Asking The Right Questions: The Roadmap To Success With Doug Holladay

You’ll never get the answers you’re looking for if you don’t start asking the right questions. This is true in any aspect of life. Doug Holladay, the Founder and CEO of PathNorth, takes a seat with Dr. Diane Hamilton to talk about the part of curiosity that’s often ignored. In this episode, Doug talks about defining what success is for you, and the consequences that come along with success that you need to prepare for. Learn as well all about the principles of finding the meaning of life as he discusses each of them in detail. Being surrounded by leaders, Doug gives his insight on what a leader should be and why you should focus on becoming a better person if you want to improve as a leader.

TTL 750 | Asking Questions


I’m glad you joined us in this episode because we have Doug Holladay. He is the CEO of PathNorth. He’s also a Georgetown University professor. He’s advised many presidents. He has contributed to a lot of books. He does a lot of articles for The New York Times, Washington Post, and USA Today. You’ve probably seen his work. His book is fascinating. It’s called Rethinking Success. I’m excited to talk to him about it.

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Asking The Right Questions: The Roadmap To Success With Doug Holladay

I am here with Doug Holladay, who is the Founder and CEO of PathNorth. He is a Georgetown University professor and a former White House advisor. He has a book, Rethinking Success. I’m excited to have you here, welcome.  

Thank you, Diane. What a pleasure.

This is going to be fun for me. First of all, I would love to say that I listened to some of the audio versions of your book. I love that you put some of them on YouTube. There are great clips if you want to get little bits and pieces of how you did that. I should have thought of doing that more with some of my work. The way you did it was some high-level points that get people enticed to read more. That was a good idea.

I’m glad that worked. A lot of people don’t have the time or take the time to read. If you can give them a couple of nuggets that enable them to get a little piece of it, then they get excited and maybe read the whole thing.

I alluded to some of your backgrounds, but since you have such an interesting backstory, I want to start with that. Can you give a little bit more background of how you got to this point and what made you interested in writing this book?

In my first chapter, I said, “We’re all born into someone else’s story.” I got that line from Peter Buffett, Warren Buffett’s son, who said, “Here I was at Stanford. I was born into this story that I did not ask to be in. I am majoring in finance, which I didn’t want to, but here I am and I want to be a musician.” I realized that everybody’s story shape so much about their view of life, meaning, family, purpose, success, failure, and everything. In my case, my editor said to me, “Doug, why your whole life, there’s an interesting thing you’ve done? Whether you were at Goldman Sachs, White House, State Department or whatever situation you’ve been in, you’ve always tried to create a safe place where leaders can talk about what matters in life. What is the purpose? What is meaning? Have you ever been curious about why?”

I started thinking about that. I grew up in an atheist family. My father was allegedly an atheist. He grew up in a small town in Mississippi. My dad was curious and he asked a lot of questions. He went to church with his mother. She was religious, but that was not welcomed in that era. He shut down and said, “If religion does not invite curious people or seeking people like me, then that’s not for me.” I grew up in an atmosphere where we prize ideas. The first time I ever heard of Socrates’ quote was from my father when he said, “The unexamined life is not worth living.” I was around ideas all the time, but not around faith. I realized my whole life has been to try to create safe places for leaders like my father, who never had a place to explore. I love people that are curious and interested in finding as Freud called it The Riddle of Life. What is the riddle of life?

[bctt tweet=”Never compare your insides to someone else’s outsides. You never know what’s going on. ” username=””]

I love that since I studied curiosity. My father was not religious either. Did you go in that same direction? Which direction did you go?

I was unchurched, not religious, but then I had a guy that came into my life. I was an athlete in high school and this guy came into my life who was a champion athlete, but he also had faith unlike anything I had ever seen. He was ten years older. He befriended me and became a mentor. He showed me a different version of faith. It was real and fun. It was packed full with meaning and rich relationships. I began at age eighteen a real pursuit of being a follower of Jesus, not a religion. I contrast those two because religion has caused so much damage in the world. It’s both the solution and the problem in the world. I believe being a simple follower with faith is a different thing. I have been on that trajectory for a long time.

I am glad you brought up mentorship because that’s such a huge thing. I’m at this Global Mentor Network, which was a brainchild of Keith Krach, who was the former chairman of DocuSign. He is the Under Secretary in Washington.

He was at one of our PathNorth dinners.

Isn’t he great?

He’s in San Francisco.

He wrote the foreword in my last book on curiosity because I worked with him on the board of advisors at DocuSign. This mentoring thing is going to get a lot of attention. I had David Novak on the show as well who’s the former CEO of Yum! Foods. He’s got something similar in terms of a mentorship site. I think you’re going to see a lot of mentoring coming up because there are many people who can offer so much wisdom. We need to go to some of these people for some of their insights.

You mentioned Peter Buffett and I noticed you talked about how he found out that he wasn’t going to inherit what he thought he was going to inherit. Some of us have things that change our story and narrative. I love that you focus on what we think of things and what they are. My next research is on perception. You talk about illusions to success and I want to get into that. In Rethinking Success, you’re talking about what people feel when we look at them. We think they’re successful, but they may not be inside so thrilled. They can feel isolated, empty, depressed, whatever. What was the point of this book and what are you trying to get across?

TTL 750 | Asking Questions
Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life

Immediately, a thought comes to me of that whole idea, “Never compare your insides to someone else’s outsides. You never know what’s going on.” Part of why I wrote this book is the Hamilton musical has a song on there about being in the room. I’ve had the fortune to be in the room with presidents, Fortune 50 CEOs, prime ministers, and all kinds of people. I come away with one conclusion, the unintended consequences of success, whether it’s notoriety, money or visibility and power is overrated. Most of them are lonely and disconnected. All the data suggest that. There was an Inc. study a few years ago that looked at 3,000 CEOs. Of the 3,000, over half self-reported they were lonely. Of that half, 67% said they were making bad decisions because they had no one in their life they could trust.

In my mind, that’s a leadership crisis because it seems like such a soft thing that people don’t focus on it. The point is, if you are lonely or depressed, you’re not going to be making good decisions if you have no data points other than yourself. What this pandemic has done is it has caused the myth of certainty and all the things we thought were true and right to come crashing down. People are rethinking and trying to re-imagine, what does it mean to be in a family? What does it mean to have financial security? What does it mean to work with others? What does it mean for the future for my kids? What is happiness? What is success? All that I’m trying to do in this book is turn everything on its head.

I had never wanted to write a book, but I realized that many books were taking people down the wrong road. Instead of telling them how to have meaning, they were suggesting happiness and success, classically defined, which is a bankrupt road. Let me make a simple point here. I am not a big fan of happiness. I’m a happy person, but that comes and goes. Happiness is totally overrated. Happiness is pegged to your net worth, my kid got in college, this and that, all of these externalities. Meaning is something different. It’s what Viktor Frankl observed when he was in the Nazi war camp when he wrote Man’s Search for Meaning. He saw the people that thrive in the midst of god-awful circumstances were not the physically robust, but those who had a deeper purpose.

If you doubt me on that, I always say to people, “Do you have children?” They said, “Yes.” I said, “Is that a happy experience raising children?” The answer is usually, “Yes and no.” If you turn the question upside down like, “Is that a meaningful experience?” They said, “It is the most meaningful in my life.” I would say forget happiness and pursue meaning, but most people don’t know how to do that. That’s what my book is about. It is trying to unlock those knowable ingredients to the stew of meaning. David Brooks of The New York Times is a good friend of mine. He said it a different way. He said, “We should contrast our resume virtues with our eulogy virtues.” We pursue all the merit badges of where I went to school, my position, etc. Nobody cares about those on the deathbed.

I have a great New Yorker cartoon. This guy’s on his deathbed. All these tubes hooked up to him and his family is around him. He looked up and said, “I should have bought more crap.” Nobody’s going to say that. I was asked this question in an interview, “What would you say to the graduates? These kids have no prospects for jobs or anything.” I said, “That’s tough but this is a moment to look at yourself and become a better version of you. Invest in things, meditate and learn to be quiet, find your purpose, learn all these things. When you’re ready, you’re going to be a better version of you. You’re going to bring all that to the workplace, which will be fantastic.”

A lot of guests on the show talk about meditation. Daniel Goleman has been on. I studied a lot of his work for emotional intelligence and he’s got into more mindfulness. I think we’re going to hear a lot more about that. When you were talking about meaning, I know some people have had issues with the movie Life is Beautiful, but that came to mind with Roberto Benigni trying to get through the worst possible situation for the sake of his child. As you were talking about these things, I’m thinking about how people put a certain face on. I’ve had a lot of people talk about this imposter syndrome. That feeling like they’re seen in a certain way and they have to live up to this. There are many leaders that are afraid of being seen for some other thing than they are. We don’t have all the answers. One of the reasons I liked Keith Krach is that he would admit, “I don’t know this and I hire people who know these things.” Do you think that a lot of these leaders know as much as people think they know? What are they trying to portray as compared to what they are?

It’s tragic that we have told a leadership class that they need to be perfect people. People don’t want leaders, political or business, to be perfect. They want authentic leaders. They want people that are real. People that tell you the truth and aren’t afraid to admit their limitations. That’s the problem we have nowadays. People try to project, whether it’s in the political, culture or business that they are in control and they have it all together. It doesn’t stand the straight-face test. As a result, we have many leaders that lie continually and no one trusts them. What do we need for this time? I believe we need people that can lead from a point of brokenness.

[bctt tweet=”Forget happiness. Pursue meaning.” username=””]

I always say to my MBA class, “Your point of identity with others is not how smart you are, how gifted, or how wealthy you are. There’s always somebody smarter, faster, better looking or more accomplished. Your point of a day with everybody is your brokenness, that we all are broken. If you lead from that position, you will thrive.” I had a kid in my class I’ll never forget. I had mentioned that on the first day of class. This was the first ten minutes. This guy said, “Professor, I’ve been trying to get in this class for a long time. I’m going to be all-in here. I’m going to take a risk.” I said, “Go ahead, Clark.” He said, “I have had a debilitating stutter my whole life which caused me to live in the shadows. I never felt accepted. I never had any friends. I was always alone. I was strong academically. Here I am, a sophomore at an Ivy League school, alone and depressed.”

He’s telling us this the first five minutes. He said, “I decided I’m going to take my life, but before I do, I’m going to go out and try to have conversations with people. They’re going to laugh at me and that’s okay because I’m going to be dead tonight. Two things happened as I went out and engaged. Number one, the more I told them how insecure I was and how I couldn’t put a sentence together, the more they felt connected to me. They told me their vulnerable parts. The other thing is my stutter started to lessen because I started learning to talk.” He then paused almost for dramatic effects. “Guess what else professor?” I said, “What, Clark?” He said, “I’m the student body president of my MBA class here at Georgetown. I have to give speeches all the time.”

I would be the smart ass that I am. I paused and said, “You’re a class of winners. Clark has revealed some things and you all probably want to transfer out of this class. During the break, you can go to the Registrar’s Office, get into another class because you clearly don’t want to be with a person like Clark. How many of you want to transfer out?” No one raised their hands. I said, “How many of you feel safer because of what Clark shared?” Everybody raised their hands. I said, “If you remember this one lesson, you will be a leader that will be a transformational leader because we’re all broken and we want to have believable leaders, not perfect leaders.”

As you tell that story, I was thinking about how you’ve advised several presidents. I’m comparing that insecurity and that stuttering student story versus presidents. Have you found that they had insecurities when you talk to them? I imagine everybody does, but I’m curious, were they more or less secure than you expected? How was that?

I started at a young age. I was around many leaders that I’m not surprised. These things, in one sense, don’t improve. We develop more sophisticated ways to cover our insecurities, but it’s incredible to me how people still can revert to that fourth grader that doesn’t know if they belong. They feel awkward. I’ve been in rooms with presidents. I’ll never forget this one. We are at the Oval Office with the President. After the meeting was over, the President said to one of the senior advisors, “What do I do?” He said, “You’re the President. You can do anything you want.” He clearly didn’t know where he’s supposed to go. It was awkward, but then it was funny.

That’s why if you try to project this thing and try to be presidential or be a CEO, you’re in for a lonely ride because it’s not sustainable. We all know on some level that we are fraud. You mentioned imposter syndrome. We all feel that there’s going to be a knock on the door and say, “You’re not smart enough. You’re not good enough. You’re not accomplished enough to be in this position.” None of us are. The people thrive despite their limitations.

Isn’t it good to surround yourself with people who are smarter and better, otherwise, how can you grow?

TTL 750 | Asking Questions
Asking Questions: We stop being curious because our education system is all about answers. It’s not about questions.


You’re right. A leader like that, you’re nailing the most important thing. If you accept your limitations, your broken parts, and your failures, there’s humility. One fourth century monk asked, “What is the most ingredient to becoming a whole and fulfilled person?” He said, “Four words, humility, humility, humility, and humility.” You realized, when you’re humble, you don’t mind having people around you who are more talented. I remember Ronald Reagan, this was a shock to people. People forget this. When he was vying to be president, the guy he was vying against was George Bush. George Bush looked like he was going to beat Reagan, but he didn’t.

The guy that was masterminding Bush’s campaign was James A. Baker who became my boss, who became the Chief of Staff, Secretary of the Treasury, and Secretary of State. He is an iconic leader. He was one of the giant leaders of our time. Reagan picked him to be his Chief of Staff. That was unprecedented. In a sense, he reached out to his enemy and said, “This is the most talented guy in the room. I need him.” I think Reagan’s other cronies, Ed Meese and Mike Deaver were like, “That’s shocking. This guy is going to be my boss and he was trying to defeat us.” That’s what good leaders do. They’re not threatened by talents.

It’s a challenging time because what we see in leadership is changing so much. I was listening to part of your book where you were saying, “They have this sense of the golden handcuffs that they’re locked into what they do.” You then have people who say, “Do what you do. Do what you love and you’ll never work a day. You’ll make money if you do what you love.” A lot of people are doing what they love but they’re not making money. How do you get away from the golden handcuffs and still make money enough to make you somewhat comfortable with your life? That’s a hard one, isn’t it?  

It is and it isn’t. I finished speaking to my MBA class. One of the things I do there was I draw a circle and said, “The first circle is, what are the things you love doing when you were small? How many of you wrote poetry, played the piano, played the sport, danced or tap-danced?” They started yelling at all of these things that made them come alive like juggle and everything. Everyone in the class had 2 or 3 things. I said, “How many of you still do it?” One out of forty. Why did we stop when we know those things feed us, when we know writing poetry feed us? Part of it is we live in a celebrity culture where if I sing or play the guitar, I have to be as good as Jimi Hendrix.

I said in my class, “Why don’t you do these things you love? You don’t have to be the best in the world to do it. Just do the things you love.” If you’re lucky, you might get paid for playing the guitar. It’s not a sure thing. I love the story of Philip Glass, one of the greatest modern composers. One day in New York City, there was a knock on the door. The art critic of New York City was there. A guy came in to fix her dishwasher. All of a sudden, the woman looks at this guy and said, “Did anybody ever told you, you look like Philip Glass, the composer?” He said, “I am Philip Glass, but I’m Philip Glass, the plumber, but I also composed.” She said, “You’re the greatest modern-day composer.” He said, “I love doing this. I did this before I was famous.”

My point, if you look at people, Kurt Vonnegut sold used cars. All these people did other things so why did we stop doing the things we love? Grisham lives in Charlottesville, Virginia. He was a lawyer until he was about 55 before he became famous. He would get up at 4:00 AM and write his books and he’d go and practice laws. All of a sudden, he became famous. The point is, why don’t we do the things we love? We stopped doing them because somebody told us, “If you love to make wine, you’ve got to be Mondavi. You’ve got to be some famous winemaker.” Why can’t we love this thing? That’s my point. Any wonder we become empty and vacuous because all of a sudden, work dominates everything we do. We hate our lives and all the things we love we’ve left behind. If you used to love tap dance, put on the shoes and start tap dancing. You don’t have to be famous. You can do it because of the sheer love of doing it.

That’s true. I wanted to address what you said because you mentioned someone told us and that impacted us. In my research and curiosity, I found the four things that hold us back from curiosity are fear, assumptions, technology and our environment. The assumption is that voice in our head saying we have to be the best or we have to be Ginger Rogers to tap dance or whatever it is we tell ourselves. A lot of that is influenced by our environment and someone told us, and that influences our curiosity. I was surprised that there wasn’t any research on what held us back from being curious. That’s why I’ve been researching that for years. It fascinates me to study behaviors, behavioral change, and what it takes for us to move forward. You said it takes a crisis for behavioral change. I thought that was interesting. Why is that?

[bctt tweet=”We want to have believable leaders, not perfect leaders.” username=””]

A crisis forces you to look at what matters most. When I’m going through something difficult, I don’t have to have time to think, pray or reflect on our lives. I got it because everything’s stopped. It’s almost slow motion. One of the people I love is Father Richard Rohr. He is a Franciscan monk. He said, “The only two things that changes our great crisis are great love.” That’s true. It’s like Rahm Emanuel when he was the Chief of Staff said, “A crisis is a horrible thing to waste.” When you’re going through a difficult time, divorce, death or depression, this is the time to go deeper, to start to think about what matters and to reset. The problem with most of us is we get busier.

I take a bunch of CEOs every year to a silent retreat in a monastery for three days where the monks chant. We are together but we don’t talk for three days. It’s transformative. I give them a journal. In 1666, Blaise Pascal wrote a book called Pensées. It means thought in French. It’s incomplete. In there, he said, “The fundamental problem of a person is never learning to be alone within four walls.” The problem with most of us, we are terrified to be alone. We spend all of our time with technology, things and people. We’re feeding that fear that if I’m alone, I’ll be terrified. All of a sudden, when these people and leaders get time, it’s hard at certain points, but they emerged different. They are more settled, at peace, grounded and able to see what truly matters. A part of the journey is doing all these counterintuitive things. Stop searching and start asking questions. Research shows when a kid is about six years old, they ask about 400 questions a day. When they’re 45, they ask about three. Why did we stop asking questions? Why did we stop being curious? Because our education system is all about answers. It’s not about questions.

It’s all about memorizing and it is terrible. I have a terrible memory and I did not enjoy being in school that much. It’s amazing to me that I ended up with a PhD because I did not like that part of it but I love learning. I want people to love the sense of learning. What I loved about your book is that you ask a lot of questions. You say there are eight essential practices for finding meaning in work and life. We have to ask ourselves these eight essential questions. Can we touch on those?

They’re simple but profound. I’ll run through a couple of them here. They’ve said this to me, “Doug, how do I start?” I’d say, “One, look at your story. If you came from a raging angry family, there’s a pretty good chance that you’re going to emulate that, because what we see is what we emulate.” I read this book by an eminent psychiatrist at Johns Hopkins University in Texas. All the things we teach our kids about how to live, what success is, all these little detail things, all the advice we give them all the time, none of that matters at all. There’s one thing that matters, it’s the way we live.

Modeling is the most important thing. We need to go back and understand our story and what shaped our view of everything. You understand that when you look at your family. You can then pivot and say, “Is that a version of success? Is that the view of the family I want? Is that how angry I want to be? Do I want to be a grievance person that never forgives? You’re going to emulate what you’re saying and experience even if it’s wrong. The second thing I’d say, develop real relationships. People start shedding relationships. The data suggest that at age 30 to 45, you go from all the people you thought were your friends to maybe 1 or 2 when you’re 45, and people get lonely. I say invest in people.

I don’t let my class even use the term networking because that reduces the relationship to commodities. We need people in our life that we trust, value, and invest in. That is important. The other is to make gratitude a practice. Neuroscientists tell us that you don’t have to make a list of the horrible things that have gone in your life. Those are the things why we wake at 3:00 and say, “What am I going to do about this?” If we do it every day or seek to do it a couple of times a week, and write 2 or 3 small things, this changes the brain. We become better versions of ourselves. The other is forgiving. Not forgiving is like me drinking poison and expecting you to die. It’s stupid and it doesn’t work. Let go. It doesn’t mean you condone people. You’re just not empowering them to destroy your life.

The other is serving, laying your life down and looking for little ways to make people’s lives better and richer. Find your definition of success. I have a good friend, one of my best friends whose son is an MBA from Yale. What is he doing? He’s at home raising the children while his talented wife is the general counsel of a big health insurance company. This was hard for him and then we kept talking. He’s found the model of success that worked for him. The younger generation is doing that. They’re freer to imagine success on their own terms.

TTL 750 | Asking Questions
Asking Questions: Don’t look for answers. Love the questions, and if you’re fortunate, you’ll find your way by asking the right questions into the answer.


The other is to invite risk into your life. This palliative nurse, Bronnie Ware, who was with thousands of people in the last hour of their death. She observed an interesting thing, the greatest regret older people had was they stopped risking. I say to people, “Take little risks every day and push yourself.” You don’t have to go bungee jumping, but do little things. When you see a homeless person, instead of throwing them a dollar, ask their name. It will change the experience. Two last things are living an integrated life. Try to make everything a part of your life. Always working and playing. Bring joyfulness to everything you do in a curious and imaginative approach. I don’t feel like I’m ever working. I love creating and doing. It’s seamless for me. I want to live that way.

Lastly is legacy. What do you want to leave behind? We spend our life pursuing merit badges. What kind of person do we want to be and be remembered? It’s never too late to change our story and our legacy. I’ll leave you with one story. Everybody remembers this great story of Mark Twain who woke up about 1900 in London. He opened the paper, The London Times, and it said, “The great writer Mark Twain has died.” He famously quipped, “The rumors of my death are highly exaggerated.” At the same time, there was another man that experienced the same thing. His name was Alfred Nobel. He was in Paris and he picked up the paper and the front page said, “The merchant of death is dead.” The Nobel family had invented dynamite, which enabled epic killing on levels that no one could ever imagine in terms of the World Wars. What was interesting was he had not died, but his brother in Southern France had died. Alfred was troubled by this that he decided to change his legacy. We know the Nobel Peace Prize came out of that. The legacy of the Nobel family is not dynamite, it’s rewarding the best, brightest and the most imaginative leaders that have existed in the world.

Those are all great stories and I’m thinking, you must tell a lot of these in the courses you teach at Georgetown. You have one of the most popular MBA courses. What’s the name of the course that you teach?  

The name of the MBA course is The Life of Work, Calling, Bringing Meaning and Contribution For Business in Life.

Is this something that’s focused on behaviors? Is it psychology? I’m thinking I’ve had Albert Bandura on the show. Is it a cognitive thing?  

If somebody reads the books, they would say there’s philosophy, theology, humanities, business practices and storytelling in this. I try to tap into all these rich minefields of truth and try to bring them together in one place. There are many teachers coming at us from lots of different directions, but I find the ancients have a lot to teach us. There’s wisdom that’s there for us to tap.

Who are some of the great minds that you teach in that course?

[bctt tweet=”When you’re humble, you don’t mind having people around you who are more talented.” username=””]

I mentioned Aristotle and Socrates. I looked at the Book of Proverbs, which is amazing when I talk about relationships. I quote Ecclesiastes 4:9-10. This was written 3,000 years ago and it says, “Two are better than one for they have a good reward for their toil. If one falls, the other will lift them up, but woe to him who is alone when he falls as not another to lift him up.” That is as true nowadays as it was 3,000 years ago. I then look at Sartre, Camus, and a lot of the existential writers. I tap into a lot of great poets. Rilke, this German poet said, “Don’t look for answers, love the question that if you’re fortunate, you’ll find your way by asking the right question into the answer.” In my business, what I do is I say to people, “Let’s not look for the answers. What are the ten questions we need to ask to have the very best answer?”

We’re looking for a lot of answers with COVID. How are you addressing that in your class? Are there a lot of people wanting to talk about that?

Yes and no. We adjust to the new normal quickly in life. People say, “This is the context I meant.” They feel insecure. I always say to them, “Control what you can control.” It’s a great Saint Francis quote that I have in my house. It says, “Change what you can change. Accept what you can change and have the wisdom to know the difference.” What we need to do, I don’t care if it’s diseases or others, is for all of us to say, “What is within my span of control?” Work on that. What is within our span of control a lot now is the internal jury, not the external. This is the time to look within. There’s so much wisdom that we get from that. These ingredients that are thriving are knowable. We’ve always known them. Jesus talked about the importance of risks. He tells some great stories about that, but many times, we don’t have any historical knowledge of these things. We always come into problems thinking, “I’ve got to invest in the answer,” when there’s so much we could tap into.

I’m sure you use a lot of these for PathNorth. I also mentioned that you were the Founder and CEO of PathNorth in addition to teaching at Georgetown. Tell me a little bit about what you do there.

During the 2008 financial crisis, I saw many of my friends who were CEOs and investors struggling with their lives and said, “This doesn’t feel good. I want to take my money and go someplace.” I said, “This is terrible. We have to find communities of people that can talk about the pain points. What we don’t know, our questions are longing.” That’s why we started PathNorth. We take trips. We try to get people to talk honestly about their fears and hopes. One of the first trips was on the Orient Express where I changed it a little bit. I took magicians with us. We had a great time. Every night, I asked them in the magic motif two questions. I said, “What are the illusions you had about life? What is a mystery you’re still trying to figure out?” People went deep and they continued that conversation to the day. Nobody had been asked that of a CEO and said, “What are the illusions you have?” “I thought my son would turn out this way, but he didn’t. I thought I would feel more secure and happy.” They gave voice to those demons that they are battling with.

How many people go on these? Are they all CEOs?  

There are small trips. We have one annual private gathering. We had one in Texas before they were locked down in San Antonio. We had about 175 to 200 leaders, but we have smaller trips. We have a trip that we came back from India. We went to Morocco. I took some to Ethiopia and Kenya. We go to have our lives change, not to see fabulous places and meet fabulous people, but how can this experience change us?

TTL 750 | Asking Questions
Asking Questions: Change what you can change except what you can’t change and have the wisdom to know the difference.


What do you talk about? What’s the topic? Is it how to be a better leader?

No. That’s useless to try to be a better leader. Being a better person translates into being a better leader. It’s interesting the success literature of America up to the ‘40s. If you research it, up to the ‘40s, it was all about virtue starting with Ben Franklin, “A penny saved is a penny earned.” It was about you becoming a better person. The 40 things started shifting. It became techniques, smiles, remember names, and project trends. It became all about technique and about who you were. It’s easy to start pivoting toward manipulating others. It is a short journey. My view is to become the best version of you. That’s what people are longing for, authenticity. Whether you’re a great speaker or not as irrelevant, be a real speaker. That’s what a great speaker is.

It’s hard if you try to be somebody else on the stage. It comes through so clearly. I love that you focused on Rethinking Success because it’s unique. I’ve had a lot of people give the how-to’s and all that, but this is a unique topic. You said you didn’t want to write a book or it wasn’t your priority. Are you thinking of writing any more books or is this one your baby?  

I have a lot of things, but I never wanted to write one. Having said that, I do have a couple of others in my mind. The one I would like to do next would be a shorter book. It would be five regrets you’ll have your whole life because there are regrets, if you’re not careful, you’ll go to your grave regretting.

What do you think is the biggest regret that people have?

They never found their true purpose. They went to their grave saying, “There must have been more for me.” They chased the wrong purpose.

Do you think your purpose changes ever?  

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I do. I would say though, our purpose, we need to almost do the work. I say to people, “Do you want to find your purpose? Look at your life in a five-year span starting from 1 to 5, 5 to 10. What did you love to do? What did people say you were good at?” You will clearly identify these markers. It’s unbelievable. There was a girl I remember in my kindergarten class. Judy Rich used to line us up according to height and present us to the teacher. Nobody asked her to do that. If she’s happy, she’s probably an investment banker someplace or an actuary or an accountant because she loved metric. Nobody asked her to love metrics. She loved doing that. You start looking at, “Do I like working with a team? Do I like writing? Do I like thinking? Do I need time alone?”

You start to put all those pieces of the puzzle down, and you start seeing the contours of who you are and what you were made to do. We focus so much on jobs instead of our purpose. I have a purpose and I know what mine is. It shows up whether I’m an ambassador to South Africa or Goldman Sachs. I love bringing people together. I don’t want to necessarily be the CEO, but I liked being an impact player. That’s where I find my meaning. I love helping people become the best versions of themselves, which means being a better leader. I’m not sitting around saying, “Here’s how you’re going to make the numbers better.” I could care less about that. I know the numbers will be better for them and their company if they get grounded and start focusing on the right thing. These things are knowable, but you have to do the work.

What about sacrifice to get what you love to do? Sometimes you have to do some other things in addition to what you love to pay the bills.

If you draw two circles, one circle is, what must I do? I have to pay the bills, the food, the lights, and the rent. You put all of that in. You then have another circle, what is my purpose? What makes me come alive? Most people what they do is they forget about that. They shut that right circle down and they get into this horrible life of survival. If you keep that other thing alive, they start to come together in an almost amazing and magical way.

There are different points in your life. Some jobs that maybe weren’t my favorite jobs when my kids were younger because then it allowed me more time to be with my kids. Do you think younger generations maybe want more instantaneous success?  

You’re absolutely right. This is the point I make in the book. I am totally against a balanced life. It’s impossible to lay. It doesn’t work. There’s nobody who does it. What I think is there are seasons in life. When I was in the White House staff, if you left at 9:30 at night, they would say, “Doug, you’re working a half-day.” If you were doing that for the rest of your life, that would be a problem. You can do that for 2 or 3 years as long as your family understands that this is the game you’re playing. There are seasons when you do that and then there are seasons when you back off and recalculate that.

You’re at the right, Diane. There are points in your life when you get to be all in. There are other times when you got to say, “I’ve got four kids at home. I want to be more present now.” I have a friend who’s a CEO that left and everybody’s shocked. He was running a Fortune 100 company and he decided to step down because he wanted to be with his kids for the last two years of high school. He’s not doing anything and people are bothered by this. “Frank, you’ve got to get another CEO job. You’re going to miss your moments.” He said, “I’m good. I’m loving this.”

It’s such an important thing to focus on some of these things that will make you happy. Success is a word. I love that you’re rethinking it and your book was amazing. A lot of people are going to love it. A lot of people reading this are going to want to know how they can find you or find your book. Are there any social media or websites or anything you’d like to share?  

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They can look up There’s a lot about what we work on there and then there’s a landing page, which has a lot of the interviews that I’ve done in the book and all. That’s at There are all these interviews. There are all of these things there that they can focus on and see what we’re doing. They can get the book on Amazon. It is published by Harper Collins.

I enjoyed it and they can also listen to a couple of excerpts on YouTube. I thought they were good. This was fun, Doug. Thank you for being on the show. I was looking forward to this and I learned so much from you.  

Thanks, Diane. I have enjoyed this and it’s been an honor to talk to you and thanks for all the good work you do.

Thank you.

I would like to thank Doug for being a guest on the show. It was such a great show because his book fascinates me. Success is a term that gets tossed around a lot and we don’t analyze it. It’s like curiosity. It’s a word you use every day and if you start to focus on it and what inhibits it or what we’ve put it on a pedestal to mean, all that is fascinating to me. I know his book addresses a lot of questions that we should be asking. He used the word ‘curiosity’ quite a bit as we chatted. I love that because we need to look at some of the things that are inhibiting curiosity. A couple of the main things he was talking about tied into the factors that I found that I thought was important in terms of assumptions we make and how much our environment impacts us. We do a lot of this assuming that we don’t like something, that it’s not worth doing, other people will make fun of us for doing it, or all these things that can lead us down this path where we don’t explore our natural sense of curiosity. We get stuck into this status quo way of always doing things.

That will lead to regrets later. Within companies, when you have status quo thinking you’re not as innovative and people aren’t as engaged. We’re trying to get away from that. I loved the work Doug’s doing. He’s got a couple of clips from the book on YouTube and they’re worth listening to because it will entice you to want to buy the book. He’s touched on something that a lot of people don’t write about often. That is something we need to discuss because I’ve had a lot of CEOs who have said that same imposter thinking. They’re worried that people are going to see behind the curtain. If we have CEOs who buy into that they have to look perfect, they often don’t embrace this curiosity mindset and they get stuck in status quo thinking.

We know that culture starts at the top. If we don’t emulate what we want to see, we’re not going to see that curiosity. If we have that curiosity, that will help us be more innovative, engaged and productive. Those are some food for thought. I thought that was great. It tied into Doug’s work and everything that he wrote about. I love that he shared that on the show. We get many great guests on the show. If you’ve missed any of the past guests, you can go to to learn more about curiosity and perception and all the assessments that are offered there. I hope you take some time to do that. I hope you enjoyed this episode and I hope you join us for the next episode.

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About Douglas Holladay

TTL 750 | Asking QuestionsDoug Holladay is 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. He is the author of Rethinking Success. Doug was formerly a senior officer with the international investment banking firm Goldman, Sachs and Company, headquartered in New York. At Goldman Sachs, he worked in the Investment Banking Division on a range of matters, strategic and administrative as well as on certain international transactions with a governmental component. While with Goldman Sachs, he served as founding President of One to One Mentoring Partnership (Points of Light), an initiative of the New York financial community to bring imaginative solutions to some of our most pressing urban youth challenges, now known across the country as Mentor.


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