7 lessons from an intensive meditation session


I just finished a one-day intensive Vipassana meditation session in Madrid.

This is my fourth experience with deeper meditation sessions. My first was a four-day walking meditation retreat in Thailand. Then a heroic dose of magic mushrooms in Cape Town. In Argentina, I joined a three-day breathwork course followed by a three-day silent meditation retreat.

As always, I am amazed at how important silence is for seeing yourself clearly. We have so many scripts running our lives, and the only way you can rewrite them is by becoming aware of them in the first place.

I’ve also been meditating for 45-60 minutes per day this summer (explained below).

Here are seven realisations that have jumped out at me.

1. What you are looking for is love

Over the past decade, I’ve built my dream business, got in great shape, travelled the world, enjoyed great relationships, learned to write, and more. These are all fantastic things, but I’ve chased a lot of it from an underlying sense of insufficiency. There is a part of me that believes I am not enough unless I prove myself worthy.

This is a tiring way to exist.

I struggle with this less these days (three years of inner work has helped). But I’d be lying if I said it still wasn’t there—old patterns die hard. But I’ve realised underneath the things I chase externally is the desire to feel loved. And actually, life is a lot easier if I just learn to love myself.

Self-compassion ain’t as sexy as self-improvement. But the more you love yourself, the less you need external approval, the easier it becomes to live authentically. Ironically, this is a better way to get what you are chasing anyway.

2. Trying to hold onto an experience ruins the experience

I notice when I am meditating, I often hit points of deep calm and bliss. I’ve had glimmers of incredible energy that comes when you are not stuck in the past or future.

These moments are great, but they are cut short because I try to keep hold of them. I tell myself I need to remember it, or write it down, or bring it more into my life. Before I know it, my mind is back to overthinking again.

This ‘grasping’ is a core part of human nature: we are scared to lose what we have. Ironically, this makes us lose it anyway. You have a great month as an entrepreneur, then freak out when you can’t replicate it. You find someone you like and start being clingy, pushing them away.

There is real strength in just enjoying whatever life serves you, without getting wrapped up in it. That includes both the good and bad.

3. Suffering is just a story.

I don’t mention this so much, but I’m often dealing with chronic pain in some shape or form after my brain and spine surgeries.

Earlier in the summer, I had one of my worst flare-ups. I could barely write, exercise, or travel. It sent me to a dark place because these are the things I love most, and it is really f**king hard to stay positive when every moment reminds you that you might have problems in your life.

I began worrying about loss of identity and the future implications of my health issues. Maybe I won’t be the writer I want to be. Maybe I can’t see the world. Maybe I won’t be ‘loveable’ due to whatever problems I am wrestling with.

But meditation saved my life here.

It has helped me recalibrate. I realised that there is what happens and the story of what happens. My mind was spinning tales that were ungrounded. And pain, actually, is a beautiful gift. If you have ever experienced it (physically or emotionally), you know how it can bring you into touch with reality. Like David Whyte wrote in his beautiful piece, On Pain:

“Pain is the doorway to the here and now.”

Because I could not work for a few months, I meditated for at least an hour a day. This let me see my struggle a little more clearly (there are people in much worse situations—and I only have neck pain because I survived the surgery). Ironically, when you are grateful for your problems, the story stops, and the pain drops.

The mind-body connection is incredible.

On that note…

4. A tense body means a chaotic mind

In the first thirty minutes of the meditation session in Madrid, my mind was in the usual overdrive mode.

Business projects, finishing my book, deciding my next country.

All mental chatter. I used to try to ‘stop myself’ from this, which was rarely effective. I would just end up overthinking about my overthinking.

These days, if something is on my mind, I check in with my body. I know that if I am overthinking, my left brow is lightly furrowed and my shoulders are tense. My neck juts forward slightly, and there is a little knot sitting at the pit of my stomach.

When I relax these things, the thoughts melt away. I don’t have to ‘try not think’. It was just my mind and body stuck in a feedback loop.

I did not know this until I started somatic work. I wish I had been taught it when I was a lot younger. It has improved my decision-making ability massively.

If you want to calm your mind, calm your body.

5. Stop fighting so hard

Last week was my fifth anniversary after quitting dentistry to be a writer. To prepare for a live training, I reflected on my accomplishments. I travelled the world, made over $1.5m, wrote a book, learned Spanish and more. This is beyond what I dared dream about as a dentist. And yet, I haven’t enjoyed the journey as fully as I should have.

I have a perfectionist streak that stops me from being present. Probably out of fear that if I enjoy success, I won’t be able to continue to achieve it. But tightly grasping life is exhausting, and is actually less productive anyway. My best results have come from doing the things I love with a smile on my face anyway.

The truth:

We think we have a lot of control. But this is just another story (if you look deep enough, we’re all trying to fight the fear of death—and trust me, it’s coming regardless of how many vitamins you take).

Reality is like a river. It’s flowing in one direction. Your job is to just gently row the boat down the stream.

6. Welcoming fear makes fear fun

I am pretty deep into researching fear at the moment. A lot of the reason I’m travelling is that you are constantly outside your comfort zone, which is a great mirror for awareness.

I joined this meditation retreat because it was in Spanish.

My Spanish is pretty shit. I can speak conversationally if the recipient is polite enough to deal with my idiocy. But this event wasn’t for tourists. There were thirty or so locals. Everyone was speaking fast, and I had no clue what was going on half the time.

At the end, you are invited to share your experiences. The shy introvert in me cowers and cringes at these moments. But fear is such a fun experience if you welcome it. Who cares how stupid you look when you feel so alive?

I stumbled through several minutes of Spanglish as I explained some of these realisations. They probably thought I was a nutter, and they would be half right.

7. Inner work is just as important as external work

I used to find meditation such a chore. It was a ten-minute tick-box in my hustle bro optimisation routine. I only cared about stacking external results because a measurable scorecard is an easy substitute for deeper meaning.

But this year, I’ve really fallen in love with the inner work.

I no longer see it as separate from pursuing my dream, but essential for it. If you do not look inwards, you will waste your life living out scripts that you could have rewritten.

Fear. Anxiety. Insecurity.

You will not solve these internal wiring issues with external results. There is a version of myself in an adjacent reality still blindly chasing validation and running away from all the things that have made me sad, angry, scared, and feeling small.

Now, I’m no monk here.

I still find it hard to say no to things. I still worry about what people think. I still beat myself up for previous mistakes.

But my relationship with my behaviour has changed. I’m learning to love the parts that I used to judge, which has led to more transformation in three years than a decade of self-flagellating self-improvement.

Most importantly: it has helped me have the courage to go after my dream of writing, even if future success is uncertain. For me, that makes meditation worth every moment.

Thinking for yourself

I know it is hard to set aside time for this stuff.

But if you can’t shake this feeling that something isn’t quite right, that there is deeper scratching below the surface, that you are living out an existence that you did not sign up for…

Then I cannot recommend enough that you SLOW DOWN AND LOOK INWARDS.

Seriously. You just need to see, and change starts to occur. If you told me this a decade ago, I would have ignored you, so if you ignore me, I understand it too. But if I had started much earlier, life would be much more aligned.

I recommend reading Awareness by Anthony Demello to kickstart this journey.

Then, Think on These Things by Jiddu Krishnamurti (this is my most-read book; I summarised it on YouTube here).

Although you don’t need to read too much. Your mind will teach you more than any book, and it is more interesting than any movie.

If you’ve had similar experiences, I’d love to hear from you. Reach out. I reply to every email :)

Kieran

P.S.

I leave Madrid today.

In the back of my mind, I am searching for a place to settle. Perhaps not all year, but changing countries every few months has been tiring. Another realisation I had recently is that I crave connection, so it may be that I need to update my life to the new plan.

Madrid is a great contender.

Food, architecture, museums, people. It has everything I’m looking for.

But I don’t know why South America sings to my soul.

So my plan is to enjoy a week in Valencia. I’m flying my mum out so we can enjoy our first holiday together in a decade. Then it’s Morocco for a wedding, England to stock up on Yorkshire tea, and back to Paraguay to renew my residency. Then I’ve booked Buenos Aires and Colombia. After that, I have no clue.

Looking forward to sharing more of how life unfolds.

If you enjoyed these insights, some articles from previous experiences:

Kieran Drew

On a mission to become a better writer, thinker, and entrepreneur • Ex-dentist, now building an internet business (at ~$500k/year)

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