September is the New August
The business calendar you know is dead. Here's how to profit from its replacement.
So what happened? September has morphed into an extension of summer’s slowdown, effectively becoming “the new August”
The business calendar you learned, the one encoded in every MBA program, every sales manual, every startup accelerator?
It’s obsolete. A relic, I would say
And most people haven’t noticed yet.
For three years straight, I’ve tracked the same pattern across my portfolio companies. September, that sacred “back to business” month, has become a wasteland of out-of-office replies.
October is the new September. June is holding strong, while July has become the new June.
The entire Western business calendar shifted by 30 days.
And we’re all pretending it didn’t happen.
This isn’t some post-COVID hangover. This is permanent. And understanding why changes everything about how you should run your business, manage your career, and time your most significant moves.
We're getting a new speed.
The Great Calendar Migration
Here’s what the data shows.
Since September 2022, business activity has stayed 40% below 2019 levels or has even dropped further. Not revenue — activity. Meetings booked. Contracts signed. Decisions made.
The velocity of business itself.
But October?
October consistently hits 125% of historical September activity.
At first, I thought this was just my company. Maybe we were outliers. Statistical noise. So I started asking around. VCs, founders, sales leaders across three continents.
Everyone had the same story, but thought they were alone in it:
“September’s been weird lately.”
“Can’t get anyone on the phone until October.”
“Is it just me or...”
No. It’s not just you.
It’s structural. And it’s accelerating.
Last week, I analyzed 100,000 business emails across my network from the past three years. The pattern is undeniable:
September 2023 response rates: Down 47% from 2019
September 2024 response rates: Down 52% from 2019
September 2025 (so far): Down 58% from 2019
October stats (2023-2024): All up 30-40% above historical norms
We’re living through a massive behavioral shift, and the business world is sleepwalking through it.
Why This Happened
Three forces converged to shatter the old calendar:
1. The Exhaustion Economy
Market fatigue hit different this time.
We’ve had downturns before. We’ve had uncertainty. But we’ve never had three years of constant, relentless whiplash:
AI disruption (November 2022)
Bank collapses (March 2023)
Rate hikes (all of 2023)
Layoff waves (January 2023, June 2023, January 2024, March 2024)
AI acceleration (every month since GPT-4)
More layoffs (January 2025, ongoing)
Now AI Agents are eating entire job categories
2027 coming
The human nervous system wasn’t built for this frequency of change. We’re not adapting anymore. We’re coping.
People aren’t just tired. They’re existentially exhausted.
And when you’re that depleted, you don’t bounce back after Labor Day. You steal another few weeks. You extend that European trip. You push that big decision to October.
2. Remote Work Killed September’s Social Infrastructure
The old calendar worked because of peer pressure.
You couldn’t extend your vacation when everyone else was back at their desk. The empty parking lot in August, the full one in September — these were social signals that coordinated behavior.
But when “the office” is wherever you are, when Slack can wait, when nobody knows if you’re in Bali or Brooklyn, the social infrastructure that enforced September dissolved.
The result? Individual optimization replaced collective coordination. And when everyone optimizes individually, September dies.
3. The Fiscal Calendar Divorce
Nobody talks about this, but it’s crucial:
The financial year is increasingly divorced from the calendar year.
35% of S&P 500 companies now have non-December year-ends (up from 30% in 2023)
Startup fiscal years are all over the map
“Q4 urgency” might hit in February, June, or November
The shared rhythm that made September matter? Gone. Replaced by 500 different rhythms that cancel each other out.
Welcome to Compression Economy
Here’s where it gets interesting.
The year didn’t get longer. It got compressed.
What used to happen across four months (September through December) now happens in three (October through December).
Same amount of business. 25% less time. Exponentially higher intensity.
This creates a fascinating dynamic:
October isn’t just the new September — it’s September on steroids. All the energy, all the deals, all the decisions that used to spread across 120 days get compressed into 90.
I call this “calendar arbitrage.”
If you know October will be insane, you can position yourself in September while everyone else is still checked out. If you know June is still productive, you can close deals while competitors think summer has already started.
But compression creates something else: burst work.
Instead of a steady, sustainable pace, people are working in intense sprints followed by longer recoveries:
Three weeks on, one week completely off
Two months crushing it, three weeks in Thailand
Six months at 120%, two months at zero
The 9-to-5, Monday-to-Friday, September-to-August calendar assumed continuous partial attention.
The new calendar is about discontinuous full attention.
And that changes everything about how we should structure companies, teams, and careers.
The October Storm of 2025
With Fed rate cuts continuing through Q4 2025, October through December is about to be a perfect storm:
Even cheaper capital (rates down 200 basis points from 2024 peaks)
Compressed timeline (3 months to do 4 months of work)
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