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Conversations #23 - Malcolm Ocean

Systems Designer

A conversation with Systems Designer, Malcolm Ocean—

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Hello Eclectic Spacewalkers!

This past month I had the pleasure to finally talk with Malcolm Ocean, a long-time Twitter mutual of ours. Malcolm Ocean is a systems designer, a self-described “feral free agent, Singer-songwriter, and Trust-dancer.” He also runs a software company called Complice - the to-do list that never goes stale.

Malcolm is a unique and eclectic soul whose thinking I have found to be useful and playful in solving problems, building networks, and being curious about all things dealing with the ‘interpersonal.’ Here is one of his blog posts that summarize these points well.

A Collaborative Self-Energizing Meta-Team Vision

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

In some cases this may even involve me ideating #ThingsIWantToExist, and then finding someone to execute it.

But that “finding someone” is not actually my “can’t not do/negative energy” thing. So this meta-team needs a person who LOVES finding.

But damn, how do we bootstrap the meta-team & find a person who loves finding… before we have a person who loves finding?!

One answer: it’s okay to do things that take energy, in service of that which releases energy!

Another answer is Michael Ashcroft’s Let the others find you.

Which is what I’m doing here, & why I’m writing this as a top-level thread not just a little reply to Andy. This is a beacon. Want to work with people doing whatever most deeply energizes you? Join us!…

This has been exhilarating & thrilling to write, as it’s the 1st time I’m articulating publicly to the biggest vision I currently have that’s motivating me, which is a rich network of people who can do this synergic thing really effectively & smoothly, & train others to. 🤩”

Malcolm also runs Complice, a software company that “helps people stay in touch with their big-picture goals on a day-to-day basis, and act strategically & improvisationally”

  • Instead of productivity, we focus on intentionality

    • choosing & doing, over organizing

    • aliveness, instead of exhaustiveness

    • goals as fundamental, rather than tasks

    • proactive, rather than reactive

Have you noticed? Productivity systems go stale. You feel like you're in control for a bit, but it turns out the more you do, the more there is to do—you can never really get on top of it. To-do lists pile up, and become less and less relevant to your actual high-value next actions, which makes you not want to use your lists because the tasks are mostly garbage. Meanwhile, it's hard to remember what you're actually trying to accomplish.

Our conversation was wide-ranging and it was great fun to talk to someone that doesn’t shy away from hard questions and is humble about where we might find some of the answers. We will be instituting some of the key learning from our discussion with Malcolm moving forward.

Below are timestamps of the conversation to skip around (or just clear your mind and press play to hear a thoughtful conversation).

We thank Malcolm for their time, research, and eclectic mind. Enjoy the conversation, and until next time - Ad Astra!


  • Donella Meadow’s ‘Dancing & Thinking’ with systems (04:30)

  • Full Fractal Buy-In (11:27)

  • Key learnings from traveling, working remote, and being in movement (18:00)

  • ‘Trust dancing’ with others (23:00)

  • Concessions, compromises, and feeling understood (33:00)

  • Creating & running Complice - “the to-do list that never goes stale” (38:00)

  • Complice keeps your long-term goals fresh and tied to your feelings (47:15)

  • “Weirder Questions” from Twitter mutual @SissiPhys (53:40)

  • What is Malcolm not very good at? (01:01:30)

  • Malcolm’s response to the “Overview Effect” question (01:07:52)

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Nicholas McCay