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When the Honeymoon Ends: A Leadership Pep Talk for September

When The Honeymoon Ends: A Leadership Pep Talk For September &Raquo; Overwhelm 300X300 1It’s the end of September, and the energy of a new school year feels different now than it did just a few weeks ago. The excitement of the first days has faded, the shine has worn off, and for many leaders, the honeymoon is officially over.

In conversations with leaders this week, I heard the same themes again and again. They’re dealing with personnel issues. They’re navigating student challenges. They’re starting to recognize that some long-term goals might not get met as originally planned, and they’re already making adjustments. If this sounds familiar, you need to hear this: you’re not failing—it’s normal.


The Punch in the Mouth Moment

When The Honeymoon Ends: A Leadership Pep Talk For September &Raquo; Tyson 2 143X300 1Mike Tyson once famously said, “Everyone has a plan until they get punched in the mouth.” For leaders, September often feels like that punch.

You spent the summer planning, preparing, and mapping out the year ahead. You launched with vision and energy. But by late September, reality shows up. People issues surface. Initiatives slow down. That shiny plan you built back in July suddenly looks a lot messier.

And here’s the truth: every leader experiences this. You are not alone.


The Common Trap

Here’s where the danger lies—it’s not in reaching this point. It’s in what happens next. Too many leaders get stuck in the weeds. They keep grinding forward, ignoring the warning signs, and pushing down a path that’s no longer aligned with the bigger picture.

That’s the mistake: not recalibrating when the reality shifts.


The Balcony Perspective

When The Honeymoon Ends: A Leadership Pep Talk For September &Raquo; Balcony Rendering 300X300 1This is where you need to do something simple, but powerful: step out of the weeds and onto the balcony.

On the balcony, you see differently. You notice the patterns you missed when you were caught in the day-to-day. You can step back, breathe, and reorient yourself and your team. From that vantage point, you can point forward again and say, “This is our path. Everyone follow me.”

It doesn’t mean the problems disappear. But it does mean you lead with Clarity, instead of reacting from chaos.


A Pep Talk, Not a Prescription

When The Honeymoon Ends: A Leadership Pep Talk For September &Raquo; Img 1731 300X300 1This post isn’t a list of strategies or a new framework. It’s simply a reminder that you’ve got someone in your corner cheering you on.

Reaching this point in September is not a leadership failure—it’s just part of the journey. What matters is that you pause, get perspective, and reestablish your direction.

So take a breath. Step onto the balcony. Look around. And then turn to your people with confidence: “We’ve got this.”


Let’s Bring This Work to Your Team

The honeymoon may be over, but that doesn’t mean the best part of the year is behind you. In fact, this is where the real work—and the real leadership—begins.

When The Honeymoon Ends: A Leadership Pep Talk For September &Raquo; Img 0796 300X300 1If you or your team could use a guide to walk alongside you in this work, I’d Love to help. Let’s talk about how we can bring this kind of transformation to your school or district.

Together, we can move from firefighting to focused leadership.

📩 Send me a message or visit RoadToAwesome.net to start the conversation.

Tune in this Sunday to “Leaning into Leadership”  when I sit down with Dr. Zac Bauermaster to talk faith, Family, and fist bumps in the hallways.

Darrin Peppard Dr. Darrin Peppard

Dr. Darrin Peppard is an author, leadership coach, consultant, and speaker focused on organizational culture and climate, and growing emerging leaders. Darrin is the best-selling author of the book Road to Awesome, and is the host of the Leaning into Leadership podcast. As a ‘recovering high school principal’, Darrin shares strategies and lessons learned from 26 years in public education to help leaders gain clarity, find joy in their work, and walk in their purpose.

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