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.

Last year (2016), I was feeling a little (ok, a lot) directionless in my business. I knew I had to make big changes and I was losing control of my time and my plans. I was the worker bee - constantly trying to catch-up and underpaid.

Last year I also participated in the The Planathon for the first time. I already knew of Amber and NiceOps - and the idea of taking a week to participate in a virtual retreat dedicated to actually planning out the next year and building systems around my business was incredibly appealing.

I love a good checklist and a good go-by (government-speak for a method/outline/system you can copy). I knew that I was flying by the seat of my pants most days, and I needed more breathing room to be the CEO.

Most “challenges” on social media tend to lose my interest after a couple of days. Not so with the Planathon. As the week went on, I was more engaged and interested - tagging people for accountability and watching as many videos as I could.

If you want to know more about my thoughts on The Planathon as an incredible social media campaign, read more here.

Part of business planning is to come up with your goals for the upcoming year. These should be measurable and specific goals, such as “grow my email list to 5,000”, or “sell $2,000 worth of services each month”.

When I sat down to create my business goals, a big one was to plan an actual business retreat in the fall of 2017 to plan for 2018.

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.

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.

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

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

  • 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

  • DSLR camera

  • Tripod and selfie light

  • A book or two (business and fiction)

  • Large wall-stick post-it notes

  • 2 or 3 notebooks

  • Paperclips to organize notes

  • Dry erase board w/ pens

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

So basically, I’m going 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. I offer tons of resources - like content planning and blog marketing, plus other tools to make entrepreneurship easier - in my Free Rockstar Membership for Pinterest PowerUp. PPU is a membership community for online entrepreneurs and the only Pinterest marketing resource you will ever need for your business!

cara chace

Hey hey, I'm Cara - Pinterest marketing evangelist and lover of all things Squarespace website design. I team up with online entrepreneurs to get tons of website traffic into sales funnels (marketing speak for getting eyeballs on your website and turning them into customers).

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