Think Weekend started as a vague idea over a few text messages between two friends a little over four years ago. No formal plans made. No set agenda. Very little detail discussed in advance. But the unsaid understanding was that we both needed a weekend to reflect and reset. In fact, any questions ultimately discussed that weekend were jotted down hastily while en route to our destination.

The questions covered topics ranging from daily routines and bad habits to career goals, family relationships, and internal struggles. The point of the weekend was to talk, to think, to feel, and to wrest some control over our lives by getting away from the daily grind, the small but real anxieties, and the rather big sources of stress. Our goal wasn’t to solve any problems explicitly, but we wanted to at least consider them from a newer angle at a slower pace.

The weekend was an unquestionable success, but not based on any scientific metrics or other hard proof. Instead, it was about how we felt internally and in terms of a stronger connection with each other. In the process, we both moved a step or two closer to manifesting eudaimonia, a Greek word for which the closest translation in English is flourishing, and is often connected to the concept of the good life. Think Weekend is for people who seek the good life, and when done right, it’s a way to both experience that concept in the moment and make progress toward it in a longer-term sense.

A tradition was born. Since that first Think Weekend, we’ve held one every year, with the group size ranging from two people to six. Sometimes we add a new wrinkle like an individualized question or a new “Thinktivity.” Adding a friend who wasn’t inclined to just pat us on the back for our first answer to a question emphasized the value of opponent processing in these types of conversations.

As more of our friends heard about it, we got a request for a written explanation of how to “do” Think Weekend. Writing out that simple explanation was a revelation, and it left us asking, “What if we could find a relatively easy way to help more people experience Think Weekend?”

Emphasis on “relatively” easy. We started with a good set of thoughtful questions and set out to create something that anyone can take off the shelf and start to use within minutes. Over the past year, while juggling a full-time job and a growing family, we’ve learned more about packaging and shipping and color codes and board game design/testing—not to mention how to take feedback—than we’d ever imagined. (And to be clear, we still have A LOT to learn.) We’ve reached out to game makers and survey experts and people with much deeper creative backgrounds than us and even asked random strangers for their input. We’ve lost count of the number of late nights and long hours and product iterations.

Now we’re finally ready to share Think Weekend with you, in a box (where you can leave your phones) that has Guidance Cards to help get you started, 40 prepared Question Cards, and blank cards in case you want to write your own questions.

Think Weekend is made in Greece—the birthplace of eudaimoniareflecting our heritage and the value we place on good, meaningful conversation at the pace of people connected to the moment.

We can’t wait for you to try it and hear how you make it your own.

Frequently Asked Questions

How does Think Weekend work?

Gather your group, pick some question cards, and let conversations flow naturally. We’d suggest 5–15 questions per session—on the lower end if just doing 1–2 hours, more if doing a whole weekend.

Do we have to answer every question?

Definitely not. We’d suggest 5–15. Pick what resonates and let conversations find their own depth.

Do we go around in a circle to answer each question?

Let conversations flow naturally — just make sure everyone gets a chance to answer each question.

What if someone dominates the conversation?

Set and enforce ground rules as needed to leave time for everyone to respond fully to each question.

Do we need a moderator?

Not officially, but someone should keep track of the questions you plan to cover and move conversations along as needed.

Phones allowed?

You decide — but the box fits several phones for a reason.

Is this activity totally serious or intense?

No. Some questions go deeper, some don’t. You should leave room for plenty of fun and other quality time alongside the conversation.

What if we can’t do a whole weekend?

Any extended block of time discussing these questions — while limiting distractions — will work well. An evening, a road trip, a long dinner. The more present you can be, the better.

Can we add our own questions?

Yes! Send your favorites to ideas@ThinkWeekend.us.

Can we do this more than once?

Yes! Our original group does it annually, discussing some old and some new questions each time.

Will this change my life?

Maybe! Either way, we’re confident it will foster more thoughtfulness, purpose, self-understanding, and connection.

What else should I know?

We recommend a full weekend (hence the name!) so you can dig into the experience. But feel free to start smaller with a Think Night, Think Coffee, Think Walk, or Think Day at the Park.

How many people do you need?

Think Weekend works with as few as 2 people or a group of up to about 8. Larger groups can split into smaller conversation circles.

What ages is Think Weekend designed for?

Think Weekend is designed for adults (18+).

Have a question we didn’t answer? Feel free to reach out.

hello@ThinkWeekend.us