I’d love to take a moment to chat about the kinds of issues retreat leaders don’t normally discuss.

First of all, in case y’all don’t know me – my business is Wanderlust Entrepreneur. I also have a full-service travel company that does retreat management and bespoke travel since 2003.

My love of retreats started back in 1998 when I went on my first retreat with don Miguel Ruiz (author of The Four Agreements). It was life-changing in every sense of the word and expertly executed. I had the privilege of being his biz manager from 2000 through 2002, managing all of his retreats.My travel company has planned and managed over 1000 retreats and I’ve trained over 15k retreat leaders through Wanderlust Entrepreneur – and in all this time I have seen all the good and bad you can possibly imagine.

One of the top issues for me is the number of uneducated people running retreats. So let’s get into it.

First and foremost – most retreats are packaged experiences that include room, board, activities, and transportation to those activities. Because of this, retreats fall under Seller of Travel law – especially in the 4 states in the USA that have strict law as well as in Canada in the 3 provinces that also have these laws. In Europe, there are similar laws present too. And by the way, Seller of Travel law has nothing to do with you booking airflights.

The reason for these laws is because you are responsible for the safety of your group, and the travel industry wants to make sure the public is protected.
For example, many retreat leaders are not incorporated, do not put those retreat funds into an escrow account (and spend those funds before their trip runs), aren’t registered businesses in their locality, and have no insurance, do not use legal forms (some use simple waivers which are not appropriate).

Why is all this important? Well, allow me to share some things that I have seen in those 1000+ retreats that my company has assisted or personally run. Since I was a physician – of course, the first category is particularly important to me.

Safety & Health Risks

• Medical Emergencies – Participants having allergic reactions, heart attacks, and severe injuries.
• Food Poisoning – Contaminated food leading to stomach illnesses.
• Dehydration or Heat Exhaustion – Particularly on retreats in hot climates.
• Wildlife Encounters – Snake bites, insect stings (anaphylactic shock), or animal attacks in nature-based retreats.
• Accidents & Injuries – Slips, falls, car accidents, or adventure activity mishaps.
• COVID-19 or Other Illnesses – An outbreak among participants leading to quarantine issues.
• Critical Harm – Rape, abduction, trip leaders or guides having sex with participants, death

Logistical Issues

• Venue Problems – Arriving at a venue and them telling you that you do not have a reservation, double-booking, poor facilities, unexpected construction, or the venue not meeting expectations.
• Weather Disruptions – Rain, hurricanes, snowstorms, or extreme heat affecting outdoor activities.
• Transportation Issues – Flight delays, lost luggage, canceled transfers, or unreliable local transport.
• Accommodation Nightmares – Poor hygiene, uncomfortable beds, overbooked rooms, or loud surroundings.
• Time Zone Confusion – Guests arriving at the wrong time due to miscommunications.
• Food & Dining Problems – Not enough food, bad quality meals, dietary restrictions not met, or food poisoning.
• Legal & Paperwork Issues – Incorrect visas, passport problems, seller of travel law violations, or lack of proper contracts.

Financial Problems

• Underpricing the Retreat – Leaving little to no profit margin, or worse, losing money.
• Last-Minute Cancellations – Participants backing out and demanding refunds.
• Not Meeting Minimum Numbers – Struggling to break even because too few people signed up.
• Payment Failures – Issues with processing transactions, bounced payments, or fraudulent chargebacks.
• Hidden Costs – Unexpected fees like local taxes, transportation surcharges, or venue add-ons.
• Insurance Problems – Lack of proper travel insurance leading to financial burdens in case of emergencies.

Group Dynamics & People Issues

• Difficult Participants – Attendees who complain, argue, or disrupt group harmony.
• Cliques & Exclusions – Groups forming within the retreat, leaving others feeling left out.
• Instructor Conflicts – Co-leaders or guest speakers disagreeing in front of participants.
• Unrealistic Expectations – Guests expecting a luxury experience when it’s a rustic retreat.
• Overwhelmed Introverts – Some guests struggling with constant social interaction.
• Cultural Sensitivities – Attendees unknowingly offending locals or each other.
  Language Barriers – Miscommunications due to different native languages.

Emotional & Spiritual Challenges

• Breakdowns & Emotional Releases – Participants experiencing deep trauma resurfacing unexpectedly.
• Resistance to Change – Some guests struggling with the transformation process and lashing out.
• Feeling Unfulfilled – Participants leaving feeling like they didn’t get the experience they expected.
• Leader Burnout – The host feeling emotionally or physically exhausted from holding space for others.

Marketing & Branding Issues

• Misleading Marketing – Participants feeling misled by exaggerated promises on the sales page.
  Bad Reviews – A negative experience leading to poor testimonials and reputation damage.
• Social Media Backlash – Public complaints or negative comments affecting future sales.
• Low Engagement – Retreat leaders struggling to get participants excited pre-retreat.

Spiritual & Ethical Risks

• Cultural Appropriation – Using sacred traditions improperly, offending locals or attendees.
• Unethical Practices – Overcharging, false advertising, or leaders with questionable ethics.
• Lack of Inclusion – Some participants feeling excluded based on background, beliefs, or needs.
• Spiritual Bypassing – Dismissing genuine emotional struggles with toxic positivity.

Post-Retreat Problems

• Re-Entry Shock – Attendees struggling to integrate back into their daily lives.
• Lack of Follow-Up – No post-retreat support, leaving attendees feeling abandoned.
• Refund Requests – Unhappy participants asking for money back after the retreat is over.
• Lost or Forgotten Belongings – Items left behind at the retreat venue.

Bottom line:

Get educated. Be prepared. I don’t care if you get educated by my company or another very experienced company. Just remember, you are holding beautiful lives in your hands and you are responsible for that. As retreat leaders we hold sacred space for magic to happen in – and THAT makes all of the above well worth it. I hope this is helpful for the community.

And if you could use some help optimizing your retreat business… I HIGHLY recommend joining me on our upcoming mastermind retreat sailing the coast of Croatia August 22-29th on our private luxury yacht.

If you’ve been feeling stuck in your business or you’re ready to take it to the next level, this trip is EXACTLY what you need.

You’ll have a full week of high-level brainstorming, personalized feedback, and meaningful conversations with heart-centered entrepreneurs who truly get it.

It’s totally all inclusive and you’ll leave Croatia not just refreshed, but ready to take actionable steps to grow your life and business to the next level.

To your wanderlust life and biz, Sheri & the whole Wanderlust Team! xox