Put this up as a blog post because so many friends have asked me about this and i wanted to scale my answer. Here ya go!
I’ve had a long journey with sleep routines and performance. Starting in college i experienced a major bout of disregulation that had me wide awake tossing and looping with hyperactive thoughts, tortured by the need for sleep and the inability to turn off my brain and take a break. This led to a cycle of sleep-anxiety, palpable fear of how the lack of good sleep would ruin my next day and turn into a cycle of anxiety and sleeplessness.
At different times for the next 20 years I would have flare-ups. Often I could sleep just fine, and then for weeks at a time this sleeplessness would return. I learned to cope by sometimes embracing the nighttime active-brain, and just getting up and doing work, watching movies, or otherwise taking a break from being in bed, awake, and caught-up in the anxiety. This was “managing” my problem, but not really a solution.

Then about a decade ago i discovered the CURE in an unexpected moment. Cristina started to use a podcast to go to sleep, in which a man reads nonsense sentences in a monotone voice endlessly. She found the voice soothing and as a routine, formed her “sleep ritual”. The particular podcast didn’t work for me at all (in fact it was annoying!). But. it got me wondering about a podcast-ritual that might work for me. My challenge was mostly not falling asleep, rather, it was falling BACK asleep when waking up at 2 or 3 am.
So: i explored getting a pair of “bedtime headphones”, and coupled these with a series of podcasts — which work like a MAGICAL ELIXIR. I am now on gen3 headphones that are delightful, and have found my sweetspot with podcasts.
For headphones I now sleep with the Ozlo side-sleeper buds. I fall asleep on my side and tend to flip left/right side throughout the night (well, when my cat’s aren’t on my chest or next to me–wouldn’t want to disturb their sleep!). These buds (a) last 12+ hours (b) have a killer feature where they transition to white-noise sounds, after i fall asleep (they sense when i’m asleep), (c) i can wear just 1 and switch between ears periodically–this allows me to still have situational awareness to hear my alarm/etc. but also (d) help reduce the distraction of my wife’s (sometimes) sleep-apnea soundtrack, (e) are really comfortable even when my head is against the pillow. These are my 3rd product and best i’ve found for my needs. I highly recommend–have been using my first pair for 3 years, they are workhorses and I use almost every night.

For podcasts… the trick was to find a mixture of content that i could tune into and focus on, and, a voice/style of chatter that was conducive to (a) helping me FOCUS on the podcast (to minimize my racing mind thinking about work, social drama in my life, etc.) (b) being interesting but not SO interesting that my mind can transition to sleep-land (c) routine oriented with fresh new episodes/content on a weekly basis, so I have something that feels new each week.
These criteria led me trough several history and literature discussion podcasts, to where i now have ended up which is sports and cinema. Go figure?
Dan Carlin’s Hardcore History podcast, specifically his 6 part (12+ hours) episodes about the war of the pacific in World War 2 — AMAZING — was my gateway. I love his content, and his voice. So i would drift off and then come back the next night, got me through about 5 months of sleep routine! Whether for sleep or otherwise, this podcast is awesome and the Supernova in the East on Japan / WW2, one of the most interesting things i’ve ever listened to.
Bill Simons is my GOAT, I like his voice, and he talks about sports with great guests on his main podcast (the Bill Simons Podcast) and then with some film nuts, talks about old movies on The Rewatchables. He releases sports episodes several times a week and a film episode 1x a week. I use these each night to get into sleep mode, asleep (usually in 10-15 minutes), and then crucially BACK to sleep usually 2-3 times a night when i wake up. I just hit play on my ipad/phone, and am usually back asleep within 5 minutes.
yeah–totally wacky… BUT, IT WORKS! i feel like i have a newfound super power.
