May 2026 Planning Tips and Resources

I mentioned to Steve the other day that I wasn't really feeling April as a “start” as much as an “end” of a phase — and that it's been this week, on the cusp of May, that I've really felt the shift.

So I've been thinking the last several days that I'm going to experiment with shifting from quarters to “semesters,” because May-August feels more in line with my seasonal energy than the April-June/July-September structure does.

For some of us, three semesters per year might feel more right and rooted than four quarters or even the four seasons. Especially because those calendar quarters and natural seasons don't always align with each other.

That feeling of rightness might also align with patterns from childhood where our school years were structured much the same way. Two “in-school” semesters, Fall and Winter, and then the Summer semester off for holidays, vacations, and so on.

If you're like me, you might be feeling a stronger pull towards something now than you were a month ago. That might be a pull towards rest, relaxation, and a summer slow, or the warmer temps might be providing a spike in energy, creating momentum rather than slowing it.

Depending where you live, May might also be a time when you really feel the seasonal change and a corresponding energetic shift, just like I am right now. It was a long, cold, and gray winter here in Vienna — the worst in 30 years I've been told. April has been the transition into spring, but as it tends to do here, there has been a fair amount of sunny false starts and cold and rainy fall backs.

This last week of the month, though, has been stunning. I finally believe nature is ready for a resurgence, and so am I. I'm feeling a creative energy I haven't had since, well, this time last year, and if history repeats itself that should last into August.

So if you're feeling less attuned with the quarterly cadence, here's your permission to experiment with something else that better aligns with your own energy and rhythms.

Regardless of what cadence you prefer, May is a great time to plan for what you will and won't do during the summer “semester,” as well as a great time to wrap up any projects you can before changes in energy, focus, schedules, and capacity affect what you and your team are able to accomplish in the next four months.

~Maghan

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

• Leadership Strategy Session (LSS): Wednesday, May 13, 2026, at 11:00 am PDT
  May's Focus: Getting Your Team Ahead of the Seasonal Shift

  April gave your team some clarity about what to carry forward. Now comes the harder part: holding that clarity before everyone's rhythms start to diverge. The leaders who navigate this well get ahead of it. They read where their team's energy actually is, clarify who owns what while everyone is still present, and set clear expectations before the wobble sets in.

• Monthly Momentum Call (MMC): Wednesday, May 20, 2026, at 11:00 am PDT
  May's Focus: Make the Seasonal Shift Work for You

  May is where you start to feel it: the rhythm that carried you through spring begins to change. Your energy shifts, your schedule starts filling differently, and the months ahead start to look and feel unlike the ones behind you. Knowing your own seasonal patterns and planning around them before the season fully arrives can make all the difference in how well you navigate the shift.

The Momentum Planners were built to keep your most important work front and center. Download the free version of our May planners to help you determine what projects you want to accomplish in the new 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.