Issue #15

From start to finish: How to plan an in-person retreat your clients will love

Business Models
16 min read

A few minutes before nine a.m., attendees start trickling into the sun-filled great room, selecting their favorite seat– a couch with room to spread out for one, a deep, green armchair for another, and a straight-backed chair with ample table space for the next– arming themselves with coffee, tea, and pancakes, and gearing up to do something that they've traveled thousands of miles and spent dozens of hours getting hyped up for: taking a weekend to focus intensely on improving themselves.

If you've ever attended a retreat, whether for your business, yoga, or otherwise, you know that feeling. And the rush that comes at the end when you pat yourself on the back for accomplishing so much in such an incredibly short time.

The immersive quality of a retreat experience creates change and builds bonds that are hard to replicate in any other form.

But if you've ever considered holding a retreat in connection to your own online business, you've probably also experienced a very different feeling: abject terror of the unknown, like:

Common fears and doubts we'll help you tackle

  • Will anyone be interested at all?
  • Is this too expensive for anyone to consider?
  • How could I think I am qualified to talk to people for a whole weekend and have them think that's a worthwhile use of their money?
  • Will I just end up losing money because the venue and food and other speaker costs are too high?
  • If people even come, will they leave totally disappointed because they each didn't achieve the results they expected?

Over the last decade plus, I've attended many, many retreats, from those for small business owners or with a life coach to more unusual ones like retreats for professional singers or high-level field hockey players. And I've planned or helped plan many others. I've even written magazine articles for years that had me interviewing people who have special certifications and training in planning high-level corporate retreats.

So I can tell you that all of those fears are legitimate and can absolutely come true.

A total downer, I know!

But it's important to get them out of the way, because there are very real financial and reputation risks if you're not careful. We'll cover them all though, so you don't have to worry about things you didn't foresee creeping up and derailing your event.

So let's dive into how exactly you can put together a kick-ass event that will not only increase your income but also cement your relationship with your biggest and best customers.

Done right– as in, in a way where your budget runs positive–in-person  retreats can not only become your single biggest money-maker regardless of what you teach, but also become an invaluable customer-research mechanism, allowing you to put faces on your customers and their problems while getting paid to spend a few days hearing what your customers are struggling with and getting fresh ideas for new products to help fix those problems. (You even have a ready group to test those new tools and tactics on and get live feedback!)

The biggest hurdle in planning a retreat: Choosing a topic

Before you start thinking about the content side or the concept of choosing a topic, I invite you to step back considerably and ask:

What do you want from running retreats?

Do you want to:

  • Provide a premium experience for high-spend customers?
  • Offer a concentrated burst to those who want to tackle their issues quickly?
  • Simply give customers the opportunity for face time with you and others facing similar issues?

All of these aims lead to a different structure of your retreat, which in turn gives a framework to what topics may work for your event. Before even thinking about the topic, you need to consider:

What kind of retreat structure are you aiming for?

  • How many people you would be comfortable including, tending to, and feel responsible for the satisfaction of during the number of days you want to use for the retreat (a.k.a. the fewer the days, the smaller the group that you can realistically check-in with and work with)?
  • Whether you envision your event in a completely private space, such as a vacation home rental, or something more public like a hotel meeting room or even a co-working space (as having attendees all together all hours of the day is a very different experience with different results potential)?

Once you answer those two questions, you should be well on your way to envisioning what type of retreat you could happily and successfully put on.

Running an event, both on the ground and in the lead up, is very stressful, as is trying to sell seats. The best piece of advice I can give you is to begin with something that feels completely comfortable and doable for you.

What your customers will pay for?

Note: I did not say, “what they are telling you they want to learn.” Because if they won’t put a credit card down for that, it doesn’t matter.

If you are not sure what your customers’ number one pain is— or you don’t have any customers yet— find 10 people who seem like a good fit for you and what you might offer and write them and simply ask, “What would completely change your business (or life) to spend a weekend focusing on?”

Satisfaction guaranteed

That's the dream, right?

To tell your prospective attendees that they can be so confident in plopping down a frighteningly (for them— exciting for you) large gob of cash on something they don't receive right away and can't be sure they'll like.

There's two sides to the satisfaction coin when it comes to retreats:

  • Making them confident in it upfront (so they book)
  • Making them feel it at the end (so they both keep buying from you and tell their friends)

How can you make someone confident in buying something you have never offered that you might not even be confident about yet?

Promise a clear deliverable.

This is where I see a lot of retreats and intimate conferences get it wrong and then scramble to fill seats. Even (and for some reason, especially) top online marketers consistently get this wrong.

Conferences with 300 or 500 people and five tracks can attempt to cover a topic like “everything going on in X industry right now that you need to know!” but we all know that it’s pretty easy to leave those without having learned anything— or even being sure you attended the right sessions.

When you’re offering a small event, you must zero in on something that is achievable. In a weekend. (Or a week.)

Plan enough time for implementation.

Since attendees need time to work— to ensure they’ve actually accomplished something!— I recommend thinking of this as something you could cover completely in four to six hours of teaching. This gives you plenty of time to cover your material while incorporating plentiful exercises to give people an opportunity to practice implementing what they’ve learned, coming up with new questions and roadblocks, and getting those addressed so they are 100% ready to go when they get home.

It should be achievable.

Think of it like a promise you might make on a sales webinar, but that you will be including fundamental background, case studies, and guaranteed “finishing on site” about. It’s great it if also speaks to people's dreams for themselves. Operating on the power of daydreams of something better to pull one through the bland days leading up to departure is what powers most travel booking of any kind.

For our events, we use clear numeric markers in many cases (leave with 25 polished pitches or 100 article ideas matched to magazines), but you can also use an “all-done” approach, such as a weekend in which they’ll get their client-facing website done and off their plate, or create a short lead-generation e-book.

Offer an incredibly clear plan of how time will be spent.

This helps show that you know what you're doing on the front end, and helps people know if the event will be for them in terms of how they prefer to learn and how they are comfortable spending their time.

It avoids mismatches in style (both with you and among the attendees) and offers you a very clear checklist of what to do to meet attendee expectations.

Here's a downloadable sample schedule

We use for very small retreats that combine group sessions with one-on-one coaching:

Afternoon: Optional additional coaching time or free time to work in the house or make use of the library.
5:00 pm: Guests arrive, tour the property and amenities; reception with cocktails and snacks.
8:00 pm: Dinner, introductions. Module 1.

8:30 am: Breakfast
9:00 am: Module 2
10:00 am: Bathroom and coffee break
10:15 am: Module 3
12:00 pm: Lunch
2:00 pm: Module 4
3:00 pm: Coffee and bathroom break
3:15 pm: Module 5
4:30 pm: First round of individual one-on-one’s
7:00 pm: Dinner and socializing; you deserve a break!

8:30 am: Breakfast
9:00 am: Module 6
10:00 am: Second round of one-on-one’s
12:30 pm: Lunch
2:00 pm: Module 7
2:45 pm: Coffee and bathroom break
3:00 pm: Module 8
4:00 pm: Departure for guests not staying for additional retreat days (transport to afternoon bus back to New York City)

You can download the full schedule with all the workshop modules filled in here.

Make sure to finish with a collective experience.

This is something I've seen increasingly added to the schedules of small conferences, but in the retreat context it is of paramount importance.

You must have a final, full-group, collective experience in which everyone not only considers how they will build on this experience and where they will go from here, but also concludes their experience of the event.

Have every single attendee share, not just one-on-one to another attendee but to the full group, something that changed for them or that they accomplished during the event.

Locking down logistics and costs

Particularly when running your *first* retreat, once you've settled on the topic, keeping costs down is your single biggest concern.

For that first retreat, you're going to run into the most issues with sign-ups that you'll ever have. It will only get easier for future events, because there will be:

  • People who absolutely would have loved to attend your first retreat but simply had other plans already on the dates you selected.
  • People who would have loved to attend your first retreat but didn't have the funds and have been saving up so they can attend a future one.
  • People who simply weren't on board with you enough the first time to pull the trigger but will be wooed by the stories of the first successful event and excited for the next one.

All of this means that you need to make your first retreat stupid cheap so that it is easy for people to take a chance on an unknown…which also means that your budget will be very slim.

As a result, you need to keep an extra close eye on:

  • Including other speakers and paying for their travel (This doesn't mean you should ask others to do it for free; rather you should have fewer presenters and focus on the attendee experience the first go around. If you want to co-host, do a straight profit split…with the clear expectation that there are unlikely to be profits on the first event.)
  • The venue cost, which will be your single biggest expense and is incredibly easy to over-spend on especially when you are looking to impress and don't know how many people will buy-in
  • “Extras,” like schwag, activities that you have to pay for, materials for activities that you run, resorts or other venues with amenities

How to optimize your costs and logistics for your (first) in-person retreat

#1: Speakers

Including other “big draw” speakers in your first retreat can be a financial hurdle, but there are several workarounds:

  • Have speakers teleconference in for those sessions (not the best option, but can allow your other business friends to contribute without asking too much from them or your budget).
  • Organize the retreat more strictly around exercises that attendees do and then share the results of.
  • Invite attendees to do “open problem” presentations in which each shares something that they are either struggling with (and the group discusses fixes) or that they have found useful in relation to the retreat topic. You work with attendees in advance to curate the topics and guide them through their presentation and everyone gets an incredibly powerful chance to learn focused best practices from others on the same level as they are now.

As the venue is your biggest cost, it is also one of the scariest things to pay for in advance before you've started to accept retreat bookings. And that's why I recommend that you don't.
Open for sales first and then make the booking once you have a clearer sense of what the group size will be.

If you've read your audience, chosen the right topic, and warned them appropriately before you open sign ups, I recommend expecting that the people who sign up right out of the gate (in the first day or week depending on how you structure early-bird pricing) will represent 50% of you final numbers. Make your venue booking accordingly.

#2: Venue

If you're opting for something with a small group, you can rent a retreat house to accommodate that number (just make sure you are very clear upfront if there are shared bathrooms involved!). That makes it very easy to say that the event will be in a certain area where you have scoped out a number of vacation rental options, open registration and get cash in the event fund, and then plunk down money for the space.

If you don't feel up to the intimacy of having everyone in one house and managing the flow of the catering and meals, the price— for you— of running the event will jump considerably. You can expect:

  • Individual, en-suite attendee rooms in a retreat center to run at least $100/person/night in the venue's off-season
  • Catered meals and coffee breaks to run at least $120/person/night for an inexpensive establishment

If you want to go this route, I highly recommend looking for a space that is a dedicated retreat center rather than a traditional hotel. Retreat centers include many gathering spaces for groups to congregate in during “off” hours, tend to be considerably less expensive than hotels, use flows to keep groups separated from other groups for a “we’re the only folks here feeling,” and tend to be located in restorative, nature-rich areas.

These spaces are easy to Google and university campuses are a good place to find them– if you're interested in doing an event in the summer, they're also your best bet for price, as that's the low season for university events. Cvent, a website for meeting and event planners that lists every venue under the sun all over the world, has complete listings by destination as well.

Pro tip: Make sure to check if your clients have dietary restrictions or preferences and if the venue can accommodate their needs!

#3: Pricing

In terms of how you offer pricing for your retreats to attendees, it seems like you have choice of whether you should include the accommodation and meals in the price or have attendees cover it themselves, but I've seen much better results industry-wide when everything is included.

Events with uneven offerings in terms of what is bundled in the price tend to get the most “didn't meet my expectations”-style complaints about the on-site experience, and those then overshadow the content of the retreat itself.

Speaking of pricing, you also need to nail down how you sell the tickets to your retreat. And did you know you can use ConvertKit Commerce to sell tickets to your retreat? All you need to do is set up a product page with your event details and start selling! Check out this example:

Virtual retreat ConvertKit Commerce product page
This ConvertKit Commerce product page is set up to sell tickets to a virtual ukulele retreat. Image via Caroline Scruggs

#4. Extras

The thing that I've found with “extras” from activities to schwag– whether you are offering a weekend retreat (definitely an easier thing to sell) or a week-long– is that you'll end up being very surprised as the organizer, after weeks and weeks of working up the event, how quickly it gets over.

There's really no need to pack it with bells and whistles. That intangible retreat experience is really what you're selling and what will strike people.

#5: Protect yourself

Nobody's favorite topic but it has to be said: your clients should sign a contract for your in-person retreat that limits your liability and sets 100% clear expectations of what will be delivered in a legal document to avoid later claims. it should also address topics like IP, Force Majeure, etc (check this with your attorney). Get their signature when they sign up for your event to avoid an awkward situation at the actual event. Additionally, confirm with the venue if they include any liability insurances for their premises. if worst comes to the worst, a lawsuit can not only ruin your retreat but your entire business.

Does planning a retreat sound right for your audience?

Feel an idea for a retreat for your business stirring? How could you use a small-group retreat to take your business to the next level?

Virtual retreat ConvertKit Commerce product page
This ConvertKit Commerce product page is set up to sell tickets to a virtual ukulele retreat. Image via Caroline Scruggs

And did you know you can use ConvertKit Commerce to sell tickets to your retreat? All you need to do is set up a product page with your event details and start selling!

Start selling within minutes

As a creator, you deserve to get paid for your work. ConvertKit Commerce is ready-made to help you sell digital products.

Get paid with ConvertKit Commerce

Gabi Logan

Gabi Logan is a Certified Executive Coach, author, and co-owner of the Rosewood Writing Retreat Center, and Dream of Travel Writing, which helps freelance travel writers grow their incomes. Author of The Six-Figure Travel Writing Road Map, she coaches travel writers privately, at her writing retreat in the Catskill Mountains of New York, and in workshops around the world, and edits the Travel Magazine Database, which includes daily posts analyzing which sections of travel magazines are open to freelance writers and how to pitch them. Her work has appeared in national and international publications, including The Dallas Morning News, USA TODAY, and print anthologies.

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