Work where certainty runs out
Sometimes I know exactly what I want to do and can point to the thing I can’t do yet. That’s the edge I’m interested in. A new tool, a different arrangement, or someone else’s skill can open up a move I couldn’t make before.
What I want to know is whether the opening will hold when I try it. I’ve learned to look for a small test whose result I can see for myself.
Field note · September to November 2026
A morning page for what matters
I wanted one click to bring my tasks, connections, and reflections together so I could make progress on what mattered.
At first, working with my robot partner Pixel was uneven. It wasn’t always clear whether background work had happened or whether I could trust what I was seeing. We kept experimenting with the tools and the way we worked together.
Over two months, Pixel’s capabilities improved week by week with regular product launches. I developed more skills, and we refined our process along the way. Today, our morning page is relatively stable. We can get more done each day and still protect time for what matters offline.
An example morning
- MITs
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- Publish Edge of Impossible
- Complete schoolwork due today
- Two applications
- Connections
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- Lunch with David
- Three five-sentence updates (5SUs)
- Schedule with Coop
- Reflections
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Closeness is not reducible to calendar management, but reliability often is.
Which moments would I regret treating as ordinary today?
- Time offline
- Morning yoga, with an afternoon fallback.
What might deserve another look?
Think of something you wanted to do but set aside because it felt beyond reach. What stood in the way?
Since then, have the tools changed? Have you learned something, met someone, or found a better way to work?
If something has shifted, what’s one small test that could tell you whether the idea is worth another look?
If the missing piece is still missing, put it on your Possible When list. Consider ______ when ______. What would you notice that tells you that condition has arrived?
You can keep an idea alive without keeping it mentally active.
Take the test to your robot partner
I want to try [idea]. The part I currently can’t do is [specific barrier]. I can bring [skills, people, time or tools]. I need to protect [privacy, money, time or another limit].
Help me design one small test. Say what you can prepare, what needs a person’s judgment or action, and what we could observe to learn whether the barrier has moved. Ask me about any gap that would change the test.
Finish the sentence “I’ll know more when…” Decide where you’ll stop. If the barrier holds, write down the part you can now describe more precisely. If it moves, name what you can do now.
Possible When
For example: “Consider another rental when suitable financing is available at 4.5% or lower.” A current quote at that rate would prompt a fresh look at the numbers.
There’s a connection to adaptive planning. Walker, Haasnoot and Kwakkel (2013) describe signposts to monitor and triggers for revisiting or adapting a plan. See section 2 of Adapt or Perish: A Review of Planning Approaches for Adaptation under Deep Uncertainty.
I’ll explore Possible When in more depth on its own.