October 2025 Planning Tips and Resources
October is the last clean shot at big, collaborative projects this year. Not in a panic-inducing way, but in a “let’s be real about what’s possible” way.
Here’s what we know: if a major initiative isn’t already in motion, it’s unlikely to find its groove before the winter holidays start their game of calendar Tetris. Teams scatter. Focus fragments. And suddenly that “definitely finishing this year” project becomes next year’s tar pit project.
But October still has legs. Your team’s mostly present. The post-summer rhythm has settled. There’s enough runway to actually land something meaningful instead of just shuffling it around until December makes the decision for you.
The trick is being honest about what’s actually in play versus what’s wishful thinking.
If your collaborative projects or solo big projects aren’t at least halfway done by Halloween, November’s pre-holiday weeks are going to feel less like progress and more like channeling a lot of Dunkirk Spirit to finish things up. Better to make the call now about what’s really going to cross the finish line.
The resources below can help you sort the real from the hopeful and protect you and your team’s sanity in the process.
~Charlie
Resources for Deciding Which ProjectsKey to channeling October’s energy is selecting those projects you’re really going to push forward. These resources might help you make those...



