Plan your best year ever. Start with an honest look at this one.
A self-paced planning retreat for established, service-based business owners. Step out of the day-to-day, look honestly at the year you just had, and leave with a 12-month plan built on what’s already working.
It’s time to stop starting over and start stacking wins.
Most planning only looks forward: what to create next, what to launch next, which strategy to try next. So every December it’s tempting to open a fresh notebook and plan a brand new business. Then client work takes over, life shows up the way it always does, and by February you’re back to reacting week to week.
It’s not a discipline problem. The plan was built forward without ever looking back, so it can’t tell you what to keep, what to drop, or what this year was quietly trying to teach you.
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You know you need more than Big Hairy Audacious Goals.
Most goal setting is all about creating something new. The issue? You’re always starting over.
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You’re ready for real momentum.
For a small business, that means building and running systems that stack wins.
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You need more self-accountability.
Without a process to hold yourself accountable, you’re back to winging it within weeks.
“I thought I wasn’t good at planning. I’ve realized that yes, I can plan and I can actually enjoy putting pen to paper and making my ideas real.”
Christie Pearl, CEO Retreat attendee
You’re not behind. The plan was written for a version of you that doesn’t exist.
Most plans quietly assume a CEO who works a perfect, uninterrupted 40 hours a week. She never gets sick, never gets the call to pick up a kid early, never has a parent who needs her, and somehow never takes a vacation. That woman doesn’t exist. The one running your business has interruptions, low-energy days, and people who count on her. Your real capacity is what decides whether you follow through, so that’s where this plan starts.
What the CEO running this business actually needs.
Room to think.
A day or two away from client work, so you can see the whole business instead of the next fire.
A plan built on what worked.
Decisions that come from your own numbers: which offers paid the bills, where your last ten clients came from, and what quietly drained your time.
A salary that’s designed, not leftover.
The salary your life needs and the revenue it takes to fund it, instead of paying yourself whatever remains after expenses.
A process you can repeat.
The same steps every year, so each review builds on the last and your business gets easier instead of starting from scratch.
A year that fits on one page.
Time off goes on the calendar first. Then your promotions, then the monthly marketing that keeps your pipeline full while you serve clients.
So let us introduce
The Annual Planning Retreat.
The planning process Racheal has refined for nearly a decade, rebuilt as a retreat you take on your own schedule. It walks through the past, present, and future of your business, in that order, so your goals come from what’s real instead of what’s shiny.
5 sessions5 workbooksGet Paid Calculator includedYour 12-month plan
Here’s what you’ll do.
Where you have been
Your Year in Review
Review the tape month by month: what revenue came in, what drove it, and what you were actively promoting. Then name what worked, what flopped, and what got in your way. Do this every year and the patterns start to show.
Where you want to go
Your Painted Picture
Follow your future self through an ordinary day a year from now, and decide the upgrades you want in your lifestyle, relationships, health, hobbies, and business. Next December, you’ll see which ones happened and which got pushed aside.
Where you are now
Your Business Design
Define success on your terms, get specific about your dream clients, and use the Get Paid Calculator to work out what your business needs to pay you and what that takes in revenue. Then review every offer line by line.
What to focus on
Your Client Growth Engine™ Goals
Audit how clients find you and say yes across Attract, Engage, Nurture, Invite, and Delight. The gaps keeping your revenue unpredictable become your goals, and you narrow everything down to five.
How the year runs
Your 12-Month Action Plan
Time off goes in first. Then when you’ll sell your signature offer, your client upgrade and entry offers, audience building, and the monthly marketing that keeps you out of feast or famine.
The results you’ll walk away with.
Five things most business owners never put on paper, ready before the new year starts.
- 1A clear keep-and-stop list built from what actually happened this year.
- 2A personal salary target tied to the life you want next year.
- 3A revenue plan where your offers, prices, and capacity add up.
- 4Five goals that close the gaps in your Client Growth Engine™.
- 5A 12-month action plan with time off, promotions, and marketing mapped month by month.
Planning isn’t another chore. It’s CEO work.
This is a retreat, not another challenge or workshop. The most powerful thing you can do for your business is give yourself permission to step out of the day-to-day and think about what you want to build next. You can’t do that justice in a one-hour block.
So treat it like a client meeting you would never cancel. Put the days on your calendar and go somewhere your to-do list can’t follow you. It doesn’t have to cost a thing.
Racheal takes herself away for a couple of days every year to do exactly this. For years, that meant booking a private room at the library.
Ten years of women coming back every December.
They return because the process works better each time they run it. Here’s what they say about the planning that this retreat is built on.
“I’ve literally opened it every single day to make sure I’m still on track and to help me avoid my shiny object syndrome.”
“Sometimes we think that one thing is one thing when it’s really 20 things.”
“I left with a real plan, like a real tangible thing where I said, okay, I can go home. I can hit the ground running.”
“I’ve literally opened it every single day to make sure I’m still on track and to help me avoid my shiny object syndrome.”
“Sometimes we think that one thing is one thing when it’s really 20 things.”
“I left with a real plan, like a real tangible thing where I said, okay, I can go home. I can hit the ground running.”
“I was able to reconnect with my preferred schedule, which is something that has gotten lost over the last few years of being in my business.”
“I don’t need to have 10 ways of attracting clients, but having one way that works is definitely enough.”
“You literally walk away with your 90 day plan, and all the worksheets and tools that Racheal provides are so valuable. I still refer to them to this day.”
“I was able to reconnect with my preferred schedule, which is something that has gotten lost over the last few years of being in my business.”
“I don’t need to have 10 ways of attracting clients, but having one way that works is definitely enough.”
“You literally walk away with your 90 day plan, and all the worksheets and tools that Racheal provides are so valuable. I still refer to them to this day.”
From CEO Retreat attendees.
How it works.
Get instant access.
The sessions, workbooks, and Get Paid Calculator are ready the moment you check out.
Book your retreat days.
Put them on the calendar like a client meeting, and pick the place where you’ll do your best thinking.
Work through five sessions.
Each one builds on the last, from the year behind you to the year ahead.
Come back every December.
Run the process again with a year of better data behind you. That’s how the wins stack.
Meet Racheal Cook, MBA.
Founder of The CEO Collective® and creator of the 90 Day CEO Operating System®. Before starting her own business in 2008, Racheal facilitated strategic planning retreats for executive teams. She rebuilt that process for women running service-based, relational businesses, because the corporate version assumed 52 uninterrupted weeks, a finance department, and nobody at home who needs you.
For more than 10 years she taught it as the free Plan Your Best Year Ever challenge. Well over 10,000 women have gone through it, and many come back year after year to compare what they planned with what happened. She still runs it on her own business every December.
Make 2027 the year you build on what’s working.
Instant access to the 2027 edition. Block your retreat days, work through the sessions, and keep them for as long as you like.
Joined the free challenge in a past year? Watch your inbox for a returning-participant rate.
$97
One-time purchase · The 2027 edition, yours to keep
- ✦Five recorded planning sessions taught by Racheal
- ✦Five session workbooks
- ✦The Get Paid Calculator ($47 value)
- ✦Your finished 12-month action plan
Made for high-trust, relationship-driven, service-based businesses.
This is for you if
You run a service-based, relational business, like a consulting firm, design studio, therapy or clinical practice, accounting or financial practice, or coaching business.
You have loyal clients and offers that already sell, and you want next year to build on this one.
You want your business to pay you a steady salary that funds the life you want.
You’d rather plan your business around your life, including the kids, the parents, and the seasons you can see coming.
It’s probably not for you if
✕ You sell physical products. The revenue and sales planning are built for service businesses.
✕ You’re looking for new marketing tactics to try. This retreat helps you decide what to keep doing.
✕ You want someone else to write your plan for you.
Frequently asked questions.
I'm already stretched thin. Do I really have time for a retreat?
That’s the reason to do it. The retreat is split into five sessions, and each one takes about 30 minutes to an hour with the workbook, so you can finish a session in one sitting. Ideally, you work through them one at a time: finish a session, get up, take a walk, give your mind a break, then come back for the next. If short bursts are all you have this week, it works that way too. The hours you spend here are the ones that keep next year from running you.
Do I have to go somewhere?
No, but it helps. Anywhere that gets you out of your usual workspace works: a hotel, an Airbnb, a library room, a coworking desk, or a coffee shop. What matters is protecting the time like you would for a client.
Will this work for my kind of business?
It’s designed for service-based, relational businesses: consultants, designers and agencies, therapists and clinicians, CPAs and financial professionals, coaches, and health practitioners. If your revenue comes from client relationships, it fits.
Is this the same as Plan Your Best Year Ever?
It grew out of it. Same core process Racheal has refined for nearly a decade, now a complete retreat with the Get Paid Calculator included.
How long do I have access?
You get the 2027 edition of the Annual Planning Retreat, and it’s yours to keep for as long as you want. Racheal updates the retreat every year, and future editions aren’t included. This is a one-time purchase of this year’s version.
You don’t need a brand new business next year. You need a plan that builds on this one.
The CEO Collective®
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Results vary. Completing this retreat produces a plan, not a guaranteed income. © 2026 The CEO Collective®