Busy Mind Keeping You Up? How to Mindfully and Peacefully Drift Off to Sleep


I’ve always envied people who sleep easily. Their brains must be cleaner, the floorboards of the skull well swept, all the little monsters closed up in a steamer trunk at the foot of the bed.” ~David Benioff

I can feel the night converting into day. Hooting owls pass the baton to chirping birds before flying off into the slowly fading night. Low-grade panic sets in as total silence gives way to minor stirrings, and I realize my time to carve out at least a tiny patch of sleep amidst this mostly sleepless night is running out.

These words, which I wrote during one of my first face-offs with insomnia back in college, aren’t reflective of my life-long sleeping patterns. Sleep and I hadn’t always had such a complicated relationship. As a child, I’d nod off without any struggle, pretty much as soon as I entered my bed. It wasn’t until I reached early adulthood that it started playing hard to get with me.

Sometimes sleep’s elusiveness could be attributed to my surroundings. Like many young adults, I’ve resided in a fair share of environments that weren’t the most conducive to restful sleep—whether it was the house in Montevideo, Uruguay with twelve housemates who liked to blast reggatone music at 3 AM, or the apartment in the heart of San Francisco’s Mission district where garbage trucks, drunk people peeing (or puking) outside my window, and music blasting from nearby parked cars constituted the typical nighttime cacophony.

External factors weren’t the sole cause of my sleeplessness, though. A lot of times even if my room or the street was relatively quiet, a clamorous mind kept me awake.

While I still have trouble sleeping some nights, practicing mindfulness has made a significant overall difference. For anyone else who’s at times plagued by a revved-up night-time mind, here’s some of what has helped me.

Read before bed.

Ideally material that won’t over-activate your mind. Cramming your brain with new information or revving the analytical wheels may prevent it from relaxing, making for a more difficult transition into sleep. That said, the newspaper might be best reserved for starting your day with (to wake the mind up) while fiction may help to calm you down.

I’ve found fictional stories provide a smooth transition into dreaming. Reading a short story or novel, all cozied up in your blanket, takes your mind off of the day’s stress and helps you relax, physically and mentally. If reading the newspaper is like climbing a hill, immersion into fiction is like slowly submerging one’s self into a jacuzzi.

Recent books I’ve read that have helped guide me into sleep were The Island of Missing Trees, narrated by a sensitive and observant fig tree (I could feel my thoughts slowing down the more I got pulled in to the story); and Crying in H Mart, poignant and evocative in its exploration of a nuanced but deeply loving mother daughter relationship, with mouth-watering descriptions of Korean food.

Practice free association.

As I lay awake certain nights, the thoughts trundling through my mind tended to be: “Don’t think these things. Stop worrying. Go to sleep.”

As I found time and again, though, telling yourself not to do something proves far less effective than providing an adequate substitute or stand-in for the habit or behavior in question. So what might that substitute be?

After reaching an impasse, we writers often engage in free-association to unearth new ideas—the only rule being that we keep typing, documenting any thought that comes our way without forecasting ahead to the possible outcome.This allows our mind to relax, creating space for new ideas to flow in.

Applying a comparable technique to your night-time mind can result in a similar effect. Instead of abolishing my thoughts, I’ve shifted now to giving up my attachment to any one of them, focusing more on letting them flow in and then out.

Allow nonsensical or loosely related associations to pass on by through your mind without judging or obsessing over them. Maybe a regret from your day brings up a random embarrassing memory from seventh grade. Maybe a worry about tomorrow evokes an irrational fear of getting sick in a meeting. Let your mind go wherever it goes.

You can think of it as a night club, yourself as the bouncer and your thoughts as the guests. Rather than make your venue into a snobby, selective place, allow it to be all-inclusive. At the same time, don’t provide the guests with any compelling reason to stay. While it’s natural to feel uneasy about letting in certain characters, you can rest assured that they won’t stay for very long if you don’t engage with them.

Once I adopt a more permissive mentality, the motley crew starts finding my night club lame and boring. They’re used to VIP service, so my negligence simply doesn’t appeal to them. Barred from free food, drinks, and preferential treatment, they vacate soon enough—leaving my mind quiet, pristine, and more welcoming of sleep.

In short, the monkey mind wherein thoughts run rampant is not what’s to be feared. It’s the lingering on any one of these thoughts that we could benefit from shifting away from. Because it’s when we’re trying too hard to control our minds that it often remains awake, vigilant, and filled with tension.

Don’t despair.

In some cases, deeper exploration and more individualized analysis is necessary to address the underlying issues, as insomnia can at times be only one symptom of a deeper-rooted health problem.

Other times, though, as Alain de Botton wrote (even while acknowledging that insomnia that lasts for weeks “can be hell”): “In smaller doses—a night here and there—it doesn’t always need a cure. It may even be an asset, a help with some key troubles of the soul. Crucial insights that we need to convey to ourselves can often only be received at night, like city church bells that have to wait until dark to be heard.”


While these aren’t full-proof remedies by any means, the primary nugget I hope you’ll take from them is that similar to many things in life, the more we adopt a drill sergeant mentality, the more elusive sleep becomes. The gentler and more permissive we are of our minds before nodding off, the likelier it is to descend upon us. As Ronald Riggio put it, “My expectation that eight uninterrupted hours of sleep is required was a big part of the problem.”

I once wrote in my diary, “My body tenses up—the opposite of what it needs to do in order to achieve sleep. <— ACHIEVE sleep. That word choice alone reflects your misguided approach. Sleep is something you SURRENDER to. Leave the achieving for your job or future marathons.”

So the next time you’re tossing and turning, try surrendering yourself to free-association. Maybe the next place it takes you to—amidst all the random corners the mind inevitably traverses—will be the [restorative] kingdom of sleep.

About Eleni Stephanides

A queer bilingual writer, Eleni was born and raised in the Bay Area. She has been writing since elementary school, where she handed out her stories and magazines to her classmates. Her work has been published in The Mighty, Thought Catalogue, Elephant Journal, and Uncomfortable Revolution. You can follow her on IG eleni_steph421 and read stories from her time as a rideshare driver at lyfttales.com

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