A Weekly Routine for Long-Term Judgment

Core principles (keep these in mind)

• Judgment improves through reflection + feedback, not volume

• Fewer inputs, deeper processing

• Regular time spent in future horizons

• Writing > thinking silently

This routine takes ~6–8 hours/week total.

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1. One “slow input” session (90 minutes)

Once per week

Purpose: train pattern recognition across time.

What to read

Choose one:

• History (technology transitions, institutions, empires)

• Philosophy (ethics, responsibility, power)

• Systems thinking

• A deep AI governance or safety essay

Not news. Not tutorials. Not hot takes.

How to read

• No multitasking

• Take handwritten or digital notes

• Pause when something feels uncomfortable or surprising

Capture (5–10 minutes)

Write:

• “What is the author really warning about?”

• “What patterns repeat across time?”

• “What would break this argument?”

This trains second-order thinking.

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2. One “future horizon” block (60 minutes)

Once per week

Purpose: force your mind beyond the present.

Structure (simple but powerful)

Split the hour into three 20-minute segments:

• 5-year horizon:
  What is likely to change soon? What assumptions might fail?

• 15-year horizon:
  What capabilities, institutions, or norms might emerge or erode?

• 30+ year horizon:
  What values must be preserved no matter what?

You don’t need answers — you’re training the muscle.

Write bullet points. No polish.

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3. One “error log” review (30 minutes)

Once per week

Purpose: learn faster than others.

What to do

Review:

• Predictions you made

• Beliefs you held strongly

• Decisions that didn’t work out

Write:

• What did I miss?

• Which incentives fooled me?

• Was I overconfident or underinformed?

This builds epistemic humility, a core trait of good judgment.

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4. One “sense-making output” (60–90 minutes)

Once per week

Purpose: convert thinking into clarity.

Choose one:

• A 300–600 word note

• A diagram

• A letter to yourself

• An explanation for a non-expert

Topic:

• Something confusing

• Something over-hyped

• A tradeoff people ignore

Do not publish unless you want to.
This is about thinking clearly, not branding.

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5. One conversation with a time-rich thinker (30–60 minutes)

Once per week or biweekly

Purpose: calibrate judgment socially.

Choose someone who:

• Is calm, not reactive

• Disagrees thoughtfully

• Has lived through cycles

Ask:

• “What do you think people are missing right now?”

• “What did you get wrong earlier in your career?”

• “What would you bet against?”

This helps break intellectual echo chambers.

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6. Daily micro-habits (10–15 min/day)

Morning (5 min)

Ask:

“What matters even if today goes badly?”

Keeps perspective.

Evening (5–10 min)

Write one line:

• “What did I notice today that others might miss?”

This trains attention.

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A minimal version (busy weeks)

If you only do two things, do these:

1. One slow reading session

2. One short weekly written reflection

Consistency beats intensity.

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Signals it’s working

After 3–6 months, you should notice:

• Less reactivity to news

• Better detection of hype

• Comfort saying “I don’t know”

• Improved ability to explain tradeoffs

• Stronger intuition about second-order effects

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A final reframing

Long-term judgment is not about predicting the future.
It’s about becoming the kind of person who:

• Notices early

• Thinks clearly under uncertainty

• Acts without panic

• Preserves options

That is an extremely rare and valuable skill.