How To Plan a Business Planning Retreat

Sometimes in order to truly “see” our business as the CEO we need to take a step back and get away from it all.

Away from the emails, the instant messages and text, the home to-do list, the kids, the...well...everything that’s part of day to day life.

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If you’re a work-from-home entrepreneur - especially a parent - the work day can be a rat’s nest of stuff to do, both personal and professional. You do your best to plan your week and stay focused, but life inevitably happens and we tend to react to immediate needs of others.

Ideally, in the best of times, we carve out space for family-only days, self-improvement and education, and do our darndest to only check email a couple of times per day. But the edge of those spaces tends to get fuzzy and gray over time.

There are several years I’ve felt a little (ok, a lot) directionless in my business. I knew I had to make big changes to stop losing control of my time and my plans. I was tired of being the worker bee - constantly trying to catch-up and underpaid.

I went on my own business planning retreat for the first time in the fall of 2017. I was able to lock myself in a nice hotel room with an incredible view for almost 3 days to take stock of 2017 and plan for 2018.

It was incredible.

I went with a plan of action (use the free workbook for yourself) and got more done in that short amount of time than I thought humanly possible.

I’m a natural introvert who recharges by being left alone, so the idea of being alone in a hotel room for one or two nights to just plan and dream was absolute heaven. No running errands, no checking email, no kid-taxi service, no talking or being talked at. *le sigh*

I am in the middle of planning my retreat and as I’m creating my schedule and checklists, I want to share them with you so you can plan your own business retreat.

Taking a couple of days to devote to the bigger dream and plan for my business is now a non-negotiable.

Here’s how I map it all out…

Step 1: Decide On Logistics

Getting away for two or three nights is great, but one night or an entire day will do as well. If you cannot do a hotel night, finding a quiet place where you can hole up all day for a day or two will work - like a library or day spa.

Step 2: Make A List Of Work

Start a few weeks out with a running list of big items you need to work through or plan for the next year. These could be top-level items like creating an organization chart for all key jobs in your company (even if it’s just you), or more detailed like marking down all the hashtag holidays you’re going to create content for.

You should have a mix of big-idea CEO work (i.e. what are my core business values?), and smaller tasks you can do when you need to take a brain-break (i.e. organize my Google Drive and archive old files).

The work will likely fall into these categories:

  • Marketing (digital or otherwise)

  • Financial (P&L and forecasting)

  • Services (updates or re-working)

  • Products (updates)

  • Content (planning out blogs and promos)

  • Systems (workflows and processes)

  • Analytics (tracking and measuring)

In addition, I make learning and education a big part of my job as CEO. I would also include what you want to learn and read as part of your goals and calendar.

After you jot down and brainstorm this list - copy the final list of priorities and to-do’s into your Business Planning Retreat Workbook.

Step 3: Create A Schedule

Plan your time like you would get an itinerary at a conference. I’m serious. This will help keep you on track and take it seriously.

Like this:
10am - arrive at hotel, unpack, go for a walk.
11am - plan monthly content theme
12:30pm - lunch and journaling or reading
2pm - work on main email marketing automation sequence
4pm - organize client onboarding process
5pm - dinner
6pm - reading and journaling
7pm - list of books to read
...etc etc

There are 2 full pages in the workbook to create your schedule.


Step 4: Pack

You want your fun office stuff with you, as well as any business essentials. If you’re in a hotel room, hopefully it has a desk where you can work. If you’re in a close-to-home location, try to find a table or quiet area to yourself.

I’m an office supply junkie and I have a carry-on suitcase just for all the items I’m bringing to help me plan it all out.

Here’s a list of my essentials:

  • Laptop

  • Mouse (I hate the laptop trac mouse)

  • Earbuds

  • Webcam and Microphone

  • DSLR camera

  • Tripod and selfie light

  • All the chargers for all the things

  • Post-its in many different sizes and colors (I color-code my brain dumps)

  • Tons of colored pens and sharpies

  • My business planner

  • Year calendar

  • Large wall-stick post-it notes

  • 2 or 3 notebooks

  • Paperclips to organize notes

  • A book or two (business and fiction)

  • My own sparkle water and a bottle of champagne - because yes.

So basically, I go full-on “A Beautiful Mind” at my business planning retreat.

Step 5: Inform Everyone You’re Unavailable

Let your clients know you will be out of office. Let your significant other know you’re unavailable unless there’s an emergency. Delete your FB app from your phone. Turn your out of office responder on for your email.


You will not get nearly what you need to out of your planning retreat unless you focus and give yourself that time.

If you need an accountability partner (or a few) to help you keep your goals on track, join the community inside Pinterest PowerUp. We’re a membership community focused on Pinterest marketing, entrepreneurship, and productivity. Click to learn more.

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Hey hey, I'm Cara - the CEO of Chace Digital, a Pinterest marketing agency, and the Founder of Pinterest PowerUp, the first Pinterest marketing membership community designed for entrepreneurs. I love nothing more than seeing those light bulb moments with clients and members when they see how Pinterest builds their businesses... except for maybe a good book and another cup of coffee.

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