What a decade of studying sabbaticals taught me about regret

DJ DiDonna, a senior lecturer at Harvard Business School, is the author of “Big Time Off.”

What do you regret most about your life so far? Is it something you did, or something you wish you had done? How you answer might depend on your age.

When we’re young, we tend to focus on things we wish we hadn’t done — a late night out at a bar or sharp words with a loved one. But as we get older, the true nature of regret begins to reveal itself: regrets of action fade more quickly than those of inaction. What we didn’t have the courage or conviction to do has the more lasting impact.

For almost a decade, I’ve researched people who take sabbaticals — extended leave from their jobs. Sabbatical alumni universally describe their time off in superlatives; as a peak life experience on par in importance with the birth of a child or their wedding day. Among the many benefits they describe about their time away is what I’ve come to call “regret insurance,” and I think it’s crucial for living a fulfilling life.

Given the extended nature of their time off — a proper sabbatical is ideally between three and nine months — there’s ample time to check items off a bucket list, like travel to far-off destinations. But the most transformative sabbaticals included periods of work-like experimentation during which people try out different ways to live their lives.

An example: An English major turned career trial lawyer left his successful practice in his early 40s, with two young children at home, to write a book. This new life not only gave him a chance to test his writing chops, it also enabled him to walk his daughters to school and to be home for dinner. But after three months of writing, he printed out his manuscript a final time and stuffed it in his desk. He returned to work the following week.

Perhaps surprisingly, the lawyer did not view this time as a failure. Instead, he viewed it as a successful way to quiet lingering doubts about his career choice. He found out that a writing life — solitary days spent inside his head — actually didn’t fit his personality. It also helped his wife (“he finally stopped complaining about not having written the Great American Novel”) and inspired his daughter to strike out on her own year-long sabbatical with her family two decades later.

While it’s impossible to know what would have happened had you taken a different path, experimenting on sabbatical provides a close approximation. These experiences create and heighten meaning in our lives, and stave off the regret of a life unlived. Though many people do end up starting a new chapter in their lives while on leave, sabbatical takers often return to their previous roles with greater clarity, energy and a healthier relationship to work.

But despite these benefits, barriers exist. Broadly speaking, these can be sorted into two buckets: responsibilities and perceptions.

Responsibilities are real hurdles, such as financial constraints, dependents and other logistical difficulties, to taking time off. Addressing these requires advanced planning, savings and, in an ideal world, enabling policies from our workplaces or governments. And the financial strain is often lower than people expect. Not only is six months off over the course of a 40- to 50-year career only about 1 percent of a working life, those who do leave their jobs often get raises.

Sabbaticals also impose costs on employers and colleagues who absorb the work left behind. But sabbatical takers offer long lead times and careful preparation to ease the strain. Absences can open welcome opportunities for junior employees to learn new roles in ways that strengthen the organization. And when available to everyone in an organization, these departures build camaraderie and good culture instead of resentment among those who remain.

Perceptions are more imagined, playing off our fears of how others perceive us, or how we’d see ourselves between jobs. To defeat these, it can help to find people who have taken sabbaticals to help muster the inspiration to take the leap.

Given the extraordinary payoff from extended leave, you’d think that the tales these exemplars tell about their sabbaticals would be universally inspirational and positive. However, more often than not, the stories that successfully inspire sabbatical takers are less about the trip of a lifetime and more about the people in their lives who waited too long. Stories abound from my research about parents waiting until retirement to live out their dreams, only to have them cut short by death or disease.

This reality reveals a stubborn truth about human nature: Often it takes a reminder of our mortality to help us live lives more fully in the present. Even for those who successfully managed to take one, I’ve found instead that approximately two-thirds of sabbaticals are catalyzed by a crisis — relationship, job, or health — instead of intentionality and planning.

We’re hardwired to wait until something forces us to see how short and precious life is, but surely that’s not necessary, is it? Why wait for a crisis to discover who you might become?