What Every Great Retreat Has in Common

As a kid, I LOVED a good retreat weekend. The opportunity to get away with friends, leave the city, and spend time having adventures (and getting into a bit of trouble) was fantastic. As an adult, I love retreats for different reasons: they’re a break from the routine, a chance to slow down, unwind, and actually put my phone away.

That’s why, when an old friend recently asked me for advice on planning a retreat, I was happy to help. What follows is a taste of the ideas I shared with her, and I hope it helps some of you recapture the joy and excitement a weekend retreat can bring.

Step #1 – Define the Purpose (Scope)
It’s really important to understand the scope and purpose of your retreat as you start planning things out. The length, time, and location matter, for sure, but so does the heart of why you’re getting away. Some retreats are about rest and building deeper relationships. Others are about spiritual growth, or maybe it’s about getting a group of like-minded people together to have fun and go deeper. You have to understand the scope of what you’re trying to do first because it’s the foundation on which everything else is built. Here are some key questions to ask as you start planning:

• Who is this retreat for?
• What will we be doing?
• Where/When will this retreat happen?
• Why are we doing this? Or why are people paying to come?
• How will this retreat look?

Step #2 – Block Out the Big Picture (Rough Plan)
The rough plan, for me, is the most important part of the planning process. I like creating what I call a rundown. Think of this as identifying rough blocks of time for something to happen in. The details don’t matter as much as roughly when they will happen. This is important because it helps me know I can get all the key pieces together within the scope of the plan. Once I have this together, I start building out the details.

Here is a rough example of what this could look like at a typical weekend retreat:

Friday
Arrive / Get Settled
Welcome + Session #1
Social Space + Snack
Lights Out

Saturday
Team Meeting
Breakfast
Session #2
Breakouts / Group Time
Lunch
Afternoon Activity
Free Time
Dinner
Session #3
Social Space + Snack
Lights Out

Sunday
Team Meeting
Breakfast
Session #4
Clean-up
Goodbyes

Once I have a structure like this, I would fill in some of the bigger details based on the retreat. So if it’s a Youth Retreat, there might be a night game. If it’s a Men’s Retreat, maybe it’s morning activities and afternoon sessions. If it’s an Alpha weekend, there might be two afternoon sessions and a social/game time in the evening.

The point is you want it in blocks of rough time.

Step #3 – Add Structure, Not Micromanagement (Details)
The next part depends a bit on you and how you’re wired. Once you have your plan in place, it’s time to fill in the details. The bigger the retreat or the more moving parts, the more details you need. I used to do a Grad Retreat, and on the Saturday afternoon from 2–5 p.m. was “Free Time,” and I intentionally was light on details. The goal of the retreat was to build community and rest, so I let them decide in the moment. However, you can’t give Jr. Youth students three hours of open time — that’s a recipe for chaos. But you also don’t want to plan every minute.

Step #4 – Build a Team (Share the Load)
You may not have a staff team, but the odds are high if you’re taking people on a retreat, you have a team of people supporting you in the process. Let them into the planning stages early and share the load of the work. Get them to work out the details for their block of time, or get people to share the spotlight while you or someone else is setting up the next thing.

It is important that someone be the Event Leader or Primary Point Person. They are the one to call the shots and make the final decisions. But there are often so many moving parts at a retreat, it’s important to have a team to share the load with. Pro Tip: The point person should be thinking 30 minutes faster than everyone else. By that I mean they should be thinking about what comes next in the schedule and making sure the right people are ready for the next thing.

Step #5 – Plan to Pivot (Flexibility)
This is a reminder that retreats rarely go smoothly or according to plan. Things run over time and push at buffers of time. Wide games are canceled due to rain, the power goes out, and someone needs a ride to the hospital, etc. Anything can happen when you take people out of their normal routine. So be flexible and be willing to have your schedule as a “guide,” not a rule.

This is also one of the reasons you shouldn’t overpack your time. At a minimum, I don’t think any retreat I have ever run in almost 25 years has ever been on time. Eventually, we always get behind, and I can force us to stick to the plan, or I can adjust my expectations and be flexible.

Bring It Together
I love retreats because they are an opportunity to break away from the usual and be intentional with our time. Relationships that could take months or years in a regular context can be jump-started by one late-night conversation at a campfire. Retreats can be simple and easy to run or be complex with tons of moving parts. Regardless of the size or complexity, my encouragement to you is to be flexible and plan a bit less than you think you need. I promise you the time will fill up, but instead of being filled up with programs, it will be filled up with people — and to me, that’s the magic of a retreat

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Fresh Challenge

You don’t need to have all the answers yet. But if you take 20 minutes this week to sketch out your purpose and a rough plan, you’re already on your way to something meaningful. Who knows? That idea in your head might become someone’s life-changing weekend.