DJ DiDonna
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Oct 8, 2026
#54 Big Time Off: Power of Sabbaticals Planned or Not | DJ DiDonna
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13:00Monique SchaferHOST
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?
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
A sabbatical asks you to say, all right, I'm going to take a beat or two before I start looking for a job.
DJ DiDonnaGUEST
And again, easier said than done if you're able to save and you have the kind of privilege to take a step back.
DJ DiDonnaGUEST
But ideally, if you're kind of saving and thinking about time off in the future, it'll be more possible.
DJ DiDonnaGUEST
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.
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18:23Monique SchaferHOST
that a sabbatical or that was just like a health thing that I used really well?
#54: Big Time Off: Power of Sabbaticals Planned or Not | DJ DiDonna
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DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
But ideally y- if you're kind of saving and thinking about time off in the future, um, it'll be more possible.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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
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44:23Monique SchaferHOST
... with, with their sabbatical, either going in, coming out? Just what are those first steps that people can take?
How To Take A Sabbatical With DJ DiDonna
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DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
And after like 90 days he printed the manuscript out, shredded it, um, prevented everyone from, anyone from reading it.
20 MINS LATER
Big Time Off What Kind of Sabbatical Do You Actually Need with DJ DiDonna
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DJ DiDonnaGUEST
So, um, achievement mindset, I think is, is the most common way to think about a sabbatical.
DJ DiDonnaGUEST
You're putting down your, like, um, your like routine tasks and you're creating all this space.
DJ DiDonnaGUEST
And so you want to fill that space with a bunch of things that are intrinsically motivated.
6 MINS LATER

Alan BriggsHOST
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.
DJ DiDonna: Big Time Off and Feeling Human Again
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Jeff PelaccioHOST
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.
DJ DiDonnaGUEST
I, I went to business school saying, okay, I'd like to continue the entrepreneurial journey.
DJ DiDonnaGUEST
I wanted to do something international, so something that aligned more with my aspirations versus my resume to date.
DJ DiDonnaGUEST
And then I wanted to do something that I felt like helped people and created a positive impact in the world.
DJ DiDonnaGUEST
I mean, Angie's List doing positive work, but something a little bit more in-depth than helping grandma find a plumber.
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Joe DeSeanHOST
You can contact him via LinkedIn or schedule a Zoom call via the link in the episode description.
How Sabbaticals Can Change Your Career | DJ DiDonna
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16:09Dart LindsleyHOST
Did patterns emerge in terms of what people told you about what they got from it?
DJ DiDonnaGUEST
One thing that was consistent across these interviews, I basically came back from my sabbatical having had a transformative experience.
DJ DiDonnaGUEST
Everyone I spoke to who had taken a sabbatical had some sort of transformative experience.
DJ DiDonnaGUEST
Being around academia, co-founding a company with academics, I wanted something more than just a blog post.
DJ DiDonnaGUEST
And one thing that, that surfaced in our research was this concept of peak life experiences.
DJ DiDonnaGUEST
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.
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Big Time Off: What Sabbatical Gives Back to Us with DJ DiDonna
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DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
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Why a Life-Changing Sabbatical Might Be More Possible Than You Think | DJ DiDonna
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DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
You're creating open space to f- to put into the story of your life things that you want to experience.
22 MINS LATER
The Life-Changing Power of a Sabbatical
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DJ DiDonnaGUEST
So I entered sabbatical land, as I call it, as most people do, which is unintentionally.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
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DJ DiDonna: The Transformative Power of Sabbaticals
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DJ DiDonnaGUEST
Well, I think, you know, back to the quote, I think a great company is thinking on more of a longer-term basis.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
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52:47Aarti ShahaniHOST
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?
Why Everyone Should Take a Sabbatical, SF Supervisors Approve Controversial Drug-Free Housing Rule
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DJ DiDonnaGUEST
Well, it's a bit of a bookend story because I had just been interviewed at WGBH in Boston about my company.
DJ DiDonnaGUEST
But after working there for seven, eight years, I was not feeling fulfilled anymore.
Why Everyone Should Take a Sabbatical
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DJ DiDonnaGUEST
I mean, what I try to do in the book is tell stories about people that have managed to make it work.
DJ DiDonnaGUEST
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.
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24:54Mina KimHOST
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?
The Benefits of Sabbatical Leave: Lessons from DJ DiDonna
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DJ DiDonnaGUEST
... 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.
DJ DiDonnaGUEST
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...
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1169: Tapping into the Transformative Power of Sabbaticals with DJ DiDonna
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11:03Pete MockaitisHOST
And so could you share some stories of some folks who did this and the realizations that they had?
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11:13DJ DiDonnaGUEST
One, there was a family that, that took a sabbatical on an island off the coast of Norway.
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11:19DJ DiDonnaGUEST
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.
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11:40DJ DiDonnaGUEST
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.
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The case for sabbaticals: Why businesses benefit when workers take ‘Big Time Off’
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4:49Tom EdwardsHOST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
So, you know, first of all, it's, it's about saying this is important enough to make some sacrifices.
DJ DiDonnaGUEST
However, what we found in the research is that, you know, smart organizations build the muscle of people leaving and returning.
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14:50Tom EdwardsHOST
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?
Why time away may be the future of work
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14:48DJ DiDonnaGUEST
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.
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15:17DJ DiDonnaGUEST
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.
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15:33DJ DiDonnaGUEST
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.
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15:54DJ DiDonnaGUEST
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.
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182. DJ DiDonna: How Sabbaticals Help Us Build Sustainable Lives
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Kathy OnetoHOST
You put them into some kind of archetypes and themes, and I thought that that might be helpful to characterize for people.
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12:10DJ DiDonnaGUEST
Yeah, so I looked at the data and pulled out some archetypes on how people typically use it.
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12:15DJ DiDonnaGUEST
I think now's a good opportunity to step back and just say, a sabbatical is not a tangible thing.
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12:21DJ DiDonnaGUEST
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.
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12:30DJ DiDonnaGUEST
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.
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12:45DJ DiDonnaGUEST
The things that I did on my sabbatical or what you did on yours might not resonate with folks.
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Kathy OnetoHOST
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?
The Leadership Recharge with DJ DiDonna
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15:27Jason BargerHOST
Respond to any of those statistics or where does that fit into any of the research that you've been doing?
DJ DiDonnaGUEST
It's all from the same river, right? So you can talk about the disengagement crisis.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
And I think in the past, the mark of a successful society or a successful upper class was leisure.
DJ DiDonnaGUEST
And so leisure use was this thing where if you made it, then you could have a country home and things like that.
DJ DiDonnaGUEST
And now the upper class are some of the folks that are most likely to not use vacation days.
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50:58Jason BargerHOST
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?
Why a Break From Work Might Be the Best Career Move You'll Ever Make
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DJ DiDonnaGUEST
... 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.
DJ DiDonnaGUEST
Um, I, I had no responsibilities, so I wanted to engage in this spiritual search.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
It's not something you put on the marquee, um, but was really kind of meaningful, I think, to both of us.
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177: DJ DiDonna – How to Take a Sabbatical without Breaking Your Business
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Brad JohnsonHOST
It's a really cool concept because I'd never taken it kind of that next level down.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
But, you know, when someone leaves for parental leave, they're gone long enough that other people have to carry the water for them.
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Exploring Liminal Spaces with HBS's DJ DiDonna
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22:40DJ DiDonnaGUEST
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.
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22:48DJ DiDonnaGUEST
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.
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How Time Away Can Change Your Future | DJ DiDonna
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DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
So I, I volunteered with a poverty research lab at Notre Dame that I had been involved with.
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DJ DiDonna - Founder at The Sabbatical Project
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Ryan BermanHOST
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?
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
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Ryan BermanHOST
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?
Why You Should Take a Few Months Off Work (Live from SXSW) from The Happiness Lab
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Laurie SantosHOST
What are companies really getting out of this when they set up sabbatical policies?
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
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.
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Laurie SantosHOST
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?
Why You Should Take a Few Months Off Work (Live from SXSW)
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DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
[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.
DJ DiDonnaGUEST
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.
DJ DiDonnaGUEST
So intentional, not that you have to have made the decision to take it, because most sabbaticals kind of happen to you.
DJ DiDonnaGUEST
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.
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38:40speaker_2UNKNOWN
2031, right?



