Crafting Our Ideal Future: A Couple’s Framework for Quarterly Off-Sites

At the start of each quarter, my wife Midori and I carve out two days from our hectic schedules for something we’ve come to cherish: our quarterly off-site. It’s become a ritual of reflection, planning, and alignment that not only keeps us grounded but also propels us toward our shared vision of the future. I’m sharing this framework because it has been transformative for us, and it might just offer some insights for others looking to create a more intentional life together.

Rough Agenda

Day 1: Reflecting on the Past

The first step in our off-site is a Calendar Look-Back (inspired by Tim Ferriss’s ‘Past Year Review’ exercise). We literally go week by week through our calendars from the past three to six months (depending on how long it’s been since our last off-site). The objective is simple: identify the moments that brought us emotional highs and those that dragged us into lows.

It’s a surprisingly powerful exercise. By the end of it, we each have a list of our top emotional highs and lows. But the real magic happens when we distill these into themes. What patterns emerge? Are there specific people, activities, or times of the year that consistently lead to joy or frustration? Once we have these insights, we make it a priority to optimize our next quarter—more of what makes us happy, less of what doesn’t.

Example of my quarterly lookback results, setting the stage to look for patterns/themes

We usually wrap up Day 1 by taking a tangible step toward ensuring more emotional highs in the coming months. It could be booking a trip, scheduling a meaningful activity, or planning something that we know will bring us joy.

Day 2: Designing the Future

With the past clearly mapped out, Day 2 is all about the future. We kick things off with a Vivid Vision exercise. Each of us spends 5-10 minutes writing down our ideal vision for the end of the year. Sometimes, we take it even further, envisioning what our lives look like three and five years down the road. The goal is to get as clear and detailed as possible about what we want, so we can reverse engineer the steps needed to get there.

After we’ve each crafted our visions, we share them. This is where the alignment happens. It’s always exciting to see where our visions overlap—those shared dreams that we can work on together. Once we’ve identified these, we start setting our goals for the next quarter.

We both use the 12-Week Year framework for goal-setting (from the book by the same name – an excellent read!), which emphasizes making a year’s worth of progress in just 12 weeks. I personally use the OKR (Objectives and Key Results) format for my goals, while Midori has her own strategy. The key is to set goals that are both exciting and trackable, ideally on a weekly or even daily basis.

I'll typically create an OKR-based scorecard like this in Notion to track weekly progress

Taking Action & Staying Aligned

Setting goals is one thing; making progress is another. That’s why the final step of our off-site is to chart out clear action steps for the next 12 weeks. Depending on the goal and how much energy we have left (because this process can be exhausting), we either outline a few key milestones or create a detailed weekly plan. This part ensures that we’re not just dreaming but actively moving toward those dreams.

To make sure we stay on track, we’ve set up a ritual of daily and weekly check-ins. These are moments to reflect on our progress, adjust if needed, and offer support to one another.

We also start Day 2 with some strenuous physical activity—a tough workout, a hike, or something else that gets us sweating. There’s something about working hard physically that sets the tone for working hard mentally. Plus, it’s a great way to bond and align our mindsets for the goal-setting ahead.

And of course, no off-site is complete without a celebration. After all the hard work, we treat ourselves to a nice dinner to mark the progress we’ve made and to toast to the exciting future we’re building together.

A recent post-offsite celebration dinner - in style! 🍷

The Power of Regular Reflection

We’ve found that doing this on a regular cadence—ideally every quarter, but no less than every six months—keeps us aligned and motivated. It’s a way to ensure that we’re not just reacting to life as it happens, but actively designing the life we want to live.

If you’re looking for a framework to bring more intention into your life, whether solo or with a partner, I highly recommend trying something like this. It doesn’t have to be exactly what we do (though it has served Midori and I well!), and even a simplified version or including some personal twists/quirks/idiosyncratic rituals unique to you and your partner can make a huge difference.

Here’s to crafting a life full of intentionality, joy, and shared purpose! 🥂