Skip to main content
DJ DiDonna

DJ DiDonna

Oct 8, 2026

13:00
maybe that fits in with what you were just saying earlier that maybe there are these inflection points that are going to come up in the future so where you do have the luxury to plan and then there may be moments where you don't plan and you're forced into it for those two-thirds that they have time off forced upon them um what do you often see what are some techniques in reframing it happened Now what? And how do I think about it?
13:33
The first thing to do is to avoid that reflex, which is we're kind of taught from an early age that you should be employed, you know, 100% utility from you graduate from high school or college, like employed the entire route until retirement.
13:52
A sabbatical asks you to say, all right, I'm going to take a beat or two before I start looking for a job.
13:58
And again, easier said than done if you're able to save and you have the kind of privilege to take a step back.
14:06
But ideally, if you're kind of saving and thinking about time off in the future, it'll be more possible.
14:13
And so assuming you can do that, instead of rushing into searching for the next job, it's really stepping back and saying, okay, I want to try to heal.
14:24
I want to congratulate myself for the leg of the race I just ran.
18:23
that a sabbatical or that was just like a health thing that I used really well?
13:48
Mm-hmm
13:48
... like employed the entire route until retirement.
13:52
Um, a sabbatical asks you to say, "All right, I'm gonna take a beat or two before I start looking for a job." And again, easier said than done if, if you're able to save and you have the kind of privilege to, to take a step back.
14:06
But ideally y- if you're kind of saving and thinking about time off in the future, um, it'll be more possible.
14:13
And so assuming you can do that, instead of rushing into, uh, searching for the next job, it's really stepping back and saying, "Okay, I wanna try to heal.
14:24
I wanna congratulate myself for the leg of the race I just ran.
14:27
Um, I want to imagine and, and run experiments and practice a little bit different version of myself just to see if, if something else pops out on the other side." Um, I think so many people just run from one thing to another, um, and I, I liken it to grocery shopping while hungry.

30 MINS LATER

44:23
... with, with their sabbatical, either going in, coming out? Just what are those first steps that people can take?
30:43
Mm-hmm.
30:43
If you're kind of journaling about, like, how is this feeling? Um, I have a story in the book about someone who was a lawyer, like lifelong lawyer.
30:52
Always wanted to be a writer.
30:54
And you know, family of two at home.
30:56
He, he quit his job, um, and he was like, "I'm gonna finally write the great American novel." And you know, he got to take his daughters to school, you know, cook dinner, like all this stuff he wouldn't normally get to do.
31:09
Walk upstairs to the attic, you know, on the computer.
31:12
And after like 90 days he printed the manuscript out, shredded it, um, prevented everyone from, anyone from reading it.

20 MINS LATER

50:59
But to kind of prep them for that summer of 2031.
1:32
The three archetypes of people heading into a sabbatical that you experience.
1:36
Yeah.
1:37
I talk, I think about it as like the achiever, the explorer and the seeker.
1:42
So, um, achievement mindset, I think is, is the most common way to think about a sabbatical.
1:47
You're so excited.
1:49
You're putting down your, like, um, your like routine tasks and you're creating all this space.
1:56
And so you want to fill that space with a bunch of things that are intrinsically motivated.

6 MINS LATER

7:49
Any thoughts about that? Maybe people speaking from the other side of regret or even people saying, I'm so glad I seized this time.
13:45
And then at the end of that journey, kind of chapter, how annoying it was to discover that, you know, even though you're doing meaningful work and doing things that most people would say, Oh my God, you, you're living the dream, you know, you're, you're burned out.
14:01
So I was fortunate to essentially create my dream job.
14:06
I, I went to business school saying, okay, I'd like to continue the entrepreneurial journey.
14:11
I'd like to run something myself instead of working for someone else.
14:15
I wanted to do something international, so something that aligned more with my aspirations versus my resume to date.
14:24
And then I wanted to do something that I felt like helped people and created a positive impact in the world.
14:29
I mean, Angie's List doing positive work, but something a little bit more in-depth than helping grandma find a plumber.

18 MINS LATER

32:11
You can contact him via LinkedIn or schedule a Zoom call via the link in the episode description.
16:09
Did patterns emerge in terms of what people told you about what they got from it?
16:15
One thing that was consistent across these interviews, I basically came back from my sabbatical having had a transformative experience.
16:23
Everyone I spoke to who had taken a sabbatical had some sort of transformative experience.
16:29
And so I felt like it was important to put some rigor around it.
16:33
Being around academia, co-founding a company with academics, I wanted something more than just a blog post.
16:39
And one thing that, that surfaced in our research was this concept of peak life experiences.
16:45
And so the kinds of words, the terms in which people were describing the impact of their sabbatical, was on par with what people would say around the birth of their child, their wedding day, the death of a close loved one.

15 MINS LATER

31:49
Do companies usually provide pay? And if they don't, how do people cope?
15:40
DJ, what's maybe one surprising shift you made after your sabbatical?
15:45
I mean, everything changed, right? Like I, I left my company.
15:49
I, you know, was out of a relationship.
15:54
I told a nonprofit that I volunteered with, I was on the board of, I said like, hey, I will donate the rest of my year, you know, six months to you.
16:04
Like, how can I help? And they're like, why don't you come and be kind of like the interim managing director and help us hire someone? So I moved.
16:13
I was working in nonprofits and academia.
16:18
So, you know, I think it's easier to answer like what didn't change.

8 MINS LATER

24:35
What do you see in your research about that difficulty?
8:16
Yeah.
8:16
So as we define sabbatical, as we talk about my experiences over the course of the episode, I would encourage people to think back to your parable.
8:24
And so you've got your grandkid on your lap, and you're describing the experiences in your life, the things you did, the things you didn't get a chance to do.
8:33
And so a sabbatical is a big fancy term, but really, it's an open container.
8:38
You're creating space.
8:39
You're creating open space to f- to put into the story of your life things that you want to experience.
8:45
It's not about a productivity hack.

22 MINS LATER

31:14
There were none.
6:56
[laughs] What was that?
6:57
So I entered sabbatical land, as I call it, as most people do, which is unintentionally.
7:02
So if you don't take a sabbatical, a sabbatical will take you likely.
7:07
You know, I'd run my company for seven years, and I was feeling lower and lower energy, tough to get out of bed, and I was growing even worse facial hair than I have now.
7:16
And my co-founders were like, "Are you okay?" And I think at some point, you know, when it was your dream job and you can't get out of bed to do your, your job, there's a problem.
7:25
It brings up all certain types of emotions around, like, if this won't make me happy, what will? The ice cream sandwich moment was on a particularly sad kind of weekend.
7:34
It was Friday, had no plans.

32 MINS LATER

39:19
2031, right?
46:22
And so, like, yeah, just why would an employer want to do this?
46:27
Yeah.
46:28
Well, I think, you know, back to the quote, I think a great company is thinking on more of a longer-term basis.
46:35
Like, is it inconvenient for someone to leave your company? Absolutely.
46:38
Are people going to leave your company no matter what? Like, are people going to turn over? Are they going to go on parental leave? Like, yes.
46:43
Right.
46:44
And so as a company, you have to build resilience to stand someone leaving, understanding what their job responsibilities are, having other people do it, bringing someone in, training them.

6 MINS LATER

52:47
What's your sense from your research about – do a lot of people who go on sabbatical realize they really don't like their job even if they're very good at it anymore? Like where do people fall on that?
4:10
Can you share with listeners where you were?
4:12
Well, it's a bit of a bookend story because I had just been interviewed at WGBH in Boston about my company.
4:19
And I was fortunate enough to create my dream job.
4:22
It was a company that did good in the world.
4:25
I loved the people I worked with.
4:27
But after working there for seven, eight years, I was not feeling fulfilled anymore.
4:32
And I was feeling a bit of burnout and just kind of not my best self.
9:00
So how do you think about that?
6:07
So how do you think about that?
6:09
I mean, what I try to do in the book is tell stories about people that have managed to make it work.
6:14
And so what we found, one of the biggest predictors of feeling like you can take a sabbatical is knowing someone in your life that has taken one.
6:22
So an exemplar to kind of say, here's what it took to prepare.
6:26
Here's what happened to me afterwards.
6:27
I didn't disappear.
6:28
I got a job.

18 MINS LATER

24:54
Are sabbaticals likely to leave their work or sabbatical lights likely to leave their work and not return? What percentage of sabbatical lights never come back?
8:00
Right
8:00
... put your child hat on and, and remember how, you know, exciting and fun summer vacations were and how as adults, even though summer vacation doesn't make any sense at all, um, for us, we, we maintain that ritual.
8:14
You know, like, kids have summer learning loss when they're outside of school.
8:18
The logistics to, to bring kids around on summer vacation is a pain.
8:22
It's costly.
8:24
But I think we look back at that and say, like, "What an amazing period of our lives where we could just set aside school and, and do whatever we wanted." And so, you know, I, I will answer your question, but I, I do think that we're conditioned to say, like, "Why, why would you need to take time away from work?" Which I think is, like, a failure of imagination, and also [laughs] just our conditioning around this narrative that you work from, like, graduation all the way to retirement nonstop, which is just...
8:52
It's no longer the story, and, and it's just not really possible.

6 MINS LATER

15:01
Right
11:03
And so could you share some stories of some folks who did this and the realizations that they had?
11:11
A couple of my favorite stories.
11:13
One, there was a family that, that took a sabbatical on an island off the coast of Norway.
11:19
So the father had been working in tech, had kind of burnt out, and his wife had taken a few years off from teaching in order to stay at home and raise the kids, right? So she had wanted to get back into the workforce.
11:34
He had wanted to take some time off.
11:36
And so they spent a month above the Arctic Circle off the coast of Norway.
11:40
It allowed-- She was the one of two teachers in kind of a one-room schoolhouse type situation for the island, and he was just experimenting, spending afternoons with his kids, doing little projects and hobbies.

5 MINS LATER

17:07
If folks think, "Yeah, that's great," but where do we go from there?
4:49
But again, we need to challenge that assumption, and actually there's a very clear use case, isn't there, in terms of the m- many, the, the manifest benefits to employers of helping to actually facilitate these kind of breaks for their senior staff.
5:02
I think of a quote by Warren Buffett where he says, "Time is the enemy of the mediocre company and the friend of the great company." So for any company thinking about like a quarter, the next quarter ahead, um, having someone step away is inconvenient, just like having someone quit or having someone go on parental leave.
5:21
But similar to parental leave, we've decided that it's important enough of a human experience that, that we're on board to carry water for our coworkers while they're gone.
5:29
So, you know, first of all, it's, it's about saying this is important enough to make some sacrifices.
5:35
However, what we found in the research is that, you know, smart organizations build the muscle of people leaving and returning.
5:41
It builds resilience.
5:43
It eliminates key person risks.

9 MINS LATER

14:50
We need to look at the day-to-day before we look at these bigger, uh, more impactful, uh, uh, sort of breaks or, or chunks of time." Or, or is that a mistake? Or actually is there equal benefit at looking at all of these things all at the same time?
14:48
Yeah.
14:48
Right? Um, but, you know, looking at, at a four-month or six-month break seems like it's tremendous, right? Um, to your point about geographic separation and, and work, so we talk about the definition as extended leave from your routine work intentionally, right? Um, so routine work, what does that mean? If you're, if you're doing work that does not resemble your old work, you're kind of using a different intrinsic aspect of, you know, accomplishment.
15:17
So again, writing a book, um, doing yoga teacher certification, it might feel like work to someone else, but you're deciding to do it, and it's not exercising the same muscles as your existing work.
15:29
Harvard created the first sabbatical policy, and I believe it was 1890.
15:33
And the purpose was for health, rest, recovery, and the pursuit of, of scholarly activities, right? And so over time, those three have kind of eroded, and you've, you've substituted out such that a sabbatical is trading out some of your responsibilities, teaching departmental responsibilities, but really magnifying research.
15:54
And so the concern about staying in the same place or continuing your routine job is that you're just maybe turning the volume down and shifting the focus and not actually allowing yourself to retreat back to who am I as a person.
16:07
Like, your professional identity is still kind of in place.

9 MINS LATER

24:59
But what are some examples of how this played out?
12:04
You put them into some kind of archetypes and themes, and I thought that that might be helpful to characterize for people.
12:10
Yeah, so I looked at the data and pulled out some archetypes on how people typically use it.
12:15
I think now's a good opportunity to step back and just say, a sabbatical is not a tangible thing.
12:21
It's a container to put whatever your wishes and desires are inside of, right? It's like protected space to work on whatever is important to you.
12:30
So I think I'd encourage your listeners to kind of like close their eyes and think about what is a thing that you wish you could do in your life or that you think you might regret not doing, and then anchor to that as we talk.
12:43
Because everyone has a different bucket list.
12:45
The things that I did on my sabbatical or what you did on yours might not resonate with folks.

18 MINS LATER

30:43
But I look back now and there's times in some of my travels as an example where I was like, what was I doing? Letting that worry and worrying about what re-entry was going to be or what I was going to be doing at the time, take away from just appreciating the experience that I was having that was so fortunate to be able to have, right? And so what did you learn about like why these experiences can be harder than we think?
15:27
Respond to any of those statistics or where does that fit into any of the research that you've been doing?
15:33
It's all from the same river, right? So you can talk about the disengagement crisis.
15:39
You can talk about burnout being a World Health Organization global phenomenon.
15:44
So it's all true, right? And I think the scary thing about those unused vacation days, and I love that stat, is we're already, as Americans, one of the highest income country that vacations the least.
16:01
And I think in the past, the mark of a successful society or a successful upper class was leisure.
16:11
And so leisure use was this thing where if you made it, then you could have a country home and things like that.
16:16
And now the upper class are some of the folks that are most likely to not use vacation days.

35 MINS LATER

50:58
Somebody who's just feeling, my goodness, like the day-to-day getting through my life and my work is just – what advice do you give to somebody who's feeling that internally?
4:18
Right
4:18
... my sabbatical at that time, is that, um, everyone has a different season for what is possible in their life, whether you have certain set of responsibilities or constraints around the geography you can travel in or, or costs.
4:32
So at that point in time, I had just gotten out of a relationship.
4:36
Um, I, I had no responsibilities, so I wanted to engage in this spiritual search.
4:41
I spent, uh, first, uh, you know, about six weeks with my mom, cooking her dinner every night as she recovered from, from an illness, um, which is, you know, not glamorous.
4:51
It's not something you put on the marquee, um, but was really kind of meaningful, I think, to both of us.
4:56
And then I set off on this pilgrimage, uh, this Buddhist pilgrimage in Japan.

9 MINS LATER

13:50
Mm-hmm
23:56
It's a really cool concept because I'd never taken it kind of that next level down.
24:00
Yeah, and I think it's the most equitable benefit that I think you can give.
24:04
I'm kind of modeling this theory of change around parental leave, which paid parental leave, we still have like the worst coverage in all states.
24:12
high income earning countries.
24:14
But like the U.S. has made a fair amount of progress.
24:16
And I think when you go to apply to a company that doesn't have parental leave, like it's a bit of a head scratcher, right? So we're moving in the right direction.
24:23
But, you know, when someone leaves for parental leave, they're gone long enough that other people have to carry the water for them.

11 MINS LATER

35:44
What are thoughts there? Yeah.
22:36
Mm-hmm
22:36
... you know, I had the privilege to, to not have dependents.
22:40
I was kind of, you know, on my own, and so I could, I could make a lot of independent decisions I think people, people don't get to do at all times in their life.
22:48
And I'd officiated my, my best friend's wedding, and they were taking the family to New Zealand, where he was from, and they invited me along.
22:57
So kinda like their second wedding, go explore New Zealand.
23:01
And that was, that was the call that I needed to like, "Okay, let's just go.
23:05
I had no intention to go to New Zealand.

23 MINS LATER

45:49
Yeah
11:29
[laughs]
11:29
So how do you keep, how do you keep your feet kind of safe and blister-free? Um, what do you do when they're not? So it, it gave me a lot of time to reflect.
11:38
I decided that, you know, returning to my company was just, did not correspond with the kinda life I wanted to have, you know, really being enmeshed in community and, and spending time with family.
11:48
I just, I had to be everywhere, you know, living in Asia, Africa, Latin America, and I deci- I had this confidence around I don't know what's next, but that's okay.
11:58
I have the ingredients to create what's next or to participate in what's next.
12:04
So it kind of alleviated that anxiety around, like, "I can't leave something until I have the next thing lined up," right? And then it also gave me the confidence to, to take that spell and extend it out into the rest of the year turned out to be more volunteering.
12:18
So I, I volunteered with a poverty research lab at Notre Dame that I had been involved with.

24 MINS LATER

36:13
Yeah.
8:12
Who am I if I'm not useful or needed or productive or working? Like, is it my own identity crisis? And do you hear this in your research?
8:23
The first thing I would say is you're not alone, right? I mean, I think especially entrepreneurs, people that build their own thing, you feel like you're heading towards freedom and then you end up like constructing a prison around you, right? It's like a gilded prison, right? that has the design and the mission that you wanted or whatever the metaphor is, but you can't escape it.
8:47
And so this notion of wanting to separate your identity from your work and how hard that is when you're doing mission-focused work and when you hang up your own shingle affects everybody.
9:01
And then this concept of feeling like you owe something to your employees, to your customers, to your listeners, right? Also, it makes a lot of sense.
9:11
And I think the narrative that I'm trying to amplify is that what if your business, your customers, your employees would be better off if you stepped away for a little bit, both from an employee standpoint, making the organization resilient so that it can run without you, like the get hit by a bus challenge, right? No, thanks.
9:31
And then...
9:36
And then, you know, like giving them a chance to kind of step up, also giving them Ryan coming back, feeling rejuvenated and maybe, you know, not as snappy or more excited about the work or, you know, able to take the business and their kind of tasks in the new direction.

25 MINS LATER

35:13
And I did mention, okay, do you have a spot or adventure circle that's on your list? And also, are you a solo sabbatical? Do you have to be solo for it to be a sabbatical or is there like groups of sabbaticals?
26:07
What are companies really getting out of this when they set up sabbatical policies?
26:10
Yeah, I think it's a great point in the sense that the best case scenario is that a sabbatical that doesn't require you to like blow your life up, doesn't require you to save up for 10 years is possible because your company values you enough to do it.
26:24
And so all of us who work at companies who are managers are also people.
26:27
So we're taking our people hat off and putting our company hat on.
26:31
So this resilience is just a huge piece.
26:33
Like having a company be able to withstand what they call key person risk One of the interviewees was like the principal and founder of this boarding school in South Africa.
26:42
And, you know, he'd been there from day one.

11 MINS LATER

37:36
Yeah, 2031 is not very far away, but it's going to be awesome for the folks in this room because everybody started nodding when you said that at 2031, right?
speaker_2UNKNOWN
8:12
[laughs]
8:12
... and I brought it along on the, on the trip.
8:14
And so I wrote and performed my first song in a place where definitely no one would know me, so that was, that was helpful.
8:21
[laughs] And so I think we're gonna talk about what you learned from this and some of the benefits soon, but I, but I want to start with some definitions 'cause I'm a nerdy professor and that's, that's where I go.
8:42
And so how, how do you define a sabbatical? So the definition that I think about is an intentional extended leave from your routine job.
8:52
So intentional, not that you have to have made the decision to take it, because most sabbaticals kind of happen to you.
8:59
But that once you're on sabbatical, you stay there, right? And so as soon as we leave a job, our new job is to find another job, right? It's, like, very hard to be in that kind of liminal state between careers, between jobs.

29 MINS LATER

speaker_2UNKNOWN
38:40
2031, right?

We value your privacy

We use cookies to understand how you use our platform and to improve your experience. Click “Accept All” to consent, or “Decline non-essential” to opt out of non-essential cookies. Read our Privacy Policy.