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How to ThinkIn the Age of AI

Run old and new tools in parallel for 2-4 weeks during…

When migrating tools, run both systems in parallel for 2-4 weeks with new data going to the new tool and old data accessed from the old tool, ending only when the parallel period confirms the new tool handles your daily needs.

When This Fires

Common Failure Mode

Day-one cutover: "I'm switching to Obsidian today! Goodbye Notion!" Week 2: "Wait, I need the database views Obsidian doesn't have." You've already stopped using Notion, broken your workflows, and now face either adapting to the gap or a painful reverse migration.

The Protocol

(1) After completing Test migration before committing's import test, begin the parallel period. (2) Route all new data to the new tool. Create new notes, capture new tasks, start new projects in the new system. (3) Continue accessing old data from the old tool. Don't migrate everything at once — read from old, write to new. (4) During the parallel period, note any friction: "I can't do X in the new tool," "The workflow for Y is significantly slower," "Z feature is missing." (5) After 2-4 weeks, evaluate: can the new tool handle 100% of your daily needs? If yes → decommission the old tool, begin archival data migration (Migrate active working set (last 90 days) first and verify…). If no → either accept the trade-offs, find workarounds, or abort the migration and stay with the old tool. A clear-eyed abort is better than a forced commitment to an inadequate tool.