About 10 years ago, I set a goal to not have to get a job when I graduated from university 3 years later. My rough plan was to start a small software business that made me enough money to live on so I could do whatever I wanted. It took me another year to actually start working on that goal, but I achieved it!
I built Complice, an intentionality app that helps people set goals and work towards them each day even when what they need to do each day is very different. It’s based around the idea that regular inquiry into what you’re doing towards long-term goals makes a big difference in your ability to steer towards the futures you want.
After I hit ramen profitability, I grew the business a bit more, but it hit a plateau. While I never really decided to stop growing it, I don’t think it’s a coincidence that the growth stopped right around the threshold of wealth that I was used to as a kid growing up: definitely enough money for basic things and healthy food, but not like… extra. More concretely, about $50k in subscription revenue, with very little required work—the famous four-hour work week.
It’s hard to express how awesome this has been. I get to do weird illegible things like prototype a new cultural platform for humanity, without convincing anyone else that they’re worthwhile. I like to say that for something fairly highly rated, passive income is still underrated—at least for me. Some people feel the need to have external structure in their life in the form of a job, but not me. I like waking up every day and broadly doing what I feel like doing, or what seems to need doing based on my own personal assessment.» read the rest of this entry »
I had a concept that my 2021 would be called Always Already Dancing, and while that has been a background theme in various ways, there’s been a much more prominent theme, which is Catching my Breath.
The most overt element of this is that I began taking weekly days off, where I begin the day with nothing scheduled, no intentions, and no open browser tabs, and then I do whatever I feel like all day. I also aim to not add anything at the start of the day as a plan for later in the day, but to remain in improvisational flow, just doing what I’m doing right now.
But the underlying thread of catching my breath is one that’s woven through much of the last year on various scales, so here’s the story of my year of catching my breath, told in some semblance of chronological order of when certain elements arose, although many were happening in parallel throughout the year.
As I wrote in last year’s review, 2020: Free to Dance, my partner Sarah and I moved out of the culture incubator I’d been living in for 7.5 years in Waterloo, ON, and out to British Columbia on the west coast, where we’re working on creating a new culture incubator in Victoria, BC on Vancouver Island.
The need for a new culture incubator emerged not just out of us wanting to be in BC’s climate, but from some divergence in how we saw the incubation process needing to work. We’re still, as far as I know, basically on the same page about what the new collaborative cultural platform that we’re aiming for looks like when it works, but we’ve got a different idea of how to get there and how to operate in the meantime.» read the rest of this entry »
In my 2019 yearly review: Divided Brain Reconciled by Meaningful Sobbing, I experimented for the first time in a while with setting a theme for the upcoming year: Free to Dance. And lo, while I didn’t think about it that often, it’s proved remarkably relevant, in ways I couldn’t have anticipated.
The original concept of the phrase came in part from having just picked up Bruce Tift’s book Already Free: Buddhism Meets Psychotherapy on the Path of Liberation, which by early January I could tell would be a major book of my year. Another related dimension of it was something I realized in doing some of the emotional processing work last year, which was that parts of me sometimes still kind of think I’m trapped at school where I’m supposed to sit still at my desk, among other indignities.
The other main piece was observing at a couple of points that I sometimes seem to move through the world as if I’m dancing, and other times much more heavily. During an exercise at the Bio-Emotive retreat midsummer, we were asked to reflect on a question something like “how would I be if I were showing up most brilliantly/beautifully?” And what arose for me is something like “I think I’d always be dancing.”
So all of these layers mean that the social isolation of the pandemic didn’t put much of a specific damper on this life theme, even though I was hardly free to go to dance events (except some lovely outdoor bring-your-own-partner contact improv events that a friend hosted). I had been intending to travel the world a bit, to San Francisco, perhaps Austin, perhaps the UK, and none of those visits happened.
What did happen?» read the rest of this entry »
My recent yearly reviews have gotten very long & complex. For 2019, I’m just going to reflect on a few major learning arcs I went through.
The post is structured as an expansion of the six-word story in the tweet above (“divided brain reconciled by meaningful sobbing”) which I’m first going to do in paragraph form before elaborating one layer deeper:
Essentially, I came to understand that the major oscillation I’ve had in my mindset learning process over the past few years can be characterized as being due to my right hemisphere understanding things that my left hemisphere doesn’t, and not knowing how to relate the two perspectives coherently. That produced major changes but there were still some core fears that kept driving me back into the old perspective. I then did some intense work illuminating & transforming those emotional schemas, using techniques from the Bio-Emotive Framework and other systems, and I feel a lot more spacious now.
Back in February, I watched an interview of Iain McGilchrist talking about a new model of what’s going on with brain hemispheres. This is a topic that’s gone out of fashion since the misguided oversimplified models of the 1950s, so it took a psychiatrist being fascinated in his spare time for 2 decades, for someone to come up with an actually useful overall model (as opposed to just “well, these modules are in the left hemisphere, those modules are in the right.”).
The basic jist is a shift from asking “what do the hemispheres do?” to instead asking “how do they see the world? what kind of world is it, and what kind of relation do they have to that world?” This, not incidentally, is more of the sort of question a right hemisphere would tend to ask, as it orients in a naturally relational way vs the detached stance of the left hemisphere.» read the rest of this entry »
I’ve been experimenting with something new for my new year’s reflection: typing in the dark with my screen off, answering the question “What choices did I make last year?”
I’ve got over a hundred lines, each starting with “I chose”.
I think it’s worth reflecting on the impact of the choices as well, but I’ve started just by listing them. Maybe I’ll go back and try to think about the impact of some of these choices, but of course it’s very hard to actually run the counterfactuals, including what would have already needed to be different such that I would have made the other choice?
So far it’s been a very rich process. This article has two parts: first I’ll remark briefly on my experience doing this private reflection, and then I’ll share five choices that I made last year. The latter section represents my 2018 Yearly Review blog post, and also has some in-depth reflections on relationships and productivity.
Some periods of weeks have no notable choices in my memory, even though everyone is always making choices continuously. Other times, I’m very aware of a dozen choices I made on just one very intense day or weekend.
Some choices need to be made continuously & ongoingly, such as the choice to maintain a habit or to achieve something that takes a lot of planning or preparation
Some choices didn’t feel like choices at the time! This has a few variants:
Some choices were very historic/monumental: they really felt like they could have gone either way and my life is forever changed because of what I chose.
Other choices felt inevitable but there was still a moment of the choice becoming real. (eg when someone says “I do” at a wedding altar… by the time they’re there they’ve already chosen, and yet it’s still meaningful to enact it with that speech act)
In addition to the 5 year mark, this is also timely because I just heard from the instructor, Val, that after lots of evolution in how it was taught, this class has finally been fully replaced, by one called Presence.
The Againstness Training was an activity designed to practice the skill of de-escalating your internal stress systems, in the face of something scary you’re attempting to do.
I had a friend record a video of my training exercise, which has proven to be a very fruitful decision, as I’ve been able to reflect on that video as part of getting more context for where I am now. Here’s the video. If you haven’t seen it, it’s worth watching! If you have, I recommend you nonetheless watch the first 2 minutes or so as context for what I’m going to say, below:
It’s January 31st, 12018, as I type this. I told myself last night that I would either write a yearly review today, or not at all. It feels hard to figure out what to say about my past year. My life is rich and complex and wonderful and challenging and… hard to summarize.
Yet I feel like I don’t want to break my chain of yearly review blog posts quite yet. So here I am, writing… something. If I were to ask myself, “Aside from breaking the chain, why does this yearly review post feel important?” …the main answer is that there are things about my life that my blog readers don’t know, that might be valuable context for anyone who is following the story of my life.
This itself is a sort of strange experience. I know who some of the readers of my blog are—some friends, my housemates & other Upstart collaborators, and of course my parents—but I don’t know most of you. And yet even the people I know most closely still learn a lot about me from reading my blog, which suggests that if you’ve been reading most of my blog posts the past year or two, you also know a lot about me.
And if you haven’t? This is a challenge I face in all of my blog posts: to what extent can I assume that people will have read the previous ones? Or to what extent will they have remembered it anyway?
For instance, I didn’t remember until I re-read it just now that during last year’s review I said:
I’ll tell you if/how [using the Holocene calendar] affects my thinking during next year’s yearly review, after I’ve been using it for awhile.
So I guess I’ll do that. (For context, the Holocene calendar is like the one you’re used to, but starts 10,000 years earlier, making this my 12017 review instead of my 2017 review.) The short answer is that I don’t think it’s affected my thinking very much, and I found it to be not at all something worth creating extra confusion publicly, so it’s mostly a thing I’ve been using in my personal notes. I continue to enjoy it aesthetically though. I do think that when I first started using it it gave me a dramatically increased awareness of something like [where I am in history]. And now using “2017” to indicate the year feels like one of those graphs with the scale lopped off in a confusing way. “12017” of course also lops off most of the past, but it at least doesn’t lop off much history.
One thing I have often written about in my yearly review is what I learned that year. One of my biggest learnings of 12017 has already been thoroughly covered though, in Transcending Regrets, Problems, and Mistakes. That article tells the story of how I spent the year learning a very core skill: not imagining that the past should have gone differently, or even in some meaningful sense could have gone differently. Similarly, I could point you at Towards being purpose-driven without fighting myself to indicate a milestone partway through another major learning arc in the past year (disarming my internal conflicts) but I want to write about that in more detail in its own focused posts, so it doesn’t make sense to focus on it here. Nearly all of my blog posts in the past year have some sort of learning like that.
I notice, as I’m writing this, that I almost feel kind of defensive. As if I’m writing this post in an attempt to prove that it’s impossible for me to write an adequate yearly review.
Maybe I’m overcomplicating things, and a simple chronological approach would allow me to say whatever needs or wants to be said, on a month-by-month basis. I’m sure lots of things will yet be missed from this, but it seems better than nothing, and I don’t feel so defensive about it! 😀
The first major project that Benjamin and I did after he joined Complice was we ran two Goal-Crafting Intensives, which went awesomely. It was a great proof-of-concept for running events like these, and we’ve since planned and executed three more a year later, and are planning some other workshops in the future.
We then participated in » read the rest of this entry »
I wrote a post last year on two different kinds of expectations: anticipations and entitlements. I realized sometime later that there is a third, very important kind of expectation. I’ve spent a lot of good time trying to find a good name for them but haven’t, so I’m just calling them “the third kind of expectation”. On reflection, while this is unwieldy, it is an absolutely fantastic name by the sparkly pink purple ball thing criterion.
First, a recap on the other two kinds of expectations in my model: anticipations and entitlements. An anticipation is an expectation in the predictive sense: what you think will happen, whether implicitly or explicitly. An entitlement is what you think should happen, whether implicitly or explicitly. If your anticipation is broken, you feel surprised or confused. If your entitlement is broken, you feel indignant or outraged.
I made the claim in my previous article that entitlements are in general problematic, both because they create interpersonal problems and because they’re a kind of rationalization.
Since then, some people have pointed out to me that there’s an important role that entitlements play. Or more precisely, situations where an angry response may make sense. What if someone breaks a promise? Or oversteps a boundary? It’s widely believed that an experience of passionate intensity like anger is an appropriate response to having one’s boundaries violated.
I continue to think entitlements aren’t helpful, and that what you’re mostly looking for in these situations are more shaped like this third kind of expectation.
I was having a lot of challenge figuring out where to start this one. For some reason, the Object/Process/Meta structure I used the past three years doesn’t feel like it makes sense this year. Maybe because this year a lot of the object-level “stuff I did” was itself process- or meta-level.
The first thing I need to get out of the way is that as of last week, I’m using the Holocene calendar, which means that instead of writing my 2016 CE review, I’m writing my 12016 HE review. It’s the same year, but I’m experimenting with living in the thirteenth millennium because (4-6 years after) the birth of Christ is a weird start time for a bunch of reasons. Better is about 12,000 years ago, around the start of human civilization. There might be a slightly more accurate year, but the nice thing about just adding 10,000 years is that it means you don’t have to do any math to convert between CE and HE: just stick a 1 on the front or take it off. This in turn means I can use it in public-facing works and while it might be a little confusing, it’s still easily-understood. Here’s a great YouTube video on the subject. I’ll tell you if/how this affects my thinking during next year’s yearly review, after I’ve been using it for awhile.
Okay, 12016. » read the rest of this entry »
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 »
I'm Malcolm Ocean.
I'm developing scalable solutions to coordination between parts of people as well as between people. More about me.