Convos.dev 011: How To Get The Most Out Of Holiday Breaks
Dec 18, 2025
They discuss unplugging from work during holidays while keeping intentional productivity. Jess explains negotiating extended time off and structuring sabbaticals to avoid guilt. Chris shares his planning-day method with roles, big rocks, and tracking time for family. They contrast trips versus vacations and demo handy tech like email printing, ChatGPT formatting prompts, and focus tools.
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Time Off For Mental Clarity
- Use time off to pursue mental clarity, not just activity.
- Chris prioritizes clarity so he can be fully present when work resumes.
Plan By Roles And Big Rocks
- Run a planning session by listing roles, principles, and 1–2 monthly "big rocks" per role.
- Chris ties weekly tasks to those big rocks and enforces daily, weekly, and monthly review patterns.
Enforce Planning Rhythms
- Lock in repeatable patterns: daily shutdown, weekly reprocessing, and monthly mini planning days.
- Chris enforces these patterns so planning sticks instead of fading away.
