planning club.
Where business owners plan with intention—and no one’s pretending to have it all together.
What matters most today keeps getting
shoved to tomorrow…
Because today? Today just got hijacked...again.
Your to-do list? Didn’t stand a chance.
Before your feet even hit the floor, you’re already drowning in notifications.
That “quick check” of your inbox? Now 20 minutes of scrolling.
“Just a quick look” at Instagram—and now you’re deep in someone’s vacation photos, wondering how someone you went to high school with can afford a villa in Tuscany.
Then there are the meetings, the errands, the endless pings, the kid stuff, the “urgent-but-not-really” tasks that multiply like rabbits.
And before you know it, the day’s over.
That big, meaningful thing you actually wanted to get done?
Didn’t happen. Again.
Planning Club helps you actually do the things that you keep moving to next week’s to-do list.
With monthly co-planning, bi-weekly co-working, and a supportive community, this is structure that adapts to real life—not the Pinterest version.
(*Lock in this special rate for life)
Here’s the deal.
You’re not lazy or unmotivated. You’re overwhelmed—and still trying.
You’re a business owner with a real life,and you need a system that doesn’t fall apart the moment life gets real — like when your kid gets sick, clients want things yesterday, your Wi-Fi crashes, or your brain decides “Nope, we’re done here” by noon.
Kids. Clients. Deadlines. Health stuff. Economic whiplash!
Yeah, it’s a lot!
You didn’t start your business to feel behind, buried in decisions, or stuck at the end of the day wondering if you moved the needle — or just shuffled paper.
And you definitely didn’t sign up to stare at your to-do list for three hours, only to end the day wondering what actually got done.
You need more than a pretty planner (okay, maybe one pretty planner!) or another “hack.”
You need a planning rhythm that flexes with your life — plus a community of business owners who get that building a business is messy, unpredictable, and way better with a little laughter (and a lot of coffee).
No rigid systems.
No productivity guilt.
No gold-star productivity contests.
Just honest, flexible, actually doable planning that fits your life — messy, unpredictable, and all.
That’s what The Planning Club is here for.
Who is Planning Club really for?
- If you’ve ever sat at your desk wondering how the hell am I supposed to do this all — welcome home.
- If you’re done with “productivity hacks” that only make you feel more overwhelmed.
- If you’re ready to ditch the guilt and actually enjoy your work again.
- If you want planning to feel like a supportive ritual — not a performance or a stress test.
- And especially if you want a crew that gets the messy, beautiful chaos of life and business.
Then Planning Club is your new favorite group chat — where plans get made, messes are welcome, and no one’s pretending to have it all together.
Who will you meet?
Whether you’re running a busy shop, freelancing, leading a remote team across time zones, juggling school pickups with client calls, recovering from burnout, or just done living in catch-up mode — you belong here.
Our members know life never fits into neat boxes — but that doesn’t mean your big goals have to wait. They care about their work and their wellbeing, and they get that rigid plans that ignore real life don’t work.
They’re building sustainable, life-first businesses—and they’re not afraid to say, “I’m figuring it out too.”
Try it risk-free. You can cancel anytime—no guilt, no weird vibes.
What you won't find here.
No 5am miracle routines.
No toxic "push harder" energy.
No systems that fall apart the minute life throws a curveball.
No tech that takes longer than the task.
No pretending your toddler isn’t climbing on your back while you’re on a client call.
No fake hustle culture shiny objects filling up your head and your bank account.
This isn’t about doing more.
It’s about doing what matters. Without the noise. Without the overwhelm.
Just a little bit of planning, a whole lot of support, and a community who’s got your back.
Planning Club isn’t just a cute idea. It’s a structure that helps you follow through.
It isn’t a “someday when things calm down” kind of thing.
It’s how you start moving forward now, with the time, energy, and capacity you actually have.
You’ve been holding so much—and doing more than most people ever see.
If you’ve ever said:
“I just need someone to sit with me and help me figure it out…”
That’s exactly what Planning Club does.
Structure and support, without the overwhelm.
You don’t have to carry it all alone. Let’s plan your month together.
Try it risk-free. You can cancel anytime—no guilt, no weird vibes.
What's included in Planning Club?
This isn’t a membership that adds more to your plate—it’s built to respect how full your plate already is.
Every session has a clear purpose, fits into a predictable monthly rhythm, and is designed to help you get traction without requiring hours you don’t have.
You can show up exactly as you are, use what you need, and skip the rest. It’s flexible, lightweight, and made to work with your real life.
Weekly Sessions
FIRST MONDAYS CO-PLANNING
Join us live to map your month. No prep. No pressure. You show up, and we guide you step-by-step. No decision fatigue, no blank stares—just grounded, supportive planning that fits your life.
ALL THE OTHER MONDAYS CO-WORKING
This co-working call is your focused pocket of time to stop circling the task... and actually do the thing. (Because without it? Life takes over. Every time.)
Club calls will be on Mondays @ 9am (SA Time) + 11am (EST
Quarterly sessions
PLANNING WORKSHOPS
This isn’t just about staying afloat from one Monday to the next. Planning Club gives you space to come up for air, zoom out, and chart your course—without needing a silent retreat or a vision board covered in gold foil quotes.
Throughout the year, we host signature Plan Along sessions that help you reflect, reset, and refocus—so you’re not just reacting to your calendar, you’re reclaiming it.
Replays are available for planning sessions.
Replays are available for planning sessions.
And there's more...
POP-UP EVENTS CLUB CONVERSATIONS
Optional drop-in sessions for deeper connection and reflection. Gentle check-ins focused on reverence and support for the human behind the business.
community CRACKING GOOD COMMUNITY!
A community of fellow business owners and freelancers who get the chaos — sharing wins, struggles, memes, and virtual high fives. A place to breathe, laugh, and remember why you started your business in the first place.
RESOURCES PLANNING TOOLKIT
Reusable monthly calendars, weekly + daily pages, and a habit tracker—undated so you can use them again and again. Nice to have - but not essential for the calls, you do you!
COMMUNICATION PRIVATE COMMUNITY CHANNEL
No clunky platforms. No extra logins.
We use a private Signal channel (it's an app, yep, it’s free) so you can stay connected without adding to your digital overwhelm. Drop a voice note or text whenever it works for you—on a walk, between calls, or hiding from your inbox. It’s low-maintenance, no-pressure, and designed to fit into your real life, not compete with it.
Let’s be real—life’s not slowing down anytime soon.
The world is loud.
Your inbox is relentless.
And no, pushing yourself harder won’t fix the overwhelm.
Planning Club is where you pause the noise and plan—on your terms.
(Lock in this rate for life — because who wants to pay more later for something that actually helps?)
Got questions?
Have another question?
Pop a message through to ashley@theashleyknightcompany.com