safe, I have to push, for me to be actually safe, I have to do things I’m uncomfortable doing. Even though it will frighten me to be in the dark, I’m actually safer in the dark than I am with this flashlight. Things that feel like safety sometimes are not safety, and things that feel dangerous are sometimes the thing that is going to save your life.’ That was a moment of viscerally learning as zombies tackle me to the ground and eat me.”
Moving to LA was a risk, just like turning off the flashlight, and at first it didn’t feel like it was paying off: “The first year that I was out here was horrifyingly lonely. I auditioned for stuff and didn’t get it. I had been on a Harold team in New York, and I auditioned for a Harold team in LA, and I didn’t get it. I was devastated.” He tried out to be a cast member at CollegeHumor, Dropout’s predecessor, and didn’t get it either. He was feeling low. “It was the first time in my life that when my mom called to ask me how I was doing, I said, ‘I don’t think I’m doing very good, Mom.’ I had been doing badly before, but I’d had the wherewithal to lie. I did not have the strength to lie.”
But soon after that phone call, Brennan got an opportunity, and he says his skills from Wayfinder helped him capitalize on it. The folks at CollegeHumor hired him to be a question writer for their game show, Um Actually. “And I went, ‘Oh my God, I can do that. I can write nerdy questions.’ And then a few months after that, they hired me to help write Troopers. And I was like, ‘I can do that.’ And then a month after that, they hired me to be a cast member. And then a month after that, I pitched Dimension 20. And the rest, as they say, is history.” It’s a classic; never give up, and once your foot is in the door show them how amazing and useful you are. “What Wayfinder prepared me for was being ready when the opportunity came. I knew how to work hard. I knew how to be in meetings, collaboratively, how to work with other staff in a place. I knew how to take care of the feelings of people around me while getting the work done…. Because it’s actually not about the individual game, or the individual project, or the individual workshop. It’s about the holistic experience of camp. Every department is significant. Everybody matters. Everybody’s doing an essential job. I think, when I got to CollegeHumor, I was hopefully, and maybe people would disagree with me, and if they do, oh my God, I’m so sorry, but I feel like I was ready to be in a big place with a lot of moving parts, and I know what I was needed to do.”
The rest, of course, is history. But still, Brennan says that, although he has more resources on Dimension 20, it feels a lot like working at camp. “The conversations always stay the same. The resources of Dimension 20 are very different from the resources of Wayfinder circa 2009. You are always going to be creating at the edge of your ability. I have never experienced an amount of resources making a creative team go, oh, we can relax. That’s not how it works. The resources come in, add quality, add energy, add an expansion of your ability to accomplish something. So when you get resources, like a gas, you just expand to the edge of your resources and are once again battling the limitations of what it is you can do. So to be honest, the emotional experience of jumping into the resources of Dimension 20, it feels identical to Wayfinder.”
Besides moving to LA and making so much great programming, Brennan has had some other amazing changes in his life: he met and married the love of his life, and they recently had their first child. When we asked what his favorite activity is, he said, with such joy, “playing with my child, playing with my little child. Being a dad is the best!” We don’t think it was ever a secret how much Brennan dreamed about being a dad, and it is clear to us that his dream is better than he knew it could be. His other joys in life are not far off from his job: “doing improv shows with my wife and with my bud, Lou Wilson.”
We feel so grateful for the time, work, and effort Brenann put into Wayfinder in its early days to help it become what it is today. Though a lot has changed, Wayfinder’s heart is still the same. And that is the part Brennan credits helping him the most. “I really don’t draw on anything as much as I draw on my time as a staff member at Wayfinder, and as a camper Wayfinder. The relationship of the cosmic, and mythical, and whimsical, and magical, and adventurous, and what it means to be in a person in community, be responsible to people, work hard, and work hard for a place where you believe in the cause that you are working for, that’s all Wayfinder, baby.” We couldn’t agree more, baby!
Written by Trine Boode-Petersen, Edited by Matt Nusbaum from an interview in 2024