Tooling and Habits for Maximum Productivity

Key Narrative

Productivity advice is mostly noise. But after years of experimentation—and running a company where output matters—I’ve converged on a small set of tools and habits that genuinely work. This post is the distillation: what to use, how to use it, and why most productivity systems fail.

The core insight: productivity is not about doing more things. It’s about doing the right things with sufficient depth. Most systems optimize for the former; the best optimize for the latter.

Outline

I. Introduction: The Productivity Trap

• The allure of systems and tools
• Why most productivity advice fails
• The real goal: important work, completed

II. Foundational Principles

A. Protect Deep Work

• Cal Newport’s framework, applied
• The 3-4 hour morning block
• What counts as deep work (and what doesn’t)

B. Reduce Decisions

• Decision fatigue is real
• Routines as decision elimination
• The power of defaults

C. Create Forcing Functions

• Deadlines, commitments, stakes
• Public accountability
• The value of constraints

D. Measure What Matters

• Track outcomes, not inputs
• Weekly reviews (actually useful)
• The danger of vanity metrics

III. The Tool Stack

A. Task Management: Plain Text

• Why I abandoned complex systems
• A single text file, daily
• The “one thing” principle
• Format: date, three priorities, notes

B. Calendar: Time Blocking

• Calendar as architecture of the day
• Deep work blocks (protected)
• Batch meetings (afternoons)
• Buffer time (underrated)

C. Notes: For Thinking, Not Storage

• Writing to think, not to remember
• One note per topic, heavily edited
• The Zettelkasten idea, simplified
• Tool: Obsidian (or any plain text)

D. Reading: Deliberate Intake

• RSS for curation (Feedbin)
• Instapaper for processing
• Kindle for books
• The “no news” rule

E. Communication: Async by Default

• Email: batched twice daily
• Slack/Teams: specific windows
• Phone: almost never
• The cost of synchronous communication

F. Writing: Focused Tools

• iA Writer for prose
• The value of distraction-free
• Version control (Git) for important documents

IV. The Habits

A. Morning Routine

• Wake time: consistent, early
• No phone for first hour
• Exercise before work
• Deep work block: 8-11am

B. Weekly Review (Actually Useful)

• What happened last week?
• What matters next week?
• What’s stuck?
• 30 minutes, Sunday evening

C. Monthly Calibration

• Are priorities still right?
• What should I stop doing?
• What’s working, what isn’t?

D. Quarterly Planning

• Objectives (few, important)
• Key results (measurable)
• OKRs for personal life, not just work

V. What I’ve Stopped Doing

A. Abandoned Tools

• Complex task managers (Omnifocus, Notion databases)
• Read-later backlogs (they grow forever)
• Time tracking (cognitive overhead > insight)

B. Abandoned Practices

• Inbox zero (satisfying but not valuable)
• Aggressive scheduling (leaves no slack)
• Multitasking (it doesn’t work)

C. Why They Failed

• Overhead exceeded value
• Optimized for wrong metric
• Didn’t match how I actually work

VI. Contextual Recommendations

A. For Executives

• Protect thinking time aggressively
• Delegate via clear writing
• Meet in batches, not scattered

B. For Individual Contributors

• Maximize deep work blocks
• Manage up with async updates
• Guard your calendar

C. For People Who Manage Both

• Split days: maker vs. manager
• Transitions are costly—batch the work type
• Write more, meet less

VII. The Meta-Lesson

• Systems should serve you, not vice versa
• Simplicity beats sophistication
• The best productivity hack: choose important work
• Consistency compounds

Suggested Sources

Books

• Cal Newport, Deep Work (foundational)
• Greg McKeown, Essentialism
• James Clear, Atomic Habits (on systems)
• David Allen, Getting Things Done (to understand, then simplify)

Essays

• Paul Graham, “Maker’s Schedule, Manager’s Schedule”
• Sam Altman on productivity
• Patrick Collison’s advice on fast execution

Research

• Daniel Kahneman on cognitive load
• Studies on context switching costs
• Research on decision fatigue

Tools Referenced

• Obsidian (notes)
• Feedbin (RSS)
• iA Writer (writing)
• Fantastical (calendar)
• Linear (task management for teams)