Dear Shannon – Will They Support My Retreats?

Hi, my loves! This week, we’re doing one of my favorite posts, a Dear Shannon! I recently got a message on my Instagram from an aspiring retreat planner. Her message excited me because after reading my book, The Retreat Leader’s Playbook, she’s decided to transition her hobby to a full-fledged retreat business! Let’s hear what she has to say. 

Dear Shannon,

Your new book has inspired me to venture into the business of retreat planning! I’m the designated event planner for my office, and I’ve unofficially helped out with a few destination weddings for close family and friends. I totally feel like I have what it takes to turn this into a successful business. I mean, I’ve been doing it for free with great feedback, and to get an additional income stream would make a significant difference for me and my family. How can I transition what I’ve been doing for free to my family and friends without any awkwardness? I’ve been doing it as a hobby for so long that I’m super nervous about how they’ll react to the new change. I’ve dreamed about this for so long that I’ve secretly had my logo designed and checked to see if my dream business name is available (it is!). I’d love it if you could share a few tips about transitioning from hobby to business. Thanks!

Ashley B.

Dear Aspiring Retreat Planner,

First off, congratulations on taking the first steps toward turning your passion into a business! It’s a brave and exciting move, and the fact that you’ve been doing it as a hobby with great feedback is a wonderful foundation. Transitioning from hobby to business can be a delicate process, especially when it involves changing the dynamics with family and friends. Below are a few tips to help you make the shift as smooth and professional as possible. 

What is your why?

Before you convince anyone else to hire you, or share with others why you do what you do- YOU should know. What is the reasoning behind doing this?  If it is just money, then don’t continue reading as that isn’t a good enough reason.  Don’t get me wrong, abundant financial growth is BEAUTIFUL- but it should never be the primary factor or you will get discouraged as you build.  If you struggle with money as a whole (either asking for it, or feeling worth it or motivated by ONLY money) you have got some work to do around the relationship with money. I harp on this as it can be your biggest obstacle as you grow, or your biggest cheerleader. 

Define Your Retreat Business

Before you approach anyone, it’s crucial to have a clear understanding of your business. This means defining your services, pricing structure, target market, and what sets you apart from other retreat leaders. Having a well-thought-out business plan not only boosts your confidence but also demonstrates your professionalism to others.

Communicate Transparently

When you’re ready to start charging for your services, have honest and transparent conversations with your family and friends. Tell them about your aspirations, your steps (like designing a logo and securing a business name), and why this transition is important to you and your family’s future.

Set Boundaries

It’s essential to establish boundaries early on. Let your family and friends know that while you value their support, your services now come at a cost. You can initially consider offering a “friends and family” discount, but make it clear that your time, expertise, and resources have value.

Professionalize Your Approach to Your Retreat Business

Invest in professional tools and systems. Create a website, have business cards printed, and use contracts for your services. These actions reinforce your professionalism and subtly communicate that you are running a business, not a hobby.  Also, consider taking a course to really hone your skills (hint hint). 

Seeking Continuous Education

Show your commitment to your new venture by investing in your education. Attend workshops, take certification courses, podcasts, and read industry books (like you’ve done with mine!). This improves your skills and demonstrates to your family and friends that you are serious about your business.

Leverage Testimonials

Use the positive feedback you’ve received from your unpaid work to build credibility. Ask those you’ve helped to provide testimonials that you can use on your website and marketing materials (videos wold be best, but written can work too). This social proof can be very powerful in attracting new clients.

Celebrate and Share Your Successes

As you start to achieve success, share it with your family and friends (and the world). Let them see the fruits of your labor and how their support has helped you. This not only validates your transition but also helps them to feel part of your journey.

Network and Market Yourself

Now that you’re in business, it’s time to expand your network beyond family and friends. Attend networking events, join professional groups, and use social media to market your services to a broader audience.

Offer Value-Added Services

Consider adding extra value to help differentiate your paid services from what you’ve done for free. This could be anything from providing personalized welcome gifts to attendees, exclusive access to unique retreat locations, or additional planning services that you didn’t offer before.

Be Patient and Persistent

Remember that change takes time. Some family and friends may need time to adjust to the idea of paying for your services. Be patient but persistent in reinforcing your new business boundaries.

Transitioning from hobby to business is a journey filled with learning and growth. While there may be some initial awkwardness, your true supporters will respect your decision and may even become your biggest advocates. Remember, the value you provide is worth paying for, and you deserve to be compensated for your time, creativity, and expertise. Good luck!