Small group discussions during one of our very first Thoughtful Gay Man gatherings in Chicago.

Lessons Learned As A Meetup Organizer

This December will mark two years since I started my own Meetup group, called The Thoughtful Gay Man. It began with a simple question: Where do gay men go to talk about and work on living their best lives? As I looked around Chicago (and thought about previous cities I’d lived), there wasn’t such a place. With a little bit of faith and a whole lot of uncertainty, I took the leap and am so grateful I took that step.

Over the last two years, I’ve learned a lot as a Meetup organizer. If you’re interested in starting a group in your own city, here are some lessons I’ve learned along the way:

  1. The fear of “will they come?” is okay to think. Entertaining and hosting is one of my favorite things to do. Deep down, there’s always this little bit of nervousness before guests arrive. My mind races, wondering whether people will show up or not. My imagination scurries, stirring up anxiety; a taunting whisper says, “All of this preparation was for nothing. No one really wants to come.” If this is your first event, it’s very likely you’ll feel at least a little bit of this nervousness. And that’s okay! My first event for The Thoughtful Gay Man happened to take place on a blizzard-filled night. In Chicago. In January. If you’ve ever lived through an upper Midwest winter, it can get ugly. Despite the weather conditions, over thirty guys showed up to see what the group was all about. Which leads me to the second lesson.
  2. Numbers don’t mean everything. It’s true. Even though this goes against everything American culture stands for: bigger is better and more is meaningful. I’ve hosted gatherings, like the kick-off event, where over thirty attended. At one of our recent book club Meetups, just three showed up, but the discussion was so rich and enlightening. I was grateful for every word and insight each guy contributed during our time together. Remember that the people who show up are the exact people who need to be there. No more, no less. Try not to make the number of people who showed up your primary measurement of success or failure.
  3. You can’t please everyone. There will be critics and naysayers who attend your events. For me, they’ve been few and far between, but it’s always those critical voices that tend to stick in our mind. After a second look, these “critics” might just be providing honest, helpful feedback. Maybe they saw something I overlooked. Be open to that. None of my events are run perfectly. I’ve done my best to keep my ears open to feedback and honestly reflect on both what worked and what could have been a little more effective. Most people aren’t trying to poke holes in your group. Allow feedback to be your friend.
  4. Keep at it. There were months when I stood toe-to-toe with many self doubts about the content I wanted to present, the relevance of my group, where I wanted to take the guys who attended. Some of my doubts were: Why would anyone want to hear from me? Who am I to talk about or facilitate this or that topic? The more you try to reach out and create something new in the world, the more that gremlin in your head will throw a tantrum. The best strategy is to write a short paragraph for your event, throw up a title, and notify your members, right away. You can always play with the wording and shift things around later. Pick the date, time, and location and allow the rest to come together. I love this quote by Tim O’Shaughnessy: “More is lost in indecision than in the wrong decision”.
  5. Ask for help. I honestly still struggle with this one. As you host events on a regular basis, there will be familiar faces showing up again and again. These are your core people — your biggest fans and advocates. As soon as you find these dedicated members, have a chat with them about their talents, skills, what they enjoy about the group, and have some ideas of how they might be able to help run the group. This simple conversation creates a space for members to invest more in the group and for you to not carry the entire Meetup on your shoulders. As your Meetup grows, this will also prevent you from burnout. If you have controlling tendencies (like I do at times), just breathe into it and trust others. It’s worth it.
  6. Community isn’t (always) glamorous. There are definitely moments when I wax poetically about the lovely nature of community. Here, I’m specifically talking about the act of creating a place for people to come together. Of creating community. Yes, these gatherings can lead to warm and fuzzy feelings, but when people collide, from all types of backgrounds, bringing their own baggage and points of view, you never know what you’re going to get. And that’s okay. Simply be present with the people who show up. A gracious and open attitude goes a long way when you’re an organizer. Give people the benefit of the doubt and be sure to let people know how great it is to meet or see them. By the way, community is awesome!
  7. Address the flake factor early. I took this advice from a dear and trusted friend (and Meetup organizer) early on: charge something for events, even if it’s five bucks. I know, it’s a little scary to charge anything. I was scared! I would wring my hands over a measly five dollars, fearing people would question why the events aren’t free. Here’s the thing: free events, in my experience, prevent people from committing and investing in actually showing up. Even a small fee does the trick. Use the money to provide simple refreshments, pay for your monthly Meetup fee, or use it toward rental space. Overcoming this fear is totally worth it in the end.
  8. Belonging heals all wounds. Okay, maybe not all wounds, but knowing and feeling that we have a place to belong is a healing tonic in a world full of disconnection. One of the greatest joys as an organizer is creating a space where people can show up and know they have a seat at the table. They have a voice. They matter. Just as they are. Whether you’re hosting a book club, a civic-oriented Meetup, an outdoors-y gathering, or whatever Meetup you choose to create, communicate to your members how much they belong. It is such a transforming gift.
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