How and why I take a weekly “day off”

Last year I started a new habit of taking a weekly “day off”. The two key things that make my day a “day off” are:

  1. no preplanned anything
  2. no browser tabs to start the day

I’ve kind of tried to keep those 2 elements alive during the day too though, meaning:

  1. I don’t schedule anything later in the day, during the day
  2. I try my best to decisively nuke browser tabs I’m not actively using

No preplanned anything

If some event is particularly juicy and only happens that day, I might put it on my 2nd calendar (more of an “fyi”) so that I know that the opportunity is there.

But I make it clear for people not to assume I’ll go.

Sometimes, a day or two before my day off, I imagine what I might do that day, but I still have to find out.

Saturday-me can delight in the present FEELING of how satisfying it might feel to spend my Sunday day off finishing an old backburner project… but it’s a fantasy, not a plan!

If anyone asks me “what are you doing on tomorrow/Sunday?” I just say “whatever I feel like doing!”

It’s simultaneously kinda scary & profoundly liberating to tell people I’m not available on a given day not because I’m busy but because my schedule is completely empty and NOBODY (not even me) is allowed to fill it.

» read the rest of this entry »

Fractal Home

I’ve just moved into a new home (just north of Victoria, BC), and it seemed like a good time to publish a piece of writing I drafted in January about the nature of Home.

In the terms of my previous blog post, it could be summarized as something like “Home is where you have non-naive meta-trust”.

Naturally, people really really want this sense of Home, although they may think it’s impossible, theoretically or just pragmatically. In general, most people don’t have environments where they have deep meta-trust, and don’t have a workable roadmap towards creating such environments. But it’s possible, given enough shared attention and an adequate toolkit, to co-create this sense of Home.

And, moreover, the process of a group consciously co-creating Home can itself produce the feeling of relief that being Home produces, [[in the meantime]], if everyone feels a sense that the group is doing its best to take into consideration the careabouts of each group member—before it has actually solved all the problems. This is a collective version of what Mark Lippmann calls the “Handledness is Already Success” principle.

When I use the word “need” or “want” or “careabout” or “desire” in this piece of writing, I’m pointing at, fundamentally, a cybernetic control system set point. What makes something a need, vs a want, might be essentially, as my friend Catherio put it: “if this goes unmet, I will make substantial changes to my life”. These careabouts include things on every level from psychological safety & self-actualization & meaning, to food & water & shelter… and probably stuff Maslow forget to mention!

I am Home to the extent that (and in the ways that)

  1. I can relax knowing that the systems around me aren’t going to subvert my needs & wants (whether malevolently or carelessly) and will in general support them.
  2. I feel, and am, empowered to make changes to the situation in order to care for my needs.

This applies to any context, not just to a house. In particular, it can also apply to a group of people or a relationship. So I’m not talking about “home” as contrasted with “work” and “third places” here.

This applies to all sorts of meta dimensions but it’s also very concrete:

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A Collaborative Self-Energizing Meta-Team Vision

Originally written October 19th, 2020 as a few tweetstorms—slight edits here. My vision has evolved since then, but this remains a beautiful piece of it and I’ve been linking lots of people to it in google doc form so I figured I might as well post it to my blog.

Wanting to write about the larger meta-vision I have that inspired me to make this move (to Sam—first green section below). Initially wrote this in response to Andy Matuschak’s response “Y’all, this attitude is rad”, but wanted it to be a top-level thread because it’s important and stands on its own.

Hey @SamHBarton, I’m checking out lifewrite.today and it’s reminding me of my app complice.co (eg “Today Page”) and I had a brief moment of “oh no” before “wait, there’s so much space for other explorations!” and anyway what I want to say is:

How can I help?

screenshot of LifeWrite landing page

Because I realized that the default scenario with something like this is that it doesn’t even really get off the ground, and that would be sad 😕

So like I’ve done with various other entrepreneurs (including Conor White-Sullivan!) would love to explore & help you realize your vision here 🚀

Also shoutout to Beeminder / Daniel Reeves for helping encourage this cooperative philosophy with eg the post Startups Not Eating Each Other Like Cannibalistic Dogs. They helped mentor me+Complice from the very outset, which evolved into mutual advising & mutually profitable app integrations.

Making this move, of saying “how can I help?” to a would-be competitor, is inspired for me in part by tapping into what for me is the answer to “what can I do that releases energy rather than requiring energy?” and finding the answer being something on the design/vision/strategy level that every company needs.

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Relationship Panarchy

“Relationship Panarchy” is a term that I coined to talk about a model of relationships, that can function both as a lens through which any relationship dynamic can be viewed (including retrospectively) or can function as an explicit intentional way-of-operating. Actually operating in accordance with this view is something that no humans I know are yet masters of, but there are an increasing number of us trying. So to some extent, at this phase it can function as a kind of placeholder, similar to how “Game B” is a placeholder for “whatever transcends and outcompetes the Game A cultural operating system that has been running the show for 10,000 years”. And, like Game B, we can say a few things about it even while it’s in the process of coming into view.

The one-sentence summary is “Relationship Panarchy is a model of relationships that’s like Relationship Anarchy, but instead of being individualist, it’s oriented to caring for the whole systems that support the relationships and people in them.”


So: there’s this concept “polyamory”. For some people, it tends to come with a bunch of structure implied, such as “primary partners” and terms like “metamour”. For others, it’s basically a synonym for “non-monogamy”.

“Non-monogamy” is able, by being a negation, to imply less structure, but it isn’t sufficiently general because:

  1. it doesn’t allow for Game B operating-system relationship configurations that read as monogamy on the old map because they involve two people being sexually exclusive
  2. it still over-emphasizes romantic relationships as primary, by negating them

One model that seems to be more open-ended is known as “Relationship Anarchy”. From Wikipedia:

Relationship anarchy (sometimes abbreviated RA) is the belief that relationships should not be bound by rules aside from what the people involved mutually agree upon. If a relationship anarchist has multiple intimate partners, it might be considered as a form of non-monogamy, but distinguishes itself by postulating that there need not be a formal distinction between sexual, romantic, or platonic relationships.

Relationship anarchists look at each relationship (romantic, platonic or otherwise) individually, as opposed to categorizing them according to societal norms such as ‘just friends’, ‘in a relationship’, or ‘in an open relationship’.

I really liked this idea for awhile, but eventually I realized that the imagery of anarchy as such evokes a rather individualist orientation to relationships, to a degree that from my perspective is not only undesirable but technically not even possible. Autonomy is important, and so is connectedness, and the two are not at odds but fundamentally made of each other. Each limit creates new freedoms and each freedom creates new limits.

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Dispel your justification-monkey with a “HWA!”

Justification—ie a normative explanation, as opposed to a causal one—is sometimes necessary. But, for many of us, it’s necessary much less often than we feel it is.

The reason we justify more often than we need to is that we live in fear of judgment, from years having to explain to authorities (parents, teachers, bosses, cops (for some people)) why things went differently than they “should have”. This skill is necessary to avoid punishment from those authorities.

We often offer justifications before they’re even asked for: “Wait I can explain—”

With friends, though, or in a healthy romantic partnership, or with people that we have a solid working relationship with, it is quite apparent that this flinch towards justification is actually in the way of being able to effectively work together. It is:

  • unhelpful for actually understanding what happened (since it’s a form of motivated cognition)
  • an obstacle to feeling safe with each other
  • a costly waste of time & attention

And yet we keep feeling the urge to justify. So what to do instead? How to re-route that habit in a way that builds trust within the relationships where justification isn’t required? How to indicate to our conversational partners that we aren’t demanding that they justify?

There are lots of ways to do this—here’s one. » read the rest of this entry »

How I Learned to Stop Hurrying and Fall In Love (with a project)

I’m flexing my blogging muscle again, for the first time in nearly 2 months. It feels a bit weird, and kinda nice. The break I took also feels both weird and nice.

There’s a trope or something about blogs where half of their posts are just the author apologizing for not posting more often. This isn’t going to be one of those—instead, my absence from this space is something that I want to reflect on, in a similar manner to my normal blog posts. How does it relate to my own growth? How does it relate to motivation? To metacognition?

This reflection ends up spanning 5 years and touching on a lot of what’s core to me (and what was core in the past). » read the rest of this entry »

5 Things I’ve Learned from Extensive Couchsurfing

Over the past few years, I’ve spent about 7 months staying with friends while traveling. Here’s what I’ve learned from the experience.

1. Offers can come from surprising places

One of the main ways that I’ve found people is just by posting to Facebook that I’m going to be in town and I’m looking for a place to stay. (I suspect this works better for me than other people, since I have a fairly engaged feed.) This is a nice approach, because it lets me cast a wide net without anyone really feeling like I’m putting pressure on them.

At any rate, apparently I still feel a bit weird about posting this or something. I’ve known for quite awhile I’d be traveling to the Bay Area again this August, and yet I still didn’t manage to get around to making a simple post until yesterday. I think it’s that issue again where not getting what you want feels immensely worse if you can’t pretend you didn’t want it.

Anyway, offers to stay, both on facebook and from people I’ve talked to in person, have often come from people I didn’t actually know very well at the time, which I wouldn’t have expected. Although of course I got to know them better via staying over, so we’re closer now 🙂

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A laptop employed as a nightlight

This post is kind of from two years ago. I got thinking about it again last night when I was reading Wait But Why’s The Cook and the Chef, an article describing how Elon Musk does what he does, which is a lot. The author, Tim Urban, is using an analogy of chefs as those who actually do something original and cooks who just follow recipes. He remarks that most people think that most people are chefs and then some chefs are just better than others… but that a better model is that most people are cooks (some better than others) and then the main difference between most people and Elon Musk isn’t quantitative (“he’s smarter”) but rather qualitative (“he does things differently”).

It’s like a bunch of typewriters looking at a computer and saying, “Man, that is one talented typewriter.”

Imagine a laptop.
What can you use it for?
That laptop can be used as a paperweight.
It is, in fact, better than some objects (such as a pen) at being a paperweight.
But that’s probably a waste of the laptop.
What else can you use it for?
It can also be used as a nightlight.
It has quite a lot of comparative advantage at being a nightlight—most objects don’t emit light, so a laptop works pretty well there.
However, it’s still a huge waste.
And, if you’re a human, not a computer, it feels terrible to be wasted: to not be used for your full range of capabilities.
» read the rest of this entry »

Announcing the Effectivity Habits Project

In 2014, instead of trying to change 50 things at once for New Years’, I decided to try a serial approach, changing one thing each week. I made 47 such attempts (took most of August off) and had 13 wins and a bunch of other good stuff come out of the not-wins.

This inspired my friend and collaborator Brienne Yudkowsky to do her own version of this for 2015. She came up with a number of changes that I really like, and so I’m going to merge most of her fork back into my branch. But with one key change: a focus on effectivity.

I’m deliberately calling this project “effectivity habits” rather than “productivity habits” because I want to imply a focus on achieving important results, not just on producing a lot of stuff. Productivity is a really key component of effectivity, but loses sight of the end result in its heads-down focus on the process of d. Which is fine! Process is important. But I also want to deliberately install some habits that will make me pay more attention to whether or not what I’m doing is truly moving towards the goal. Nate Soares, in the linked article, writes:

My advice, if you want to be effective, is always be solving the problem.

Note that he says “effective,” not “productive”.

My original Habit-a-week project was totally random. That was fun! Each week, I chose a new habit to install based on whatever felt most juicy. » read the rest of this entry »

Growing a Garden with a Broken Bodum

the corner of the room where the bodum fell. Framed by a wall on the left and a chest freezer on the right.

It didn’t occur to me to take the picture until after I cleaned up the broken glass.

This post isn’t about gardens or bodums. It’s about thinking and mindset.

Last July (~15 months ago) I had an interaction in my house’s laundry room, where I moved something on a shelf, which knocked off a bodum (aka french coffee press) which fell to the ground and shattered. I mentioned this to Jean (the likely purchaser/user of the bodum) that it had broken. But… the shelf was in a corner, with a chest freezer making it even more secluded, so the broken glass wasn’t a threat to anyone. So I decided I’d clean it up later.

Of course, as we know, later never comes.

So when it came time in August to leave for a four-month internship at Twitter in San Francisco, it still wasn’t done. I swore to Jean “I need to finish packing, but I’ll do it tomorrow morning before I go.” Not too surprisingly, I was packing basically all night. So morning came and I was running around and she said to me in my stress and frenzy, “Don’t worry; I’ll clean it up.” I was hugely relieved because I had felt an obligation to clean it.

Interlude: Malcolm in San Francisco / Berkeley, then home for Christmas

When I returned to the house in January of this year, I went downstairs to do laundry, and glanced in the corner. Lo and behold, a broken bodum remained. “Huh,” I thought.
» read the rest of this entry »

A portrait of Malcolm Ocean

I'm Malcolm Ocean.

I'm developing scalable solutions to coordination between parts of people as well as between people. More about me.

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