How Failing A 10 Day Silent Meditation Retreat Was More Successful Than Succeeding.

Medicine Path - how failing a 10 day silent meditation retreat was more successful than succeeding


Just as the Buddha taught that everything is impermanent, so too was my initial decision to remain for the entire 10 days at a Vipassana silent meditation retreat. My meditation teacher laughed when I broke the news to him, exclaiming he’d never heard anyone frame their decision to leave like that before!

If the word Vipassana is unfamiliar, it means something to the effect of ‘clear insight’ in Pali, the language of the Buddha. The reason one would spend 10 days of silence in this retreat would be to practice the Vipassana meditation technique, which essentially involves placing one’s attention on both the inhalation and exhalation of the breath, and the subtle sensations one feels in their body.

With 10 hours of meditation each day for 10 days, beginning with a gong at 4am and ending at 9pm, one increases their focus and attention on their bodily sensations, cultivating deeper levels of self awareness and gaining the experiential wisdom of impermanence; all things one experiences in life, and everything in general, is momentary, passing, fleeting, temporary, transient, forever changing.

Sometimes we experience that which is pleasurable, sometimes we experience that which is not-so-pleasurable. It seems to be an inherent program built into our system to desire the pleasurable, and avoid the unpleasurable. We want the things that feel good, and we don’t want the things that don’t feel good.

Makes sense right?

Life doesn’t work like that though. It’s inevitable that we go through things that are uncomfortable. Things that are painful. Whether that be emotionally or physically. If we're always resisting the unpleasant and clinging to the pleasant, that's a fantastic way to create suffering in our lives. So if you're into living a life full of suffering, do that!

The 'good' and 'bad' are always coming and going. We experience both polarities. It's part of the natural ever-changing ebb and flow of reality. This meditation technique is said to help guide one to the path of equanimity; releasing one from the throes of suffering. Non-resistance. Non-attachment. Non-judgement. Non-reactivity.

Not resisting the unpleasant. Not becoming attached to the pleasant. Not judging or labelling anything as 'good' or 'bad'. Instead, being able to observe things objectively for what they are; creating the spaciousness between stimuli and reaction; to be able to choose our response, leading one to a state of non-reactivity. A state of being where one can instead cultivate love, kindness, peace and compassion.

Medicine Path - how failing a 10 day silent meditation retreat was more successful than succeeding


So why on Earth did I decide to leave early? First off, it's certainly not an easy feat. It's seriously hard work. Full respect to those that have completed a Vipassana course. Leaving on Night 3 wasn’t a decision that I made lightly, and there were many factors I had to disentangle and contemplate. In essence though, honestly, I was completely overwhelmed. Physically, mentally, and emotionally.

While I was there to undertake some serious brain-training, and to undergo what my teachers framed as a form of 'surgical operation' on the mind, I couldn't help but contemplate if it was really my time to undertake this process. It was voluntary after all. It wasn't as if I'd already drank my first cup of Ayahuasca for the night and was in for four or five hours of relentless purging whether I liked it or not. I held complete responsibility over my decision to stay or leave. I had the ability to remove myself from that environment at any moment. And the fact that I couldn't resign myself to a decision led to relentless inner conflict.

One reason I continue to work with shamanic healing medicines and psychedelics is to practice surrendering in sometimes challenging and unpleasant situations; to continue to cultivate a state of equanimity that I can carry and embody outside of ceremony. But because surrender was so incredibly difficult in this instance, I knew there was some investigation work to do. It was time to get out my magnifying glass, put on my detective hat, and figure out what was going on.


In between practising the Vipassana meditation technique, I was see-sawing from one thought to the other, one feeling to the next. Jumping hoops from thinking I should stay, to feeling I should go. Back and forth. Formulating each side of the argument; weighing up the pros and cons, trying to understand the reasoning behind my persistent thoughts and feelings.

I had to discern whether my decision to leave was a choice based out of fear, and not wanting to deal with what was coming up physically, emotionally and mentally during the retreat, or if this was a choice based on self-love and doing what I knew was in my best interest. The teachers framed the 'surgical brain operation' of Vipassana like this:

"The first day of meditation we are making the incision for the operation, and slowly the puss starts to rise up. Over time, more and more of the infection bubbles to the surface. It can be a very painful process, however we know that this must be removed to ensure our well-being."

The thing is, I had a feeling what this operation would bring to the surface. I had experienced these wounds during the time of my first Master Plant Dieta, working with both Ayahuasca and Chiric Sanango. Isolation. Loneliness. Sadness. Grief. Disconnection.

I'd worked through some of it during my time in Dieta, which I liken to a Vipassana retreat on steroids: Noble silence, no entertainment, no music, no books to read, no communication with the outside world, no soap, no toothpaste, bland vegetables for every meal, no fats, no sugar, no salt, no spices. Just time away in isolation, consuming these plant medicines and learning what they had to teach.

I knew I hadn't processed all of that trauma though. Down in the dark crevasses of the mind it lay, waiting for another chance to become known.


I soon tapped into one of the reasons why my intuition was telling me to leave. I'd cracked open some of these same wounds working with the cactus medicine, Huachuma, just prior to entering this meditation retreat. Wounds that stemmed from my early childhood that needed healing; changes, feelings and intentions that I needed to process and integrate into my life.

The integration that I needed through my recent plant medicine journeys was connection. Reconnection. With family. With loved ones. With community. This integration included being in warm, nurturing environments. To be embraced by the connection of others around me. To open my heart and let it soften in my interactions with family.

Being in this meditation retreat was the exact opposite of what I needed when it came to my current integration and healing journey. What was best for me, was to not be in a cold, isolated, seemingly disconnected environment. It further highlighted the significance of proper integration. The importance of preparation & integration cannot be emphasized enough. I detail this in Sacred Psychedelics. Sometimes the very advice we pass on to others can become a bit of a blind spot for ourselves.

I knew there were processes I needed to undertake after my work with the cactus medicine, however I entered into this meditation retreat with a warriors mentality; to dive head first into another challenging situation, and process it all once I was done. I could recognise that part of my identity was wrapped up and attached to a particular label: someone who embraces challenges like a warrior, heading into battle to meet with adversity, knowing that pushing my own boundaries leads to self discovery and growth.

I also realised that sometimes the warrior only has so much to give. By adding more challenges onto one’s path without proper integration, it can unnecessarily and sometimes disastrously prolong the healing process. Some of this was articulated brilliantly (which I'll paraphrase) in the conversation between Ultra-Spiritual-Guru JP Sears and Aubrey Marcus, on Episode #107 of the Aubrey Marcus Podcast:

"A workout doesn't make you stronger. The recovery from the workout makes you stronger. If you pound yourself into complete obliteration, that might take you even longer to recover. It's just like over-training. You can over-train the psyche, just like you can over-train the body.

Having that knowledge of pacing is really a brilliant caveat for the Stoic philosophy of 'The Obstacle Is The Way.' You just have to be careful to not give yourself too much obstacle that you run yourself into the ground."

When I listened to this a few days after leaving Vipassana, it resonated pretty deep. They spoke of the wise courageous warrior not being afraid of the battlefield, but acknowledging that they only have so much capacity; knowing that what may be challenging later down the track, is overwhelming to them now. When one is already processing enough fire, they may need to digest the initial fire before encountering other flames.

As JP Sears put it, "We need this humbleness rather than this delusional sense of grandiosity..." And indeed that is part of the reason why I felt compelled to stay - a delusional sense of grandiosity. I told myself that I'd be staying here not just for my own benefit, but for my loved ones, my family, my friends, my clients, for anyone I come into contact with. Similarly, like working with the shamanic healing medicines, I do the work not just for myself, but for the good of all. And then on the other hand, I was thinking that part of the reason for staying was so I wouldn’t be perceived as (and feel like) a quitter. A failure. As someone with a weak mind. Someone who couldn’t hack it.

As a facilitator, a mentor, a teacher, a leader, what image of myself would I be putting out into the world if I left early? If others knew that I failed, would I lose respect? Would I lose credibility?

The feelings and thoughts of external validation had crept into my mind, and once I could finally see this fear with greater clarity, it actually helped to reinforce my decision to leave. These are all just momentary roles that I step into. Roles that contain within them various archetypal patterns and energies. It’s easy for the egoic mind to get these roles confused with the true self.

I was, and still am incredibly humbled in knowing that I wasn't ready to complete this challenge; that I'm just another human with my own limitations. In that humility, I found great strength and courage in being able to step beyond the fear, beyond the embarrassment, beyond the disappointment, beyond the external validation, and honour my own intuition, self care and integrity.


I’ve come to know that reframing perspectives to see the positive in seemingly negative situations is one of my great strengths. To be able to see the advantage in adversity. To see the lessons and teachings in challenging and overwhelming situations, whether completed or not. It is here that I can see my 'failure' as such a powerful teacher.

My failure was in fact, a complete ‘success’.

It taught me more about integration, about listening to my intuition, about self care and self love. I deepened my meditation practice by coming to know more shadows and darkness within. I was humbled. I learnt the difference between being challenged and being overwhelmed.

Through being overwhelmed, I had powerful cathartic experiences; releasing a stack of the same stored emotion I let go of during my cactus ceremonies just prior. Allowing myself to cry deeply, and not bottling it up, led to further softening of my heart, which has been incredibly beneficial to me on my healing and integration process post-retreat.

[Let's just take a moment to acknowledge the fact that it's incredibly healthy, and normal, for men to show emotion, to cry, to show vulnerability. Don't let anyone tell you otherwise. Our vulnerability can often be one of our greatest strengths. In the circles that I facilitate, men showing emotion, men being real, men opening up to vulnerability, is more than okay; its encouraged and whole-heartedly welcomed.]

I gained more of an experiential knowing that failure can teach us the way, by showing us what isn't the way. Sure, if I had absolutely no choice I could have endured the 10 days of suffering. I'll never know if I would have come out the other side unscathed and healed, or beaten, bruised and broken.

I intend to complete the retreat in the future, but for now, it's not my path. The time will eventually arise, and what was for now overwhelming, will one day be a challenge overcome. I'm thankful I had the experience I did during my short stay at the Vipassana 10 day (3 day really!) silent meditation retreat. It was the perfect amount of time for me to gain the clarity and insight I needed to keep progressing along this path in a healthy, sustainable, wise manner.

May these insights provide clarity to others in reframing their own negative experiences, thoughts and beliefs; to seek the lessons, teachings and wisdom on their own paths of adversity. For now, I leave you with this:

How can you positively reframe the biggest challenge or obstacle you're facing right now in your life?

Medicine Path - how failing a 10 day silent meditation retreat was more successful than succeeding

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Chris Kelly4 Comments