posttitle = 2023: Allowing Diligence titleClass =short len =24

2023: Allowing Diligence

My 2023 was unequivocally awesome.

It’s a testament to the ways in which having a few key things go right makes any other mistakes or problems or challenges feel navigable.

Themes & dual meanings

I started 2023 with a theme in mind, which was Allowing Diligence. Coincidentally, like my friend’s year theme “Play With Responsibility”, this has a dual meaning:

  1. allowing myself to have diligence
  2. having diligence about allowing

One of the things I had in mind when I oriented to allowing myself to have diligence was that I’d get more on top of my email inbox, which for the past few years has been more like a stream I’d dip into every couple of days to glance for possibly-relevant-and-actionable items, and a repository of things I might search for. I’ve had a few alerts for specific kinds of emails, including any replies to messages I’ve sent, but otherwise… ¯\_(ツ)_/¯ And last year for some reason I felt like it was a good time to get on top of stuff. I intended to be diligent, set up some new systems, have consistent routines or habits…

I failed at this. I’m as on top of my email as I was a year ago. And… I’m okay with that. Maybe at some point I’ll get inspired to rejigger my email system, but it doesn’t feel like something I want to make a point of doing.

Part of why I’m okay with my distant relationship to email was that I had the experience a few times of telling people about it and hearing them get hugely envious. Somehow I’m getting away with not checking my email. I feel it too, when I say it: a bit cheeky. High status, like Christopher Nolan, who famously does not have an email address (obviously somehow he has an assistant or something). Sometimes I drop balls, but on the whole this has been worth it for me in order to not be addicted to inbox zero, which has happened to me many times in the past. It’s compelling, but a to-do list that anybody can put stuff on is a distraction from proactive intentionality. Obviously there could be better solutions, but for now, this is mine. If you want to reach me, DM me on twitter or text.

Part of me is tempted to say that this conclusion was a win by the other meaning of Allowing Diligence: having diligence about allowing. But it’s not really the main point in that direction either! But I did perhaps get better last year at allowing the reality that I can fail at stuff.

I figured it would be appropriate to make this year’s post image using an AI image generator, since those really took off this year. This is an image I generated sometime in December, not for something but just as part of moodboarding & envisioning something about the vibe I want my life to have, and it’s apt for this post. Regarding images, you’ll see various photos below, many of which are contextualized by the adjacent paragraphs but some aren’t. They’re all basically in chrono order though. Think of it as a way I’m saving a few thousand words.

generated by DALL-E with the prompt 'a regal beam of light shining down onto a single eye of awareness, suspended in the air above waters that are tranquil in the middle and stormy further out'

The story of 2023, starting with the end of 2022

In my yearly review last year (2022: Deepening in a Different Direction) I noted how the editorializing process leaves out details for various reasons, and how that had historically included any of my struggles that I hadn’t figured out how to frame (read: rationalize) in a positive optimistic light. And before I can talk about what happened last year in anything resembling chronological order, I need to fill you in on something that happened in 2022 but which I left out of the blog post, that shaped the arc of my entire 2023:

Jess and I got engaged! Privately in October, then we told our family in December. So when I published my 2022 review, I still hadn’t told even my close friends, and I wasn’t about to spill the beans to the public internet! Our engagement wasn’t a slowly-reasoned mutual “so I guess we’re fiancé(e)s now”, but a bold “will you marry me?” from me to her—a proposal that came at a point when we seemed to have done all the requisite steps in our respective mating dances and we were starting to talk about our future together as if we were gonna get married… and, well, even though I didn’t have a ring and we actually were on a video call at the time, it just started to feel too wrong that we weren’t betrothed. So, after a minute of visibly grappling with something, I popped the question. The raw honesty of this move felt in line with how we want to live. The asymmetry of the proposal felt good. The symmetry of neither of us wearing an engagement ring also felt good (and Jess isn’t the type to wear a big jewel that’ll catch on stuff).

So my New Years Eve 2023 was spent in Australia not just with “her family” but “my future family”.

And then in January we were in San Francisco again. I started running some dinner parties, inspired by the example of my friends Priya and Andrew in Brooklyn NY, and by my friend Richard Bartlett’s apt-for-me cheeky challenge:

I already had a lot of connections in the Bay Area, but broadly kind of centered around the rationality community, which is no longer a center for my own meaning-making, and I wanted to have the chance to meet lots of new people including their friends. I also hosted and joined various gatherings oriented specifically around collective consciousness and so on.

In February, Jess and I went from being like “oh man we’ve gotta get on wedding venue planning!” on wednesday to checking out our top idea on saturday to putting a deposit on monday after double-checking the dates with our close family and friends. The ease with which we were able to orient and make a decision here (and at many other moments in the year) struck me as a sign that our bond was secure and not leaving out major elements. In past relationships (romantic and otherwise) these conversations had often been difficult, and we were paralyzed by indecision or false starts—a sign, in retrospect, of real conflicts or problems unacknowledged and likely unacknowledgeable-without-ending-the-relationship. We started looking for matching rings, getting excited about opal before learning that it doesn’t usually stand up to continuous wear for (eg) a wedding ring.

In March, I had a very transformative day where I did THIS meditation on the void multiple times. This resulted in a new depth of experience of fully occupying the stance of allowing, and how to handle disturbances to it. The new depth didn’t last more than a day or two, but I made a drawing and a write-up continue to inspire me: art is choosing what to breathe life into.

In April, I went to an event that we called the Coherence Retreat, inspired by the impact of the BioEmotive Retreat in 2019. I played a co-hosting role, in particular shaping the invite list to include a lot of the people I most respect in this domain. “Coherence” here referred to both group coherence and emotional coherence in the sense described by the Coherence Psychology Institute in eg Unlocking the Emotional Brain. This was a cool prototype of events serving many purposes including bringing together groups of people that have dense pockets but don’t all know each other, to look at big questions from many angles. And also to create a context that can help resolve conflicts among the people who do already know each other. I anticipate doing a lot more of it on various scales once I get a bit more settled. Two ideas I’m excited by are an Evolution of Consciousness Studies unconference, and an aspiring soulmages workshop-in-the-sense-of-a-large-room-with-lots-of-equipment-where-you-try-stuff.

In May, I went back to my home-or-at-least-permanent-address-and-location-of-my-stuff in Vancouver, the place where I caught my breath in 2021 with my friend Eric Chisholm. Earlier in the year, I’d started orienting to rebranding my 10yo intentionality app business, Complice, because I felt like one of the things that had me resisting growing it was that I really didn’t like the name I’d chosen back at the start. I spent much of the month on my own, head-down, working on the business rebrand. I finished it while I was there, though it took longer than anticipated because of some technical upgrades I tried to make at the same time that I eventually abandoned. Here’s the announcement: Complice has become Intend (that post is also on the substack connected with the new brand).

Also, while reunited with my stuff, I spent an afternoon in the sun in a park re-reading the diary I’d kept at age 13, which chronicled my desperate attempts to “get a girl” and have my first kiss. It was healing to see myself and hold myself and love myself, partially because of my new vantage point where I knew that the story was now working out so well (I shan’t say ending: this is just the beginning, in a way) but also partially just because I know how to honor and validate what perspectives feel like from the inside, in a way I didn’t even a few years ago, let alone at that age.

Cultural evolution project updates

In early June, on my way east from BC, I stopped by in Calgary to spend a few days with an old friend of mine—my oldest friendship that’s still active, by about 5 years. It was satisfying to play both with old jokes and also new explorations. I shared the Snake Cult of Consciousness article with him (coolest essay written in 2023 in my view) and it resonated with a bunch of stuff he’d been thinking about for awhile and we were able to do a lot of co-exploration into stuff about the evolution of culture and religion and so on. He’s been being a hermit for a while so it felt really good for him to get to plug his independent thinking into larger currents of questions that seem to me to be ones that humanity does not yet have good answers to.

Then I made my way to Waterloo for further meta-protocol jamming with the collaborative culture scene there that I’d been very intimately involved in from 2012-2020. I discovered that I’d been quoted in my friend Naryan’s new book Human Work, about bringing collaborative culture to workplaces. In fact, it turned out, I hadn’t been “quoted”, the ostensible reason for which is that the blog post he wanted to cite didn’t contain the exact phrase he was looking for, but I actually like it better that way—there’s no point in quoting anyone on this phrase since the whole point of the phrase is that it’s self-evident, not something you would take someone’s word for.

But being back in Waterloo was… interestingly uninteresting. I had been quite excited on a lot of levels to reconnect with Jean and the others and see where we could get in multiple weeks (compared to the one week I’d thus far spent back there since my 2020 departure). I was able to make a few new experimental trust-dancing moves, and it was interesting to see how they landed. But to a large degree, we seemed to mostly be falling into the same grooves as before. There was one conversation in particular where I watched a moment where if I’d been slightly more present I could have made a new move that would have at least informed me about whether this new move made any difference, but I missed my moment, had a typical-of-years-ago reaction, and it fell apart. This was frustrating. I didn’t learn as much as I’d hoped, on those levels. And they didn’t seem to have developed much at all since I’d left.

Then Jess arrived on the train from visiting her New York family, and we spent a few days in Toronto before reconnecting with the scene in Waterloo. The culture there puts a lot of emphasis on membranes and it felt really good to recohere my membrane with Jess and step into the context as a twosome, not “part of” the local group. It felt good to introduce Jess to these people who’d been such a huge part of my life. The main impression she got was of a sense of “it seems like they care a lot about you and are also pretty angry with you and feel pretty unheard and you feel angry with them and unheard by them.”

One of the last days Jess and I were in town, we had a 6h conversation with David, one of the core people in the ecosystem there, reflecting on a lot of dimensions of how the system operates, my relationship with Jean, and my frustrations at having trouble even coordinating spending time with them while I was in town. For context, Jean was and is at the center of the culture incubator project I was part of in Waterloo, and was my mentor and close friend and main-sensemaking-person for many years. I’ve learned a lot from her, both from what she taught me and from watching where she gets stuck. And in May I’d written her a letter with the subject line: “I want you in my life”, which was an attempt to create a new context for a new phase of our relationship; it included a wedding invitation.

And talking to David that day, I got a sense that… perhaps Jean and I don’t really have a shared sense of how we’d like to be in each others’ lives. We have a lot of shared history, we’re still clearly part of the same big evolution-of-culture metaproject, but it’s not clear what kinds of interactions we would mutually want to have with each other that we aren’t having. I would like certain kinds of reconciliation & repair, in large part just because I think it would be a meaningful experience for me to understand myself and the world and what I was missing from her perspective. I have pieces of writing that remain unpublished because I’d like to sync up with her about aspects of them first, but she’s been fairly clear (mostly via not replying, but in one case explicitly) that she’s not interested in syncing up about them.

I’m really not sure where any of that goes from here. Mostly I’m moving on with my life, but it feels unsatisfying. Every few months I have an experience where I feel like I’m understanding Jean’s perspective better, but it’s hard to corroborate it.

Summer with family 

Jess and I flew from Ontario to Nova Scotia in early July, to spend time with my family. I had the delightful experience of being able to return (for the first time in ages) to a family camp I’d been to every year from when I was a few months old til I was 18 (the one I wrote this song about). As I’ve started orienting more towards having my own family, I’ve gotten more interested in family trees, so I started mapping out my various relatives there. My great-grandfather on the maternal line brought his kids and niblings (gender neutral term for nieces/nephews) and so over the course of the week there were 38 people at this camp (out of a thousand or so) who were in some way part of my family. One evening I noted that I was playing (a card game, and on a playground) with:

  • a first cousin (my grandparents’ other grandkid)
  • a second cousin (my great-grandparents’ other great-grandkid)
  • a third cousin (my great-great-grandparents’ other great-great-grandkid)
  • …oh and a zeroth cousin (my parents’ other kid, also known as “my sister”)

I found myself thinking that knowing one’s third cousins was probably very common back before people used to move around so much, but now it’s a rare treasure afforded primarily by this camp that keeps people coming back year-after-year. The camp is nominally Christian but has diminished in its spirituality over the years, and I’m a little worried about how it’ll navigate the coming decades. I want my kids to get to play with their fourth cousins (not that they’ll care to keep track any more than I did at their age!) I want Christianity itself to evolve to steward the moral revolution we need for our time, which seems to me to be different from the one that was needed two millennia ago.

The week after that, in August, my little sister got married, which, in addition to being a great chance for me to meet friends and in-laws on her husband’s side, was also a great chance for some of my extended family members (who wouldn’t be traveling to mine+Jess’s November wedding in the Bay Area) to meet Jess in the context of her being imminently part of the family.

More travel, more allowing?

In September I took a trip to Europe, primarily to give the keynote at the LessWrong Community Weekend. I realized that for the same price, I could have them fly me through London first, so I could go to an Alexander Technique weekend with Peter Nobes, the awareness-and-aliveness oriented teacher that I’d heard so much about from my friends Michael Ashcroft and Lulie Tanett. It felt like a good move for the Allowing part of my year theme. But like the insight in March, and other experiences in April and May that I didn’t even mention, while I tasted some new possibilities, it didn’t really add to my capacity to live differently on a day-to-day basis. And my theme wasn’t “taste Allowing”, it was to diligently practice allowing. But it kept being weirdly hard to practice… something that I would only end up doing when I’d exhausted the other options.

This showed up again in preparing my keynote. I did a bit of prep, honing in on the main points I wanted to make, but despite my intent I did not allow myself to diligently rehearse it so I wouldn’t have to wing it, nor did I diligently allow it to just be what it was. When I arrived I talked to an organizer about it and he said something like “it doesn’t have to be polished, as long as you have a clear thing to say and you’re intellectually rigorous and honest.” Inspired by this, I planned my intro and whipped up two dozen minimalist slides, some of which were very simple: a short question, or the word “obviousness” in size 100 font. The talk ended up going really well, and I enjoyed the format of improvising most of it to the key of my slides and the rhythm of questions from the audience. I’ve been meaning to edit the video to post it for months and finally am doing so so that I can link it here—nothing like a real showtime to make something happen! I edited it with Descript, and after some technical glitches it is finally actually live:

The weekend itself was kind of unexpectedly satisfying. I’d been so tickled by the prospect of getting flown in to give the keynote that I forgot to have a clear intention or expectation for what I wanted from the rest of the event. But a major theme ended up emerging spontaneously as a result of an icebreaker game of “Anybody Else?” on the first evening: one person stepped into the middle and said “I used to be religious but now I’m an atheist… anybody else?” and got lots of fellow atheists stepping in, then after they cleared I stepped in and said “I’m kind of… trying to… rederive God? Anybody else?” …I’ve played this game before and noticed that it’s important to be specific enough to matter but general enough that other people can actually resonate with what you’re saying. And this struck the right note of confused earnestness that I got a few people who joined me, then in the dinner line she asked me about rederiving God and we struck up an amazing conversation that folded in another couple people and in some sense lasted about 4 days (although we did sleep at least a little). That’s all I want to say here but if you want to check out the concept then I recommend listening to my friend Romeo talking with our friend Aneesh and then maybe also with me.

Anyway, then I missed my return flight, due to a half-dozen things that each added 10 minutes, and as a result I had to spend too much time in airports (plus more money). But a couple days later I landed on the continent of Turtle Island, in New York. My plan was just to connect with some twitter friends with a cool campus project in Brooklyn for a few days before returning to Canada, but then Jess surprised me by showing up, and we ended up taking a few days to go visit her mom’s family (and meet her mom for the first time) who live upstate. We went with her mom to see the Chapel of Sacred Mirrors, Alex & Allison Grey’s immersive visionary art exhibit.

In October we headed back to San Francisco and went into the final arc of preparing for our wedding. In addition to a bunch of logistical coordination, there was also a bunch of final work to do on our outfits: Jess painted a design on the back of her outer dress and I… learned how to sew pants. After several prototypes, I successfully converted a one piece thobe (middle-eastern robe/dress) into a top and pants, and the pants fit SO WELL because they were measured for my exact shape and where I like to wear them. So they were fancy as all get out and also perfect for dancing.

November brought our wedding and thus also our family to town, from Australia, New York, Ontario, Quebec, and Nova Scotia—plus our friends from many more places still. And many of them brought a small jar of ocean water, which we combined during our ceremony. We’re working on some writing about how we designed our wedding to incorporate traditions while being fresh and spiritually honest, which we’ll probably publish on both her blog and mine in the coming months. One little piece I’ll note now is that we made a point of making exactly one vow: to get married—not adding on additional vows about specifically how we want to treat each other or whatever.

“Ocean” has been my last name for a decade, but hasn’t thus far been my legal name. (People will sometimes ask if it’s my “real” name and I say yes and remind them that the government is not an authority on what’s real!) I’ve been meaning to change it, but hadn’t gotten around to it. Now it’s my family name. And after the experience with the cousins at camp in the summer, where it felt more true to introduce myself as “I’m a [grandmother’s maiden name]” because that was the family name that people were most familiar with (in part because my 2nd cousin once removed has been the Treasurer the last few years). Now I feel like I can be all of my family names, while also having a new name for my immediate family.

I could give a long rant about how we tried to get the county clerk to recognize that my name was already legally “Ocean” despite my lack of “legal ID” as such. This certainly would have worked a century ago, probably would have worked 30 years ago, might have worked 10 years ago, but doesn’t work now. It used to be understood that individuals could use whatever names they want, as long as they aren’t committing fraud, and it was the government’s legal responsibility to document this fact; now the government’s relationship to names is more like they own them, which is a bit messed up. But I’ll leave the rest of the ranting to this site on “common law names” (nothing to do with “common law marriage”) if you want the rabbit hole.

Anyway, the wedding was lovely. We did a 3-day retreat in the woods (with cabins) and I cannot understate the extent to which something like this is way better than just having everybody scattered for a few days when they fly in from out of town. It gave our families a lot of chances to connect and really get to know each other, not just exchange handshakes and pleasantries and selfies. Now they’re talking without us even in the loop, and planning visits in NS & Aus! And it was also really satisfying for so many of my friends to now have context on my family, and vice versa. It really felt like the event cultivated a strong web of people who will support us. In a way, not unlike a conference where people won’t show up unless you have talks but the real magic happens in the hallway in breaks, the days of the retreat had a magic of its own that bonded us in ways the ceremony never could have on its own.

New stability allows more deep change

As I’ve been mentioning, one of my big aims over the last few years has been to grow my business, Intend, in part to make more money for having a family. Midway through the year, I realized that I really didn’t know how to do it, so I switched my goal to “learn how to grow my business”. Then I realized while getting some marketing/analytics/SEO advice from a friend that maybe it’s possible that the work required to grow it isn’t even something I want to do. So I reframed my goal to “figure out if there’s a way to grow the business that I actually want to do”. I’ve had trouble giving up on it because despite my failures over the years it just feels so obvious that there must be something I could do to improve the bottom line. But I haven’t known what! My friend pointed out that answering the “what” question is actually most of the work.

Around the time I got married, I had the awkward realization that I was also sort of pressuring myself to grow the business because I was sort of assuming it was the only/best way to make more money, and that I needed to make more money in order to be… loved? Oops. Well, now that I’m married, the love thing is relaxing enough for me to be able to look at the logic here and be more conscious about the whole thing.

Even if Jess loves me for richer and poorer, there’s a real need for more financial flows in our family. And maybe the way to do it will turn out to be Intend after all. I don’t know. What I do know is that I hadn’t been taking my own advice: a common refrain that if you’re having trouble doing something, allow yourself the possibility of not doing it, so that you feel truly free to do both. Okay, we could be broke, or I could put a lot of financial burden on Jess… I don’t like those plans, but at least they aren’t unthinkable anymore, confusing me about reality. Or… I could make money some other way, or multiple ways! That has some draw—I have various other things I want to be exploring, including what I’m calling mating dance consulting: helping people navigate their choices around how and how deep to get into relationship with a partner. And as one move, I’ve set up a system now where people can directly book a paid session for that or various other offerings described on this page: Talk To Me.

And maybe I’ll explore something much more ambitious. Part of me feels like I could be done with being a solopreneur and ready to start a big project (build an alternative to the “web browser”?) that would require hiring people. Does that mean raising money? Big questions! No answers yet.

Fortunately for me and for its users, Intend mostly runs itself, so aside from bugfixes and replying to supportmail, I don’t have to spend much time or attention to have it continue. So it’s not going anywhere, whatever I end up devoting my central attention to.

Original Spin and deeper allowing

Relatedly, the other main thing that happened in the last months of 2023 was a major deepening into Allowing as a practice. As intended! But not how I expected.

My friend Michael Smith was visiting for a few weeks, and one day we started feeling into deeper layers of freedom, and started joking about how it would be funny if we were able to come up with a new viral memetic antivirus that would be able to liberate people from oppressive meta-memes… and well, good thing we joked about the outcomes we wanted, because despite moving on from that as an explicit aim, about 15 minutes later we stumbled upon a new insight that was absurdly obvious and self-evident once pointed out, but somehow we hadn’t noticed it yet despite years of investigating very related topics around memetics, selfness, coercion, gaslighting, and so on. And it immediately started giving us clarity and relief in relation to our own suffering too!

We’ve coined a name for the confusion we’re unwinding—”Original Spin”—and we’re in the process of iterating, often in public, on how to articulate it. But even at this early phase, just from some 1-on-1s and this unedited thinking-out-loud video, it’s already given a few other people meaningful insight as well. It feels satisfying to have a new distinct output of my work in illegible cultural evolution research over the past few years.

For the purposes of this yearly review, I’ll just tell one story of how it’s helping me deepen into the sense of allowing. A couple hours after we recorded the video I linked above, I was on a call with a friend, and reflected to him that I’d been making a delicious practice of slowing down, single-tasking (or even sometimes zero-tasking) and so on, and that that had been feeling really good—although, I reflected, it hadn’t been going as well as I’d hoped. And I noticed Original Spin at work, trying to convert my pain at having not been as present as I’d hoped during that time… into shame about not having done it right. I’ve been practicing releasing shame and shoulds for over a decade, but now I had new clarity that the pain I was calling a shame wasn’t fake, even if the shame itself was, in a sense. That pain was my pain, and I wanted to honor it and hold it. And when I did that, everything brightened and I felt profoundly spacious and way more clearly in touch with my own desire to continue that practice. It feels in some ways like a more embodied version of the NNTD insight I had in 2020, unwinding a similar double-bind as thinking that rejects other thinking, but in relation to my basic choice-making system.

So: I have an increasingly clear sense of a pathway towards stabilizing this mode of being that’s been eluding me since 2017 when I wrote “Towards being purpose-driven without fighting myself”. It often requires slowing down—a lot—because I can’t do it consistently in what I usually consider “real-time”. Like slowing down a piece of music to practice it, until it gets into muscle memory. And I’ve still clearly got other layers that need some love in order to be willing to do this slowing down (fear of death? fear of choice? subtle attachment stuff?) Whatever it is, I’m here to love it.

What 2024 might hold

I’m settling into living in San Francisco and feeling into what I want to do here in terms of scene-building. I’ve got a lot of potential projects but the most important thing is to approach them from a place of groundedness… rather than the bewildered flailing that has characterized much more of my activity over the past decade than I realized.

Jess and I got married hoping to have kids “near mode”, and while we haven’t started trying for kids, one of the other things I started allowing in 2023 was the possibility of becoming a father in 2024. I’m really excited.

I’m loosely feeling like maybe 2024’s theme will be “Abundant Love”, which touches on:

  • creating financial abundance for my family, while maintaining the precious time abundance that has allowed so much play and healing into my life
  • cultivating the sense of love in my heart that makes the slowing down feel delicious rather than boring or anxiety-inducing
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About Malcolm

Constantly consciously expanding the boundaries of thoughtspace and actionspace. Creator of Intend, a system for improvisationally & creatively staying in touch with what's most important to you, and taking action towards it.

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