I Used to Think Meditation Was Stupid

The line between boredom and enlightenment is surprisingly thin

I used to think meditation was stupid. None of my close friends were meditators. It seemed boring and pointless. I was a busy guy, I didn’t have time. Besides, my knees hurt if I sit cross legged for any length of time. It felt silly. I hate breathing through my mouth. What does ‘clearing your mind’ even mean?

But I kept reading in the media about the importance of mindfulness and the popularity of meditation, so every once in a while I would download an app like Headspace, sit cross legged on an armchair and try to close my eyes and meditate. 30 seconds later my eyes would snap open and I would think, “this is stupid.” I eventually got it up to 2 minutes, but it was still stupid. I didn’t feel any different, it was not for me.

But people kept telling me how amazing it was. If I ever mentioned I was interested in trying out meditation, people in the line at Starbucks would start talking about Vinyasa Flow, Transcendence, and Chakras. I couldn’t even keep my eyes closed for five minutes, please stop giving me advice.

I Find a Billionaire Guru

I was at a venture capital conference in Cancun and the keynote speaker, a billionaire, announced at the end of his speech that he would be leading a meditation group on the beach the next morning at 7am. He got my attention when he said, “I used to think meditation was stupid, then I thought it was difficult, then I figured it out.”

That sounded a lot like my situation so I thought I’d join the group. At 7am I dutifully showed up, crossed my legs in the sand, and paid careful attention when he asked the group to gather around and watch him demonstrate the power of the mind. He held up a necklace between his fingers and through sheer mental focus, made the necklace begin rotating in small circles as it dangled. One of the other participants pointed to his fingers and said, “hey, you’re moving your fingers!” I thought, “bad showmanship, but let’s get on with the meditation.”

Created in Midjourney

The special meditation technique turned out to be closing our eyes and listening to an audio program he had created and was selling. I lost any faith I might have had in billionaires knowing what they’re doing, long before Twitter became X.

But people keep talking about meditation. What was wrong with them? Or with me?

Then one day two years ago my friend Neeraj mentioned a technique for meditation that he heard from Naval Ravikant. Something like this, “just sit quietly in a room with your eyes closed for one hour a day, for 60 days. Don’t try to guide or quiet your thoughts, just sit there with your eyes closed and try not to fall asleep. After 60 days, your mind will naturally quieten and … you’ll be a meditator. He said 60 minutes was easier than 30 minutes or even shorter durations.

Neeraj said he was going to try it. It was a challenge and I figured I could do anything for 60 days so why not? I agreed to join him, and we would compare notes every day. It was also the height of COVID-19 stay-at-home quarantines, so I didn’t have much else going on. It still seemed pretty daunting though — a whole hour? Every day?

The first day my legs hurt and I fidgeted non stop. I made it through the 60 minutes but it was torture.

The second day my legs hurt again so I decided to try meditating lying down. I fell asleep after 20 minutes.

The third day I managed to stay awake the whole hour, after finding a sitting position that worked for me without crossing my legs.

The fourth day I found myself kind of looking forward to the session. I played some mental games with myself, and at one point saw a purple haze that morphed into a wormhole in space and I floated through it. That didn’t happen again for a week, but it was very cool.

Created in Midjourney

By day four, I was able to make it through the hour more easily, but spent a lot of the time wondering how much longer I had to sit there. I discussed this with Neeraj and he said that he had set up a timer that would chime every five minutes and that really helped him get through the hour. It sounded vaguely like cheating to me, but I used the Insight Timer app on my iPhone to set it up, and wow, did it ever help! It’s not cheating, trust me.

Somehow, wondering how much of the five minutes was left allowed my mind to drift to other thoughts more easily. It still wasn’t easy, but this one hour was fast becoming my favourite part of the day. I thought of it as an entire hour focused entirely on me.

In the following weeks, I continued to experiment. I actively controlled my thoughts sometimes, working through a particular problem I was having at work. Hey, Naval never said I couldn’t guide my thoughts! Other times I would focus on my breathing, catch myself falling asleep or imagining a future vacation, and go back to my breathing.

After 30 days, Neeraj called me up and said, “Dude, I think I’m done, I can’t do a full hour every day.” I was enjoying the hour so I just thanked him for introducing me to it and continued on my own.

This is really important for me to drive home to you dear reader: it didn’t work for him. There is no technique or approach that will work for everyone. This is as true for meditation as it is for yoga, exercise, or studying for exams.

Here is the only secret to succeeding at meditation:

Keep trying different approaches until you find one that works for you.

After 60 days I experimented with reducing the meditation time to 45 minutes, then 20 minutes, then 10 minutes. I kind of liked 20 minutes, and now that is my standard meditation time. I don’t do it every day, and I don’t do it at a fixed time. I do it when it occurs to me and I have the time, which is about every second day. It works. I feel more calm and centred, and when I’m in a line or waiting for something to happen, I’m able to easily close my eyes and slide into a calm breathing pattern, feeling recharged after even just a few minutes.

Find a meditation approach that works for you. There is no right way to do meditation.

I’m still not sure why meditation works. I have a rough theory that being deliberately bored for 20 minutes makes the rest of my day seem more exciting. Also that letting my thoughts run rampant for a while stops them from running rampant when I’m supposed to be focused on other things. I don’t know the mechanism, and frankly it doesn’t matter. I’m happier and I enjoy it, and the results became obvious within a week of starting.

Naval’s method worked for me. It or another method might work for you. I’d be remiss in not pointing out that a year before trying this experiment I had done my first deep dive therapeutic psilocybin experience with 5 grams of dried mushrooms. Experienced meditators have said that the mental state reached through ten years of meditation practice is quite similar to that reached in four hours through psychedelics.

It seems to me that my body was more able to relax and enjoy meditation after experiencing psychedelics, but I don’t have any real evidence for that. One aspect of the psychedelic experience is a sense of knowing certain things without a rational thought path to get you there. Even if you’re intent on reaching some version of enlightenment solely through meditation, having a glimpse of what it feels like via psychedelics can only motivate you, not derail you.

The line between ‘enlightened’ and ‘endlessly bored’ is surprisingly thin, but you can cross that line by experimenting and finding a technique that works for you. It’s worth the effort.

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