Simon has spent the last 15 years in tech and media, most recently as the Director of Design at Patreon, and as a design leader at Google Maps and TIME Magazine. Simon’s devout involvement with the conservative subculture of the Catholic Church gives him first-hand experience of the ideas, tactics, and personalities impacting young Catholics and their mental health. His podcast Dear Alana is an unraveling mystery and a poignant spiritual memoir about teenage rebellion and spiritual manipulation, the price we pay to belong and the systems that pay no price at all. Apple selected Dear Alana as one of twelve “Shows We Love” for 2023.

I felt compelled to make Dear Alana after learning about the story of this young woman who lived a life that seemed parallel to my own.

About a year into independently producing the show, I had already done a number of interviews and was prepared to be fully indie. But I shared the pilot with Tracy Leeds Kaplan at Tenderfoot and she loved it. And that’s how our partnership started.

One important thing for me in figuring out who to partner with was that the team itself would be really small. The big reason was that the show is so personal, it mines a lot of material from my own life that I wanted to safeguard. I needed to find people who understood me and could draw that out of me in a way that would preserve the vision I had for the show—which was to keep it very personal and vulnerable.

I know myself. Having a room full of people with opinions may not be the most conducive environment to write the show. One of the beautiful things about Tenderfoot was they understood the environment I was looking for and were very supportive.

I think that was special and rare to find that kind of environment to make this kind of show.

I’ve been a design leader and design director at places like Patreon and Google and Time Magazine, I’ve worked in creative environments before. The amazing part about making things as a team is the energy exchange between the people in the room who are all invested in the vision and are contributing their own thoughts, and everyone is riffing off of each other.

My challenge was…how was I going to convey this tangle of things I felt inside that I wanted to communicate in this project, and the vision that I had for it in terms of its tone and style?

The show is about belief and belonging. The magic was seeing other people get hooked into this world, who may not have shared the same religious or cultural experiences the subjects were enmeshed in, but could connect with the story in other aspects of their own lives. 

My original plan was to be the voice, a narrator that tells this story as I investigate what really happened to Alana. We ended up cutting together three episodes and having a feedback session with folks whose opinions we trusted. We got them in a room and had them listen to all three episodes and just had a freeform conversation about feedback. And the overwhelming consensus was: Who’s Simon? What are his stakes? What’s his story? That really opened my eyes to the necessity to inject more of myself.

I had been prepared fully to take a lot of my stories and secrets to the grave. But after hearing that feedback, it was like, okay, people do need to know who I am. And so that led me to progressively disclose more. And that was a journey.

Alana is a real presence in my life. I think the trick she played on me was like, hey, you’re going to tell my story. But in the process, I’m going to help you confront some of the things in your past that you wouldn’t otherwise have done if it wasn’t in the service of telling my story. Which I think is generally how a lot of us probably work, right? It’s so much easier for us to do things for other people or see what’s happening more clearly when they’re happening to other people than when they’re happening in our own lives. 

It all happened so quickly that I don’t even think I was fully aware of what was going on. Within the first week, the show hit number one on Apple podcasts in the US and Canada. In its first month, it had a million downloads, and there were dozens of write-ups and reviews. It was a bit of a high and I was just trying to keep up with it.

Maybe the second or third episode had been released when I was at Podcast Movement in Denver in August of 2023. And people were recognizing the show there. I certainly wasn’t expecting this kind of reception, and I wasn’t expecting it to get out so quickly to so many people. (continued below)