September Reflections
The Ideal Time for Reflection and Planning
Though it may be more traditional to think of late year to early the following year as being the season for planning and reflection, I'd argue that September is the sweet spot. That bridge between the seasons of Summer and Fall, when nature is shifting gears.
Here in Texas, mid-August is when the kids go back to school, and September is the month when things start to feel quiet again. When you start to get a little free time back to yourself.
It is also the last month before the last quarter of the year. For those who work in an industry with a 90-day sales cycle, normally you know in September, based on your current pipeline, what your end of year revenue will be and can start forecasting for the next year.
Even for those without this business cadence, three months or so often feels like the minimum amount of time to navigate a transition. If you are looking to make a change in the new year, it can’t hurt to get a head start.
Thus, in many ways, September is a perfect time to shut the book on one year and move on to the next. If you are like me, you may even find yourself starting to write 2026 next to the date in some of your journal entries.
Prepare to Be Present
I’ll admit, it's an interesting balance being prepared for the year to come, organizing your calendar and such for the next quarter, even the next two quarters, while also remaining present and enjoying the now.
What I have found is that my ability to enjoy "the now" is also enhanced somewhat by my willingness to have planned it 3-6 months ago. While these days I leave a lot of time open on my calendar, I also find a sense of comfort when the main events are anchored early on.
For example, pencilling in all my kiddo’s school closure dates, campus events, and volunteer opportunities for the next nine months - both digitally and on paper - the week the school shared the schedule, resulted in an immediate sense of feeling grounded - anchored around one of our family’s priorities.
Blocking time for reflection and planning are also at the top of the list of priorities of space I protect on my calendar. To have a successful year, this time is non-negotiable.
So much of the unease experienced by my clients comes from when they aren’t able to feel present in the moment. When they're worried about what to do and what's left to do. Usually, that is a list of “should”s or “could”s. When they aren’t certain that where they are spending time is a priority, they start spinning. The chaos stops once they have clarity. And that clarity surfaces through a regular cadence of planning and reflection.
A regular cadence of annual, quarterly, monthly, and weekly reflection and/or planning is essential preparation to feel present in the moment.
This special time can often feel like “me time”, which makes it harder for some people to protect. You can fuel permission and motivation to guard and execute by blocking it in the calendar early on. As other obligations start to arise, being able to see distinct windows of opportunity for planning - when they are open and when they start to close - can light a fire under those reluctant to allow themselves this space.
The Rhythm and Reason
Over the years though, I have found a rhythm of reflection that works best for me. It’s something of a personal practice which I weave into my own calendar as well as my consulting.
As part of the rhythm, I do this month’s reflections and next month’s planning during the third week of the current month. Likewise, I perform a quarterly review toward the beginning of the last month of a quarter. And, as mentioned, next year’s planning starts around the final month of the third quarter. (I actually start reflecting towards the end of August with the goal to have a plan firmed up by mid-October.)
This rhythm developed out of an annoying tendency I have to push myself to perform until the very last minute of the very last day of each week, month, quarter, year…you name it. I attempt to eke out every last drop of productivity I can, and it’s hard for me to stop. To put my pencil down and hand in my test. I run the full race, and I run it hard. All the way to the finish line.
My guess is, you do too.
Taking time to stop and reflect earlier than seems natural is equivalent to pacing yourself for your second-to-last lap of a race so that you can go all out for the final lap.
It accomplishes a few things:
- Allows you to reflect and plan while you have the headspace, not tunnel vision to the finish line.
- Gives you peace knowing that you can give it your all for the current period while letting go of the outcome, because you’ve already made a plan for the next race.
- Grants you the freedom to lean into your own tendencies to go hard now, and see them as strengths, rather than fighting them and feeling guilty.
Reflection vs. Planning
So what does this look like?
- Reflection is taking stock of what actually happened, without judgment. It is also about:
- Picking your head up and reassessing whether you are still on course.
- Asking yourself if the course you are on is still relevant and aligned with where you want to go.
- Planning is asking questions like:
- Based on that, where do I want to go?
- What is my best next step?
Depending on where you are in life and business, one or both of these could feel especially hard. These aren't practices that necessarily come easily or naturally to us. They are cultivated over time. They take adequate space and relevant questions.
Like the idea of starting a reflection practice, or kicking yours off earlier this year? Curious about where to begin?
Let's schedule a time to chat. This may just be one of my favorite parts of coaching and consulting. There’s no wrong way, even if you aren't doing it at all. Be gentle with yourself. Awareness around what may be stopping you is also a step.
Questions for Reflection:
- Do you have any planning traditions?
- What questions do you use to review and reflect on the past year and the one to come?
- What, if anything, stops you from honoring this time?