Malcolm Ocean on Rationality, Goals, Self-Awareness & Motivation as a Self-Employed Entrepreneur

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That's joincrowdhealth.com, promo code boundless. Mandatory disclaimer: CrowdHealth is not health insurance. It is a totally different way of paying for healthcare. Terms and conditions may apply. Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life.

Today I'm talking with Malcolm Ocean. He's a fellow wanderer of The Pathless Path and is, as is often the case, hard to describe, much like myself. He runs a software company, Complice, which helps people turn big goals into day-to-day reality. We're going to dive into that and go deeper into what do we mean about goals and all that and tying it to our day-to-day experience. More broadly, though, I think from my vantage point, Malcolm appears to be incredibly curious just about how we make things happen and not just things, things we actually want to do, things that are easy to do for us and how we do that at the individual and group level. Welcome to the podcast, Malcolm.

[03:48] Malcolm Ocean: Thanks. It's great to be here.

[03:50] Paul: Question I wanted to— Yeah. Question I wanted to dive into first was what's the first goal you remember setting for yourself? Hmm. Yeah.

[04:06] Malcolm Ocean: The first like really explicit goal that I set that was like, this is a goal was, um, in 2012, I decided I was going to record an album of original music. And I spent the year doing that. And I had a, I used, um, Zig Ziglar's kind of goal setting process for that, which I turned into, um, which is part of the inspiration for Complice. Um, but I'm trying to think about like, you know, even earlier, like I'm like, okay, I think maybe when I was a kid, I had a goal to learn how to do a backflip on a trampoline, which I succeeded at. Um, and then there's always, you know, those kind of implicit goals that you don't really set for yourself, but like, you know, they're kind of there. It's like, okay, I'm doing karate.

And then I'm like, obviously I want to get a black belt, but that's not really my goal in a sense. It's just sort of like, there I am in the context of karate. Everyone's trying to get a black belt. There I am in the context of school and everybody's trying to get good grades and, you know, stuff like that. So it's, um, stuff like that a bit too. I mean, I think I was pretty self-directed, but it was often a bit more spontaneous.

Like I just like made a little video game because I wanted to and stuff like that.

[05:07] Paul: Yeah, it seems like something that really interests you is about that. Like, how do we actually get to our goals? Are they given to us by society or the systems we're a part of? And how do we find the things we actually want to do? It's, it's sort of something I mean, on my own path being self-employed, it's kind of hard to figure that out at first. How have you come to want to increasingly think about that problem?

[05:38] Malcolm Ocean: Yeah. Well, the first thing I'll say is that like the, the way that I think about goals, um, the, for the workshops that, that we run, the, uh, goal crafting intensives, we came up with this articulation of what a goal is, um, which is a recognizable and desired state in the future, uh, that causes you to act in the present so as to realize that future. And so, it doesn't need to have a number. It doesn't need to have a, you know, a state of completion where you're definitely done forever. Like, it could be like you want to maintain that state ongoingly. But the point is it is in the future because you can't— if you're trying to change the present, you have a whole different kind of problem.

And it's something that you know and you're orienting towards. Because it's meaningful to you and it matters to you. And so, yeah, so with that in mind, it's like figuring out what do I actually want? I mean, that is a huge part of the puzzle. And one thing that I encourage people to do is to try— if you feel like most of your goals currently come from the outside and they're like about other people's ideas and recognition and stuff like that, then I have this suggestion, which is to do something that you want to do and like don't tell anybody about it for 3 years. Like just pick a tiny, it could be a very tiny thing, you know, like it could be going to the woods and, you know, arranging some sticks in a way that you like or something, but you don't show it to anybody and you don't tell anybody about it for like a long time.

And so it's like, By setting yourself that constraint, you have to come up with something that like you just want to do for you. Um, again, really doesn't have to be a big thing. Could just take an afternoon, like, you know, but I think there is something valuable like, and that even just doing small things like that helps you hone your taste. Um, and ultimately, you know, it's not that like social regard is irrelevant to the process of goal setting. I mean, I, I, I think there's a lot of ways in which our sense of who we are you know, comes from other, other people and how we interact with them. And that's okay.

Um, I would say for myself, like part of how I knew that I wanted to pursue having a lifestyle that was, um, not just working a job, but being able to, you know, run this company and do my own thing. Like part of how that was, part of how that came clear for me is that like in high school, I was reading a bunch of the, the OG lifestyle design bloggers, you know, Leo Babautov's Zen Habits. And, um, Steve Pavlina. Anyway, some of the other folks, you know, the original kind of bloggers. I forget what actually was Steve Pavlina's work thing was, but I was reading a bunch of people who were like, you know, making money from blogging or from a little software thing that they had. And, and that gave me the sense that like, that was a thing someone that was a thing you could do, which I think most people don't have as much of a sense of that being real.

And that's part of what, you know, I imagine your podcast is trying to do is like convey the stories of people who are living alternative lifestyles, essentially. And so it starts to, in some ways, make it less alternative. It starts to make it be a thing. You know, you can be a type of guy if you want. And so there's still space to be further unconventional. But like, if we can make it, if we can have more role models for living a lifestyle that's, uh, more self-directed.

I think that's really, really powerful.

[09:21] Paul: Yeah, I had a similar experience, I think, from 2014 to 2016-17 with podcasts. It was just people in my ear explaining things I had never imagined before. So it's these new paths, new models, new ideas of how to show up in the world that was like, oh, I can do these things. But I think the interesting thing you're talking about is sort of practicing action or sort of just taking the first step to agency or a little more ownership. Like, I don't think we can get to this state of like 100% we're controlling every action, right? We— but shifting it even 1% can have pretty profound effects.

Do you have an example of something you did that you didn't tell people for a few years?

[10:10] Malcolm Ocean: Oh, yeah. I mean, I guess this, I don't know if this was, I don't know if this was how I got it. I think this was like, I've always been pretty down to do my own thing, even when nobody was, um, even when nobody was telling me what, like telling me about it, or I didn't know anybody else who was doing it. Like, I think for me, it was, this wasn't ever quite my bottleneck. The suggestion to like, you know, go out in the woods or whatever came in response to a friend of mine who was saying like, I don't know if I've ever done anything not for social approval. And I was like, wow, well, yeah, how about you just try this?

Don't tell me about it either.

[10:44] Paul: This suggests—

[10:44] Malcolm Ocean: I don't want to know if you—

[10:46] Paul: yeah, yeah.

[10:46] Malcolm Ocean: So I don't actually know if this advice worked because, you know, the, the friend, the friend didn't tell me, right?

[10:51] Paul: Um, so I have told people one thing that does appear to work. I'll just throw it out there in the mix. I've had a lot of people tell me similarly, they've never taken a walk without a destination. So this is a very— Oh yeah.

[11:06] Malcolm Ocean: Oh yeah, yeah, yeah. That's—

[11:08] Paul: this is a very simple one you can do is just go for a walk, but just start taking random turns. And even if you're not random, like, I don't know, it doesn't even matter where you stand on the free will debate. I think it's almost this mindset of like pretending you at least have some control and taking random turns.

[11:27] Malcolm Ocean: Yeah. I mean, I would say there's a sense in which like Yeah, like, like, I don't know, the free will debate seems not a useful level of abstraction for a lot of this stuff, but it's like, like, obviously in some sense people are going around making choices and you can like refine your, your taste and your capacity to choose by doing it. And yeah, so definitely that's, I almost mentioned it myself in some ways, something about going for a walk and just exploring, you know. And I'm actually, I've got some upcoming travel, like I'm going to be in Europe and I have the first couple of weeks I'm going to be hanging out with friends in Portugal and that's kind of planned out. But then literally the extent to which I have my, my next 2 weeks planned is a train and Europe. Like, I don't have anything more specified than that.

I have a hazy sense of like, I want to see some really old architecture, like, like so old that there just isn't any of it in North America because I haven't really had the chance to see that before. But like, that's gonna be, I think, uh, an edge for me of just like really following my own whims. Um, yeah. And finding out what I want and being opportunistic and being like, oh, I wanna spend an extra day in this city cuz this thing is really cool or whatever. Yeah.

[12:44] Paul: This is—

[12:44] Malcolm Ocean: but you can just do it in your own backyard. Just like go in your backyard and just wander around.

[12:48] Paul: Like, yeah. This has been a common thing I've seen a lot of people on unconventional paths say is they sort of have some practice of practicing these like wandering things in their life, whether it be their work, travel, personal life, but having the sense that, oh, I need to practice this stepping into the unknown because that is going to provide me the learnings or the wisdom about what to do next. Yeah, and it's rather unintuitive to do this until you're on such a path. Is this something you've learned to embrace the longer you've been self-employed?

[13:33] Malcolm Ocean: That's a good question.

[13:34] Paul: Um, and maybe it might be worth backtracking and just sort of explain when you became self-employed and what that initial leap was like.

[13:45] Malcolm Ocean: Yeah, so I, I think I've been technically self-employed for my entire adult life. Um, but I, the first half of that was more kind of like a friend and I in high school started a web design business and we didn't really have very many clients at all and definitely had very, very few in, you know, um, when we, when we went off to university for the first few years. And, but then when I, when I was about halfway through my undergrad degree, I, I sort of thought about it. And I was like, I don't want to have to get a job when I graduate, like, that just seems bad. I don't want that. I want to be able to, you know, wake up and do what I feel like.

And so I set a goal in essence of having some sort of passive income project that would allow me to not have to get a job when I graduated. And, and I had no idea what that was going to be when I first decided that I was going to do that. I was just like, I'm going to figure this out. And, and so I started brainstorming ideas and so forth. And what I, what I ultimately came up with was this goal setting system based on this paper notebook that Seth Godin made out of Zig Ziglar's system. And yeah, so I made this kind of, yeah, digital thing inspired by that.

And indeed, by the time I graduated, I didn't have to get a job. Now, I wasn't actually making enough money from the app when I graduated to not have to work. But I was somehow having made a, you know, kind of productivity app or whatever, caused people to want to hire me one-on-one to just like coach them or whatever. And so without any particular training or credentials, I mean, I, I'd gone to some workshops and stuff and I knew some things and I read lots of books and tried lots of experiments myself, but I found myself in the position where I was, um, I was able to take on a role of helping people sort through their stuff. And so I was making, you know, this much money from the app and this much money from the coaching.

And then, um, over the following year, I scaled up the money I was making from from the app to the point where I now, I now still do a bit of coaching, but I don't like have to do it. Um, and, um, yeah. And so I've, I've never had a full-time indefinite job, if you see what I mean. Like I've had full-time internships, um, a handful of those, and I've had like indefinite kind of ongoing part-time or contract stuff. But, um, I've never just like had a job that was like by default going to be my job until I quit. Yeah.

And, and that's, that's so much how I want to live. Like, in so many ways, it's just like the feeling of, I wake up and I do whatever I feel like. And it's like, at this point, even if I were to have a job, I would want it to feel like that. I would want it to be, I wake up. And in the context of having this job, what do I feel like doing? And I would want to have a job where what I feel like doing serves the job, like where it, you know, satisfies my employer or whatever.

[17:09] Paul: Yeah, it's, it's funny. I worked 10 years before I became self-employed. So I sort of had to unlearn things. I had sort of taught myself the lesson that I couldn't really do the things I want to do, because work is something you have to do for other people in order to get the paycheck. And I think so many people learn this lesson. Did you have role models growing up that had done this differently, or did you just decide like that model wasn't for you?

[17:41] Malcolm Ocean: Right. Yeah. I mean, I guess I kind of come from a family of entrepreneurs, like on various scales. The main, like, if I sort of just trace out my family, like one or two branches away, the main person that like, I don't think ran a business is like my grandmother, but I mean, she helped my grandfather with the TV repair business that he had at one point. So, you know, that doesn't really count. And then I'm like, yep, those aunts and uncles have a business.

That uncle has a business. That aunt, no, she's a nurse, you know. Um, like, but like, it's all, you know, almost all of my family has, even if they also worked full-time jobs, which sometimes they did, they were like also at time at other times running companies or, you know, doing various ventures. So, um, like none of, none of them had the kind of, um, like lifestyle I have where the software runs itself and I am sort of, you know, like, like most of my time is spent staring at the nature of collective intelligence, like not working on Complice. Software or anything like that. Like that's, that's what I want to do with my time is look at how does collective wisdom work in small groups and how do we scale it up?

Um, and so yeah, but I would say, I would say like in some ways I had a lot of inspiration, but it was funny. Like my dad didn't really understand the business for years. You know, he would ask me, he would say things like, oh, so your business is successful. Like, uh, have you thought of having some employees?

[19:11] Paul: And I'm like, oh, this is so funny. Yeah. Yeah.

[19:13] Malcolm Ocean: I'm like, dad, that's not the point. Like, I don't need employees. Employees would just be more work. Like, and finally I conveyed it to him where I was like, so I've got this software, you see. I mean, he understands software. He was programming on punch cards back in the day, but like, um, but you know, plugging that into business was a whole other thing.

I was like, I've got this software. And when I first started with, you know, with Complice, I was emailing people every day to ask them like what they were doing toward their goals like that, you know, before I even wrote any code, that's what I was doing. Doing. And, um, and now the software, and that took me, you know, an hour per week per customer. And now I have, you know, 100 customers at the time or whatever it was. And so like, that would be 2.5 employees to like send these emails every week to these 100 customers.

But instead the software does it automatically. And he goes, oh, and I guess it doesn't, I guess the software never phones in sick. And I was like, yeah, okay, you get it. You're picking it up. Like why, you know, by leveraging software, it's like, I don't need employees to be making a bunch happen.

[20:23] Paul: Well, that having employees is sort of this metric of success of that's how you prove you're growing, you're getting bigger, you're more successful. It's funny. I was freelancing when I first started. Quitting my job and that's what a lot of older relatives would ask me. Are you going to hire employees? Do you want to build a company?

Are you going to get an office? It's like all these things would stress me out and add costs. I do not want to do this in the short term. And then just building a digital business is just really hard to explain to people because we sort of look at work as, semi-performance. It's like putting on a certain piece of clothing, going to an office, performing the ritual of doing that. And when you take that away, people are like, what are you doing?

I mean, somebody yesterday said to me, Paul, well, Paul doesn't really have a job. He doesn't work. And I just kind of laughed these things off at this point. But, and it's funny because to me, like the upsides of working this way are so large. It's kind of crazy that more people don't want to shift in this direction.

[21:36] Malcolm Ocean: Yeah. I mean, some people need more structure, like just in terms of how, like, you know, they, they want to not be making strategic decisions, I guess. Like, um, and, and I've had to come to terms with that. Like, it's, you know, it's, it's maybe not for everybody and that's fine, but I think there are a lot of people who would like it a lot. And, um, Yeah.

[21:58] Paul: You've said that utopia is when everyone just does what they feel like doing and the situation is such that everyone doing what they feel like results in everyone's needs getting met. Where does this vision come from and what are you doing to kind of shift things in that direction?

[22:17] Malcolm Ocean: Well, it's so related to what we've just been talking about, right? Like my image of waking up in the context of a job and doing what I you know, doing what I feel like, but having that serve whatever organization is hiring me such that they, you know, are empowered to, you know, pay me and support me and all of that. It's, you know, that's, that's very much, you know, a small-scale instance of this kind of, um, utopian quality. And, um, and I take utopia very seriously, um, but it's also like actually iterating towards it is a very tough puzzle, right? Um, where did that come from? Yeah, um, something like— I mean, there's been a lot of talk in our circles on Twitter about, um, like non-coercion as a, um, as a thing.

And, and that's a little, a little weird, you know, because it's framed as a negation. Um, but flipping it around and saying, you know, doing what you want, um Then the puzzle just becomes, well, how do you get really good at wanting? Right? Like, you know, how do you get really good at being plugged into, you know, what will actually satisfy you? Like, you know, like I think pretty much everybody's had the experience of craving a snack and eating the snack and it's not that tasty and you're not even paying that much attention while you're eating it. And then you're like, after, why did I do that?

Or like, you know, it's 4:00 AM and you're like, I just spent the last 4 hours browsing some weird subreddits, you know, and I didn't, that wasn't even satisfying. Like, it's not like I was having fun and slacking off from work. Like, I wasn't even having fun.

Like, and so, you know, the skill of finding out what actually deeply nourishes you, you know, like if you're gonna play video games, what are the video games that you will love, that you will like think back on so fondly of like, wow, that was so, so much fun to, you know, build that Factorio base with my friends or to, you know, go through that whole story adventure arc of this thing or to like get really good at the skills of this thing versus like, you know, some video game where you're just like, wow, I just sunk 100 hours into that and I, I might as well have been working for, or I might as well have been working a menial job for all it felt meaningful. Like, you know, it had, it had feedback loops that were compelling at the time, right? Like that's why I played it, you know, cause it gave me some feeling of like, ah, I can do this stuff. But like, I, it was not interesting.

It was not satisfying. Right. Like, and so, um, where am I going with that? Yeah. So like cultivating the capacity, first of all, to just like feel what serves you, like what, what, what in fact is deeply satisfying and nourishing to oneself. And then also developing one's capacity to look outwards and, um, and love and empathize and, um, and see how you can make the world a better place, either for, for individuals or by, you know, uh, creating some, some art or some business or, you know, some offering to the world that, you know, is, is better.

And then the third thing is like, it's not just about, you know, empathizing, but it's about actually being able to see other people's perspectives. And, um, well, it's a few things. It's like being able to see beyond the assumptions that you might be making where, um, like, you know, people were assuming productivity apps had to look a certain way and had to involve lots of organizing big lists of stuff that you have to do. And I kind of saw beyond that assumption and created a, an app that looks like a to-do list app, but has no backlog. There just isn't one. You can't backlog anything in it.

If you don't do something today, it goes on the list of things you thought you'd do yesterday. And now you have a new day. And you can go grab that stuff, but it's not building up. It's not, you know, it's not there to be wrangled. So I'm really trying to get to the core of the thing here, right? This sense of utopia is when everybody just does what they want and the situation is such this results in everybody getting their needs met.

I don't want to overly reify the concept of needs here either, but it's like, um, well, it's like everybody does what they want and everybody's satisfied with how that plays out, right? Like people are finding the work that is meaningful and satisfying and like, um, yeah, and maybe it's more helpful. Maybe it's helpful to talk about how this feels on a small scale.

[26:47] Paul: Yeah. Um, I think an example for me, is what we think we want, right? I went through this. What I thought I want was a prestigious job and impressive credentials. The experience of actually doing that over time was not ultimately fulfilling, but it actually took this very deep awareness and constant reflection to understand that. And then, I think the challenge in doing this is that we're just constantly learning and like just wrong about things, right?

So what I thought I wanted was to become a freelance consultant, but then about 15 months into self-employment, I sort of realized the thing I kept coming back to was writing without any sort of incentive or thing. And I'm like, oh, this might be what I want to keep doing. So then I sort of made a commitment and elevated that in my attention. I kept doing more of it. And then I've sort of just made decisions around making sure that that impulse doesn't get destroyed. So it's not even like, even for me, like I'm not aiming, I didn't aim when I published my book to become an Amazon number one bestseller, New York Times author.

Those things ultimately don't matter to me. But the thing I want to keep doing is writing. So it's something I need to keep paying attention to. And I'm also working with the assumption that it could be like that could stop being true at some point. So it sort of requires this reflective practice. Yeah.

And that's the hard thing is our desires and interests and what actually is fulfilling over a long stretch of time. Changes. Yeah.

[28:42] Malcolm Ocean: Yeah. And so there's something about developing your own internal compass rather than, I don't know, it's subtle and it's hard to talk about. But like I'm thinking about, I've sometimes quipped that like if you think, if you think Twitter inherently incentivizes sort of like outrage or something, then you're confused about the nature of incentives. Like, um, likes and retweets aren't inherently meaningful or valuable or rewarding. Um, you know, if you get enough retweets, then, you know, you can plausibly make some money based on just the fact that you now have a bunch of attention that you kind of get to steer a little bit. But it's pretty hard to actually use that, like, well.

Like, it's, you know, like, There's a reason that people are linking, you know, proverbially linking to their SoundClouds in the, you know, replies of a really viral tweet. Because like mostly you don't actually make money from SoundCloud and people are like using the attention to get people to check out a little bit of their art rather than trying to like actually sell something, which mostly you can't actually do in the replies of the tweet. People try. I mean, it's a thing that shows up. You know, I've seen people selling these like galaxy wall lights or whatever that are all the rage these days. Days.

But like, yeah, so it's like, you know, Twitter only incentivizes outrage if you— if among people who don't understand that likes aren't inherently meaningful, like they don't— like if you don't want to deal with a bunch of people being outraged on your, on your Twitter timeline or on in your replies, then you are not incentivized to do outrageous things like Because it's just like what you actually want does not match on to that. Um, and so it's like similarly, you know, what the incentives are for, for different situations, it's like they become a lot more refined once you really understand what you want. Um, because you realize that the things that sort of seem like the incentives are not actually what's driving you.

[30:52] Paul: How has that changed for you over time? Like, what is your process look like of getting in touch with what you really want over short stretches of time and longer stretches of time?

[31:06] Malcolm Ocean: Yeah, I guess there's a few things like, like one is I sometimes, I sometimes refactor my goals and what that consists of is making a list of things that are on a level kind of below, below actually all of my goals. There's sort of smaller things that I seem to want to do something about. Like basically I ask myself, what are the things that I'm trying to make happen right now? And I, you know, at any given time I might have like 20 or 30 of those or something like that.

[31:37] Paul: Um, do you have an example of one of those?

[31:40] Malcolm Ocean: Yeah. Like I might, you know, I might be a thing of like, oh, I want to, um, you know, I want to make the number of Complice customers go up. Yeah. Right. It's like a thing, a thing. Um, but on a totally different level, it might be like, oh, I want to like, you know, finish making my desk nice.

Because it still needs a few more components or something like that. Um, or it might be, yeah. And anyway, and then I would sort of, I would look at all those and I'd look at my goals and I would say, how do the, like, how does my intuitive sense of all the things I'm trying to cause to happen, like map onto these, these goals that I've set? Or have they come kind of out of alignment and I've sort of got this big goal, but it's not actually in touch with what I feel like I want. But other times it's like the big goal is actually feels really clear and I've been doing a bunch of stuff that's nebulously related but isn't actually moving that forward. Like I set a goal to learn, learn essentially, well, there's a, there's a therapy modality called coherence therapy and they have a related coaching modality called called Coherence Coaching.

And the fundamental principles of all of it are the same. And I had a goal to learn that really deeply, but I ended up tracking a bunch of stuff under the goal that wasn't really actually moving me towards that. And when I looked at it, it was like, yeah, I still care about that. Like, I want to achieve that, not just, you know, doing my own therapeutic healing process, which I was sort of tracking a bit under this goal. But like, no amount of doing that is going to cause me to like grok this technique. And so on, even though it overall does help.

And so, so that's then a thing of like, yeah, I still want this deeper thing, but, but I'm not really moving towards it. But I recently, you know, had a, a bit of a shift where what I thought I was doing with my life and where, where I was and all of that has kind of Yeah, all come uprooted earlier this year. And when I realized that I didn't want to be in the marriage that, that I was in. And, and so, in the wake of that, it's like I noticed there were all of these things that I actually wanted that I sort of that I didn't want in the context of that relationship because of the nature of the constraints of that relationship. But that once I took a step back, it was like, oh, where do I want to live? Maybe I want to go back to San Francisco where I, you know, was for many years.

Like, and how would I go about making that happen? Um, you know, I just, I spent a bunch of years traveling there and I have a ton of friends. That could be actually where I want to live. And like watching that arise now that the constraints had fallen away. And it's like, similarly, you know, like I imagine this occurs for lots of the kinds of people that you're working with is like, you know, when they leave their job, they suddenly realize, wait, you know, I don't actually want to live in this city. Or I actually, I don't, I don't care that much about having a car now that I'm not commuting.

And I'd rather just like have a bike or, you know, other things kind of cascade as a result of, you know, it's like you have one piece of clarity and then it actually begets more clarity.

[34:52] Paul: Yeah, it's interesting. We sort of, I think we sort of assume the things around us are the things we want. So if we're starting with that assumption, if we're in a sort of life path that is very predictable, we are gonna start tricking ourselves into thinking that's what we actually want. And like, people will say things to me, like I could never not own a home. I need a home base, right? So I've been semi-nomadic for 3 or 4 years and I don't have a strong reaction in the other direction because what I've realized is that I had untested beliefs about what I wanted before.

I thought I needed a home base too. And then I went nomadic and I realized, oh, I'm still kind of pretty happy, if not happier doing this, which means I was totally wrong previously.

[35:56] Malcolm Ocean: Right. Yeah.

[35:57] Paul: But I've sort of tested this different approach and revealed these hidden preferences. And I think, yeah, that, that is probably a big opportunity for people figuring out what they want is They kind of asking themselves, what are the hidden preferences that my current life circumstances can't reveal?

[36:20] Malcolm Ocean: Hmm.

[36:22] Paul: Yeah.

[36:22] Malcolm Ocean: And like, what are the assumptions? Like, I think about this a lot in the context of design where people kind of, they, they locally have a sense of what they want. They're like, oh, I don't like this font. Or I, this app is too slow. Right. Like they, they kind of, kind of minor local improvements, but, um, But, but so few people can, can see like, no, this app is paradigmatically confused.

Or like the whole basic interaction pattern of this design, you know, this design constraint of like how this app is, is made is like, is like backwards, you know? And so it's like people, people aren't able to access a sense of what they want. That's sort of beyond like one step away from what they currently are seeing. It's like, you know, oh geez, it would be nice if, you know, Uh, whatever, like, yeah, I'm not thinking of good examples right now, but yeah. Um, and that's one thing that I've been cultivating in the arena of design. Like I have this short series on YouTube, um, uh, of videos, probably record another one today about my new headphones, um, or earbuds that is, uh, the series is called What If It Were Good Though.

And basically it's like when I get a product that I hate, I just do a rant about like why it's awful. And then I try to just like blank slate, like what does this thing actually want to be? What would make it be actually good? And try to like really stretch the boundaries of my thinking to point at, um, something that, that's not just marginal improvements, but it's like a whole different fundamental paradigm. Like what problems is this really trying to solve? Can we approach it in a totally different way?

Like, you know, Yeah, stuff like that. And so it's like, similarly with your life, I think you can kind of, it's possible to sort of like really set aside the assumptions and be like, well, why do I want a home base? You know, what is that about? Can I go deeper? Can I go deeper? Um, and, um, and, um, I guess another thing is maybe like, what is the best version of not having a home base, for instance?

Or what's the best version of You know, if I assume that I'm going to be traveling for the next few months, how would that go best? Even before I've actually decided that that's what I'm going to do. It's like, can I sketch out the best possible version of that world? And I think people could benefit a lot from doing a lot more like imagining of what they want. I think me too, honestly. Like, I don't think I have flexed my imagination muscle nearly as much as I could.

[38:51] Paul: Yeah, it's, it's a hard thing to do. And it, it's an interesting time in the sense that like the internet provides an abundance of information and this can be good for generating new ideas, but it's also very easy to generate ideas against things. Right. And I think this is sort of tangentially related to something you wrote about in your essay, Towardsness and Awayness. Like towardsness, you're sort of aiming at something and it can be defined, but awayness is sort of unconstrained.

[39:26] Malcolm Ocean: And yeah, you can, you can go away in any direction.

[39:29] Paul: Yeah. And this will probably— this might confuse people the way I'm going to flip this and sort of say a tangential thing. But similarly, you can sort of be against something. But by doing that, you're being very specific and you're basically dismissing all potential possibility. So, Martin, I mean, Martin Guerrier writes about this in The Revolt of the Public. Like, people are often like, people are often not for anything politically these days.

That is a very common, like, failure mode is like, I am a Democrat because I hate the Republicans. I am a conservative because I hate liberals. Right. But they're not inherently for anything because the exploration of finding what you're for is unconstrained and infinite in possibilities.

[40:26] Malcolm Ocean: And overwhelming and scary.

[40:27] Paul: Yeah, it— yeah.

[40:29] Malcolm Ocean: And so there's some policies, but the policies are mostly sort of locally trying to solve some acute pain.

[40:34] Paul: Yeah. Yeah, yeah.

[40:36] Malcolm Ocean: I like to say I, you know, I basically resonate with everybody, like almost no matter what, what writing I read that's, you know, political or activist or whatever else, left-wing, right-wing, reactionary, conservative, you know, ultra-progressive. I basically agree with everybody's complaints.

[41:01] Paul: Yeah.

[41:03] Malcolm Ocean: On all sides, every direction.

[41:04] Paul: Because they're defined and specific.

[41:08] Malcolm Ocean: Right. But I also think that everybody's proposed solutions are complete shit.

[41:12] Paul: Right.

[41:13] Malcolm Ocean: Like, you know, it's like, are the, you know, are the Trumpers or whatever, you know, right about like ways in which the, you know, mainstream whatever has gotten out of touch with what— absolutely. For sure. You know. Are the progressives right that like, you know, certain rights are being ignored in certain ways? Like, absolutely. Sure.

Are the libertarians right that like, really, we should not be like making so many things into laws? Like, absolutely. Sure. Are the, you know, people who are talking about communism or whatever, like, right in terms of like, like, you know, we need to really like think about our social contract and like design systems, you know, like the utopian I was Utopia was talking about, the design systems where everybody's needs are getting met by what everybody's doing. Like, absolutely. Do any of them have the slightest clue about how to actually organize things so that even their own thing gets satisfied, let alone everybody else's?

Not at all.

[42:08] Paul: Um, well, it's what you said. It's awareness can't aim. Yeah, you can't aim at anything. You're just against.

[42:16] Malcolm Ocean: Well, and the other issue is like part of, part of what happens is people are like, I have this problem, so I need to solve it. And the solution they propose would create problems for a bunch of other people. And then those people would fight back. And so you get these grrr, grrr, grrr, grrr, grrr, grrr. Whereas if you can find a win-win, then now people aren't fighting your solution because it's also their solution.

[42:44] Paul: Yeah.

[42:44] Malcolm Ocean: And that's kind of the only way to actually have sustainable politics. Well, and then is to be finding win-wins.

[42:51] Paul: Yeah. And I want to tie this back to like I can tie everything back to self-employment or unconventional paths. But I think when you're, when you're on your own path, your solutions look stupid too, right? You're sort of like, okay, this other path can't work for me and I'm going to take an unconventional path and then I'm going to follow this thing that looks silly or stupid in the short term, but you're sort of aiming at your intuition. I think you have this deep sense that there's this future state that can be found. And I have some sort of connection to myself that tells me this is possible.

And I think that that's what makes, like, often what turns out to be bold solutions, even like politically or economically, the most interesting. It often starts with this deep connection to intuition. And I think this is something you're super interested in, and which is how do you scale that to the group level, which nobody ever talks about. Like, I used to do organizational change in big organizations, and it's basically just the study of individual incentives. Um, but nobody ever says, how do we do a goal at the group level?

[44:12] Malcolm Ocean: Yeah. Right. Yeah. And, and so the, the individual is a great, a great case study. Um, partially because you've got higher bandwidth in some ways inside your own brain than you do between people. Um, there's pros and cons to that.

Um, partially because it's all right there, like, you know, and, and there's sort of a, in some sense, a pretty locally, a pretty local choice-making agent who can kind of like assess all of the stuff and go, hmm, how do I, how am I going to relate to this? Um, but, but also because as an individual, like it's right there in the name, you are not dividable. Um, if you can't get along with yourself, there's no way to like agree to disagree and one of you moves to, you know, the East Coast. And the other stays on the West Coast. Like, you are you. You gotta, you gotta learn how to get along with yourself.

Um, and so that provides a really useful case study in, in a lot of this stuff. Um, but then, but then, yeah, it doesn't, doesn't sort of scale up directly. But just speaking about the, like, internal case study, it's like, um, you know, you might find that, like, you have some internal tension about something you want to do. You know, oh, part of me wants to, like, Let's take one of this, pick one that's like directly alive for me right now. Part of me wants to take my, you know, I have a bunch of coaching calls scheduled for tomorrow, which is my last day here in SF. And part of me wants to take those coaching calls and, you know, satisfy my sense of my, you know, relationship with my clients and like, you know, make the money that I get from those calls because if I don't take the calls, I'm not getting paid.

You know, and, you know, I have those various things that I want. Also, part of me wants to not have my last day here be full of calls. Like, I want to be able to, like, spend more time with my friends here. What do I do about that? Like, can I find a way to kind of honor both of those voices and figure out what it is on net that I want? And clearly, I can't directly satisfy both.

Like, I can't both take the calls and not take the calls. But like, if I go up some levels, and this connects to some of the perceptual control theory stuff I was talking about on Johnny's podcast that you mentioned listening to, it's like, if I go up some levels, can I find a place where it is clear how I wanna resolve that tension? And there's no right answers there. There's no objective right answers. Talking about this situation from the outside, which I'm actually doing right now, even though it's me, like I'm not actually inside the conflict feeling into what it is that I most deeply want here. I'm just talking about it as a hypothetical that happens to be my, like, you know, hypothetical that I'm live working with, but it's still, I'm still looking at it over here.

I'm not like opening up into it. From the outside, there's no right answer. There's no, oh, well, you should definitely cancel the calls and spend more time in person, or, oh no, you should definitely uphold the Nope. There's just what do I actually want given everything? And so then the puzzle when you start to look at groups and so on is can you find a what do we actually want given everything that's not a compromise and it's not a one person sort of deferring to another kind of going, oh, well, I guess we can just do your thing. They're kind of like, But it's like the situation is able to surface enough of the relevant factors and for people to feel enough in sync that they're actually— everybody is like, oh yeah, that's clearly the thing to do.

Right. And you can see this with tiny decisions, right? It's like, you know, you're out with some people and you're like, oh, we should go for dinner. And someone's like, how about Mexican? And somebody else is like, nah, Mexican gives me gas. Like, I can't handle it.

Okay, cool. You know, what about like, you know, what about we go to this, you know, sandwich shop instead? And somebody else is like, no, no, they don't serve, you know, gluten-free sandwiches. So I can't go there. And it's like, okay, what do we want? How about Thai food?

And everybody's like, oh yeah, yeah, Thai food. That sounds great. There's this moment when it's like, yes, that is what we want. Right? Like, that's a really tiny example. And that's not like, that's not like devising a new solution, like a win-win in like a really deep way.

But it is like there's that moment when the group goes, oh yeah, Thai food, that's what we want. Now suppose the Thai restaurant is closed. Oh shit, what do we do now? Well, it turned out that what we wanted, well, what we thought we wanted is actually not available. And so we now need to figure out again, what do we want? And so there's this ongoing, like, how do we get in sync enough to really get clear on that?

Because again, with a compromise, Nobody's actually fully satisfied. And so you remain in a state of conflict. It's actually like you're pulling still, like trying to get a little bit more for yourself versus for, you know, versus like allowing. And that's the whole frame of compromise as a type of solution is profoundly limited and flawed. You know, it's arguably, yeah, it's sacrifice, right? And, and like, You know, suppose you and I were on a canoe trip and your lunch bag like fell into the water and we lost it, right?

To a fish or just the water. And so now we've got, you know, we got a day left of this canoe trip and we only have one person's worth of food, kind of. Like, I'm gonna share my food with you.

[50:01] Paul: Thank you.

[50:02] Malcolm Ocean: Not as like a favor to you, but because I want you to A, be relatively happy, right? B, be nourished enough to keep canoeing. Like, and so it's like, okay, we're now in a situation of scarcity, but like, I'm going to share with you. And it's not— again, it's not even quite kindness. It's just as a two-person system, obviously the thing to do is divide the food in the way that is going to nourish us collectively as best as possible. Right.

Now, if we were kayaking, say, instead of canoeing and we each had our own little kayak and, you know, and we weren't really like that close friends, we just happened to have set out together. I might have been like, you know what, man, I just want to keep kayaking for 2 more days. Like, you can go back, you know, here's a Clif Bar, right, to get you back to the— what, like, you know, depending on the situation. 'Um, but like, if I want to keep hanging out with you, then I want to make sure that your, your needs are getting met,' and so forth. And, and that would be genuinely what I wanted. Um, similarly, it's like, you know, suppose you have a, uh, a couple, right?

And they're, they're going out to parties, and the, um, uh, let's say the, you know, um, the, uh, the man is often getting tired and, you know, wants to go, um, home early, and the, the woman like wants to stay out later. And so they're kind of feeling into, okay, we're out at this party. What are— actually, before I gestured as if it is a pattern, but I actually want to first just focus on a local situation. They're at this party. The man wants to go home. The woman's like, I want to stay out.

And they feel into it. Like, what do we want, therefore? And again, because they are two individuals, not a single individual, they do have an option of one of them leaving and the other staying. Paying. Um, but, but they also really highly value being together, whether that's just because they want to spend time with each other and, you know, be, be a unit, or whether that's just literally like if one of them drives back, the other's gotta like take an expensive taxi or something. Um, and so, so they want to stay, they want to stay together at the party, but they're sort of realizing, oh, you know, or they want to stay together.

Um, hang on, let me just center a little bit. Like, So it might be that on this particular night, the woman's like, okay, cool. You know, I'm fine leaving this party. Like, you know, we can just head home. Or it might be that the man is like, you know what, I'm actually fine staying like, you know, a bit longer because you really want to be here. Again, there's no right answers to any of this.

And importantly, and so one version of this is where the person is actually like resentful. Like they actually don't want to stay or they don't want to leave. They don't feel like they're, desire has been adequately held by the whole of the two of them such that the decision is really including that desire. And in that case, you've got like a breakdown of trust and of like collectiveness of the group. But if they both feel like they've really adequately put in, you know, like, I really want to stay, I really want to leave. If they both feel that that has really been heard and held, by the collective, then they'll come to some sort of conclusion.

They'll be like, oh yeah, I guess, I guess, I guess I am fine leaving. Like, you really want to get some sleep. Or, oh, I guess I am fine staying. You really are enjoying the dancing here. And like, they actually want that. Like, in the context of being part of this collective, this relates to the whole utopia thing from earlier.

They actually want that.

[53:48] Paul: Yeah.

[53:49] Malcolm Ocean: Now, if that pattern continues, they're going to go into a space where they're like, we need to redesign something here. Like, we need to bring two cars so that you can go home early and I can stay. Or we need to find different kinds of parties that don't tire you out so much. Or we need to get you a nap in the afternoon so that you are more able to stay out later. Or we need to have parties at our house so that you can go to bed while I keep entertaining people. We need to find some solution that actually satisfies both of us.

You know, if, if, if this is a big deal, and it might be that it just goes back and forth, right? Like, it's just, you know, sometimes you do this, sometimes you do that, and it's like, actually fine. But again, it's not a compromise because you're actually deeply sensing into what each person both wants. And, and so it's like, even if in this moment we pick a solution that looks like just what you wanted, it is actually— it can actually be what we both wanted because I want you to be satisfied and I, and I can, we can sense the degree to which we both care about this. And so as long as it doesn't build up, like we keep doing it your way and not my way, then you can actually have a shared sense of like what we want.

[55:03] Paul: I love these.

[55:04] Malcolm Ocean: Okay. That's not the clearest I could possibly articulate that, but I feel relatively satisfied. I love— what do you, what do you think to bring up?

[55:10] Paul: I buy it. I love these examples because what you're doing is bringing the complexity and like multifacetedness of human desire and needs alive, right? In the wilderness, there's a survival component and making it on the trip of like canoeing or kayaking. In a relationship, there's the sense that we wanna play an infinite game with each other, right? I think what happens when, as soon as people start working, is the easiest thing to do is sort of do it how most other people are doing. And in large companies, it's, well, the most important thing is like profit.

And then that gets even simplified down to the highest ranking person's insecurities and pet peeves. So oftentimes you're sort of just serving you're kayaking with a bunch of different people and the person out front just happens to be the loudest, most powerful. So everyone just starves because that person always eats, right? And it sort of works as long as you're ignoring that people have lives, needs, they're hungry and things like that. And I think a lot of what people are realizing when they go self-employed or even just coming to this awareness in big organizations, I think remote work did this for people in enormous ways is like, oh, I have other needs. I shouldn't compromise just because the company is busy or has to do all these things.

[56:56] Malcolm Ocean: Yeah.

[56:57] Paul: Yeah, I love that. And this is what makes it so damn hard. Right, is because the easiest thing to do is like, well, all these people have all these needs, but like, it's just easier if we pretend they're just workers, they're just showing up, and they're just responsible for tasks. Not that they have like envy, jealousy, ambition, all these things that just make everything—

[57:22] Malcolm Ocean: resistance, you know.

[57:24] Paul: Uh, so yeah, would you say that like It's basically just about creating some sort of meta process, like a way of talking about what you're talking about, because I encountered this too in some of my coaching with organizations. It's like they're like, we need a process. I'm like, well, you don't even have a process for talking about process. So how are you ever going to do this? So often what I have them do first is establish a team that's only responsibility is talking about the process. Oh, neat.

Yeah, yeah, yeah.

[57:59] Malcolm Ocean: I'd be curious to explore more what your, what your corporate consulting and stuff has been like, um, like, you know, recently with all of this. Um, but yeah, like, I, I think that there are, there are processes, but even before that, there are something like, um, something like beliefs or assumptions or paradigms or something that can dramatically facilitate or get in the way of being able to, um, come together. Broadly, broadly construed. And so like, you know, one of these things is people often have a belief, explicit or not, that if I think one thing and you think another thing and these things seem to be different, then one of us must be wrong. Common belief that people have. But it turns out that your, you know, your left eye and your right eye see different worlds.

They see slightly— they see the world from slightly different angles. They in some sense disagree about what's— what is going on, but the disagreement isn't actually that one of them is wrong. It's just that there are two different vantage points. And if you try to argue it, then you miss out on depth perception, um, which is like the actual benefit of having these— having this difference is not like fighting it out, but like using it to go deeper. So, you know, if you have an assumption that if we disagree, one of us must be wrong, then you're going to have a lot harder of a time finding the depth perception between your two views. Um, on the, on the flip side, you know, um, or like, you know, on the other end of the sort of, uh, perception, uh, sense-making, agency, or like action kind of loop Or values or something.

It's like if I want something and you want something else and these things seem to be incompatible, I mean, they maybe even are the way that they're stated. They're just like straightforwardly incompatible. One can have a sort of assumption. Again, it could be explicit or it could be implicit that how this situation is going to be resolved is that one of us is going to overpower the other and assert you know, like my, my way or the highway kind of thing, or that we're going to end up with a compromise. But that's not in some important sense true. We could find a thing that both of us like at least as much as the sort of theoretical I win, you lose option.

Like, there's— there is no reason why such a thing couldn't exist in principle. And also, such things often exist in practice. To the extent that they don't, it's because, you know, there's not enough time to find them or not enough creativity or not enough belief that such a thing could in fact exist.

[01:00:45] Paul: Right.

[01:00:46] Malcolm Ocean: Um, or, or there's like not enough slack in the system, right? Like if in fact we are in a, like suppose that we're on the fucking canoe trip and we lose, you know, there's a bunch of us, like 10 of us, and we lose 90% of the food and we're like many days out from civilization. That starts to get a lot more dicey, especially if it's not a canoe trip, but a desert trip. And so we're also short on water. It's like you got some really basic survival stuff going on there. But that is not— even people in poverty are not dealing with such acute, direct, obvious, literal, physical absence of food.

Like, you know, it's not like, it's not literally the food does not exist within walking distance on a timescale that I would need to get it. Like, it's, so I don't know. I mean, I can't, I can't speak with expertise about the nature of how to find win-wins in a context of a lot of poverty. Like, it's tough, you know, and, and that's true even of like little local poverty traps. Like, you're too tired to brush your teeth, but you don't want to go to bed before you brush your teeth. But you can't be less tired until you— tiny little traps people get in, right?

[01:02:02] Paul: I think it's basically just another way of saying these things in groups are very hard. However, we sometimes forget that we aren't fighting for survival sometimes, and there is more possibility and abundance to go around than we can imagine.

[01:02:21] Malcolm Ocean: Yeah. And then we, and that in most situations, we want to at least try finding a solution that deeply satisfies everybody, but that requires kind of, as you were pointing out earlier, that requires actually being with what you really want, not just sort of like the surface level, like, oh, what would be fair?

[01:02:40] Paul: Yeah.

[01:02:41] Malcolm Ocean: Like, or what would be the usual way to resolve such a situation? It's like, no, no. What do I actually want? Maybe I don't care about this thing at all. And I'm happy to just let you have all of it or whatever. Like, you know, in the thing.

And like, that's— and I'm like, great, you know, I just didn't need that. And yeah, so finding those win-wins is kind of a huge part of that. One of the puzzles— somebody was asking me about this just yesterday— is like, you know, they were saying, in my— you know, I'm starting an organization and I'm trying to figure out whether to hire So she was saying, I'm, I'm interested in this work you're doing on collective wisdom, and I'm trying to figure out whether to, um, like how, how to prioritize it in relation to this nonprofit I'm starting. Like, and concretely, I'm going to have to make hiring decisions, and I'm trying to figure out to what extent should I be hiring people based on their ability to just execute on concrete stuff, um, you know, to just do good work, versus on their ability to do something like come into sync with a group.

Like, how do I prioritize those factors given that, like, pragmatically, you know, I obviously, if I found someone who just had tons of both, that would be great. But insofar as I'm going to find myself making trade-offs between these two things, where do I make that trade-off? And from my perspective, this is currently kind of an open research question. Like, clearly these both matter. Um, it depends a bit on like what timescale you're doing. You know, if you, if you just have you know, a one-off concrete project, maybe you just want to hire someone on Fiverr who has proven that they can execute on the thing.

Like obviously in that case that, you know, by contrast, if you're like trying to find like your co-founder for like a multi-decade, whatever, like you're going to really want someone that you can really talk to. And like, you know, as, and as long as they have enough of the relevant skills, like that's going to be more useful than if you've got someone who's got all the skills, but you can't get on the same page about what you're trying to do. Right. Um, but then it's like in between, it's like, okay, what do you do? And also like, what is the best available technology for deepening your capacity to come into sync given two individuals? Like given, given who you're starting with, how, how well can you learn how to do that together?

Um, and yeah, when I said I was working on collective intelligence and so on, these are some of the questions that I'm kind of looking at with that. It's like, how do you, how do you learn how to do that? How can we show other people how to do that? Like what's, um, how deep does it go? Like what, what does it feel like for a group to get really, really in sync?

[01:05:17] Paul: Yeah. Um, you've written about, you know, I've had some taste of that, but you've written about this phrase, participating in an attitude. I think you might've been referring to Twitter. Um, but does this relate somewhat?

[01:05:30] Malcolm Ocean: I think so. Yeah. It's like, Um, so that, that phrase came up in the context of a thread that I had where I found that this, uh, somebody had made a, uh, an app that reminded me a lot of Complice. And there was, there was some energy of like competitive fear that arose in me, like, oh no, is he going to take my customers? And then I was like, honestly, like, you know, it's still the case that only, uh, something like 15,000 people have ever tried Complice. Like, um, it's a very small number ultimately, right?

Um, and then, you know, some hundreds of those are paying customers. And so it's like, this guy can succeed and I can succeed, like, right at what we're doing. And if he makes something that's actually just entirely better on every front, then like, hell, I would want to use it, you know? Um, and so it's like, there was sort of an attitude of like, Finding, finding the win-wins of like, you know, given that I love doing design, design thinking and, um, you know, looking at interaction design and so forth. And I like doing business strategy and so on. Like, dude, can I help you with this?

Like, you know, rather than kind of taking an attitude of, oh, this guy's a competitor. Um, and so, yeah, I would say there's a similar thing where like the attitude I'm talking about wanting to invite people to participate in is one of Finding win-wins. How can I do more of the kind of thing I want to do? Because, and this is part of like, you know, the real value of diversity in, in like the most basic meaning of that is that people have different approaches. So they see different things and they, um, they can, uh, they want to do different things. And so there are these natural win-wins in a way that there wouldn't be if we were all like identical, um, because we would all want to do the same thing.

I mean, even that hypothetical is a bit contrived because at the point when everybody is identical, it is hugely evolutionarily fit to become weird because it lets you do— it lets you do things that other people don't want. So I don't think there actually is an attractor in the space of everybody is identical. Um, it's— it— even with the level of like identicality that people have, it still leaves so many unexploited niches for going and making a little one-person business. And yeah, and so it's like participating in an attitude of finding those win-wins, finding where what I want to do and what you want to do can come together.

[01:08:04] Paul: Yeah, I wanted to shift gears a little bit, talk about some of the things you, you wrote about. You have like so many techniques to like getting this stuff. Like I think a big challenge of working on your own is actually doing this stuff. You, once you figure out what do I like doing over long stretches of time, actually getting yourself to do them and take action on them. You highlighted a couple techniques which I'd love to just explore the thinking or like how they've worked behind them. One is making an appointment with your saner self.

I loved this idea. It sort of felt like cognitive behavioral therapy in like sort of communicating with, or maybe like IFS type stuff. But yeah, talk to me about like making an appointment with your saner self when you're like struggling to do something you want to do.

[01:09:00] Malcolm Ocean: Yeah. So it's, there's sort of a few, a few lenses on that. I mean, one of them is like, even before you're struggling, it's just like, what does it look like to set aside time to have, have a conversation with yourself to look at whatever there is to look at about what you want and how you're going to do it. And that a huge part of the value that people get from taking the time for a meditation retreat is not even the teacher saying anything at the retreat or whatever, or going to a workshop. It's not what they say at the workshop. It's just the fact that you spent an entire day looking at your stuff.

And I actually think that relatedly, like something that more people could benefit from is like instead of like paying a teacher for a multi-day retreat. I mean, you may need that for various reasons, but if instead, if you have a friend that you trust a lot, basically you and the friend take a weekend each where you hold space for each other's retreat. So it's like, like one, one weekend is like, you know, Paul's retreat and Malcolm just shows up and is like, they're supporting Paul to do introspection for like 3 days straight. Um, and, um, and that could be introspection on the level of like strategy, writing out like your goals and stuff and like thinking about that, or it could be introspection on the level of, um, you know, deep emotional work or whatever.

But the point is like what we actually have is unlike a workshop where, you know, you only get, you know, an hour of sustained attention from the instructor before they have to move on to somebody else and you're just then kind of doing your own thing. It's like we have 3 days straight of attention just on you. Um, and so it's like you can really kind of go deep into stuff and unpack it and, you know, you have more working memory because there's somebody else there holding it with you.

[01:10:50] Paul: Um, and have you done this?

[01:10:55] Malcolm Ocean: Uh, yeah, yeah, I did it with a friend of mine. We didn't actually end up, end up swapping and we were sort of intending to, but then a lot of things happened, including COVID. Um, but we, um, Yeah, we just rented an Airbnb for like 3 days and just spent the entire time looking at ways in which I was feeling stuck and it was really healing. It was really powerful on a whole bunch of levels. Now you do actually have to have adequate techniques in order to do that. Like this is a little bit of an advanced thing maybe, right?

Like if you were, I don't, but I mean, even there, like everybody has more wisdom than they're actually accessing most of the time because they're most of the time in too much of a rush to just slow down and find it. So like, I think unless you would be likely to kind of go off the deep end and get dysregulated in some way from doing such a thing, I think it's basically a good idea. Even if, even if you're just working with some basic goal setting techniques or just like trying to put into practice the advice from some book you just read that you like, I think that would, I think that would all be worthwhile.

[01:11:52] Paul: Yeah. I liked your saying yourself technique. It was sort of put an appointment on the calendar, deal with like bring attention to something you're struggling with and then give the advice you would give a friend in that same situation. Right. And oftentimes you can sort of short circuit your own automatic processes to say, oh, okay, I can.

[01:12:16] Malcolm Ocean: Yeah. And funny thing about that, like, so I think they've actually studied people give— people come up— people are better at solving certain kinds of problems when they step out of their own shoes. So like, um, like you ask people like, what do you, what do you think you should do in this situation that you're in that you're struggling with? And they go, oh, I don't know. I mean, I just, I really, I just, I can't, whatever, whatever. And then they're like, what would you say to a friend who was in this situation?

They'd be like, well, I mean, why don't you try talking to that person? It seems like they understand something about it. And then maybe you could get them to like help you talk with the other person. And then they're like, shit, that's a good idea. And part of what's going on there, as far as I can tell from what I've learned about how brains work or something, how minds work, is that people literally have beliefs about themselves that aren't identity beliefs. It's not a belief about who everybody thinks I am exactly, but it's a belief about the world that only applies to them.

So it's something like, if I ask for what I want, you know, everyone will hate me and I'll die alone in a hole with no friends. I mean, it's not— Anyway, something sort of to that effect. Now, they don't think if anyone asks for what they want, that person will die alone in a hole with no friends. They just think that about themselves. And it causes them to not notice certain kinds of moves because from their first-person perspective about themselves, those moves are just not available. Um, even though they're really obvious once the person is looking at their situation from the outside.

Having— so having said that, like, one update I would make that SaneYourself post since I wrote it is I would acknowledge, like, sometimes you're going to come up with advice that you don't feel comfortable taking because it would disturb some thing about your sense of self. And well, it seems like that's okay.

[01:14:09] Paul: It seems it might just be more beneficial just to generate more ideas. Like just that practice of expanding imagination is something that I think so many people would benefit from.

[01:14:21] Malcolm Ocean: Definitely. Yeah.

[01:14:23] Paul: Another thing you wrote about was just this idea of starting small and trying stuff. This kind of connects back to what we were talking about at the beginning. But what does that mean to you? I've, I've sort of implemented a simpler thing similar thing, which is— which I've called ship, quit, and learn, which is basically design finite experiments that I have to ship, and the only goal is to kind of learn something.

[01:14:50] Malcolm Ocean: Hmm, cool.

[01:14:52] Paul: Yeah.

[01:14:53] Malcolm Ocean: Um, start small. Not sure what that connects with. I mean, one thing I like to do is like, it feels connected to a thing that I think is not quite the same thing, but it's maybe related enough. Which is like, like rather than trying to like perfect a blog post and then publish it, like just throw out a tweet that just tries to say in one tweet what the blog post is trying to say. And like you can get a lot of deeper insight from just doing that, like in how people respond to it and so forth. Or, you know, just write a Scrappy thread.

Um, Yeah. I mean, like, there's something to be said for thoroughness, but there's also— I actually had an interesting conversation with this, with, with Andy Matuschik about this. We met up here in SF a couple weeks ago, and I was describing how my, you know, my software company Complice could not have succeeded if I wasn't very non-perfectionistic about it, like very willing to cut so many corners and, you know, have kludgy solutions that were half-baked and that are challenging to build upon now. But like, if I hadn't done them at the time, things would have just fallen apart. And he was, he was struck by how that was so different from this attitude that I seem to have towards this collective intelligence stuff and collective wisdom and superorganism and so on, which is like very thorough and like trying to like really get it right in a certain way, like trying to really nail it.

And he was like, that's interesting that you have, like, you know, on the technical and, you know, strategic levels, like so much willingness to like be sloppy and scrappy and stuff. But then you have this orientation towards the like teamwork elements that's like, no, like go really slow and meticulously. I don't know what sense to make of that actually, to some extent. Like I still haven't, like he pointed out something interesting and I'm actually genuinely not sure like why that is in me and whether I think it's actually in some sense like, like whether I would advise other people to take a similar approach.

[01:17:10] Paul: Like, is it simply because the code is hidden and sort of the words you're thinking you're doing is more out there in public?

[01:17:18] Malcolm Ocean: Well, it's not that, it's not that I'm taking a thorough attitude with respect to my writing. It's that like with respect to the actual like coming into synergy of groups, it's like I have this attitude of like, like let's go all the way kind of thing rather than like let's kind of, you know, half-ass this and like be, be, you know, collaborative enough to get stuff done but like not really worry about like whatever. And I think that like part of what's going on there is, I mean, the nature of it, it just is different, right? Like with Complice, I was trying to build a business and so the most important thing was just is this working for my existing customers and can it like, can it scale enough to make it to the next stage? Whereas with this collective intelligence stuff, like the thing I'm trying to do is like figure out what the future of human thinking looks like.

Um, it's a much, it's a much deeper project and not one that is trying to hit short-term feedback stuff in the same way. Like you sort of, yeah. Yeah. Which relates to like, that's not really start small and try stuff.

[01:18:19] Paul: That's like start big. And try stuff.

[01:18:22] Malcolm Ocean: Right. But even there, it's like, there is still totally a start small, like, you know, like the, the sense that I have is like, you know, okay, you want to be practicing this group synergy stuff on really small scales. It's like, you know, uh, 2 days ago, um, I was, uh, I was out at a, um, sort of festival thing and some friends and I went for a hike. And we just kind of left the grounds and we were kind of like, okay, we want to go up. And we decided to try following this riverbed. So it was somebody I was close to and then a couple of people we just met that earlier that day who also wanted to go for a hike.

And so we were kind of figuring out, okay, let's go up this riverbed. And I had like sturdier clothes on than the others. And I was kind of bushwhacking a bit at the front. And there was kind of this tension of like, I wanted to keep going. They wanted to turn around. It's like, okay, right there is a little case study in group decision-making.

How do we decide, do we go forward, do we go back, do we split up? And what are the factors there and how do we figure out what we want? And I ended up encouraging the group to go substantially further than they initially wanted. And I think they were ultimately fairly satisfied with some experience that they had as a result. But I, but they were definitely taking a bet on me. Like it might've been less pleasant and they might've been kind of annoyed and I was taking a bet that like it would pan out, right?

And like, and we, you know, we were feeling into it and yeah, so it's like that, you know, that's another start small case. You know, it's like if you want to practice doing superorganism type stuff, like, you know, go on a road trip with someone, like road trips are a great context in which you're like kind of, or a hike, but like Like either of the— the neat thing about a road trip compared to a hike is that there's sort of a clearer role differential. Like the person in the passenger seat is sometimes like literally feeding the driver, you know. And there's also, you know, some constraints that make the whole thing more interesting. And I think people are actually in a lot of cases quite good at figuring this stuff out in little local decisions like a road trip.

I mean, sometimes it's a shit show, but like you can get, you know, like compared to the kinds of messier decisions that you'd be trying to make in like doing business strategy or design or something, just the basic stuff of like, okay, yeah, when do we want to stop? Like, do you need to stretch your legs? Do I need to go to the bathroom? Do we need to get some more Gatorade? Like what's, you know, and, um, you know, and just dealing with the contingencies that show up like, oh man, the cheese totally melted on everything.

[01:20:58] Paul: Like, Yeah, you know, like, how do you deal with— I mean, I like talking about this stuff, but a lot of people just don't really enjoy participating in these kind of like meta conversations. How do you think about that in the broader aspect of like what you're trying to accomplish?

[01:21:18] Malcolm Ocean: Yeah, that's a good question. So I think it's a few things. Like, one is there's some amount of like what I'm doing at the moment, you know, is going to have some early adopter-ish type people, you know, people who are more drawn to it than others. And in some sense, I'm focusing on those people. Like, you know, I don't— ultimately, I see this as a cultural platform evolution that will spread to all of humanity in the same way that the— and not just from me, but from all the pockets where it's emerging— in the same way that, like, you know, agriculture and writing, you know, produced changes that just spread to all of humanity. But, um, but it's not going to spread equally or linearly or, or all at once or anything like that.

And, um, and so, so two things on that front. Like, one is that, like, you know, the people who are more drawn to it now are going to be the people who want to do more meta-ish stuff, right? Um, and that's, that's just fine. Um, two is that I think we'll get better at something like teaching or training or conveying to people both how to do this meta stuff and how it can be fun and satisfying and stuff. And also how to come into like deeper group flow without needing to have so much meta. Like I think that the kind of heady meticulous quality that a lot of this has right now is partially because we're actually in some ways still really new to it.

Like it's still, um, like the kinds of questions that I'm investigating in the way that I've been investigating them are, you know, maybe 50 years old as questions. Like I've got this old book called Synergetics by Arthur Koehler written in 1970-something. And, you know, it's very much looking at some of these questions and it's not like people didn't care about teamwork before they did. But they didn't have the same attention to, or care about community or family or whatever. But there's a deeper something that we're attending to about group flow in a fully general way. So with team sports, you get group flow, but the objective is external.

Everyone can see it. You can see if the ball's in the opposing team's net. You can see what the score is. The objective is external. With group flow, where part of what you're caring for is everybody's internal needs, whether those are like, I need to be fed and, you know, like sheltered and various physiological things, or whether those are needs that are like, I need to be singing regularly. Like, that's a need I have, like, you know, in a sense.

And so it's like finding ways to like synergically satisfy all of those is a totally different kind of thing to get group flow around than an external thing like a sports team or even an external thing like simply a company objective, right? Yeah. And sort of like fully general group flow is kind of the puzzle.

[01:24:29] Paul: Yeah. It's funny thinking about sports. It's Sports is one of these weird domains where the goals are often incentivized with the greatest human flourishing, especially at the highest levels. But in many of the other domains we participate in, it's not really aligned that way.

[01:24:52] Malcolm Ocean: And there's kind of a compromising of the body or something that occurs for the sake of, like—

[01:24:58] Paul: I always find it funny when people say the phrase late capitalism. Like, to me it still feels like super early, early capitalism in the sense that, like, we're still just making this up. And like, this is such an early, um, way of thinking about forming larger groups than were normal 200 years ago, right?

[01:25:23] Malcolm Ocean: Yeah, yeah. I mean, I guess it depends in part on Like, guess where you're drawing the boundaries, but what you're calling capitalism or something like that.

[01:25:33] Paul: Exactly. I guess what I'm talking about is just like the scale of doing things with enormous groups of people that we didn't really do before.

[01:25:44] Malcolm Ocean: Right.

[01:25:45] Paul: But yeah. So one question I wanted to ask you, this is the one you asked me to ask you, which I found fascinating. What is at the center of The Pathless Path? Like, what does that mean to you? I didn't— I don't know how I'd answer it, but I think what you're getting at is sort of the inherent, like, mystery and uncertainty of the world. But I'd love to hear your response.

[01:26:16] Malcolm Ocean: Yeah, well, I think that a phrase very similar to that one, I think, shows up in, uh, some Dzogchen writing, um, you know, uh, Vajrayana Buddhist writing, Tibetan Buddhist. Um, uh, I think Ken McLeod has a book with actually a very similar title or something, The Pathless Path, um, or something. And so I do wonder about the connection between those. Um, there's something about the— you can pretend that you know what the future is going to hold. Like it's, but it's possible to have a stance that acts like it knows what the future is going to hold. And, um, and people do this all the time, you know, plan planning as a, as an activity is to some degree, like fantasizing a future and then imagining you can control it and then figuring out what, what you intend to do in all of those, all of those futures.

And, you know, as Eisenhower said or whatever, you know, planning is indispensable, but plans are useless. It's like the act of planning causes you to notice a whole bunch of stuff. But if you're trying to just run your life from the plan, then you, you immediately encounter things are not as you imagined they would be. And like, you know, step 3, turn left, doesn't make sense anymore. Once step 2, walk forward, got blocked by an obstacle and now you can't turn left because there's a wall. Like it's just, Um, so I imagine that what part of what you're doing with The Pathless Path is using entrepreneurship as kind of a vehicle for, um, something like spiritual growth, sort of like how Victor Wooten's book, The Music Lesson, uses learning music as a— it's like that book is arguably a spirituality teaching disguised as a music book.

Or a music book disguised as a spirituality teaching. You can kind of see it either way. And like, similarly, my sense is that part of what you're pointing out is the kind of like stepping into the unknown has a, has a spiritual quality to it. I think I just made a little jump there. It's like, why is this spiritual, right? Like, why is this?

What is of the nature of the spirit to this? See if I can say anything about that.

[01:28:33] Paul: Well, I think that resonates. I mean, just to— yeah, I think what I'm trying to say is that there's something deeper worth finding. Like, being on a constrained path where everyone sort of agrees there is a defined future and way of orienting your life might limit you from going in that deeper direction. And then that deeper direction has a whole bunch of stories we can attach to it— entrepreneur, founder, solopreneur, creator, whatever. They're kind of silly and pointless. It doesn't matter.

[01:29:12] Malcolm Ocean: Mm-hmm. Right. Like those are themselves also paths, right? So it's not exactly entrepreneurship except in the sense of which, like, yeah, yeah.

[01:29:23] Paul: But those shake things up enough that it's going to make you uncomfortable and notice more things. Which then might lead to more interesting paths that you didn't know were possible or even thought about before.

[01:29:40] Malcolm Ocean: Yeah.

[01:29:40] Paul: So it's this sort of like endless journey. And I guess it's a shift from a finite game to an infinite game. But I think also what I was trying to convey in my book is that it might also suck, especially in the short term. Yeah, but that could be worth it.

[01:30:01] Malcolm Ocean: Yeah.

[01:30:06] Paul: Yeah.

[01:30:06] Malcolm Ocean: I, I've noticed that when I think about the things that I've done in my life that I've spent the most time on, and Complice being one case study of it, it's like, there's the sense of like, I would, I would not have managed to do Complice if I had had any idea how much work it would be. Like when I started, unless I'd also known how much more satisfying and worthwhile it was than I could have imagined. So it's like it was both so much more work than I had envisioned and also so much more worth it. And I found a lot of things are like that.

[01:30:48] Paul: Yeah, I think writing a book was like that for me. Probably one of the hardest things I've done, but also one of the most rewarding.

[01:30:59] Malcolm Ocean: Nice.

[01:31:00] Paul: But yeah, so wanted to ask you some rapid-fire questions.

[01:31:06] Malcolm Ocean: Let's do it. I'll see if I can be brief. I'll give you, I'll give you one breath for each at most. That's how I constrain myself. I can take, I can take pretty long breaths. Okay, hit me up.

[01:31:16] Paul: Do you have a path role model?

[01:31:23] Malcolm Ocean: Tim Ferriss was kind of what, you know, was, was for me. Now more like Jordan Hall.

[01:31:36] Paul: Awesome. Yeah. A book or piece of content, podcast, whatever that's been inspiring to you in the past few years.

[01:31:49] Malcolm Ocean: Oh, a few years. I'm just gonna say a few weeks. And I'm gonna say that I really enjoyed listening to John Verveke and Jonathan Pageau talk about— how did they phrase it? Something about like how to actually create angels and like new, new demigods out of collective forces.

[01:32:20] Paul: Wow. Have to check that.

[01:32:21] Malcolm Ocean: Couple of videos on YouTube.

[01:32:22] Paul: Have to check that one out and we'll link that up. What's one thing you wish you did earlier on your journey? Hmm.

[01:32:40] Malcolm Ocean: Something— what actually comes to mind, oddly enough, is like, I wish I'd gotten back into music sooner. I mean, I don't actually have regrets there because it's all so path-dependent, but like, I kind of burned myself out a little bit with the album project in 2012 and stopped. Well, it was partially that and partially I got really intensely, I gotta save the world and like, whatever. And I think I think it— I think I lost touch with the ways that music can soothe me, and I could have benefited from having more of that a few years, like in like 2013 to 2015, 2016.

[01:33:18] Paul: Anything you want to leave for readers, listeners, to follow more of your stuff? Any pitch you want to make them? Any call to action? Yeah.

[01:33:33] Malcolm Ocean: So I mean, we've been talking indirectly a bit about my software and definitely that has the potential to change your life. If you feel like you would like to be doing more meaningful stuff with your life, if you are, you know, if you've been following Paul's ideas and so on and you found yourself being like, hmm, sure would be nice to put this into practice and start thinking about like what I want to do with my life, but you're like not actually doing it. Complice can be a really powerful thing for that. It handles goals on pretty much any level of abstraction. And so, even if things are super nebulous and you just want to put in a goal that's something like make sense of my life, it's like Complice will check in with you every day and be like, how are things going towards make sense of my life? You know?

And maybe what that looks like is like you're in a job and you're like, ah, I probably want to quit, but like, oh, what would I even do? And like you just got those questions. Complice can just help you check in every day. Like, where are you with those, with that questioning process? Like, you know, have you started thinking about what your runway is? I mean, Complice is not going to ask you those things directly, but it's kind of like the SaneurSelf thing.

It's like Complice is going to, you know, can hold you through that process. So, um, yeah, I would, uh, I would definitely suggest, um, uh, checking, checking that out and, uh, we'll give a custom link that'll just give an extra week of trial for that. And yeah. And I would say, like, if you do— if you check into Complice every day for 3 weeks, which is how long you'll have it, like, even if you don't end up buying a subscription to Complice, it can still totally change your life to just have had that experience. Because it— the experience of how it feels to be looking at like, here's my goals, here's what I deeply care about every day, and just asking, how can I make a little bit more progress towards this? Um, has been life-changing for people even when they don't go on to subscribe.

So, um, yeah, but you do actually have to show up. So, um, that's, that's the main thing I'd like to, um, like to invite you to do. And feel free to reach out to me, you know, tell me on Twitter what you think of the app. If you you try it out. Um, even if you're just like, I got 3 steps in and I got stuck, like I'm interested to know that. Um, I, I sometimes make big changes based on what people say when it highlights something new and clear and crisp.

[01:35:59] Paul: So very cool. I'll link up to your website as well and your socials. Thanks for joining me today, Malcolm. Yeah.

[01:36:08] Malcolm Ocean: Thank you so much, Paul. This has been great.