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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Ambassador Doug Holladay: Embrace Your Fears and Live a Life of Meaning

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Ambassador Doug Holladay has a lot of knowledge to share. Having a career so varied as to include being US Special Ambassador to South Africa, advisor to several US Presidents, an Investment Banker at Goldman Sachs, teaching at Georgetown University, and many other positions, there are countless reasons to pay attention to what he has to say. Listen in to his conversation with Adam Kaufman about what really matters in life.

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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 VividFront, a full service digital marketing and web site 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 Inc 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 the show. Check out vividfront.com. Or you can email me and I’ll introduce you to their dynamic leader Andrew Spot. Hi I’m Adam Kaufman and you’re listening to the Up2 podcast. I’ve been fortunate throughout my career to be networking and serving and working with some of the most successful and influential leaders in America. Eight years ago we started Up2 as a live event series which showcased leaders who I thought were as humble as they are successful. The humility piece is very important as we identify these leaders who can hopefully inspire others. And over the years we’ve interviewed trailblazers from the fields of medicine, from business, from the military, nonprofit leaders, from politics and more. We really focus our interviews on the non-business aspects of their lives and we found that there is a real thirst to explore their hearts and their minds in maybe atypical ways. So time and again attendees of Up2 asked us to expand the event so that more people could participate and benefit from the special conversations taking place. And that’s why we started this podcast. Our guest today has been a U.S. Special Ambassador, a Wall Street executive with Goldman Sachs, an adviser to several U.S. presidents and countless corporate executives, co-founder of his own private equity firm, the executive producer of a PBS documentary, his opinion pieces have appeared in The Washington Post and the USA Today the biggest papers in America. He’s the founder of a high impact mentoring program. He’s even had an initiative bringing together people of different faiths. He’s a professor at one of the country’s top business schools. I’m still going. A board member of a historically black Morehouse College. Board member of ABC Squared looking for a cure for brain cancer. He’s the founder of Path North, the context in which I met our guest today. He’s the founder of a significant men’s retreat The Windy Gap in North Carolina. He played college lacrosse at UNC. Earned degrees from both Oxford and Princeton. And I know he’s working on a book that he’s nearly completed. My goodness Doug Holladay, I wish you spent more productive time with your life. Welcome.

Doug Holladay: I’ve always been lazy.

Adam Kaufman: My goodness. Unbelievable. How are you doing?

Doug Holladay: Good. Good. Thank you for doing this. This is your first podcast I think?

Doug Holladay: I think so. Yeah. Nobody else would have me. So it’s delighted.

Adam Kaufman: Well welcome to Up2. You are the epitome of what we like to feature here. We like to showcase leaders who are as humble as they are successful.

Doug Holladay: I don’t know if I’m either but I’m glad to be with you.

Adam Kaufman: Well let’s start simply with the book. What’s the book about? You’ve been working on a book for a little while. Tell us about it.

Doug Holladay: So this book kind of pulls together Adam, everything that I’ve cared about all my life from a young age. Which is about, how do you discover meaning on the journey? Because so many of us get so busy doing that we forget what it means to be. And what it means to really explore and to use our imagination to really discover the deeper purpose for why we’re here. You know what’s beyond success? There’s a great quote a Southern writer wrote “You can get all A’s and flunk life.” And I think so many of the people that I’ve had the privilege to know, whether they had wealth, notoriety, accomplishment of all sorts. They have one thing in common. It can isolate them, disconnect them and they find like the old movie you know what’s it called, Alfie. They’re saying, “What is it all about? Is there anything more?” So that’s been my journey. That’s what the book’s going to be about. It’s gonna be for people… I’d say almost anybody that that has had some measure of success on whatever level whether the CEO of a Fortune 100 company, hedge fund manager, or teacher of the year in the fifth grade.

Adam Kaufman: Right.

Doug Holladay: There’s unintended consequences of accomplishment. They can isolate you in a weird way.

Adam Kaufman: You’ve taught me how loneliness at the top really is a true phenomenon and the higher the top the lonelier it can be.

Doug Holladay: It’s tragic. And the mistakes you make. And you say, “How does that happen?” Well part of why it happens is you have unlimited resources to— All of us have flaws but when you have these kind of resources and access you can do even more damage than the average bear.

Adam Kaufman: And I feel like a lot of the people around these successful leaders are afraid to say “No.”

Doug Holladay: Yeah.

Adam Kaufman: Whether it’s the Hollywood executive who everyone apparently knew what was going on there but they were afraid to talk about it because he was so powerful.

Doug Holladay: Yeah. No you’re absolutely right Adam. So I tried to talk about how do you create a life so that doesn’t happen? You know we all make mistakes, we all screw up but there are the… You know Aristotle talked about a life of thriving and the elements that contribute to that are really knowable. That’s what’s astonishing today. You know that isolation produces bad things even in the book of Genesis. One of the first things it says it’s not good for a man to be alone. We usually think of that in the marriage context but it’s in a life context. Bad things happen and when we get isolated and we’re in an age now where I think it’s over half the people in America live alone. Where the former Surgeon General Vivek Murthy identified loneliness as the top health crisis, not smoking, not obesity but loneliness.

Adam Kaufman: In the UK last year they even created a minister level position, Secretary of Loneliness to combat loneliness.

Doug Holladay: Yeah. So I think in my book what I’m trying to do is say these things are knowable. One of them is to create a posse in your life, you know in a faith context we call that fellowship. But who are the people that you can check in with that really give a damn whether you get up in the morning. I mean you hear these terrible stories where somebody died and a week later somebody somehow finds that out.

Adam Kaufman: Right.

Doug Holladay: You know it’s just, we’re in a very strange time.

Adam Kaufman: Early on I’d like to share with our listeners that our guest today Doug holiday is himself a spectacular interviewer of others so it’s a thrill for me to be interviewing you Doug do you have any good tips on how to interview powerful people? Don’t fall asleep on them, that’s always a problem.

Adam Kaufman: OK good. I’m caffeined up today.

Doug Holladay: And don’t get in a fight with them.

Adam Kaufman: That’s always good advice too. We’re not on like Crossfire. Pat Buchanan and Michael Kinsley. When you interview leaders whether it’s for your book or on live stage situations are there any common traits among high achievers that really stick with you?

Doug Holladay: Yeah I think you know as I mentioned A. Many of them are disconnected and lonely. It almost goes without saying that sadly. I think the other thing is a lot of time with their children. They haven’t connected well because where they’re comfortable is doing and making and creating and making money or whatever it is. And as a result that’s their comfort zone. And this other messy zone of children and their crazy—

Adam Kaufman: It’s a little more nebulous it’s not so black and white as an Excel spreadsheet.

Doug Holladay: Right. So they can tend to disengage there. The other is I think many of them don’t have a language particularly men to talk about what matters because most men really are taught to shut down at a very young age you know, “Be a man, be tough.”

Adam Kaufman: Right.

Doug Holladay: So if you doubt me on that in the morning if you go out running or walking you typically see three women walking together and if you eavesdrop they’re talking about stuff that really matters. Their kids, their marriages, their depression, or whatever it is. Men are so afraid to be with another man unless they have something to do. Play golf, go to a game.

Adam Kaufman: Smoke a cigar.

Doug Holladay: Yeah it’s got to be almost task oriented and often it doesn’t really get down anything that really matters because they don’t have a language. So what I’ve tried to do is try to make it easier for men to talk about what really matters and try to get them… Asking the right question is always huge. I remember when we had our salon for Path North in San Francisco and it’s like in 10 minutes half the room was crying. These were top financial people and CEOs and I said simply ask this question, “What would your kids say is most important to you?” And oh my gosh all of a sudden…

Adam Kaufman: The self reflection begins.

Doug Holladay: Yeah, they don’t want to answer that but it’s terrifying on a certain level.

Adam Kaufman: The honest truth could be tough for them to hear.

Doug Holladay: Yeah for all of us you know.

Adam Kaufman: Stephen Covey wrote one of the best selling books of all time The Seven Habits of Highly Effective People. You have had a career where you could almost write like the opposite. The Seven Problems of Highly Effective People. Maybe your book is about that indirectly or?

Doug Holladay: Well it is indirectly. It’s my course that you know about Adam that I teach at Georgetown doesn’t teaches at Georgetown and business school. And it’s a very different course it’s the kind of a mash up of the humanities the arts theology finance business all kinds of things. But I center around 10 questions you have to ask to have a life of thriving. And I think the discovery process is in asking the right questions.

Adam Kaufman: So we’re sitting here in Washington D.C. today. You live here, you also have a place in New York. You’ve been to Africa over 30 times. I mean where do you find the most meaning geographically when you’re feeling most alive?

Doug Holladay: That’s a great question Adam. I think it’s with the poor. You know in Ethiopia that was a life changer for me. My first time in my early twenties and I’ve been going back ever since.

Adam Kaufman: You’re going this fall too right?

Doug Holladay: Yeah I’m going this fall. I think most people think of it wrongly. When Jesus talked about you know the poor. I think he meant more what they do for us than what we do for them. So when I tell people when they go to third world countries and they have these things I’m going to go for three days and change the world. I say you know why don’t you go for three days and change yourself? Because if you are attentive you’re going to learn things about what really matters.

Adam Kaufman: Yes.

Doug Holladay: And it’ll be astonishing. So I’ve been going for all these years for my own sake and it just feeds me it puts everything in perspective. I’ve sent so many CEOs and so many of their children to Ethiopia for example because it puts everything in perspective. Instead of saying you know should I buy a 30 million dollar home in Greenwich, Connecticut or a 40 million dollar— They go over there and they realize none of this crap matters.

Adam Kaufman: This story reminds me, I wasn’t even planning on bringing it up, one of my favorite stories of yours is one of your peers had you mentor their son about what job to take, maybe out of business school. You gave him some different advice. Do you want to talk about that a little bit?

Doug Holladay: Yeah yeah yeah. So this is a guy who is number two at a Fortune 100 companies. He said, “Would you meet with my son who’s graduate from business school and he’s wondering about what to do?”

Adam Kaufman: He had all the offers from the cool firms.

Doug Holladay: Yeah but he also knew he wanted to stay in this one place and he knew Morgan Stanley was hiring two people. So my friend said, “Would you meet with my son?” So he flew up and he’s in my office. And I knew what he wanted. He was kind of thinking, “Well maybe Doug knows somebody and can help me because he said I know the other people competing for the job and they had better grades. And so they’ll probably get the job.” But he said, “What do you think?” And I said to him I said, “Well Blake here’s my thought. Even if you are offered the job I wouldn’t take it.” And he looked at me like, “What the hell that I come all the way up here for?”

Adam Kaufman: Bad advice.

Doug Holladay: And I said, “I would do something different. Why don’t you make yourself interesting and do something else?” He said, “What do you mean by that?” I said, “Well you know I’ve been around all these elite firms and you know Goldman Sachs, you’d be interviewing people after they were Rhodes scholars, they won the Nobel Prize and you know everybody has everything.” And I said, “So I would say do it contrary. Do something really different.” He said, “What are you talking about?” I said, “For example have you ever been to East Africa?” He said, “No.” I said, “How about Nairobi? That’s the capital of Kenya. And what if I were to say to you why don’t you go there? I’ll get you a job and you’re going to work for the Nairobi stock exchange. And he’s like, he didn’t have a passport. He’s like, ”What?"

Adam Kaufman: What on earth are we talking about?

Doug Holladay: So I said, “Blake just think about it let me know.” So his father calls me up says, “What was that all about? My son and I, we’re just really confused.” I said, “Well give it a little time.” So the kid calls me a week later says, “Ok I’m in. I’ll go to Nairobi.”

Adam Kaufman: Wow.

Doug Holladay: So he goes to Nairobi and I said, “What this is going to do. Just imagine you come back in your interview and instead of saying I’ve got a finance degree and I’ve just had all these internships. You’re saying I went to Nairobi and I worked for the stock exchange.” What does it say about you? You’re comfortable with risk, you’re a global thinker you want to be a broader, better person. It says all the these things about you.

Adam Kaufman: Very desireable.

Doug Holladay: So he came back in six months, got three offers the first week.

Adam Kaufman: Great advice.

Doug Holladay: It just changed his whole life. So I said to my class I said, “Look everybody’s trying to go through the front door. Let them have it. Go through the window.”

Adam Kaufman: You have this uncanny ability I’ve met so many people who say to me, “Oh yeah. Doug Holladay is one of my best friends.” So they all think you are really close and you are close with people. But I have a feeling that if you said who your best friends are and I’m not going to ask you that it wouldn’t be the people who all tell me that they’re so close with you. You have this uncanny ability to make people feel so important. Where do you think that comes from? And it even includes homeless people. You mentioned Jesus and the poor. You taught me to look in their eyes even if you’re not giving the money. Look in their eyes. Ask their name. Where does this come from? Did someone teach you all of this?

Doug Holladay: I had a great mentor Chuck Reinhold.

Adam Kaufman: Who was Chuck? Was he a business colleague?

Doug Holladay: No, Chuck was a he was a guy— I grew up in an atheist family. Which was kind of interesting. I’ve never met anybody like that but my father grew up in a small town in Mississippi got turned off with… He was a very bright guy and asked a lot of questions and this little town didn’t want anybody to do that. So he kind of felt you know that that wasn’t appropriate. So he always was on a journey trying to figure out… So he kind of decided faith wasn’t for him. So we grew up basically unchurched and you know didn’t have any affiliation. But Chuck came into my life who was unlike anybody I ever met. He was a phenomenal athlete and I love sports and he built trust, won the right to be heard.

Adam Kaufman: How did you meet Chuck?

Doug Holladay: It was in my high school.

Adam Kaufman: Ok.

Doug Holladay: He would come to athletic practices and build trust. For a year he just did that and became friends. We’d play basketball, we’d do all these things. And then through that he started asking me questions about what I believed and what I wanted. And through that I discovered a simple faith. And that’s been fantastic. So one of things I feel like when I approach faith and I have atheist friends, Muslim friends, I have everything.

Adam Kaufman: Right.

Doug Holladay: But I bring the eye of a skeptic from my father which I really like. And the eye of a simple follower. So it’s a really interesting combination.

Adam Kaufman: Two different lenses.

Doug Holladay: I hate hypocrisy. So you say how do you develop closeness with somebody? I’d say it’s real simple. Our point of identity with people is not our strength but our weakness.

Adam Kaufman: Absolutely.

Doug Holladay: So there’s always somebody richer, smarter, better looking, more accomplished. So if you try to go through that door, it’s crowded.

Adam Kaufman: And there’s always someone with a higher accomplishment level.

Doug Holladay: I’m with these people all the time that have so much and they’re just freaking out like, “This guy’s got so much more than me.” But if you come in on the basis of your brokenness that’s the point of identity that really…

Adam Kaufman: Ironically that draws people in. I remember one time you were encouraging me along this line of thinking. I was drinking the Kool-Aid early on in the Doug Holladay life and we were in New York City which is intimidating for me to begin with. And you ask everyone at the table to tell something interesting for the group about yourself and none of us knew each other we all only knew you. And this was a little story I want to share with you for a minute because it’s really impacted me. So person number one, these others really weren’t drinking the Kool-Aid they hadn’t been around you so they were doing like the more typical accomplishment comment.

Doug Holladay: Right right.

Adam Kaufman: Person number one said, “I’ve been a Wall Street Journal editor for 30 years.” And I was like whoa I’ve read it for 30 years. Person number two said with an elegant accent, “My family owns more South African apartments than any other family.” l was like oh my gosh. Person number said they went to Oxford with you and on and on and on and I went last of course and I’m like, “What am I going to say to this group?” And it was a moment where I had to decide if I’m really going to try this lead with my worries, lead with my perceived weaknesses, because there was nothing I could brag about to this group. So I said, “Hi my name is Adam. I live in Cleveland.” And that was the first oddity they kind of turned their heads like I was a cute animal. “Oh how cute, Cleveland.” And I said, “Hi my name is Adam. My first wife left me and my father was an alcoholic.” And that’s all that I said. Both are true. And I became the most interesting person at the table. The point is like your theory is accurate. It’s so true. People would then really confide in me. “Oh my sister struggles with drug abuse.” Or, “Oh this is my second marriage.” So I really commend you for this unusual thinking it really does work.

Doug Holladay: Well and you know social scientists have put a label on this that there’s this imposter syndrome. We all feel like, whether we have a dream about this or, somebody is going to knock on our office door and say, “You know you are a total fraud.” And everybody I know I don’t care who they are.

Adam Kaufman: Right.

Doug Holladay: They feel like they were lucky.

Adam Kaufman: Don’t deserve to be there.

Doug Holladay: Yeah. And I feel like the antidote to that is not trying to be something you aren’t. But being really comfortable in your own skin. And I think people are so drawn to that. There was a writer, a Canadian writer, who wrote a book called The Wounded Healer and I love that. We’re all wounded.

Adam Kaufman: Yes.

Doug Holladay: But we can be healers because our wounds are the very doorway into really connecting with people in profound ways.

Adam Kaufman: This reminds me of another way you connect with people. It’s so impressive. I try to emulate it. One week I was with you in Washington and in the same week we met a former governor who had a very public fall from grace and then you also introduced me to a Kennedy family member who also had some embarrassing public news that he had to deal with. And they both embraced you in separate settings like you were their best friend. And I asked you later, “How on earth do you know these people Doug?” And you taught me to reach out to people not when they’re like the most popular person in the room but when they don’t get their phone calls answered. Where do you even come up with a theory to do that or is it just natural to you? I mean it’s really— It’s unusual. And you may think it’s no big deal but it’s very unusual.

Doug Holladay: Well I think it comes back to really knowing yourself and knowing that your own weaknesses and so when I see people like that governor and they’re getting very sanctimonious I said, “Look we’re all wounded we’ve all made mistakes. We’ve all not measured up to what our hopes are.” And once you start understanding that then it becomes easier you know you aren’t judgemental.

Adam Kaufman: Almost like a common denominator, a common denominator that equalizes us.

Doug Holladay: Exactly. And so you know I’m going up to New York today and I’ve got this group I started it with. We started 30 years ago with John Whitehead and I the legendary head of Goldman Sachs when we were at the State Department together and you know we started it. We have the top financial and CEOs in America.

Adam Kaufman: Just a little men’s group that meets?

Doug Holladay: Yeah that meets the second Wednesday of every month.

Adam Kaufman: You’ve been doing this for over 20 years.

Doug Holladay: Oh yeah. I think we started in ’90.

Adam Kaufman: Remarkable.

Doug Holladay: So it’s great. It’s such a wonderful atmosphere because everybody in there is so accomplished but nobody talks about it. It’s all about brokenness. And we’ll read an article like David Brooks’s article on the difference between your resumé and your eulogy and it gets them talking about, “I’ve got a great resumé but what are people going to remember me for?”

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 U.S. 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 embrace the idea of partnering with Bobby George and TownHall to learn more about what they’re up to you can visit townhallohiocity.com. Right now I’d like to take a moment to talk to you about Calfee, Halter & Griswold, a full service corporate law firm with attorneys throughout Ohio and in Washington D.C. Calfee’s mission has been to provide meaningful legal and business counsel to entrepreneurs and investors, private business owners and nonprofits, public corporations. I’ve referred many successful entrepreneurs and investors to Clfee knowing how well they’d be taken care of and it’s for those reasons that I would encourage you to visit their Web site. Calfee.com. That’s C A L F E E dot com. Thank you very much to Calfee.

Adam Kaufman: So you’ve now written a big new document, your book. And probably a lot of that will feed into your legacy, what people think of you as in the meaning that you’ve given others.

Doug Holladay: Yeah.

Adam Kaufman: I know you don’t think about it because you’re so humble but you often articulate…

Doug Holladay: Well I know myself and I know that I’m nothing special and I just feel like I’m trying to be honest as you can about yourself is framed for others and that’s what I hope to do in the book. And it was tricky, the book, because I’ve had the privilege— You know it’s like in that Hamilton there’s a song in there, “The Room Where it Happens.” The crazy thing is for whatever reason I’ve been in the room for a lot of amazing things. That privilege is something I don’t take lightly. I remember one time when I was on the White House staff. I was working for Jim Baker who was chief of staff who became Secretary of State and Treasury and I was in the room with President Reagan, him, Ed Meese and Mike Deaver. This was the troika around him.

Adam Kaufman: Wow, Reagan’s top advisers.

Doug Holladay: Yeah. And I was in there I think I must have been a note taker because I was a young guy and I’m in there, and it was astonishing perspective. So we’re there and you know how you’re with all your buddies and these three guys every time— They were talking about who was going to run the second term against Reagan and they would say certain people and of course this is their good friend and they want to say you could kill anyone. This guy’s a loser you could kill him. I think I counted six times every time they did this to this one particular individual Reagan stopped them and said that family has suffered so much. And I walked back to my office saying I want to be like that.

Adam Kaufman: There’s no media in the room.

Doug Holladay: No media in the room. It’s never been written about. It was just the privilege I had to witness what character is all about.

Adam Kaufman: And I feel like I’ve witnessed you delivering similar types of lessons without any media around. I know you even gave your mobile phone number to a homeless person who calls you somewhat regularly. I mean what on earth inspired you to do that? And you have a real relationship with Dr. So-and-So.

Doug Holladay: Yeah. You know at first for years I felt like I was in his life to fix him and then I realized you know there are people in our life just to teach us how insignificant we are. And I think I got insight from a guy this guy named Henri Nouwen who had been a priest and was professor at Harvard and Yale and then he decided to spend the rest of his life with mentally and physically disabled people in a community called L’Arche Community started by a Frenchman named Jean Vanier.

Adam Kaufman: This in the US he was doing this?

Doug Holladay: He was doing this in Canada but this movement is spread all over a large community. And what he would do Adam, he was a very well-known speaker. But now when he speaks well I think he’s died recently. But he would take one of these mentally and physically disabled people with him and they’d stand up front in the middle of him talking. This person would interrupt him, do all this kind of thing. And he said, “You know I really used to think I was significant because I was teaching at the top two of the top universities in the world. Now I realize how that’s so unimportant and what I’m doing here standing here with this good friend…” And I probably can’t get three sentences before he just says something so inappropriate but wonderful. So I feel like this guy that—

Adam Kaufman: In your life.

Doug Holladay: Yeah. He’s so good for me because first I was humiliated by him and then got to the point where I took him— He came to every Christmas, every Thanksgiving with me and I love people seeing people’s reaction because I could gauge a lot about who they are.

Adam Kaufman: I’ve been with you and you had one phone call coming in from the chairman of Bear Stearns in the next phone call was from this homeless Doctor we’re talking about.

Doug Holladay: Yeah.

Adam Kaufman: And you treat him equally and in fact probably even a little more excited when the second call came in if we’re being truthful. You’ve done so many different things professionally Doug in terms of working for the United States as an ambassador, Wall Street private sector, more investment related work. What work has given you the most meaning in your life? I love how you talk about meaning so much.

Doug Holladay: You know it’s funny I feel like meaning finds you. And I think the problem is most people keep trying to punch their ticket so that someday they’ll have a life of consequence. And I have viewed it differently. I am going to try to be who I am and if it doesn’t work, it doesn’t work. So I remember when I was at Goldman Sachs when somebody said, “What was your proudest achievement?” I think it was that everybody on the management committee asked me to spend time with their sons.

Adam Kaufman: That’s interesting.

Doug Holladay: And I thought, they probably didn’t even know why they were doing it. But we had had really good conversations. And you know so many of them because of some of the things we’ve talked about they love their son but they didn’t know how to connect. And so I felt like that was why I was there.

Adam Kaufman: That is an ultimate compliment if you could spend time with somebody’s child. If help somebody’s child.

Doug Holladay: Yeah absolutely.

Adam Kaufman: Brilliant.

Doug Holladay: Oh yeah. And it can’t be for an ulterior motive. I think it’s gotta be that that’s truly who you are and why it matters.

Adam Kaufman: Of course.

Doug Holladay: Because I think the tendency is— You know I read this thing once, men and women are looking for better programs when the real need is for better people. A program’s not going to change a life. It’s a life on a life that’s going to change it.

Adam Kaufman: I am in airports a lot like you are and the bookstores and the airports there are so many different books about happiness and the pursuit of happiness in different forms. Whether it’s fitness happiness, or beauty happiness, financial happiness. Meaning, capital M, is your favorite word. Why do you think Americans spend so much time pursuing happiness and not meaning? Like where did we get that wrong?

Doug Holladay: Yeah I remember I had a big to do a couple of weeks ago with my editor about this. He wanted to put happiness in the subtitle.

Adam Kaufman: Oh my gosh we don’t need another happiness book.

Doug Holladay: And I said to him I said, “I am frankly opposed to happiness.” And he said, “Really? What do you mean?” I said, “So let me let me break this down for happiness is really related to actions. I have a good date, I have a good bank account, I’m accomplished. It’s all about exteriors. Meaning is something far deeper.” And if you doubt me on that you look at Viktor Frankl’s book which I reccommend to everybody, “Man’s Search for Meaning” written by a psychotherapist in the death camps and as he was there he noticed the people that survived were not the people who are the physically more robust but people who had a deeper meaning structure in their life.

Adam Kaufman: Purpose.

Doug Holladay: I’m a violinist someday I’m going to go and play that violin that’s my meaning I’m going to go back and try to find my grandchildren who left Germany before you know they’re alive. So they had something much more profound. They were living for.

Adam Kaufman: The happiness is fleeting.

Doug Holladay: Oh it’s fleeting and meaning and joy. You know C.S. Lewis unpacks this and he says it a little different. He talks about joy that joy is something so deep and you can have joy even on your deathbed because it’s not tied to how you look or how you feel or any of this. It’s a profound thing.

Adam Kaufman: Did your editor listen to you? Did you convince him?

Doug Holladay: Yes we have meaning in there instead of happiness.

Adam Kaufman: So one of the questions I often ask guests on the Up2 podcast, is if you could go back and talk to the 21 year old version of yourself what advice would you give the younger version of you? You by virtue of having a classroom where you have a lot of young people in the room. You can actually implement maybe some of the lessons you’ve learned from your own walk in life.

Doug Holladay: Well as you know in my [class], 50 percent of their grade is writing a paper that’s informed by the readings, the class discussions, the guest speakers. And it’s different. It’s them. They’re usually about average age 30 in my MBA class, highly accomplished. I said, “So the 25 year old you is writing to you now What are they saying to you to pay attention to?” So that’s their paper. I said, “This is going to be your map for your life and it’s going to be informed by all these amazing readings and all these amazing people who have come in.”

Adam Kaufman: You bring in guest lecturers from all walks of life?

Doug Holladay: Well and they think they’re going to lecture. I said I don’t want to lecture. I want you to talk honestly about how you got through the difficult times. How do you find meaning in the middle of things.

Adam Kaufman: And this is in business school I’ll remind the audience. This isn’t in like some theoretical religious philosophical program.

Doug Holladay: It’s not in a school theology or philosophy department it’s in the belly of the beast.

Adam Kaufman: And you wouldn’t say this but isn’t it the most requested class? They have a points system to bid on classes.

Doug Holladay: It’s pretty popular.

Adam Kaufman: That’s awesome. How many years have you been doing it?

Doug Holladay: I think is my fifth now.

Adam Kaufman: And Georgetown is one of the highest ranked business schools in America every year.

Doug Holladay: It’s been an honor. They’ve been so good to me to let me do that. I out of all the politics all I do is love the kids. I love the Dean you know I love everybody I meet there but my whole goal is just to change lives.

Adam Kaufman: I won’t let you avoid the question if you could go back to the 21 year old version of you. Is there anything you would tell your younger self?

Doug Holladay: You know I think about this and I would slightly rephrase the question. It’s almost like somebody that’s a good athlete, a natural athlete but doesn’t push themselves to go the full level. I feel like in my life I’ve been out to do pretty well because of my natural gifts. But I feel like a regret would be that I probably was afraid to be all in on some things because maybe that wouldn’t work. It’s almost like the athlete that says you know if I’d really worked hard I could have made the NBA. But you know because I didn’t.

Adam Kaufman: See that’s remarkable. This is your humble self coming off because others would say, “He has made it. He has been an ambassador and worked at the White House and Goldman Sachs etc.” You feel like you didn’t, early on at least, go full throttle.

Doug Holladay: I think all these things were great but probably I left some things on the table. You know everybody’s got to go you know to whom much is given much is required.

Adam Kaufman: Absolutely.

Doug Holladay: And you think about how everybody has their own capacity and we’re supposed to be for others.

Adam Kaufman: But you’re getting an A in life you pulled out the Walker Percy quote early. Yeah but you would give yourself an A I hope for living a full life.

Doug Holladay: All I’ll say is I am utterly grateful Adam for this life. I’ve made mistakes, all kind of things but amazing and just to see the kind of relationships I’ve been able to have and the people that somehow feel like I’ve been valuable to them in some small way.

Adam Kaufman: So many of those people. Any learnings from any of those mistakes you want to share?

Doug Holladay: I think we all need to be better at forgiving and forgive ourselves and forgive others. I mean I love the story Abraham Lincoln told you you know. There was withering criticism against Lincoln. They said you were an Eastern educated member in those days it was like Harvard or Yale. All these things. You came out of these privileged backgrounds and here’s a guy that was home you know self educated lived in a log cab and the whole thing. He was gangly and not attractive.

Adam Kaufman: He probably felt like the imposter too the imposter syndrome.

Doug Holladay: But I love what he said. So they’re in this equivalent of press conference and they said, “President Lincoln, how do you get up in the morning when you get so much criticism?” And he only pauses and said, “I’m so much worse than they could ever know.”

Adam Kaufman: What a refreshing and candid thing to say.

Doug Holladay: And I think of that when I start getting pissy about you know this person criticizing me. I said, “I’m so much worse.”

Adam Kaufman: If they only knew. That’s good.

Doug Holladay: And once you kind of accept that you’re flawed and you’re not that hot. Oh my gosh it’s so freeing.

Adam Kaufman: Do you ever think about, you’ve mentioned several historical figures, other influential people in your life either famous or not famous people you know or don’t know? Any big influences on you?

Doug Holladay: Oh boy there’s so many of them, there’s so many of them.

Adam Kaufman: Didn’t you write a paper on William Wilberforce?

Doug Holladay: Yeah. And now historically Wilberforce would be my historical model.

Adam Kaufman: He was a lawmaker in England, right?

Doug Holladay: The lawmaker who abolished slavery it took him forty seven years. So in his 20s he wrote in his diaries that God Almighty is put before me two things the reformation of manners which was the moral climate of England and the release of the slaves. And he spent forty seven years on that I mean we’d all love that. And he died three weeks after in 1833, Parliament abolished slavery. I mean that’s like…

Adam Kaufman: His life’s work.

Doug Holladay: Yeah his life’s work. I mean I say to people so the the thing you can get frustrated because most of us don’t have the privilege of knowing at 22, I get it. He seemed to know it. He gave up— Probably could have been prime minister his best friend was William Pitt who was the youngest prime minister in England ever at 22. But instead of going there he just said I’m going to be an independent I’m going to galvanize and he changed the world. He knew that some people were moved by the sheer inhumanity of slavery but others had real vested interests.

Adam Kaufman: As an industry.

Doug Holladay: Yeah an industry. This was the equivalent to the defense industry in America everybody was connected in some way to slave trade.

Adam Kaufman: Capitalizing on the slave trade.

Doug Holladay: So he cut an economic deal. The government paid the equivalent of 50 percent of the market value of a slave.

Adam Kaufman: To the slave owner.

Doug Holladay: To the slave owner, yeah. So that they wouldn’t be bankrupt and send the country into a terrible recession.

Adam Kaufman: I can tell talking to you for our listeners here you’re excited. Your posture changes. What gives you the most excitement right now as you think about the future? What are you really excited about?

Doug Holladay: I love what we’re doing at PathNorth because…

Adam Kaufman: PathNorth is a D.C. based nonprofit.

Doug Holladay: Yeah D.C. based nonprofit where I started it with a bunch of leaders maybe nine years ago and the whole purpose was to create a safe context where people could explore the most important things in life. So that’s been fun to see them open up.

Adam Kaufman: What types of things do you do in PathNorth to get them to open up?

Doug Holladay: We take trips, short trips, have dinners, have experiences that force people out of their comfort zone to get them really considering life from a different angle. And I think that’s what changes them. As you know we went to England that time. We didn’t tell him but we took him Dans le Noir which was a restaurant that in French that means “in the dark.” So we take him into this restaurant owned and run by blind people. So we had this high control type people for two hours in pitch black.

Adam Kaufman: Utter darkness, your eyes don’t adjust.

Doug Holladay: Your eyes don’t adjust. With a blind waiter. You don’t know what you’re eating or what you’re doing. And then we talk about. So what’s it like to be denied something so important to you and what did this evoke in you? So these powerful leaders are saying golly that was insecure.

Adam Kaufman: Right that former Secretary of the Navy like touching my knee every 15 minutes just to make sure from a security standpoint that somebody was still right there. The next day we also went to both Wimbledon which in all its opulence is a wonderful place to see a sporting event.

Doug Holladay: Particularly with Stan Smith.

Adam Kaufman: With the Wimbledon champion but then right after that we went to a maximum security prison where inmates served us a meal and then you led a discussion about resilience. What does it mean to be resilient? Is it more like the athlete who overcame his opponent that day or is it more like the waiter who told us he wanted to break three generations of crime in his family and learn how to serve. Amazing that you think of these ways to disrupt people’s minds and hearts a little bit and get them to open up.

Doug Holladay: And we all are more alike then we’re different. And I know some people freaked out when I had said to our waitor, “Why are you in here?” And I know the guy had murdered some people.

Adam Kaufman: Right.

Doug Holladay: And you know it’s like he might have made a bad choice. We didn’t. But you know.

Adam Kaufman: One small decision can lead to a bigger bad decision.

Doug Holladay: But it gets you in touch with your own frailty.

Adam Kaufman: Yes.

Doug Holladay: And once you look at anybody through that lens it really does change you. You know it really does change your life.

Adam Kaufman: Well Doug Holladay you have changed me for the past four years. I’d like to say for the better. And I hope our listeners will be somehow changed through this discussion today so I’m just so grateful you spent some of your valuable time with us. Thank you for being a part of Up2.

Doug Holladay: Thank you. Appreciate it.

Adam Kaufman: Following up on our terrific conversation with Ambassador Doug Holladay there are a couple reference points I wanted to share. 1. He referenced the book The Wounded Healer and that was written by Henri Nouwen a Dutch Catholic priest and a theologian. Secondly Doug also mentioned frankly one of my favorite passages in the New Testament when he talks about “to whom much is given much is expected” and that’s from the Book of Luke Chapter 12 actually. And now my five biggest takeaways from today’s episode with Doug. Number one, it’s not good for men or women to be alone for too long. Bad things happen to people who become isolated. Number two, develop a language to discuss what really matters. For instance, what would your children say is most important to you? Number three, our point of identity with people is not our strengths but rather our weaknesses. Leading with our weakness or our worries draws people closer to us. Number four, don’t underestimate your own capacity to take risks and to challenge yourself. And number five, once we accept that we’re actually flawed and not so brilliant it’s really freeing. Special thank you to all of our listeners to each of you. I’d love to know about a favorite moment or even a favorite episode. You can email me at adam@up2foundation.org. 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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