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

Free subscribers: now might also be a great time for you to give our paid subscription a try. $10 a month will get you all these resources, our two monthly calls, the full digital suite of Momentum Planners, and more. Cancel anytime.

Mark your calendars for our October events, open to our paid subscribers:

• Leadership Strategy Session (LSS): Wednesday, October 1, 2025, at 11:00 am PDT
  Protecting What Matters Most

  October is peak execution season. The post-summer clarity is real, but so is the overload. Everyone wants one last big push. Everything feels important. Energy is high, but attention is stretched. This session is about protecting your team's focus, not just their output. October rewards clear-eyed leadership. The work isn't just doing — it's also deciding what not to carry into the final sprint.

• Monthly Momentum Call (MMC): Wednesday, October 15, 2025, at 11:00 am PDT
  From Energy to Impact

  October's energy is intoxicating — but when everyone knows it's the last full working month before the holidays, that energy gets weaponized into artificial urgency. October is your moment to prove that strategic focus beats seasonal panic. What you protect now determines whether you finish the year with accomplishment or exhaustion.

The Momentum Planners were built to keep your most important work front and center. Download the free version of our October planners to help you determine what actions and ideas are serving you, and which need a retool going into the second half of the year.

Paid subscribers can access the full suite of dated planners below. 👇 If you don't see them, please make sure you're logged in to your paid account.

If you don't have a paid subscription yet, now's a great time to upgrade.