Start Hosting Events People Actually Love

This webinar’s the antidote to the awkward networking mixer. We’re sharing the exact proven strategies and tactics used to turn quiet rooms into vibrant, connected communities that attendees talk about for months.

Marketing Webinars
Co-Founder, My Creative Break

Kimberley Chan

Kim is the co-founder of My Creative Break and has a background in journalism and tech marketing. Her entrepreneurial journey started when she left her marketing job to travel and teach English abroad. During her journey, got to know many inspiring people, learned countless new skills and did things she never thought she would do—this taught her the importance of community and connecting with people. These experiences led her to co-found My Creative Break and curate in-person events. She also runs a travel community.

Third Wunder - With Wunder Webinar - Kimberley Chan - Speaker - My Creative Break - Co-Founder
Co-Founder, My Creative Break

Linda Cajuste

Linda is the co-founder of My Creative Break and a certified confidence coach who helps people connect through creativity and interactive experiences. After taking a sabbatical year to reconnect with her creativity going from introverted accountant to performing on stage and producing her first short film, Linda discovered the power of improv to build confidence and connection. Today, she helps entrepreneurs, founders, and community builders design events that spark authentic conversations and lasting relationships.

Third Wunder - With Wunder Webinar - Linda Cajuste - Guest Speaker - My Creative Break

Webinar Transcript

Mohamed Hamad: Hello, hello, hello everybody. Welcome back to another session. How’s everybody doing today? We’re very excited today to be talking about events, events in real life not a virtual one like the one we have today. I’m very excited to have with me here, Kim and Linda from My Creative Break, the dynamic duo and co-founders of an event hosting and team building company.

Just a little bit of a background. Kim is the co-founder of My Creative Break and she’s got a background in marketing. And Linda is a confidence coach who both got together and decided that they wanted to create their own type of events. They bring in confidence coaching, team building exercises, a little bit of improv into what they do. Welcome, Kim and Linda.

Kimberly Chan: Thank you, thank you for having us.

Linda Cajuste: We’re excited.

Mohamed: If you could give us a little bit of a background — I mean I already gave a little bit of a background — but what brought the idea of My Creative Break to life?

Linda: Yes. Definitely, let me start — long story short. My background, like I said, is confidence coaching. But just to say, I’ve always been a very shy and introverted person with big aspirations and big dreams — wanting to go on Broadway, doing all these things.

But one day I was just like, okay, if I want to act on these dreams, I need to start taking some steps and first off, dabble into improv. Which, by the way, that’s where I met Kim — during an improv class. So we met during improv.

Improv has a big influence on us meeting, and on everything we do. I got a bit more confident when I was doing improv. And one of the things it led me to — because my background is in accounting — was to take a sabbatical leave. I was able to take that and put the accountant aside and work on my creativity and things that I really wanted to do. So I flew to Paris for a year and I decided that this would be the year I would take a break to do creative stuff.

So kind of like when it started — a little bit like My Creative Break. I got to do a lot of things there. Did some improv overseas, tried stand-up, wrote my first short film — all kinds of stuff, really, to get out of my comfort zone and work on things I really wanted to do.

And then I had to come back to my job. Which was great, very grateful about that. But I was like, okay, how do I continue to do that while I’m working? How do I take that break and work on the creative side I started to develop? I met with Kim, and I’ll let her kind of end the story.

Kim: Yeah, actually — Linda came back from Paris and I almost didn’t recognize her. She was much more confident, much happier. She had grown a lot from the time she left and gone to Paris. That kind of inspired me a little bit because at the time I was working in marketing and I was feeling a little bit blocked.

I wasn’t learning anything new, I wasn’t growing. And just like Linda, I’m a creative person. I enjoy trying different things and learning new things, and I wasn’t getting any of that. So she kind of inspired me to go on my own sabbatical.

I ended up leaving my marketing job to move to Spain. I taught English there for a couple of months, and the people I met there inspired me to keep going. So after that I started traveling some more. I traveled Europe, ended up in Africa for a little bit — in Morocco — where I accidentally came across this travel community of people from all over the world who inspired me even more to keep going. And then I ended up in Asia.

Long story short, I came back to Canada. Linda and I met up and we were talking about our experiences. We were also talking about how people were telling us they saw how much we changed, how much we were growing, and they were asking us — what happened? What did you guys do? What’s causing this?

At the time, we didn’t really know. We were kind of just going with the flow and not really noticing the impact it was having on us. So in the end, we sat down and we were like, what is causing this? And it came to three things.

You’ve got to push yourself. You’ve got to do the things you really want to do and just try it, even though it scares you. You’ve got to surround yourself with people who are going to teach you things and motivate you — be around people who you normally wouldn’t be around. And then you just have to take the steps to get out of your comfort zone.

So we started encouraging people to do that. We started an online community, just saying: do things you like to do, take the steps to try something new. That was kind of like the base of My Creative Break. That was during the pandemic. We noticed that people wanted to connect because they were writing to us. So we started this online community, we would get people together online, and from there we grew to having people in person.


Mohamed: So you took your world experiences and distilled them down into your creative events. Now you started this in the pandemic — how have things changed since then? People’s expectations of events before and after the pandemic have completely changed. What is your experience with that, especially for creating events that are engaging?

Linda: Absolutely. During the pandemic there was a need for connection because we were all isolated, but we couldn’t do it live. So it was a lot of workshops online, trying to engage people but from afar. We really had to put together different workshops and a different way of interacting with people so they would still feel connected through the screen.

Then once the world opened up, we started doing live events — one of the first ones actually in Montreal where we met you. Because it was live events and people were craving that. Right after the pandemic, people were just like, okay, let’s go out there. We could feel the anticipation of just connecting with one another in person.

And then now we’re post-pandemic — what, four or five, almost six years? It’s changed again. People are still getting out there, but with a little bit more intention around interaction. Let’s go deeper. Connecting on a deeper level and learning. Not just, okay, let’s throw people together in a room. People are craving topics, things in common, getting to know each other beyond just: who are you and what do you do?

Mohamed: Yeah, there’s always the tried and true format of networking — a speaker comes up on stage, everybody breaks away into groups and they spend the entire night with the same people they met. How do you break that mold and get people moving around, chatting to each other, engaging in different ways?

Kim: We really try to make people as comfortable as possible because we know it’s not easy to be in a room full of strangers, especially if you’re shy or introverted. We actually try to get a sense of who is coming. And from the moment they walk in, we make them feel welcome. We say that our events are not just events — they’re experiences. From the moment you walk in, we’re going to accommodate you and make sure we take you through a journey so that by the end you feel like you got something out of it.

Linda: And I’ll add to that — even before you step into the event, we already make sure we know who’s going to be there. We try to find out as much information as possible, get a sense of who’s going to be in the room, and figure out how we can connect with them so they feel welcome and at ease before they even arrive.

So once they come to the event, those little welcoming touches throughout the event — making sure people interact with each other so it doesn’t feel awkward. We try to make it as easy and interactive as possible, and at the end, try to connect people together so the connection keeps flowing afterwards. We really take them on a journey and think about all of that when we create events.


Mohamed: So what’s your process for designing an event? I’ve been to your website — you create themes for different groups of people with different intentions behind each event. Sometimes team building, marketing events, women’s events. How do you design the experience and what techniques do you use to get people to engage knowing there are different audiences each time?

Linda: You’ve got to know your audience first. We always have an idea of how we want an event to be, but you’ve got to listen. Who is your audience? And really make sure it’s not about what you want or your needs — it’s about what their needs are.

We have different thematics and different groups that we serve. We have our women’s group — we had an event just last night. We have them in mind, and as we do events, we listen to feedback because they are the ones going through the experience. Listening to feedback is really crucial to how we continue to make sure they have the best experience possible. Sometimes we think of ways to connect people and they come back and say, we want more time to connect in groups. So we go with what the audience wants and needs. You have to be flexible — okay, I have this experience in mind, but once people have gone through it, what is it that they actually want and need? That will dictate how we offer the best event possible.

Kim: And I’ll add that when people sign up for our events, we’re already asking them: what is your goal? Why are you coming? What do you do? So we have a clear idea not just of who is coming, but what they want.


Mohamed: If someone is trying to set up their first event — and more and more events are happening now, people are craving connection after the isolation of the pandemic — the old style of just throwing up a place with a free drink or a keynote speaker is kind of going by the wayside. People are expecting more. I’m hearing things like coffee raves and different ways of engagement. What advice would you give to someone doing this for the first time?

Linda: One of the first things to think about is: how would you want to feel at an event yourself? Start there. And then focus on your audience. When we started, we made sure we created spaces that we wanted to see. We’ve been to events where there was no host, nobody welcoming you. For me, being shy, it felt like I went into a room, stayed in a corner, nodded and smiled, and couldn’t really connect with people. That helped dictate creating a space you’d actually want to be part of.

Think about what would be engaging. Think about the audience you’re attracting. If you’re just starting to create an event — what do they want? What is your goal? What do you want people to feel, from the moment they sign up all the way to the end? Go through each step. I would say that’s the basis.

Kim: People really want to feel like the event was created with them in mind. So put yourself in their shoes, ask the people what they want — which is what we do. You have to remember that you’re not just designing an event where you’re putting people in a room. You really want them to feel seen. We’ve gone to events and just felt like a number in the room, like no one was really catering to us. That’s what we try to keep in mind.


Mohamed: What’s your perspective on having really big events versus smaller, more intimate events? Obviously with your thematics you can’t really have a huge number of people for each one — how does that work out for you?

Linda: Different goals. It’s okay to have bigger events, but there’s a different intention in mind. If you really want an intimate experience where people connect on a deeper level — not just surface level — smaller, intimate gatherings let you achieve more of a sense of community. People get more of you as a host, more of the experience. They feel like they’re at the center of it.

With larger events, it’s not to say that deep connection isn’t achievable, but once you have a bigger room, you can feel like you’re just a number. If you want to build a sense of community where people say, I really know this person, I connected with them on a deeper level — having more intimate gatherings can really help you achieve that goal.

Kim: Smaller events mean people will feel safer. And the reason we do smaller events is so we have more flexibility to guide people, especially if they’re introverted or shy. We structure the events and have guided activities, which is much easier to do when the group is smaller versus 200 people in a room.


Mohamed: How do you cultivate community engagement over time? You run events on a regular cadence, and now in both Montreal and Toronto. How do you get that repetition going and keep bringing people back?

Linda: Definitely being regular with your events. If you have a specific theme or branding — like our women’s events — having a consistent schedule where people know when to expect you. People know My Creative Break is coming back in two months, so that helps attract people more regularly.

But also, making them feel something at the event. If they feel safe and connected, they’ll come back — not just for the experience, but for the people they met. We have a lot of familiar faces who come back. They come back for the people, but also in anticipation of meeting like-minded people. For the women’s events, they know they’re going to meet women facing similar challenges or working on similar things — people who can uplift and motivate them. That’s one of the ways to strengthen the community aspect.

Kim: We also really structure the interactions so people can have conversations where they feel like they’re connecting on a deeper level. When they feel connected to more people, they feel like they belong. And when they have that sense of belonging, they want to tell others about it and come back.

Linda: And one last thing — the after is very important. We encourage people to connect with one another after, we have a group to continue the conversation, to share wins with the people they met. Thinking about what happens after your event is going to dictate how your community grows. It’s something you have to think about.


Mohamed: Kim, because you have a marketing background — what are some of the marketing challenges of marketing an event? How do you get the word out and get people to show up? That’s the biggest fear most people have — that no one will come.

Kim: In terms of marketing, you really have to narrow down and figure out where your audience is. In our case, our audience is mostly on Instagram, so we’ve been using that to market our events. And I think the more people can see how your events are structured, what they can expect to feel — the more it’s going to attract them. We try not to just market it as an event, but show that when they come, they’re getting a whole experience, a whole community, and they’re going to leave feeling refreshed, connected, and just good overall.

Linda: I’ll add — word of mouth is also a big driver. People who’ve been to an event know what it is and share it with others. Sometimes they bring someone, sometimes they send someone. Our best marketers are the people who’ve attended the events.

But if you’re just getting started, definitely do what Kim said — survey your audience. Where do they hang out? What would they like to see? Get that crucial information first. Then you can figure out — maybe my audience is more on Instagram, but when we’re connecting more with entrepreneurs and business people, LinkedIn is also a place to market. Track everything and ask people at the event where they heard about you. Sometimes we’re surprised. Someone shows up and says they saw it pop up on LinkedIn, or it was shared by a friend on Instagram. Ask, gather that data, and then you can narrow down and focus on what’s actually working.

Kim: Or if you know your audience, just ask them directly — where do you go looking for events? What do you use to find things you want to attend?


Mohamed: Now you guys have been running events for some time — what would you say was your favorite event? Give us a fun story.

Linda: Oh, favorite event — there’s been a lot. But I have one in mind. One of our first live events, going from the pandemic to doing it in person. It was a mix of anticipation and not knowing if it would work. Things were just opening up. It was like a rollercoaster of emotions — we’re trying this, we don’t know if it’s going to work, we don’t know if people will show up. And then we still had people who were like, I don’t know if I can go yet.

I think because of all those emotions — and we did have a good turnout — the fact that it was our first one and we just accomplished it… we did it. I think it stuck with us. We designed something and got to see it play out. Kim, I don’t know if you have another one, but I think the first one is always special. The first event you host — whether it goes well or not, you’ll learn something from it. And it will stick with you.

Mohamed: Absolutely. The first time is always the one you remember the most.

Linda: Yeah, yeah.


Mohamed: In saying that, we are almost out of time — but if you want to subscribe to My Creative Break’s newsletter or connect with them on LinkedIn, I’ve got the links up on screen. We’ll also send those out in the recap email next week.

Wanted to give a big shout out to Gina from MWCN, the Montreal West Community Network, who is really enjoying this talk because she’s trying to run events for English-speaking communities in her area. This was a great chat.

Thank you so much everybody for joining, and thank you Kim and Linda for giving us the rundown on how to create a successful event and series of events. It’s been great chatting with you guys. Hopefully we’ll see you again soon.

Linda: Thank you for having us.

Mohamed: Amazing. Thank you everybody. And we’ll see you in the next one.