The September Reckoning

Why working with human psychology beats fighting against it

Hey there,

This week marks the end of our three-part exploration of transformation. We started with the Elul Principle—why transformation requires deliberate unbecoming, not just accumulation. Last week, we explored the Legacy Game Paradox—why adaptive capabilities matter more than tool optimization.

Today, we tackle the final piece: timing. Because understanding what to shed and what to build means nothing if you ignore when humans are actually ready to learn.

I'm writing this as my younger daughter starts her freshman year in engineering at UW, while my older daughter settles into her senior year at CU Boulder. The contrast between their energy levels is striking. My freshman is electric with possibility—everything feels new, challenging, exciting. My senior is focused, deliberate, applying four years of accumulated wisdom to final goals.

Two completely different types of thinking happening simultaneously, and both are essential for transformation.

Meanwhile, corporate America continues its relentless march through Q3 planning cycles, completely oblivious to the most powerful learning energy of the year flowing all around them.

The Unjaded vs. The Experienced

This dual-track dynamic isn't just about academic phases—it reveals something fundamental about how different cognitive states approach learning and change.

Unjaded Energy = System 1 Thinking: Wide-eyed optimism, high tolerance for ambiguity, rapid experimentation. These are your team members who still believe everything is possible because they haven't internalized all the constraints yet. They approach AI tools with genuine curiosity, unburdened by extensive knowledge of why things "should" fail. Their cognitive resources aren't depleted by defensive expertise.

Experienced Energy = System 2 Thinking: Strategic skepticism, systematic processes, leveraging accumulated knowledge for quality control. These are the people in meetings who can tell you 10 different reasons why your AI initiative won't work—and they're usually right about the pitfalls, even if they're wrong about the possibilities. Their pattern recognition is sophisticated, but their psychological openness has been professionally conditioned out of them.

[System 1 and System 2 thinking from Daniel Kahneman's framework describe fast, intuitive cognition versus slow, deliberate analysis.]

Most AI transformation efforts try to force everyone into one cognitive mode. The unjaded optimism without strategic thinking creates expensive chaos. The experienced skepticism without experimental energy kills innovation before it starts.

But successful transformation requires both cognitive approaches operating simultaneously—exactly what natural renewal periods like September enable.

The Science Behind Fresh Start Psychology

There's robust research supporting what intuition suggests about temporal landmarks and motivation. The "fresh start effect," documented by Wharton researchers Hengchen Dai, Katherine L. Milkman, and Jason Riis in their 2014 Management Science study, shows that meaningful calendar dates create psychological clean slates that motivate aspirational behavior. Google searches for "diet," gym visits, and goal commitments all increase following temporal landmarks like the start of new weeks, months, years, or semesters.

But the neuroscience goes deeper. Functional MRI research from the University of Liège demonstrates that brain activity for attention peaks during summer and dips in winter, while working memory function peaks in fall and drops in spring. As lead researcher Gilles Vandewalle told Scientific American: "It's [been] conclusively shown that cognition and the brain's means of cognition are seasonal."

The implications are staggering: The "cost of cognition"—neural resources available for thinking—changes dramatically with time of year, even when performance remains stable. Your team's capacity for different types of learning literally fluctuates with natural cycles that corporate calendars completely ignore.

The Energy Most Companies Waste

There's something profoundly dysfunctional about how organizations approach learning compared to natural human cycles. September brings renewal energy that humans have been conditioned to feel for decades of their lives. New notebooks. Fresh starts. The psychological momentum of "this year will be different."

And most companies completely ignore it.

Instead, they launch AI transformation initiatives in February (middle of winter doldrums), mandate new processes in June (when everyone's thinking about vacation), or announce major changes in November (just as people are mentally checking out for the holidays).

A year ago, I wrote about this phenomenon from a different angle—the Year-End Push. I observed that August and September create natural energy for strategic thinking that most product managers miss entirely. While others ease back into work gradually, ambitious professionals use September energy to set themselves apart through proactive planning and strategic initiative.

The same principle applies to organizational transformation, but at a much deeper psychological level.

Why Teams Must Master Two Speeds of Thinking

Watching my daughters navigate their different phases revealed something most organizations completely fail to understand: successful transformation requires orchestrating two distinct cognitive approaches simultaneously.

Unjaded Exploration: Beginner's mind, experimentation, rapid iteration, comfortable with confusion and uncertainty. Everything is new, so failure feels like discovery rather than incompetence. These team members dive into AI tools without preconceptions about what should or shouldn't work.

Experienced Evaluation: Applied judgment, systematic analysis, leveraging accumulated knowledge to identify real versus superficial improvements. Experience creates efficiency and quality control, but can also create resistance to fundamental change.

Most AI transformation efforts try to force everyone into the same cognitive track. They either treat experienced team members like newcomers (insulting their expertise) or expect beginners to immediately operate with senior-level strategic thinking (setting them up for failure).

Your team needs both cognitive approaches operating simultaneously, and natural renewal periods create permission for this duality.

The September Advantage (Or March, Or January, Or Monday)

This isn't about waiting for September. It's about recognizing when natural temporal landmarks create psychological conditions that amplify learning rather than fighting against it.

But here's where this gets tricky: I've written before about "The Fresh Start Trap"—how teams use temporal landmarks to launch superficial process changes that feel transformative but avoid the hard work of genuine transformation. The dopamine hit of a new beginning without the discipline of sustained change.

The crucial distinction is what kind of change you're pursuing. Fresh starts are dangerous when they become substitutes for deep work, but powerful when they create psychological permission for deep work. Using September energy to launch your 47th attempt at "better standup meetings" is the trap. Using September energy to fundamentally examine what mental models you need to release and what adaptive capabilities you need to build—that's strategic leverage.

Fresh starts are dangerous when they become substitutes for deep work, but powerful when they create psychological permission for deep work.

The Unjaded Permission: Even experienced team members feel permission to experiment and ask basic questions during fresh start periods. Natural renewal energy temporarily overrides professional ego and expertise defense mechanisms.

The Experienced Focus: Leadership teams feel natural urgency about "getting this right" that drives systematic thinking and resource allocation decisions.

The Compound Effect: When both energies operate simultaneously, teams develop adaptive capabilities faster because they're combining experimentation with strategic focus rather than cycling between them.

The framework works with any temporal landmark—the start of quarters, new projects, post-vacation returns, even Mondays. The key is recognizing these psychological windows and designing transformation initiatives around them rather than steamrolling through them.

The Geographic and Cultural Reality

This applies to March-April for our Southern Hemisphere colleagues, January for companies with calendar-year planning cycles, or any meaningful fresh start that your specific culture recognizes. The principle isn't tied to September specifically—it's about developing sensitivity to when your team is psychologically ready for change rather than forcing change when it's bureaucratically convenient.

This connects directly to everything we've explored in this three-week series:

Most AI transformation fails because organizations approach it as tool adoption rather than identity evolution. The Elul Principle showed us that real change requires deliberately releasing mental models that made us successful in the pre-AI era—not just adding new capabilities on top of old thinking. The Legacy Game Paradox revealed that sustainable competitive advantage comes from building organizational reflexes for continuous adaptation, not optimizing for today's AI landscape. And now we see that even the best transformation strategy fails if it fights against basic human psychology rather than leveraging natural renewal cycles that make change feel possible rather than threatening.

What can we learn from all of this? Transformation that lasts requires psychological permission to let go of the past, strategic focus on adaptive capacity over current optimization, and wisdom about when humans are actually ready to evolve. Most companies get one or two of these right. The organizations that will dominate the AI era understand that timing, identity, and capability development form an integrated system—not a checklist of separate initiatives.

Transformation that lasts requires psychological permission to let go of the past, strategic focus on adaptive capacity over current optimization, and wisdom about when humans are actually ready to evolve.

Your Next Fresh Start Opportunity

Whether it's this week, next month, or next quarter, you have regular opportunities to work with human psychology instead of against it.

• Questions You Should Ask Yourself:

• What AI transformation initiative have you been delaying? Fresh start energy makes almost any learning initiative feel more approachable.

• How could you leverage the natural unjaded/experienced dynamic on your team? Who brings beginner's mind, and who brings strategic evaluation to your AI journey?

• What would change if you designed your AI capability development around natural learning cycles instead of purely business calendars?

• When's your next temporal landmark, and how could you time a learning initiative to leverage rather than fight psychological readiness?

The meta-question: Are you optimizing your transformation timing around business convenience or human psychology?

The Compound Advantage of Psychological Alignment

When you align transformation initiatives with natural human cycles, you're not just improving adoption rates—you're building transformation capabilities that compound over time. This is what separates strategic leaders from tactical managers.

Teams that learn to leverage fresh start energy for major learning initiatives develop organizational reflexes for recognizing and utilizing optimal psychological windows. They become systematically better at timing transformation efforts because they understand the psychology of change, not just the mechanics.

While your competitors burn energy fighting against natural learning rhythms, you're building sustainable competitive advantage by working with human psychology instead of against it.

The real opportunity isn't any specific fresh start—it's developing institutional wisdom about when and how humans are most ready to evolve.

And that wisdom becomes your most sustainable competitive advantage, because it applies to whatever transformation challenge comes next.

Break a Pencil,

Michael

P.S. Ready to leverage natural learning cycles for systematic AI capability development? My private cohorts are designed around psychological readiness and natural renewal energy, combining the strategic frameworks from this three-week series with timing that makes transformation sustainable. [Learn more here.]

Or join my public "Build an AI-Confident Product Team" course starting October 14 on Maven—where product leaders learn to navigate AI transformation with both strategic frameworks and psychological insight. [Learn more here.]

P.P.S. This concludes our three-part exploration of transformation psychology. If you missed the earlier pieces: "The Elul Principle" explores what to release, "The Legacy Game Paradox" covers what to build instead. Together, they form a complete framework for approaching AI transformation as identity evolution rather than tool accumulation.

If this series challenged how you think about organizational change, share it with that product leader who's still treating AI adoption like tool accumulation instead of transformation psychology. They need this framework more than they need another demo of the latest productivity app.

New to Broken Pencils? Get weekly insights on product leadership and AI transformation that challenge conventional wisdom. [Subscribe here.]