Rules
1,053 rules · page 19 of 22
Start project estimates with reference class forecasting…
Begin project estimates with reference class forecasting from 3-5 comparable past projects before considering project-specific details, as base rates predict outcomes more accurately than inside-view planning.
5-15 minute pre-mortem before committing to any project…
Before committing to any significant project plan, conduct a 5-15 minute pre-mortem by assuming failure has occurred and listing 3-5 specific failure causes to surface risks that forward-looking analysis systematically misses.
Calibrate your personal do-it-now threshold
Calibrate your personal two-minute threshold by comparing management overhead (processing, organizing, reviewing, re-engaging) against execution time for 10 recent tasks—set threshold where overhead equals execution cost.
Flex your dispatch threshold with context
During meeting-heavy days with fragmented administrative windows, lower your dispatch threshold to ~1 minute; during dedicated administrative blocks, raise it to ~5 minutes to match available processing capacity.
Batch tasks by cognitive context…
When batching similar tasks, group by cognitive context type (communication, financial, scheduling) rather than by chronological arrival order to minimize context-switching overhead.
Four-element meeting gate
Before starting any meeting, verify that four structural elements exist: stated purpose (what decision/problem), timed agenda with allocations, hard stop time, and defined outputs—if any element is missing, either add it or cancel the meeting.
Open meetings with 15-20 minutes of silent reading…
Distribute pre-read documents before meetings and open with 15-20 minutes of silent reading to ensure all participants enter discussion with identical context, eliminating the information-transfer phase that consumes the first half of unprepared meetings.
Cap decision meetings at 6-8 people — communication…
Limit meeting attendance to 6-8 people maximum to prevent communication complexity from scaling combinatorially (n(n-1)/2 conversational pairs) and social cost from suppressing genuine discussion.
Compress meetings into contiguous blocks on designated…
Compress meeting schedules into contiguous blocks on designated days rather than distributing them evenly across the week to preserve multi-hour maker time blocks on remaining days.
Replace status-update meetings with async written updates…
Replace recurring status update meetings with asynchronous written updates unless the meeting serves an additional coordination function beyond information transfer.
Block recovered time for priority work immediately…
Immediately block recovered time on your calendar for specific priority work before recovering it—recovery without preallocation creates a vacuum that entropy fills with new low-value activities within weeks.
Use AI to analyze routine execution logs…
Use AI to analyze routine execution logs across multiple cycles, identifying which deviations correlate with missed executions, to diagnose structural fragility points invisible from inside the experience.
When one routine element fails, execute minimum viable…
When a single element of your routine fails, execute the minimum viable versions of remaining load-bearing elements rather than abandoning the entire routine structure.
Classify routine elements as load-bearing…
Classify each routine element as load-bearing (removing it degrades output or wellbeing) or cosmetic (preferred but not essential) to distinguish what must survive disruption from what can be sacrificed.
Commit 7-8 hours when you have 10 available — leave 2-3…
Plan for seven to eight hours of committed work when you have ten productive hours available, leaving two to three hours as unallocated slack to absorb disruptions without cascade failures.
Audit the past 12 months of calendar data — rate each…
Conduct seasonal time audits by pulling calendar data from the previous twelve months and rating each month as low-demand, baseline, high-demand, or crisis to identify recurring annual patterns.
Make at least one structural adjustment before each…
For each identified high-demand period, make at least one structural adjustment before the period arrives by pushing deadlines, reducing project count, or front-loading preparation during preceding calm periods.
Schedule recovery proportional to intensity immediately…
Schedule recovery time proportional to the intensity and duration of each high-demand period immediately after the period ends, as a structural calendar commitment rather than a vague intention.
Forecast high-demand capacity from last year's same-period…
Use reference class forecasting from last year's actual capacity during the same seasonal period rather than estimating from your current state when planning high-demand periods.
Reduce commitments ~30% during high-demand months vs…
Reduce project commitments by approximately thirty percent during months you have identified as high-demand compared to baseline months, based on your measured capacity data.
Open weekly planning by reviewing plan vs. actuals…
Begin each weekly planning session by reviewing the previous week's plan against actual outcomes, identifying the single biggest gap between intention and reality without judgment.
Process inboxes sequentially top-to-bottom, never…
When processing any recurring information inbox, work sequentially from top to bottom rather than cherry-picking items, to prevent repeatedly skipping difficult decisions that form the 'maybe pile'.
Title reference items with the words your future self…
For any reference item you store, write the title using the words your future self will search for when they need it, not the words that categorize what it is.
Separate reference material (static lookup) from working…
Separate reference material (static information for lookup) from working notes (evolving thinking) into distinct systems, as mixing them corrupts both retrieval and development.
Route actionable items to your task system and reference…
Route actionable information to a task management system and reference information to a separate reference system, never mixing the two in the same storage location.
Capture actions as specific next physical steps…
Capture every action item with a specific next physical action (not 'handle client project' but 'email Sarah the revised timeline') to eliminate re-processing friction at execution time.
Organize actions by execution context…
Organize action items by context of execution (@computer, @phone, @errands) rather than by project, because you execute tasks based on where you are and what tools you have available.
Keep a Waiting For list with delegation date and expected…
Maintain a separate Waiting For list tracking items delegated to others with delegation date and expected completion date, reviewing it weekly to follow up on overdue items.
Triage before processing
Perform information triage by spending no more than 3 minutes scanning the full landscape of waiting items before processing any single item, sorting into urgent-high-value, high-value-not-urgent, low-value, and discard categories.
During triage, scan surface indicators only — opening…
During triage, scan subject lines and senders without opening items or reading full content, because reading during triage collapses sorting into reactive processing.
Every ~500 words, close the source and write the core idea…
After reading any segment of approximately 500 words, close the source and write 1-3 sentences capturing the core idea in your own words before continuing.
Every new permanent note must link to at least one…
Every new permanent note must link to at least one existing note in your system, forcing you to identify relationships at the moment of creation rather than deferring connection to future review.
Write permanent notes for your six-months-from-now self…
Write each permanent note to be comprehensible to your future self six months from now without access to the source, eliminating context-dependent shorthand and 'see above' references.
One atomic fact per spaced repetition card, answer under…
Create spaced repetition cards testing exactly one atomic fact per card with answers under one sentence, because cards testing multiple components produce vague retrieval that the algorithm cannot accurately schedule.
Add 5-10 new cards per day in a mature SRS — this pace…
Add 5-10 new spaced repetition cards per day when maintaining a mature system, as this moderate pace produces a daily review load of 50-100 cards taking 10-15 minutes.
Create SRS cards only for information you already…
Create spaced repetition cards only for information you have already understood through processing, not for definitions you cannot explain, because memorization without comprehension produces brittle unusable memory.
Tag time-sensitive information with explicit expiration…
Assign explicit expiration dates to time-sensitive information at the moment of capture using the format 'expires:YYYY-MM-DD' or equivalent, rather than attempting to remember which items are time-bound.
When uncertain about lifespan, expire at 3 months not 1…
Err toward shorter expiration windows when uncertain about information lifespan, setting expiration at 3 months if unsure rather than 1 year, because expired items can be renewed while accumulated stale information cannot be easily detected.
Monthly expiration sweep
Conduct monthly expiration sweeps reviewing all items whose expiration dates have passed and either archive/delete if expired or renew with new expiration date if still relevant.
Mark genuinely timeless material as evergreen/no-expiry…
Mark genuinely timeless material (principles, frameworks, mental models valid for decades) as 'evergreen' or 'no-expiry' rather than assigning artificial expiration dates that create unnecessary maintenance.
Four expiration categories at capture
Classify information into four expiration categories at capture time: expires within 1 week, 1-6 months, 1-5 years, or evergreen, to standardize expiration decisions and reduce cognitive load.
Evaluate search results by reading only…
When search returns results from your information system, evaluate each candidate by reading only the bolded or highlighted passages from progressive summarization rather than scanning full text.
Title notes with the natural-language words you'd search…
Write note titles using the natural-language words you would type when searching for that information, not abstract labels or jargon, to maximize searchability.
Flatten folders with fewer than 5 items — move contents up…
Flatten folder hierarchies by moving contents of folders containing fewer than 5 items up one level, as such folders are structural overhead with minimal retrieval benefit.
Bold 10-20% of a note's text on first revisit — select…
Bold 10-20% of a note's text on first revisit by selecting only passages that capture core ideas, making subsequent scans 5-10x faster than reading full text.
Highlight 10-20% of bolded passages on subsequent revisits…
From bolded passages, highlight 10-20% that are most relevant to your current purpose on subsequent revisits, creating a second layer of compression targeted to your active needs.
Write a 3-5 sentence executive summary at the top…
Write an executive summary of 3-5 sentences at the top of a note only after it has been revisited 3-4 times, as this frequency indicates the note has proven its importance through actual use.
Progressive summarization is just-in-time only — apply…
Apply progressive summarization layers only to notes you revisit for specific purposes, never in batch processing sessions, to ensure layers reflect actual utility rather than speculative importance.