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Game Changer: 10 Questions with Doug Holladay

What does success mean in today’s ever changing world, especially as we find ourselves navigating through a global pandemic? Doug Holladay, author of Rethinking Success: Eight Essential Practices for Finding Meaning in Work and Life aims to redefine our perspective.  

Holladay has never shied away from posing the big questions. He quotes what Socrates said 3000 years back: “The unexamined life is not worth living.” As an active private equity investor and prolific board member, he serves as the Heinz Christian Prechter Executive in Residence at the Georgetown University School of Business. He is also the founder and director of PathNorth, an organization which promotes the exploration of meaning and purpose among world leaders and high-profile executives. He previously worked at Goldman Sachs in New York and at the White House under Chief of Staff James A. Baker, later serving at the State Department as a special ambassador to South Africa. He has delivered public speeches to leadership gatherings in more than 40 states and 10 nations.

We caught up with Holladay in his Washington home, where he gave insight into proven practices which engender meaning and higher purpose in life and work. He also gave us some thoughts on the current pandemic.

1. Considering what we are all facing right now with this pandemic, how does embracing fear lead to breakthroughs?

I have a chapter in the book on risk. I lost my grandmother, mother, and father all within six weeks when I had just turned 30 years old. It gave me a sense that life is really brief and highly unpredictable, so make the most of it. The English poet John Dunn had a skull on his desk. He wanted to be reminded that this life is really short. Rather than depressing him, this fact empowered him to live a life of meaning and service.  So diminishment and fear can be redirected to make us better versions of ourselves if we let go and embrace the bigger meaning for our lives.

2. You have a very different take on leadership–less about technique and more about meaning and purpose. Why did you write “Redefining Success?”

I’ve been asked over the years to write a book. One of my dearest friends, Steve Case, co- founder of AOL,  said, ‘You’ve helped leaders understand what truly matters, why not write a book? You have three boys–wouldn’t you like to capture this for them?’ That was persuasive. The world doesn’t need another book, but I do feel my voice is a unique one.

3. You talk about how “we are all born into someone else’s story.” Why do the stories we are born into matter?

We are all shaped by our backgrounds–the good, the bad, and the ugly. It matters, shaping your future views on just about everything. For instance, how your parents defined success will be a key driver in your own view. We model the things that we observed from our earliest days, whether consciously or below the surface. As the son of Warren Buffett once told me, “We’re all born into someone else’s story.”  Embrace that reality for what it is, then you can pivot to a new paradigm.

4. For decades, you have “been in the room” with so many powerful leaders. How would you describe them?

The unintended consequences of great success is often, sadly, to isolate and disconnect. I observed this up close and personal with some of the most accomplished people in the world. We all feel, on some level, that we are imposters. In a study of over 3000 CEOs in INC magazine, half reported they were lonely, while 68% reported making bad decisions since they simply had no one to trust. There’s an epidemic of loneliness in America. According to Dr. Vivak Murphy, former Surgeon General, he names loneliness as the number-one health crisis above smoking and obesity. And while this is true for society as a whole, leaders are especially prone to this affliction.

5. So what’s the anecdote to a disconnected life?

I would suggest a few things. One, create space daily to ponder something inspirational and uplifting. Each day, I try to write down three to five things for which I am genuinely grateful.  This might be something as pedestrian as a cup of Italian dark roast coffee or the setting sun–things that are really tangible and specific.  We all know those things that are not working in our lives, no need to write those down. But we simply must create room for the good things that are occurring all around, things we take for granted. Gratitude, according to neurologists, actually changes our brains … for the good. Next, investing in a few good friends is time well spent and essential to thriving. The practice of being alone and content is also extremely important to well-being. I take 15 CEOs to a Trappist monastery every year, and most are not religious. There, we learn to be quiet and content with ourselves. In 1666 Blaise Pascal, the French philosopher and inventor, observed, ‘The fundamental problem of a person is never learning to be alone within four walls.’ Socrates cautioned likewise: ‘Beware the barrenness of a busy life.’

6. How does friendship play a role in redefining success?

Men, by nature, can be more solitary than women. Both culturally and due to the roles we play, we tend toward not connecting on an emotional level too deeply. Further, we typically define ourselves by our work. We are what we do, to some extent. We have not been socialized to connect like women–heart to heart. If you go out and eavesdrop on conversations, women typically are talking about things that really matter; men are talking about the market or sports. This is a gross exaggeration but frankly, men have not been trained to speak a language of the heart. This is why friends are so vital for men to nurture. Meaningful relationships matter to our well-being. Yet it takes some risk to invest in such friendships. But a risk well worth taking.

7. What do you consider some silver linings of the current pandemic?

Like Mike Tyson said, “everyone has a plan until you get punched in the nose.” This pandemic is forcing people to look within or ponder deeply. My new book is entitled, Rethinking Success. To some extent, we are all rethinking everything right now. It’s terrifying on one level, yet also affords the chance to get to know ourselves. Many of us run hard, often to not face things about who we are. We now have a great chance to get still and consider so much that we have been avoiding. But we must be brave. Who knows what we will discover? This is true also for our culture at the moment. As Churchill once said: ‘We are not sure whether this is the end of the beginning or the beginning of the end.’ Uncertainty and ambiguity are the greatest points of  stress in our life currently.  It’s almost better to know the worse than to not know anything for sure. This is such an ambiguous time, disconcerting but affording us a chance to grow if we will allow it.

8. You’ve quoted David Brooks’ Ted Talk, in which he says: “Which do you live for: your resume or you eulogy?” How would you define legacy?

Achievers are comfortable with resume type discussions concerning accomplishments and success as culture defines it. A eulogy is something quite different. It relates to who we are, the essence of our heart, our care for others, what others valued about us, those soft things that will be remembered long after the merit badges are forgotten.

9. You teach MBA students at Georgetown University. What matters most to this generation of talented young professionals?

I’ve taught about 800 MBAs now. I think there’s something shifting–many would take less money if they could be a part of some enterprise or company that is purpose driven and stands for something beyond profits. They are inclined toward making a difference and living much more holistic lives. My experience is that this generation which was coddled, entitled, and told they could be anything, are themselves rethinking what success truly is. They want a more integrated life and to not wait forever to be fulfilled. They prize the double bottom line: doing well but also doing good. I think you’re going to see more impact investing–and more socially responsible companies. These young professionals will be loyal to a purpose driven company but not just to a paycheck.

10. How do you think travel helps us redefine success?

Travel opens us to people, ideas, and moments that stretch us and take us to new places within. We gain a broader perspective on what truly matters. Keep traveling.

For more information on Rethinking Success, visit To learn more about PathNorth, visit

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