Proactively learning to think *about* what I think with

John Shotter, in More than cool reason: ‘Withness-thinking’ or ‘systemic thinking’ and ‘thinking about systems’, writes about the difference between “aboutness” and “withness” thinking. The former tries to look at the world objectively: to place oneself outside of what’s being looked at. The latter includes the self and its relationship to the whole in the sense-making.

The cover of John Shotter's book "Getting It: Withness-Thinking and the Dialogical... in Practice"

He describes how with complex situations, which includes many social ones, we need to use withness thinking, because we don’t just need to learn new things but we need to become something new. In these situations, we’re changing not just what we think about but “what we think with”… how we relate to our situation.

Hence these kinds of changes cannot be produced by following intellectually devised plans, procedures, or protocols; they cannot be done, intentionally, by people taking deliberate actions—this is because the coordinated execution of planned actions depends upon all concerned already sharing the set of existing concepts relevant to the formulation of the plan, thus all new plans depend on old concepts – the process results in the “continual rediscovery of sameness.”

This is something that makes a lot of sense to me, in many ways. I’ve written before about the idea that some things have to be learned by abstracting from experiences, rather than by being told something or otherwise following a series of steps.

It’s also something I find kind of scary. I found it scary two years ago—I know this because I wrote so in the margins of the article when I first read it then.

Tonight I realized why.

(If anyone cares, I wrote this post about 2 weeks ago, so “tonight” actually refers to Nov 2nd)


Most people reading this probably know that I’m the creator of Complice, a company based around setting and achieving goals. Uh, and if you don’t know, now you know 😉 Given that, it’ll come to nobody’s surprise that I tend to take a very goal-directed approach to my life. There are (at least) two kinds of goal-directedness, which map onto Shotter’s model as theory-based and methods-based, both under aboutness-thinking.

I’m not an expert at theory-based goal-directedness, aka planning: laying out a series of steps to take to achieve my goals. I’m actively working on it, but so far it’s still a process of even bothering to make plans, let alone making good ones.

I am pretty good at staying consistently focused on the question of “where am I trying to get and what do I need to do to get there? This is the methods-based kind of goal-directedness: a focus on continually aiming towards the target, the outcome. Striking the enemy, if you’re a swordfighter.

They work really well in situations where the situation can be relatively well-modelled, where you have a good sense of what will work and what won’t.

Effective non-goal-directedness

I’ve also, over the past few years, become better at doing things without deliberateness, but as more of an improvisational process. I’ve had to, because that’s the main way that things happen in the intentional learning community that I’m a part of. I mean we’re not totally formless. We schedule events (although much less so than most other groups I know) and we sometimes use explicit conversational forms like people taking turns to speak.

But for the most part, we don’t have many goals, or milestones, that we’re aiming for in the short term. We make progress, and we experience the progress we’re making, but we don’t usually know the direction that progress will be in until we’re already mostly there. We’re not pursuing it directly.

I’ve… gotten used to this. And, it’s hard. It’s a different way of operating. It’s also the way personal and collective growth naturally work, in many ways.

The first time I did a yearly review blog post (2012) I concluded that my year had been “A Year of Projects”. This made lots of sense. I then predicted that the following year would be “A Year of Text”, because I was expecting to do a lot of reading and writing. This ended up being a hilariously irrelevant prediction—in part because I didn’t read & write as much, but also because even if I had, I don’t think that would have been the most meaningful/salient part of my year. In yearly reviews since then, I haven’t even bothered to predict.

What I realized tonight

As I said, I’m part of this intentional learning community. And we have a big long-term goal, which is to develop this new kind of culture and share it with the rest of the world.

For the entire time I’ve been involved here (~3.5 years now) I’ve had a certain kind of impatience about this. This impatience has produced a bunch of tension between me and the rest of the system, where I’m constantly trying to figure out “what’s our bottleneck? what do we need to do next?” but the situation is one that calls for a bit more withness than that.

So I’ve experienced this oscillating tension, where sometimes I’d be trying to push forward, and then, frustrated that that didn’t seem to work, I would stop trying to directly pursue anything, and would become a bit disengaged or only responsive. Not very self-authoring.

And not very effective. And stressful.

Tonight I realized that the cause behind this tension and flailing was that I didn’t know how to be proactive except by deliberate pursuit. This was a gap in my knowledge. And there was a corresponding gap in meta-knowledge, where it hadn’t occurred to me that there might be a withnessy way to be proactive. So when I felt really engaged, I would then try to be direct and goal-oriented… which would mostly fail, causing me to disengage.

What’s fascinating is that in this moment I still don’t feel like I know how to do it. Like I don’t actually see the third option, that’s proactive and yet doesn’t assume that I know anything about how it’s going to work. But I have the sense that it might be there, and that makes a huge difference.

How I’m already good at this (or related skills)

I think it’s worth exploring though… to what extent do I already know how to do this? Maybe I have some relevant knowledge/skill, but haven’t been applying it.

Let’s see. When I was going to burning man for the first time in 2014, some people asked me what I was hoping to get out of it. Did I have any plans or intentions? I responded, “I really don’t know! I expect that I’ll be glad that I went, and that’s enough to make it a good decision to go.” So this is an example, I guess, of me creating an experience for myself that I expected to ultimately get me closer to where I want to be. Even my trips to the Bay Area these past two summers have had a kind of improvisational quality to them.

And in general, I’ve done a fair bit of going-to-events-not-sure-why. I understand the jist of Thus Spake Zarathustra because I randomly attended a graduate philosophy seminar. Met a cute girl there too. Neither of those had a profound impact on my life, but it’s the kind of thing that’s relatively high-variance. A different seminar I went to taught me about a really useful concept called the Logic of Appropriateness, which I’ve used to make sense of lots of situations. Attending that same seminar a different week caused me to find out about Contact Improv, which was intrinsically fulfilling and also caused me to meet the intentional community I’m now part of. Pretty huge impact.

This still feels kind of like not the quality I’m looking for though. Like it’s too big picture. It involves plans and procedures, they’re just really broad. It’s not a “what do I do today? and tomorrow?” But okay, what’s above is similar but not quite it, which is still helpful to know.

I thiiiink that my recent blog post, “What’s it like to be you?” is a good example. It describes me on a quest at burning man, kind of trying to figure out the titular intersubjectivity question. I definitely had that as a purpose in mind, but I wasn’t impatient about it. I was navigating the situation by going towards whatever felt attractive, while simultaneously holding an awareness of this intention.

I think I do this reasonably well in my life-coaching conversations as well. There’s a general goal there—help the other person be more productive/effective/rested—but I don’t go into the conversation with a particular plan. Instead, I’m making sense of what they’re saying, offering suggestions, asking questions, and trying to navigate their situation based on all of the knowledge that I have, from reading and from my own experiences and those of other people I’ve talked to. Much of the coaching I do is in one-shot half-hour calls with new Complice users, in which I don’t have much of a chance to make a complex plan for how they could change, and instead I need to just give them a quick nudge.

Complice + withness?

Hmm… I’m now reflecting that the very nature of Complice can be somewhat conducive to this whole thing. Sure, it’s explicitly goal-directed, and the process of putting in daily intentions often runs counter to the withness thinking style, where you don’t actually know what the most valuable things towards a given goal will be that day.

But another use-style that Complice supports fairly well is not putting in intentions for a given goal, and only logging at the end of the day what you did. This means that you’re keeping this general goal in mind throughout the day, and you get to be opportunistic. Research shows that this is one way that goals work—they help focus your attention on goal-relevant activities. One user reported to me that they actually found this aspect of Complice (the goal-related opportunities that they wouldn’t have seen without it) most valuable. This is by contrast to most to-do systems in which you only ever put in tasks that you’re doing in the future, and you don’t ever log things you’ve already done.

So there’s something to that too, maybe.

How to implement this

So it seems that I do have a bunch of the relevant capacity for this stuff. How can I apply it? In particular, how can I get out of the trap of the oscillating tension between proactive direct pursuit and disengagement?

(I’m thinking about this as I write.)

(Also, this very thing has a reflective property where it itself is a kind of thing you probably can’t directly pursue.)

I think one piece of it is: proactively pay attention. There’s a lot to notice in the system that is my house, and if I try to think of “what would it be like to be a version of me that’s more engaged?” then I suspect that that Malcolm would be more aware of things.

What else? Related to just noticing things in general, it might be helpful if I pay extra attention to experiences of discomfort (particularly awkward laughter). In my experience with subject-object interviews, trying to assess people’s limits of their ability to look at their own thoughts effectively, it seems like nervous laughter is a common sign of someone being at their limit.

Aha, which suggests something else: deliberately cause experiences that will strain the limits of your ability to make sense of situations. There are lots of ways to do this. One relatively tractable one is to have a conversation about a relevant, complex topic, with someone who’s an expert relative to me. Try to understand what they’re saying. Try to understand why they’re saying it. I’m noting that I already do a bunch of this in this context, so it’s not actually that instructive.

How else can I get more model-breaking input, particularly in this context? Reading books I think can also help with this. I’m currently reading The Evolving Self, another book by Robert Kegan about Constructive Developmental Theory, which is talking about the various ways in which people’s abilities to make sense of the world are limited. So that’ll help too.

This doesn’t feel quite proactive enough for my liking though.

think, think, think

So… Shotter seems to think that theorizing is solely part of aboutness thinking. I think that more nuanced theorizing totally has a role in withness thinking. For instance, I suspect that Shotter’s model of theories (page 7 of this pdf) doesn’t include much “strong opinions, weakly held“. His model of theories is pretty narrow—almost a strawman, even. No arbiter is saying that models have to be as he describes: eschewing examples, universal, context-free, complete, and placing the self outside the model. My sense is that creating simple explicit models based on one’s personal understanding, and then testing them unattachedly while doing the normal withness motion of interacting live with the system and paying close attention… can be a really great way to proactively engage without just trying to hit a short-term milestone.

I’m reflecting that in order for the project we’re doing here to move forward, it’s not enough for Malcolm to level up. Whatever I’m doing needs to feed back into the system, and I feel like this part needs to be proactive too. And yet it won’t work to just push other people to change.

So that’s going to be my practice:

  • pay attention, particularly to discomfort
  • notice where my models break
  • build explicit models to make this clearer
  • notice and nudge at the limits I see elsewhere in the system

(This blog post is kind of me thinking things through in public, but I will note for others’ sake: being around people who care about you relatively non-conditionally is really helpful for feeling safe enough to let in model-breaking input. That is, it feels a lot easier to have your worldview altered when you’re in relationships that you’re not worried will end just because you changed your mind about something.)

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About Malcolm

Constantly consciously expanding the boundaries of thoughtspace and actionspace. Creator of Complice, a system for achieving your important goals.

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