How leaders can protect the calm, perspective and healthier routines summer gives them, before the September Squeeze takes it all back.
A few weeks ago, I was driving home from the cottage feeling, frankly, rather pleased with myself.
The convertible top was down, Kurt Vile was playing, the sun was out, and I had that wonderful feeling that follows a genuinely good break. I'd been swimming every day, jogging up hills that seemed far less daunting by the end of the trip than the start, seeing friends, reading, sleeping, and generally doing all the things I know are good for me but somehow can never fit into an ordinary work week.
I felt rested, clear-headed and remarkably in control of my life. And somewhere along the highway, I made myself a promise: I am not going to lose this feeling. I suspect many of us have made some version of that promise.
A good vacation does something interesting to us. Once we properly disconnect, we remember that we are people with interests, relationships and bodies that need to move, rather than highly efficient delivery systems for email. We start imagining how things might be different when we get home. We tell ourselves, I'm going to keep swimming. I'm going to stop checking email at night. We're going to see our friends more often. I'm definitely going to keep jogging up those hills. And for a few glorious days, we do. Then the calendar starts turning toward September.
The September Squeeze
At first, it's subtle. A few more emails arrive. Meeting invitations begin appearing. Someone wants to “get something in the calendar for early September.” Then someone else does. And suddenly those back-to-school ads feel less like cheerful marketing and more like a warning.
September, which looked comfortably far away from a dock in July, is now alarmingly close. Projects are restarting. Clients are returning. Targets are looming. And decisions that could easily wait until “after the summer” apparently cannot wait a moment longer.
I call this the September Squeeze: the uncomfortable collision between the spaciousness of summer and the compression of fall. Our instinctive response is usually exactly the wrong one. We speed up before we need to. We fill the calendar. We mentally rehearse everything that could go wrong. And gradually, almost without noticing, we begin handing back everything the break gave us.
I think of what we gain from real time off as our Vacation Dividend. We don't simply return rested, we return with perspective, with energy, with healthier routines and a bit of room to think. Sometimes we even solve the problem we'd been wrestling with all spring, precisely because we finally stopped trying to.
The trouble is, the Vacation Dividend doesn't protect itself. Work is remarkably efficient at reclaiming every square inch of space we give it.
And if you're a leader, there's a second dimension: the Squeeze isn't only happening to you. It's happening to everyone around you. Whether you lead ten people or a thousand, they're all coming back with their own mix of renewed energy, good intentions and quiet apprehension about what fall will ask of them. If the leader comes charging back in at full speed, the message travels fast:
Summer's over. Brace yourselves.
But there are still a few weeks of summer left. Warm evenings, long weekends, time outside. They shouldn't be squandered worrying about September. So here are three things leaders can do now to get ready for fall without prematurely surrendering summer.
Protect What Restored You
First, resist the urge to keep all of it. My fantasy version of post-vacation life involves daily swimming, long hikes, leisurely dinners with friends and a suspiciously empty calendar. Reality may have some objections. So choose one thing.
What did you do this summer that noticeably changed how you felt? Maybe you read before bed instead of scrolling. Maybe you saw people you'd been meaning to see for months. Pick one, and protect it before September fills the space.
Then ask your team the same question: What's one thing you did this summer that you don't want work to take from you this fall? It sounds small, but it says something important: coming back doesn't mean abandoning everything that made us healthier while we were away.
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Preview What's Actually Coming
The second practice is to get fall out of your head and onto the table. The September Squeeze feeds on vagueness. There's so much coming. September's going to be crazy. We have so much to deliver. Left swirling around in our heads, it only grows.
So before everyone plunges into full-speed fall, bring the team together and look at what's actually ahead. What genuinely has to happen between September and December? What are the three or four things that matter most? Where are the pressure points? What can wait? And when the inevitable new opportunity, crisis or executive request lands, ask the question leaders too often skip: If this moves up, what moves down?
This isn't about building the world's most beautiful fall plan. It's about replacing a vague sense of impending doom with some collective control over what's next. One of the most useful things a leader can do for people under pressure is help them tell the difference between what feels urgent and what actually matters.
Pace the Re-entry
The third practice may be the hardest, because it runs against a deeply ingrained leadership reflex: when pressure rises, leaders accelerate. We add meetings. We increase the check-ins. We shorten the timelines. Things that were merely important in June somehow become “critical” in September. Then we wonder why everyone is exhausted by October.
What if we deliberately resisted that impulse? Use these last few weeks for the conversations that make fall easier, clarify expectations, surface concerns, make the decisions that have been hanging around too long, remove friction where you can. But don't manufacture urgency simply because September is approaching.
And watch the pace you're modelling. If you're answering email at midnight and talking constantly about how crazy fall is going to be, your team is getting the message whether you mean to it or not.
There's work to be done, of course. There always is. But there's also still time to go for the bike ride, have friends over, and flip a burger on the barbecue without mentally tallying the emails piling up while you do it. The goal isn't to squeeze every last drop of productivity out of summer. It's to arrive at fall ready for it.
Don't Give It All Back
I keep thinking about that drive home from the cottage. I wasn't oblivious to what was waiting for me. I knew the targets were there. I knew the calendar would fill, that there'd be hard decisions and unexpected problems and days when the carefully protected bike ride simply wasn't going to happen. But for that stretch of highway, I had something that's remarkably easy to lose in leadership:
Perspective.
Perhaps that's what we should be trying to hold onto as summer winds down. Not the fantasy that we can make September feel like vacation, but the quiet realization that we don't have to give September everything.
The September Squeeze is coming. It always does. But you don't have to hand back your Vacation Dividend without a fight.
A decidedly less evidence-based approach to the September Squeeze.
Only in the most dire of circumstances resort to the anti-stress therapy pictured above. I'm fairly certain the research base is thin.
What's one thing summer gave you that you're not willing to hand back?