Q&A with Doug Holladay, Author of Rethinking Success

Doug Holladay is the author of Rethinking Success. He worked at Goldman Sachs from 1987 to 1993 in the firm’s Investment Banking and Executive Office Divisions in New York.

Your recently released book, Rethinking Success, comes at a very disruptive time. What are you challenging your readers to rethink?
Doug: This is a cultural moment when so many of us are rethinking just about everything. What does it mean to experience isolation? What is true happiness? How much is enough? What will be the future of work? Will my children have a path? What brings true satisfaction? My book challenges the reader to reimagine success or broaden one’s notions of success to include what truly matters. This begins with self-reflection. As stated by Socrates, “The unexamined life is not worth living.” So many of us have unconsciously defined our success by certain societal metrics such as degrees, net worth, finished deals and our children’s accomplishments. We need to direct our thoughts to becoming better versions of ourselves. The New York Times columnist, David Brooks, contrasts our ‘resume’ virtues with our ‘eulogy’ virtues. One is a series of accomplishments that, while temporarily satisfying, can leave us empty and longing, while the other speaks to our deeper identity and values, those things which will be recalled at our funerals. These unsettling times underscore what Einstein observed, “Not everything that can be measured matters, and not everything that matters can be measured.”

What are we learning during this time when COVID-19 is dominating so much of people’s time?
Doug: Fundamentally, we are realizing that we are not always in control. Accomplished people want to control all variables. I refer to this as the “mythology of certainty” which is the belief that things in our world will always remain as they are. This epidemic, at least at this point, is unfixable. As a result, the “mythology of certainty” is shattered, thus generating profound anxiety. Oddly, not having answers can be more disconcerting than knowing the worst. Learning to let go is a spiritual practice. Admitting that we are not gods who have control of our fate is humbling.

In your book, Rethinking Success, you discuss the unintended consequences of success and achievement. Please explain.
Doug: It is ironic that the things we aspire to attain such as success, money, notoriety and security etc. have a soft underbelly. The attainment of such can isolate and disconnect us from others. Some years back, an INC study of 3000 CEO’s reported that 50% were lonely in their roles. Of that number, 67% said that they were making poor decisions because they had no one to trust. According to the UCLA Loneliness Index, half of all Americans self-report that they are lonely. Former Surgeon General, Vivak Murthy, named, not smoking or obesity, but loneliness as the number one health challenge in America. This isolation is amplified among leaders. French scholar, Alexis de Tocqueville, toured our nation in the 18th century to discover that tight knit communities striving toward common goals was America’s genius. This contrasts with the findings of Dr. Robert Putnam in his book, Bowling Alone, where he shows that bowling and movie attendance are now mostly solitary activities. This loneliness is not healthy for individuals or our nation at large.

You started PathNorth ten years ago. Please explain why you launched this effort for leaders?
Doug: PathNorth brings together accomplished individuals to have important life conversations in a ‘safe’ environment. It can be unsettling to explore the ‘why’ questions rather than ‘how’ questions. PathNorth was the brainchild of myself and several friends. We think that everyone has a story that we can learn from. Seven years ago, PathNorth gathered twenty-five leaders for a trip on the fabled Orient Express. We took magicians with us and called our trip the “PathNorth Magical Mystery Tour.” Each evening, we asked the guests two questions that related to a magic theme, such as What were the illusions you had about life? And, what are the mysteries you are still trying to figure out? The sharing was deep, connecting us in important ways.

In your book you discuss specific practices that contribute to a meaningful life. Would you please share some of those?
Doug: The practices that shape a meaningful life are actually quite accessible having stood the test of time. For example, create space daily to ponder what truly matters. Start small for about two minutes each day and lengthen this time as you experience the benefit. Write in a journal by hand to clarify your ideas. Additionally, you can keep a gratitude list. No need to list things that aren’t working in your life, as you likely obsess over those regularly. Do this exercise about four days a week and write down two to four things. Neurologists say that this practice will change your sense of wellbeing. Meditate on something inspirational to you and most importantly, invest in genuine relationships. We are made for friendship yet success and busyness often gets in the way. Lastly, never stop taking risks. Palliative nurse Bonnie Ware from Australia observed the regrets of the elderly before they died. She notes that most lamented too often listening to their fears and shying away from risk. We are most alive when we push ourselves in new ways.

What are some things you learned while at Goldman Sachs that have helped you along the way?
Doug: The Goldman people shape the culture and set a high bar for achievement. The best professionals globally long to be a part of this culture of excellence which brings out the best in everyone. I valued the “we” versus “I” mentality that builds trust and camaraderie long term. Also, I learned that it is possible to be smart and competitive, while still kind and generous at the same time. Lastly, I saw how honest feedback creates growth and change. It was such a privilege to have spent time at this prestigious firm.