A great sabbatical does not begin the day you stop working, and it does not end the day you return.

In this episode of the Sabbatical Journey Podcast, Alan Briggs walks through one of the most important parts of the sabbatical process: how to enter it well and how to return well.

September is a natural transition point. Some leaders are just returning from a summer sabbatical, while others are beginning to think ahead and plan for next year. Wherever you are in the process, how you step into sabbatical and how you come back matters.

Alan explains why the final week before sabbatical should be intentionally lighter, why your team should feel prepared before you leave, and how to avoid launching into sabbatical at full speed. He uses the picture of a gentle boat ramp into a glassy lake to describe what healthy transition can look like.

He also walks through the return. Rather than stepping immediately back into a full calendar, Alan recommends a gradual reentry: roughly 50% capacity the first week back, 70% the second, and no more than 80% moving forward. That margin gives you space to pay attention to what changed during sabbatical, what your team learned while you were away, and what may need to be redesigned in the next season.

One of the central ideas in this episode is simple:

Don’t resign. Redesign.

Sabbatical often creates clarity around what no longer fits. Alan explores how leaders can use that clarity to rethink their schedule, role, energy, responsibilities, and the season of leadership ahead rather than simply returning to the exact same patterns they left.

The Sabbatical Journey

Alan Briggs’ field guide walks leaders through the full sabbatical journey, from preparing and experiencing sabbatical to reorienting after the return.

The Right Side Up Journal

A 90 day tool designed to help you name the changes you want to make and build the consistency to carry them forward.

The Sabbatical Journey Self-Paced Coaching Experience

A guided experience for leaders who want practical support through each phase of their sabbatical.

Sabbatical Coaching

If you’ve returned from sabbatical and need help turning what became clear into changes that last, Sabbatical Coaching Group can walk with you through the reorient phase and beyond.

Learn more at sabbaticalcoachinggroup.com.

There isn't one right way to take a sabbatical.

Some people head into one with a list of things they finally have time to accomplish. Others want to travel, explore, and experience a different way of living. Some need to turn inward and reconnect with parts of themselves they've lost along the way.

Knowing what you need matters.

In part two of Alan's conversation with DJ DiDonna, they dig into three sabbatical archetypes DJ identified through his research: the achiever, the explorer, and the seeker. Each approaches time away differently, and each has its own opportunities and pitfalls.

For the achiever, a sabbatical can quickly become another job. The explorer can become so focused on what's somewhere else that they miss what's right in front of them. The seeker can do important internal work but forget that sabbatical should also include other people, experiences, and some fun.

The conversation moves from there into a bigger question: What would you regret not doing with your life?

DJ describes sabbatical as a kind of "regret insurance." It gives you an opportunity to stop putting meaningful things off until retirement and actually test some of the ideas you've been carrying around. Sometimes you discover something you want more of. Other times, you discover the thing you've dreamed about for years isn't actually what you want. Both are valuable.

The point isn't to create the perfect sabbatical. It's to know yourself well enough to create the space you actually need.

What would you regret not doing?

Not what sounds impressive. Not what someone else thinks you should do. What is something you've carried with you for years and keep telling yourself you'll get to someday?

Maybe it's traveling somewhere, learning a language, developing a skill, spending meaningful time with your family, exploring your faith, creating something, or simply finding out whether the life you've imagined is actually the life you want.

DJ's challenge is to make it concrete. Spend 30 minutes with a journal and start writing those things down. Then ask yourself why they haven't happened and when they realistically could.

Maybe your sabbatical isn't possible this year. Maybe it isn't possible for five years.

That's different from someday.

DJ DiDonna is a Senior Lecturer of Business Administration at Harvard Business School, where he teaches MBA courses on entrepreneurship and building meaningful professional and personal lives. He has spent his career translating social science research into real-world tools for positive change.

In 2019, DJ founded The Sabbatical Project to define, explore, and research the role of sabbaticals in modern life. He has helped organizations around the world, from nonprofits to Fortune 50 companies, design and implement sabbatical policies.

His work has been featured in The Atlantic, Harvard Business Review, Time, Fast Company, The Wall Street Journal, and The New York Times.

His new book, Big Time Off, brings together his research, personal experience, and stories from sabbatical takers to explore what becomes possible when we create meaningful time away from work.

Big Time Off

DJ's new book brings together years of research and real-world stories about sabbaticals and extended time away from work.

bigtimeoffbook.com

The Sabbatical Project

Research, stories, and resources exploring the role of sabbaticals in modern life and work.

thesabbaticalproject.org

Connect with DJ DiDonna

linkedin.com/in/djdidonna

The Sabbatical Journey

Alan Briggs' field guide for preparing for, experiencing, and returning well from a sabbatical.

If this conversation has moved sabbatical from something that sounds interesting to something you're seriously considering, Sabbatical Coaching Group can help you figure out your next right step.

Learn more at sabbaticalcoachinggroup.com.

What happens when you finally have enough time away from work to see your life clearly?

DJ DiDonna has spent nearly a decade trying to understand that question. After his own sabbatical changed the direction of his life, he founded The Sabbatical Project and began researching what actually happens when people step away from work for an extended period of time.

In part one of this conversation, Alan sits down with DJ to compare what the research says with what we've seen through years of walking alongside leaders on sabbatical.

They talk about why sabbaticals are becoming more common, why so many people wait until something goes wrong before stepping away, and what happens when work has slowly taken up more of our identity than we realized.

DJ also shares his own story. On paper, he had built the company and career he wanted. Underneath it, something wasn't working. He describes what he calls "functional workaholism," where life can look successful from the outside while you're operating at a lower level on the inside. Sabbatical gave him enough space to recognize it, reconnect with parts of himself he had neglected, and consider what he wanted the next season of his life to look like.

The conversation also gets into something that's difficult to measure but shows up again and again in the research: people often come back from sabbatical feeling more human. They rediscover hobbies, relationships, curiosity, creativity, and parts of themselves that didn't have much room when work was setting the pace.

Why sabbaticals have gained momentum over the last decade

What DJ's research reveals about why people finally decide to take one

DJ's experience with functional workaholism and the sabbatical that changed the direction of his life

Why identity can become so closely connected to our work

What it means to develop a more human relationship with work

How sabbatical creates room for relationships, curiosity, creativity, and things that are important but rarely urgent

Why some of the most meaningful sabbaticals happen during seasons of difficulty

The role sabbatical can play in seasons of celebration and transition

What leaders can learn by paying attention to what changed while they were away

What in your life is important, but never urgent?

For DJ, sabbatical created room for things he had said mattered but that his calendar told a different story about. Relationships, spirituality, curiosity and simply being present had gradually been pushed aside by work.

Most of us have something like that.

The question isn't whether those things matter to us. It's whether the way we're living gives them any room to matter.

DJ DiDonna is a Senior Lecturer of Business Administration at Harvard Business School, where he teaches MBA courses on entrepreneurship and building meaningful professional and personal lives. He has spent his career translating social science research into real-world tools for positive change.

In 2019, DJ founded The Sabbatical Project to define, explore, and research the role of sabbaticals in modern life. He has helped organizations around the world, from nonprofits to Fortune 50 companies, design and implement sabbatical policies.

His work has been featured in The Atlantic, Harvard Business Review, Time, Fast Company, The Wall Street Journal, and The New York Times.

Before this work, DJ cofounded EFL Global, a fintech company that enabled more than $2 billion in capital to underbanked businesses and individuals across twenty countries before its acquisition in 2018.

His new book, Big Time Off, brings together his research, personal experience, and the stories of sabbatical takers to explore what becomes possible when we create meaningful time away from work.

This is part one of our conversation with DJ. In part two, we'll talk about the three sabbatical archetypes, regret, what the future of sabbatical could look like, and how to move from thinking about a sabbatical to actually making one possible.

Big Time Off

DJ's new book brings together years of research and real-world stories about sabbaticals and extended time away from work.

bigtimeoffbook.com

The Sabbatical Project

Research, stories, and resources exploring the role of sabbaticals in modern life and work.

thesabbaticalproject.org

Connect with DJ DiDonna

linkedin.com/in/djdidonna

The Sabbatical Journey

Alan Briggs' field guide for preparing for, experiencing, and returning well from a sabbatical.

Learn more about Sabbatical Coaching Group and take your next right step at sabbaticalcoachinggroup.com.

You come back from sabbatical and almost immediately, things start happening.

People ask what you learned. Your team wants to know when they get a sabbatical. You notice you’re responding to pressure differently. You start thinking more intentionally about vacation, Sabbath, and the rhythms you want to protect moving forward.

And somewhere in the middle of all of that, you realize the sabbatical may be over, but the work of sustaining what changed in you is just beginning.

In this episode, Alan shares some of the patterns he’s seen after years of taking sabbaticals himself and coaching other leaders through them. From reentry and team dynamics to rest, sabbatical policies, and long term change, this is a practical look at what tends to happen after you come back.

What needs to remain different because you took this sabbatical?

Maybe it’s how you use your calendar. Maybe it’s protecting time with your family, receiving a weekly Sabbath, changing the way you respond under pressure, or addressing something in your leadership that you couldn’t see clearly before.

Whatever it is, don’t assume it will stick because it mattered to you during sabbatical. Name it. Put some guardrails around it. Invite other people into it.

Sabbatical creates space for change. Sustaining that change is where the real work begins.

The Sabbatical Journey

Alan Briggs’ field guide walks leaders through the full sabbatical journey, from preparing and experiencing sabbatical to reorienting after the return.

The Right Side Up Journal

A 90 day tool designed to help you name the changes you want to make and build the consistency to carry them forward.

The Sabbatical Journey Self-Paced Coaching Experience

A guided experience for leaders who want practical support through each phase of their sabbatical.

Sabbatical Coaching

If you’ve returned from sabbatical and need help turning what became clear into changes that last, Sabbatical Coaching Group can walk with you through the reorient phase and beyond.

Learn more at sabbaticalcoachinggroup.com.

A sabbatical policy is more than another benefit in an employee handbook.

It says something about what your organization believes.

It tells your people whether they are valued only for what they produce or whether you care about who they are, how they are doing, and whether they can continue leading well for the long haul.

That is why creating a sabbatical policy is not simply an HR decision. It is a decision about culture, stewardship, trust, and the kind of organization you are trying to build.

In this episode, Alan shares what Sabbatical Coaching Group has learned from helping small teams, large organizations, churches, nonprofits, and businesses create sustainable sabbatical programs. He walks through the practical questions leaders need to answer, including eligibility, timing, rotation, years of service, preparation, and internal ownership.

He also addresses one of the biggest reasons organizations never get started. They keep telling themselves they will create a policy someday.

Alan’s advice is simple. Put a date on the calendar, build a thoughtful first version, choose a pilot group, and begin learning. The first round will require more energy, but the process becomes easier as the policy matures and the organization learns how to support it well.

A healthy sabbatical program does not ask people to abandon their responsibilities. It requires leaders to prepare their teams, create clear handoffs, and receive the time away as a gift that should be stewarded well.

When done thoughtfully, a sabbatical policy can strengthen retention, creativity, trust, leadership development, and organizational health. It can also begin changing the story an organization tells about work and rest.

• Why sabbatical policies are about stewardship, not simply time away

• What a sabbatical benefit communicates to current and future employees

• Why organizations should stop waiting for the perfect policy and begin with a pilot

• How to think through timing, rotation, eligibility, and years of service

• Why a responsible sabbatical requires strong preparation and clear team handoffs

• How sabbaticals can support retention, creativity, innovation, and longevity

• Why trust is essential for leaders, boards, and teams

• The importance of assigning a small internal team to oversee the program

• How an organization’s beliefs about work and rest shape whether a sabbatical policy will succeed

What story does your organization currently tell about work and rest?

Your answer may not be written in a policy.

It may be found in how your leaders respond to vacation requests, how your team handles sickness, whether people feel guilty for stepping away, and what happens when someone admits they are exhausted.

A sabbatical policy will not fix an unhealthy culture on its own. But it can become a meaningful part of changing that culture when it is created with intention and supported by the people responsible for leading it.

• What is the purpose of sabbatical in our organization?

• Who will be eligible?

• How long will sabbaticals last?

• How often will team members become eligible?

• How will we determine the best timing for the individual and the organization?

• What preparation will be required before someone steps away?

• What resources or coaching will we provide?

• Who will oversee the policy and handle unique situations?

These questions do not need perfect answers before you begin. They do need honest ones.

The Sabbatical Journey

Alan Briggs’ field guide walks leaders and organizations through the full sabbatical process, including preparation, experience, reentry, and policy development.

The Sabbatical Journey Self-Paced Coaching Experience

This guided experience helps leaders work through each phase of sabbatical with practical teaching, reflection, and planning.

Sabbatical Policy Support

Sabbatical Coaching Group helps organizations create, launch, and strengthen sabbatical policies and programs. The team has experience supporting individual leaders as well as large organizations with hundreds of people moving through sabbatical programs.

You do not have to build the policy alone or invent the process from scratch.

Learn more and schedule a conversation at sabbaticalcoachinggroup.com.

There comes a point in every sabbatical where you can see the finish line.

For some leaders, it's exciting.

For others, it's unsettling.

You've finally slowed down enough to think clearly. You've had conversations you needed to have. You've noticed patterns that were impossible to see while you were moving at full speed. You know there are things you don't want to carry back into work with you.

Then reality starts knocking. Your inbox is filling up. Your calendar is coming back to life. Your team is getting ready for your return.

And one question quietly begins to surface.

How do I go back without becoming the same person I was before I left?

That's what this episode is about.

The final phase of a sabbatical isn't simply returning to work. It's learning how to carry the changes you've experienced into everyday life. That's easier said than done. Most leaders don't lose the benefits of a sabbatical because they lacked good intentions. They lose them because they return to the same pace, the same rhythms, and the same expectations that exhausted them in the first place.

Alan walks through what a healthy reentry actually looks like. He explains why slowing your return isn't about avoiding responsibility. It's about giving new habits room to take root before old ones reclaim their place. He also shares one of the most important lessons he's learned from coaching leaders through this process.

You can't make changes you haven't named.

If you haven't identified what needs to change, written it down, and shared it with the people around you, you're relying on good intentions to accomplish what only intentional action can do.

Returning well isn't about having one more breakthrough.

It's about protecting the breakthroughs you've already had.

You'll hear why many leaders feel anxious as their sabbatical comes to an end and why those feelings are more common than you might think. Alan also shares why a gradual return matters, including the framework he recommends for easing back into work instead of jumping straight to full capacity.

The conversation explores why reminders are often more valuable than big moments of inspiration, how to redesign your schedule instead of falling back into old patterns, and why naming your changes is one of the most practical things you can do before returning to work.

Alan also shares how communicating those changes with your team creates accountability and gives the people around you an opportunity to support the leader you're becoming, not just the leader you used to be.

As you prepare to return, spend some time with these questions.

What became clear during your sabbatical that you've never actually named?

What needs to change in your schedule so your life reflects what you've learned?

Who needs to hear about those changes before you return?

What would it look like to come back differently instead of simply coming back?

The Sabbatical Journey is a practical guide to preparing for, experiencing, and returning well from a sabbatical.

The Right Side Up Journal is a 90 day guided journal that helps leaders turn awareness into action and build sustainable rhythms after returning from sabbatical.

The Sabbatical Journey Self Paced Course walks you through the entire framework with practical teaching from Alan and the Sabbatical Coaching Group team.

If you're approaching the end of your sabbatical and wondering how to carry what you've learned into everyday leadership, we'd love to help. Many leaders discover that the reorient phase is where the deepest coaching work begins because this is where clarity becomes action.

Learn more or schedule a complimentary clarity call at sabbaticalcoachinggroup.com.

Most leaders walk into sabbatical with a vague idea and a hope. They imagine they'll figure it out as they go. A few weeks in, they realize each day is bleeding into the next, the time is slipping away, and they're not entirely sure what they're doing with it.

The leaders who walk out of sabbatical transformed do something different. They build a plan.

Not a rigid, hour-by-hour itinerary. A framework. Part structure, part freedom. Enough order to give the time shape, enough space to let the rest actually land. In this episode, Alan Briggs walks through five practical blocks every sabbatical plan needs and shows you how to sketch yours out on a single piece of paper.

If you're getting closer to your sabbatical and starting to realize "I'll figure it out as I go" isn't a plan. If you've blocked the time off but you have no idea what to actually do with it. If you're worried you'll get a few weeks in and feel bored, restless, or guilty. If you've already started planning and want a clear framework to test it against. This one is for you.

"This does not have to be exotic. This does not have to be expensive."

"Usually the most restorative stuff is the cheapest stuff."

"Your soul tends to be freshest at the very end of the sabbatical."

"We want you to come back ready to risk some new things based on what God revealed during your sabbatical."

"Your heart and soul need time between these. Try to space them out."

If you sketched out your sabbatical timeline today, where would the gaps be? What's missing that you haven't given yourself permission to plan for?

What does your spouse actually want from this season, and have you asked them yet?

What kind of reflection space have you built in at the end of your sabbatical to capture what God is showing you, before you walk back into work?

The Sabbatical Journey by Alan Briggs is the field guide that turns this conversation into a full process, including the timeline structure, coaching questions, and reflection prompts referenced in this episode. Available on Amazon and through Barnes & Noble online.

The Sabbatical Journey self-paced coaching journey walks you through the planning process at your own pace, with video sessions from Alan and the SCG team.

If you want to talk through your specific plan with someone who's walked dozens of leaders through this, book a free sabbatical clarity call. It's a real conversation about where you are and what your next step looks like.

Find all three at sabbaticalcoachinggroup.com.

When most people picture a sabbatical, they picture the destination. The beach. The trail. The cabin in the woods. The Instagram-worthy moment in front of the Alps.

The leaders who actually come back from sabbatical transformed will tell you something different. The destination doesn't make the sabbatical. The preparation does. The work you do in the months before stepping away is what separates a season that changes you from a season that quietly disappoints you.

In this episode, Alan Briggs walks through five specific areas every leader needs to prepare. Skip any one of them, and the gap between what you hoped for and what you actually experience starts to grow. Prepare them well, and you walk into your sabbatical clear, free, and ready for what God wants to do.

If you're sabbatical-curious and starting to wonder what the work actually looks like. If you've been quietly planning a sabbatical and you're starting to feel the weight of everything you need to figure out before you can leave. If you've been promised a sabbatical by your organization and you don't want to waste it. If you're months or weeks away and you're starting to wonder whether you've prepared the right things. This one is for you.

"The hard work is in the preparation."

"Sabbatical is a gift, but it comes with the responsibility to steward it well."

"Your team will develop new leadership capacity because you're away."

"This does not have to be exotic, and it does not have to be expensive to be incredible."

"Whether you're 18 months out, 18 weeks out, or 18 days out, you've got some preparation work to do."

If you were honest with yourself, which of the five areas (heart, schedule, family, mind, or team) are you most likely to under-prepare? What does that reveal?

What do you think you'll actually miss about your work when you step away, and what does that tell you about where your identity is right now?

Who on your team has been quietly ready to carry more, and what would it look like to use your sabbatical to give them that opportunity?

The Sabbatical Journey by Alan Briggs is the field guide that turns this conversation into a full process. It includes the coaching questions, the communication plan, and the timeline structure Alan references in this episode. Available on Amazon and through Barnes & Noble online.

The Sabbatical Journey self-paced coaching experience walks you through our entire coaching process on your own timeline, with video sessions from Alan and the SCG team built around the same five areas.

If you want to talk through where you are and what your next step looks like, book a free sabbatical clarity call. It's a real conversation, not a sales pitch.

Find all three at sabbaticalcoachinggroup.com.

What if you stepped away from work. Not for a week. Long enough that the constant hum finally goes quiet. Long enough that you stop reaching for your phone. Long enough to remember what you used to love doing before life filled up.

For most leaders, that idea creates two reactions at once: deep longing, and total panic. Longing for the rest. Panic at the thought of an open stretch of time and no clear sense of what to do with it.

That's the gap this episode fills. Alan Briggs walks through the six elements that turn a sabbatical from "extended time off" into something that actually changes how you lead, how you live, and who you are when you come back. If you've ever quietly wondered whether you need a sabbatical, or wondered what one would even look like, this is the conversation that makes it concrete.

If you've never seriously considered a sabbatical but the word keeps catching your attention. If you know you're running on fumes and you're starting to wonder if a vacation isn't going to be enough this time. If you're a pastor, executive, or leader and the idea of stepping away for an extended season sounds amazing and impossible in equal measure. If you've already started planning a sabbatical and you're stuck on the "but what would I actually do" question. This one is for you.

"Make sure it's a get-to, not a have-to."

"Change of pace plus change of place equals change of perspective."

"You don't have to have an extravagant sabbatical for it to be an amazing sabbatical."

"Sabbatical coaching isn't an expense. It's an investment."

If you had an extended stretch with no work obligations, what's the first thing that would come up in you (excitement, anxiety, guilt, all three)? What does that reveal about where you are right now?

What's the difference, in your own life, between rest you've earned and rest you've actually received?

If you were honest about your current pace, how long could you sustain it before something has to give?

The Sabbatical Journey by Alan Briggs is the field guide that turns this conversation into a full process. It walks you through every element you heard about in this episode, with space to write, plan, and prepare. Available on Amazon and through Barnes & Noble online.

The Sabbatical Journey self-paced coaching journey takes you through the same framework Alan uses with the leaders he coaches, with video sessions you can move through on your own timeline.

If you want to talk through what a sabbatical could look like in your life, book a free sabbatical clarity call. It's a real conversation about where you are and what might be next.

Find all three at sabbaticalcoachinggroup.com.

Not all sabbaticals are created equal. If you're trying to figure out how to plan a sabbatical, the type of sabbatical you need depends on your life stage, your context coming in, and what would actually be a gift to you and your family right now.

In this episode, Alan Briggs walks you through four distinct types of sabbatical: adventurous, reflective, connective, and hybrid. He shares honest stories from his own sabbatical experiences, breaks down which type of sabbatical fits which season of life, and gives you a key warning for each one so you don't fall into the most common sabbatical planning mistakes leaders make when preparing for extended time away.

In this episode you'll learn:

Resources mentioned:

Reflection questions:

If this episode helped you think differently about sabbatical planning, subscribe and leave a review. It helps more pastors and ministry leaders find the rest and renewal they need.