Failure Is More Common Than Success—And That’s a Good Thing

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).

So the other night I was watching football with my husband.

Now listen, football isn’t usually my jam—I’m more of a “Champagne and retreat planning” kind of girl—but I do love a good behind-the-scenes story. So we were watching this show about NFL quarterbacks, and Kirk Cousins (quarterback for the Falcons) said something that stopped me in my tracks:

“Failure is so much more common than success.”

Boom. Truth bomb.

And I haven’t been able to stop thinking about it—because y’all, this isn’t just true in sports. It’s true in business. Especially when it comes to hosting profitable retreats.

Let’s Normalize the F Word (Failure)

Here’s the thing: most people don’t talk about failure.
Social media is filled with the highlight reels—sold-out retreats, dreamy destinations, testimonials on testimonials (ME ME, I do this too!).

But what you don’t see?
The flopped launches.
The zero-signup events.
The late-night panic googling “how to fill my retreat.”

And yet… those are the moments where we learn the most.

I’ve been in this game for over a decade. I’ve hosted retreats all over the world, supported hundreds of other retreat leaders, opened a 46 acre retreat center and built a business I love. But it didn’t happen without setbacks.

I’ve underpriced, overbooked, not sold out (yep, it happens)—and every one of those moments made me better.

The only way to not fail is to not try. And that’s not how we grow.

Failure Is a Feature, Not a Flaw

Let’s go back to our guy Kirk Cousins.
He wasn’t talking about failure like it was a problem—he was talking about it as a path.

You fail, you analyze, you adjust.
You come back stronger.

And that’s exactly what successful retreat leaders do.

They launch even when it’s scary.
They try a new pricing model, even if they are worried.
They send the emails, post the content, host the Zoom Q&As—even when they feel like no one’s watching.

They take notes. They tweak. They grow.

Hosting Profitable Retreats Isn’t About Perfection

Let me say this clearly:
Hosting profitable retreats is not about getting it perfect on the first try.

It’s about being committed enough to keep going—even when it doesn’t work the way you thought it would.

Here are a few failures I’ve seen turn into 6-figure success stories:

  • A yoga teacher launched her first retreat and sold two spots. TWO. She almost quit. But instead, she got support, fixed her messaging, and now runs a sold-out international retreat twice a year (that makes her 6 figures on two retreats!).
  • A mindset coach created a retreat that flopped. Turns out, her price point was actually too low. Once she reworked her offer and owned her value? Boom. High-ticket and high-impact.
  • One of my members emailed her list over and over with no replies. We added a sales strategy, she followed up with personal DMs, and filled the retreat in 10 days.

It’s not magic—it’s momentum.

So What Should You Do If You’re Facing Failure?

  • Stop Making It Mean Something About You
    Failure is data. That’s it. It’s not a reflection of your worth—it’s just a signal that something needs to shift.
  • Analyze and Adjust
    Where did things stall? Was your messaging clear? Did you have a marketing and sales strategy? Did you price for profit or panic?
  • Get in the Right Room
    Join spaces where other retreat leaders are doing the dang thing (like my Retreat Leader Membership!). Community shortens the learning curve and normalizes failure as part of the process.
  • Take the Next Step Anyway
    Post the post. Send the email. Reach out to that past client. Hosting profitable retreats requires consistent action—not just perfect plans.

Final Thoughts

If you’re in the messy middle of building your retreat business and wondering, “Why isn’t this working yet?”
Let me remind you:

You’re not behind. You’re not broken.
You’re just on the path.

Failure is more common than success—and that’s a good thing.
Because every failed launch, low signup, or awkward pitch is shaping you into the leader who CAN fill a retreat, change lives, and build a business that actually works.

So keep going.
Keep learning.
And keep betting on yourself.

Love,
Shannon

PS: Want to learn how to fail faster (and smarter) on your way to a profitable retreat biz?

Join me in London on October 10th for Vision to Venue, a one-day workshop for coaches, creatives, and retreat leaders who are ready to build sustainable, profitable retreat businesses—with real strategies, real support, and real results.

☞ Save your seat here

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