There’s loads of content opportunities between Labor Day and turkey day – and most businesses miss them all…
So, there you are, sipping your morning coffee on September 2nd, scrolling through your content calendar, and suddenly it hits you.
There’s this weird content void staring back at you between Labor Day and Christmas.
Sure, you’ve got Halloween penciled in (maybe), but what about all those weeks in between?
Meanwhile, your competitors are posting the same tired “Happy Monday” graphics while you’re sitting on a treasure of connection opportunities they’re completely ignoring.
The Content Void That’s Costing You Connections
Here’s what most small business owners do during Fall: they post some back-to-school content in September, maybe throw up a Halloween post or two, then basically hibernate until Black Friday hits.
Sound familiar?
But here’s something important to remember.
Your audience doesn’t hibernate.
They’re living their lives, feeling grateful, celebrating small wins, dealing with seasonal changes, and looking for brands that actually get it.
When you disappear from their feeds, you’re not just missing content opportunities.
You’re missing relationship-building moments that could turn casual followers into loyal customers.
Think about it.
This is the season when people naturally start reflecting on what they’re thankful for.
They’re slowing down from summer chaos, getting cozy, and craving authentic connections.
Yet most businesses treat September through November like some weird holding pattern before the “real” holiday season begins.
Smart business owners know this period is actually a time when you can show up authentically, build genuine connections, and position yourself as the brand people think of first when they’re ready to buy.
fall’s Hidden Content connection treasure
Let me spill the coffee (metaphorically, of course!) on something most entrepreneurs miss.
The weeks between Labor Day and Thanksgiving are packed with content opportunities that actually matter to your audience.
We’re not talking about forced National Donut Day posts (though if donuts are your thing or you’re a bakery, go for it).
We’re talking about real moments that connect with what people are experiencing.
September: The Fresh Start Energy
September brings this amazing “new school year” energy, even for adults.
People are getting back into routines, setting new goals, and feeling motivated after summer’s laid-back vibe.
Your content can tap into this by focusing on fresh starts, organization, goal-setting, and getting back to business.
Coffee connection moment: Share your “back-to-business morning routine” with that perfect cup of coffee that kickstarts your productive day. People love seeing the real, human side of how you operate.
October: Cozy Productivity
October is where the magic happens. The weather’s changing, people are settling into Fall rhythms, and there’s this perfect blend of productivity and comfort. It’s sweater weather meets getting-stuff-done energy.
Your content can focus on creating systems, building habits, and finding balance during busy season prep.
This is also when people start thinking about year-end goals and planning for next year. Perfect time for reflection content, planning tools, and “getting organized for the holidays” type posts.
November: Gratitude and Community
November is obviously the gratitude month, but here’s where most businesses go wrong: they post generic “thankful” content that sounds like everyone else.
I recommend that you get specific. What are you actually grateful for in your business? How have your customers impacted your life? What small wins deserve celebrating?
This is also prime time for community building. People are thinking about family, friends, and the relationships that matter.
Your content can focus on building connections, supporting others, and creating that warm, inclusive feeling your audience craves.
Fall Content That Connects
Week-by-Week Approach That Works
Instead of scrambling for content ideas each week, plan your Fall themes around what your audience is naturally experiencing. Here’s an idea of how to structure September through November content for maximum connection:
Early September: Fresh Starts and New Beginnings
- Share your own fresh start story
- Offer planning tools or templates
- Talk about seasonal goal-setting
- Create “getting back to routine” content
Mid-September: Building Momentum
- Share productivity tips that actually work
- Talk about systems and processes
- Create content around overcoming overwhelm
- Share behind-the-scenes of your busy season prep
Late September/Early October: Seasonal Shifts
- Acknowledge the changing season in your business
- Share how you’re adapting to Fall rhythms
- Talk about preparing for the upcoming busy season
- Create cozy, comfortable content
Mid-October: Preparation and Planning
- Share holiday prep without being pushy
- Talk about Q4 goals and planning
- Create content around getting organized
- Share seasonal business tips
Late October: Reflection and Assessment
- Look back at the year so far
- Share lessons learned
- Talk about what’s working and what isn’t
- Create content around pivot strategies
Early November: Gratitude and Recognition
- Share genuine appreciation for your audience
- Highlight customer stories and wins
- Thank your team or supporters
- Create community-focused content
Mid-November: Connection and Community
- Focus on relationships and connections
- Share stories about your business community
- Create content that brings people together
- Talk about the importance of support systems
Late November: Thanksgiving and Reflection
- Share what you’re genuinely grateful for
- Reflect on business growth and challenges
- Create content around abundance mindset
- Set the stage for the holiday season
Content Ideas That Actually Work
Storytelling That Connects
The best Fall content tells stories.
Not made-up marketing stories, but real experiences your audience can relate to.
Share the messy middle of building your business.
Talk about the morning you realized you needed better systems (probably over your third cup of coffee).
Tell them about the customer email that made your day.
Gratitude Content That Doesn’t Suck
Skip the generic “grateful for our customers” posts. I want you to get really specific:
- Share the exact moment you knew your business was working
- Talk about a customer who taught you something valuable
- Highlight a small win that felt huge
- Show appreciation for your support network
Behind-the-Scenes Fall Prep
People love seeing how the toys get made, especially during busy season prep.
Share your holiday planning process, show your workspace getting organized for Q4, or document your content creation sessions (bonus points if there’s coffee involved).
Community Building Content
Use this season to strengthen your community.
Ask questions that matter: What’s your biggest business challenge heading into Q4? How do you stay motivated during busy season? What’s one thing you’re proud of accomplishing this year?
Making It Personal (Without Oversharing)
The magic of Fall content is in the personal touches.
You don’t need to share your life story, but giving people glimpses of your real experience makes your brand memorable.
Maybe it’s your morning coffee ritual, your favorite Fall playlist while working, or how you’re decorating your workspace for the season.
Here’s what I know about authenticity: it’s not about being perfect or having everything figured out.
It’s about being real about where you are and what you’re working on.
Your audience doesn’t need another guru telling them they have all the answers.
They need someone who gets it and is figuring it out alongside them.
Timing Your Content for Maximum Impact
The Early Bird Strategy
Start your Fall content themes early. While everyone else is posting summer content until the leaves change, you’re already connecting with your audience around what’s coming next. This positions you as someone who thinks ahead and understands their needs.
The Consistent Connection Approach
Don’t just post randomly about Fall themes. Create a consistent thread throughout the season. Maybe it’s a weekly gratitude post, regular behind-the-scenes updates, or a monthly community spotlight. Consistency builds anticipation and keeps people coming back.
The Natural Transition Technique
Let your content naturally evolve with the season. Start with fresh energy in September, build momentum through October, and focus on gratitude and connection in November. Your audience will feel like you’re moving through the season with them, not just posting at them.
What to Do Right Now
First, grab your favorite coffee (seriously, this works better caffeinated), and map out your September through November themes.
What’s happening in your business during this time? What are your audience’s biggest challenges and needs? How can you show up authentically during each phase of Fall?
Next, brainstorm specific content for each theme.
Don’t overthink it. Simple, genuine content performs better than perfect, polished posts that feel distant.
Finally, plan your posting schedule around these themes.
You don’t need to post daily, but consistency matters more than frequency. Better to post twice a week consistently than to post daily for two weeks then disappear.
The goal isn’t to create more content for content’s sake. It’s to show up meaningfully during a season when your audience is naturally thinking about connection, gratitude, and preparation for what’s ahead.
Your content calendar between Labor Day and Thanksgiving shouldn’t feel like filler.
It should feel like a warm conversation with people you genuinely care about, shared over coffee, about what really matters.
That’s content that connects.
Start with one authentic post about what September means for your business.
Your audience is waiting to connect, you just need to show up and start the conversation.
You’ve got this!
Want to hook your audience during Fall’s relationship-building season? Download How to Hook Your Audience and Keep Them on the Line and turn those September-November connections into loyal customers!
