Answer extracted from The Retreat Leaders Podcast — listen to the full episode below.
How to Avoid Costly Mistakes Before Your First Retreat Launch?
Shari Leid proactively sought expert guidance from a retreat strategist before launching her first retreat, prioritizing learning from experienced practitioners over figuring everything out alone. Her philosophy is simple: start ugly and make it pretty as you go along—a mindset that values mentorship and real-world feedback over reinventing the wheel.
Rather than relying on ego or self-taught improvisation, Leid reached out to Shannon Jamail, a retreat strategist with over 100 retreats hosted, for one-on-one coaching. This deliberate choice to ask "who can I learn from?" before launching set her apart from many entrepreneurs who assume they can navigate unfamiliar territory alone.
The power of this approach lies in its humility. Seeking expert guidance early meant Leid could avoid the trial-and-error trap that costs money, time, and credibility. By working with someone who had already made mistakes so she wouldn't have to, she positioned herself to launch with greater confidence and fewer preventable missteps.
This mindset—combining competence in one domain (law, writing, speaking) with openness to learning in a new one (retreat business)—is what allows high-achievers to scale successfully across different ventures. As Shannon Jamail notes in the episode, this kind of vulnerability and willingness to learn from others is rarer than it should be, especially among driven entrepreneurs.
"That is how I found you—by asking who I can learn from, because there are other people who have done this."
Shari Leid — Attorney, Author, Speaker, and Retreat Leader. Leid is an accomplished multi-domain entrepreneur who has published four books with a fifth due in February. Her career spans writing, media contributions, speaking engagements, and now retreat leadership. In 2023, she traveled across all 50 U.S. states, sharing a meal with a female stranger in every state—an experience that inspired her FLIP framework and her mission to deepen human connection and belonging.
If you want to understand how Leid applies this coaching to the specific structure of her women-only retreats—from pricing to participant selection to the unique connection methods she employs—the full episode offers deeper tactical insights on building a retreat business from the ground up.
See also
What is the format and target audience of Shari Leid's retreats?
Shari runs women-only, three-day retreats capped at a maximum of 10 women, held twice per year. The retreats are designed for women ready to build a deeper connection with themselves and others.
What is Shari Leid's FLIP framework and how did it originate?
FLIP stands for a four-step formula designed to help people connect with anyone in under 60 seconds. It originated in 2023 when Shari traveled across the United States and shared a meal with a female stranger in every state.
Why did Shari Leid decide to add retreats to her speaking business?
Shari Leid explained that the speaking business can be unpredictable, with fluctuating lean and flush months, and she wanted more steadiness as a solo entrepreneur.
Key takeaways
- Before launching your first retreat, seek out an experienced mentor or coach in that domain rather than relying on self-education alone.
- Adopt a "start ugly and make it pretty" philosophy that values iteration and learning over perfection from day one.
- High-achievers in one field can still benefit enormously from guided expertise when entering a new business area—humility is a competitive advantage.
- Proactive coaching relationships prevent costly mistakes that would otherwise require painful trial and error.