Dancing Through September

September has a soundtrack. You know the one 🎶 Do you remember, the 21st night of September? 🎶 Earth, Wind & Fire didn't just give us a disco anthem, they gave us a time capsule. The song is both specific (that one day in September) and eternal (every September since). It's joy disguised as a reminder that beginnings and endings can happen in the same breath. A reminder I'm living in real time.

I've been running a lot lately - it's the one form of exercise that gives me mental freedom to escape. Back from a weekend upstate, officially in September, on a run with that soundtrack blasting in my ears. Usually, the song just makes me want to dance. This time, I listened closer. September isn't only about kids returning to school. It's about all of us: the cycle of gathering, releasing, and beginning again.

I was reminded of this at my daughter's Back to School night. Sitting in the tiny chairs, looking at the classroom where she'll spend the year, I flashed back to my own days of fresh notebooks and sharpened pencils. Only now I was in the parent's seat (older and supposedly wiser) realizing how much of adulthood is trial and error, learning and unlearning, improvising the curriculum as we go.

I caught myself drifting back to those childhood daydreams of "success someday." And in many ways, I've built pieces of that dream. But the reality check is this: I still have no idea what tomorrow has in store. Everything I've learned is less about mastering a plan and more about responding to whatever comes next.

This is September's lesson: we're always students of what comes next. I thought by now I'd be handing in my final project - proof that I'd figured out career, parenting, purpose, but September reminds me the lessons never end, and the question never disappears: is this it, or is there still more to learn?

Maybe that's the real back-to-school lesson. We never graduate. We're always students, starting over each September, knowing we'll:

The other night I was sitting on my couch, looking out at the Hudson. The sunset was gorgeous, but what really hit me was the time. September has a way of doing that - forcing you to pay attention. The days have been shrinking all along, but now you can't ignore it. Six o'clock suddenly feels like eight. And the Sunday Scaries? They hit different when you mix in that back-to-school dread, even if you haven't been in school for decades.

But it's not just daylight that September makes you notice...Yesterday was my daughter's first day of school, and the most difficult part wasn't the tears or the nerves - it was just getting her up in the morning, trying to leave on time so we wouldn't be late. Since it was her first day, I wanted to be there for both drop-off and pickup, to give her that feeling that I will always be there, that she's never going to be left alone.

But it was on the walk from our apartment to her school that September's lesson hit me differently. Here I am, in the middle of a career transition, and this uncertainty - this temporary state of not knowing what comes next - is actually a gift. I'm able to be fully present for this moment in ways I might not have been before. Will she remember this day? Probably not. But I will. I'll remember dropping her off, seeing her smiling face when she finished, the weather, the walk, the feeling of watching her start her own learning journey while I'm figuring out mine.

September is teaching both of us about beginnings, but from completely different perspectives. She gets a structured curriculum, new teacher, new classroom. I get the messier version: no clear syllabus, no obvious next step, just the faith that showing up matters. The seasons are changing, but so is everything else. Her childhood is moving forward on schedule. My career is in pause mode. Our family rhythm is shifting. The light is different, the morning routine is new, and somehow we're both students again.

I had to sacrifice a lot for this moment: the security of a steady paycheck, the clarity of knowing what comes next, the comfort of a defined role. But this temporary season is yielding something I can't put a price on - the ability to be present for the moments that matter most, especially when I don't know what September will teach us next.

September is pretty iconic if you really think about it, and maybe that's exactly the point. Even September's most predictable moments become teachers.

Pumpkin Spice everything - like that old friend you see once a year. You pick up exactly where you left off, no time passed at all. It's familiar, comforting, and reliable. The lesson? Some things are worth returning to, year after year.

College football brings nostalgia - the kind that takes you back to Saturday tailgates and rivalries that felt bigger than life. The NFL? That brings Fantasy Football, where suddenly every guy I know thinks he's a master strategist. Nostalgia on one hand, delusion on the other. Both are reminders of who we were and who we pretend to be. The lesson? We all need our traditions, even the ones that make us temporarily forget reality.

Then there's Fashion Week. A glimpse at next season's trends, it's forward-looking. It reminds us we can reinvent ourselves

But the real lesson happens in my apartment, pulling sweaters out of storage, when September forces the question I've been avoiding all summer: who do I actually want to be this season? The icons stay the same, but the person experiencing them keeps evolving.

Maybe that's why that Earth, Wind & Fire song endures. The song doesn't just ask us to remember; it demands we dance. And maybe that's what the song knows. We don't have to wait until we figure it all out to start moving. We can dance through the uncertainty, groove with the questions, and let the rhythm of the season carry us forward.

So maybe the real September lesson isn't just about beginnings and endings. It's about giving ourselves permission to keep dancing with the question: is this it, or is there more I want to carry into the next season of my life? Because the music's still playing, and the dance floor is always open.

The weekly section where I will call out a fraction: something that felt like progress this week (like a fraction forward) and a fiction: something that turned out to be a distraction or illusion. 

🎯 Fraction: The Powerball jackpot just hit $1.7 billion. The odds of winning? Practically nonexistent. And yet here we are, all of us, buying a ticket and playing the “what would you do if you won?” game over dinner. It’s a micro-fractional thought experiment: a single ticket in your pocket, a sliver of a chance. 

But then again, the odds of a complete jet engine failing mid-Atlantic were just as unthinkable… and that happened, and it’s the reason Is This It? even exists. That’s the fraction: life’s biggest shifts sometimes start with the smallest, most improbable chances.

🎭 Fiction: Meanwhile, back in Washington, fiction is on full display. Our government is literally projecting disbelief in science as if it were a legitimate policy stance. Public health — one of our country’s greatest accomplishments and one of the top reasons we were ever seen as a global leader — is now being treated like a choose-your-own-adventure story.

And here’s the kicker: the odds of winning the lottery might be microscopic, but the odds of undermining ourselves when we ignore science? Sadly, those are much higher.

If this resonates, pass it along to someone who might need to hear it.

What's your September lesson this year? Hit reply and let me know! I love hearing how these ideas land differently for different people.

Until next Friday, 

Chris

Next Week: New season, new brand. I thought I had my personal brand down cold, but a question from someone I respect made me realize it’s ready for a refresh.

Just like September reminds us we're all lifelong students, staying informed is part of the curriculum. That's why I've partnered with 1440 - a daily rundown of news that cuts through the noise and serves the essentials. Consider it required reading for students of what comes next. Check it out here 👇🏼

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