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How to Plan a Mid-Year Business Retreat to Get Your Goals Back on Track

Hailey Dale


I’m Hailey – content strategist and founder here at Your Content Empire where we help you create more profitable, purposeful and productive content — and hopefully enjoy yourself more while doing it too. Learn more about me here >>

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How to Plan a Mid-Year Business Retreat to Get Your Goals Back on Track

Are you in need of a business retreat?

Are your goals feeling a little stale? Yep, it happens. 

Who we were when we set them and who we are when we’re attempting to implement them can sometimes feel like completely different people. Jekyll and Hyde-esque.

That’s exactly why I like to take a mid-year business retreat – to refresh, renew and recalibrate my goals for the second half of the year. I’m a big fan of taking solo business retreats to reflect on the recent past, look forward to my next 6 months and come up with some solid plans to move towards reaching my business goals. From launch plans to content strategies, I walk away with a renewed passion for business and a can’t-wait-to-get-started-again attitude. These retreats don’t always look the same.

Some years, I’ll take advantage of having the house to myself for a weekend, stock myself up with treats, delivery menus, and a billion post-it notes. Other times, I’ll book a local AirBnB for a couple of nights and revel in the break from normal scenery (and room service, plenty of room service).

Here’s the 4-1-1 on my agenda for the mid-year business retreat

Mid-Year Business Retreat Step 1: Measure and Reflect

First up, I start with gathering the data.

I grab numbers from: 

Then I analyze what the numbers mean because just collecting them is barely scratching the surface of what people mean when they tell you to “know your numbers.” We need to take things a step further and reflect on what those numbers represent—growth, decline, opportunities, something we need to fix?

Here are the questions I answer every quarter before creating my next 90-day plan:

Sales & Revenue Reflection Questions:

  • How many sales did I make this quarter?
  • How much revenue did I earn this quarter?
  • What were my expenses this quarter?
  • What was my profit this quarter?
  • How much did I sell of each offer type?
  • How many free consult calls did I take?
  • What was my “close” rate for service packages?
  • For each offer – how many people visited the sales page?
  • For each offer – what was my conversion rate?
  • What offers should I focus more on? Why?
  • What offers should I focus less on? Why?
  • What new offers should I test out?

Content Reflection Questions:

  • What was my website traffic – total and unique?
  • Where did that traffic come from?
  • What social media platforms were most effective and enjoyable?
  • What blog posts did the best?
  • What opt-in freebies did the best?
  • What were my subscribers and conversion rates for each?
  • Email list subscribers?
  • Growth?
  • Open rate?  Best subject lines?
  • Click-through rate?

Team Questions:

  • How much did I pay for each team member?
  • What was my effectiveness in utilizing them?
  • Improvements or adjustments to make?
  • Any new positions or tasks to add or delegate?

Project Questions:

  • What projects did I complete?
  • Which are still outstanding?
  • What were the roadblocks?

Goals Questions:

  • What goals did I hit?
  • What goals did I miss?
  • What goals should I continue on with?
  • What goals do I not care about anymore? (Drop them)

Summary Questions:

  • What were my wins from the past quarter?
  • What were my challenges from the past quarter?
  • What am I changing in the coming quarter?
  • Where are my opportunities for the coming quarter?
  • Where did I maybe waste money?
  • How can I love on my community more this quarter?
  • If I could take on any goal and be guaranteed to succeed, what would I go for?

Mid-Year Business Retreat Step 2: Goal Refresher

Begin with what’s going on big picture in your business before diving into the details. I start with a calendar and put in my big events, launches and things I know are happening in my business and life.

I always do this first because when I don’t, I either (A) get overly ambitious with all the projects I couldn’t reasonably get finished; or (B) plan projects that make no sense with what else I have going on. Neither of which set me up for success.

Once those are in there and with the info I’ve gleaned from before, I ask myself:

  • What goals did I set for this year?
  • How much progress have I made? 
  • Between where I am now and where I want to be at the end of the year, what’s the gap?
  • What actions can I take in the next 6 months to complete them?
  • What actions and projects can I focus on for the next 90 days to make progress on them? 
  • Are they any new goals that I want to add? 
  • What does my ideal business look like? And what are some things I have to do to get me closer to that vision?

Then after answering these questions, I have an updated list of goals that I set aside before taking a quick break. 

Mid-Year Business Retreat Step 3: Action = Satisfaction

Once I’m refreshed, it’s time to start building out action plans.

First, I check in with my goals and make sure they’re still jiving with me.

Then I build out my projects and content strategy around these goals and events using my Annual Content Planning Kit.

Mid-Year Business Retreat Step 4: Work the Plan

A plan will only ever work if you actually use it. Here’s how I use my plan:

  • On a monthly basis: I add new projects to my task management tool (Asana)
  • On a weekly basis: I use the plan to create my weekly milestones and priorities

Time to Get Back on Track

When you start planning your mid-year business retreat, begin by measuring and reflecting and then get refreshed on your goals. Once you know where you’re at with your goals, you can start making an action plan. Of course, no action plan will be successful unless you actually work it, so make sure you follow through! 

Knowing the four steps to executing your mid-year business retreat successfully will help you refresh, renew, and recalibrate your business goals for the second half of the year.

And if you want the templates to follow-along with me as we go through the planner, grab the Content Empire Planner here ↓

Your Content Empire - Content Empire Planner and Digital Planning Bundle

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