In my last newsletter, I shared something many retreat leaders quietly feel but rarely say out loud: You don’t need social media to fill a retreat.

And wow, the response was overwhelming (I was actually a little shocked!)

What I heard again and again was:
“This makes so much sense… but I still don’t know how I would actually do this.”

So let’s take a few minutes to make this real.

Filling a retreat the old-school way isn’t about clever marketing or having fancy words. It’s about clarity, conversation, and connection – done in a way that feels natural to YOU.

First, let’s redefine “old-school.”
Old-school does not mean outdated.😁
It means relationship-based, intentional, and personable.

This works especially well for retreats because:

• Retreats are high-trust experiences
• People want to feel safe before committing
• A personal invitation often matters more than a polished retreat trip page

This approach doesn’t rely on pressure or volume. It relies on presence.

Step 1: Start With a Clear Inner Circle

Before you promote anything, ask yourself:
Who already knows me, trusts me, and would love to go deeper with me?

This might include:

• Past clients or students
• People who’ve attended your workshops or talks
• Coaching clients
• People who’ve said, “One day I’d love to do something like that…”

Most retreats fill from a much smaller group than people expect.

Step 2: Think About Conversations, Not Conversions

Here’s a huge mindset shift:

• Your goal is NOT to necessarily to register someone right then and there.
• Your goal is to start a conversation.
• That alone takes away a ton of pressure.

What This Looks Like in Real Life…

Retreat: Renew & Restore – A 7-Day Wellness Retreat in Costa Rica
Personal Email:
Hi Sarah,
I saw your last post on FB about your grandchild – congrats! I’m so happy for you. 
Listen, I’m planning a small wellness retreat in Costa Rica this November focused on rest and renewal, and you came to mind while I was working on it. I remember you saying how stressful last year was – this would be the perfect getaway.
I’d love to share the details (and the magic) of the retreat with you – let me know if you have time this week for a catch-up on Zoom.
Warmly,
Amanda

Notice what’s happening here: You took 5 minutes to see what Sarah’s been posting on her socials and used that to start the conversation.

Step 3: Personal Outreach That Doesn’t Feel Awkward

Personal outreach feels uncomfortable when you think you’re bothering someone.

It feels natural when you remember:

• You’re offering something meaningful and life-changing
• People are free to say no, it’s not a personal affront! Stop taking the word no personally.

What This Looks Like in Real Life…

Retreat: Composing From the Soul – A Creative Writing Retreat in Scotland
Voice Note (Transcribed):
“Hi Jen, it’s Lisa. I just wanted to leave a quick message because I’m putting together an absolutely delicious writing retreat near mystical Rosslyn Chapel next spring, and you popped into my head right away.
It’s designed for people who want quiet, inspiration, and time to go deep – very much in line with the work you’ve been doing.
If you’re curious, I’d love to share the magic with you and share the deets. Lemme know what your schedule looks like this week. Can’t wait to catch up!”

Step 4: Expect to Follow Up (It’s Normal!)

Very few people say yes right away – however, that doesn’t mean they aren’t interested!!!

Old-school marketing assumes:

• People need time
• People have questions
• People want to feel into timing
• Following up is part of being present, not pushy.

A Gentle Follow-Up Example…

“Hi Jen, I just wanted to circle back in case my last message got buried. I simply wanted to check-in and see if you had any time to do a quick Zoom chat about the writing retreat to Ireland – and of course, answer any questions you might have. It would be fabulous to catch up too! Let me know what this week looks like for you.“

Most people will be happy you followed up – we’re all busy these days.

Step 5: Speak Where Your Peeps Gather

One of the most effective old-school strategies is speaking in real-world spaces. This is actually how I grew my email list and filled ALL my programs and retreats back when I used to teach “The Four Agreements.” Truth.💯

• An independent bookstore
• A library or community center
• A wellness space or yoga studio
• You don’t need a big crowd – you need the right one.

What This Looks Like in Real Life…

Retreat: Sacred Pause – A Women’s Retreat in Sedona, Arizona
Follow-Up Email After a Bookstore Talk:
Hi Maria,
It was so lovely meeting you at the bookstore talk last week – I really enjoyed our conversation afterward.
As promised, I’m sending the details for the Sedona retreat I mentioned. Do take a look and let me know if you have a few minutes this week to connect on Zoom so I can share more about this magical retreat and answer any questions you might have.
Warmly,
Rachel

This is simply continuing a conversation that your already started in person.

Step 6: Host Small, Low-Pressure Info Spaces

Instead of “launching” a retreat, create spaces where people can explore it.

This might be:

• A casual Zoom Q&A or Ask-Me-Anything session
• A small in-person gathering
• A short experiential session tied to the retreat theme

What This Looks Like in Real Life…

Retreat: Entrepreneurial Reset – A Business & Life Mastermind in Croatia
Email Invite:
Hi firstname,
I’ve had a few questions come in about the Croatia retreat this week, so I’m hosting a small, informal Zoom gathering next Tuesday for anyone who wants to learn more or feel into whether it’s a fit.
There’s absolutely no expectation to sign up – this is simply an “Ask-Me-Anything” space to connect, explore, and get some coaching. So bring your cuppa Joe or wine, ask me questions, and let me know how I can help!
Big hugs, Rachael

This takes away pressure and builds trust. Many of our students have not only signed folks up for their retreats from this strategy, but also got coaching clients and other business just from showing up with an open heart.

Step 7: Understand The Numbers

Here’s something most retreat leaders don’t realize:
You don’t need hundreds of people.

A 12-person retreat might require 20–30 real conversations
A 20-person retreat might require 35–45 conversations
That’s it.

When people see the math, the overwhelm normally disappears.

Step 8: Use Word of Mouth

Word of mouth works best when you actually ASK for what you want!!!

What This Looks Like in Real Life…

Retreat: Return to Stillness – A Desert Retreat in New Mexico
Simple Referral Ask:
Hi Laura,
I wanted to let you know about a quiet desert women’s retreat I’m offering this fall October 7-14th, focused on getting clarity and direction. It’s specifically for gals going through big changes in their lives, and if anyone comes to mind who might really benefit from this experience, I’d be grateful for an introduction. I can’t tell you how much I appreciate you sharing about this unique retreat – it means everything to me!
Big hugs, Rachel

This kind message opens doors without forcing anything.

Sheri’s Bottom Line

Old-school retreat promotion works best when:

• Your retreat trip page is clearly designed with strong pain points and benefits
• Your pricing makes sense
• You believe in what you’re offering

Keep in mind that: If marketing still feels uncomfortable to you, that tells me that you still don’t believe in your heart that selling is service. You cannot help people if you don’t put yourself out there.

Seriously, you don’t need to sound polished.
You just need to sound like yourself.

And when you do, the right people will recognize your authenticity right away. ♥️

xo Sheri
PS: Lemme know if this was helpful to you!