On Sleep Struggles, Podcasting, + Building Community With Drew Ackerman

If you’ve ever searched for podcasts that help you fall asleep, odds are you’ve stumbled across Sleep With Me, a wildly popular show hosted by Drew Ackerman—in character as “Dearest Scooter”—and featured in The New York Times, The New Yorker, Buzzfeed, and Dr. Oz. In this (grown-up) bedtime story podcast, Ackerman, who himself suffered from childhood insomnia, takes a cue from late-night comedy radio to tell short stories about everything from his take on the Great British Bake Off, to his childhood as the oldest of six children, to his past jobs as the fruit fly monitor for the State of California and librarian for one of the country’s largest jails. His goal? Tell random, non-stressful stories that help people feel a little less alone at night and more easily fall asleep.

We caught up with Drew to learn more about his history with sleep struggles, what his evening and morning routines look like, his perspectives on the stigma surrounding sleep, and more.

I’ve gone through different periods of just trying everything out of desperation and frustration. And being like, oh please let this work because I NEED to get some sleep. I was almost trying to force it to work instead of it being a journey of discovery. And then after starting the podcast and reading more about sleep, my personal journey shifted and I thought…oh, maybe this isn’t something that has one fix or maybe I could be a little bit softer about it and not have so much pressure. Because even as a kid, the pressure to fall asleep almost made it impossible to do so.

So what I focus on now is a bedtime wind-down routine, and then I see the sleep space as more like a buffet in the sense of…hey, try this and see if you like it or if it works for you. And then maybe go over here to this station and try this instead of thinking that one thing is going to work for everybody.

I definitely have not got the “no electronics” down yet, but I do focus on the physical part, so I’ll try to either foam roll or stretch, and then also meditate—not for super long, maybe 5-10 minutes. I also sometimes do a gratitude list or a fear list, or I just journal. And then reading is really important. I don’t know if it necessarily puts me to sleep, but because I read fiction, it feels less like “work” than some of the other stuff does. Some days I just don’t want to foam roll or I’m not feeling super grateful…I just don’t feel like journaling. But if I have a good book, reading will be the last thing I do before I go to sleep. I normally read until I get really tired, and I don’t pressure myself to go to bed at a certain time. So if I want to be in bed by 11pm and I start reading at 10pm, if I read past 11pm, it’s okay because I’m already chilling out.

Yes, I do find that a morning routine is important too. After waking up, I open the blinds in my apartment to try and get some sun to come in. Then I do some journaling or I write what I dreamed about or what I’m worried about for the day. Then I try to meditate a bit, before stretching or doing yoga…anything to get my body going.

Don’t get me wrong, I’ve been resistant to this stuff, so I imagine people reading this will think…oh no, not more work. But it really does help start my day out right. It’s downtime before I start running around. I can put things into perspective before they go out of perspective.

I would tell them to think of it like someone’s talking to you that you don’t necessarily have to listen to, but you could if you need to. I don’t want people to feel pressure to listen, which is why I think about the show as “barely listenable.”

And if you’re just starting out, I would tell you to begin with the recent episodes. We have three distinct styles of shows that we alternate between: an ongoing story series with recurring characters (the one we’re finishing up is called spice friends, which is Godzilla-meets-My-Little Pony), random episodes (which could be a made-up story or a personal essay), then a TV recap (we did Great British Bake-Off, now we’re doing Dr. Who, then we’re going to do Ted Lasso).

Exactly…but with a spin! That’s really important for me, because when I’ve tried things in the past to fall asleep, it feels like my internal mechanisms are weaponized against me. So if I’m listening to just one sound every night—like a campsite with rain falling on the tent—it’ll work for two nights, but then my brain will be like…oh no no, I know what this sounds like. There’s going to be thunder in five minutes. Let’s start worrying again.

So I like to have a familiar structure with the podcast, but make it different every time. So then those parts of the listeners’ brains don’t know what to expect. They’ll know I’m going to talk about something weird, but they don’t know what it’ll be. I imagine that’s what keeps whatever parts of us are keeping us awake, off.

Well I think the stigma around sleep comes down to a combination of things. If someone’s living with their family or a partner or a roommate, it’s rare that there are two insomniacs together in one room. And if there are, they may have different styles. So most of the time when you’re sharing a room with somebody, it’s this weird reminder that even if you both have to go to work or school the next day, they’re sleeping soundly and you’re not. And that can feel lonely, even though you’re not physically alone—it’s a different style of loneliness because you’re there dealing with this by yourself.

And the flip side is parents or partners or friends who do sleep well having trouble putting themselves in this space of desperation not being able to sleep. And I don’t think they ever mean it to be dismissive or presumptive, but occasionally the reaction can be…oh, well why don’t you just not think about anything then you’ll fall asleep just fine? Or—if someone has chronic pain—well why don’t you just not think about the pain, then you’ll fall asleep? It’s difficult to make them understand that it doesn’t work that way, which can also trigger this loneliness even though it’s nobody’s fault.

When you want to be able to control something—and you think you should be able to control it—and you can’t, it can hurt in a way. Because if you’re thirsty, you can get a drink. But if you want to get to sleep, you just can’t do it. There’s a weird kind of powerlessness to it, and the harder you try to control it, the more frustrating it can be.

It’s this idea of community, and what that can look like in the digital age, how it’s a two-way street, and what my responsibility is. Whether it’s the community around the show of people who are suffering and can’t sleep in the deep dark night or the community of people who are powerless…what does it mean to be part of a group?

I’ll get emails from people suffering from things I’ve never dealt with, like soldiers with PTSD or people with chronic pain or someone suffering from the tragic loss of a loved one. And I think…okay, I’ve never experienced that or I’m not experiencing that right now. But I can relate to some of what you’re feeling, and that has given me a new way into empathy and compassion, which is the opposite of powerlessness. It feels like some form of service—albeit nothing huge—but I do like to think it builds community. Because I know how painful not sleeping can be, and maybe I can help and maybe your life will be a little bit better or more manageable. I realize that, on a global scale, the impact is miniscule, but there is still an impact. That is the small scale idea of service and community that I try to carry into the podcast.

Are you on team single pillow or double pillow?

Double, definitely. I actually have four—two flat pillows and two puffy pillows. This way, I can alternate all night.

Do you remember your dreams?

Not always, but at least a couple times a week.

Do you dream about real-life things that have happened?

The more stressed I am, the more my dreams will manifest as rote tasks. For example, I’ll dream about spending eight hours stacking boxes, then they’re falling down and I’m re-stacking them. And I’m not actually doing that in real life, but it’s because I’m stressed about something like having to do my taxes, for example.

Are you a night owl or an early bird?

I hate getting up early, so I prefer to be a night owl. But the reality is that I definitely get up at like 6:30 or 7am, so I try to just listen to what my body is telling me.

Give us our sleep elevator pitch! Why should people care about improving their sleep?

When you can’t sleep, my experience is that life is much less manageable, and then every little thing becomes harder to deal with. Even small things get magnified because I’m not well-rested.

Related articles

12 Best Podcasts To Help You Fall Asleep
Dr. Jessica Shepherd Shares The Most Common Sleep Myths She Encounters
3 Best Essential Oils For Sleep, According To Science
7 Breathing Exercises For Better Sleep

Trending articles

Are Sleep Problems Hereditary?
7 Best Teas For Sleep
Does Vitamin D Help With Sleep?
How To Properly Take A Nap: Benefits, Tips, + FAQs