Up to a decade or two
If you're skipping more than a few years, up to a decade or two, take a session off from actual play. Instead, discuss:
- How long, exactly, are you skipping?
- Who wants to continue playing their current PC? How might they change?
- Who wants to make new PCs?
- What NPCs and setting elements should continue to be important?
- How has the setting changed?
Have anyone who wants to play a new PC create them now, picking any background that makes sense given the time skip. Do Introductions as normal, with the existing PCs each taking turns during steps 6-7 (PC connections). Pick a starting season and do the Seasons Change move. Use the result to craft a First Adventure, writing love letters to existing PCs to help fill in the skipped-over time.