358: Crossing the Cringe Chasm when Taking Career and Creative Risks with Henna Pryor

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What's next? This is a question we're all having to ask and answer more frequently. I'm Jenny Blake, your host of the Pivot podcast and author of the only move that matters is your next one.

For show notes from this episode, visit pivotmethod.com podcast if Change is the only constant, then let's get better at it. Here we go.

Welcome back, Pivoters. I am so excited to bring you today's guest, Hannah Pryor. Because as we turn the corner into the ninth year of this podcast, longtime listeners know that I call this the Awkward show. So when I got the memo that she had a new book come out called Good Awkward how to embrace the embarrassing and celebrate the cringe to become the bravest you, I just knew that I needed to have Hannah on the pod. And in fact, instead of reading her professional third person bio, I'm going to read one from the very back of her book called mom poem that her 10 year old son or at the time 10 year old son wrote on her iPhone that surprised her in her notes. Mom is amazing. Her blazers are blazing. She takes Ruby on walks and did two TED talks. She embraces the embarrassing and celebrates the cringe. And she watches Schitt's Creek. No, actually binge. She's a global speaker and a thrill seeker. She's married to Ian and loves vacations, especially European. Hannah, welcome to the show. Thank you.

I wish I could have written something that good myself, but leave it to a 10 year old to give you the best bio ever.

It's the best bio I've ever seen. It's so good.

I just opened my phone one day and into my notes app to make a note about groceries and I was like, what's this? This? Oh, this is going in the book. No brainer.

Well, I'm so happy to have you here and I just love that you wrote a whole book about this topic of embracing our awkward selves. Because I feel so awkward so much of the time. And I learned through your book that in fact, bravery requires being off balance. And I want to just start by reading something personal that you shared about the book itself. You say the idea of releasing this book into the world without knowing how you'll receive it makes me cringe. But it makes me cringe even more to imagine walking through life as a person who doesn't write and release the book that matters so much to her because she's worried how it will land. Either one is a risk. Can you just make the connection for us between risk taking and awkwardness?

Yeah, I'd be happy to. And it's funny, Jenny, I haven't had anyone read me those words back before. You've just done that for the first time and it still lands for me in almost a full body visceral feeling the way it did when I was writing it, even though the book's been out for a few months now. So what is the relationship between awkwardness and risk taking? Well, to make that relationship clear, it helps to start with a very high level definition. Awkwardness in the context of what we're talking about is an emotion that people feel that is a social emotion, meaning that we don't typically feel awkward by ourselves. It's usually something that exists when other people are around and watching us. And it's an emotion of discomfort. It doesn't necessarily feel good, but it shows up in those moments that the person we believe ourselves to be or our true self is momentarily at odds or facing a gap between the person that other people see on display. So more simply said, our internal identity for a moment doesn't match their external reality. And in that in between space, we feel awkward. Now, what does that have to do with risk taking? Especially risk taking at work or professionally? Truth of the matter is awkwardness lives in uncertainty. And often for professionals, there are very, very few vocations that are completely isolated. There are a few astronauts, polar explorers. You know, those folks tend to work very, very much by themselves. But for the most part, most of us work in places where we do have to interact with other people. And when we're taking any kind of professional risk, whether it's as small as raising our hand in a meeting with an idea or a little bit larger, like negotiating or advocating for ourselves in a promotion or, or really innovating or taking a wild big step in favor of a big idea, all of those involve taking a risk in front of people socially and have a very strong possibility to invite the emotion of awkwardness. And so we don't get to avoid that emotion. It is unavoidable in a world of uncertainty. So we have to actually learn how to get good at it.

Well, I really appreciate you defining awkwardness, especially in the context of other people, because one of the big themes of this podcast over the nine years is also talking about perfectionism and people pleasing. And those are two things that are also in great tension with awkwardness and wanting to be approved and liked by people. And I think that's where so much of the risk comes in. We're going to talk about crossing the cringe chasm, which is such a good phrase. But the reason I read you that excerpt of your experience with the book is that I wouldn't have done anything. I've been building an online platform for almost 20 years now, and I feel awkward every single time. I always say I feel awkward in these interviews in real time. Thankfully, I have an editor. I feel awkward once they're live. I know what I did wrong or said wrong or where I flubbed. And it's just built into so much of what I do that I just learned to live with it. And I have a mantra 5149 like I just have to tip toward action by 51%. But 49% of me feels awkward, embarrassed, cringe, and all the rest. And so I just really appreciated you relating.

So I love this framing of 51:49 because I think a lot of people have this misconception and this is one of the explorations in the book about if I don't feel fully confident, then I must not be ready. Or if I don't feel like I can go into this cool as a cucumber, then it must not be ready. But the irony is that the most confident people we know experience exactly what you've just described. They are rarely, and I would probably say with some certainty, if ever feeling 100% confident or 100% ready, they've just learned how to become friendly with that feeling in favor of their own growth and improvement. And so I love the way you assign numbers to it.

I always think that writing a book kind of signs you up for a front row seat to that topic. And the book gods make damn sure that you have it embodied within you. What was your cringe chasm while working on the book? And like, even getting the confidence to tackle this type of project for the first time at all?

Oh, I had so many cringe chasms along the way. I think when it came to actually even declaring again, it doesn't matter how accomplished you are. So if you look at me on paper, here's me bragging about myself on paper. There's no reason that I should have felt shy about writing a book. I have done all the things, have all the accolades, the great degrees, the great accomplishments. I always jokingly say in my keynotes that my immigrant parents are very proud. So on paper, I've done all the things, why not me to write a book. And yet, when I even decided to do it, just even getting comfortable with this idea that I'm someone whose voice people would want to hear, that felt like a giant cringe chasm that I needed to cross. Who am I to be an expert on a topic? Who am I to tell people how they should improve or how they should live? And so I really had to do a lot of mindset work around that. And then like every author I know, yourself included, every step of the way, it's, are they going to read this chapter and think it's fluff? Are they going to think it's something they've read before? Are they going to think that I'm less of an expert or too serious or too funny or too, you know, name your adjective, X, Y, Z. And then we come to promotion and marketing. And what that requires of all of us authors, whether we like it or not, is talking about how great the book is and how much value people are going to get from it. All of which feels extremely cringy, extremely awkward, because here I am saying, look, everybody, look how great my book is. Look how great I am. All of these moments invite that potential for what we perceive to be other people's external reality of us. Gosh, all she does is talk about herself. Gosh, all she does is talk about this book, right? And then I'm so consumed with other people's external reality versus what it is that I want to do. That tension that exists in between, it doesn't go away. And so I really had about a million of those moments along the way.

And it's so true. You talk about the approval paradox in the book and the approval mindset that the paradox being, of course, you want people to like the book, of course you want readers to resonate. And then, as you said, there are all these moments that you're standing out on a ledge kind of, yes, there's a team behind you, but kind of by yourself, saying, here, I did this. I created this. What do you think? And so at the same time that you want people to love it and spread the word, and you want the book to climb the charts, you have to at the same time detach from those outcomes in order to do it at all. And I guess that's part of the chasm that you talk about.

Exactly right. I mean, I think when it comes to stepping out from behind any curtain, and now, no matter what, again, what vocation, what life choices people make, there are going to be moments where we need to allow ourselves to be fully seen. And, you know, outside of just the narratives of, you know, staying in our comfort zone, we know this one. What often people don't realize is that this idea of the cringe chasm also speaks to when we jump, people are going to be watching. People are going to be seeing us when we're stepping out into something new. If it's again raising our hand in a meeting, offering to do a presentation, what we are essentially signing up for is to be seen more than we typically are in the position to have other people's scrutiny. But some of the important lessons in that work are we have to understand that we have a very strong perception of how deeply we think people are watching us, how much we think they're analyzing our every move. And frankly, that data just doesn't shake out. People do watch us cross the cringe chasm, but not with nearly the intensity or the focus or the obsession that we think they are. And that is so freeing when it comes to standing at that edge, wondering if we should jump, because more often than not, the answer is yes.

And you're so good about providing all the social science research. So that's the spotlight effect that we think others are watching and paying attention to us far more than they actually are. So we can link to an article on that in the show notes. And then you also talk about the pratfall effect, which I found very interesting. Can you tell us more about that? Yeah.

The pratfall effect is probably one of my favorite pieces of research in the book. And the pratfall effect is simply this. When we are people who are generally seen as competent, smart, skilled people who prepare, then the research actually shakes out this idea. It's from Elliot Aronson, a social psychologist. It shakes out this idea that when we are generally people observed and seen as that type of person, that when we make a misstep or when we make a blunder, it actually not only doesn't hurt us the way that we think it will, but it actually helps us. What it does is it knocks us off this proverbial pedestal that people may put us on. And it humanizes us. It makes us warm, it makes us likable. So in its simplest terms, it explains that often when we see a celebrity mess up, someone that we perceive to be glamorous or always saying the right thing, when we see them mess up, or snort and laugh, or Jennifer Lawrence trips on her dress walking up for the Oscars, when we see these things, in fact, we not only do not judge them harshly for it, we actually like them even more. It humanizes them. It makes them warm and likable. So what is this saying? What this is not suggesting is that you purposely dump a cup of coffee on your lap or you purposely mispronounce someone's name. But what it is saying is if you are generally someone who does the work, who comes in prepared, who. Who is generally smart, skilled, capable, competent, and you flub up, not only is it not hurting you the way that you think it is, often it can actually have a positive effect. And that is great news for those of us that are so worried that every little thing is going to cause us trouble down the road.

And just knowing that not only does it not detract, that oftentimes it is the thing. I think one of your studies showed that people are like three times more likely to relate or resonate. It reminds me how on the TED stage, they end up editing this out. But basically, the TED speakers are so rehearsed now, and there's such a gauntlet of practice that they have to go through that a lot of them sort of panic on stage because you're in the room, you're in front of all these luminaries and billionaires, and many people end up forgetting what they're trying to say because of that level of nerves. And without fail, almost every single time they forget, there's a pause and the audience starts clapping and you can see the anxiety, like, melt off of them. And they just take their time and they restart. And of course, I think now they edit those out of the videos. But you see that when people mess up like that, the audience in the room actually starts rooting for them like we're on your team. You've got this. They're clapping. They're like, you can do it. And even though the person is probably still mortified years later that they messed up, in fact, in that moment, the audience likes them more than if they were perfectly flawless, scripted perfection.

I love stories like that because it reminds you of the humanity. I think. Often we worry, listen, the digital atmosphere can feel like a cruel place. I think we all know that people are very quick to be throwing daggers and evil eyes at people online. It's easy when you're behind a keyboard. But the truth of the matter is there's equally, if not more, stories like the ones that you're describing where we genuinely are rooting for each other. And even if we're not rooting for each other right away, there's still another positive potential here. And that is, it gives us an opportunity to actually elevate our perception in the eyes of the people that we blunder with. So I'll give you a specific example. There was a conversation. When Sheryl Sandberg first wrote Lean In, a lot of people heralded this as a great book for people trying to take control of their careers. It was a boon for women. But then there was also a very large population of people that said, hey, this is a book for privileged people. Easier said than done. You don't get it. You don't understand us. And in that moment, again, Sheryl Sandberg, who's trying very hard to speak for the voiceless or to create a conversation that's supposed to help people. I'm sure when she got that sort of wave of feedback, it was embarrassing, it was awkward. But in that moment, she had a choice to make. And the choice that she ended up making was listening to that feedback and incorporating it in every Talk interview panel she did after that. And she was very quick to say, you know, in my early release of this book, there was a few things I missed. I didn't talk about this. And what happened as a result is, is she became even more beloved. She became more recognized and more appreciated by an even greater population. So within that embarrassing situation was an opportunity to actually improve her standing, her personal brand among more people that mess up. That blunder actually turned into a great opportunity for her to turn things around, Even though in the moment it was probably hard for her to see where's the likability in this. We just have to be able to have that thinking cap on.

We'll be right back just after this.

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And you also point out that people of higher or even the highest status. It kind of helps. Like you need something to release the pressure of that. And the people at the higher levels can benefit more from self deprecating humor. I mean we can all benefit from humor of course, but I love what you point out just now and in the book around the shine of social media. There are so many filters now and so many ways to kind of puff ourselves up. I'm not even on social media. Yeah, but when like the reality just has nothing to do with that, I can't let this recording go without saying. How do you cross the cringe chasm? ICC improvement comes after cringe. It's like those are the learning moments and the moments of self improvement. And you say even self identity where that becomes more important than other people's approval. And I just love remembering that and reminding ourselves of that.

I love the framing of the ick moments. Right. The improvement comes after cringe because what it's essentially getting at is that feeling in our stomachs when we have to put ourselves out there. When we're risking social approval, that feeling in our stomachs is the most normal, natural thing there is. We can go on and on about how we are all cave people at the end of the day, our brains are evolved for social belonging. But what's important is as long as you are making that jump over the cringe chasm in the favor of something directional, aligned with your values, not every cringe chasm needs to be jumped, not every fight needs to be fought, not every awkward moment is your responsibility to handle. But the key differentiator here is if there's Something that inside of you, you want to do that is aligned with your values, your goals, your mission. It's slowing down, having the courage to slow down long enough to name the trade off. So you mentioned earlier in the case of the book, again, the idea of releasing a book that I didn't know if anyone was going to read or like or be into invited every cringy, awkward feeling in my body. I felt like I was 12 again with the idea of even doing this. But then I also had to recognize that there was something on the other side is this was a book I really wanted to write. And either way, it was a risk. Either I don't write the book that I really want to write and I abandon that dream, or I jump. And a few people, a few Internet trolls say they don't like it and I have to withstand that. But either one is a risk. And I think often when it comes to awkward moments, our fear of what they feel like or trying to avoid them overtakes slowing down our thinking. The way we need to evaluate what's on the other side of this. Each moment, each choice is a double sided coin. It's not one way.

Speaking of trolls and reviewers, when my first book came out, I got a one star review. I still remember his name, Manny, of course, because our brains are programmed and longtime listeners might have heard me tell this, but the review title is, if you've never thought about anything ever, this book is for you.

I love this. Oh my God.

I don't know how much worse it can get. I mean, that's pretty bad. Maybe attacking my character. And the other day I was gonna update. Cause I said even at that time, this is like 12 or 13 years ago, I said, these reviews hurt, but they won't kill you. And I'm so much happier I put the book out. It led to such great things. It led to five years of keynote speeches. It's the foundation of my business, that book. So even though it is a little cringe to go back. Oh my gosh. When I did the revision in 2017, I had in earnestness quoted Donald Trump talking about money.

Oh my gosh.

Yeah, yeah, stuff that talk about cringe. Anyway, it's like, yes, those things sting. They really do. And the other day when I was going to update this whole concept of negative reviews, it made my stomach churn just to have to go to the one stars for all three books. It's no more comfortable. I would more regret not doing the thing at all.

Yeah. What it's reminding me of and it makes me laugh. And thank you for having the courage to share that. It reminds me of one of the things we talk about in the approval chapters is this idea of catering, which is it's very easy to, to cater to others expectations. And you and I both know Jenny, as authors, as speakers, if we tried to cater to every single person in the audience, we would have the worst books, we would have the worst speeches. I still remember I did a keynote a couple months ago and I received, they had the QR code for the survey at the end. And I remember I laughed out loud because one comment said this was two facts and figures based. It was like a TED talk. And then there was another comment going, this was not researched enough. I felt like it was more stories. I was like, well, which is it, right? Like it's too many facts and figures in research or not enough research, right? So it is pointless to play the unwinnable game in the spirit of trying to avoid social discomfort. People are going to people. There's absolutely no getting around that. And so of course make adjustments where it serves your overall growth. If there are patterns that come up over and over, then perk up your ears and listen, right? We're not saying that feedback's not valuable in some ways, but if we over engineer our lives and our behavior in the spirit of trying to create social harmony at all times, we're playing a game that can't be won.

I love people, grown people.

Unfortunately they do.

They sure do. I've had the same thing where I had one of my biggest speeches to a thousand people. Maybe there was 150 feedback surveys that came in and probably a hundred said, I love Jenny's demeanor, she's so relatable. And then one person said, so unprofessional, way too relaxed on stage, you know, and it's like, I'll remember both, but just the fact of quantity. Like many more people appreciate it than didn't. But there would have been no possible way for me to please both types. There just isn't.

And what I know of both of our work is that, and I think again, early on, I'm sure you and I both played this game of what do the people I serve, what do they want? Right? Let's try to give them what they want. But I know again, definitively on my side, and at least what I'm watching from your side, is when we settled into our way of being, when our personalities finally got a chance to shine in the spirit of our work, is when both of our Success went on the rise, right? Because performing has a cost. People can sniff it out. We actually do better. We are hired more, we are trusted more. When we bring all of that stuff to the table, not just the authenticity in the cute ways, but in the missteps, in the awkwardness, in the blunders, that's where authenticity lives. I feel like this conversation around authenticity, it's missing the fact that authenticity isn't all positive sometimes it's embracing the stuff that doesn't always feel so good. But we have to be able to play in both of those places.

And I can say I am definitely not immune to the pleasing mode or the conforming to what other people want. Like, it was only when I lost my biggest corporate client this summer, six months ago at the time of this recording that I dropped a lot of the song and dance that I had been doing to kind of like look good to companies. I always wanted to be hireable for speaking or licensing. And something about losing that long term, favorite, most abundant client. It just broke something in me where I stopped caring. I started a substack called Rolling In Doe d O h with a face palm. And I've been writing ever since. Twice a week, essays that only now I'm unpacking it with you in this moment are about all the cringe worthy mistakes, the embarrassments, the failures. Like, I finally just felt so fed up that so few people were talking about how hard it's been. The nitty gritty, not, oh, I had a dollar in my bank account and now I'm a gazillionaire. Not that story. The I had a dollar and I still do or now I have negative $100 and here's how I'm confronting it in the moment. And I just stopped caring what future companies who hadn't even hired me yet were going to think. Like, I just don't have the energy to do that anymore. So here we are. And the cringe, actually publishing the cringe. It's been the best received project I've ever done and it feels so good afterward because I'm like, each one, there's that transmutation or alchemy of I took what was a failure or something embarrassing and just airing it out and having other people respond. There's something very healing in that process.

First of all, rolling in the dough. Like I just have this Homer Simpson dough, you know, like in my head.

Exactly. Yeah.

Is the greatest name ever for a newsletter. And you know, to me what you're describing and I think the world just needs so much more of is maybe Jenny, you and I come up with a great name for this. Whatever the opposite of a highlight reel is. It's the real real. It's the real real that every single person, that person that we perceive from our seat to have that cool as a cucumber confidence. What we have heard for decades and it's certainly not new is successful entrepreneurs sharing their failures. People that talked about the hard stuff, their adversity. You know, that's not new. Where I think there's still room is the little everyday embarrassments, the little I feel awkward right now going into this meeting from somebody who is still on their trajectory. That's the stuff that I would like to see more of because again, you're already a billionaire and you had some adversity 10 years ago. Cool. Can't relate. But you're still building your speaking career and you're a first time author and this is making your stomach hurt and you feel like nobody's gonna like this. That's relatable, that's real. And that comes from being able to admit some of these emotions that have just for a long time been less popular to speak about.

Well, I love the RealReal. I think you just successfully named the new reel not to be confused with the secondhand clothing company. But the RealReal is so good. Even if there's a billionaire, we don't want to HEAR your story 10 years ago that you've said a million times. I, I want to hear when the billionaire was awkward fan personing out to someone they admired. Just yesterday, like you talked about Vanessa Van Edwards who's been on the show interviewing Guy Raz, asking Guy, how awkward are some of the founders? Like how are they really even though they're so successful? So I know we have to wrap up soon. I just very briefly, because I'll put one of your exercises in the show notes, could you just very briefly touch on the difference between redemption stories and contamination stories?

Yeah, absolutely. So this comes from Dan McAdams out of Northwestern University. He came up with this framing of the types of stories that we tell ourselves so quickly. The way our brains work, especially as it relates to emotions of discomfort, is our brains tend to focus on standout stories. So in a given day, all kinds of things can happen to us. But the ones that our brain tends to latch onto are the standout stories. The ones that we feel sort of define our day, our week, our experience. Now often when it comes to awkward or embarrassing situations, our brains again, as social creatures, latch onto those as standout stories. And what can become a danger is that those situations, if we don't evaluate them or unpack the story we tell ourselves, it can do something called contamination, Meaning that moment can contaminate us from taking the same chance in a future moment. For example, I raise my hand in a meeting. I am sharing the win of a teammate, and I brutally mispronounce their name. Horribly. This is someone I've worked with for a while. I should know better. That situation is so embarrassing. I'm loudly corrected. I am red head to toe, and I decide in that moment, subconsciously or consciously, I'm never raising my hand in a meeting again. That situation has contaminated future situations. It's preventing me now from raising my hand and essentially paralyzing me from taking those actions in the future. Versus a redemption story is actively looking for the gifts in the garbage. So after that meeting, let's say I'm doing what a lot of humans do. I'm replaying the situation in my head going, oh my gosh, Hannah, you're an insane idiot. I can't believe you said that. Actually pausing long enough to say, hey, you know what? That didn't feel good. But what is the gift in the garbage there? The gift could be, hey, you know, I don't normally raise my hand in that meeting. And I raised it. Now, granted, I wish that went differently, but I raised it, and that's worthy of celebration. It could be. The team was actually really kind and generous about the fact that I mispronounced it. I didn't get made fun of. It really made me feel like they had my back. Right. What is the gift in the garbage? But just know that our human wiring our brains are biased for negativity. That positive redemption story doesn't necessarily come naturally to us. We actually have to go pause for a moment following that awkward interaction and look for it. If we do, it feeds us positively to continue to take those risks in the future. But we have to slow down long enough to do that.

Brilliant summary. And just to highlight the importance of that, is that we do tell stories about the best of times and the worst of times. That is what our brain is primed to remember. So that's why these two distinctions is so important. Hannah, this was such a delight. Thank you for writing this book. It just made my week reading it and chatting with you. I'll put all the links to your work in the show notes, including where listeners can take the self consciousness scale. And is there anything else you want to say before we wrap up no.

Just I've been a fan of your work for a long time, Jenny, so thank you for keeping your own shooting of shots awkward or not. Thank you for continuing to do the work that you do and to your listeners. You know my mantra this year has been take the work seriously, but not yourself. Laugh at your own awkwardness. There's so much heaviness in the world. You can take your work seriously, but don't take yourself so seriously. You can do this.

I love it. Thank you so much Hannah. Big thanks for everybody here listening.

Thank.

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