#you can correct a poorly-executed dance MUCH more easily than you can come up with a whole minute of choreography in a week

[gingerbreadmonsters]

im so excited for ballet today SO excited 🥳🥳🥳

[andymatuschak]

Satisfaction and progress in open-ended work

When we’re in execution mode, we swim in signs of our progress. A day’s work stands crisply in some endless checklist: four problems solved; three features added; check and check. Am I on track? Did I have a good day? Typical productivity advice applies: set goals; track progress; triage tasks. A checklist makes the day’s grade clear enough.

Working in this mode, it’s easy to feel satisfied at the end of a good day’s work… and (at least for me!) impossible to feel satisfied reflecting on a good year’s work.

Yes, all those tasks got checked off, but if you can easily reduce the work to a checklist, how groundbreaking can it be?

For more open-ended problems, much of the challenge lies in figuring out what to do next. These rich questions offer deep satisfaction on longer time scales, but without a clear sense of progress, each day ends ambiguously. Was today good? Will these tinkerings add up to anything? In what timeframe? Who knows. Ultimately: what structures around progress, self-correction, and operations can help us in open-ended mode?

These questions are intensely personal, but I hope that notes from my journey here may help your own.

Deontology and open-ended work

Creative disciplines from painting to research offer one fairly consistent piece of advice: butt in chair.

This advice usually emphasizes performing actions, since checklist-style productivity advice about achieving objectives applies poorly to open-ended domains. A novelist might begin their day by setting an action-oriented goal to write 1,500 words in a day, or to complete eight uninterrupted half-hour periods. An achievement-oriented goal like “finish writing a chapter,” would be too coarse to be helpful. To break down that goal further would itself require open-ended work.

I started here, journaling my daily time-on-task in pursuit of “deep work.” That structure can become an actionable checklist: e.g. “sketch for three hours from my earlier brainstormed mind map.” Longer focused working periods did help me accomplish more, but I still felt uneasy about the macro-level questions I’d been asking.

For instance, I often felt in hindsight that I’d spent those hours focused on the wrong things—and the vague sense that I could have known as much in advance. More worrying: those journaled hours said nothing about progress towards my true goals.

If I were to repeat my day, should I have sketched for three hours? Should I have sketched those ideas for three hours? Should I have sketched using some other method? Given the progress I’ve been making, should I continue down this path tomorrow or try some other route?

These questions aren’t directly answerable… but that doesn’t mean we should ignore them completely.

There’s an analogue here to deontological ethics, in which actions form one’s moral basis, not consequences. For example, some of deontology’s adherents would argue that a lie is never justifiable, no matter the consequences. Rightness comes from telling the truth because that’s what enacts an individual’s moral imperative.

Action-oriented “butt-in-chair” advice, taken too literally, has a similar bent: a focused creative session is a great outcome, even if all the work has to be thrown out at the end of the day. Success comes from focused work because that’s what enacts an individual’s creative imperative.

Yes, that discarded work often kindles the next day’s brilliant ideas, in the same way that truthfulness in the face of nasty consequences often leads to great outcomes. But that’s not always so; some discarded work is better than others; some sticky situations admit more truth than others.

We’d like to be able to tell the difference. Just as we must seek a more fluid ground in ethics (neither pure deontology nor pure consequentialism), we need more fluid approaches for our open-ended work.

Considering consequences

In open-ended work, goals around a single day’s outputs are misleading or ambiguous, but goals over weeks and months are more concrete.

A graduate student may not know exactly what to do on a given day, but they know that their thesis is due in six months. An artist may not know what to do on a given day, but they might know they’d like to have a gallery show by the end of the year.

Medium-term achievement-oriented goals can support error correction and provide feedback to action-oriented day-by-day goals.

For instance, say that I’ve been checking off “sketch for three hours”-type tasks every day for two weeks. I can reflect on the progress I’ve made in hindsight and compare it to my hopes for the following month. If I’d hoped to try a prototype in classrooms before the school year ends, and my sketches aren’t yet converging on a single idea, I might shift the focus of my creative work to depth over breadth. On the next day, I might choose my five favorite concepts, then set action-oriented goals around making them higher-fidelity.

If I’ve not generated many ideas despite endless diligent hours in the chair, I might shake up my methods, limiting myself to ten minutes per idea, or only allowing straight lines, or trying a different medium. If that doesn’t work, it might indicate I’ve reached an idea cul-de-sac. Time to backtrack.

This kind of planning-oriented thought can crush a more expansive, ideating mindset.

In the middle of my sketching hours, I don’t want to be worrying about whether I’ll be ready for my classroom prototype next month. Within a given day, action-oriented “butt-in-chair”-style advice does help; meta-thought is just distracting. But go too long without error correction, and you’ll misspend hours in the chair. Some separation is in order.

My current practice

I’ll outline my current approach now. It’s young and evolving, but I certainly wish I’d been able to read this a few years ago, so perhaps it will help some readers.

I begin each day by selecting some action-oriented goals which I hope will advance some broader achievement-oriented goal. For example, if I’m working towards an in-classroom prototype around a set of ideas, I might aim to spend three focused hours fleshing those ideas out in sketches.

This is a natural spot for brief deliberation, but once the day begins, I focus on the actions I’ve chosen and suppress planning. The rest of the day’s work becomes roughly deontological. I give myself permission to be satisfied with the day if I spent three focused hours sketching like I’d planned.

Weekly, I reflect on the previous week’s mix of actions and my progress towards the broader goal. I consider what’s working and what’s not, then I make a few notes about how I’d like to adjust my daily mix of actions in the next week.

I always assign some target date to that broader goal (“run a prototype in classrooms by June 1”). My weekly reflection pushes on that date: does it need to move? Does my daily work need to change focus to hit it? These higher-level reflections help me feel a sense of progress (or note a lack of one), and their regular course corrections give me the safety to draw satisfaction day-to-day from ambiguous, action-oriented goals.

Monthly, and when completing a broader achievement-oriented goal, I reflect on the bigger picture which defines my goals. That roadmap invariably evolves as my work proceeds, but maintaining that long-term plan helps me connect my present work to downstream goals. Those connections themselves inspire satisfaction: they help me see a path to my true goals.

For this level of reflection, I’ve found it helpful to reference others’ related roadmaps. For example, here’s IDEO’s product design process; my design partner May-Li Khoe uses a similar process of her own devising. Every field has dozens of competing structures like this, but their underlying similarities can provide useful scaffolding.

From time to time, I flip back into execution mode. It feels like an old friend. We say hello, dance for a while, and part ways smiling, just as it always was.

Open-ended mode is more enigmatic, reserved—yet occasionally it sparks some moment so singular it lights up the whole year. Those moments don’t happen without the days spent together between those moments. I’m slowly learning to make the most of our quiet strolls.