Tricky Transitions: Easing the Shift from Summer Freedom to Calendar Crunch
Main points, no filter:
✅ September smacks you in the face. Summer freedom ends, routines tighten, and suddenly your inbox is a dumpster fire.
✅ Transitions aren’t one smooth switch. They’re layered micro-shifts—and each one can knock you on your ass.
✅ ADHD makes it trickier. Switching gears isn’t just annoying, it can feel impossible for neurodivergent brains.
✅ The signs show up fast. Mood swings, forgetting stuff, and sitting in your car just to mentally gear up are all clues.
✅ You’re not broken—it’s just hard. But with planning, grace, and tools like CBT-I (sleep therapy), the chaos can actually calm down.
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Keep reading to get more details on the tricky transitions.
The Jarring Switch
It starts in August with the PSL drop at the local coffee shops and the Halloween decorations at the big box stores. It’s still hot as Hades out, but there is something lurking.
Do you hear that? It’s the calendar crunch.
From May to mid-August the office cubicle population is sparse and the unstructured summer days are lazy and free. The routines are broken up by vacations, summer camps, and flex Fridays.
🚨 Spoiler Alert 🚨 September is here and with it comes regular working hours, more people in the office more consistently, and more traffic. If you have school aged kiddos, the sports practices and extra curriculars are ramping up, so are the emails. So. Many. Emails. Talk about a tricky transition.
Why the Lazy-to-Structure Transition Feels So Hard
When we hear the word “transition” we think about the change from one thing to another. But the thing that makes transitions tricky is that there are multiple steps that often go overlooked and that are especially difficult with neurodivergent brains.
The three parts of a transition:
Phase 1: stop the current thing
Summer is over, despite what the thermometer says. The pools will close. There will be a last vacation of the season. The summer campers will go home. The summer jobs are over. Anything that can be winterized is wrapped, cleaned, and put away.
Phase 2: the gap between the old thing and the new thing
It’s still hot AF outside. There is still one three-day weekend left. The back-to-school sales, tax free shopping week, and the “are you ready for school?” conversations can be heard in the checkout lines.
Phase 3: starting the new thing
The first day back in the office or in the school building starts with an earlier than usual alarm clock. You can tell the traffic is thicker than it was a couple days ago. There are sunburned faces above the cubicle walls and open toed shoes under the desks.
Instead of one simple switch, you’re really juggling four micro-transitions—like waves knocking you down before you can stand back up.
It’s like you are greeting September with your bathing suit all out of whack and sand in places you didn’t know you had. Maybe the fall flavored latte would be just the pick-me-up you need.
It's not just the seasonal shifts
Transitions come in all shapes and sizes.
Physical transitions – moving from asleep to awake, moving from one room to another. (For more on sleep issues see Dr. Pimble’s blog)
Mental Transitions – shifting to the appropriate mindset for the environment. It’s like yelling over music that suddenly cuts off. The volume of your voice was appropriate one moment and way too loud the next.
Emotional Transitions – this is like leaving lunch with your friend to go back to work or giving yourself a pep talk to start on a chore. Once you are in it, it’s not that bad but the shift to motivate yourself can be tricky.
Signs Your Family Is Struggling with the Shift
✅ Mood in the house - if you notice tensions, anger, or tantrums leaving or coming home
✅ Slow to switch gears – I have been known to sit in the car for a minute just mentally preparing to open the door and get out
✅ Doubling back to get the thing that you need (probably more than once) when you are moving from one place to the next.
Strategies to Smooth the Transition
✅ Decide ahead of time.
what time you will plan to shift from one task to the next
what clothes you will wear
what chores/tasks/errands you will do and when
Deciding ahead of time will smooth out that in between space because you have already made the decision.
✅ Set alarms to indicate the task switch.
It is easy to go on a deep dive hyperfocus if you are engaged in something you find meaningful or interesting. Setting an alarm ahead of time will be a cue to transition to the next thing. You may need to trial and error how much time you need to transition. Some tasks may require a few minutes while some may need a little bit longer so you can wrap up the details.
✅ Anticipate that transitions will be tricky and account for that.
This means building in buffers the first week back to work after a vacation or the first week of school. Do your future self a favor and have a grocery order ready for pick up or enough freezer meals for the first week back from a trip. Read more about doing your future self a favor here.
✅ Reset your space before you leave.
If you are going out of town, this might mean that you schedule less the week ahead, so you have enough time to prepare for whatever the transition is. When you come back from your trip, you’ll be met with calm not chaos.
So now what?
Here’s the deal - transitions seem hard because they are hard — not because you’re doing it wrong. Give your family time to adjust and give yourself grace. If we remove the shame from the struggle, it gives us space and clarity to address the issue.
If tricky transitions leave you feeling overwhelmed (or if ADHD makes routines feel impossible), therapy can help. Let’s make this school year more manageable — https://consultandtechcheck.timetap.com/#/.
If what’s hardest right now is sleep — racing thoughts, restless nights, or the back-to-school schedule wrecking your rest — CBT-I (Cognitive Behavioral Therapy for Insomnia) with Dr. Pimble can help you finally reset your sleep patterns. Learn more here: https://drpimbleconsultandtechcheck.timetap.com/#/