Welcome to this edition of The Wise Founder.

A newsletter for thoughtful technologists.

Of all the things I’ve written over the past few years, what follows is by far and away the most popular, both in terms of readership and response.

And to me that’s an interesting data point, because it’s not about founders or startups and laced with actionable insights - it’s the story of a 10 day silent meditation retreat.

Why that?

Well firstly there’s the intrigue - perhaps it represents something different, that stands out from other content?

What about the quality of the writing? I not-so-secretly hope this plays a factor. I wrote this from a place of mental clarity I’ve rarely experienced before or since and spent plenty of time trying to make it good. The end result was, and still is, something I’m proud of.

What about the algorithms? Well maybe that too. The black box of magic that determines whether content goes viral or dies on the vine is one of life’s great mysteries.

But beyond these factors is another, deeper hypothesis - the struggle to find meaning in our times.

I look around and see a lot of societal and cultural thrash as many of us search desperately for anchors of significance. The things we stay connected to that give us meaning.

Of course there are the obvious places many of us go looking - in a job title, a paycheck, a fancy house - but soon we come to realise that as good as those things can be for providing stability and comfort, when it comes to meaning they rarely even scratch the surface.

So off we go on the next phase of the adventure.

And perhaps that’s the moment we’re in. The next phase of the adventure. A time where so many of the historical anchors of significance - family, religion, community etc. are evolving, and we’ve yet to figure out what fills the void. Things that talk to this are interesting.

Or maybe it’s just the algorithms?

Either way, I felt compelled to write a brief followup. The original essay is included in its entirety below for those that missed it the first time around. It was written in October 2023 shortly after the end of a 10 day Vipassana retreat. At that point in time I was still living in the liminal space between retreat and the real world, digesting much of what I uncovered.

And now here we are almost 2 years on. What’s changed? What hasn’t?

Well let me firstly confess that I’ve not kept up a Vipassana practice (a recommended 1 hour in the morning and 1 hour in the evening). Meditation is still a part of my life but my practice ebbs and flows, is informed by many different styles, and never reaches a 2 hour daily time commitment.

My mind has slipped into some of its old patterns, albeit with a greater awareness when that happens and what I can do to change it.

And my phone usage…well it’s still more than I’d like in truth, but with at least the intention of some sacred time at either end of the day where it’s simply switched off.

What has stuck though are two things:

1. Mental resilience - one of the key ‘lessons’ of vipassana practice is on the origins of suffering. To paraphrase, it’s the idea that our suffering comes from resisting reality - avoiding what’s there and/or grasping at something different as opposed to just being with things as they are. I don’t always live by these lessons in the messy day-to-day but I still feel tapped into a deeper well of internal resilience borne out of this insight.

2. Understanding how much control I have over my own mental state - I described this in the original essay as like ‘peaking behind the curtain’ at another way of being. That once you strip away all the day-to-day noise, our mind’s default state is actually one of peace. I knew at the time that I wasn’t destined to live the other side of the curtain. I don’t want to run away to a monastic life. But knowing that underneath it all, that’s what’s there for me has been supportive in ways I find it hard to fully describe.

Alas, I still never found out who Bjorn was.

Did I get enlightened yet?

A bell rings. 40 men start a slow, silent walk, heads down, making no eye contact, past a small building with a sign that reads ‘male cells’. Yard time is over. In the distance another bell can be heard, and 40 women living a parallel existence do the same. I begrudgingly make my way towards a large building in the distance, mentally counting the days until my release, before reminding myself that I’ve chosen to be here. Those cells aren’t for imprisonment but for meditating in. This isn’t prison, it’s a vipassana meditation retreat. At this precise moment, those things feel like one and the same to me. I just have to remind myself that this feeling will pass.

For most people, the word ‘retreat’ conjures images of relaxation, yoga, matcha lattes, superfood bowls, and all of the other Instagram-worthy moments of the wellness industry. This is not those things.

A Vipassana retreat typically lasts for 10 days (although returning students, the enlightened, and the criminally insane can opt for up to 60 days in some cases). Each day runs by a strict schedule:

• 4am - wake up bell

• 4:30 - 6:30am - meditation

• 6:30 - 8:00am - breakfast & rest

• 8:00 - 9:00am - ‘Adiktan’ meditation sitting (meaning ‘strong determination’ in which the aim is to not move at all during the hour, despite your body screaming at you in pain)

• 9:00 - 11:00am - meditation

• 11:00am - 1:00pm - lunch and rest (this is your final meal of the day)

• 1:00 - 2:30pm - meditation

• 2:30 - 3:30pm - Adiktan meditation sitting

• 3:30 - 5:00pm - meditation

• 5:00pm - cup of tea and piece of fruit

• 5:00 - 6:00pm - rest

• 6:00 - 7:00pm - Adiktan meditation sitting

• 7:00 - 8:15pm - Evening discourse (watching a video talk)

• 8:15 - 9:00pm - meditation

• 9:30pm - bed

This is serious. It’s brutal. It’s relentless.

And yet, the centre can’t keep up with demand. After our course is due to finish, the next 10 day course starts only 3 days later and is once again fully booked. As are all the courses for the remainder of the year. And the same seems to be true for the other vipassana centre in the UK, and the many more worldwide. The courses are free to attend (with the option of making a donation entirely at your own discretion after the course is finished) but even so, who would willingly sign up for this? Why?

Well in my case there were a number of reasons:

1. Personal curiosity - I love to learn and go through unique experiences, and I knew a number of people who spoke highly of vipassana. The more something sounds like a bit of a mad experience, the more I find myself drawn to it.

2. Professional curiosity - I was interested to see if anything would come up that would give me some insight or way of being that would allow me to continue to improve as a Coach.

3. Solidifying a meditation practice - I’ve had an on-again-off-again relationship with meditation over the years. Through my yoga teaching I’ve had plenty of exposure to different realms of meditation and have gone through phases of different practices. Almost all of them have been incredibly good for me. None of them have stuck long term.

4. Desire to change certain patterns of thinking and behaviour - this spanned from the deeper level e.g. my mind’s tendency to overanalyse situations in an attempt to control the uncontrollable; to the more practical e.g. spending less time on my phone.

5. Processing some past trauma - I’ve written previously about how the abusive relationship of a family member had a big impact on me. I’ve done a lot of processing over the years and felt in a good place with it all but was also fairly confident it would come up if I spent 10 days inside my own mind.

At the end of the 10 days, once we could speak, I would come to learn that other’s motivations included:

• Getting over relationship breakups

• Seeking career clarity

• Processing grief

• Desire to better oneself

• Hoping for a general perspective shift to something more positive

• Tools for coping with the stresses of being a tech founder

• Getting out of a post-pandemic malaise

So the range of intent was broad. But why here? Why this specifically?

Whilst there are many forms of meditation out there, Vipassana has a long tradition that dates back to the Buddha around 2500 years ago. This is not a scholarly article on Buddhism, and I am by no means an expert, so I’m going to condense about 2500 years of background here!

The Buddha, meaning ‘the awakened/enlightened’, was born Siddhartha Gautama to a royal family in a region which is now part of Nepal. He renounced a life of comfort and riches and went off in search of answers. After many years of trying and failing, he eventually went to meditate under a Bodhi tree and is said to have sat for 49 days before becoming enlightened, at which point he understood the true origin of human suffering and how to get out of it. That happened at the age of 35, and he spent the remaining 45 years of his life teaching practices across Nepal and India to help people alleviate their own suffering. Vipassana, meaning ‘to see things as they truly are’, is said to be one of those core practices.

So Vipassana has about 2500 years of heritage, which I think is one factor that draws people in. Despite it’s ancient roots though, much of the core teaching feels more applicable now than ever before. I understood it as follows:

• We are all architects of our own suffering. Bad things happen, but it’s not the external thing that creates our suffering, but our internal reaction to it.

• There is an important mind<>body link here. When something bad happens in the external world, or we simply think about something, we have a physical reaction internally, and it’s that physical internal reaction that our mind is disturbed by.

• We’ve conditioned our minds to stay in a highly reactive state in which we crave certain things and are averse to others. We are unable to simply observe our internal world without passing judgment on it.

• The practice of Vipassana is a form of brain training. You are trying to rewire your brain’s circuitry to stop reacting to every stimulus and to become more equanimous.

At an intellectual level, all of that made a lot of sense to me. But what was it actually like in practice?

Well the actual practice of Vipassana sounds simple enough. You sit and ‘scan’ your body continuously from head to toe and back again, trying to sense any and all physical sensations going on. To begin with, the more obvious stuff becomes apparent e.g. pain, throbbing, itches etc.; but over time your mind tunes in to incredibly subtle things too - I recall spending a while focused on the temperature of my fingernails in one of the early meditations. The key with these sensations is to simply observe, to not react physically or mentally, or to think of this sensation as good or bad, but to simply know it is there and that it will eventually pass so not to get too attached to it. At times the practice felt frustrating - like trying to catch smoke with your hands - the harder you grasp the more it slips away from you. Other times it felt amazing - I found myself in deep states of concentration with what felt like a warm current of energy passing through me. Either way the intent was to remain equanimous.

Despite the simplicity and innocuous nature of the practice I would certainly describe it as one of the hardest and most brutal things I’ve ever done, and not for all of the reasons I thought it would be. I quickly got used to the silence, the 4am wake up calls, eating my last meal of the day at 11am. But what took me by surprise was:

The physical and mental pain, particularly during the ‘Adiktan’ sittings in the earlier days. These would typically start out nice and calmly, no pain, getting into a state of calm focus and thinking to myself, “I could sit here forever.” By 30 minutes the discomfort would often start to creep in. By 45 minutes there was outright pain and audible sighing, swallowing and signs of stress starting to spread through the room. With about 10 minutes to go every part of my being was screaming at me internally to move, to uncross my legs, to stretch out. I could feel the heat rising as I tried to cope with the pain and discomfort, and I would start to hear people crack around the room - limbs moving, shuffling on cushions - and just I was about to do the same, a chant would break the silence and signal 5 minutes left to go. I would make it out alive.

The extreme mood swings. Despite trying to remain equanimous, the 10 days was a real emotional rollercoaster for me. Any one day might include moments of bliss and clarity, moments of boredom and frustration so bad I wanted to scream, and moments that felt mental-breakdown adjacent. For a good number of people it all becomes too much at some point and they leave - an empty bed with a folded blanket, and an empty meditation cushion in the hall, serving as constant reminders of the potential to leave and be at home, in comfort within a matter of hours.

The bizarre physical experiences. I should say that everyone’s experience of Vipassana is personal and unique. I spoke to some people who had hallucinations; others who remembered long-forgotten memories; some whose experience remained fairly unremarkable and mundane - for me, it was weird physical stuff. On around night 3 or 4, I spent almost the entire night awake due to the copious amounts of saliva that my body was producing. Sorry for the graphic description, but I was drinking pints of it. There was a moment where I thought to myself ‘if I go to sleep I might drown on my own saliva.’ Thankfully I lived to tell the tale and my salivary glands seemed to go back to normal. Then, on around the 7th night, I had the weirdest experience of all - I woke up, only to find that I couldn’t move my legs. I could see legs. I knew they were my legs. But it seemed that the connection between brain and legs had been temporarily severed. Eventually I drifted back to sleep and awoke to normal bodily function.

Despite all of the hard, and downright weird parts of the experience, you may be encouraged to know that there were some profound and deep upsides to my experience too.

I felt like it enabled me to peak around the curtain at another way of being for my mind - one with less internal dialogue, less catastrophising, less anxiety. There was a real sense of ‘oh, so this is what your mind looks like when it’s not constantly bombarded.’ Early in the process, I would walk a lap of the outside area and feel my mind starting to head down all sorts of rabbit holes. By the end, I could walk several laps in a deep state of calm, with very little mental noise. You might call it flow. It’s the way I tend to feel when I go surfing. It was a real demonstration of just how much of what feel like the more stressful parts of life are simply created in my own mind.

It clarified some of the distortions of my conscious mind. I see it like this - our conscious mind is like a pair of glasses which largely determine how we see the world, and yet it’s sneakily convinced us that we don’t wear glasses at all - that we’re seeing things with perfect clarity. That sneaky little trick means that we give it the trust and the attention it craves; and like a parasite it seems to feed off that. The more attention we give it, the stronger it gets.

Throughout the experience, my conscious mind was getting more and more starved of attention, but at times it was still up to its old tricks - one of which was building stories about the people around me - ‘I bet he’s nice, he’s got a kind face. I bet he’s a bit of a ****. You can tell by his walk…’ Despite no talking, no interaction, and my best efforts, this story building was happening.

There was one slight fixation I developed - working out who Bjorn was. You see there are brief moments in the meditation hall when you are quietly called to the front and sit in front of the teacher for a moment of whispered question-and-response about how you’re getting on. One of these whispered interactions I overheard (but didn’t see because my eyes were closed) was with someone called Bjorn, who as the name suggests, had a thick Swedish accent. Over the coming days I made it my mission to figure out who Bjorn was and eventually narrowed in on a Swedish-looking target, with suitably Swedish mannerisms, who simply had to be Bjorn. I was looking forward to talking to my pal Bjorn at the end of the experience.

Come day 10 when the silence was broken, I went off to find Bjorn. Only it turns out Bjorn is actually a well-spoken Englishman called Tom. All of the preconceptions I’d developed and the stories my mind had told turned out to be wrong - not just about Bjorn, but about anyone else too. It was like holding up a mirror to some of the sillier parts of my mind.

Despite speaking to almost everyone, I never did find Bjorn.

It gave me a real appreciation of the small things. It’s something I strive for yet don’t always live up to, but with my brain in a calmer state I was able to feel a deep sense of presence and appreciation for even the smallest moment.

It gave me a sense of mental resilience. That might sound strange given the hard moments I described above; but a remarkable thing started to happen - once I stopped resisting the pain, realising that no matter how much I tried to block it out, it was still there; once I was able to stop thinking ‘ow, ow, ow, when will this stop?’, and start simply observing everything going on internally, then I found the sense of pain disappeared. I could still feel a sensation there, but there was no negative sentiment attached to it. Not every sitting, but there were some, where I sat at ease for an hour and felt like I could have sat for many more if needed. That journey with pain gave me a sense of having tapped into a deeper well of resilience than I previously knew existed.

And now, as I write this, I’ve been back in the real world for about 10 days, in which time I’ve been working, walking the dog, spending time with my wife, travelling to the Isle of Man for my mother-in-law’s birthday celebrations - the usual rhythms of life really. The main difference in terms of routine is that I’ve been starting the day slightly earlier with a 45 minute meditation. I’m also a bit more strict with myself (albeit not perfect) in terms of my phone usage - switched off at 8pm until the following morning, no phone in the bedroom etc.

Thus far I’ve managed to hold on to a slightly calmer mental state than before, noticing that there are certain things my mind would have previously reacted to in a certain way, which have provoked a more muted response. Where trains of thought have left the mental station, I’ve found myself better able to spot them, decide if they’re helpful or not, and then put a stop to them if the answer is no. My concentration has improved, with my mind less prone to seek distraction and more able to simply focus on the task at hand. And, after all those hours of changing my relationship with pain, I’ve found myself able to endure more and keep going during my regular gym classes. As for whether or not any of this lasts, we’ll just have to see.

A bell rings. 40 men start a slow, silent walk, heads down, making no eye contact, past a small building with a sign that reads ‘male cells’. Yard time is over. In the distance another bell can be heard, and 40 women living a parallel existence do the same. I acceptingly make my way towards a large building in the distance knowing that we’re about to enter an ‘Adiktan’ sitting. My mind is calm and quiet. I feel at ease. I’ve lost track of what day this is. I just have to remind myself that this blissful feeling will also pass.