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

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

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

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

Taking myself seriously

My last post was about taking myself seriously, and I remarked:

“This blog post is going to be the first in a series of several posts on the subject.”

This is part of why I haven’t actually posted anything recently. Turns out writing a sequence is hard. I have spent at least a dozen hours (maybe two) refining the ideas in those posts, but it’s been hard to figure out what order to put everything in. I have no idea how people write books. Okay, some idea: slowly.

But since I felt like I had to publish the rest of the sequence before publishing other things, I found myself not writing other things, even though I had things to write. (To some extent I may have also experienced something like a vicious rock paper scissors dynamic, where I had some energy to write about some new thing but felt like I had to work on the sequence instead, but didn’t really feel as motivated towards that, so I didn’t write anything.)

But I’m feeling okay about all of this! And that’s what’s really changed.

Relaxing my need to push forward

Back in September, I was noticing a bunch of tension emerging between some of my motivational structures and the way we’re doing things here at the Upstart Collaboratory, the intentional learning community / culture accelerator I’m a part of. I was navigating a kind of obsessive get-it-done pattern that can very easily get fixated on doing some particular task, to the exclusion of paying attention to what really makes sense in the moment. This kind of focus is powerful, but needs to be used strategically or it produces a lot of motion in a direction that doesn’t matter.

(My sense is that this is similar to the phenomenon where someone takes a stimulant to do work, but ends up, say, very intently organizing the folders on their external hard drive instead, because that caught their attention before the work did).

I was experiencing a lot of internal pressure to make progress. This pressure has been really powerful for me, driving me to do tons of writing and coding and other work—I owe a lot of my success to it. And, it’s limited on its own. I began to realize I really needed to develop the skills of taking a step back, taking in what’s really going on, and taking a followership role, not just a leadership role.

So I stopped working on Complice pretty much altogether for a week, and just focused on reading (primarily the aforementioned followership book, David Chapman’s Meaningness, and The Zen Leader) and really paying attention to my own thoughts and what was going on around me.

I started noticing more opportunities to practice proactive withness, something I wrote about a year ago and have thought about more since. Learning how to do more structured improvisation based on a general sense of purpose, rather than needing to plan my day in detail in advance (which was hard to interface with everyone else here).

This, in itself, was hugely valuable in terms of shifting how I could show up in the context of the Upstart Collaboratory—the culture accelerator project I’ve been involved with over the past few years. The culture that we’re working on building requires everyone to be attuned to each other and to what’s going on in a way that’s basically impossible if someone is caught up in some fixed sense of what needs to happen next (or a fixed need to get seen, or a fixation on everyone in a situation being comfortable.)

The project has been moving forward slowly for the past decade or two in one form or another. It’s only really been in the last few months that we’ve started to take ourselves more seriously as not just a community or a nebulous group of people, but an actual team, working together. So there’s still a huge sense of using my time valuably… but now it’s coming more from a sense of attraction (being pulled towards what’s exciting) than from a sense of pressure (being pushed away from inaction).

My relationship with projects

Following this general relaxation of pressure, some other things shifted. The one in particular that ties back into this blog post about blog-posting is a realization I had about my relationship to my projects.

Early morning in early October, I set out on a walk with Jean, head of Upstart. She was going to work at a café and I said I’d accompany her partway on the walk, but then would go back and do some solo work. This was after that week of doing almost no solo work on projects like Complice or blogging. Partway turned into most-of-the-way, which turned into the parking lot of the café. The conversation as we walked had been really exciting—one frame we explored was of a sort of stand-up meeting between the CEO and CTO of the startup that is Upstart (these aren’).

So there I was, at the café. I was feeling this pressure to turn around and go do some of my own work, but it also really felt like it made sense to stay and continue collaborating with Jean. As we took our first sips of our drinks, it suddenly dawned on me that all of the pressure I was experiencing was self-created and something that I could simply choose to let go of.

It was a weird feeling, because I’d been subject to it for so long and so intensely. But there I was, able to look at it clearly and recognize the stress it was causing me and the real possibility of letting go.

I developed this internal project-pressure, I imagine, in response to feeling the external demands of university and knowing I needed some internal locus of drive that would help me resist the temptation to feel like I should be doing homework all the time when I really didn’t need to. This was enormously powerful: I created this blog, started doing more self-experimentation and making commitments to personal challenges, built several apps on the side, and recorded an album of original music, while staying on top of my studies. This was back in 2011-2012.

Then in fall 2013, I began channeling this intensity into building Complice—in two ways. The straightforward one is that Complice became one of the projects I was focusing on instead of school. But also, the very structure of Complice itself was predicated around the kind of motivation I’d been using—a bunch of different goals/projects, making sure to make a bit of progress every day. Without recognizing this, it might surprise some people to learn that (except for a few weeks) my work on Complice has mostly been “part-time”—20-30 hours in a given week. But in this context, it makes total sense.

Falling in love and getting obsessed

In writing about my Ritual to Upgrade my Face last March, I noted:

“One last [motivation for doing this] was realizing that part of me seemed to be holding back from caring passionately about anyone or anything. I had seemingly misplaced my ability to fall in love.”

Let’s return to the scene at the café. At that moment, I’ve just had a really transformative week being mostly focused on the Upstart Collaboratory work. Yet I’m feeling like I need to do all of these other things. Then I have this realization: it’s okay to fall in love with one project and get really obsessed about it. Even if that means that other projects get put a bit to the side.

It now sounds obvious, written here, but it required a serious cognitive restructuring for me.

(I suspect that it’s in general true that lots of things that feel like they would be NOT OKAY are either actually fine upon further inspection or are not okay only because of some circumstantial factor that could in fact change.)

I really can’t say how much I’ll end up blogging in the next few months. It could be substantially more than my historic 1 post per 10 days, or could be much less. But it currently looks like things have stabilized a bit, and having given myself that space, I’ll find myself getting excited about writing even if I’m not pushing myself to do it.

A portrait of Malcolm Ocean

I'm Malcolm Ocean.

I'm trying to figure out how humans work so I can help make humanity work. More about me.

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