The Gentle October Business Check-In
If your year were a story, October would be the chapter where everything slows down just enough for you to finally notice the plot again.
It’s the month where your intuition gets louder, your schedule starts hinting (sometimes aggressively) at what needs attention, and your business starts whispering, “Hey… before we head into the holidays, can we talk?”
I love October because it can have this beautiful, grounding energy to it — not quite the sprint of summer, not yet the sparkle of holiday season. It’s the in-between. The exhale. The moment where you can look at your business with total honesty without spiraling, panicking, or questioning all your life choices.
Which is why October is the perfect time for a gentle business check-in.
Not a full audit. Not a dramatic burn-it-all-down rebrand.
A check-in — the cozy, supportive kind.
The kind where you wrap yourself in a blanket, light a candle, and say,
“OK, business mama… how are we actually doing?”
Let’s walk through a simple, grounding, energy-aware October check-in — one that helps you breathe easier now and sets you up for a peaceful slide into the end of the year.
1. What’s Actually Working (Even If It Surprises You)?
Before you look at anything that needs fixing, start by noticing what’s already going beautifully.
Because here’s something that many entrepreneurs forget:
You’re doing way more things right than you think!
So take inventory of what’s currently flowing — things like:
Your most engaged content
Offers clients keep coming back for
Workflows that feel natural instead of forced
The parts of your process that feel like “you”
Clients who feel aligned and energizing
Systems that quietly run in the background without drama
We tend to only notice the squeaky wheels, the messy inbox, the project that’s been open since July… but October is your reminder to honor your wins, your ease, and the things that are actually supporting you.
Let something in you soften as you acknowledge the pieces that are holding strong.
They’re the foundation you get to build on.
✨ Gentle tip for future: Have a designated page in your notebook (or note in your Notes app) just for your wins.
I noticed I was bad at remembering these things, so I dedicated a couple of pages in my notebook (where I do everything) to jot down my wins — big and small — throughout the year. I wrote in designated headers for each quarter of the year, and as I think of things, I flip over there and jot them down. And occasionally, when it’s been a rough day or I just need a boost, I’ll flip over there and see what I’ve accomplished, and it feels surprisingly great.
2. What’s Feeling Heavy, Sticky, or Draining?
Now that you’re grounded in what’s working, it’s time to look — gently — at what isn’t.
You don’t need to fix everything today.
You don’t need to overhaul your whole business.
But October is a great moment to notice what’s been whispering for your attention.
Ask yourself:
What tasks feel like wading through wet cement?
What parts of your workflow always get skipped or postponed?
What’s currently draining your energy faster than it should?
What systems feel outdated… or just “not me anymore”?
What boundaries slipped (or flat-out evaporated) in the last few months?
What feels out of alignment when you’re honest with yourself?
Sometimes the heaviness isn’t even about the task itself — it’s about:
The amount of decisions inside it
The lack of clarity around it
The pressure you’ve attached to it
The system (or non-system) holding it
The season of life you’re in
Your job here is NOT to fix every heavy thing.
Your job is to notice it.
Awareness creates possibility.
Possibility creates change.
Change restores flow.
One step at a time.
3. What Needs Simplifying Before the Holidays?
October is the moment to simplify.
Not in a “minimalism documentary on Netflix” kind of way…
More like, “What would make my life easier for Future Me in December?”
Think about the next two months:
Your client load
Your offers
Your workflow
Your communication
Your content rhythm
Your tech
Your personal life!! (Yes, you matter too.)
Ask:
What could I make simpler?
What could I automate?
What could I say “no” to?
What could I templatize?
What could I batch now to save myself stress later?
Where am I overcomplicating something that wants to be easy?
This is the time to:
Clean up your tools
Delete the cluttered to-do list
Refresh your client boundaries
Revisit your scheduling structure
Tidy your digital spaces
Prep email templates
Streamline your content flow
Decide what’s “enough” for the rest of the year
October is energetically supportive for simplification.
Let it help you.
4. What Can Be Paused (or Put Down Entirely)?
Some things in your business are not meant to be carried into the holidays with you.
Not because you failed.
Not because you’re inconsistent.
But because you’re human — and your energy has seasons.
Ask yourself:
What am I holding onto because I “should,” not because I want to?
What projects can wait until January without harming anything?
What’s draining energy but not delivering support, clarity, or joy?
What’s something I was experimenting with that can I now gracefully release?
You’re allowed to pause things.
You’re allowed to take things off your plate.
You’re allowed to gently say, “Not right now.”
Your business will thank you for it.
5. What Support Would Feel Nourishing Right Now?
This might be the most important part of your gentle October check-in.
We often try to “be the entire team,” even when our energy is waving a white flag.
Ask yourself:
Where could I use support — practical or energetic?
Who can I delegate to, even in small ways?
What would make my workflow feel lighter?
What could I invest in that would give me back TIME?
Do I need human support, tech support, or nervous-system support?
Support doesn’t always mean hiring someone.
It might look like:
A scheduling tool doing the heavy lifting
A template saving you 45 minutes every time
A grounding ritual before client calls
A friend who listens
A massage or Reiki session 😉
A therapist
An accountability buddy
Saying “no” to things you don’t have bandwidth for
Support creates space.
Space creates clarity.
Clarity creates ease.
You deserve all three.
Tech Tip:
The 20-Minute Dashboard Reset
Before the holiday rush hits, give your digital tools a reset that actually simplifies your life instead of complicating it.
Try this:
Set a timer for 20 minutes and clean up ONE of these:
Your scheduling tool (delete old availability, add holiday hours)
Your project tool (archive old tasks, clear notifications, update priorities)
Your email folders (create 2–3 simple ones you’ll actually use)
Your desktop (no judgment — we’ve all had “chaos chic” desktops)
The goal isn’t to organize your entire business.
The goal is to clear just enough digital clutter that your tools feel supportive again.
Twenty minutes. One area. Big exhale.
Why This Matters (Energetically Speaking)
Energetically, October is the pivot point of the year.
It’s the moment where you shift from the outward growth of spring/summer into the more inward clarity of fall/winter.
Your intuition sharpens.
Your nervous system asks for grounding.
Your business wants to be realigned.
When you ignore this shift, you end up pushing through the next two months with scattered energy and unnecessary pressure.
But when you honor the shift?
Your work feels steadier
Your decisions feel clearer
Your boundaries get stronger
Your intuition comes online
Your creativity returns
Your workflow softens
Energetically aligned businesses become sustainable businesses.
And October is one of the best moments of the year to tune in and recalibrate.
Empowered Next Step:
Choose Your “October Anchor”
Instead of trying to fix everything, choose one anchoring focus for the rest of October — something that will calm your nervous system, stabilize your workflow, or reduce overwhelm.
Ask yourself:
“What’s the one thing that, if I tended to it now, would make the rest of the year feel easier?”
Your October Anchor could be:
Updating your client boundaries
Decluttering or simplifying your workflow
Refreshing your onboarding process
Cleaning up your digital workspace
Revisiting your content rhythm
Reworking your schedule or availability
Tending to your energy before your systems
Pick ONE thing. Circle it. Commit to it gently.
A single anchor creates more stability than ten half-finished improvements.
This is how you enter the holiday season with clarity, instead of chaos.
The Heart of It All
Your business is not a machine — it’s a living extension of you.
And just like you, it needs moments of honesty, recalibration, and grounding.
A gentle October check-in isn’t about perfection or productivity.
It’s about presence.
It’s you saying:
“I care about this business. I care about my energy. I care about how we move into the next season… together.”
When you stabilize now, the rest of the year flows with so much more ease.
Frequently Asked Questions About October Business Check-In
Q: Do I really need to do this every October?
Not at all — but many entrepreneurs find October offers the most clarity. It’s far enough from summer to see what stuck, and close enough to year-end to adjust.
Q: What if everything feels heavy?
Start with ONE thing. One system, one offer, one boundary. Never overhaul from burnout.
Q: How long does a check-in take?
30–60 minutes. A cozy, candle-lit hour is plenty.
Q: How do I know what to prioritize?
Whatever is draining you most — emotionally or logistically. Your body will tell you before your brain does.
Q: Can I do this with a friend or business buddy?
100% yes. Reflection is often easier with a witness. You’ll see things you’d overlook alone.
Final Thoughts
You don’t have to push through the end of the year on adrenaline and iced coffee.
You can enter the busiest season feeling grounded instead of overwhelmed — steady instead of scattered — supported instead of stretched thin.
A gentle October check-in gives you that foundation.
So take the time.
Light the candle.
Ask the questions.
Soften into the answers.
Your business will feel better.
Your energy will feel better.
YOU will feel better.
And your clients will feel the difference in every session, email, and offering.
Still Have Questions?
If you have any questions I didn’t cover here, or if you’re looking for advice specific to your business, feel free to reach out. I’d love to help you grow your business in a way that feels aligned and sustainable!
