How to Plan Your Own Quarterly Planning Retreat for Your Business (Free Checklist Inside)

If you’ve been following along in this blog series, you already know why I took a 40-hour quarterly planning off-site retreat, what I packed, what I journaled, and what I’ll do differently next time.

But maybe you’re still wondering, “Could I actually pull this off for myself?”

The answer is yes. And you don’t need two nights in a hotel to do it.

This post gives you a simple checklist and action plan so you can run your own CEO-level retreat. Whether you have 2 days away or just a Saturday morning with no interruptions, this guide will help you make it happen with intention.

The result? A business owner who is more calm and focused. A business that is more cohesive and strategic.

Ready to scale?


What to Do Before Your Retreat

A successful retreat starts before you ever open your laptop.

Here’s what I recommend doing ahead of time:

  • Block it off on your calendar and treat it like a non-negotiable appointment
  • Communicate with your family or team so you won’t be interrupted
  • Choose your location and make sure it has space, light, and quiet
  • Prep or pack all your food, snacks, and drinks in advance
  • Print your documents ahead of time so you’re not stuck scrolling tabs
  • Bring cozy clothes, backup chargers, and your go-to pens and notebooks
  • Know your focus. What’s the main thing you want to walk away with?
  • Create blocks of time and goals for those blocks of time to keep you focused and steady
Picture of pages and packets spread across a desk for a small business owner's quarterly planning retreat

What to Do During Your Retreat

You don’t need a minute-by-minute itinerary, but you do need some structure.

Here’s a simple framework you can follow:

Block 1: Reflection

  • Journal about last quarter
  • Look at what worked and what didn’t
  • Look for lessons learned
  • Review KPIs, revenue, client feedback, time use

Block 2: Vision and Goals

  • Reconnect with your bigger vision (your 1-year and 3-year goals)
  • Set goals for the next 90 days
  • Align them to your season of life, not just business metrics

Block 3: Strategy

  • Outline major projects or offers
  • Map out a high-level content plan 
  • Plan one bold move to stretch you

Block 4: Clean Up and Reset

  • Tidy up your task list and systems
  • Clean up your digital workspace or Notion
  • Decide what gets postponed, simplified, or deleted

If you only have a few hours, just pick one or two of these blocks and focus hard.

Picture of a water bottle, pens, stapler, gum, and other office supplies on desk for business owner's quarterly planning retreat

What to Do After Your Retreat

Coming home is the tricky part. It’s easy to go right back into chaos and lose your momentum.

Here’s what I suggest:

  • Add your new projects and plans into your actual calendar
  • Set a 30-minute CEO check-in every Friday to look at how you’re doing with your quarterly plan and to revisit your notes from your quarterly planning session
  • Build your action plan into your next 13 weeks (the length of a quarter) to ensure that the decisions you made and goals you set actually get done
  • Get an accountability partner

This retreat is not just a reset. 

It’s clarity and structure + a plan of action.

One of the things I did when I got home that was sooo helpful? I made myself a cup of tea and just sat down on the couch. No phone. No computer. I just sat there and gave myself an hour to “come down” from the mountain. I reflected. I further untangled some things. I thought about what was next. 

It was the perfect “re-entry” plan after my 40 hours away. 

Picture of a woman holding a mug on a couch with notebooks for a business owner's quarterly planning retreat

Quick Wins if You’re Starting Small

  • Start with just 3 hours for your first quarterly planning session
  • Use a free room at the library or coffee shop
  • Print only your top 3-5 documents
  • Do it at home but plan it like you’re leaving town

It’s not about the location. It’s about the intentional time to think and work on your business like a CEO.

People like to throw around the phrase “think like a CEO” but they have no idea what they’re talking about. Having worked alongside CEO’s in 7, 8, and yes, 9-figure businesses, I can tell you that thinking like a CEO is not checking email or reviewing to-do lists. 

What they do is what this series is about: they rise above the business, looking down at it objectively, logically, and strategically. 

They think about what has happened, where the business is going, and what they want for its future.

It’s powerful stuff if you’re willing to do this for your small business. 

Naturally, this doesn’t make sense for the hobbyists. For the woman whose business loses money for the family instead of paying off cars, student loans, and mortgages.

But if you’re like the Proverbs 31 woman (industrious and incredibly profitable in your business), then this series will change your business and your life. 

If you’re running a 6-figure business or close to it, I recommend you get away for these retreats whenever possible. Your brain behaves differently when it’s outside of its routine.


In Case You Missed It:

• Blog 1: Why I Took a 40-Hour CEO Retreat and How I Structured It
• Blog 2: What I Packed for My 40-Hour Quarterly Planning Retreat (Includes a freebie!)
• Blog 3: Journaling Prompts I Loved (and the Ones I’ll Never Use Again) (Includes a freebie!)
• Blog 4: What I Loved and What I’ll Do Differently Next Time for My Quarterly Planning Retreat


Want Extra Support?

Want a packing checklist for your retreat? It’s free! Click here to grab it!

If this retreat breakdown helped you realize you need more clarity, more systems, and a plan that doesn’t rely on hustle, you’re not alone.

Inside KPI Strategy Made Easy, I show you exactly how to track the numbers that matter so you can make better decisions every single week. Click here

And if you’re ready for full support (as in the coaching, accountability, structure, and a community of women walking the same path), the doors to The Success Squad open again soon. Click here

In the last blog post of this series, I’m breaking down how I brought God into my quarterly planning retreat. As a Christian business owner, I believe I don’t make decisions and plans on my own. There were some beautiful moments of my quarterly planning retreat that I want to share with you next time. I hope you check it out.

Hello, I'm Kelly!

A latte-loving, polka dot and stripe wearing business coach. I’m mom to 4 wonderfully quirky, sarcastic, competitive, driven, and hilarious kids (plus 2 kids-in-law) and happily married to my rock-solid husband for 25 years. While I frequently spill food on myself and can never seem to find my iPhone, my dedication to helping women like you reclaim their time and thrive in their business is unstoppable. 

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