How to Choose a Transformational Retreat: 5 Questions to Ask Before You Book

Retreats are having a moment, which means there are a lot of them out there, and the quality is all over the map. Some are genuinely life-changing. Some are a nice trip with a yoga class bolted on and a five-figure price tag.

Since 2021 I have invested over $100,000 of my own money into this world: retreats, coaching, courses. I have been the guest more times than I can count, and I now help facilitate them too. So I have seen what separates a retreat that changes someone's life from one that just makes for good photos.

Here are the five questions I would ask before I booked anything.

1. Who is actually leading it, and have they lived this?

The facilitator makes or breaks the experience. Look past the polished bio. Have they actually done their own work, or are they teaching from a certification they got last year? A good leader has been in the hard chair themselves. They can hold a room when things get real, manage group dynamics, and create enough safety that people stop performing.

If you cannot tell who is leading or what they have actually been through, that is your answer.

2. How big is the group?

Small groups change people. Big groups entertain them.

When a circle is small, there is nowhere to hide, in the best way. You get seen, you get heard, and the connections are real. Once a group gets large, it turns into an event, and the depth quietly disappears. I will always take a curated group of a dozen over a room of fifty. Ask for the cap before you book.

3. What does a day actually look like?

Ask for the schedule. Then look for two things: intention and space.

Intention means the days are designed, not random. Movement, nervous system work, real conversation, and time outdoors, in a flow that builds. Space means there is room to rest, journal, and just stare at the mountains. A retreat packed wall to wall is a conference. The breakthroughs usually happen in the gaps.

4. Does the location match the work you want to do?

Place is not decoration. Mountains, desert, jungle, and ocean each do something different to your nervous system. When I choose where to host, I ask what I want the landscape to evoke, and whether the place truly supports stillness and honest conversation, not just whether it looks good on Instagram.

Be honest about logistics too. The most beautiful spot on earth does you no good if getting there leaves you fried before day one.

5. What happens after you go home?

This is the question almost nobody asks, and it is the most important one. The high of a great retreat fades. What you do in the 30 days after is everything.

Ask whether there is any integration support: a follow-up call, a community, simple practices to take home, clear next steps. A retreat that drops you off at the airport with a hug and never follows up is leaving most of the value on the table.

The simplest filter of all

If your body says yes before your mind catches up, pay attention to that. And if a retreat cannot give you straight answers to the five questions above, keep looking.

If you want help thinking it through, that is genuinely one of my favorite things to do. Take a look at the retreats I am running this year, or tell me what you are looking for and I will point you toward something that fits, even if it is not one of mine. I am well connected to some of the best hosts in the world, and I would rather you end up in the right room than just any room.