I am a strange mix of shy and outgoing, someone who simultaneously has stage fright and is totally comfortable in front of a crowd. Perhaps the best illustration of this comes from this week’s challenge – a double shot of workshops.

Sage has been giving storytelling workshops for several years now. I’ve even worked together with her to deliver one in Chhattisgarh.

From the minute I was up on stage with Sage I felt 100% comfortable. While Sage was talking about telling, I was talking about how it relates to business. I’m very sure of myself there and confident.

But despite that the idea of actually joining the workshop as a participant made me nervous. Being a student is something that makes me feel off balance. For a little extra challenge, I add an additional rule to today’s workshop – I would talk to strangers.

I help Sage set up the room and after a few minutes, people start showing up. One of the first to arrive is an improviser that Sage and I already know. One of the first things she talks about is that she feels completely safe improvising but the idea of being herself up on stage telling a story felt more vulnerable. This echoes in my head for the rest of the day because I realize I’m just the opposite. When I’m doing something I’d normally do that feels totally comfortable. But, whether working to learn storytelling – something I’ve done only a little of, or being endowed as a sea captain in an improv scene, my mind gets distracted by the thought “Am I doing this right?”

In today’s workshop, though, I’ve resolved to push through that and listen to what actually scares me. When Sage asks for volunteers if I feel hesitation I jump up before my mind has a chance to react. As a result I’m up on stage several times. The exercises are mostly fairly tame, though, and I’m surprised at how comfortable I feel.

In the end, the workshop goes really well. I’m excited about the idea of pushing a bit more and actually getting back up on stage to tell a story. I’ve already begun working on one. When it’s done I will share a video here – watch for it in a few weeks. In fact, it feels so easy that I worry it’s a cop out. But in the end I think it was a valuable lesson: those things that feel like they might be uncomfortable are likely to be completely comfortable and fun.

The experience of pushing my performance boundaries is so fun that the next day I decide to push my limits by going to an improv drop-in. This requires a bit of background.

In 2011 I decided to take an improv class to do something totally different and face the fear of unpredictable interpersonal interactions by experiencing it so much it becomes routine. I love the class and sign up for another. After my second class I audition for a team and perform a few times a month. For the next two years I find myself truly enjoying myself. The seconds before going on stage feel like the top of a roller coaster and the show feels like the rest of the ride. I don’t know where it’ll go and am amazed at the discoveries. When I’m not rehearsing with my team or performing, I’m going to drop-ins and taking classes from visiting improvisers from around the world. I have never been on stage this much in my life and I am having so much fun.

But over time things started to change. One team I was in had a member who would all but count laughs as we performed. If the show didn’t meet his standards, he would already be saying how much we all sucked while we were walking off stage.

And then one night I am in a drop-in where names are pulled from a hat to create ad-hoc teams. I am in a scene with another person in a grounded scene. Another team member pulled a chair in front of us as if we were characters on television and then proceeded to say how terrible this show was. These guys can’t act, they’re not funny. Where are they even going with the plot? The scene ended and so did my interest in improv. I tried a couple of times to perform after that but it was hard to get that image out of my head.

But now I’m going to an improv taught by a friend of mine. Sage is there and it turns out I know one other person. The environment is inclusive and the teacher is taking a different tack than others I’ve worked with. The point of today’s class is to make mistakes. Find the uncomfortable situations and see where they go. Realize that often what is funny about a scene (or a time in life) is the very fact that we’re dealing with something uncomfortable.

And so I upgrade my challenge a little bit. Just like in Sage’s workshop I’m going to listen to my inner voice and when it says “Oh HELL NO!” to someone asking for a volunteer I’m going to get up and do it. And in the process I have a great time. I play two games that I’ve always been nervous to try – one where improvisers perform a scene and then pull random sentences out of a bucket that are injected in to the dialog and often don’t make any sense, leaving the performers to justify what was just said. At one point the teacher asks for volunteers for an improvised talk show. Three people will work together one word at a time to answer questions given by a host. Giving a word sounds easy enough but when we’re asked who wants to be the host my mind gives a big “no” to that. And so there I sit in the host’s chair, interviewing the owner of a company that sells “Spooky Shoes”.

I have a fantastic time and am so pleased to have gone there. Years before I overcame my fears the first time, I used to avoid going to improv shows out of fear that someone on the stage might interact with me at all – they might ask me my name or a simple question like “What do you do for a living?” or “What did you have for breakfast?” Today I once again enjoyed not only watching it but doing it. Had I avoided it I would not have had the experience of playing MegaJenga with lumber in the rain with my brother or giving birth to a baby named Jesus. Both the storytelling and improv workshops were fun – and not only that, the most fun parts were where I got to be uncomfortable and unsure of myself for a bit. These are the kind of things I wish I could go back and tell my past-self about.

At the end of the improv drop-in the teacher talks about the “lines from a hat” game we had just played and how the fun of it was that any time we wanted we could grab something out of the hat and get ourselves in trouble. He went on to say that we could do the same in life to make things interesting and inject a little bit of fun. We can do something different and a little risky to see what kind of trouble we can get in to – and what it feels like to be in it and find our way out of it. Which, when it comes down to it, is the point of this whole project – and what makes me the happiest in life.

For those in Toronto, you can take a weekend intensive workshop with Sage on the 25th and 26th with a class performance on the 31st. Sign up here.

For those who want to try a fun improv workshop (or often a series of classes) check out Play With Fire Improv.

Have an idea for an adventure? Let Sage know with the form below and she’ll take me on a surprise adventure to do something I’ve never done.