What is a Quarterly Offsite, and How Do I Take One?

As I was preparing my 2020 vision, and reflecting on this past year, I was surprised at what I learned. But first, a little backstory:

This time last year, my wife and I were both frustrated with our relationship.

Intellectually, we knew we cared for each other, but neither of us were getting the attention or love language we needed. We were both feeling frustrated and “unseen,” like we couldn’t connect to each other in the midst of a busy life with two (now three) little kids.

It was incredibly draining, making it difficult to find motivation to do anything creative or entrepreneurial, slowing my business endeavors to a halt.

As my wife and I were reflecting on this past year, we realized (with a moment of shock) that right now our marriage is in the best condition we’ve ever experienced! We both feel loved, encouraged, and close to each other—but that didn’t happen by accident.

There are many changes we made this past year to prioritize our marriage, including introducing a weekly dinner date and a weekly lunch date to separate “heart talk” and “shop talk”, as well as meeting with a marriage therapist together.

All of these changes helped, but they were really the result of the biggest change we made at the beginning of the year: we started taking quarterly offsite retreats together.

What is a Quarterly Offsite Retreat?

A quarterly offsite retreat is exactly what it sounds like: a short retreat once per quarter that is away from your day-to-day life. Typically, the focus is some mix of reflection and goal-setting.

The concept has been championed by Greg McKeown, and I started going on a quarterly offsite retreat by myself a couple of years ago, after I read Essentialism.

When I was going alone I would take a full workday by myself and disconnect, which was helpful, but inviting my wife to join me was a game-changer in all the best ways. We will definitely maintain this habit for years to come.

Here’s a peek into the quarterly offsite action plan my wife and I use each year:

Step 1: Schedule Four Retreats Each Year

Once you’ve committed to taking a quarterly offsite retreat you need to put this on your calendar at the start of your year as a “big rock” and schedule around it.

It’s easy to put this off, and schedule just one at a time, but the risk that you’ll become “too busy” is too great. At a minimum, you’ll want a day and a half for an overnight trip, but if you can spare two nights away that’s even better.

Step 2: Book a Relaxing Location

Your quarterly offsite retreat doesn’t need to be an exciting adventure. You need a location that’s away from your day-to-day life where you can get plenty of quiet, open space in a comfortable environment.

This doesn’t have to be extravagant. We’ve gone as simple as an affordable hotel a couple of hours away—but when we’ve got a full Airbnb for two days that’s been the best-case scenario. We’ve enjoyed both a downtown studio and a cozy farmhouse retreat.

Step 3: Start with Rejuvenation

If you’re anything like me, you might be tempted to jump right into goal-setting because you’re excited to dream on your quarterly offsite retreat—but that would be a mistake.

First things first, you need to relax. My wife and I like to drop our bags at the Airbnb and then go out for the evening, with a special dinner at a new (highly-rated) restaurant and then a movie, followed by a good night’s sleep.

This rejuvenation practice acts as a critical transition, training your body that this is differentand allowing your mind time to unwind and disconnect from all the open loops left at home. This prepares you to wake energized, and have an effective focus day.

Step 4: Follow a Scheduled Agenda

It can be tempting to keep a lackadaisical approach for your quarterly offsite retreat, but your focus time is critical. We’ve found it helpful to keep an hour-by-hour agenda for the working day.

We have experimented with several different structures before we settled on using the Quarterly Preview worksheet from the Full Focus Planner. Our agenda looks something like this:

• 7:30 AM Breakfast
• 8 AM: Complete “My Biggest Wins” and share
• 9 AM: Complete After Action Review and share
• 10 AM: Review life plan (update as needed)
• 11 AM: Review annual goals (update as needed)
• 12 PM: Lunch
• 1 PM: Set new quarterly goals
• 2 PM: Review upcoming monthly calendars (discuss as needed)
• 3 PM: Review Ideal Week (update as needed)
• 4 PM: Review Daily Rituals (update as needed)
• 5 PM: Dinner

We don’t keep to that agenda exactly, but it helps us stay on track. Depending on the season, some sections may go quickly and some may require extra time.

Step 5: Start Wide and Incrementally Focus

If you glance back at that agenda, you’ll notice that even within a full day of dreaming we still Macro-dream, Micro-execute by reviewing our life plans before we get into annual, and then quarterly foals.

This needs to be incremental, because it’s tempting to jump straight from goal-setting to tomorrow’s task list. Instead, you need to go from annual to quarterly to monthly, and then focus on your weekly rhythms to create space for the daily productivity to come.

Should You Take a Quarterly Offsite Retreat?

It takes a bit of work to start the habit, but quarterly offsite retreats are the best solution I’ve found to creating a regular rhythm of rejuvenation and reflection, focused on improving your life.

This habit fits squarely within what Michael Gerber calls working “on” your business, as opposed to working “in” it (though you have the chance to extend this beyond your business, as I do).

If you can take quarterly offsite retreats by yourself, that’s excellent! If you can take them with your spouse, that’s even better. Start small, build the habit, and you can thank me later.

Question: What’s holding you back from taking your own quarterly offsite retreats?