224: How Having Awkward Conversations Can Completely Change Your Life in Surprising Ways



That’s the question that Melissa Dahl poses in her new book Cringeworthy, a Theory of Awkwardness. It’s also something that I’ve been pondering for about 10 years now. Particularly, the area of having difficult and awkward conversations and how they impact your life. My friend Jenny Blake had told me about Melissa and her work; I knew I had to meet her! Fortunately, I was heading to Austin, Texas to an event put on by Express (my favorite clothing company on planet earth) to record our podcast Live at South By SouthWest, one of the larger conventions and festivals in the world. I tweeted Melissa and convinced her to join me onstage to discuss how difficult and awkward conversations can completely propel your career forward.Listen to the entire conversation here:


Much like the word “happiness,” awkwardness is used to describe an insane amount of events, happenings, feelings and more. This ranges from accidentally walking out of the bathroom with your fly undone all the way to asking your boss for a promotion. After talking to Melissa, she confirms that the awkward conversations that are most difficult are possibly some of the most valuable.

Maybe it can be an opportunity to become that person you think you are or you would like to be.

Here are a few examples:

  • Asking your boss for a raise (awkward yes! Profitable? Very).
  • Telling your spouse or significant other that you want to stop taking on debt because you realize it’s trapping you (scary… even with one of the people who loves you most).
  • Setting boundaries with people at work who are taking all of your time, adding more to your plate and causing you to overwork.

All awkward, all a little scary, all difficult conversations. All of them can have a profound impact on your quality of life. All of them are opportunities to move a little closer to the person you’d like to become.   In fact as I think back, 100% of the events that made the biggest impact on my adult life have involved a difficult or awkward conversation. (I can even directly trace awkward conversations to over $300,000+ extra income over the last 7 years that I had a boss.) So yes they’re valuable blah blah… if that’s the case you might think “Can’t I make them any easier?”


I asked Melissa this exact question. Turns out there is. And you’re not going to like the answer. It takes intentional practice. You have to decide that you’re going to have the conversation, then do it. When you do enough of these you can actually build up an Awkwardness Tolerance (my words, not Melissa’s)! Additionally though, you can get better at making it easier in those difficult moments. Here’s an example that Melissa gave: “It’s the kind of thing like you’re going into a job interview and all of a sudden you’re like ‘Wait I forget how chairs work. What am I supposed to do with my hands?’ I just did this with my boss’s office the other day. She has a big couch thing and I sat down and I kind of put a pillow like this and then I was like wait is that weird?”

“Is this weird? It’s a weird thing to do and just couldn’t fixate or focus on anything but it.Those two things really get you locked in that cycle. Psychologists who study this say it’s partially caused by self-consciousness.” The way out is to focus on anything but yourself. “So you know if you’re lucky enough to be public speaking with somebody else you focus on the person in front of you. Just anything but yourself you can focus on.” “If it’s the job interview scenario, you prepare beforehand and maybe think about three things you’re going to say about the job or whatever. You know it just kind of like zoom out. Zoom out and focus on the big picture and just don’t focus on yourself because that is the best way to be like wait what do I do with my hands again. That’s something that helps.”


My experience is that it takes the same amount of effort, worry, discomfort, and energy to have a bad awkward conversation as it does a good one. You can either put in a little prep work in making these most effective or you can deal with the fallout from a bad conversation. I might be a little biased on this from years of working in HR and helping people untangle bad conversations like these. Here’s what Melissa told me about the research on how to make these conversations most effective: “There isn’t a ton of research on this but there is some. And what little there is has suggested that there are two things that help. One is “Perspective Taking” which is kind of a fancy word for empathy. It’s putting yourself in the other person’s shoes and trying to imagine how they might be feeling and remembering it’s not all about you….Maybe you’re having a awkward conversation because you want a raise. Think about it from your boss’s point of view. Don’t think about it from your point of view. Don’t frame it as it’s because the cost of living in New York or wherever you live has gotten insane. Frame it as, well this is what I bring to the company. This is why it makes sense for you to give this to me. It’s perspective taking. The other one is called “active processing” which is another kind of fancy term for that kind of cooler rational side of of a conversation. I’ve seen people online promote #MakeItAwkward meaning like you’ve got to get up into somebody’s face and you’ve got to make it awkward and tell them they’re wrong or whatever. But that’s actually not going to be that effective. Where you can actually change someone’s mind or have a useful conversation is to stick with that cooler side.”


It turns out it’s not about trying to be less awkward, or even avoiding awkward moments. I’ve personally experienced that when you lean into those moments you have the largest opportunity to grow and develop as a human being. Melissa refers to this concept in her book as “finding your growth edge.” If you want to learn more about your growth edge, definitely listen to the entire interview or download the transcript below. Afterwards, it’s your opportunity to build your awkwardness tolerance. What’s that conversation that you know you need to have, at work, at home, with a friend or coworker? You know which one I’m talking about. Take some of what you’ve learned and have that conversation. Remember it’s in these boundaries of awkwardness and discomfort that the best of life happens.

Moderator: Hi everyone. All the way in the back Hello. I'm totally going to get your attention you fabulous bungalow babes. Are you guys having a good time? Good. Wonderful. If you're having an amazing time and you happen to be in the center of the pit I'm going to need you to have an amazingly quiet time because we're about to film and record a live podcast which means we need some silence. And then if you want to party you go do that to the front of the bungalow. Cool but we can't wait to have you here because we have some really good programming coming up. We have none other than the top career change podcast on iTunes. This is the show that is all about career happiness, it's all about finding your path. It's where the high achievers go for all of their career advice. It is none other than the Happen to Your Career Podcast and here is your host career happiness expert Scott Anthony Barlow. Give him a big round of applause.

Scott Barlow: Welcome to the Happen to your career podcast. I'm Scott Anthony Barlow. This is the show where we share stories of how high achievers find career happiness and meaning. We are coming to you from beautiful, sunny, very warm Austin, Texas in the bungalow at Express. But that is not all we have going on here. I have a very special guest today. She is the senior editor for New York Magazine's The Cut and in 2014 she helped start NY Mags  uber popular social science site called The Science of Us. You probably heard of it. Her works also appeared in Elle Parents and Today.com and possibly most importantly she has a brand new book out called "Cringeworthy: A Theory of Awkwardness." I am super excited to welcome to the show Melissa Dahl.

Melissa Dahl: Thank you. Yeah go science.

Scott Barlow: So I am curious what do you describe what you do nowadays because you're for all intents and purposes, whether you like it or not, an awkwardest expert.

Melissa Dahl:  I know,I know. When I was pitching the book everyone said that. Are you ready for this? Are you ready to be the awkwardness guru? Yes I am. I'm a senior editor at The Cut where I cover health and psychology and I also run a site called Science of Us which is all about social science behavior. Kind of why we do the things we do. It's such a fun job it's just like chasing my curiosity around all day. And so that's where this book came out of.

Scott Barlow: I'm guessing you haven’t always had the book, you haven't always been the editor. So where on earth did all this start for you? Where did the awkwardness start Melissa?

Melissa Dahl: Well I think if I could armchair psychology myself my family moved around a lot when I was a kid. We moved like every year, every year and a half. And so I mean every young person is hyper attuned to social norms and you know what makes something cool in one place and what makes something not cool in your new school. You know we're all pay desperate attention to that. But my kind of theory about why I got so interested in awkwardness is I had to relearn that over and over and over again. The social norms, the social cues. You know I made some mistakes because I was following the last schools trend that was really cool in southern Louisiana. That wasn't cool in Northern California or when I left Northern California I still said hella a lot. And nobody says hella outside of Northern California.

Scott Barlow: Wait,Nobody says hella anymore?

Melissa Dahl: You know I hella want to bring it back. Lady Bird brought it back. I'm bringing it back. I think that I became really attuned to moments that deviate from the norm. Moments that make you stand out moments that make you feel awkward. I think that's where my obsession kind of came from that maybe I also became a little too good at causing those moments too.

Scott Barlow: A little too good. Well that's what we get to talk about. As it turns out I am really interested in what  we're going to talk about. With the book we're going to dive into a whole bunch of awkwardness to put it mildly. But I'm curious where you were and how did you end up in this world of editing and now a first time author?

Melissa Dahl: Yeah it's a really niche field. I'm a health journalist but I'm also specifically covering psychology which really there aren't a lot of us. I think we all kind of know each other. I guess how I got started was I wanted to do journalism. I am old enough where I graduated college and newspapers still kind of seemed like an option. I've always been interested in why people do the things they do. I started as a general reporter on a general assignment and then I moved on to the health writing. When I went to MSNBC.com I was on the health section for many years. But specifically I found that I was always really drawn to behavior. Health is mostly about why your body reacts a certain way, why your body gets sick or whatever. But I was more interested in questions like why do you cringe at the sound of your own voice on recording?

Scott Barlow: Why do you cringe at the sound of your own voice on the recording?

Melissa Dahl: It's actually a fascinating answer. So I did a piece on this for Science Of Us that ended up sort of inspiring the book. It's such a common thing to say that your own voice makes you cringe. I've even talked to people in promoting this book. I talked to people who do radio shows or podcasts who are like I can't listen to my own voice. I think it's so funny. There's an interesting physiological answer. Typically when I'm not talking into a mike I hear my own voice through the air and through the bones of my own skull and bone conduction transmits sound at a lower frequency than the air conduction.  It's really common for people to say oh my voice sounds so much higher than I thought it was I sound like a teenager or a chipmunk. That explains why it sounds different. But that doesn't really answer why it makes us cringe. That kind of gets us to my Cringe Theory which is I think the moments that make us cringe are when the kind of self you think you're presenting to the world kind of clashes with the self people are actually seeing and when those two things don't match I think those are the moments when we say oh that makes me cringe.

Scott Barlow: What are some examples of those moments? We've probably got some awkward people out here.

Melissa Dahl: So let's see. It's like you're in a meeting or something and you make a joke and the intention is to ingratiate yourself with your co-workers or whatever, but it just goes over really badly and maybe it offends them or something. I just made a joke like this actually. I worked for a women's website and I kind of made some joke about how nobody  likes sports or something and they just kind of took that the wrong way. I didn't mean. The self of me they saw was not the me I was trying to present. I'm trying to present this cool with you person and they just saw this person who was observing something about them that wasn't true anyway. When you tell a bad joke in a meeting or something. I think another thing people call awkward is like when you talk about careers. Maybe asking your boss for a raise or a promotion. And that that kind of gets this to a really stark like number. You're saying I see myself this way, I see myself worth this much, I see myself as this title, and your boss could say no I actually see you this much, I see you still as a junior staffer. So there's that kind of distinction between how you see yourself and how they see you.

Scott Barlow: So here's what I found fascinating as I read through your book you put some of the numbers behind how many people were willing to have that very awkward conversation, sometimes difficult conversation, to figure out what it would take for a promotion or ask for a raise or anything else that falls into that category. It's not an easy conversation. And a lot of the times it really does feel awkward. So first of all how can people look at that differently?

Melissa Dahl: I think that a lot of the things we call awkward are things that feel uncertain or make us feel self-conscious. And people don't like unpredictability. We don't like uncertainty. That's been shown in decades worth of scientific research dating back to the 1960s. But you can learn to withstand it. There's this cool research that shows a new way of thinking about emotions. And it says that the way you conceptualize a feeling actually changes the way you feel it. I started to think about that with these situations we call awkward. Maybe one way to look at it is kind of an opportunity. Sometimes, not always, but sometimes maybe it's because you're feeling uncertain of how it will go and you don't want to take that risk. Maybe you can start to think of it as an opportunity and it's not something to avoid or these are moments are showing you the gap between who you think you are and how other people see you. Maybe it can be an opportunity to become that person you think you are or you would like to be.

Scott Barlow: Well let me ask you about that. One of the concepts that you talked about a lot in the book and you called it a couple of different things, but talking about your Growth Edge for example. I love that concept because it's very much reframing the awkwardness or the Cringing conversations we all have every day. So tell us a little bit about what the Growth Edge is.  

Melissa Dahl: While I was studying awkwardness for the last couple of years, and then the word cringeworthy, I started to track how we use that word and typically we use it in situations or we think about it with things like I spilled coffee on myself, or oh I made a dumb joke in a meeting or something like that. But that's not always the way we use it. It's become like this catch all term for awkward. Like any thing that makes us vaguely uncomfortable whether it's like trivial or super serious. I mean while I was writing this book I saw a headline on The New York Times home page that said Why We Are Awkward. And I was like click on that. And the answer turned out to be a video about racial bias which I was not expecting. So I think if it's true that these moments show you the distance between who you think you are and how other people are seeing you, the idea of growing edge is the thinking of these moments as a time to self reflect and think. We tell kids it doesn't matter what other people think of you. And that's true to an extent but it can also be reality. It's true to an extent. You know you you shouldn't just always judge yourself by how other people understand you. But there are times when it's valuable to take in how other people see you. I had lunch with my cousin earlier today and I had a big taco and I got a bunch of kale or something in my teeth and she was like oh hey you got it. You better address that before you go to your panel thing. I couldn't see it. And to me that's kind of an example of what I mean by this.

That does make me feel uncomfortable and kind of awkward to be like oh I'm such an idiot. I have this stuff in my teeth. But I wouldn't have known about it if someone didn't point it out and I'm so glad somebody pointed it out. So some of these moments can be moments you can use to improve.

Scott Barlow: So you know one of the things that I found really interesting too is you talked about how it's really one thing to believe in the power of awkward conversations but it's an entirely different thing to initiate them. And first of all a little bit of backstory for those who haven't read the book yet, those people who are willing to have awkward conversations it seems like build up a tolerance. And those people can potentially have more success in some ways when you're, I don't know if the right word is less afraid.

Melissa Dahl: There's this business woman I interviewed for the book. Her name is Alison Green and she runs the website Ask A Manager and she is basically an advice columnist for awkward workplace issues. She's kind of become a friend actually through email. I interviewed her multiple times for the book. And so much of her advice, people will ask her just all kinds of outlandish things like somebody emailed her and asked her “one of my coworkers keeps keeps putting spells on other co-workers, she thinks she's a witch and keeps putting spells on other people.”

Scott Barlow: If I had a nickel for every time.

Melissa Dahl: So there's outlandish ones but there's also these quieter moments of awkwardness to where you know a friend at work keeps asking me to go to lunch and I don't like them in that way. I don't want to become actual friends with them. I got promoted and my boss didn't tell anybody.

Scott Barlow: Oh yeah that is kind of the ultimate epitome of all this in some ways.

Melissa Dahl: Yeah it's somewhat awkward conversations. I realize I'm a big fan of her site and she's answered thousands of questions over the years and almost every single question can be boiled down to the same advice which is you have to have the awkward conversation, you have to talk to them. You either have to have the conversation or you have to live with the thing that's bothering you is what she told me. And she told me actually sometimes she will check back on people and a lot of times they don't take her advice. They just left the job. So it's something that is hard to do.

Scott Barlow: Okay, so let me ask you about that then. We know that it's worthwhile to have awkward conversations. It's difficult to have awkward conversations. So what can people listening actually do in order to get better at having those crazy awkward conversations?

Melissa Dahl: There are two things here. There isn't a ton of research. I mean I am a science journalist so I kind of like to have this stuff backed by a ton of good evidence. There isn't a ton of research on this but there is some. And what little there is has suggested that there are two things that help. One is perspective taking which is kind of a fancy word for empathy. Kiind of putting yourself in the other person's shoes and trying to imagine how they might be feeling and just remembering it's not all about you. If it's in the context of work or something and maybe you're having a awkward conversation because you want to raise or something. Think about it from your boss's point of view. Don't think about it from your point of view. Don't frame it as it's because you cost of living in New York or wherever you live has gotten insane. Frame it as, well this is what I bring to the company. This is why does it make sense for you to give this to me. It's perspective taking. And the other one is called active processing which is another kind of fancy term for that kind of cooler rational side of of a conversation. I've seen people online promote so-called awkward conversations meaning like you got to get up into somebody's face and you've got to make it awkward and tell them they're wrong or whatever. But that's actually not going to be that effective. Where you can actually change someone's mind or have a useful conversation is to stick with that cooler side. And there are ways to do that too.

Scott Barlow: But as I think about the types of awkward conversations that we probably should have but we don't want to have there's a whole range of them at work right? Like you talked about earlier where you said that your boss promoted you but didn't tell anybody.

Melissa Dahl: That's a real story that happened to me. I think that's in the book.

Scott Barlow: Seriously I totally did not see that. And how did that go?

Melissa Dahl: It was ridiculous. Yeah I got a secret promotion. I got promoted and then they didn't tell anybody for like 9 months. And this is before I went through my awkward project or whatever and I just was too scared to have that conversation and ask about it. But it created more awkwardness for me because I kept having to invite myself to meetings or people would ask me oh don't you have to check this with so-and-so. No, no I don't. So yeah work is a weird place.

Scott Barlow: Did you end up having the conversation? Months later?

Melissa Dahl: Yes. I mean I sent a couple of e-mails and yeah it finally happened. But it was weird.

Scott Barlow: You know I found it really interesting about the concept of building up a tolerance to awkward conversations and I feel like if you take comedians as an example comedians have a great tolerance to awkwardness. But everyday people don't necessarily have that tolerance where they're having those really awkward moments all the time and practicing it in some way. Well first of all how do you think about that? And second of all what can you do to practice so that you can have that tolerance?

Melissa Dahl: There's this guy, a clinical psychologist in Boston that I interviewed for the book and he works with social anxiety patients or people who experience awkwardness to an extreme degree that hold them back from doing things they want to do. And he uses in their treatment a version of exposure therapy, kind of like the idea if you're scared of spiders. The idea is you just have to keep exposing yourself to a spider and soon you won't be afraid of it, which I don't know if that would work on me. I hate spiders. But he thinks the same is true for social phobia. He basically has them brainstorm what would be the most embarrassing thing you could think of to do. Okay now go do it.  So the things he's had people do are just ridiculous like he'll have them go into a bookstore and say to a clerk excuse me, do you have any books about farting or he'll he'll have them go to a drugstore and ask a pharmacist excuse me is this the smallest size of condoms you have.

Just like on purpose to make themselves look ridiculous and not hurt anybody else. But just look ridiculous based their social fears of looking very silly. And the point is to show them it's not that bad. Nothing's going to happen to you. And to build up a tolerance. Because if you're used to it you get used to this feeling in these situations that are kind of low stakes the kind of silly. The idea is you'll be able to handle it in your real life.

Scott Barlow: After you've asked for the small size condom than the rest of it is just no big deal.

Melissa Dahl: Yeah exactly. You know this is sort of a tangent but there's a theory that that's how they think dreams work. That's why we have nightmares. It’s kind of like nighttime exposure therapy. It’s something that you're afraid of in real life and that maybe the point is you face it in your dreams and then you get better at it. Facing it in real life.

Scott Barlow: I've certainly seen a lot of this too. I mean I remember a time with my first business, a painting business, a really long time ago - I remember having this person who is having a terrible experience with my crew and I showed up to their house and the guy had apparently just lost his front teeth in a biking accident. So he's still wearing his biking shorts and he's yelling at me with no teeth just as much as he can. And I didn't know what to do. Yeah and I have to go through something like that.

Like other things maybe aren't as big deal if you have a guy in bike shorts yell at you with no teeth?

Melissa Dahl: Yeah I have. I have not had that one. No but. This guy's name is Stefan Hoffman. He’s published peer reviewed papers on this and he claims like an 80 percent success rate. So the idea is kind of putting yourself in uncomfortable situations if you're kind of sensitive to this feeling which I am it's always kind of driving me insane. But the idea is starting small and then you can work your way up.

Scott Barlow:  So let me ask you one more question here. If you are in the place where you were, you know before you started. I mean we just had this conversation before we walked on and everything like that like you used to be afraid of public speaking.And now you're sitting up here and speaking publicly. So what would you advise those people who do have this very intense fear of moving moving forward with those types of normally awkward conversations. What would you advise them to do?

Melissa Dahl: Yeah there are so many things that I have just ripped off for my book that apply to my own life which I guess is good. There's all this research and psychology linking nervousness to self-consciousness and a big part of feeling awkward. I think it's feeling self-conscious. There's all this research showing that the two things are linked and self-consciousness triggers nervousness, nervousness triggers self-consciousness and they kind of just exacerbate around the awkwardness cortex and play book. And it's the kind of thing like you know you're going into a job interview or something and all of a sudden you're like wait I forget how chairs work. What am I supposed to do with my hands? I mean I just did this with my boss's office the other day. She has a big couch thing and I sat down and I kind of put a pillow like this and then I was like wait is that weird? Is this weird? It's a weird thing to do and just couldn't fixate or focus on anything but it. Holding this pillow is that weird. So those two things really get you locked in that cycle. But there is a way out. Psychologists who study this say if it's partially caused by self-consciousness the way out is to focus on anything but yourself. So you know if you're lucky enough to be public speaking with somebody else you focus on the person in front of you. Just anything but yourself you can focus on. If it's the job interview scenario, you kind of prepare beforehand and maybe think about three things you're going to say about the job or whatever. You know it just kind of just like zoom out. Zoom out and focus on the big picture and just don't focus on yourself because that is the best way to be like wait what do I do with my hands again. That's something that helps.

Scott Barlow: Do that when you're in the awkwardness vortex.

Melissa Dahl: Yeah well you can break out of it though. It's just do not zero in on what your weird hands are doing. I'm kind of a little concerned what my feet are doing right now but I'm not going to focus on them. And then he other thing is kind of in tandem to that thinking. I don't like speaking in front other people. I don't like promoting myself but I've started to try to think of this book as a third party thing separate from myself. It's this message so it's not me. I'm trying to promote it. But I think I've found some things that I think will really help people. So I'm just the conduit for that you know. And so when I do speak and when I do events and I do interviews and stuff I just try to focus on getting the message across as clearly as I can. So hopefully if you are someone who is plagued by self-consciousness and you feel that way at work sometimes, you like your work and you can kind of just zoom out and think okay, what am I trying to get across here.

Scott Barlow: I can absolutely appreciate that and I would say that having read the book if you're in the situation where you're finding it more frequently very very awkward or if you're in the situation where you're finding it to be a challenge for you to have these types of conversations that you know that you should have and you're not happy or you're not doing the things that you need to do, this book absolutely will help. I appreciate you writing an amazing book. I appreciate you flying to Austin, Texas to have this conversation in the first place and a huge thank you to Express as well for being able to put this on. I've had so much fun getting to meet you and being able to learn how to be less awkward.

Melissa Dahl: Yes. I actually don't think it's about being less awkward. I think it's more about just being comfortable with it. Just being comfortable when things are awkward. You know I just had an awkward thing putting on my mike. It was awkward. They wanted me to put it on under my dress. It was very uncomfortable. But just being more comfortable when those moments come around and just realizing that they're going to come around.

Scott Barlow: You know I love that. Let's end on that. No it's not about being less awkward it is about being more comfortable in the moment when those awkward moments come around. I so appreciate it. Thank you very, very much for being here. It’s been a ton of fun and we are out. Thank you all.

powered by

Ready for Career Happiness?

What Career Fits You?

Finally figure out what you should be doing for work

Join our 8-day “Mini-Course” to figure it out. It’s free!