Leaders as Humble as They are Successful

Refreshingly candid conversations with some of today's most humble leaders. Adam Kaufman dives into topics often left unexplored. His guests’ challenges, fears, and motivations show what it takes to become a humble leader.

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Doug Holladay: Ambassador; Professor; and Author.

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Doug Holladay: Ambassador; Professor; and Author.

Doug Holladay has spent his career focusing on Meaning and Authenticity and becoming 'a better version of ourselves.' Hoping to fill some of the void now present in everyone's lives as we find ourselves coping with a society nearly shut down during the Coronavirus outbreak, we invited this former Ambassador, White House advisor, current Georgetown professor and founder of PathNorth, to discuss the positive aspects of being alone; the merits of practicing Gratitude; and how to get comfortable with who we are.

The founder and CEO of Path North, Georgetown University professor, and former White House advisor teaches you how to find meaning, balance, and purpose throughout your career while reaching the highest levels of professional achievement—how to do well without losing yourself.

Rethinking Success on Amazon

Blaise Pascal, ca. 1666 “all men’s miseries derive from not being able to sit in a quiet room alone."

E.E. Cummings “To be nobody but yourself in a world which is doing its best, night and day, to make you everybody else - means to fight the hardest battle which any human being can fight; and never stop fighting.”

Kubler Ross 5 Stages of Grief

  1. Denial
  2. Anger
  3. Bargaining
  4. Depression
  5. Acceptance

Rudyard Kipling’s Poem “IF--”

Dr John Gotman’s “The Magic Relationship Ratio, According to Science”

Dave Douglas: Welcome to another episode of Up2. Eight years ago, Up2 started as a live event series, showcasing leaders who are as humble as they are successful. We try to focus our interviews on the non-business aspects of their lives, and in doing so, have found there is a real thirst to explore their hearts and minds in atypical ways. Today's episode is a special one. We've reached out to one of our most talked about guests, and asked him to return to the show for a second time, Ambassador Doug Holladay. Given the situation that the entire world finds itself in right now, dealing with the Coronavirus, it seems appropriate to have him back on the show if at all possible. Doug Holladay is incredibly eloquent when speaking about the perils of isolation and loneliness, a few of the challenges that many of us are facing currently.

Dave Douglas: That being said, we're conducting our very first interview over the phone, here on Up2. It starts off a little bit slow, but as Adam and Ambassador Holladay get comfortable, the conversation overflows with valuable insights and powerful takeaways. Thanks for joining us, we'll be right back.

Adam Kaufman: During the first season of the Up2 podcast, I had several companies and entrepreneurs approach me about potential partnerships, but I'm really selective before choosing to do something like that. One choice we did make happily, is to partner with Vivid Front, a full service digital marketing and website design agency, based in Cleveland, that works with both local and national brands. They've built their entire client base on referrals, and they've won a lot of awards including the 2019 Ink Magazine top 5000 fastest growing companies, North Coast's top places to work, and several others. They're known for their talent, they're known for their creativity, they're known for their culture, a firm I liked before we agreed to partner together for this show.

Adam Kaufman: Check out vividfront.com, or you can email me, and I'll introduce you to their dynamic leader, Andrew Spott.

Dave Douglas: Welcome back. You're listening to the Up2 podcast, and our guest today is Doug Holladay. And here's your host, Adam Kaufman.

Adam Kaufman: Hello everyone. My guest today is a UNC grad, a Princeton Theological Seminary grad, and Oxford University grad. He's been an advisor to three US presidents, he's worked with the state department, including a special ambassador to South Africa, he's been an executive officer with Goldman Sachs, and also co-founded his own private equity firm. How he's a Georgetown professor, and also the founder and CEO of a unique organization called PathNorth. And, just around the corner, he'll be releasing soon his first book, Rethinking Success: Eight Essential Practices for Finding Work and Meaning in Life, published by HarperOne, a unit of HarperCollins.

Adam Kaufman: Doug Holladay, welcome to this special edition of the Up2 podcast. We find ourselves in a very different context right now. What have you been up to?

Doug Holladay: Yeah, well... I've been trying to self quarantine, whatever that means. But I happen to sneak out every now and then.

Adam Kaufman: We won't tell anyone.

Doug Holladay: These are really interesting times. It raises a lot of questions for people about, are they comfortable being alone? And as you and I have talked, sometimes there's a difference between being lonely and being comfortable alone.

Adam Kaufman: Yeah, you're really good at solitude, that's one of the things I want to bring up with you. You were our first guest of our second season, and I want you to know, I don't think I've told you this, that among all the terrific leaders we've had on our show, your appearance generated the most positive feedback. And I still cannot believe how many people told me that they were either working out or driving, and they had to pull over or stop working out to take notes on some important comment you made, or some observation you shared.

Doug Holladay: Wow, wow. That's scary.

Adam Kaufman: It really is tremendous, I know you're being humble, you are humble. But really, a major impact last time. And I suspect we'll talk about some important meaning topics today as well.

Doug Holladay: Great.

Adam Kaufman: Someone recently asked me actually, it was Dave Douglas our producer here, what were my favorite moments of last season. And what came to mind is your counterintuitive emphasis, Doug, on perceived weaknesses and how if we embrace those and talk about those as our points of identity, rather than the more common brags that human nature, people seem to want to lead with, that we become more relatable.

Doug Holladay: Yeah, yeah. Absolutely. Our point of identity with others is not our strengths, but our weaknesses and that's the connecting tissue. But most of us are terrified to go there, because we've been told to project an external kind of persona or image that sometimes doesn't bear any resemblance to the real self. And so, what I'm trying to do myself and encouraging others to do, is try to align both of those, who you are inside with what you project outside.

Doug Holladay: So when you start to risk it a little bit and share that you might not know the answer to something, or you wish you were a better leader, telling your team these things or your board of directors, it does almost the opposite from what you think. Instead of making you appear weak, it makes you strong. Because they all know that they aren't as advertised, but it almost has to be someone has to do it first and begin to take the baby steps toward being much more authentic and real.

Adam Kaufman: But that can become contagious in a good way, and I was reading also your recipe for an oddly rich life, preparing for today. And it included one of the points similar to what we're talking about. I think it was becoming the authentic you, becoming the authentic you, revealing weakness. Why is that important?

Doug Holladay: Well, I think people... What they're drawn to, if you think of who you're drawn to, you're not necessarily drawn to perfect people or people that have just as an end in themselves have achieved a lot. But what you're drawn to is authentic people, some of them could be achievers, but some could just be very normal people who are really comfortable in their own skin. And so, the more authentic we are and the more we get in touch with ourselves, the more comfortable we get, the more relatable we are, the more connected, all the things we long for that this loneliness epidemic only highlights in the whole culture. We get these things because we're starting to admit our fears, our questions. And that's okay to admit them, to [crosstalk 00:07:29].

Adam Kaufman: You've really positively affected me on that, excuse me, I'm sorry. We're doing this for the first time, I'm taking a risk by doing my first podcast without having a guest in front of me, so forgive me if there's a bit of an interruption moment there, Doug. I'm sorry.

Doug Holladay: No problem, I need to be interrupted.

Adam Kaufman: But what you were just saying, you've taught me to do that, to embrace my perceived shortcomings and my fears. And I feel like I've seen the positive effects of that, so thank you.

Doug Holladay: Oh great. And I have too, I mean I think in the book, I tell the story in my class one time, I mentioned that. That's one of the first things I, when I teach this MBA course at Georgetown, the first day I said, "Your point of identity with everyone in here is not how smart you are or capable you are, or what a great leader you are, but your weakness." And then, a young man on the front row immediately interrupted me, said, "Professor, could I say something?" I said, "Sure, [Clark 00:08:32]." And he said, "You know, I've been trying to get into this class for a while, and I finally got in. So I'm going to be all that." And this is the first five minutes of class, he said, "I've always been strong academically, but I really lived in the shadows because I had a debilitating stutter, and it just caused me never to interact with people so I was always alone."

Doug Holladay: Very strong academically, as mentioned, but he said, "I went to an Ivy League school, my sophomore year," he's telling us this, "I decided I was going to take my life, I was so isolated." And he said, "Before I did it, I'm going to go up to some people and just tell them, I can't string three sentences together." And he decided to do this. Now, imagine that. He's telling the class this, and then he said, "I had two discoveries when I did that. First, the more I shared and tried to speak, I started to get more comfortable speaking. And it was really amazing. And second, the more I shared my weakness, other people started sharing those, and for the first time I felt connected."

Doug Holladay: And then he paused almost, like for dramatic effect, he said, "Guess what else professor?" I said, "What, Clark?" He said, "I'm the student body president of the MBA class here at Georgetown, and I have to give speeches all the time." So I, being a smart alec, I said, "So class, you're all superstars in here. Clark has revealed a massive failing and a weakness."

Adam Kaufman: [crosstalk 00:10:11]

Doug Holladay: "How many of you during break want to go out and get out of this course, go to the registrar and transfer? How many of you?" Obviously no one raised their hand. I said, "How many of you feel safer in your own weakness and mistakes and failings?" Everyone raised their hand.

Adam Kaufman: Of course.

Doug Holladay: I said, "If you learn nothing else, this is the life lesson that'll transform the way you lead."

Adam Kaufman: That authenticity Clark shared became, I'm sure, very contagious and others started sharing. How about you? Are you doing that? Are you good at being authentic? I've actually never asked you that before, I hope you don't mind.

Doug Holladay: You know, you would probably know better, others would. I try to raise the questions I have and the fears I have about leading, and I know there are so many things I'm not good at. So I try to integrate it into my leadership style.

Adam Kaufman: I think you're good at it, you're often saying, "I'm not good at this or that," and it helps others fill that gap.

Doug Holladay: Yeah, exactly. There're so many things that I'm not good at. I know I'm an imaginative person, I know I'm good at certain things, inventing solutions to things but I'm not-

Adam Kaufman: You're so creative, and you're so inclusive, not to stroke your ego. But those are two things I'm really fond of.

Doug Holladay: Well, I enjoy doing those and I feel I'm drawn to those. But I am a terrible operator, I don't know how to do all the things that good chief operating officers would do. That's why people like Melanie are on the team, and others, they're so good at these things.

Adam Kaufman: Right, right. Well let's switch now, we'll take you off the hot seat of your own authentic shortcomings. Switching to the undeniable most important topic of the day, the Coronavirus. You and I are not experts on that, so we'll leave others to address that, but we have to acknowledge it. It's had an impact on everyone, everything in society. So how are you doing during these uncertain times?

Doug Holladay: Yeah, good question. We started something with my family yesterday, we're going to do a weekly call, just to check in. And try not to make it too dramatic, because my tendency is okay, we've got to do something meaningful. Let's read an article or something inspirational. We just had a FaceTime, and just checked in with each other, how are we doing, you know?

Adam Kaufman: That's good, because you have people in different parts of the country, right?

Doug Holladay: Yeah, yeah. My two oldest are in LA and my youngest is here. So that was great. But you know, I think if you allow this to be, it could be a great moment to learn things, how to be still. Like Pascal in 1666 wrote in an unfinished book called Pensées, which in French means 'thoughts'. He wrote this, "The fundamental problem of a person is never learning to be alone within four walls." And so, you think of that for a minute, wouldn't it be a great test to learn... So many of us don't know how to be quiet, even when we're in our house, we have to have music on, we're on the internet, and television.

Adam Kaufman: I'm guilty of that.

Doug Holladay: Well, and we all can be. We just want to fill... And Pascal goes on in Pensées talking about distractions. This is in the 17th century, he's talking about how we distract ourselves from thinking about what really matters. So I think I'm urging myself and others, just sit still. I try to take some time every day, and look into the fire and just try to be still and be comfortable.

Adam Kaufman: You're piercing my heart, I went into the shower yesterday and I brought my phone in there to listen to music. Like, how stupid that was, just for the seven minutes or whatever I was in there. I've always been impressed about how you do bring quiet into your life, and maybe you were just about to explain that, but you meditate. And I find that very difficult. I've tried to take some tips from you on how to get that started. And you also, I believe, you take very high achieving leaders on a solitude retreat every winter, isn't that correct?

Doug Holladay: Yeah, yeah. So in PathNorth, we try to do disruptive things that almost deny people certain aptitudes and defaults that they can always run to. So, you were there a number of years back, we went to London and we went to a restaurant called Dans Le Noir, in the dark.

Adam Kaufman: Mm-hmm (affirmative).

Doug Holladay: Run and owned by blind people. So you go in, as you remember, it's pitch black for two hours. And it's unsettling-

Adam Kaufman: Quite.

Doug Holladay: ... to deny one sense. Well, I realized for me, when I was in graduate school at Princeton, I met a monk once. And he asked me to come out to the monastery. I went out there and I realized that this could be a great exercise to just go out, spend time in solitude like the monks do. So we've been doing this at a place in [Barryville 00:15:33], it's a Trappist monastery about an hour and a half outside of Washington. And we take hedge fund managers, CEOs, business owners, and for two and a half days we are together but alone.

Adam Kaufman: Mm-hmm (affirmative).

Doug Holladay: And it's a very different experience, being in a community and being together, but really not talking. So think of it, you eat together, there are seven services a day. The Trappist tradition, you go through this and they chant, and you can go to those, or not go to this. Some of our people have a real faith that come on this thing, some don't at all. And some are seekers, as C.S. Lewis called it. And they go, but it is powerful. It's unsettling. We tell them, "There's going to be moments that are really hard, when you're walking and you pass somebody. Do you touch them? Do you smile? Do you say hi?" And we say, "Look, the greatest gift you can give each other is just be in your own world, and just let go."

Doug Holladay: But I urge people to... We give them a diary, ask them to write down what bubbles up, what are your fears? What are your concerns? What about this experience? And I have to tell you, the people that have gone, it's been transformational. We had one guy that manages money for about 20 of the most powerful families in America, and he went and his wife called me up about a month later and said, "What happened to my husband? He is different." So he now takes a half hour in the morning and a half hour during the workday, and just goes alone, silent. And everyone said he's a deeper, better person because of this. You know?

Adam Kaufman: And the wife's very happy with you for doing that for her husband?

Doug Holladay: She came the next year, she loved it.

Adam Kaufman: I know one time I went to a silent retreat called [Manresa 00:17:37] in rural Louisiana. And I was a real disbeliever, how am I going to do this? It was actually four nights. And I couldn't get over myself, because I'm so important. I don't know if you've ever noticed, but the world revolves around me in my own head.

Doug Holladay: Yeah, I've been honored to be [crosstalk 00:17:55].

Adam Kaufman: Right. So I went down to this retreat though, because I trusted the invite-or, the person who was taking me. And it was a risk for me. And the first meal, like you're describing where you can't talk during meals, it was like 10 men around our table. And I noticed that at my table, and we're not talking, but I noticed that the owner of the New Orleans Saints, Tom Benson, he has now passed away but Tom Benson was there. And, the editor of the New Orleans Times [inaudible 00:18:24] newspaper. And I thought, if those guys can turn it off for a few hours or a few days, little old me, I can do it too. I should be able to do it, the world will be fine without me emailing and talking for a few days.

Doug Holladay: Right. Yeah, good. That's great. You really have to be brave to do this, and part of it is getting comfortable in your own skin.

Adam Kaufman: Right.

Doug Holladay: There's an interesting quote by E.E. Cummings, he said, "To be nobody but yourself in a world that's trying to get you to be everyone but yourself, is the bravest thing any of us could do."

Adam Kaufman: Everybody but yourself, I love that.

Doug Holladay: It's really brave to really try to discover who you are, because we all try to adopt certain personas, and imagine views of what success is and what it would look like, and we're trying to always project all these things. I mean, the whole advertising culture is built on the fact that we're dissatisfied. And you really say, how can I get comfortable with just me? And you really think of this thing, dust to dust, you know? We're going to someday be alone, on that deathbed, and just learning... Are we terrified with that? Can we learn how to do this?

Doug Holladay: So anyway, it's been a great learning for me. I love doing it. A couple of friends, we said, we've got to do this longer, because the last time I invited Raj Shah the CEO of Rockefeller Foundation. Raj flew right in from Davos so he was really in the hyperactive world of Davos in Switzerland, and showed up, and he was on that hyper zone. And all of a sudden, you could just see the peace take over, hour by hour, day by day. And he just loved it. Everyone says the same thing after two and a half days, "I needed more time."

Adam Kaufman: One of my other mentors, you're talking about the timing, you've met Jim Jamison, and you had him speak at your class.

Doug Holladay: Lovely guy.

Adam Kaufman: He has companies in six different countries, four different continents, always busy, always on the move. Yet he takes two weeks, two weeks a year, to go to rural France and to spend time with, ironically again, monks there to do something similar. And he swears by it.

Doug Holladay: Wow.

Adam Kaufman: Whether it's two day, or two weeks, I think any of this can make us better versions of ourselves.

Doug Holladay: Absolutely. It can start small, I did it with my class, I just finished it last time. Thankfully we slipped in before they closed down, started closing down all the schools. But I had them go off for an hour, I said, "You can't take any technology, no pen and paper," and it was terrifying for some. This is amazing, so the average age is about 30. But terrifying for some, and some of them said, "This was transformational." Just from one hour.

Doug Holladay: So, I just urge people, start small, baby steps. Go for a walk, don't take any electronic stuff. Just observe.

Adam Kaufman: What about all of this additional alone time we have right now? How do we make the most of this solitude without it becoming a time of loneliness? Loneliness is often one of your favorite important topics. So how do we make the most of it without it becoming a problem?

Doug Holladay: Yeah, I think a couple of things I've been thinking about. You need to have a little bit of structure in the day, because I think what terrifies people-

Adam Kaufman: Structure in the day, that's good.

Doug Holladay: What's terrifying people right now about this virus, is the ambiguity. It's almost like if you knew the worst, you can step up. And you say, "Okay, I have cancer."

Adam Kaufman: Let's develop a plan.

Doug Holladay: Yeah, Kübler-Ross has the five stages of grief you go through, and you go through those things, and the last stage is acceptance. You go from denial, number one, to acceptance. And sometime, in this case, I'd say some people are at different stages of that. They go through an angry stage, and a question, a blaming, and all these things.

Adam Kaufman: Victim stage, why me? Why can't I go to work or why can't I visit my mother in a nursing home?

Doug Holladay: And why did I lose so much, and who's fault is it that my portfolio is due on the third? And I'm terrified. So, I'd say number one is to understand that fear, the biggest challenge today is ambiguity. It's not knowing how long this is going to go on, what are the long term ramifications for our society and our world? And it's almost like, I had this friend, Jimmy Moreton, I mention this is in the book I think about, he was a tennis player, played in college. And I remember he went through a very difficult time, for two years he could not get a diagnosis, he was losing weight, had all these issues. And then he called me up one day ecstatic, he was so happy. I said, "Jimmy, what's going on?" He said, "Finally, I got a diagnosis!" I said, "Must be good news." He said, "It's not. But I finally know the diagnosis, and I can arrange my life accordingly."

Doug Holladay: And I think that's the challenge that people are facing right now. They don't know what in the world this means. Are we going to be in this same state in a year?

Adam Kaufman: When is my child going back to school?

Doug Holladay: Yeah, exactly. And all the issues that are caused by those kind of vagaries. And I think in the middle of that, what we need... It was almost like a Churchill-ian call. The thing that happened with Churchill, in the midst of the darkest hour in London and England, he would really speak out and give a vision. "We can do this, trust me, I have it." And he had built up the social and moral capital [crosstalk 00:24:48].

Adam Kaufman: Earned trust. Yeah.

Doug Holladay: So you almost need leaders right now who will believe for us, even when we can't believe for ourselves, we're going to get through this.

Dave Douglas: You're listening to the Up2 podcast. We'll be right back.

Adam Kaufman: Hello, my name is Adam Kaufman, and I'm thankful you're joining us today on the Up2 podcast. I want to tell you about a group that I'm grateful for, and that is TownHall, Cleveland's most popular restaurant, and one that I can say is the only place my wife tells me she can eat every meal, breakfast, lunch and dinner. TownHall was the first all non-GMO restaurant in the US a few years ago, and they're now expanding into Columbus, Ohio soon. I'm also very selective about who we choose to partner with for this podcast, and it was with open arms that I embraced the idea of partnering with Bobby George and TownHall.

Adam Kaufman: To learn more about what they're up to, you can visit townhallohiocity.com.

Adam Kaufman: One of the aspects of podcasting I enjoy the post is the ability to delve into long form discussions without any interruption other than a periodic commentary about one of our partners. I'm grateful that Calfee, Ohio based law firm, has agreed to partner with us. They have offices throughout Ohio, and also in Washington DC, in New York, and Indianapolis too. They are a full service firm, every type of legal need. One example I'll share right now, because so many of our listeners are entrepreneurs is not too long ago, a friend of mine sold his company to a public corporation. And with that came some restrictions and ramifications on his future employment, and to navigate through that properly he asked my advice. And without hesitation, I recommended Calfee, because I knew they'd have the right type of specialist to help him with his particular needs. And my friend continues to rave about that experience, and I'm very grateful that Calfee has agreed to partner with Up2.

Adam Kaufman: So whether it's selling your own business, or the more routine needs of creating your first will or anything in between, this firm can really do it all in terms of legal needs. Once again, the firm is Calfee, you can find them at calfee.com, or on the Up2 Foundation website.

Dave Douglas: Welcome back. You're listening to the Up2 podcast with Adam Kaufman. Today's guest is Doug Holladay.

Adam Kaufman: Now back to the loneliness topic for a moment, I was really intrigued when a couple of years ago the UK established a minister of loneliness cabinet position. They were kind of ahead of the curve.

Doug Holladay: Yeah, Theresa May, when she was prime minister did that.

Adam Kaufman: And you've been talking about loneliness for a long time. Are you hearing about any effective best practices to counter the loneliness right now? Is it FaceTime and Zoom and listening to terrific podcasts? How are your peer group dealing with this?

Doug Holladay: Well, I think you're really [inaudible 00:27:56] there, because I think there's been this real conversation going on, is technology the problem or the friend? You just look at this, you know, on the one hand we can recruit for terrorism because of the technology. All these horrible manifestations. The good news is, it's being used for good. As you know, Adam, last Wednesday we started a FaceTime with our community in PathNorth and anybody else who wants to be a part of it, where we're just talking honestly about the moment we find ourselves in. And I think people really benefited and appreciate it, because [crosstalk 00:28:34].

Adam Kaufman: Yeah, there were more than 50 participants on that one Zoom call.

Doug Holladay: Yeah, just our first one and I think it's only going to grow. But you think of this, you look in the Torah, the first five books of the Old Testament. In the Torah, in Genesis, it says it's not good for a man to be alone. Most of us associate that with marital things, the vow, when that's spoken. But it's also true when individuals get isolated, bad things happen.

Adam Kaufman: Mm-hmm (affirmative).

Doug Holladay: So, UCLA has this loneliness epidemic, and they've found that one of two Americans now [crosstalk 00:29:10].

Adam Kaufman: They have a study, you mean? UCLA has a study about it? Okay.

Doug Holladay: Yeah. UCLA. Actually, it's something called the Loneliness Index.

Adam Kaufman: Okay.

Doug Holladay: And they have found that one of two Americans self report that they're lonely now.

Adam Kaufman: Wow.

Doug Holladay: And that's growing. And so, what has caused that? Affluence. I remember my grandmother telling me during World War 2, the daughters of her boys who were off fighting, they lived together and they had boarders in their house and all that. Well, the very affluence that separates... I live in McLean, Virginia. We have these gargantuan houses. Who lives in these? They're so big, and you say, we're isolating ourselves. And that's a high class problem. But that's just one aspect of it.

Doug Holladay: I think this is a danger for everybody. There's always been fears about, is technology going to separate us? I have this great cartoon, it has two cavemen in front of a fire, and then one caveman says to the other, "Before we had fire, we used to talk."

Adam Kaufman: We should put that on our website, that's great.

Doug Holladay: And you know, technology has been a challenge. When the telephone came out, was invented, if you look at some of the papers in those days it was like, there goes the end of the family. We're not going to talk anymore. We're not going to have dinner together. So I think there's all that, but I think there's all these uses where people are now talking. We shared ideas on that call, where people are having virtual cocktail parties, where they're sitting there with a glass of wine or a cocktail talking to five other people. And that's kind of cool. We're just learning different ways to socialize.

Adam Kaufman: I'm proud of my wife, I'll chime in here. She taught her first-

Doug Holladay: Oh yeah, she's doing the yoga, she's doing [crosstalk 00:31:04].

Adam Kaufman: Yeah, she did her first Facebook Live yoga class, called Sanctified Yoga, and 72 people were participating via technology. It was so amazing. From different states, of course, and I think even one from Australia.

Doug Holladay: That's fantastic.

Adam Kaufman: I'll tell her you said that, thank you.

Doug Holladay: I'm so proud of her. Because I think we need to venture out and try these things, maybe some will fail but some will work.

Adam Kaufman: Take the risks.

Doug Holladay: Yeah, take the risk. But I think we have to try things and I think getting out of our comfort zone, saying okay, I'm going to try to connect in this new way. And for some of us, that didn't grow up with all these technologies that are part of our life in the way that they are for millennials and others, it's challenging. But it's wonderful.

Adam Kaufman: We're moving next to your new book, but first, I just had a conclusion listening to you. I mentioned the UK have a minister of loneliness, we don't have that position in the United States. But if I were president, I'll commit right now, you will become the minister of loneliness. This is such a good area of expertise for you. So congratulations for that.

Doug Holladay: Well thank you. It's funny, it's an observation. And the observation is, I don't care what level of success you have, whether you're a middle school principal or you're athletic director, or you're CEO of a Fortune 50 company, it's all the same. When you arrive at some level of success, the unintended consequences are to isolate you. So you have to develop strategies where you can break out of that cocoon. Because it's not a happy life, and it's [crosstalk 00:32:58].

Adam Kaufman: It's lonely at the top really is true, and the higher the top, the lonelier it can definitely be.

Doug Holladay: Yeah, absolutely.

Adam Kaufman: So, tell us about the book; Rethinking Success, published by a unit of HarperCollins, congratulations.

Doug Holladay: Thank you.

Adam Kaufman: What inspired you to write it? Who's your audience?

Doug Holladay: Well, exactly what it I just said there, the people who have experienced the unintended consequences of success and they're saying, "There's got to be more." So, my class that I teach, an MBA class at Georgetown, I talk about that. Aristotle called it a life of thriving, to have a life of real thriving and purposeful, I talk about you have to ask yourself 10 questions. So this is a variation on this, this is eight principles that really are important to look at. And I look at the importance of really understanding what is success and failure? It's like that poem by Kipling called If. He talks about those two imposters. And isn't it interesting? He didn't talk about the imposter just being failure, he said, "Success is also an imposter."

Doug Holladay: So I look at these things and say, all these things that seem so wonderful, have a soft underbelly. So I talk about the power of risk, the importance of knowing your story. What story you were born into, because your story, the one you were born into, is going to determine so much about how you view success, how you view meaning. How you control your own personal anger. And some would say, "So what's the difference between this book and great writers like David Brooks, Arthur Brooks, Adam Grant, Daniel Pink." They're all smart. Well, number one, they're all much smarter than I am. Number two, I think it's like the Hamilton musical, where Hamilton's singing, "I want to be in the room." And I think I've had the benefit of being in the room, at Goldman Sachs, at the State Department, at the White House, private equity, where I've been in the room with leaders and really seen them under pressure and make good decisions, bad decisions.

Doug Holladay: So, I've had the privilege of being trusted by a lot of really interesting people. So I've brought a lot of the richness of those experiences into this conversation, you know? I think of one, when I used to stay with Lawrence Rockefeller on Fifth Avenue. And I remember one time... He's deceased now, but I said, "Lawrence, what is it like to be a Rockefeller?" After we're drinking his great Bordeaux. And I said, "What is that really like?" And he said, "Well I have this reoccurring nightmare that I'm in the bottom of a well and my grandfather, John D. Rockefeller and my father are looking down on me scornfully, and they won't help me out. I'm trapped down in this well." And he said that feeling of being trapped, he said, "No one cries crocodile tears if you're a Rockefeller. But we have problems too."

Adam Kaufman: Right.

Doug Holladay: And so I've had these incredible experiences that have taught me, well, if people like that have experienced this great isolation and loneliness, no matter how much they have or how much they've accomplished, maybe it's okay for me to be authentic and honest about my [inaudible 00:36:38] and my struggles.

Adam Kaufman: Well you're meandering towards a question that I wanted to ask today regarding the book. I liked in the outline, the importance of knowing your own story, you just mentioned that. When, Doug, did you learn your own story and did that help you crystallize your career goals or what you wanted to be, or what you didn't want to be? When do people start to realize their own story, and what can they do with that?

Doug Holladay: Well, it's on an unconscious level until someone asks you the question. So, I'd see the lights go off with CEOs I work with and with my MBA students when I say, "You know, if you grew up in an angry household, that's what you've seen. I don't care..." And I just finished a book by a psychiatrist, "It doesn't matter what you were taught by all these parenting strategies, what you observed is how you're going to act." I mean, that's scary for some of us.

Adam Kaufman: It is, all of us who are parents.

Doug Holladay: Yeah, because some of us have grown up in really angry, violent families. And sadly, we're going to reproduce or reenact that stuff, unless we do two things; one is be honest about the story we were born into, and two, make different decisions. So, for me, I was unconscious of a real driver in my life.

Adam Kaufman: What was that?

Doug Holladay: The driver came back to my father, which he grew up in a small town in Mississippi. He was always really curious. And his mother was a big church goer. He tried to go there, but he would ask questions. And in those days, that was not celebrated or invited. So, my father increasingly felt disconnected from things of faith, and actually, became an atheist. So I actually grew up in an atheist family.

Adam Kaufman: Okay.

Doug Holladay: Which is kind of unusual, where you didn't have any input in that way. But I realized that my whole life, and this didn't happen until two years ago, where I was talking to the editor at HarperCollins. And he said, "Doug, why have you your whole life tried to create these safe spaces for leaders to explore what really matters most?" And a light went on, and I said, "I am trying to create the kind of space that I wish my father had. He never had a context to explore, because all they cared about, just believe, don't question. Don't be curious." And so, that's been my whole life. And whatever circumstance I've been in, I feel like I've asked those kind of questions of the leaders I've been around, then I've unwittingly created those kind of spaces.

Adam Kaufman: Thanks for sharing that about your own family. You mentioned earlier, a lot of this takes bravery. So I know it's no big deal to you, but not a lot of people would share that, so thank you. Let me ask you, do you still have any relatives in Mississippi? There's a reason I'm asking.

Doug Holladay: I think I do, yeah. I've got a couple doctors, and where are they... I'm trying to think where they are in Mississippi.

Adam Kaufman: Well, they're in Mississippi, that's all I need to know. I'm going to keep going here, because for some odd reason, we've had Up2 listeners in every state in America other than two, and one of them is Mississippi. So hopefully, you being on Up2 will get us downloaded in that great state of Mississippi. I'm being flippant, of course, after you shared something important. Doug, the theme of the Up2 podcast is featuring leaders who are as humble as they are successful. And one of the tenants of your book is about gratitude. I found this quote preparing for today's conversation, "Humility and gratitude are the twin characters of happiness." This isn't from your book but, "Humility and gratitude," so something important to me, something you're focusing on, "are the twin characters of happiness." And a man named Richard Edgerly said this, and he's a senior figure in the Mormon church leadership, interestingly enough.

Adam Kaufman: But I really loved how those two character traits were cited together. Why is gratitude, in your world, in your view, so important?

Doug Holladay: I think gratitude evokes to me pausing and observing around you. We're such a striving culture, I want more, I want to do more.

Adam Kaufman: That's for sure.

Doug Holladay: But what gratitude does, it forces you to step back and be quiet, and remember and recall, and just say, "Wow, there's a lot working. There's a lot of good in my life. In other words, you don't have to make a list of all the things that suck in your life.

Adam Kaufman: Right.

Doug Holladay: You say, "Oh my gosh, I wish I had this, how am I going to pay for this?"

Adam Kaufman: We think about it too much.

Doug Holladay: Yeah, we're obsessed with it. But what gratitude does, and neurologists tell us this, a lot of research on this, that if you just step back and every day just think of two or three things. They don't have to be dramatic, but I love this dark roast Italian coffee I just made, I like just sitting in front of the fire. Just capturing little things and writing them down. It's unbelievable what this does to your perspective and your outlook toward life. It's a discipline. And the problem is, everything today is more, more, more.

Doug Holladay: It was almost this guy, Jim Barksdale, who started Netscape-

Adam Kaufman: Netscape, I remember that.

Doug Holladay: He sold it for billions of dollars, and I think it was either Fortune or Forbes used to ask him every day, how much money would make him truly satisfied? And the first year it was like, $2 million. Then he got wealthier, he got up a billion, he was worth billions and billions. And he finally said, "Is there any number that would really make you satisfied and feel like you are where you are?" And he simply said, "Well, for one day I'd like to be richer than Bill Gates, but that'll never happen."

Adam Kaufman: Oh my gosh.

Doug Holladay: But you almost say, for all of us, there's these subtle, subtle markers that we say, if only I had this. So what gratitude does is enables you to develop a language and a practice of contentment. So gratitude enables you to say, "Wow, I have a lot. I've been really blessed."

Adam Kaufman: And that's a great aspect of gratitude on oneself. Like how that positively benefits me if I feel grateful.

Doug Holladay: Yes.

Adam Kaufman: You also talk about, and you put it into action all the time, you bestow gratitude on others, so I know how that makes me feel, or others feel, when you thank them for something. Everyone deserves more thank yous than they receive, and the most humble people say, "Oh, it's no big deal, that's fine, sure, I'll go on your podcast." But I really am grateful when you take time out of your morning to do something like this.

Doug Holladay: Oh, thanks Adam. Well there's an interesting guy, and this is a little terrifying what he came up with. It was a guy named Dr. John Gottman, and I think he teaches at the University of Washington. But he's kind of the leading expert researcher on relationships, and he counsels people but he also does a lot of research on this. But he came up with this metric, he can observe, like if he meets with a couple for an hour, whether they're going to make it longterm. And he said, "It's simply this; for every negative interaction you have with a significant other, whether it's your partner, your wife, a business colleague, for every negative one interaction, you have to have five positive." Now that's stunning to me.

Adam Kaufman: That is.

Doug Holladay: His research has pointed that out. And it's really hard to do, if you think of it. It's easy to criticize, "God, why don't you take out the trash?"

Adam Kaufman: Very easy.

Doug Holladay: You're this, you're that... And you just think, to find five things. So, I would say... There was a book written in the 80s, and it was called The One Minute Manager.

Adam Kaufman: Oh, yeah.

Doug Holladay: And it's a small book, but it had a great thing-

Adam Kaufman: Very popular.

Doug Holladay: It said, "Catch people doing the right thing." I always catch our teenage son, "Oh my gosh, brush your teeth. You're always late." I mean, you can make that list and it goes on and on. But if you catch them and have the same... You think about, where does the energy go in a relationship? It's usually negative.

Adam Kaufman: Right.

Doug Holladay: But if instead of that, you said, "Hey Adam. Would you come to my office? I got something I got to say." You're like, "Oh my gosh." "Hey, I just want you to know, you were so fabulous in that interview with Joe. That was really good." And it's like, wow.

Adam Kaufman: Affirming, people need to be affirmed more. And you are really good at that, and I loved how that was a major point in your new book. One more part of Rethinking Success I wanted to talk about for a few moments, do you have a little more time?

Doug Holladay: Sure. I think I have a couple weeks.

Adam Kaufman: That's right, that's right. We all do. The importance of taking risks, you talk about. Why is that important to helping us become better versions of ourselves?

Doug Holladay: Well, it's funny, when you look at the data about people in their last days, when you ask what would you have done differently, right up at the top is I should have taken more risks. And part of it is, they feel like they lived their life safely, and there was things they wish they would have done. One woman, the first time I heard this, she was what's called I guess a palliative nurse in the latter days.

Adam Kaufman: Mm-hmm (affirmative). End of life, right.

Doug Holladay: She's Australian. And she kept noticing this pattern when they would do these things. So, I'm really aware of that, that what does risk do? Risk enables you to keep focusing on the future and trying new things. And it could be small things, but it's just like getting out of your comfort zone. The problem with living a life... It's almost like if you're an athlete, if you play a game not to get hurt, you're going to get hurt.

Adam Kaufman: Mm-hmm (affirmative).

Doug Holladay: You don't go in the basketball game and say, "God, my goal for this hour, is not to twist my knee or hurt my ankle." I mean, what a terrible-

Adam Kaufman: Or playing [inaudible 00:47:42] defense rather than being real aggressive.

Doug Holladay: But if you otherwise say, it's to live. There are some risks, but I really want to feel alive. I want to try some things. And you look at a friend of ours, you know him, [inaudible 00:47:58] Atlanta wrote that book, they interviewed 500 people over 100 about their lives. And what was it about their lives that really caused them to thrive? And so much of it is they always were trying things, they weren't sitting in a chair and saying, "God, I might catch a cold if I go outside, oh I might sprain my ankle, I might get robbed." They didn't live that way.

Doug Holladay: As Ronald Reagan used to say, most of the fears we have never happen. So, you think of it, all that we have is this moment. But we contaminate the present moment by regrets about the past, which we can do nothing about, or fear of the future. The only moment we have is this moment. Just learning to be present. And it's a really tough thing to do, because we are always trying to plan and do this, and we all need to do some of this, but we need to also learn, how can I just be present with the people I'm with? It breaks your heart sometimes, you'll see people in a restaurant, a couple with their two kids, and every one of them are on their devices.

Adam Kaufman: Right.

Doug Holladay: And it's like, we're everyplace, but who we're with. And I think developing presence is really a habit we need to rediscover.

Adam Kaufman: Do you think you're good at taking risks? I know for me, it was a risk to try a podcast. I never played on a platform like this. And would have been much easier to not try it, and certainly downside scenarios could exist, being embarrassing, or lisping, or not having good guests, or not having listeners. But I decided to take the chance. Do you think you're good at taking risk?

Doug Holladay: I think I am, with some. I think I've gotten comfortable. And part of it is, when I look at my life, I've never been really that qualified for anything I've done. And I [crosstalk 00:50:00] there's been a confidence. And I think because I was loved well growing up, that I've felt... In my story, I felt confident to try things. I think when you feel unconditionally loved, the consequences aren't that great when you fail. But you just see how people are so fearful, did I dress the right way? Did I say the right things? Am I going to behave correctly? That's all a product of... It's all about you. And instead of saying, "You know, I'm just going to go there and be about others. I'm going to try to take a risk and love others and leave me behind there, my self absorption."

Adam Kaufman: Mm-hmm (affirmative). Well, I love how you weave a lot of these topics together, and I see you playing them out in your own life. I remember around Christmastime, you showed me your... I think you called it your gratitude list, but maybe it was things you were thankful for, or prayers and-

Doug Holladay: Yeah. It was a gratitude list.

Adam Kaufman: Okay, it was. And you laminate them, and you keep them. So you've had them for many years.

Doug Holladay: Yeah, I try to put them on one [inaudible 00:51:11] piece of paper, because these are little. And I'll shoot for everyday, but I might make three or four days a week. But the end of the year, you think of that, do the math on that, you have hundreds and hundreds of these. So I just said, "You know what I'm doing to do? Every year, I'm just going laminate that." So I have these thousands now, of just things for which I'm grateful. And a lot of them are inconsequential and small.

Adam Kaufman: And do you keep that just for yourself? Or do you show your family? I think it's just for you.

Doug Holladay: No, just for me. But maybe someday they'll want to see them.

Adam Kaufman: Right. That'll be in the next book maybe, or at least one year's version of that. I loved seeing that, and I don't have such a written list, it's a mental one. And I will tell you then, on my mental gratitude list, near the top, is you joining us today. It's been a wonderful gift to have you share your heart and your mind and some of your life experience with us, Doug, today.

Doug Holladay: Oh, thanks.

Adam Kaufman: I really, really appreciate you.

Doug Holladay: I appreciate you my brother, and I think it's great what you're doing. You've got a great voice for this, and you've got a great manner that's inviting and allows people to really explore things, honestly.

Adam Kaufman: Well thank you.

Doug Holladay: And you give them time to do it, which is great. I really appreciate that.

Adam Kaufman: Thank you for that. Congratulations on Rethinking Success. I'm positive it'll be a best seller, and I know folks can pre-order it on Amazon. Right?

Doug Holladay: Great, well thank you so much.

Adam Kaufman: Okay. And to all of our listeners throughout the US and around the world, we do thank you for listening today. Wishing good health and important family time together during these uncertain times. Lord have mercy on us all, and thanks again for listening.

Dave Douglas: We're thankful to Doug Holladay for joining us on such short notice. We also appreciate his honesty and the encouragement that he's given us in dealing with the isolation that's required in order to gain control over the spread of the Coronavirus. We wish you and your family all the best during this stressful time.

Adam Kaufman: Up2 is a production of Evergreen Podcasts. A special thanks to our producer and audio engineer, Dave Douglas. I'm your host, Adam Kaufman, and thank you so much for listening to the Up2 podcast.

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