Drew Ackerman on Building His World of Dreams and Momentum

For years Drew Ackerman has hosted Sleep With Me, a podcast that aims to help people who, like, have difficulty falling asleep. Using his trademark creaky dulcet tones, Ackerman spends over an hour each episode walking a fine line of being just interesting enough to be entertaining for those who can’t fall asleep but also just boring enough to lull those on the edge into unconsciousness. Now for the better part of five years he has been telling bespoke “episodically-modular” longform stories, building a pseudo-canon across various worlds all built on foundations of dream logic and improvisation. I sat down with Ackerman to discuss his process in acting as creator and caretaker for a show where, best-case, listeners are falling asleep during episodes.

"Sleep With Me, even as a listener, kind of its own has its own small set of rules, but then there's also the rules of telling the stories. There's the world in which all the stories exist, some of which overlap and some don't. It's really a fun playground to be able to play in. Even though there's a lot of rules, there's also a lot of freedom."

Whether discussing a VHS copy of Raiders of the Lost Ark or taking listeners on a trip to Trader Joes, Ackerman has spent eight years honing his ability to take any conversational tangent and run with it. Plenty of podcasts, mindful of listeners’ attention spans, go so far as editing out their own ums and ahs, but Sleep With Me’s storytelling permanently takes the scenic route. While there are previous episodes in which Scooter (Ackerman’s nickname/pseudo-fictionalized hosting alter-ego) would embark on entirely fictional adventures or invite on other characters to share their own experiences, in 2016 Sleep With Me marked the beginning of a new format, with Nuns in Space.

The series, ostensibly about a Freestyle Coca Cola machine gaining sentience and exploring a cloud of delusion (like many things in Sleep With Me, that is literally what I mean. They fly around a cloud made of the concept of delusion) in space along with his best friend Scooter. Nuns in Space takes full advantage of the kind of storytelling freedom you only get when your audience is on the edge of their own dreams. This wacky series introduced “episodically modular” stories into the Sleep With Me canon. Full seasons of stories interconnect, but are also written with the intent of not punishing listeners who skip (or successfully fall asleep during) any given episode.  

"There really isn’t [a show bible], and that’s because of the train-building I’m always doing. I’m glancing back or listening to some old episodes, but I don’t necessarily have the time to be able to listen to all of the old seasons, so there’s inconsistencies. But [the train ride of listening] is for the audience that’s down for that. Even when I get feedback [on the inconsistencies], for the most part it’s playful 'Hey, did you know this?' And I’m like, “No, I had no idea that character said that,' or 'That is wrong, you’re right!'"

The ever-evolving complexities of the SWM universe can be tricky to keep front-of mind as more characters enter the rotation, but if listeners decide to give up their quest to keep everything straight, they’re in good company–Ackerman doesn’t always, either. A valuable tool in working with such an unwieldy beast for Ackerman is giving oneself permission to be okay with being wrong. For instance, during the annual 2020 Macy’s Thanksgiving Parade recap (an annual event hosted by a rotating cast of SWM characters), Ackerman brought back a pair of Game of Thrones characters Scooter had previously extricated to the real world to spare them their extremely Game of Thrones-ian fates.

As Ackerman explains, “[Messing up sometimes], that’s just like, the reality of the show. [Sleep With Me] is so ridiculous [on its own merit]. Technically, I kidnapped Tommen from Game of Thrones in some fanfiction machine I designed right before he-... I can’t remember if I kidnapped him before [spoiler redacted] or the season before when I felt bad for him. I took him to this world along with his bodyguard Ser Gregor, though I don’t even know how he got to this world. I then had them move in with my neighbor. I could be prosecuted in multiple universes for that kind of behavior!”

There was just one problem: a big part of Tommen’s plot, once freed from his television existence, is that he changed his name. Ackerman, put on the spot, could not remember the name. Which was fine, because, as Ackerman explained "Then it's like, even more fun that it's like, okay, now I can't even remember what you renamed yourself, even though you live next door to me. It's like in character for me on the podcast, and in real life to be like, Wait a second, Why can't my–why is my brain not recovering that information?"

After eight years of constant production, Ackerman has generated quite a bit of information to keep track of, and hasn’t stopped refining new ways to tell his sleepy stories. As of this writing Ackerman has continued that momentum of writing and experimentation with a currently in-progress episodically-modular series featuring a brand new set of characters playing Dungeons & Dragons, adding an extra layer of character work and roleplaying to the already substantial Sleep With Me world. To close out our conversation, I asked Ackerman what anyone considering starting a longform story or universe should consider from the beginning.

"[It’s important to find] all the ways you can take care of yourself through the process of longform fiction, if you're making a long term commitment to it. [And asking yourself] 'How am I going to take care of the little kid in me that wants to tell these stories through this long and winding process?' Part of that is getting to know yourself, and I think that's an opportunity in figuring out [if one’s] obstacles are internal or external. Like, for me, a lot of obstacles are  self-created stuff, or just the way I view things. For other people there's more external obstacles or a combination of both. How are you going to take care of yourself through that process?

The one most specific thing that's really worked for me is having a regular place where it's okay to stop, okay to change, or okay to take a break. And [deciding whether to do] that on a monthly basis or on a goal-based basis. Just to be like 'Hey, do I still like making this? I know I committed to making this whole universe, and I really wanted it. Do I want to keep doing it or not?' Having the permission to stop has kept me going. It keeps my inner critic at bay and gives me a chance to be like 'Okay, I really do want to keep doing this, or I really do like this.' It’s okay to be imperfect.

I always tell people who ask ['Where do I get started?']: do you think you could set aside five minutes a day? Do you think you would set aside 15 minutes a day? If you have an idea, just start there. I can guarantee you that if you do that, if you write more days and than not with that 15 minutes set aside, you're working on it. Some days, it's gonna suck, but it's gonna build momentum. That’s how Sleep With Me came about. There's a lot of mornings where I'm like, 'Ah, I don't know. This is the part I don't like,' or 'Oh, yesterday, I couldn't come up with that thing.' Okay, well, let's start the timer. That's what I do when it's not going well. 'Okay, let's start the timer. Can I do it for 10 minutes, can I get through 10 minutes? Can I get through 15 minutes?'"

Gavin Gaddis is a freelance journalist and podcaster. They've worked as a media critic in various positions since 2011. You can find them on Twitter or at The Pod Report.