Why Awkwardness Is Your Competitive Advantage in Content Creation with Henna Pryor

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Do you remember the most awkward moments of your life? One for me was definitely the day I was defending my master’s thesis. I was explaining a complex algorithm, when my advisor interrupted me and said, “Well…that’s not really how it works.”  In front of my classmates, other faculty, and a number of friends who showed up out of support.

As you can imagine, I was mortified – until recovered, finished the presentation, and said, If you have any questions, I’d be happy to answer them. Unless it’s about that one algorithm. They you can ask Dr. Bishop.” 

That got laughs, and I finished strong. I learned an important lesson that day: awkwardness will happen. It’s how you handle it that has a lasting effect. And that’s exactly what Dr. Henna Pryor is going to talk about with us today. She’s a keynote speaker, and her best-selling book, Good Awkward, came out in September with endorsements from people like NFL Quarterback Russell Wilson. 

Top Takeaways

  • We are living in a society that increasingly doesn’t need to use its “social skills” muscle. We don’t have to interact with as many people, and it’s making us feel worse. 
  • Awkward goes hand-in-hand with uncertainty. That means if you never want to feel awkward, you’ll never grow. 
  • In order to embrace uncertainty, and therefore awkwardness, we need to create more situations to “practice” than the current world gives us. 

Show Notes


Henna Pryor: I do think that when we use the word “awkward” as an identity, it is a limiting belief in a box. Because here’s the truth. Here’s what bubbled up in the research. There is no such thing as a factually awkward person.

I want all of your listeners to let that soak in. There is no such thing as a factually awkward person. It is subjective. The emotion of awkwardness is subjective and are using it as a trait to describe whether it’s ourselves or someone else is subjective. That means it’s a matter of opinion. It is up to us to deem someone else awkward or it is up to us to do ourselves so. But there is no such thing as a factually awkward person.

Joe Casabona: Do you remember the most awkward moments in your life? One for me was definitely the day I was defending my master’s thesis. I was explaining a complex algorithm called the Bounding Box algorithm when my advisor interrupted me and said, “Well, that’s not really how it works,” in front of my classmates, other faculty, and a number of friends who showed up out of support.

As you can imagine, I was mortified until I recovered, finished the presentation, and said, “If you have any questions, I’d be happy to answer them, unless it’s about the bounding box algorithm, then you can ask Dr. Bishop.” That got laughs and I finished strong.

I learned an important lesson that day. Awkward will happen. It’s how you handle the awkward that has the lasting effect. And that’s exactly what Dr. Henna Pryor is going to talk to us about today. She’s a keynote speaker and her bestselling book, Good Awkward, came out in September with endorsements from people like NFL quarterback Russell Wilson.

I’m so excited for you to hear this episode because everybody feels awkward at some point. And Dr. Henna Pryor tells us that we need to lean into it.

Look for these top takeaways. We are living in a society that is increasingly losing its social skills muscle. We don’t have to interact with as many people and it’s making us feel worse.

Look for the fact that awkward goes hand in hand with uncertainty. That means that if you never want to feel awkward, you’ll never grow. And in order to embrace uncertainty and therefore awkwardness, we need to create more situations to practice than the current world gives us. So make sure to put yourself in situations where it’s uncertain, where you might feel awkward.

This is a great interview and I know you will enjoy it. We talk about a bunch of things. And of course, if you want to get a copy of Henna’s book, Good Awkward, which I recommend, I am reading it now, you can head over to howibuilt.it/338 to get that and all of the show notes.

But for now, let’s get into the intro and then the interview.

[00:03:19] <music>

Intro: Hey everybody, and welcome to How I Built It, the podcast that helps busy solopreneurs and creators grow their business without spending too much time on it. I’m your host Joe Casabona, and each week I bring you interviews and case studies on how to build a better business through smarter processes, time management, and effective content creation. It’s like getting free coaching calls from successful solopreneurs.

By the end of each episode, you’ll have one to three takeaways you can implement today to stop spending time in your business and more time on your business or with your friends, your family, reading, or however you choose to spend your free time.

[00:04:08] <music>

Joe Casabona: All right, I’m here with Henna Pryor, author of the book Good Awkward. Really excited to talk about this because I tell people I have the ability to shake off awkward. And you wrote a whole book about this. So, Henna, thanks for joining us today.

Henna Pryor: Thank you for having me. I love that this resonates with you out of the gate. We’re going to have a ton to talk about it.

Joe Casabona: Let’s dive right into it. What do you mean by awkward?

Henna Pryor: Hmm. So my working definition of the word “awkward” is awkwardness is the emotion that we feel when for a moment our true self, that person that we believe ourselves to be is in a gap between the person who is on display.

So simply said, who we believe we are momentarily feels different than who they see. Our internal identity doesn’t match their external reality. And when we’re finding ourselves in that gap space, we feel the emotion of awkwardness. It is an emotion of discomfort, and it is a social emotion, meaning we don’t tend to feel it when we’re by ourselves.

So if we’ve mispronounced someone’s name or we put our foot in our mouth but no one was there to hear it, we don’t tend to experience the emotion of awkwardness. It is a social emotion, so in order to feel it, it requires another. But we feel it when we’re in that space between our two selves.

Joe Casabona: Oh, that’s really interesting. So I guess I’ll ask for a distinction here because awkward could be like the embarrassment, right? But it could also be, you know, I’m feeling a little nervous but I’m trying to project this, like, big bravado, like John Wayne man kind of thing. Like, I can feel awkward then as well, right?

Henna Pryor: Sure. There’s lots of different ways that can show up. Ultimately, when we think about this emotion, it has to do with expectations, right? What does somebody else expect of us? I think another important way to approach this is some people view awkwardness as a temporary state.

Embarrassment is one way we can think of awkwardness as a temporary state. I said something cringy or I experienced something that was embarrassing, but it’s fleeting, it’s transient, it goes away, it passes. Sometimes we get stuck on it for a few minutes, sometimes for a few hours, but it eventually passes.

Other people will use the term awkward as a trait. I am socially awkward. I am someone who is awkward all the time. So it really depends how we use the term and the language. Do we use it as an emotion or do we use it as an identity? And when we use it as an identity, it becomes a bit prickly and dangerous because it can create behaviors in us that either stop us from doing what we want to do or put on sort of what you started to describe a performative version, a bravado version to try to manage that emotion.

Joe Casabona: Yeah, that’s super interesting. The fleeting, like transient, everybody feels that, right?

Henna Pryor: Yeah.

Joe Casabona: Like, they’ll be that thing that you did like ten years ago, and it will just creep into your mind and you’ll feel that guttural feeling for a minute. But the trait, that is even more interesting to me. Because I think as we get online more, like you see this… I don’t want to say undeserved confidence but I don’t know the better word, in like the Gen Z crowd?

Henna Pryor: Yeah.

Joe Casabona: You know? Not to like other the Gen Z crowd. I’m an elder millennial.

Henna Pryor: Me too.

Joe Casabona: But I think you see that a little more. And maybe as people are online more and they’re on video more, you get this sense that like you deserve to be. I’m wondering how much of that is like this awkward feeling like they see celebrities act that way and so they feel they need to act that way.

Henna Pryor: I’m actually really excited to talk about this because I’ve not had a chance to talk about it from this angle, but I think it’s an important one. What I feel is our biggest danger zone right now as it relates to this topic is we are living in a society that is losing our strength in social musculature.

So explain what I mean by this. We do not have to have the social interactions anymore that invite in the moment awkwardness. You know, when we call or when we want to order our tacos, we don’t have to call the restaurant. We order on DoorDash, we order on ToastTab.

When we are at our friend’s house picking them up, we don’t have to ring the doorbell. We just text “here” from the driveway. Elder Millennials remember when we wanted to call our friends, we had to chitchat with their parents for a couple seconds before, you know… These things are no longer part of the fabric of our social interactions.

And what’s happened as a result is our social muscles weaken the same way that our physical muscles do. And increasingly, again, beyond society’s things, a lot of us are working from home, a lot of us just don’t have to have these interactions.

So what we find is that when Millennial Gen Z or frankly anyone is now faced with these social interactions, it becomes difficult. And when you have these online versions, it is safe, right? There may be an inherent awkwardness that they feel, but they don’t have to handle it in the moment. They get to sort of deal with people’s reactions over time, which is not real life, right? Not real life.

Joe Casabona: Right.

Henna Pryor: Most people don’t work in environments where they’re completely by themselves. They don’t live in environments where they’re completely by themselves. So losing the social musculature of handling in-the-moment interactions that potentially go sideways is a real danger and something we need to be intentional about, and part of, you know, the thesis of the book.

Joe Casabona: That’s really interesting. Because I had that experience very recently with a… I had ordered food from a local establishment, did it online, and I called to check up on it and the person I spoke to on the other end was like fireable offense rude.

Henna Pryor: Oh no.

Joe Casabona: They got fired because I called customer service and they listened back to the recording and-

Henna Pryor: Yeah.

Joe Casabona: Yeah. And I’m just like, who behaves like that? And the people who behave like that are the people who can say things like that online without consequence, more or less. It was just a very jarring experience. I didn’t get a hello, I just got a bunch of expletives. It was wild.

Henna Pryor: Yeah. So that to me is one side of the pendulum, right, where someone is behaving in a way that is jarring. The other side is people who, you know, I playfully say they forget how to people. Right?

Joe Casabona: Yeah.

Henna Pryor: Like they don’t even know what to say. And what that really speaks to is a lack of relational practice. When we’re not around people all the time, we don’t have those little opportunities to practice reading someone’s gestures, listening to the tone of their voice for impatience, frustration, and dissatisfaction.

When we don’t have chances to practice in the little moments, day to day, which increasingly we don’t, then it becomes very difficult to manage a difficult conversation and unhappy interaction because we don’t know how to read people the same way and our relational skills start to suffer. So I’m not surprised that this is showing up in those places.

Joe Casabona: Yeah, absolutely. I consider myself an extrovert. Everybody would consider me an extrovert. The first conference I went to kind of post-pandemic, my first in-person conference, there was a little bit of that. I was like, “Oh man, it’s been a while since I’ve just walked up to a stranger and talked to them.” Like, “What do we talk about?”

It took me like maybe an hour to get my sea legs, and after that I was good. But yeah, it’s just like you said. Like if you don’t work out right, you lose those muscles. If you don’t run, then you… I learned this the hard way. If you don’t train for one half marathon, and then you can just keep running them without training.

Henna Pryor: Exactly right.

Joe Casabona: Running for me is generous term. Participating in a half marathon.

Henna Pryor: Fast walking.

Joe Casabona: Yeah, exactly. Doing it in under 16 minutes per mile. So I think you’re absolutely right. Now, thinking about this, because I would say that the experience I had was full-on just obnoxious interaction. I was calling to see like, Hey, where’s my kids’ food? And they didn’t even let me say that.

Henna Pryor: Sure.

Joe Casabona: I think that some people will hide… Maybe I’m like strawmanning here. But I think there are people who will hide behind the guise of, “Oh, I’m awkward” or “Oh, I didn’t know, but they’re actually being obnoxious or mean or some other thing.

Henna Pryor: Sure.

Joe Casabona: How do we kind of differentiate those two things?

Henna Pryor: Yeah, it’s a great question. I do think that when we use the word “awkward” as an identity, it is a limiting belief in a box. Because here’s the truth. Here’s what bubbled up in the research. There is no such thing as a factually awkward person.

I want all of your listeners to let that soak in. There is no such thing as a factually awkward person. It is subjective. The emotion of awkwardness is subjective and are using it as a trait to describe whether it’s ourselves or someone else is subjective. That means it’s a matter of opinion. It is up to us to deem someone else awkward or it is up to us to deem ourselves so. But there is no such thing as a factually awkward person.

So if you are using that term to describe yourself as a trait, as a statement of fact, I need, first of all, to start from that place of you are using that term as a crutch, as a safety net, as a box, as a limiting belief. But there is no such thing.

Awkwardness is also not the same as ineptitude. So in the book I use the example: I would not hire an inept anesthesiologist or an inept tax accountant, but I’d be perfectly fine hiring an awkward one. Right? So this is not ineptitude, nor is it an excuse to be on bad behavior and then use that trait as a crutch for the way you’re showing up socially. Because you are unkind or unable to manage your language in a social setting, unfortunately does not make you awkward, that just makes you obnoxious.

Awkwardness actually lives in uncertainty. So if you’re saying these words with some intention and some knowledge behind it, that’s not uncertain. You know what you’re doing. You’re just making a choice about the way you’re showing up socially. And you cannot use awkwardness as a crutch. It’s not correct.

Joe Casabona: Yeah, that’s really interesting. And awkwardness is not the only place that shows up, right?

Henna Pryor: Right.

Joe Casabona: I watched a woman let her kid just, like, wreck the aisle in an Apple Store or those shelves, and she’s like, “Oh, he has ADHD.” And then she just walked away from the mess. And I’m like, “There’s a lot of things wrong with that statement.”

Henna Pryor: Sure.

Joe Casabona: One is that ADHD doesn’t mean you can just let your kid do whatever they want. That’s not what that means. Also, clean up after your kid. Or like my friend would always be a jerk when he was drunk. He’d be like, “Oh, I was just drunk,” until we replaced his beer with nonalcoholic beer one time, and he still behaved that way. So he just used that as the excuse to be mean.

So I think, like you said, I want to highlight that again, there’s no such thing as a factually awkward person, and awkward lives in uncertainty. I think those are the two big takeaways here.

Henna Pryor: Right. So in the example you just gave about the mom, you know, in the aisle with the toddler who is kind of running amok, I think there’s, you know, potentially one of two things at play is that she feels so embarrassed or cringing or awkward about it that it creates inaction. Which awkwardness can do that, right? I didn’t expect my toddler to go nuts here and I feel so awkward about it that I don’t know what to do. So I’m doing nothing.

Or it’s a choice, right? It’s a choice. But that is the exploration. And without having a conversation with that person, there’s no way of me knowing which place it’s coming from. But some people, the awkwardness paralyzes their ability to take any action step. And if that is the case, you know, she’s just trying to cope in the moment, and that awkwardness is creating an inability, a physical inability to move forward with any sort of action step.

Joe Casabona: Yeah. Oh, that’s really interesting. That’s a nicer way to think about it than I’ve been thinking about it for the last like five years.

Henna Pryor: Yeah. You’re like, “That idiot.”

Joe Casabona: I know. I guess it’s like eight years I didn’t have kids. I tried very hard not to judge people with kids when I didn’t have kids, but I was like, “Someone should clean this up.”

Henna Pryor: Right. Right.

Joe Casabona: But that’s really interesting. If someone feels awkward, that can lead to inaction. That’s a really good thing to consider when you’re out in the world.

This is a show for solo producers and creators. So as we think about awkwardness and awkward being a limiting belief, I know that a question I get is, how do you become comfortable when you’re recording a podcast? How do you become comfortable in front of the microphone or in front of the camera?

And for me, honestly, it was that I did Drama Club from like… Shout out to Miss McCullough, now Sister Mary. In second grade she got me involved in drama club. So I’ve always kind of been in a performative state, so I didn’t have a lot of trouble getting in front of the microphone. How much do you think the limiting belief of awkwardness contributes to maybe the lack of wanting to create the content that you should be creating?

Henna Pryor: Yeah, I think significantly, because ultimately, again, awkwardness is a social emotion. So if we’re creating content online or if we’re, you know, putting out assertions videos in that sort of format and consumption, what we’re essentially scanning for as human beings is approval. We are social creatures. We are still hardwired for wanting to belong, for social acceptance. That will not go away.

And awkwardness is that tension that we feel when we’re not sure, right? We’re not sure how something is going to be received or we did take that step and we put it out there and it didn’t land the way we thought it would, right? Our expectations weren’t met.

And awkwardness, you know, it exists in that tension space, but it also exists when our expectations go sideways. You know, we thought it was going to go like this, nobody responded, nobody engaged, nobody liked it. And all of a sudden we’re like, “Is it me? Is it me? Did I screw something up?”

One of the key awarenesses about learning how to embrace awkwardness rather than to avoid it is that we can try until we’re blue in the face, but we cannot predict other people’s behavior. So learning how to sit in that tension and that messy middle of uncertainty, of awkwardness, of discomfort is key to continuing to put yourself out there.

You will not continue to make content if every time the response you get or the approval that you get is your only metric of success. You have to learn how to live in that gray area of I’m doing this for the purposes of putting out the work, you know, doing the process, putting out the effort. Outcome-based thinking will freeze you at the edge of taking those risks every single time. You’re never going to be able to do that stuff on a consistent basis if you’re always thinking that way.

Joe Casabona: Wow. That’s a really great point. I want to push back on asking about shouldn’t we try to shake being awkward. But we do need to take a quick break for our sponsors.


Joe Casabona: And we’re back. Okay, so, Henna, you said we should embrace awkwardness. But, I mean, you know, you look at the movies, you look at TV shows, Zach Morris and Zach… that’s a really dated reference. But Zach Moore is not super smooth. AC Slater was always super smooth. And then the people that we see online too, and our favorite creators are usually very good at what they do. I mean, shouldn’t we try to get rid of the trait of awkwardness.

Henna Pryor: I love the Saved by the Bell throwback by the way.

Joe Casabona: Thank you.

Henna Pryor: I feel like, you know, you people need to not look at it as I’m either a Zack Morris or a screech right there? There’s shades of gray in between. I do not agree that we need to shake off awkwardness and I’ll tell you why. When we try to eliminate awkwardness again, first thing first, that’s eliminating uncertainty.

So you might be able to keep yourself out of certain situations that invite awkwardness, but you cannot and will not avoid them all. You are not going to get through this life without tripping on a crack in the sidewalk. You are not going to get through this life without accidentally mispronouncing someone’s name or getting it wrong. You will not.

So for me, it’s less about shaking it off and understanding that every time you are trying to grow in your entrepreneurial journey, in your content creation journey, any time you are trying to play a slightly bigger growth edge, you are inviting the potential for that awkwardness to come back.

So if your goal is to eliminate it, you will stay small, you will stay in that safe zone, you will stay in that box. But if you understand that it comes with the territory of taking bigger chances… You know, you and I both know well that the content creation game today is about standing out. It is noisy and standing out requires taking risks. And taking risks means sometimes it’s not going to land the way you want it to. But you have to take those risks if you’re going to stand out in this noisy marketplace.

The second thing is, is those people that you’re talking about, these smooth content creators, guess what, they definitely have rerecorded, rewritten more times than you can count and… you know, I do a lot of keynotes speaking with corporate teams as well. And one of the things we talk about with executive presence is most people think of executive presence and confidence as, you know, these people just have it.

What you don’t realize is they’ve been practicing for years. They’ve been doing exactly what you did, which is, you know, drama club at a young age or maybe even if they started later in life. Just repetitions. I imagine you think back to your first podcast and you’re like, “Mm. Eeh. Not so great.”

Joe Casabona: You could still hear that. You could go listen.

Henna Pryor: Yeah. But it’s repetitions, right?

Joe Casabona: Yeah.

Henna Pryor: So what you’re seeing when you see these smooth content creators isn’t their first at bat. And often, you know, we all know the expression, we compare our behind-the-scenes to other people’s highlight reel. They had to do this a bunch of times to appear smooth, flawless, confident.

And what came out in the research, which I love, is that your favorite smooth entrepreneurs, content creators, the one that you think they are so confident, guess what? They don’t experience awkwardness less than you do. They feel exactly the same. And as often as you do, they’ve just learned how to bounce back from it and lean into it very quickly. They don’t try to skirt it. They don’t try to avoid it. Because guess what? The avoidance of awkwardness increases awkwardness, so they just move through.

Joe Casabona: The avoidance of awkwardness increases awkwardness. I love that. And you think about all of these other areas where people have internalized that this makes sense, right? In most of the first season of this show, we talked about how we see the Olympic gold medalist in their gold medal performance. What they don’t see is that like since three years old, they were sacrificing and practicing to get to where they are today. We know that Alex Rodriguez or Aaron Judge or Ronald Acuña Jr…. I love baseball.

Henna Pryor: I can tell.

Joe Casabona: Some of the best baseball players in the world they go through slumps. You know, Alex Rodriguez was famously very insecure despite being the best baseball player four years in a row. But he bounced back and he overcame that.

Awkwardness is another thing that you can overcome and embrace because you’re always going to be better. Like you said, you’re always going to be growing or you should always be growing. And so you’re always going to be in awkward situations because of that.

Henna Pryor: Yeah. I love the comparison to athletics. So one of my partnerships is with an organization called Limitless Minds that was co-founded by Russell Wilson, his brother Harry, DJ Eidson, and his late mentor conditioning coach, Trevor Moawad. So people who know athletics who often have heard of Trevor Moawad. He worked closely with Russell and lots of other collegiate teams. And I had a chance to speak with Trevor several times.

And what Trevor normalized was, you know, in athletics, the top athletes you know not only put in the repetitions, but they work preemptively and proactively on their mental skills. They work on these areas where mentally and in the case of awkwardness, socially, they feel a bit unsteady, they feel a bit hesitant, a bit ill-prepared. And they don’t wait until the moments arise to practice these mental skills. They go seek them out.

So one of the things that I’m very passionate about as it relates to our social fitness, which is what we’re talking about, which is mental fitness in the social spheres as it relates to other people is intentionality. If we’re constantly in the grocery store line and looking at our phone and never look up to lock eyes with someone, missed opportunity to practice.

The other day my husband was ordering tacos for the family and Toast Tab was down and he was like, “Where are we getting dinner instead?” I was like, “Instead? No, I want tacos. We’re going to call the restaurant.” But when we constantly skirt these micro opportunities for social muscle building, then we will struggle at the big game, right? So intentionality is so key. Conditioning our minds for this is so key.

Joe Casabona: Yeah, we don’t always need to go for our PR, our personal record. We can do conditioning. Right?

Henna Pryor: Right.

Joe Casabona: Fun fact about DoorDash and Uber Eats at this point is I don’t have either app.

Henna Pryor: Wow.

Joe Casabona: I deleted my accounts. I don’t know if you’ve experienced this, but DoorDash in this area is not good, in my experience.

Henna Pryor: It wasn’t in my area, but now it is, which is dangerous because money flying away.

Joe Casabona: Yeah. So I was just like, “You know what? Like if we want something, I’m either going to go get it or I’m going to order from the pizza joint right down the street or whatever.”

Henna Pryor: I love it.

Joe Casabona: People say I’m an old soul. I definitely prefer to have the… Despite being technical, I always want to talk to a person. I just know that I’ll be able to communicate my needs better than telling a machine and getting some rote response back.

Henna Pryor: Yeah. But Joe, if I can maybe make a leap of a connection. The fact that you do this with regularity makes your ability to be a great podcast host easier, makes your ability to ask for things that you really want at your core easier because you are keeping that muscle conditioned.

You know, people are like, “I don’t do this, do I?” And then I’ll ask them, “Do you ever get on an elevator and press the closed door button because you don’t want to have to deal with a small talk of somebody else getting on and they’re like, Uhm-

Joe Casabona: Wow.

Henna Pryor: How many of us do that?

Joe Casabona: Oh my gosh.

Henna Pryor: Right? Even extroverts do this.

Joe Casabona: That’s so funny. I never do that.

Henna Pryor: I don’t either. But actually, it’s intentional, right? I can’t tell you how many people and I… I want to circle back to something you said at the beginning. People think, “Henna, you wrote a book called Good Awkward. Is this for introverts?” No.

Joe, I, like you, am 100% extrovert. I’m not an introvert. Introverts do tend to experience awkwardness more acutely. But what I have observed, just like you, is post-pandemic, is social muscle can atrophy. And this is becoming the society that we live in. So it’s for everyone.

And if you’ve ever hammered an elevator door shut, this is for you too. If you’ve ever looked at your phone in the grocery store line to try to avoid small talk, this is for you too, right? This is all of us these days.

Joe Casabona: Yeah. Wow. That’s amazing. And yes, like you said, I’m not without awkward. Actually, for subscribers, you’ll be able to hear Henna and I tell a couple of our maybe best or worst awkward stories.

Henna Pryor: Both end.

Joe Casabona: Both end. Yes. So if you want to get that conversation as well as this entire episode ad-free, you can head over to howibuilt.it/join. Or if you’re listening in Apple Podcasts, just press the subscribe button and you can get those conversations.

By the way, I’m always the guy who makes the comments in the quiet elevator, like, Oh, we’re on the local or whatever. I’m that. I was like born a dad. I have felt, maybe since getting married, maybe since having kids more generally confident and comfortable in who I am. Is this something that kind of changes with age? Are, generally speaking, younger people more awkward because they’re less certain?

Henna Pryor: Interesting question. So yes and no. So here’s some interesting research. Kids don’t feel awkward because they haven’t yet learned they should feel that way. So self-consciousness is the category of emotion that awkwardness sits in. It’s a self-conscious emotion, meaning we are looking for who we are through the lens of who other people see. So we’re scanning for other people’s opinion of us to sort of define who we are.

Research from the Association of Psychological Science found that around age eight or nine that starts to kick up. So you’ll notice if you’ve got children or nieces or nephews or neighbors in your life that are younger than eight, they don’t really care that much, right? They’re in the kitchen, they’re dancing, they’re swinging their hips are like, “I don’t care. You’re watching me, so?” They just don’t care.

And it’s around eight or nine that we start to notice other people are watching us, making an opinion of us. We start to scan for what are the social norms of this classroom, of this family unit, of this group. So we start to feel it around then.

And then interestingly, and chapter five in the book is all about this approval kind of tendency is, yeah, as we start to grow, as we start to hit new phases in our life, new school, new college, new job, promotion at the job, every inflection point that kind of ding ding siren for approval kicks up again, which is why they tend to feel awkward.

But then, as you said, we get to this point later in life and there’s a phenomenon called the Spotlight effect—we think people are paying much closer attention to us than they actually are, they rarely are. But there’s an old adage that says in your 20s and 30s, we care a lot about what other people think of us. And in your 40s and 50s, you stop caring what other people think about you.

But then in your 60s and 70s, you realize they were never thinking about you that hard in the first place. So you’re right. As life goes on, that starts to change because we recognize that that spotlight that we thought was on us just is either nonexistent or not nearly as bright as we thought it was in those earlier years.

Joe Casabona: That’s really interesting. I always say people always like to think they’re the star of the movie. So like-

Henna Pryor: Main character energy. Is that what they are?

Joe Casabona: Yeah, main character energy. Yes. I love that. And that’s actually really interesting, right? Because I have three kids, six, three and two, and so six going up to 16 really. My therapist has told me like at six, seven you think the world revolves around you, but like in a very different way. Like you think everything is happening because of you and not people are kind of scrutinizing you, which is what the spotlight effect sounds more like.

Henna Pryor: Mm-hmm. Yeah. And it’s, you know, after that phase of, you know, nine, ten years old… So I’ve got a 13 and 11 year old. They’re in the eighth and sixth grade, both in middle school. Now, let me tell you, this is the height of everyone is watching, everyone is staring. Social belonging means everything. Right? It’s natural. It’s developmentally appropriate.

But we really start to look for who we are through the lens of other people’s expectations of us, not because of this is who we really are at our core, but who do other people see. And then more importantly, do they like who they see? So everything at this age feels incredibly awkward.

And, you know, as a parent, I’ll be honest, it’s tough to watch, especially as someone who’s researched this and wrote a book about. But it’s also the most natural sort of evolution that there is. It’s just helping them cope with those moments as often as possible.

Joe Casabona: Yeah, that’s really interesting. If I wasn’t already going to get your book before this, I’m definitely going to get it now. Good Awkward out now. Because I want to make sure that I handle that appropriately.

You know, again, awkward is like I feel it and I feel like I can shake it off better than a lot of people. But like my daughter, for example, like it was like school sports day, we are in Philly Sports Country, I’m a New York sports fan. So I sent my daughter to school in a Yankee shirt and a Philly shirt. And she was like-

Henna Pryor: How dare you?

Joe Casabona: I know. She was like, “A couple of boys made fun of me.” And I’m like, “Just tell them 27 rings.” But she was like, I maybe wasn’t as empathetic to the fact that her peers were like other… not othering her but like, “Why do you like this team? This team is not the team you’re supposed to like.”

Henna Pryor: Right. Right. It’s a natural behavior for that age. But I think we’re you know… I smile every time you use the term “shake it off” because, you know, the way I would describe your equivalent of shake it off is you don’t let the emotion hook you is what you’re saying, in other words. Like you experience it, you feel it, you’re human. You know, as long as you have healthy brain function, you’re going to experience the emotion of awkwardness.

But what you’re saying is, I don’t let that emotion sink its hooks into me and prevent me from moving forward quickly, from taking that chance the next time. In other words, your comeback rate is fast and that’s what high performers do. The people who we see as confident entrepreneurs, content creators, you know, top people in business, celebrities, when we see people and they’re like, gosh, they’re just so confident, it’s not because they’ve learned to eliminate awkwardness. I assure you they have not. Their comeback rate is lightning-fast.

You know, I opened the book with a story about Jennifer Lawrence and how she tripped over her dress trying to go collect her Oscar. Do you remember that?

Joe Casabona: Yes.

Henna Pryor: And she rather than being mortified, which she was, there’s interviews after the fact where she was like, “Oh, my God, can you believe this?” But she got up there and she said, “You guys are just standing up and clapping for me because I fell, and that’s really embarrassing.” But she just she owned it, so she was able to come back from it. She became more endearing because of it and we moved on.

It’s not that she didn’t feel mortified. It’s not that she didn’t feel embarrassed. Her comeback rate was just very fast. And whether she knew it at the time or not, that had been something she’d been working on through her acting training, some improv training, things like that that you can do to develop the muscle to handle those moments in real-time.

Joe Casabona: I love that. And this is the perfect point to move to the big question, How can we embrace awkward, right? Because like the self-deprecating thing that works really well for me too, right? If I feel awkward, I definitely just kind of like, hey, I’m laughing with you. Let’s move on real quick sort of thing.

Henna Pryor: Yes. Yeah. So that’s one way. So, you know, in chapter seven of the book, it’s all on humor and the appropriate use of humor and awkwardness in those moments. So there are some rules, right?

So self-deprecation works beautifully as long as you are doing it about something that doesn’t speak directly to your competence. So sometimes, again, people worry if I express my awkward edges or if I appear awkward, will I appear inept or incompetent or incapable? And I always try to carve out that there is a difference.

Joe, if we know you as someone who researches and prepares for his podcast guess, who generally does good work and you say the wrong thing right now, believe it or not, there’s a phenomenon in psychology called the pratfall effect where the occasional blunder actually makes you more likable because it knocks you off of this golden pedestal that we put you on of being perfect all the time.

So it is okay to put your foot in your mouth, to stick your toe in it, and then have a moment of self-deprecating. “Oh, cringe. I can’t believe I said that.” Or “Oh, that was awkward, right?” A little bit of self-deprecation goes a long way as long as you’re not self-deprecating about your skill set. Like, I’m the worst podcaster there ever is. And then like, ooh, that doesn’t quite feel funny. That feels like, What am I doing on this podcast?

Joe Casabona: Right, Right.

Henna Pryor: So two different things. The other two kind of main components which we can certainly break down there’s… step one is self-awareness. What are the stories you tell yourself about awkwardness? Are they all contamination stories? Which means, you know, when I have an awkward moment, do I let it contaminate the future? Do I think to myself, “Oh, my God, that was so embarrassing. I’m never going to put myself in that situation again. I’m never going to try to give a presentation again for fear of saying someone’s name wrong. I’m not going to go on a podcast for fear of how I’ll sound.”

Does it create inaction or can you tell yourself a redemption story? “You know, I went on that podcast with Joe. I said this thing I wish I didn’t. But you know what? I’m going to look for… I like to call it the gifts in the garbage.” Right? Didn’t feel great. Awkwardness is an emotion of discomfort, but I put myself out there. I tried something, I didn’t get it right, but there’s a learning in it. So what are the stories we’re telling ourselves?

Second story that I think is really important, and I’ll pause here before I give you sort of step two is I love exploring people’s relationship with vicarious embarrassment. So as it relates to our own awkwardness, it’s not just how awkward do I feel myself, but how awkward or embarrassed do I tend to feel not just for other people, but with other people.

So, Joe, you may tell me a story about something you did, and not only am I like, “Ooh, poor Joe, that sounds embarrassing.” But some of us are so high on a certain type of empathy that we will literally take that on with another person. I’m like, “Oh my God, Joe, did you really?” Right? I’m beyond inconsolable. And that’s not even my situation. That was your situation.

But some of us that are very high on this particular form of empathy really struggle to manage our own awkwardness and embarrassment because we tend to feel that someone else is going to feel that way about us as well. And that’s not always it’s not always true. So examining those things is a great starting point.

Joe Casabona: That’s really interesting. It’s funny you mention that because I think like… again, I think I’m okay with my own awkwardness. I can’t watch Meet the Parents or like, you know, the episode of The Office. Scott talks-

Henna Pryor: Or Diversity Day.

Joe Casabona: Yeah, yeah. I really feel that. And it’s not even enjoyable for me to watch.

Henna Pryor: Joe, I love that you brought this up because this is a perfect test. The genre of comedy that you’re talking about actually has a name. It’s called cringe comedy. It has a name. It’s called cringe comedy. So The Office, The 40-Year-Old Virgin, Borat, America’s Funniest Home Videos, these are all designed to make us feel awkward and cringe because of other people’s social blunders. And some of us love them. We watch, we laugh, are hilarious and other people that are high on that particular empathy cannot. They’re like, “This is ruining my day. I feel it up and down my body.” So it sounds like, you know, you’ve got a little bit of that in you.

Joe Casabona: Yeah, definitely. I’ll tell that Office story more in the pro show. But yeah, that’s really interesting because I do think I have like the high… you know, I cried a lot of things and my daughter was like, Why are you crying? And I’m like, I just feel… I’m Italian, right? We feel a lot of things. So that’s really interesting. Okay, so we’ve got the humor, We’ve got self-awareness. What’s next?

Henna Pryor: The last step, which we’ve alluded to throughout the show but I think it’s just important to put a very clear spotlight on it, is conditioning. Repetition and rehearsal. Again, we live in a world that does not create these happenstance opportunities, so we need to over-index on creating opportunities to strengthen our social muscle in order to tolerate awkwardness when it inevitably arises.

This could be in, you know, physical situations, right? Like stay off your phone when you’re in the grocery store line or strike up a conversation with someone in a coffee shop or correct the server when they brought your order wrong. This can be little things like that. It can also mean intentionally creating spaces in your own communities with people you know to share missteps, blunders, embarrassing moments.

So I work, again, a lot with corporate teams. I will encourage them to do things at the beginning of a meeting, share cracked egg stories, meaning every member of the team has to share something that was woefully sideways that didn’t work out, or a bad idea. Brainstorm, meaning every team member presents an idea that is frankly unrealistic. It’s not actually going to work out. But what it actually accomplishes is it reduces people’s wall, it brings that guard down so that the ideas and the stories and the conversation that follows are more generative, more innovative, more creative.

So there’s all these benefits, there’s all these upsides to creating spaces where we normalize this conversation. But the world is not handing them to us anymore. We have to actually put ourselves intentionally in these situations in order to keep these muscles strong.

Joe Casabona: I love that. So it all starts with something I’ve been telling my kids forever. When you’re walking in public, just don’t have your phone and your device. My kids don’t have phones yet, but I always tend to point out, look, this person’s about to walk into a wall because they’re staring straight down at their phone. So just be more in the world. I love that.

I love that idea. Brainstorming, too. I always say, like when I’m trying to brainstorm with people and they’re like, I don’t know. And I’m like, There are no bad ideas in brainstorming. Just like, say whatever you’re thinking right now. And we write it down and maybe we do nothing with it, but it’s out there. So I love it.

Henna Pryor: Yeah. I think the fear is what you talked about before, which is, you know, will I be seen as inept? And again, if you’re brand new to your job or if you’re brand new to entrepreneurship, maybe don’t share all your bad ideas in your first few pieces of content. Right?

Joe Casabona: Right.

Henna Pryor: So once you built up a little bit of that capital for competence, have at it, right? If you’re brand new, be more thoughtful. There are some rules. But generally, people want to see your cracked edges. We appreciate it. It’s humanizing and it’s helpful.

Joe Casabona: Yeah. You mentioned the pratfall effect before and I’ve never heard it called that, but it reminds me of like… And I’m not going to condone this at all, but I know people who have done it. Like, if you maybe had a drink at the bar and you’re driving home after that and you drive like a little bit too perfectly, I’ve been told that that’s a signal by police. Like if you’re going the exact speed limit, like this person’s driving a little bit too perfectly, what are they hiding?

So I think that’s really interesting. It’s like the same thing, like this person presents themself to perfectly like it’s a little bit unnatural is maybe how I think about it.

Henna Pryor: I think it’s also just a shift for entrepreneurs and creators. You know, we’re no longer interested in this sage on the stage. You know, we’re interested in a guide on the side. Are they next to us? Are they with me or are they up there feeling like they’re at this unattainable place that maybe I could get to or maybe not?

Generally, wisdom has been that we like to follow people who are ahead of us, but just by a few steps, right?

Joe Casabona: Right.

Henna Pryor: When they’re so far ahead of us or they’re so flawless in their execution, it makes us feel like it’s out of reach.

Joe Casabona: Right. I’ll never get there.

Henna Pryor: All of that. Again, the occasional blunder just level-sets the playing field and makes us, in fact, like that person more. It increases their warmth. It increases their relatability.

I’m not suggesting we engineer it and, you know, purposely dump coffee on our lap in the middle of a podcast. But if you call me Hannah and then correct it to Henna, guess what? You’re real, dude. You know, we could edit it out, but I’m going to go ahead and suggest we don’t, right, if something like that happens because there’s beauty within it when we have those moments of humanity.

Joe Casabona: Yes. Now, I’m trying to think if I did that. I think I did that in the pre-show.

Henna Pryor: You didn’t.

Joe Casabona: Not on tape at least. You know why? It’s because I taught in a classroom for years. So, like, I’ve spent many years mispronouncing all of my students’ names. So I’m like now I know how to pronounce most names at least.

Or fun tip. Like, you can also check like LinkedIn and see people add on their pronunciation on LinkedIn or something else. Right? There are places now. Anyway. But I mean, I don’t want to undercut your point, Henna, that it’s okay to mispronounce people’s names sometimes, right?

Henna Pryor: Or whatever.

Joe Casabona: Yeah. Or whatever it is, right? This has been great. I’m going to ask you one more question in the pro show that’s probably the maybe juiciest point. I’m going to ask you in the pro show if you think AR and VR help or hurt the current trend of social interactions.

So if you don’t care about my awkward story about making fun of somebody’s bumper sticker, which I’ll tell, definitely get Henna’s insight on AR and VR, especially as The Vision Pros comes out sometime in the next few months. But this has been so great. Where can people find you? And more importantly, most importantly, where can people get your book now?

Henna Pryor: Thank you. I’ll answer the second question first. The book… you know, I feel like this is the corny answer, but everywhere books are sold. So Amazon, Barnes & Noble, Barnes & Noble, most metro cities-

Joe Casabona: [inaudible 00:47:32]

Henna Pryor: Yeah. And most of the metropolitan cities have them in store. It’s at a couple of airports as well. If you like to go indie, which I encourage you to, you can either go to bookshop.org or ask your local indie bookstore. They can order it for you. And I always encourage people to support local.

And then on socials, I’m Henna Pryor everywhere. I will say that LinkedIn and Instagram are my preferred playgrounds, so just Henna Pryor in all the places. I love to make new friends. I might make it a little awkward, but that’s kind of the name of the game. So link up.

Joe Casabona: Yeah, absolutely. I will link to those and everything we talked about in the show notes over at howibuilt.it/338. That’s 338 for the episode number. You’ll also be able to become a member over there and get ad-free extended episodes. Henna, thanks for joining us today. I really appreciate it.

Henna Pryor: Thank you for having me. It was fun.

Joe Casabona: And thank you for listening. Thanks to our sponsors. And until next time, get out there and build something.

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