My planning system

Here’s the system I use to orient myself to what’s most important, and consistently steer towards it (contra the drunken sailor step).

Once a quarter §

1. Revisit my core values, change if appropriate¹
2. Based on my values, revisit my 30-year-old definition of success, change if appropriate² (these are outcomes I want to achieve by age 30)
   • Rows = core values
   • Columns = 1) internal outcomes, 2) external outcomes³
3. Based on my definition of success, set quarterly checkpoints (outcomes) and systems (habits)⁴
4. Other things I’m experimenting with
   • Defining my why (big lofty connection back to family, friends, and desired impact)
   • Defining my 12 favorite problems
   • Creating a learning syllabus

Weekly §

1. On Sunday mornings, review my last week and plan out the upcoming week — how granular I plan will depend on how complicated the week will be (often I just plan out the big questions/pursuits I want to get to each day; this usually takes ~1 hour

Daily §

1. Shut down for the day — write down any outstanding tasks and schedule them
2. Plan the next day in detail — ideally, every minute is planned (this will undoubtedly change, but I find it useful to be this intentional); this usually takes ~10–20 minutes

Before and after each working session §

1. Before — do all my meta-thinking; i.e., set an intention (what I want to achieve) and make a plan⁵
2. After — review / celebrate what I finished and identify one moment of joy⁶

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See Multi-scale planning (Cal Newport), Motivation & drive (Huberman) and Study habits (Huberman)

Footnotes §

1. In my case, I chose 5 — vitality (mental and physical health), curiosity, courage, mastery, connection ↩

2. I’m planning to experiment with longer-term definitions of success at ages 50 and 80 ↩

3. An internal outcome is something only I can feel (e.g., “regularly excited to meet new people”) while as an external outcome manifests itself in the world (e.g., “surrounded by people who energize, challenge, and care deeply”) ↩

4. Because it’s self-defeating to focus on everything at once, I’m experimenting with prioritizing 1–2 values per quarter (I’ve heard people call this a “season”), and refining my checkpoints/systems for those, while paring down others ↩

5. While creating a scaffold at the beginning of the session can be less fun than just getting right to work, I find that I end up getting much more done, and having more fun while doing it ↩

6. I’ve been emphasizing finding joy in my work and enjoying the process rather than just trying to reach the outcome ↩