The Unreasonable Art of Living
The Unreasonable Art of Living
#110 -Five Regrets Of The Dying
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#110 -Five Regrets Of The Dying

No, dark chocolate didn't make it in the top 5

This companion piece to this week’s episode. The podcast is the full, unedited, and raw version; this is just the rundown of what I talked about.

You can listen to this episode on Spotify, and Apple Podcasts for audio only.


#110 - Five Regrets Of The Dying

This one is just me again, no guest, no notes, recorded while agents were running in the background because I am deep in building our virtual world at the moment. It came out of a few conversations last week, and a podcast by Dr Zach Bush that had been sitting with me, and it turned into the most direct episode I have done in a while, so here is the rundown.

Where this came from. During an interview with a potential member last week I ended up recommending Bronnie Ware’s book, The Top Five Regrets of the Dying, which she wrote after years in palliative care sitting with people in their final days. I have talked about it on this podcast before, and it keeps coming back because the pattern in it matches something Justin and I now see constantly in conversations with members, which is that people who have maximised the Dwarf mode, the achieving, the money, the career, the titles, arrive at a point where they look at all of it and feel like an empty shell. There is nothing wrong with any of those things, and money in particular is a beautiful vehicle, but chasing them is a race with no finish line, and the wall at the end of it is always the same wall.

I wish I had the courage to live a life true to myself, not the life others expected of me. This is the first regret and the one I hear most often, and it shows up in language before it shows up in decisions. Listen for should, shouldn’t, and supposed to, and then follow the thought down to its root, and you will find it always leads somewhere outside you, some external reason, some X, Y or Z you inherited rather than chose. The heart does not work that way, because it does not know why, it just knows, and living true to yourself mostly means trusting that inner knowing when you cannot yet justify it.

Why so many of us cannot hear that knowing anymore. Zach Bush worked in chemotherapy research and then in hospice care, and he says the most remarkable part of that work was witnessing what happens as people die, including the roughly ten percent who had near-death experiences and came back reporting the same thing, that for a glimpse they saw everything was perfect, all of it, the ups and the downs, exactly as it was meant to be. I know that lands badly for some people, when there is war and torture and maniacs in power, and I am not going to argue the point or do the inquiry for you, because it is yours to sit with, and I am also not interested in the naive version where we ignore violence rather than standing clearly against it. What I take from him is the other half of his argument, that the body is the most powerful antenna nature ever made, capable of receiving far more than we credit it for, and that we have spent a century getting more abstracted and disconnected from it, until overthinking became the civilisational sickness and anxiety became the baseline in most Western countries.

I wish I hadn’t worked so hard. In that same interview the person described an exercise where she imagined how she would want to be remembered, and what came out had nothing to do with money, job, title, or anything she had accumulated; it was whether people would remember her as someone happy and curious who loved life and expressed herself fully. Being useful matters, making things matter, working matters, and still the thing people reach for at the end is whether they were a source of joy and laughter and connection for the people around them.


If you recognised yourself in this piece, you are in good company. Almost nobody looks back and wishes they had achieved more. They wish they had used their real, honest voice, kept their people close, and stopped postponing living a life true to themselves.

Eleven Dunbar is a private community of founders, builders, artists and dreamers doing something about all three. Find your voice, find your people, create the impossible. The community is capped at 150.

Members meet weekly to create alongside each other, and across a season there are visiting artists, shared projects, small group conversations, and people who notice when you go quiet.

The community is capped at 150.

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I wish I had the courage to express my feelings. This is exactly what we mean when we say we help people find their voice, because knowing who you are is only half of it, the other half is being able to say what you feel instead of swallowing it. Some cultures do this naturally and Western ones have made it either shameful or academic, which is its own way of avoiding it. My favourite question here, especially for men, is when was the last time you cried, and the answer is often that they cannot remember. There are spiritual books that will tell you to detach from feeling, that sadness and anger are not real and not needed, and I think that is spiritual bypassing dressed up as wisdom, because we came here in a body that can feel fear and grief and joy, and it makes no sense at all to be given that and then refuse to use it.

I wish I had stayed in touch with my friends. I am 36 and I am ridiculously lucky here, with friends I have known for more than 25 years who I still see several times a year, every summer without fail, and it is only because we have all kept investing the time. Call your mum, call your dad if you are lucky enough to still have them, because my dad is 81 and my mum is somewhere in her seventies, and I get a small jolt of happiness every time I pick up the phone and see mama or papa on the screen, and I love that I can sit with my mum and talk about deep things, and that the last conversation with my dad was him asking whether I believe in souls. By any financial measure I am a poor artist at the moment, and I do not feel poor in the slightest, because the abundance around me is in people and freedom and what I get to do with my days, and I would not swap it for anything.

I wish that I had let myself be happier. The word doing the work here is let, because happiness turns out to be something we withhold permission for rather than something we lack. Most suffering starts the moment we begin negotiating with reality instead of noticing the beauty that is available every ordinary day, and gratitude is the fastest way back. Leading with love does not mean being naive or permitting harm, because love has clarity in it and can be firm, and my own read is that only confused people harm others, which is worth holding with compassion rather than contempt, since nobody arrives in the world confused, it accumulates.

The people who see what you cannot see in yourself. Talking with our member Chad today reminded me why community matters so much for all of this, because someone who knows you can tell you that your eyes light up and your voice lifts when you talk about one thing, and go flat and calculated and cold when you talk about another, and you would never catch that yourself. That is the whole reason we exist, to help each other remember what the unbound excitement actually feels like and then follow it, which takes real courage because the world is not set up for it, and which is also the most beautiful path available to a person.

Play is how the universe operates. My friend Max Freiler and his partner Alissia have opened a health centre in Switzerland called Lunitas, a third space with co-working, workshops, ice bathing, meditation, and a playful wrestling class that he told me was the best thing there, which surprised him. What people are actually starving for is connection and play, and they will almost never name it, so you have to invite them in for something else and let them discover it, and I do not just mean board games, I mean play as creativity, as love, as learning, as experimentation, as walking through a forest.

A dark chocolate review, finally. Zotter, 82 percent from Peru, a gift from Alexandra. It smelled like Christmas chocolate to me, then plum on the tongue, then something sour underneath, and when I turned the wrapper over it said Christmas spices, plum, and sour cherry, which is the first time in the history of this segment that my palate and the label have agreed on anything. It is butter smooth and it goes straight in at number two behind the Zotter 80/20, which remains my favourite chocolate on earth.

The invitation. Do the thing the regrets are pointing at, today, while it is cheap. Call your mum and dad if they are still here, call a sibling, call a friend you have not spoken to in too long, tell your partner you love them, and then give yourself a hug and say it to yourself as well.


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