Why Most Coaches Fail at Hosting Retreats—And How to Avoid It

Retreat Planning Tips

Shannon Jamail

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Shannon Jamail

She is a best-selling author, podcast host, retreat leader, therapist turned mentor, Yoga Teacher trainer, and tequila connoisseur (not really, but she does enjoy sipping on a good pour).

Let’s have a real talk, coach to coach.

I’ve seen it happen time and time again—brilliant, heart-led coaches with thriving one-on-one practices or online programs decide to host a retreat. They dream of connection, transformation, and that magical retreat “glow” moment. But then? It flops. They lose money, feel overwhelmed, or walk away thinking, “Never again.”

And honestly? It breaks my heart.

Because retreats can be one of the most fulfilling (and profitable) parts of your business—if you know how to do them right.

So today, let’s dive into why most coaches fail at hosting retreats—and how you can avoid those mistakes with a smarter approach to retreat planning for coaches.

Mistake #1: Going in Without a Clear Intention or Strategy

Hosting a retreat isn’t just a fancy vacation with yoga and a smoothie bar. It’s a business decision. Too many coaches plan their retreat like a passion project instead of a strategic offer that fits into their overall business model.

⏩️  How to Avoid It:

Start your retreat planning by asking:

  • What transformation am I guiding my attendees through?
  • How does this retreat support my other offers or programs?
  • What does success look like—both emotionally and financially?

If your answers are fuzzy, pause. Clarity is your foundation for a retreat that works and sells.

Mistake #2: Underestimating the Logistics

Here’s the truth: retreat planning for coaches involves way more than just showing up and teaching. It’s transportation, food allergies, contracts, room assignments, waivers, activities, downtime, venue logistics, budgeting… oh, and you still have to coach.

⏩️  How to Avoid It:

  • Work with a retreat planner (yes, they exist and yes, they’re worth every penny).
  • If you’re DIY-ing, use a proven planning system. (Hint: my Retreat Leader Membership includes all the tools.)
  • Give yourself at least 6–9 months to plan your first retreat well.

Mistake #3: Pricing Based on Emotion, Not Math

This is where so many coaches lose money. They underprice their retreat to “make it accessible,” but end up cutting corners or absorbing costs. Your passion doesn’t pay the venue.

⏩️  How to Avoid It:

  • Build a real budget—including every cost, from snacks to swag bags.
  • Include your time and profit margin in your pricing (this should be the FIRST line item in your budget).
  • Price based on the transformation you offer, not what you would pay.

Mistake #4: Trying to Do It All Alone

You don’t have to be the retreat leader, travel agent, marketer, and therapist all at once. When you try to do everything, something will drop—and usually, it’s your sanity.

⏩️  How to Avoid It:

  • Hire help (even part-time).
  • Use automation tools for registrations.
  • Get guidance from someone who’s hosted retreats successfully (hi, that’s me!).
  • Stay in your zone of genius: creating transformation and holding space—not dealing with lost room keys.

Mistake #5: Skipping the Marketing Plan

If you post once and hope it fills—spoiler alert—it won’t. The truth is, retreat planning for coaches is only half the job. The other half? Filling the retreat with aligned, excited guests.

⏩️ How to Avoid It:

  • Start promoting early and consistently (minimum 4–6 months out).
  • Along with emailing your current database and reaching out to your existing peeps, use a mix of blogs, emails, social media, and podcast episodes.
  • Speak to the transformation in your messaging, not just the venue or itinerary.

Final Thought: Retreats Are Sacred… and Smart

Hosting retreats is about creating space for deep transformation—for your guests and for yourself. But if you treat it like a hobby instead of the powerful business tool it is, you’ll burn out fast.

The good news? You don’t have to go it alone.

Inside my Retreat Leader Membership, you’ll get:

  • Proven strategies for retreat planning
  • Budget templates and checklists
  • Marketing tools that work
  • And support from someone who gets it

You’ve got the heart. I’ve got the roadmap.
Let’s build retreats that work—for your guests and for your business.

Want More Support?

🎙️ Tune into The Retreat Leader Podcast every week for actionable tips on retreat planning for coaches
📩 Or join the Retreat Leader Membership and make your next retreat your most profitable yet.

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