When I started hosting monthly wine-themed events, I had no idea how much the experience would teach me about planning, connection, and community. Here are 12 lessons I’ve learned that I hope will inspire and guide you on your own journey:

1. The amount of time you think you need to plan one event per month is never enough.

Everything takes longer than expected! From brainstorming ideas to locking in venues and finalizing details – always give yourself more time than you think you need. In short, if you are going down the path of monthly events, recognize the reality that you’re either hosting an event, or planning the next one. 

2. Ensure you have people who support your vision and can help you.

Your dream team is essential. Whether it’s friends, family, or in my case, very committed group moderators, having reliable people in your corner makes ALL the difference.

3. Variety is the spice of life and the secret sauce for driving engagement.

Mix it up! Rotate themes, rotate venues, incorporate different types of wines and wine related activities. The goal is to have fun! Stay inventive and open to try new things. Everything you plan won’t cater to everyone, but over time if you offer enough variety, there will be something for everyone. 

4. Sometimes less is more.

Not every event has to be a massive production. Smaller, intimate gatherings can be just as impactful and often foster deeper connections. Plus, they often give you a much needed opportunity to catch your breath. Win-Win! 

5. Give the people what they want.

Ask for feedback after each event – and when you can, adjust to it. Listening to your attendees ensures future events hit the mark and keeps your community engaged. 

6. Be true to your vision.

This might seem counter to the above tip, and it isn’t. There is room for both things to be true. The reality is your authenticity will attract the right people. Sistah Sips has grown organically and consistently, with very little solicitation. What I’ll share because I’ve seen it over and over again in the last year. Stay grounded in your goals and mission, and trust that your audience will find you. Mine certainly has! 😀

7. Embrace the unexpected.

This should’ve probably been number 1, but alas, it’s tip 7. Repeat after me – Even the best-laid plans can go awry (and did!). Stay flexible and remember that sometimes the most memorable moments come from improvisation. My mantra has become: the events will go exactly the way they are supposed to go, and whoever needs to be there, will be. Believe that and then go about the business of having an amazing time. 

8. Celebrate the small wins.

This is a big one. Event planning is hard work, and sometimes when the outcome doesn’t match your vision it’s easy to get discouraged. It’s important in those moments to remember that every milestone, whether big or small, deserves recognition. These wins, even the small grateful wink from a departing attendee, fuel your motivation to keep going. And that’s all you’re required to do – keep going. 

9. Make it Instagram-worthy.

This is a gap for me and an area I need to get better in but don’t underestimate the power of your social media story. Create visual moments that people want to share. From table settings to signage to merch, those photo ops help spread the word and build your brand.

10. If you’re charging, the price is the price.

Don’t undervalue yourself. I obsessed about this and for the entire first year, and instead of charging when I should have, I covered costs for most events. Here’s the thing, there’s an important balance here because you do have to invest in your vision and bring it to life. But, when the occasion necessitates a fee, focus on delivering a premium experience that exceeds expectations, and your attendees will see the value.

11. Invest in yourself and your craft.

Take time to learn and grow. You aren’t on this journey alone, and there is so much power in finding other professionals or extreme hobbyists who share your passions and you can grow together. Attend other events, read books, or take a class in the area you’re trying to build expertise. Your effort to refine your skills will show in every event you host. As I think about how my knowledge and expertise has evolved from starting a group as a casual wine drinker, to now having my level 2 certification through the Wine & Spirit Education Trust (WSET), I couldn’t be more proud, and there are few other things that have been more worth it. 

12. When all is said and done, it’s all about sisterhood.

Finally, and this one for me remains my north star – The heart of every event lies in fostering connection, support, and joy within your community. Nothing matters more. Never lose sight of that.

Each of these lessons is rooted in my experience with Sistah Sips Society. This journey has been as much about personal growth as it has been about community-building. If you’re considering hosting your own events, I hope these insights will serve as a guide to creating something truly special.