This excerpt was adapted from the book Big Time Off, written by DJ DiDonna. Simon Element, an imprint of Simon & Schuster, July 2026.
While every sabbatical is unique, there are patterns that connect even the most disparate breaks. Understanding these themes can help us plan our sabbaticals in advance, take advantage of our strengths, and avoid getting foiled by our weaknesses while we’re gone.
The three catalysts
Broadly speaking, there are three types of catalysts for sabbaticals: positive, negative, and neutral. A positive catalyst requires something unexpected and out of the ordinary to give you the financial or logistical freedom to take off. Maybe you receive severance from a job, sell your company, or inherit money when a long-lost great-uncle dies. (Okay, not so positive for your uncle, but a windfall for you . . . )
Negative catalysts are unwelcome and often sudden. A crisis occurs on one of the vectors of your life: a professional setback, a relationship ending, or a health crisis (yours or that of someone close to you). A neutral entry isn’t a surprise, and it doesn’t come about as the result of a major event, windfall, or tragedy; like vacations or retirement, it’s something we come to expect as part of our life.
The positive catalyst
Of course, everyone hopes for a positive beginning to their sabbatical, something akin to a big win—what I call the “windfall start.”
Basically, a victory lap arising from some success. The windfall enables you psychologically (if not financially) to take the break of your dreams. In addition to relieving the financial pressure of a sabbatical, a windfall also quiets the voice that says you don’t deserve it. We’re okay with treating ourselves after a big win, whereas we’re less comfortable doing so when things aren’t going well.
But few in this privileged position ultimately take time off. Not because of any concrete barrier but because the idea is so psychologically foreign and intimidating. All too often, people who have had a big win rush off to the next thing, high off the fumes of their success, cocksure that the quickest way to their next triumph is a straight path forward.
Our internal programming—that we must work in one uninterrupted sprint for our entire adult lives—runs counter to the idea of savoring the win with a break.
Most of us think of retirement as our windfall, when we’ll finally have the opportunity to check all those items off of our bucket lists, to live the lives we’ve been postponing. Unfortunately, the opposite happens far too often; my interviews are littered with stories about parents or grandparents saving up their entire lives only to be thwarted later.
Most fear that financial limitations will be their retirement burglars (delaying retirement age is a worldwide trend), but more often physical or psychological incapability, whether ours or that of our partner, rob us of our long-awaited dreams.
For those who make it to retirement age with the ability to pursue their dreams intact, their internal wiring might still prevent them from enjoying it. Our jobs take up the majority of our waking hours. When we take our step back from our place of work, we leave not only the mundane work tasks behind but also our relationships, ongoing learning and growth, and the harder-to-pin-down feeling of usefulness to others. If you’ve spent your life focused on productivity—and so many of us have—the vacuum left after work vanishes can be devastating.
All the more reason to claim a life outside of work sooner rather than later, and as soon as possible.
The negative catalyst
Approximately two-thirds of sabbaticals fall into this camp, which I refer to as the “time bomb.” The classic time bomb is fomented by an unexpected negative personal or professional event. For example, an end to a relationship or the sudden illness or death of a loved one—usually a parent, but more unexpectedly a spouse, child, or friend close in age. Or the sudden loss of a job, let alone burnout in one you haven’t left.
An emergency is no way to start one of the most highly anticipated experiences in your life. Negative sabbaticals are more expensive because they’re often sudden and unplannable. Gone is the ability to decrease costs by arranging things ahead of time, such as subletting your place or choosing a shoulder season during which to travel. Negative sabbaticals are also less self-directed because an external event has snatched away your agency. You lose control of the narrative of your time off, as well as your emotional state and, many times, your geographic location. As Mike Tyson once said, “Everyone has a plan until they get punched in the mouth.”
Finally, negative sabbaticals also require more time off than the average to be successful. You can’t expect to launch directly into a transformative period of self-discovery if you’re completely worn down or in shock. First, you must recover, which takes time. As one company leader put it, “I came to think of my time leading my organization as collecting various small injuries. Over time, the little things on the personal and professional fronts add up to overwhelm and take you down altogether, ultimately requiring significant time to heal and get back to baseline.”
Humans are afraid of change. We’re much more comfortable staying the course than leaving our familiar habits and patterns, no matter how counterproductive they’ve become. We’d rather be in a bad spot that we’re comfortable with than risk striking out anew. Anyone who has stayed in a bad relationship—personal or business—understands this sad reality. As sabbatical alums, or those who’ve ever quit a job working for a toxic boss, know, it’s often not until you’ve left that you realize the negative impact of the work at all.
It can take an enormous amount of effort and energy to pull off a sabbatical, especially as responsibilities and constraints increase over the course of your life. Waiting until something goes wrong to catalyze your sabbatical won’t preclude you from the many benefits of doing so, but it will require more time and money, and give you less control of its contents. All the more reason to schedule your break far in advance.
The neutral catalyst
Imagine a world in which taking a sabbatical is the same as taking any other break from work. After all, you don’t have to convince yourself to leave the office over the weekend or go through all of the additional logistics to execute your child’s summer break.
Think of a neutral catalyst like how you treat owning a car (maybe even your red convertible). Car ownership requires periodic maintenance like oil changes and annual inspections. We perform these regular checks not because of any perceptible change in our car’s performance but because no matter how inconvenient or costly these things are, it’s much more inconvenient and expensive to perform major emergency repairs. An auto emergency is completely disruptive, so we’re willing to trust the mechanic and put aside the time and money on a regular basis to prevent an unexpected crisis.
In an ideal world, our employers would provide us with both the time and resources for an extended, paid leave. In some parts of the world, governments have already taken this on as a part of the social contract. Until we get there, we must treat a sabbatical as something we make time and space for in our lives and on our calendars. Expecting to take a sabbatical doesn’t necessarily make the sabbatical process easy. But this expectation takes a couple of psychological barriers out of the equation, like how much savings you’ve stored up, or whether it’s exactly the right time to take off. Otherwise, like a neglected car, if you wait too long to take a sabbatical, a sabbatical will take you out of service unexpectedly, and at great cost.
Excerpted from BIG TIME OFF: The Transformative Power of Sabbaticals and How to Take One. Copyright © 2026 by Dennis Joseph DiDonna. Reproduced by permission of Simon Element, an imprint of Simon & Schuster. All rights reserved.
