Humour + Vulnerability = Telling your story with Joanne O'Sullivan
3 Jun 2020 · 31 min
In this episode of the This Feels Right podcast, host Joel Silverstone interviews comedian, writer, and business coach Joanne O'Sullivan about the intersection of humor, vulnerability, and storytelling. Joanne shares her 20‑plus‑year career in stand‑up comedy, television writing (including award‑winning work and her one‑woman show She Grew Funny), and her recent YouTube series Incremental Improvements, which turned pandemic‑era anxiety into a format for sharing small, practical tips. The conversation delves into how personal loss and vulnerability can be transformed into compelling narratives, outlining a concrete storytelling framework—inciting incident, goal, stakes, failure, crisis, and resolution—and explaining why resolution can be a learning moment rather than a triumph. Joanne discusses how this framework applies to business contexts, describing her work coaching bankers and leaders to use authentic, vulnerable stories to build trust, overcome power imbalances, and make training memorable. She also outlines her pitch‑writing workshop for TV creators, emphasizing the importance of a clear protagonist, defined goals, high stakes, and a “dramatic engine” that balances drama and comedy. The episode includes a live improv exercise (the “last‑letter‑first‑letter” storytelling game) to illustrate presence and drama in storytelling. The interview concludes with practical resources: Joanne’s website (joanneosullivan.ca), her YouTube channel, and where listeners can find her workshops and the She Grew Funny show.
Chapters
You're listening to TFR, This Feels Right.
And welcome to This Feels Right. We've got with us Joanne O'Sullivan. So before we jump in, let's check in with our first guest, Joanne. How are you feeling today?
I feel great. It's a beautiful day. Sun is shining. Excited to be here and to see a friendly face. So thank you for inviting me.
It's great to have you, Joanne. We have known each other for probably close to 20 years. So I'm so glad you could be a part of the show. And today's show is going to be about humor, vulnerability, and how to tell your story with that. And really exciting also, we're going to be— Joanne is going to be sharing with us at the end how to write a pitch for your TV show. So stay tuned to the end. If you are new to TFR, This Feels Right, this is the show that's about how to influence others without manipulation. And what that means is we want to be able to connect to the logic when we're speaking to people, and more importantly, the part that we often forget is connect to the emotions so the other person goes, yeah, this feels right. And so listeners, if you want to be able to shift ideas and shift behaviors or shift actions Then you are in the right place. We've got our leaders and our experts to give us the tools and tips to help us get there. And Joanne O'Sullivan is— today's show, like I said, is about humor, vulnerability, and telling a story. And she is the right person to do this because Joanne is a stand-up comedian for 20 years, would you say?
Yeah, yeah, probably a little bit longer, but yeah, around 20 years.
In that ballpark. And has performed across North America. She is also a television writer for Canada's top top comedy shows. In fact, she's been a winner of the Writers Guild of Canada and a nominee for the Canadian Comedy Awards. So she has done this most recently with her most recent one-woman show. She's written, I think, 3 of them. Is that correct?
Yeah.
Most recent one is She Grew Funny, which just got to play virtually across Canada through the National Arts Centre of Canada. So quite, quite a prestigious opportunity for us to get to see that show, and we're going to unpack that a little bit more. And what's interesting also is, as we said, Joanne is going to help us write that pitch for the TV series, for a TV series, how that works. And because Joanne is also a business coach and facilitator and learning designer, has worked with many of the top organizations around the world in helping people in business communicate better. Is that right? Do I have that right so far?
That's right. Hey, it sounds so lovely hearing it all at me like that. But yeah, that's, that's, that's who I am.
I know you should be already retired. Like—
I know. Tell me about it.
The most recent project you have going on, Joanne, is a YouTube called Incremental Improvements. And this is really funny. This has got everything from how to cook with oils to how to give your cat a high five. So tell us, you know, where did this come from?
So being in quarantine like I am and being on social media like we all are, I've been noticing people taking this time to, you know, get— finally get into shape or learn how to run their marathon or write the next big book. And I was starting to panic that I wasn't doing enough, that I wasn't improving myself as a human, like making enormous improvements. And As a way for me to reduce that panic, I thought, well, I can do incremental improvements. I think I'm ready for incremental improvements. So I've been doing this YouTube show called Incremental Improvements where people come on and they teach me something. Like you mentioned, like I knew nothing about cooking oils. So I learned a little bit of how to cook with oils. I learned how to, you know, use your pets as a source of amusement while you're in quarantine. how to buy, you know, good beer on a quarantine budget. So, but with the funny— I'll be honest with you, Joel, the funny thing about that show is I thought it would be a comedy.
Mm-hmm.
But the thing that people are returning to it for, the thing that people are really enjoying, are the little tips. Like, people really are enjoying the tips that they're getting. So it's still funny, but now I'm actively seeking out like genuine tips for just small little things that you can do to do, you know, an incremental improvement in your life. And people have been liking it. So—
Well, Joanne, this absolutely, you know, this goes with your brand, which is always how you're able to think of that next question. You sit, you ask the question, or you say what people are thinking, but not necessarily, but like deep down, the little thing that they didn't realize they were thinking about going, oh yeah, how to, how You know what? I thought I knew everything about oils, but I never really looked it up. And so you ask the right questions. You, you ask what we are thinking but maybe afraid to say, or we didn't even realize we wanted to ask that.
It's funny, you just pretty much defined the root of comedy and humor, which is making people recognize themselves or recognize something that they're thinking that they weren't quite able to articulate. But the moment they recognize it, not only is it an aha, but it's usually a moment that makes them laugh. As well.
You know, I like— that's the word, articulate. They weren't able to articulate it. So let's go into, you know, I was watching SheGrewFunny, and, you know, for those who haven't seen it yet, strongly recommend it. And we'll give you the links to where to watch that. This is a— this is the show that's about— you realized— well, first off, you lost your mother when you were 6, and when your daughter turned 6, you realized, well, this is the What happens if she lost her mother? And this sort of created this whole spiral of how you can create a one-person show. And this is where I want to get to, is how do you create a show that has this vulnerability, something we're very uncomfortable to watch, talking about death? And you got some great lines in there, which is, you know, people are uncomfortable about death, and your job often is to make them feel more comfortable about it.
Yeah.
So how do we do that? How do you— how do we create a show that's That's vulnerability, but still makes us feel comfortable.
Well, I think there's 3 things. I think first of all, we all have those stories. We tend to tell ourselves that I don't have a story that anybody would want to hear. Um, but we all have those stories. If you look back through your life, there's gotta be a moment of vulnerability or, or pain or learning or something that's occurred. So the first thing is just to identify those life stories of your own. One of the biggest challenges for me, the second challenge is believing that people want to hear it. To be honest, like as a storyteller, Right. this idea of will people want to hear my story? And I think a great learning for me is realizing and teaching myself how much stories connect us. And how people are actually hungry for other people's stories because it makes us feel connected on so many different levels and we learn from each other. And then the third thing is, particularly when we're talking about stories of vulnerability, is being ready to tell that story.
Right.
So there was probably a time in my life where I wasn't ready to talk about my mother. And I mean, it took me many years to get there. And being ready to tell a story means what you're trying to evoke from the audience is empathy, which is connection. So they understand, truly, they get it. They may not have lost their mother, but they can respond to a story of loss or a mother being worried about her own child. Like, there's places that they can empathize with, as opposed to sympathy, which is— sympathy is if you're not ready to tell the story. Sympathy is what you get from a friend. Right.
Right.
The moment after something terrible has happened and you need support. I think by the time you're telling a story, you should have— be ready, make sure you're ready to tell that story. For me, that makes the audience feel more comfortable in receiving it because it's different than therapy and it's different than getting support from a friend right after a major loss. Because empathy is a beautiful thing. Yeah.
And I like this connection you were talking before about When people can recognize themselves, that's the key to humor. People can recognize something in themselves but maybe not articulate it. And so when you're talking about the loss of your mother, A, you're feeling comfortable to tell the story. Maybe we didn't lose our mother, but you're finding that place of connection where we're, we're both sharing in the story versus, oh, woe is me.
Yeah, my goal and my hope in all of my storytelling is that the audience will walk away having reflected on something about themselves. in a way that is helpful and that has made them feel a sense of community. So that's my goal. And I really had to start believing that I was capable of doing that, that my stories had a worth and a use beyond, I just want to talk about myself. But you really have to believe that and understand how important storytelling is across generations. It's a technique that not only for learning but for community and just to, yeah, to connect. And we all need to connect so bad right now. So I think it's so important.
We do. And we're going to talk about how you help people who are in business and bankers specifically. How do you help them with vulnerability and telling a story? But maybe before we go there, you know, as you just hinted, how How do we tell a story? What's the, what's the steps? Or is there a process to it? How do we— how does one tell a story?
It's a really great question. Like, there's like a storytelling model. So stories that catch people's attention are usually stories that involve a challenge. Like, you want to overcome something, so you build suspense. So this is what I want. And can I, can I get to that thing? So, you know, a very basic structure, like with She Grew Funny, is, you know, having a goal. So something, an inciting incident, which is the thing that starts the story. So for me, it was my daughter turning 6.
Right.
And recognizing myself in her. And then a goal. So for me, a goal, my goal became changing myself so she wouldn't take on my negative traits that grew out of me dealing with such a great loss at a young age.
Right.
So then I get a goal and then the stakes. If you learn anything from this is what are the stakes of your story? You need to communicate those stakes really clearly because that's what makes the audience root for you. So for me, my stakes were I didn't want to pass down something dangerous to my daughter. That's really important for a mother. So stakes. So inciting incident, what your goal is, your stakes. Then for me, and then it's failure, failure. So I tried this, I failed. I tried this, I failed.
Right, that's good. Yes.
Crisis. Oh no, what's going to happen? And then after the crisis, you try one more thing, resolution. And the resolution is either you succeed or the resolution is you fail. And from each one of those things, learning takes place. So for me, I actually failed. I wasn't able to fix it. fix the things in me because I realized that that's made me who I am. And I was thankful for those things. And that's what made me funny. So she grew funny. You know, my flaws are what make me funny. And that's a really important part of my personality. So that was my learning that I may not be some of these other things, but I'm this and that's okay.
Yeah.
And so I guess the Coles Notes version is, you know, inciting incident, Goal, stakes, fail, fail, crisis resolution, whether that be success or failure.
And I like that resolution doesn't have to be— because we always think the resolution has to be, and they closed the million-dollar deal, and my daughter is now the president of Sony.
This is my hope for my daughter.
So, but, but the resolution is And this, this, and this is, you know, this is who I am and this is what has made me. And this is because I like that.
Your resolution is the learning. Like, what did you, what did you— either you do achieve it and then you learn how to achieve it, or you didn't. And maybe it sent you on into something more important, or maybe it just wasn't the right moment or whatever. But yeah, the resolution doesn't always have to— because our resolutions aren't always success. And those stories can be the most impactful and the most powerful, particularly if you are in a leadership position. If you are willing to tell stories where you failed in a leadership position, that really will humanize you and will help the people who work for you and with you be more comfortable with you. They will believe in you. They will just respect you more for being willing to tell that story. Yeah. But mostly it will, bring humanity to you and less fear, which makes people work for you better.
Yeah, they're actually more motivated to do that. They're gonna, you know, 2 things, right? Do I like you? Do I respect you? Check, check. Yes, I like you and I respect you. Well, this is a good segue then to talk about, you know, how you have helped bankers tell stories. And what you just said also was really interesting was because I think the challenge for a lot of us is We're so objective-focused going, I don't have any stories because I don't have this— I had this personal best in marathon, or I closed that multimillion-dollar deal. And so we think that's kind of our stories is what the outcome is. But the story is that learning piece. So let's switch gears here and talk about bankers and how do you help them in telling stories and vulnerability?
Well, I think for me, With anybody in business, the first step is explaining why it's important.
Mm-hmm.
You know, getting just buy-in on the idea. You know, something that you said, do I like you, do I respect you? From a customer perspective, we, in a moment in time where people can change business relationships on a monthly basis and do, there's few things that will keep somebody with you as much as them just liking you.
Mm-hmm.
And a lot of that comes out of human connection. So being able to connect with people, and one of the best ways is through storytelling, is such an important skill. And the way that I teach that when I am talking to bankers, if I'm coaching, is through telling my own stories and being vulnerable, because I think showing is much better than telling.
Right.
You know, when I come in to train, there's an inevitable power imbalance as the trainer and I come in. And some people respond well to that power imbalance. They like to be taught. Some people immediately push back against any kind of authority. There's all sorts of different things that happen when somebody is confronted with a trainer or a coach.
Right.
So if I start those conversations, if I identify things I'm training them that I've also struggled with, I immediately change the dynamic into more of just all people in a room, all humans working together, humanizing the situations. It makes people so much more open to that training.
Well, you're modeling what you just said. When leaders tell a story about their own failures and they have that sort of vulnerability, You come into an environment where nobody knows you and you have to get buy-in pretty fast.
Yeah.
Because we're gonna spend the whole day and we're gonna be doing stuff that everybody has probably been having nightmares at 3 o'clock in the morning about. Oh my God, tomorrow I'm gonna spend a whole day having to tell a story in front of my colleagues.
In front of people. I'm gonna have to— yeah, so first is just getting buy-in on storytelling and people will remember, like they can almost immediately remember a moment in their life because we— well, here's the other thing, we remember stories. We don't remember training. Like if you leave a day of training and you've learned like 10 things and heard 2 stories, you'll remember the stories.
Right.
Right? And so it's our job to make sure that those stories relate to what we're teaching so they will take that with them. But as soon as you say that, people will go, oh, that's right, like that training last week. I don't really remember the training, but I do remember the story of the woman relating to a customer and that customer getting mad and out of fear she did this and then it worked. And so then they'll remember.
Well, that's what, that's what branding is, right? We'll remember Joanne the coach. Oh, wasn't she the one who talked to you, does the one-person show about her mother dying?
Which is funny.
Yeah, which is funny. Yeah, yeah.
So there we go.
But that, but that's kind That's kind of how we remember the person. We don't remember, oh, do you remember Joanne? She had that 10-step process.
I do not want that to be on my gravestone.
Yeah.
10-step process.
Joanne, 10-step process, was all of it. Yeah. All right. Let's take our little commercial break on this note about storytelling. And Joanne, We're gonna do something here that we like to call on the show Improv Improve Your Communication Style. And today, I'm ready, Joel.
I'm ready.
Well, let me tell you what we're gonna do, and then let's see check in. We're gonna do something called last letter first letter. So we're gonna tell a story, and I'm gonna get whatever the last letter of that. person says has to become the first letter of your sentence. So the last letter of the last sentence becomes the first letter of your sentence.
Okay. Got that? Nervous.
Let's come up— yeah, we all are. Oh, we're doing— we're following your storytelling. We're having drama.
Okay. Oh, that's right. Suspense.
Yeah, suspense.
This is where I show people how to fail.
Yeah, that's right.
Here we go.
I'm just trying to think of a story. We need a title for the story. Let's see, we were talking about 10 steps. Oh, perfect. We're going to talk about the— we're going to call it the steps to cooking.
Great.
Yeah. All right. So I'll start us off if that makes you feel a bit more comfortable. So listen for the last letter. You ready?
Of your last word.
Of my last word. Yeah, exactly. Here we go. Joanne, it's my wife's birthday coming up and I'm gonna try to bake a cake.
Everyone thinks that's an amazing idea, Joel, but before you begin, what is your wife's favorite flavor? Right.
That is so important to get the flavor right.
Uh, thank you for acknowledging how good my idea was. I appreciate that. Might I suggest vanilla?
Aha! Vanilla, of course! I can't believe I never thought of that. That's gonna make it so easy. Thank you, Joanne.
Any— oh, every time you ask, I'm gonna come up with a great response, Joel, because that's my job.
Booyah! And we had bravo! Great. I love that, that you could remember that Joanne ended with an E and not an N.
No, I could remember E. I couldn't remember that anytime started with an A and not an E.
Okay, anytime, anytime.
Right.
Lovely. All right, how did that, how did that feel?
Well, good. That was fun. It's a good wake-up. It's a good wake-up the brain exercise.
It is. It's, it's really good. And, you know, it's thinking about all we're talking about storytelling is, uh, you You know, it's so true. We love drama. We love when the stakes are high. You can tell a story about baking a vanilla cake for your wife's birthday and it becomes engaging all of a sudden when you really are invested into it. You're not, you're not worried about what's coming next. You have to be so present. And I think that's one of the gifts that comes out of that exercise.
Yeah, it's so true. It's so true. Like how present you have to be to play that game.
Yeah. You can't think of what's coming next.
No.
No. So listen, let's— before we find out more about where to— before we find out where to get more about you, let's, let's, you know, we saved this for the end. This is really interesting. You run workshops based on your years' experience of writing for so many Canadian comedy shows. Again, nominee for a Canadian Comedy Award. Let's throw that in there. And winner of Writers Guild Canada. Let's throw that in there as well. Bravo. Now you run workshops on how to write a pitch for a TV show. So, you know, what are some headlines from this? What are some things that we could take from something like that?
Well, can I just give a little bit of background about how it started? So I've pitched, so I'm a bit of a story, I love stories. I'm a bit of a story machine. And I have probably pitched about 25 or more shows and I've optioned quite a few. So because of that, people started coming to me and saying, I need to write a pitch document. to pitch my show. And I used to just do it for friends. And then I realized this is a skill that people need to learn how to do in order to go to either producers or television networks, or even it's all the same kind of storytelling. And so the headlines of what I teach is mostly when people come to me, what they are struggling with in terms of this pitch document is how to get the show in a concise, manageable document that is a clear— that clearly tells their story. So for me, it's mostly about that structure that I told you right at the beginning. It's always the same thing. It's like knowing who your protagonist is and really knowing who your protagonist is and knowing how they became who they are today, knowing in a really clear way what their goal is. And I teach people how to articulate that, like what is their goal and what the stakes are. The most important thing, because people will not tune into your show unless they care about the characters. And the only way they're going to care about the characters is if they have some kind of stakes. And then I talk about on the dramatic side how to create a dramatic engine The stakes and the goal rub up against each other to make a dramatic engine. On the comedy side, that happens in the— and the further these things are apart, the funnier it is. Like, the further things are apart, the more comedy you're going to get in that engine. And I go into specifically how to create those engines to convince an executive that your show has legs, not only past the first season, but the second season.
Right.
and the third season, and that all has to do with your protagonist, their goal, and their stakes. And then I just talk to them about how do you make people see your show? Like when I'm reading a document—
Mm-hmm.
I need to understand exactly what I'm gonna be seeing day to day. Like what is the actual show? So we talk about clarifying that, and then the different characters. And it's about a 4-hour-long workshop. And at the end of it, what I have found, when you work really hard on a pitch document, you can't help but clarify the show. And the feedback that I've gotten is that people come in with an idea of what their show could be, but by the end of it, they leave with knowing exactly what it is, what's amazing and unique about it, and how to pitch that in a way that sells. And I've been doing it for years, and it took me a while to come up with this formula, but I'm very proud of it. And I think that I've helped some people And it's— and to be honest with you, it's really just boiling it down to what is your story. It's same with the story, same with the show. Boiling it down. And we find that difficult to do. We tend to do this when we, you know, but boiling it down to a straight line, to a straight narrative of what, what your show is, um, is, it's fun.
I, I think this is So timely. I think as we're going through a new normal for a long time, I think a lot of people are thinking about how to reinvent themselves. And maybe some people are thinking about, hey, there's an idea for, for a TV show in this. And again, it's not thinking about the outcome, what the end result is, because it's about thinking of the journey, I think, is what you're saying. And who are our main characters and what their growth journey is and, and what made them. So I think that's, that's a great way to look at it. And I think this has other avenues as people are looking to reinvent So maybe you're not looking to write a TV show, but maybe you're just looking to define your personal brand or your business's brand. Yeah, yeah, you're looking to define that in different ways. So I think this is a great exercise for people who are looking to— and we all have to now kind of reinvent ourselves because it's— things are changing.
Yeah, absolutely, 100%.
So where— let's segue now to learning about where can we find out more about this. So first off, where if we are interested in this workshop, Joanne, where can the listeners learn more about this pitch writing workshop?
So I have a website. It's www.joanneoseleven.ca. There's another .com. She's also a writer. She's lovely. We've met on Twitter.
Okay.
Really nice. But she's .com. I'm www.joanneoseleven.ca. And the Incremental Improvements, I think it's just YouTube Joanne O'Sullivan. And the She Grew Funny, if it's okay.
Yes, yes, yes.
If you want to watch that, it's still up on my Facebook page. It's public. And you just go, I think, just on Facebook, Joanne O'Sullivan, O apostrophe. I think I'm JoanneO'Sullivan.520 is my actual thing. But just Google me, go on Facebook, Joanne O'Sullivan, and scroll down a bit and She Grew Funny will come up.
And, and if we go to your website, this is where we're going to find out about the scriptwriting. Is there a link to the SheGuru Funny on your website as well?
No, but there's going to be soon.
Yes. Yeah. I think just, I think just add it on your website to the Facebook page.
And yeah, you're so smart. This is what I need. You could do incremental improvements on how to market myself.
There we go.
I'm just catching up to all of these things. I'm not very good at social media and all of that. So I'm just sort of learning how that all works. So maybe that's— maybe you can come on my show and do that.
Lovely. What a great idea that is. Joanne, where— if we are interested in finding— if we are interested in just following the adventures of Joanne O'Sullivan, is it Facebook, Twitter, Instagram, LinkedIn?
My website has a link. I also have a podcast. So my Facebook links to I mean, sorry, my website, joanneosullivan.ca, that links to my workshops, to where, well, back when live shows happened, it also promoted where I was performing live as my standup. It links to my podcast. So that's probably the best hub. And soon it'll have the link to She Grew Funny as per your amazing suggestion.
Perfect. Well, you see, we had, we followed, I followed your story. We had fail, fail, fail, and then we had a resolution. The resolution was just put the link on it. So there we go. We had an incremental improvement in the story.
What is the resolution these days? Just link, link to it.
Add a link. Listeners, thank you so much. Joanne O'Sullivan, thank you so much for being a guest on the show. This was a lot of fun.
It's a pleasure, Joel.
We will see you next week on This Feels Right.
Yay! Bye-bye. Bye.
Thank you so much for listening. And if this felt right and you would like to see this interview, then come on over to our YouTube page at youtube.com/thisfeelsrightpodcast. Or join the conversation with our Facebook group at facebook.com/thisfeelsrightpodcast. Or if you just want more influencing tips and communication skills, then please connect with me on LinkedIn, Joel Silverstone, or come on over to Silverstone Communications at www.joelsilverstone.com. I look forward to connecting with you.
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