Why Leaders Struggle with Emotional Depth (And How to Fix It) | Adam Dorsay | 627
20 Feb 2025 · 23 min
Dr. Adam D'Orsay, a psychologist who works with Silicon Valley executives, argues that leaders struggle with emotional depth because they lack connection to themselves first. Without that foundation, relationships with others crumble. His book outlines four dimensions of connection and offers concrete tactics: schedule purposeful activities, text with intention, stop doomscrolling.
Chapters
Welcome, welcome, welcome. This is Peter Winick. I'm the founder and CEO at Thought Leadership Leverage, and you're joining us on the podcast today, which is Leveraging Thought Leadership. Today, my guest is Dr. Adam D'Orsay, and I'll give you his quick bio because it's pretty cool. He's a licensed psychologist, as opposed to an unlicensed psychologist, licensed one. He's got a really cool podcast called Super Psyched. He's written a bunch of books and he speaks and he does lots of interesting and cool things. So welcome aboard today, Adam. How are you?
Thank you so much. It's great to be with you, Peter. And unfortunately, I've only written one book to date, but that has been a fabulous journey. I loved every second of it except for the fact that often I was tearing out my own hair because it is so frustrating, but really glad it's out. As Leonardo da Vinci once said, "Art is never finished, only abandoned." And so, I finished it and it's looking good.
Well, I use the plural because I suggest people read it twice. It was that good.
That's awesome. Ah, fantastic.
So, tell us a little bit about your journey and what, you know, you've got the TEDx talk and just tell us your journey as a thought leader because it's a bit unusual, I would say.
You would be 100% correct. I started out kind of in special education in grade school. I showed no signs of ever doing really anything.
And just to clarify that, not as a teacher, but as a— I just want to make sure that we clarify what special education in grade school meant.
Right. So for those who remember Welcome Back, Kotter, I was one of those students. And, uh, It was not looking super bright. And over time, I came to realize I had dyslexia and ADHD, and I was able to actually name it and deal with it. And I put myself through my own self-imposed, what I called my own Navy SEALs BUD/S training. Of course, it was nothing like Navy SEALs. Major respect for them, but I just really tried to make it hard so that I could become a father, so that I could become a psychologist. And that's what I did. I worked in the corporate sphere for a long time in Japan and the United States, and then ultimately earned my doctorate late in life, got those hours, made $10 an hour, no benefits for a few years. You know, every, every, every woman's dream come true. But my wife was so cool about it. She never once gave me an ounce of trouble for what I was doing. She knew that it was going to be good for us. She wanted a happy husband.
That's fantastic.
That's fantastic.
Yeah. So what is it that you do and for whom? Give us a sense of what sort of the portfolio of Adam World looks like.
You bet. So I do individual psychotherapy and sometimes couples work in my office in part of Silicon Valley. I work with a lot of the kind of the C-level folks that you might have heard of. Oftentimes, oftentimes they come in a little bit skeptical about therapy. You know, I'm here because my wife said I should try it out. I'm here because one of my colleagues said, you know, and I'm that I could use a place to talk. And they come in oftentimes saying some theme or variation in the first session of, "Hey, man, you got 50 minutes. Show me what you got." And by around minute 47, I check in and they are— I don't remember the last time somebody was not in. And I love what I do, so I do that. I also do resiliency training for high-tech companies. For 4 years, I worked at Facebook with their counterterrorism and child safety teams. They dealt with a lot of vicarious trauma. I brought in thought leaders with whom I would coordinate a program based on a topic. I called it Dark or Light. In some cases, we'd talk about dark stuff like psychopathy or terrorism. At other times, we talk about light stuff like positive psychology and things like self-forgiveness and self-compassion. Uh, got a podcast I love. It's, uh, an award winner. It's Nearly at its 250th episode. All kinds of thought leaders have been on it. Steve Kerr from the Golden State Warriors.
Yeah.
Temple Grandin from Temple Grandin. A whole bunch of great people. Laurie Gottlieb's been on it. And it's one of the most fun things I do. And then most recently just coming out with a book has been great. So it's called Super Psyched. It's about the 4 ways we connect. I really wanted to look at connection through 4 different lenses, how we connect to ourselves, how we connect to others, how we connect to the world, and how we connect to something greater. I guess last but not least, you mentioned a couple TEDx talks. I got one on men and emotions. I love it. It's called "Emotions: The Data Men Miss," and another one about friendship in adulthood, a topic I really care about a lot.
I was going to say the men and the emotions is on the TEDx 60 Second series because that's usually not something men are into, but I was joking. That's one of their nano talks, right?
That's really funny. I've not heard that one. That's pretty good. Yeah.
Yeah. So how does it, because you know, on the one hand it seems like, wow, there's lots of different stuff. And then it makes sense. Here's this ADD guy, right? That's got a whole bunch of different thoughts and interests bouncing around. But then there's connective tissue. Like what's the through line across all the different things that you do other than you?
That's really good. So the through line, it's funny, I was thinking about connection actually as a common common denominator unto itself. I'd done nearly 20,000 hours of psychotherapy with individuals and couples. I'd done almost 250 episodes on my podcast. I'd read a ton of books just like you. And the common thread, the common denominator was this nebulous term connection. Connection is what we want. But no book was really just talking about connection in its largest form in terms of like their books about connecting to partners, connecting to people at work. But what about connecting to yourself as a primary tool and then moving outward from there? It's almost like ripples in a pond. I see the center ripple as being ourselves, the most important connection. If we don't connect there, other connections will be profoundly impaired.
Do most people look elsewhere? Because if the connection to self isn't there and we say it's them, it's the relationship, it's my relationship with dot dot dot, it's the way that whatever, um, without having the courage to be more introspective or grounded or pick a word. Is that kind of the common— one of the common things you see?
Yeah, and I would say that they want to feel more alive. Like, have you ever been at a party and somebody shakes your hand, it's just this limp handshake, and you're just like, dude, what? Yeah, it's not very attractive. Sometimes we are like that with ourselves. There's kind of a limp existence when we're really doing stuff. We're not really alive while we are alive. And this book is really aiming to help people be truly alive during that dash between their birth and death dates. What a tragedy it is, right, to die without that.
Well, and then there's different cycles in life— middle age and this and that— where it feels like that might be a luxury when you're drowning in responsibility to others, mortgages, college, blah, blah, blah, all the stuff. You say, "Oh, geez, I'll get to me later." And later doesn't always come.
Later doesn't always come. And if we actually look at our day, if we were followed around like Michael Scott from The Office with a camera and we saw how we used our time, we would be appalled. We are busy. We are really busy, but we could still leave a voice text to a dear friend and say, "Hey, Peter, it's been like, I don't know, a minute. It's been 6 months since we last talked. Just want to let you know I've been thinking about you. Let's find a time to hook up and talk in person, via Zoom, phone, I don't care. You're really important to me." Send. Boom.
So stay there a minute because that text action or some variation on that text actually serves two, right? So when you send it, you feel good to say, I remember some good memories with my cousin Sheila I haven't talked to in a long time. It got me thinking good things and say, geez, I should reach out. And then obviously the receiver. So there's something selfish and selfless in that thing.
That's right.
Right.
It's, it's what I call enlightened self-interest. Yeah. It's like, it feels good for me. And it's good for the other person. But one of the ways that we can also connect with ourselves is we look on our Saturday schedule. Saturday rolls around, brewing some tea, on the Netflix, binge-watching something, I'm folding the laundry, I'm petting the dog, and I'm responding to texts and emails and scrolling while I'm doing all of these things. But yet I'm doing none of these things. And then Sunday rolls around and it's like 8:00 PM and we ask ourselves, "What did I do with my weekend?" We need to be more intentional. One of the things that we need is almost a reminder of these are the things I'm into doing. These are the things like if I've got 30 minutes and I do a cold plunge and I go into the sauna, I'm going to feel better about myself. I can make that time instead of dilly-dallying on the— dilly-dallying, that's not a word I use, but goofing off on—
You did. You actually just did dilly-dallying.
I just did it. All right. And add them first in God knows how long. It sounds like a second-grade teacher from the '70s dilly-dallying. But if we're more intentional with our time and if we know what we want and we write down like, "These are the list of things," almost like an old-fashioned Netflix queue when they used to deliver DVDs. If we can be reminded, "These are the things that actually give me an ROI." But stay there for a minute because—
it is harder and harder today not to state what your intentions are. We probably know what they are. If somebody said, hey, write down your things you'd like to be intentional about, that's probably not the challenge. But everything is fighting us for our attention, right? It's so easy to doom scroll or that 90 seconds between when you're online at Starbucks and they hand you your latte. God forbid you just take in a breath and look around you and take in the world, right? No, you've got an email or this to do, but staying focused and finding the time to be intentional. Because if you don't, the next thing you know, you're on the couch with a bowl of chips and Netflixing something not particularly interesting.
100%. We've always struggled to be intentional, I think, on some level. But as soon as 2007 rolled around and that iPhone was introduced and that blue light in our pocket saying, feed me, feed me. But the problem is We do not use social media. Social media uses us, right? And the goal, whether it's AI, social media, or something else, they're all important. They're good technologies. I'm not bagging on them. I think that they're really potentially fantastic. But like a knife, it's potentially used for surgery or to cut meat if, uh, or dinners, but it could also be used to harm someone. Similarly, social media technology It's just a neutral thing. It's a question of what our brain does when it's on that substance. And if we can be really thoughtful about how we use it and also make sure that we allocate time for the stuff that's going to give us a huge ROI in terms of a connection to ourselves. Everybody's got a different connection formula. I know the guy down the street who runs really, really fast. He's got to do that every morning. I would not do that every morning. I would not do that any morning. My body's not built for that. My father goes to the opera. I find it a very expensive place to sleep. So he needs his connection to the opera. I need my connection to my pets. He doesn't care about pets. So we all have a unique formula. And one of the things this book does is helps us really, really procure conscientiously our own connection formula. We figure out, oh, these are the things that will give me a sense of being alive.
Good. If you're enjoying this episode of Leveraging Thought Leadership, please make sure to subscribe. If you'd like to help spread the word about our podcast, please leave a 5-star review at ratethispodcast.com/LTL and share it with your friends. We're available on Apple Podcasts and on all major listening apps. As well as at thoughtleadershipleverage.com/podcast. So I, I wanna segue a little bit to the sort of the book journey for you. So now the book is out, but go back to what was the spark? What sort of got you going to say, yeah, you know what, I'm gonna do this. And then what's the gap between how you thought the process would be and what what it's been, because this is where I think a lot of people, they're not on the other side yet and they have delusions of grandeur and all that. You don't have patches on your jacket or a pipe.
Words matter.
And I'll call myself an author and all of a sudden I'll look like Mark Twain or something. But tell us about your book journey.
I'd be happy to. I did my doctoral dissertation very fast and I thought I'd be able to write this book very fast. Turns out, no, could not do that. Oh, by the way, I used no AI for this book. This was all from Adam intelligence or Adam non-intelligence, whatever. But so it was really hard.
I actually— Wait, wait, I think we should market the book as organic then if it's no AI used.
It would be in the organic section at Whole Foods for sure. Exactly. It was really, really hard. But the funny thing is I'd started a bunch of other books. But no other book captured my attention. I finished none of them, by the way, but this book I knew I had to see to the end. It was really interesting. I kind of plowed for many months, for about 12 months, and I had the book. It seemed to be finished in January, except I didn't like it. I didn't like the words I was using. It just didn't feel right. It was really funny. My wife said, "Let me hear it. Let's hear what you got.". And so I start reading it to her and she's like, I see why you don't like it. Like that's, that's how you write. That's not how you talk. And she's been listening to me for 20+ years and she was able to tune the book and say, this is how you would say it.
Well, stay there a minute because I think a lot of people, you know, you know, you mentioned your PhD. If you use the language structure, whatever, that one writes a really good nonfiction book. For your PhD, they would've, you know, red circle with an F, right? And so those two ways of writing, you know, need to be tweaked. So if you're trying to write a book that connects with humans to get ideas in their head, not the 7 academics that'll read your PhD.
100%. Yep. Yeah.
It's a different way. So I love that your wife picked up on it that says, well, that sounds like PhD Adam, but not sort of Adam around the house or real Adam or whatever.
Dude, totally. It's like, this is Adam trying to sound smart. And yeah, it wasn't quite, It wasn't hitting. And she was able to real— I called it almost like a piano tuner tunes a piano. She tuned the book. And I said, "Oh my God." It was so funny to be in the process with her. She's my best friend. She's the person I'm in love with. Every day I look at her, I'm just like, "Oh my gosh, I can't believe I got you." And she's really, really wicked smart, which is amazing. And she was able to see it and hear it and say, "Yeah, that's not how you'd say it." We went through the entire book. The content was not changed per se, except for the fact the way I phrased the content was changed much more dramatically so that it sounded like me. And I'm so grateful to her for sitting with me for all of those seemingly endless hours.
So what—
the book was done. It just wasn't one that I would stand by at the time. Now I love it.
Right. So besides the tone and the language, What were the other things that were surprising to you in terms of expectations you might have had around the process or the launch or the whatever, whatever, and what's actually happened?
Well, certainly writing 86,000 words is insane, and there are so many places where there could be an error. It's just, it's such a massive volume. I'd never written something of that ginormous size. The idea of trying to promote it, I'm not really naturally built for that. I've not really, really done a good job on the socials. I really don't know how to even use Instagram as evidenced by my entirely bad following. I'm good on LinkedIn for some reason. I think it's really more geared to someone in my stage of life, but using the other socials that my kids can use just like that, That's so great. But it's also been really pleasurable. I've been interviewed by people like you. I mean, I've seen you everywhere, Peter, and I've been longing to actually get a hang with you because, yeah, Peter Winick is kind of the common denominator on LinkedIn. You seem to know everybody and you seem like a really fascinating person. So I get to meet people like you and that's ridiculously fun. Different questions are thrown my way so I could think about the book a little differently. So this has been actually a very pleasurable experience. And no two interviews are alike. This is totally, this is us. This is you and me hanging.
Well, I like that because I think that there are two ways folks go about sort of doing the tour, if you will. One is it's kind of like the old days when somebody was launching a movie and then you saw them one night on Johnny Carson, the next night on Letterman, and they hit the same three bullet points. It's like, oh God, wind 'em up and do the try, you know, do their shtick and whatever. And the other is to just let it go and write and give the trust to whoever's interviewing you because they might come up with something that you never thought of or a connection that you never thought of in the book. And if you're too in your head about, I gotta get these, these are the 3 things that my people told me are the most important of the book. Who cares? Like, just let it go, right? Like, just have a conversation around whatever it's going to be, and then see how you can weave that in. That's, that's a harder challenge, I would say. You know, it's, it's more improv-esque, if you will.
In some ways, what we're doing is just, it's so much more real. Like, rather than me coming in with 3 talking points, I remember there was a Coca-Cola campaign back in the early 2000s, and they had to use the word refresh. And for some reason, these execs were on these news programs talking about this new Coke thing and they kept on using the word refresh and it was kind of pukey. I didn't want to hear that. I wanted to hear something real.
A marketing poll and that was the word that bubbled up to the top.
Exactly. It's like, this is what's going to sell. And what's so much fun about talking to you is, yeah, you give me unique probes. You bring in your Peter Winick style. And without that, this would not be as much fun. You would not have the numbers that you have. You are crushing it.
Right. Thank you. So it's a year from now. Let's make it like a fantasy date for one year from now and all your wildest dreams have come true relative to the book and we're doing the follow-up, right? So what is it that you're going to tell me is different than where we're sitting today?
Yeah. So there's things I'd like for—
other than you'd be on Joe Rogan or something far more impressive.
So there are things I'd like for the reader and there are things I'd like for me.
Yeah.
Let's start with the reader because the reader comes first. I really hope that people find themselves using their time more intentionally, that they feel more connected to the important things that they do and far more importantly to the people in their lives. The biggest regret that people have at the end of their lives is love left on the table. My hope is that people will summon up the courage to be vulnerable with the people they love so that, I hate to go super, super morbid here, but I'm gonna. At funerals, I'm sure you've heard somebody say, "I wish I'd told this person how much I love them." Right, right. And I want people to do this while they're alive. I want them to feel more alive while they're alive. I want to get emails saying, "Wow, you know what? I've been putting one or two things." I'm not expecting them to do all the things, but they put one or two things into play and have derived great joy. Vitality from it. Love it. The second thing I'd like is, for me, I'd love to be able to do keynotes at various places and spread the word. I love the idea of this becoming a bestselling book, and that would be so fun to be a part of that.
So, as you're saying that, one thing that struck me is one of the greatest gifts that an author or thought leader can give to folks is language frameworks, models, et cetera. Just thinking around, like, it would be really cool to be able to have an intention conversation. Like, not some manufactured, like, whatever. You gotta be at a certain level of rapport. You know, it's not like cheesy first date stuff, but like, kinda, what are your intentions, you know, the next year with regards to your health or your spirituality or your profession or your whatever? And then if you open with that, someone would sort of reciprocate with that level of vulnerability. So that could be an interesting thing to play with maybe.
100%. And what you're engaging in is something that Kalina Silverman, who showed up on my podcast, would talk about. She has these cards called Big Talk Cards.
Yeah.
And obviously you can't just meet somebody in the grocery line and just like bust out, you know, an initial of like, hey, what do you plan to do for the rest of your life? Or what do you hope to do before you die? That's a big talk question.
All I wanted to do was check out and pay for my plums. Thank you, sir. You're going deep.
Right, exactly. I really just wanted to see Mr. Hooper. I'm going Sesame Street. And buy a couple plums. I really don't want to have a big existential conversation. But humans do crave bigger talk than small talk. Of course, you got to start with small talk before you get to the big talk. As you said, you need rapport. But it would be really interesting to talk about people's intentions around their books. And I've not had that question. And I love that you asked it. Cool.
Well, thank you. Well, this has been awesome. You're one of the few people I get to meet that it's like, instant fun, instant early relationship cool stuff. But I wish you the best, and this has been a lot of fun, Adam. Thank you.
Peter, it's been a blast. So glad to know you.
To learn more about Thought Leadership Leverage, please visit our website at thoughtleadershipleverage.com. To reach me directly, feel free to email me at peter@thoughtleadershipleverage.com. And please subscribe to Leveraging Thought Leadership on iTunes or your favorite podcast app to get your weekly episode automatically.
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