View CPD's presentation panel of 5 Big Life Decisions from February 28, 2023.

Imagine yourself back in your section classroom during RC year at HBS. Look to your left and look to your right. Where do you think these classmates will be in 30 years? Consider what challenges they may have overcome in that time, what accomplishments they will be most proud of, where they will live, and whose lives will be impacted by their personal and professional presence.

Fred Singer (MBA 1992) and Tori Hackett (MBA 1994) asked themselves these same questions 30 years ago as Singer was set to graduate from HBS and Hackett was about to start her MBA journey. But instead of simply pondering the questions, Singer and Hackett chose to be active in their pursuit of answers. The result is a project 30 years in the making, 5 Big Life Decisions, a documentary which tracks 40 members of the HBS Class of 1992 and tells the life stories of leaders making a difference in the world.

30 Years and 40 Stories

With 900 possible storylines to track, in 1992 Singer and Hackett sought out input from classmates to choose the 40 people they would plan to interview every five years at HBS reunions. With their suggestions, four topic areas emerged reflecting changes in the workforce and society.

Namely, the Class of 1992 wanted to learn about the experience of women in the workforce as the numbers of women in business was steadily growing. They also wanted to understand the experience of their Black classmates moving into leadership roles in a racially charged environment, as well as their international classmates returning to Eastern Europe after the fall of communism. Furthermore, while the conversation around entrepreneurship is commonplace in 2023, 30 years ago at HBS very few students planned to start their own companies. Singer and Hackett wanted to see how those plans were put into play right after HBS and over the course of a career.

All of these stories needed to start somewhere, and Singer and Hackett found that somewhere in a basement room on the HBS campus. Setting their subjects up next to a fake potted plant, each person was asked hundreds of questions from “How much money do you think you will make?” to “Who in your family will do the dishes?” Those Betamax video recordings were filed away, not to be viewed again for close to 30 years, and then new recordings were made at five-year increments, slowly evolving as technology changed. Alums who returned for reunion, or who could be visited in person or via Zoom, would sit down to reflect on their past five years, each interview building a life story.

Key Themes Over 30 Years

While Singer and Hackett hypothesized themes, what they didn’t expect was how stories would evolve over time. “Story arcs just take time,” Singer shared. “In the first five to ten years people were starting careers, marriages were in their early stages, and first children were being born. We found at 25 and 30 years stories came together.” Each individual story also included a “muddy middle” that often wasn’t discussed until a later interview. “As you get older, there’s a bit more humility in who you are and the disappointments and failures are a thing of the past you feel more comfortable sharing,” he added.

These stories of ups and downs and wins and losses that were told over time were quite powerful and captured both the themes Singer and Hackett expected and new learnings about personal and professional growth.

The Lived Experience

The most powerful demographic-based theme that emerged from interviews was the constant feeling of guilt experienced by women in the workforce. “We found that even starting from the five-year reunions, women were tortured by the tradeoffs of family and work,” said Singer. Peak parenting years and peak career years collided in their 30s and 40s and while male alumni also felt the need to make tradeoffs, the sense of guilt felt by women was unique.

For Black alumni, the discouraging truth was that racism had been part of every participant’s story over a span of 30 years. Very little has changed. Lisa Cleveland (MBA 1992) shared in the documentary that as a Black woman she felt the constant pressure to do everything twice as well. In addition, John Rice’s (MBA 1992) experience as a Black professional led him to create Management Leadership for Tomorrow (MLT), a national non-profit organization that fights racial and economic disparities by empowering a new generation of diverse leaders.

The international alumni who participated in the documentary and later went on to high-level leadership positions around the world shared challenges of navigating hierarchical societies. Sitting in the CEO seat during an HBS case study was a very different experience than moving into roles and companies with a rigid structure that discouraged risk taking. For some, learning flex-leadership styles helped them to find success and others found company cultures outside of their home countries where they could thrive.

Finally, a common thread for the entrepreneurial minded alumni was navigating the gray area between success and failure. As Evan Marwell (MBA 1992) notes in the film, over time, 70% of the businesses are actually operating in that middle zone between success and failure—it’s not all great or all terrible—leaving entrepreneurs to question throughout their careers whether they stay or go.

Finding Your North Star

In addition to tracking the stories of specific demographic groups, three other key themes emerged from the documentary. The first was the concept of finding your North Star.

What Singer and Hackett found is that every step of the road cannot be anticipated, but there’s something to be said about understanding what you love and the impact you want to make in the world to help set your direction. “Sometimes it's a plan, sometimes it's a North Star, sometimes it's just a general inner compass, and that compass turns out to be something that you absolutely have to pay attention to,” Singer said. “We found that many narratives stayed consistent for someone’s whole life. Even if they move away from passions for practical reasons as some point in their career, they come back.”

This idea of finding your North Star or inner compass centers on three points according to Singer—understanding your identity, your values, and your mindset. Reflecting on who you are and why you exist in the world, what values you intentionally live out, and your ability to handle change are cornerstones of this process. Watching alumni manage these questions and the decisions they make based on their answers over their lives provides a powerful tool for the viewer’s own self-reflection.

Resilience in the Face of Adversity

The mindset theme was further reiterated by participant’s stories of handling change in their own lives. As Singer noted “It’s not all good!” There were many personal losses, divorces, health challenges, lost jobs, failures, and criticisms endured over the years.

Baroness Dido Harding (MBA 1992) offers a notable example. Throughout her career she faced intense criticism because of a cyberattack on her company TalkTalk and in her public service work heading up the NHS Test and Trace program in England during the COVID-19 pandemic. As Singer notes, “The ability not to be destroyed by criticism and not to let external things define you is incredibly important. It allows you to take risk allows you to explore more and is hugely powerful.”

The Class of 1992 has also navigated difficult economic conditions at various stages throughout their careers. Recessions and crises of 1992, 2001, 2008, and 2020 all impacted alumni to varying degrees, but what Singer and Hackett found striking was how some alumni reflected back on challenges as “blips” on a long-term chart of life and career.

The Difference Between Happiness and Success

In addition to the nuances of each alum’s story and the micro-themes that connected them, a fourth and final major theme that emerged was the ease at which success could be more clearly targeted as compared to happiness.

“Success is like taking a test,” Singer shared. “You know what's on the test, you know how to work hard. So, you work hard, you're diligent and you're smart, and that you will get a good result. But happiness comes back to our earlier point (the North Star), which is if you actually don't know what makes you happy, you will struggle to find it.”

Therein lies the point that Singer and Hackett find so powerful about the documentary—the film is not something to be viewed passively, but rather it can and should be used as a catalyst for understanding what happiness and success look like to you. “You can study happiness and read statistics about what percentage of people say they're happy, but that's not what this is about,” Singer shared. “With these amazing video case studies, you can see somebody with your exact problem and start the discussion for your own self-discovery.”

To learn more about scheduling a showing of 5 Big Life Decisions for your group or organization, connect with Singer and Hackett on Instagram at @5biglifedecisions or via email at View the trailer for 5 Big Life Decisions, or watch CPD's presentation panel from February 28, 2023.