Limitless Lifestyle

What to think about to go to sleep...

By Jonathan Roseland  Connect    


Sleep hackingThis is going to be little bit different than all these pieces of content about sleep hacking - the supplements, the sleep masks, the orange sunglasses, the apps - in this article I'll address a really common sleep issue that people report - which is that they can't get to sleep because they have all these thoughts running their head.

I've had an lively mind and an over active imagination for as long as I can remember; which has led me to lead a life of adventure and novelty seeking. The unfortunate downside to this is that also for almost as long I can remember I was on the insomnia spectrum; getting to sleep has always been challenge. There is always just so much to think about!

As a teenager I remember wondering what should I be thinking about to go sleep?
This was before the age when you could find a really helpful answer to that sort of question by just Googling it.

I would read these different self help type books which would say that...
Before falling asleep you should think about what you're going to do the next day or write down a challenge you're dealing with.
This really did not help my sleep as I would then spend hours tossing and turning worrying about what I was going to do the next day to overcome whatever I was dealing with.

I had also heard that you may want to repeat a mantra like
Relax... Relax... Relax...
That you want to try to "self talk" hypnotize yourself to sleep
You're going to sleep Jonathan... You're getting sleepy... You're going to sleep Jonathan...
These really did not work for me. I felt really silly repeating mantras or trying to talk myself into falling asleep and then I would get frustrated with myself.

When I got into Entreprenuership in my early 20's my mind was constantly formulating business plans and marketing strategies. Sometimes I would come up with (what I thought was) a really brilliant business idea at around 11:45PM and would think about it for hours and hours getting more and more excited; around 5AM I would give up on sleep and just get up, get some coffee and get to work.

In my mid 20's which was about 5 years ago my insomnia was as bad as ever and I actually needed to drink myself to sleep; not like a half bottle of Vodka a night but I needed like a glass or two (or three) of wine to get to sleep.

Fast forward to today and I've almost totally overcame this issue and I have more to think and worry about than ever. It would be an understatement to say that my domain of concerns has expanded. Yet I fall asleep consistently without the aid of drugs or booze, I'm very rarely tormented and kept from slumber by my thoughts.

What changed? Well, I do use some of those sleep hacks, they really do help, but as a digital nomad a lot of them don't fit into my lifestyle. I figured out what to think about to actually fall asleep, the key is...

Non-stimulatory Thinking

(To invent a cool phrase!)

Going to sleep you really want to think about things that don't excite you, ideally you actually want to be a little bored. Which is a little bit counter intuitive to modern life; nowadays everything about life is trying to make sure that we are constantly amused, entertained or enraged. It's actually really important to spend a little bit of time every day being bored.

What are some examples?


This is probably the most quintessential example of non-stimulatory thinking; either the vipassana style or the Blue Sky Protocol will clear your mind of thoughts that excite you. Doing 20 minutes of meditation before bed really will imbue tranquility and can be a serious game changer for your sleep life. You may even fall asleep while doing the meditation.


A pretty none-stimulatory thought exercise is to go on a time travel journey through your own personal history. With your reminiscing, as opposed to just letting your mind wander, you want to focus on sequences of related of memories, such as:

  • Apartments or houses you've lived in.
  • First dates you've been on.
  • Places you traveled on vacations.
  • Lovers you've had.
  • Favorite articles of clothing you've owned.
  • Video games I used to play.
  • Jobs you've worked at.

Go through the sequence from your earliest memory to the most recent; it should be a little monotonous.

Visualizing physical action

In your head you can practice the moves of some physical exercise you do; it could be a weight lifting technique, martial arts, yoga, whatever...
Personally I do salsa and latin dance so in my head going to bed I often practice the latin dance moves I've learned recently.

Practicing vocabulary

If you've learned a second language; you can think through the vocabulary and grammar you've learned. You can try to construct phrases or translate song lyrics that have been in your head.

Audio enablers of slumber

You may find that your mind just keeps defaulting back to more high valence thinking; your inner dialog beats you up about your bad decisions and grapples with the challenges you'll face tomorrow. What works really well for me is to listen to a podcast or audio book about some subject that's not very stimulating. In particular
Stefan Molyneux's Free Domain Radio - Viewing society, culture and current events through the lens of empirical philosophy.
Dan Carlin's Hardcore History - Really thorough story telling and analysis of major historical events.
Both of these guys have kind of soothing voices and a melodic cadence that will talk you to sleep. I would not listen to a podcast that had a lot of audio effects, jokes or entertainment value while trying to go to bed.
There's these audio tracks of really soothing music that help some get to sleep, listening to podcasts or audio books has always worked much better for me though.

The Power of Non-stimulatory Thinking

I'm reading this autobiographical book by this Finnish engineer who invented the smart phone in the early 2000's.

One of the things I found interesting is that right from it's inception the smart phone was intended to be a drug.

The establishment engineers at Nokia in Finland thought that mobile phones should just be a convenient tool to make phone calls but this young inventor, Johannes Väänänen, imagined this engrossing, compelling and even addictive experience that could be provided by a device the size of your hand.

Buddhism has for thousands of years sought to banish suffering from the world, and it would seem that is has a very long ways to go in that endeavor, but Johannes's invention has nearly banished boredom from the world in just a little more than a decade.

We may still use the word boredom; but we actually use it to now to describe the opposite state of mind from boredom. We'll spend 30 minutes or an hour (or more!) jumping between applications, reading the news, sending an SMS to a friend, browsing Twitter and watching a funny video. We are so stimulated that we can't hold our attention on one thing for more than a few minutes.

You may think I'm not addicted to my smart phone the way a junky needs cocaine or oxycotin!

Perhaps you remember the scene from the movie Eyes Wide Shut where he gets into this crazy secret society ritual orgy. If you ever wanted to actually go to a party like that, you would want to find a No Phone swingers party.
The first time I went to such a party was a few years ago in Medellin, Colombia. An amigo and some girls I knew invited me to this secret bar. I took a taxi to an address and I had to knock on an unmarked black door on a deserted street to enter, I was then informed that I would be leaving my clothes and phone in a locker. I paid the cover, was given a towel and directed to a hot tub.
That night easily ranks in my top 5 most hedonistic experiences but there was some undeniable acute separation anxiety from not having my phone.
You may not be into swingers parties but it's worthwhile to try going to a social event without your smart phone or maybe you could organize your own No Phone party (clothing optional?)
You'll experience that there's kind of an anxiety curve to being smart phone-less, at first it just doesn't feel right, you'll keep reaching for your pockets. You'll fidget a little more, needing to give your hands something to do. I imagine that it's not all that different from someone who just needs a little bit of heroin daily to function.

You are likely highly stimulated all day, everyday, if not by your work, study or family then by your computers, smart phone or television. It's important to spend a little bit of time every day being bored. It's important to include some non-stimulatory thinking in your day:

  • It will allow your mind to follow a thread of thought for more than 30 seconds. In what's become our default state of browser tabs, notifications, apps and videos competing for our attention it's difficult to think thoroughly about a single topic for until we reach our conclusion or decision.
  • It turns down the volume of mental static which allows your default network to deliver up creative solutions to problems to your conscious mind.
  • It allows you to transform information into knowledge; to take the things you hear and see and integrate them into a holistic understanding of the world and your place in it.
  • Non-stimulatory thinking can be a game changer for your sleep. If you suffer from insomnia because thoughts run relentlessly through your head as soon as the lights go out; you're doing too much stimulatory thinking before bed. Check out the article I just wrote on What to think about to go to sleep...

How is non-stimulatory thinking done practically?

  • I live downtown and at the end my work day or sometimes at noon, I'll just walk around for 10 minutes, taking in the sights and sounds of the city.
  • Reading intentionally and thoroughly. This is the opposite of browsing a Twitter hashtag about the most recent terrorist attack. I try to spend 30 minutes a day reading something dense with the intention of understanding a deeper nuance as opposed to just being amused; usually a none-fiction book about technology, science, history or philosophy.
  • I spend approximately 25% of my workday listening to zero content music; either the lyric free algorithmic music of Brain.FM or classical music. Next to smart drugs this is probably my best biohack for focusing on a project for hours at a time.
  • For many doing exercise, lifting weights or doing yoga alone in silence doubles as a beneficial mindfulness practice.
  • Journaling, the old fashioned way with pen and paper, focuses your problem solving and introspective powers on the important things in your life.
  • If you're a guy you can do tantric self cultivation, if you're one half of a couple you can do orgasmic meditation with your partner.
  • Perhaps you do meditation daily - that's a good habit - although meditation is often focused either on the body or own keeping the mind clear of thoughts.

I said earlier; it's important to spend a little bit of time every day being bored. Most people are totally stimulated from dusk till dawn everyday. I'll challenge you to try to spend 30-60 minutes a day being bored; usually at the end of the day and see how much it improves your mood, focus and productivity the next day.
I've noticed a marked difference between...
a) If I turn off my Internet connection; read for 30-60 minutes while having a tea, then stretch for about 15 minutes and go to bed.
b) If I've spend an hour or two before going to sleep watching Youtube videos or reading articles about crazy things going on in the world, using Twitter and messaging friends.
The former just about guarantees that I'll start my day right, make better decisions, allocate my time better. With the latter I find that the next day upon awakening my attention is really fractured; my discipline is poor and I'm not nearly as productive as I could be. It's not true that a night of sleep is a fresh reset of your mood and attention; how you spend the very end of your day definitely has an effect on the beginning of the next.

Try being a little more disciplined about the last 45-90 minutes of the day and you'll see for yourself!

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