Practical answers on organisation, chaos days, weekly planning, and values

Executive overview

Disorganised people can't opt out of organising their work — but they can shape their work to demand less of it. Chaotic days aren't a failure of time blocking; they require a specific method to stay functional. Values aren't discovered once; they're a living document refined through input, reflection, and collision with reality.

The goal in all cases is intention, not perfection — about your hour, your day, or your life.

Natural disorganisation and how to adapt

• Some people are wired to feel discomfort around disorder; this makes organisation self-reinforcing.
• ADHD and similar traits can actively push against organisation — this is a real, not a character, difference.
• Disorganisation does not excuse skipping the three essentials: get tasks off your mind into a trusted system, be intentional about your time, essentialize your commitments.
• Skipping these always produces worse outcomes — more stress, lower output — regardless of natural wiring.
• The cost is higher for naturally disorganised people, but the return is still positive.
• Adapt by choosing work with fewer parallel demands: fewer large projects over many small ones, minimal logistics, offloaded shallow work.
• If you're a founder or executive, a chief of staff or assistant is worth the cost to absorb administrative load.

The chaos day method

• Many roles — litigators, startup CEOs — face days that get fully redirected by unpredictable events.
• Front-load the day: identify and complete critical tasks early, before crises build momentum.
• When the day goes off the rails, do not rebuild a detailed time block plan — you can't predict what comes next.
• Instead, identify the two or three things that must still happen today regardless. Mark these with a star in your plan.
• When you reach a starred block, stop everything else and complete it.
• Leave the rest of the schedule open; accept you'll be reactive.
• At day's end, run a longer shutdown routine: capture new obligations, reschedule displaced work, update task boards and your weekly plan.
• The goal is to tamp down chaos before shutdown so your brain is not chaotic overnight.

Weekly planning: what goes in and why

• The weekly plan bridges the strategic (quarterly/semester vision) and the tactical (today's time blocks).
• Three core inputs: big rocks from your strategic plan, key deadlines surfaced from your calendar, and custom productivity heuristics for that week.
• Heuristics example: "First hour every morning on the book chapter" or "30 minutes at lunch for office-move tasks."
• Digital vs. handwritten is a matter of taste — handwriting suits commuters and people who change their plan rarely; digital suits heavy revisers.
• Whatever the medium, build the weekly plan every week — omitting it severs the connection between vision and daily action.

Connection vs. conversation in friendships

• Connection — texts, WhatsApp, social media comments — is informative but your brain does not register it as real social interaction.
• Conversation requires analog richness (voice, body language) and non-trivial sacrifice of time and attention.
• Only conversation maintains a relationship in the way the brain actually recognises.
• Connection is useful for logistics (coordinating meetups, sharing information) but cannot substitute for conversation.
• Rebuild your social life around scheduling regular in-person or voice conversation with the people you care about.
• Use digital connection as logistical scaffolding, not as the main event.
• If you find you don't want to invest the time to actually meet someone, that's useful signal about the relationship.

Developing a personal values document

• Treat your values document as a working draft, not a permanent declaration — pressure to get it "right" once prevents you from starting.
• Values evolve fast after major life events (children, career shifts) and settle during steady periods; both are normal.
• Two requirements: regular input from external sources, and regular time for solitary reflection.
• Input sources: philosophy (e.g. Stoicism), theology, biography, documentary — anything that personifies or grapples with values.
• For theology especially, insight comes through doing the prescribed actions, not just studying texts; action generates friction, friction generates intuition.
• In reflection, notice what resonates and what repels — both are informative. Anti-values (things that make your blood boil) often point to what you actually care about.
• Write down what resonates, articulate why, and cross-reference with times you've felt proud or ashamed and people you admire or don't.
• Values feed your professional or life vision; the vision feeds your quarterly plan; the plan collides with reality and forces iteration.
• The aim is not a perfect static document but ongoing intention about how you're living, directed toward what generates moral resonance.