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Ship It Week, day 1 retro

Sep 19, 20257 min read

1. Opening Circle

  • One of the most salient things for me in my lived experience right now is like “oh yeah, I cried during the opening circle”
  • It’s interesting that I very rare cry alone, and as soon as I realised we were going to go around in a circle and talk about how we’re arriving, I knew I’d cry and then spent a few minutes with a pounding heart trying to figure out how to formulate what I was going to say (whilst also trying to attend to what others were saying)

Why would you cry in front of strangers?

  • From one point of view, it’s surprising that I’d be more likely to cry in front of a group of mostly strangers, rather than alone. There’s something very interesting here, as it shows empirically something around like, idk, “more psychological safety in a group, more capacity to process emotions in a group, the ability to go deeper when you are seen by others”. Like, the depth was immediate, we didn’t have to warm up, it was just “oh I’m about to be the centre of attention in a few minutes? Ok, guess I’ll cry immediately”, lol

Not really strangers

  • I think the “strangers” thing isn’t quite right, because it’s not like this is a business conference and we all have our LinkedIn faces on or something. There’s a lot of shared context (Tpot, post-rationalism), and even if I don’t know say 85% of the people, there are a few people who I have spent a lot of time with and feel a lot of safety with (Simmo, Brent), and a few others who I haven’t spent loads of time with but have enough of their vibe to know that they are very good people (Rich, _, _) (redacting names b/c idk how people feel about privacy and stuff)

A few minutes of being totally present, held by a group

  • So actually, from another POV it makes total sense. When I’m alone, it’s easy to be lost in the hustle and bustle, I had travel logistics and Dad-in-hospital logistics and etc, and juggling work and etc. Vs now 20 people are looking at you, you’re the focal point, “what are you arriving with?“. Well, I just spent 2.5 weeks in the hospital with my estranged Dad, as the only person who visited him that entire time, 12+ hours in the hospital each day, helping him re-learn to walk. But the main pain is in how difficult I find him, how impossible true connection seems, how infuriating he is, etc etc. See 01. To be a boomer lol

How it felt to cry in front of a room full of people

  • It felt really sweet, actually.
  • I can totally imagine that pre-Kensho, this would have been mortifying. But I know that this is a safe group of kind people, that sharing what is really happening for you in that moment is truly the whole point, etc
  • And very sweet to get kindness from my friends afterwards, a few people saying they were touched by it, etc
  • Some cringe afterwards at like “oh no, how do I debrief from this, now I’m the guy who everyone will remember as The Crying Guy”, but it’s no big deal - went and played some guitar, then hung out with some friends, then bed time, then boom new day

2. Community

  • Ahhhhh it’s so so great to be here
  • It’s a lovely group, it’s so exciting after ~6 months of living with my mum in a small English village to be plugged back into a great group, to see that these people do exist in the world
  • And to see Rich and Nati who are let’s guess 40 and actually do have an extra depth of wisdom. Like, they’re not just older in years, they have the wisdom, they’ve been doing this whole-heartedly for years. It can feel like tpot is mostly made up of low-conscientiousness vibe-y 28 year olds so it’s really great to have the role models, these “elders”
  • Makes me think a lot about e.g. Fractal and intentionally being inter-generational. And the “living in a Non-Molochian world” stuff from here → It’s possible that community could obviously be the thing for me (2025-08-28). Like, the importance of cultivating a Non-Molochian corner of the world, carrying the torch, being a beacon of light

3. “Oh yeah, I have grown a bunch”

  • This is the most profound part so far really, and very difficult to capture in words. I’m having myriad experiences per day of like “holy shit yeah I can’t believe I just did x, social anxiety would have made that soooo much harder”. And not that I’m doing these insane huge things, just to be able to even e.g. do some stretching and stuff whilst talking to people, no worries about if it’s weird, just “I want to do x → I am now doing x”, very flow state-y
  • It’s easy to forget and to maybe even doubt that I’m doing much better these days, because I’ve lived with my mum for 6 months with gradually depleting energy, not much room for thriving etc
  • Vs plugging in here and it’s so apparent how much I’ve changed post-Kensho. Like “holy shit, I can cry in front of a big group and feel 0 embarrassment at all”. I can feel totally non-shy, I can notice feelings as they arise like “ooh, I’m feeling a little awkward right now, I don’t know what to do with my hands” and have that just be a fact, that my emotional schema of the world is still “ooh, some of these people seem cooler than me and intimidating”, and see that as a story, etc. First dart/second dart.
    • This is why I think the Kensho was akin to stream entry → I think I saw through the illusion of self, and although it didn’t drop away forever, I now just no longer take it seriously, so there’s no like “eeeee I’m so worried about embarrassing myself because you know, my Self is real and that will be so bad!”, it’s like “oh yeah no big deal”
    • Kinda like this Sasha tweet 👇

Interestingly, I’m still ~quiet (?)

  • It’s not that I’m socially anxious, but it’s true that I actually am happy to sit and be the kinda non-verbal one, maybe asking a bunch of questions and stuff, but I don’t typically want to enter a room and immediately be having a conversation or engaging people
  • There’s a slowness which is maybe the same thing as introversion
  • But also, I’ve already made some people laugh a few times and that has felt really rewarding and lovely
  • I think in the past I found Simmo difficult to be around because he’s so energetic and can take up a lot of the conversational space (he’s gotten much more skilled at the balance IMO), and I’d get into rumination about how he’s doing too much & how I should probably do more etc, vs now I’m happy to be this chill presence and engage when it feels alive
  • We had a great ~hour long conversation in the music room last night re: vajryana Buddhism and Brent thanked me afterwards for the great questions I was asking and how I helped the conversation go deeper, which felt great <3 I have some old model of like “you’re supposed to be interesting/big/charismatic”, and it’s great to get “food pellets from the universe” via being engaged, thoughtful, noticing your own confusion and curiosity, etc

4. What am I here to do?

Misc things

  • Mentioned Sasha Chapin so much already lol, he’s really the only poster who a bunch of things have really clicked into my brain. E.g. “that reminds of this tweet” or “that reminds me of this substack”, lol, lame

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