193: Sabbatical Planning with DJ DiDonna
8 Dec 2025 · 44 min
This podcast episode (host Jenny Blake; guest DJ DiDonna) explores sabbaticals — what they are, why they matter, and how to plan them. DiDonna defines sabbaticals as multi-week/month intentional periods (ideally months, not days) often used for exploration, healing and identity work (a "liminal" state). Key themes: detoxing from work and functional workaholism (how people burn out regardless of job type), common sabbatical archetypes (Explorer, Seeker, Achiever), and recommended timing (research and interviews indicate at least ~6–8 weeks to access deeper benefits; 4–6 months is ideal; a month can act as a shorter detox). Practical advice for business owners: plan sabbaticals in advance, design organizations to run without the founder, and treat shorter leaves as a gateway to longer ones. Episode includes personal anecdotes from both hosts about sabbatical experiences and references the Sabbatical Project and forthcoming book (Time Off / A Sabbatical Manifesto).
Questions this episode answers
May 30, 2023
Senior lecturer in the Entrepreneurial Management unit at Harvard Business School
2019
Time Off (a Sabbatical manifesto)
About 6–8 weeks (most folks need at least two months)
Chapters
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Spending a month is more fun than spending a week. But there's something deeper, deeper at work here and there's like a unraveling and a detox that takes longer.
This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host, Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.
Welcome back, Free Timers. Jenny Blake here with a very special guest today who I first heard on Jonathan Field's podcast sparked talking about how to take a life changing sabbatical. DJ dedonna is a senior lecturer in the Entrepreneurial Management unit at Harvard Business School where he teaches the required first year course the Entrepreneurial Manager. In 2019, he founded the Sabbatical Project to define, explore and research sabbaticals and he's currently working on a book based on that very research called Time Off. Well, a Sabbatical manifesto. Dj, welcome to the show.
How are ya? Great to be here.
Great. I love this topic. You know, it's just like peanut butter and jelly. With free time and sabbaticals and creating both can be a challenge. I often talk about free time. It's a muscle, it's a verb. And I would say sabbaticaling could be the same thing. It's even a harder muscle to build. It's like the biggest muscle to build in this arena.
Absolutely. I think it's one of the most important, but we can get into that.
So I want to start. Usually my last question with every guest is a permission slip. You've defined sabbaticals as measured in ideally months, not days or weeks taken intentionally and not necessarily to get something done that it's about a quest, oftentimes learning something. The part that I want to start with you on is what is the permission slip that you wish more people would give themselves around a sabbatical? Like the mental emotional piece, not necessarily the financials or the logistics.
I think that's actually easy, which is it's okay to not accomplish something on your sabbatical. And I would just preface that by saying that that's not how I thought either. So it's the most common sentiment around sabbaticals, but in some ways the least helpful to actually getting the benefits from a sabbatical.
Do you think there's something getting in the way first even of. I don't know, it's like we know the statistics that in America, people don't even use their full vacation time when they're employed for someone else, let alone when you're self employed. Like there's no such thing. You know, the business always lives in your mind, no matter when you're sleeping on the weekends. It seems like we barely give ourselves time to be fully unplugged for a vacation that's five or 10 or 15 days long, let alone something that's months long. What do you think is the gap of just believing that it's okay to take that time off in the first place?
To me, it's about the stories that, that we know of and the stories we tell ourselves. The predominant story at least 10 years ago was you go to school, whether that's finishing high school, college, whatever, and then you work until you retire. There's no part of a story or chapter of a story there where you take time away from work. The most socially acceptable time away from work you take is arguably grad school. Right. And I think the MBA is the most socially acceptable sabbatical because you're stepping off of this routine life and routine work to really explore for a bit. Right. Whether it's traveling, trying on different jobs and identities for size, with internships, opening up the aperture as to what kinds of jobs and cultures and beliefs are out there. To me, the biggest blocker is just, is this an okay thing to do? And that's kind of the genesis of the sabbatical project, which is I found all these instances where people, companies and cultures normalize time off, but that story wasn't being told. I believe through telling that story, it empowers people to do it and then also can work towards a more equitable way of taking time off.
I love that you said in one of your research papers that you've talked about sabbaticals as a liminal state. What do you mean by that? I know what liminal means, but how does it relate to the, the state we enter when we go on sabbatical?
Yeah, that makes one of us.
It's a quirky word.
One of the reasons why I wanted to Partner with academics originally. To do this four years ago is to take my personal experience, see if I was the only one, or if it was actually much more common, who had had that kind of transformational experience, and then connect it to what was already known in the fields of psychology and sociology and things like that. So liminal is this kind of fancy word for a time between something. Those times are scary. I mean, whether it's quitting your first job or leaving your startup that you founded and not knowing what the next thing is. And so having a protected liminal space where it's okay to be there is kind of the important thing. Right. So that's why people tend to call it like a sabbatical, as opposed to I burnt out or I'm having a crisis. Like a sabbatical is this kind of name and permission to be in that space.
On that note, my friend Penny and I, we call it the goo state. Because you feel sometimes when you're in a liminal state that you're just goo. You're like, who am I? You know, who am I? What is the purpose? What's the point of anything?
Yeah, I mean, I'll butcher the science, but that's kind of what happens when a caterpillar turns into a butterfly. The organism actually, like, dies. And again, I'm gonna get the science people shaking their fists at me.
But I'm with you, though. It's all good.
Turns into, like, a goo and then, like, reforms as a completely different entity.
You mentioned something really important. Burnout. It seems like, especially for business owners, maybe people finally give in and decide to take time off when they're so burnt out they can't even function anymore. And that strikes me as not exactly what you're talking about here. Like, by that time, it's too late. Like, it would have been great if you could have planned your sabbatic sabbatical a year prior to that, on one podcast, you even said, I wish we didn't even have to have the term sabbatical. What would be the difference between an intentional sabbatical versus like, an I'm so burnt out, I'm going to take the next three months off leave?
I think the difference is just how difficult it is to take, how much upheaval it causes in your life, and how much time you have to spend healing yourself before you can get into the goods. If you are flying along and you have to pull the emergency chute and the eject seat, that obviously causes a lot of tumult in your life. We found that kind of takes folks a lot longer to heal and get right as opposed to, if you think about it as like a regularly scheduled checkup, you don't want to wait until you have a major cavity or whatnot to go to the dentist. Like you have these regularly scheduled checkups, which I think is a more healthy way to enter it. So the easiest and most in some ways successful sabbaticals are ones where you don't have to worry about what job you're going to next. You don't have to worry about money. You know it's coming so you can plan your kind of life logistics and get yourself in order so you can actually just like relax into the time off. That's not to say they're the most transformative sabbaticals, but the kind of like emergency room visit versus the checkup is a good analogy for it.
Yeah, and it's like before you need a full on root canal. You know, I love the way you put that of. Yeah, that analogy between the two. I did take your quiz, which was really fun and I'll put the link in the show notes so you can see what kind of sabbatical taker you might be. And it looked like you can tell me if I'm wrong that the three outcomes for the quiz were explorer, seeker and or achiever. Are all three, would you say valid reasons for a sabbatical? I know it kind of goes parallel with a working sabbatical, free dive, sabbaticals and questers. Do you personally think one of those three types is maybe more exciting, rewarding or are they all kind of equal and wonderful in their own way?
I actually believe that it's more of a Venn diagram than like a three different paths you go down. I'm trying to like develop some master hypothesis around this as we put pen to paper on the book. But the least kind of evolved sabbatical is the one where we trade out our routine work for some other work. Whether someone's saying, listen, I've been wanting to write this book and so I'm going to swap out my job and just go straight into book writing mode. And I'm going to work just as hard, but it's going to be on something that's important to me, I think that's super important. And I think creating something that's valuable to you is really important. But people often forget to take care of themselves and they forget to actually explore and question whether or not that's the thing they actually needed to be working on. Exploring sabbatical is interesting because both at the beginning of your career, like my first chapter is about gap year takers, but then also towards the middle and towards the end of your career and your life, if you're not allowing yourself to step back and explore, then you're really kind of beholden to the inertia of what jobs and what community and what roles you've had in the past. As an example, if you quit and you say you're going to go on sabbatical, you tell people that you left your job. The majority of the contacts and interest that you'll get are, oh man, you'd be great for this job that's very similar to this, or you left that role. Oh, you'd be a rock star at this other company in the same role. And it's not until you actually step back and open the aperture that you can remember who you are kind of at a deeper level that you can explore who you want to be and not be beholden to you have been and really start to change your identity to hopefully a more true to self, true to core identity. I myself is more of this kind of seeker where I had these questions that I wanted to answer about myself and about my role in the world, especially as an entrepreneur, kind of stepping away from the company that I co founded. I don't think that they're necessarily better than the other, but I think it's helpful for folks to kind of dabble in the recipe of each of them.
And I love what you said about this Venn diagram. It's almost a dynamic Venn diagram. I see it like rolling forward like a wheel as the sabbatical goes on. That's a great point. It's not any one of the three, but people might toggle between those different modes. And I found it very compelling that I forget where I read it in your work, but that a lot of sabbaticals started slow, with extended time to heal, sleeping in, eating healthier, reconnecting with family and friends. So you asked me before we hit record the other day, you asked me if I'd ever taken a sabbatical and I'd been working at Google for five and a half years. I got permission to take a three month sabbatical when my first book, Life After College, was coming out and I genuinely did not think I was leaving. I didn't ask for sabbatical in order to quit Google. That was not my agenda. I truly thought I would come back at the end of the three months. However, per our earlier comments, I Was completely burning out. I was managing a very intense full time job with a complete side hustle blog activities, writing a book, and getting ready to launch that book completely in parallel while going to yoga teacher training. Okay, so this is me being bonkers in my 20s. And as soon as the sabbatical started, I made your next mistake, which is that I was immediately launching my book. So I literally like closed out at Google on a Thursday, got on a flight to south by Southwest on the Friday to go do book launch. And I had a lot of fun. I was having fun. But very quickly that side hustle became my full time thing for the next few months. And when I finally gave notice at Google toward the end of that time, I realized there's no way I can do both. I could see how crazy that would be and it wouldn't be fair to either project. When I finally made the decision to leave corporate, I was a couch potato for a month. I couldn't move. I was watching TV at 7am I was sitting on the couch, I was like, oh my God, what's wrong with me? Where have I gone? Like, oh my God, this is how I'm gonna be as an entrepreneur. Like, where did I go? And it was just years of burnout asserting itself, saying, no, you're gonna sit here and rest, you know, and it was scary because it was when I was leaving. But now I tell people leaving corporate, I'm like, you're gonna need a month at least of decompression time, if not more. And I'm so happy you addressed that in the idea of sabbaticals because often we're going crashing into one. And I think we might even be ambitious of like how blissed out we'll be in seeking mode. But no, actually you might spend some time just in R and R at the beginning of it.
Yeah, so much to unpack there. I mean, one of the first things is this concept of who you think you will be at the end of the sabbatical is not the one that you typically are. You might go away saying like, I just want to work on this project. And then you see all that's out there in the world besides what you've been doing. I haven't come up with a great analogy of this yet, but it's kind of like shopping at the grocery store when you're hungry. You're going to buy a bunch of different stuff when you're super hungry than if you're not hungry and you're actually making intelligent decisions about what you need. To have in the cabinet. That's awesome. I think you've also touched on the biggest fear that business owners have when rolling out a sabbatical policy, which is, wait, aren't we just going to pay someone and kind of give them a golden parachute to look for something else? Which I think is happening if the company has a culture where it's allowing people to get to the point of burnout. And it's not until someone burns out and has that time away that they realize that they were kind of not doing their best work and probably like zombie walking through the job. In our paper, we talk about this as functional workaholism, where from the outside looking in, you're actually performing relatively well. I mean, I'm sure you're getting great reviews and your colleagues thought you were doing good work. But as soon as you pluck yourself out of that milieu, you realize that the way you were working was unsustainable and like you were relying on a set of kind of unhealthy work habits that at some point would have failed in a spectacular way. And we're conditioned to work in that same way without actually analyzing what could be different. Right? I mean, we saw so many people in the studies that had health effects of stress like trigger fingers and gastro issues and stomach ulcers that they just kind of assumed was part of life as opposed to directly a result of the choices they were making or didn't know they were making or how they were.
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Around this piece around functional workaholism. It's like it was already failing in terms of my health, and I didn't know that until I left and certain health issues cleared up.
Yeah, exactly.
Where did they go? Oh, I had a thyroid condition. I had acne. There were things that now with the acne is a whole nother story. No doctor ever asked, what are you eating? Are you eating sugar? Are you eating dairy? No, they're just prescribed pills. But those types of things, asthma, acne, thyroid issues. It wasn't till I left and I could set my own schedule and I moved to New York City. I started being more active, walking more places. I didn't need any of the medicines again. But I wouldn't have known that in the moment. Like, if a doctor would look at me while I was working in that environment and say, oh, you need to reduce your stress, I would have laughed at them like, ha, ha, ha, that's funny. Okay, great. I'll, like, go to a yoga class. I wouldn't have realized how fundamentally it was affecting me.
Exactly. It's like the David Foster Wallace commencement speech. The whole this is water concept. I think how we're working is just something that we take for granted and not as a decision or not as like an ingredient in our life. You are kind of a blend of the five people you spend the most time with. So if all of your colleagues and friends are working and living the same way, it's just. It normalizes this thing.
Yeah, that's so true.
Which of the quiz kind of archetypes did you come up with?
Okay, so mine was, I'll tell you my exact results. I was 75% Seeker, 29% Explorer, and 15% Achiever.
Yeah, I bet if you had taken it when you're at Google, it would be the opposite.
A hundred percent.
Yep. Yeah.
Yes. If I had taken it at Google, I would have been almost entirely achiever. Just like that was my personality then, but also the reason as a business owner now it's so low on achiever is because I'm tired.
Totally.
I don't want to achieve anything. Like, I have so much responsibility as a business owner, as a breadwinner, I want less, give me less to do. So my sabbatical now would be so different than it was 12 years ago.
I mean, you've probably accomplished enough so that you know what's possible for you. And also you've seen. Seen kind of what you want to do and what you don't want to do like you're refining this equation over time. And my challenge to you, without knowing too much, I know from your interview with Jonathan that you actually have like a pretty strict amount of hours that you work per week. But the challenge for you and other kind of entrepreneurs and solopreneurs is can you build a business to the point where you can step away from it for an extended period of time? And like, I view that as the ultimate measure of success as an entrepreneur.
I love that idea and I love how Mike Michalwitz puts it in his book Clockwork that not only should the business not fall apart if you leave for an extended amount of time, that the real A plus is that the business can even grow without you. You can build the business, it can grow your team members improve, you get new clients, you onboard those clients. Like that's the real magic. Okay, I have a question around that. If somebody listening or me were to create a sabbatical, what is the ideal amount of time? So I won't just stick with the minimum. And if they check in on the business for one or five hours a week, does that negate the benefit of the sabbatical? Does it need to be cold turkey?
So one of the surprising things we found in our research is that folks would say it would take between six to eight weeks to have actually feel as though they were tapping into that space of their true self. So detoxing from work and really taking off that kind of identity from work and having life just feel like life, right? If you're not taking at least two months off, you're not really most folks dipping into that really good stuff. Obviously it can be different if you have a paid sabbatical from work and you know exactly when you're coming back. I think you can drop into that healing and exploration mode faster versus if you're pulling the chute and recovering from something. So I'd say at least two months. I would recommend for folks like four to six months, ideally. I don't want to discourage any companies or individuals for taking extended leave and by calling it a sabbatical or it doesn't qualify because I think that extended leave, anything above kind of two weeks or a month is a gateway drug. And it's going to make you realize that, oh, wow, that really passed by quickly. I can't believe it just flew by and no one really noticed that I was gone. Life kind of moves on and I think it gives you permission to have an even longer break in the future. Four to six months, ideally at least a month, just to give yourself a taste of what you could be getting.
Okay, thank you. Super helpful. What about the piece of having a minimum amount of work every week that's part of the regular work that's not part of exploratory, soul stirring work?
I'm of the belief that kind of work fills up the time that you give it. And also, since you've been on these kind of breaks, I'd love to talk a little bit more about that. But once you start to have something that compromise in your values a little bit, it can sneak up in interesting ways. So if you're traveling, booking some sort of trip, and they're like, but On Tuesday at 3, I have to be somewhere for a call. And it has to have Internet. And even though that might only take an hour, it's taking up a lot of your head space. And it's changing kind of what you can do and where you can be. And I don't think it's allowing you to kind of picture yourself not burdened with this thing. So I think that one of the most common mistakes I see people make is something like that, where they hang onto some sort of work. They hang onto consulting work that's in the same space to extend their Runway. But what they end up doing is kind of preventing themselves from going deep and actually, like, wiping the slate clean a little bit. That's not to say that you can't do this. I just think you're going to have results that are more akin to returning to work in a healthier way, more rejuvenated and refreshed, and less reimagining who you are, what work is and can be for you, which I think is invitation and opportunity. That is pretty amazing. So Jerry Colonna, for example, who's a former venture capitalist and coach, takes a sabbatical every summer for two months. He uses it to write. And so I don't think he's really transforming, like, his approach and who he is and who he wants to be. But he's also done this enough times that he understands that that cadence works for him. And it's not about, like, wiping the slate clean every summer. It's about having a healthy relationship between work and life, making space for his family and those sorts of things. So at different times in life, you can use these different levers of a sabbatical in different ways to produce different things. But I would encourage people to experiment with a month, two months without that before, to kind of detox and then layer back in and See how it feels.
Detox is such a good word for this. And as you were talking, it reminds me of the difference between snorkeling versus free diving, because freediving is one of your categories. But the snorkeling, you just have a small tool and you're bobbing at the surface and you can see some things and you're still gonna have a nice day, but you're not, like, swimming down into the depths of the ocean of your consciousness and then emerging under a new island, you know, or like, in some totally new place. And I also pictured this metaphor of skipping rocks across the surface. Because you're so right. Here's how my dad put it. Like, as soon as you have one meeting on the calendar, it's as if mosquitoes coalescing to a bare arm. Like, your whole day revolves around that thing and it's on your mind better than I did. Yeah, well, that's my dad. But also, like, if you're still checking email, I know how it goes. Like, if I check email once in a given week, that's supposedly vacation, those emails are on my mind. I'm not going to unsee them. I know who's written, I know who's waiting for me or who the team member is corresponding with. It kills it a little bit. It really does.
I love the snorkeling metaphor. And I think I would add scuba diving, not just because I like scuba diving, but the difference in how you can experience marine life when you're not on this clock of how long your breath lasts. You know, like, swooping down with a bunch of bubbles and commotion in order to, like, get a glimpse of a fish before you have to swing back up versus hanging onto a rock at the bottom of the ocean and watching, like, a manta ray clean itself. It's a totally different, different experience. And I think you just kind of opened up that metaphor for me, so I appreciate it.
Well, it was a collaboration, like how we built it together.
Thanks, dad.
Dad and dj. I want to come back to this achiever archetype because I can just picture myself if I were going to take a sabbatical, even if it was for a quest, even if it was with the most loose intentions, to go with the flow and discover myself in the world. I can imagine that I would have some expectations that, like, at the end of the four months or six months, like, oh, my gosh, I'm going to be renewed. I'm going to have brilliant new ideas. I'll have so much energy, and no matter what the Achiever in me would set some expectations for the sabbatical. And then I know that in my experience, even for a short vacation, I often talk about sliding doors. And I love that movie. But it's like sliding doors start playing out. There's the expectation of how my fantasy of how amazing it was all gonna be. And then there's the reality that sometimes the two don't line up. And the reality of it is like, maybe for a long time into the sabbatical, nothing is happening or it's not meeting the fantasy, no matter what the fantasy was. Have you had that experience? And what would you counsel to others to release some of that pressure of, like, what they're going to get out of it?
So it reminds me of a quote where he talks about living the questions, love the questions themselves, like locked rooms and like books that are written in a foreign tongue. And then perhaps gradually, without noticing it, live along some distant day into the answer. If you assume that this is the only time you're going to get to do this, and oh my gosh, it's such a precious opportunity, and if I don't come up with the answer by the end of it, you're probably going to be disappointed. There's definitely some folks who had light bulb moments where they started an electric airplane company, or the CEO of Impossible Foods had this kind of light bulb moment on sabbatical as well. But most folks, it's like opening a door that gradually kind of surfaces. Some learning, you might take an incremental change in your career, but you're not coming into your dream job. And that can be really frustrating and feel like a failure. If you live in a scarcity mindset where it's like, I only have this one chance, but hopefully what it's doing is saying like, oh, it takes a while to open the aperture. It takes a while to kind of be in this space. And this is the first step of many. So making it, as you said at the beginning, part of building a muscle around putting the things down in your life that you don't need to carry all the time is exploring, picking some of them back up and picking up new things. Not like a if I don't figure this thing out now, I'm doomed mindset. I think you have to live through that. I can't intellectually explain it. You won't intellectually believe it. You have to live through it and see that your tack changes a bit and that ultimately gets you closer to where you should be.
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What was the longest sabbatical you've taken?
I have not taken very long sabbaticals actually I think four months officially coming out of my sabbatical blended into starting the sabbatical project. It's debatable kind of how long that was. But email down focusing on kind of being present, on self development, on exploring the world. Four months which totally flies by. And also if you think back on any four month stretch in your life like right now, right. I can tell you that I picked up more things, I learned more, I accomplished more. I look back with more joy on those four months than any other span in my life. The density of memories and experiences as such during that time. So how about you?
And you did emerge with the sabbatical project. Not that you needed to. Not that you needed to, but I know what you mean. And they do say that as we get older we have less new experiences and so a four month period that is all about the new and going with the flow and serendipity. Really special. My longest, I don't know DJ for me, if I'm being truly honest, have I ever taken one? I mean I've been working since I was 11 years old. I started babysitting and like thinking about money.
And I was mowing lawns and working at my parents pizza restaurant.
Same thing.
Yes.
And then of course writing a book. Like in 2021, it was almost a working sabbatical in that for the first time in my life Since I was 11, I said, Jenny, you don't have to earn a dollar this year. I gave myself permission. I have passive income sources. And I did say yes, if there was like a big virtual keynote I could deliver. But I basically gave myself permission. I don't have to earn a dollar this year. I am going to use savings. I was writing free time. My husband and I lived in three different spots across five months. So we got outta New York City, we were in three different Airbnbs. And I have to say, I had like the best time. I was so happy. I was immersed in a deep work project. I was setting my own schedule, I had very few meetings, I was out of my normal routine and that was as close as it comes. But like I wrote a book, so who are we kidding? I didn't take time off. I think at one time I did a month in Bali again, I was working on a book, but for the first month I didn't do much. And I remember it's just so true how you need time. I talked about this in an episode called Crashing into Quiet Time, that even in Bali, and it's almost cliche now, it's like, oh, yeah, I went to Bali. It's not almost cliche. It is, but you could tell, like the New Yorkers who just arrived off the plane and then you could kind of tell who had just gotten there within the week. You could tell who had been there two weeks and you could tell who had been there two months. And I felt that in myself, like tightly wound and burnt out in week one. And then by weeks two and weeks three, I could just breathe. By week four, I'm wearing sundresses and like skipping down the street. And I remember one day walking down the street, bumped into a guy, he's like, oh, I'm heading to this cool meditation. And I made a U turn and just went with him there. And it was like that was the point that I could only reach four weeks in. I wouldn't have done it in week one or even week two. I would have still been my normal Jenny on vacation self.
Yeah, you're describing exactly what we're talking about here. I could have told you that beforehand, but I think you had to experience it and see it Yourself, like of course spending a month is more fun than spending a week, but there's something deeper, deeper at work here. And there's like a unraveling and a detox that takes longer.
And I find it takes two or three times longer than the mind will tell you it takes. So the mind will be like, you should be rested by now. And it's like, actually no, I'm going to need 3x that amount or 5x that amount.
Yeah, I mean the mind is trained on the data in to make that decision is how you've worked since you were 11. Right. And how you kind of see your friends working and things like that. So the fact that you've been able to kind of create this lifestyle and boundaries around how much you work, it's very countercultural. It's very unique to yourself. So that stuff takes time. And most folks who aren't picking their head off or their hands off the grindstone, they're not having those experiences. So it's intellectual. Oh sure, it'd be nice to take four months off, but it's not existential, which is I think what the results of the research and my interviews have indicated.
You know what? And you just gave me an aha moment because this existential social piece of free time, I had not put words to it. But you're right that I do try to live every day and every week and I try to be an advocate and a voice for saying in addition to like Tim Ferriss four hour work week, but I'm saying 10 to 20 hour work week and work in this really humane way that if you can, if you're self employed and you have time autonomy. But still I feel that it's countercultural. I feel that it's what you said in the sense that sometimes I get my rescue time stats and it says 10 hours and there is still a voice that's programmed that goes, well, that's barely anything or you're lazy or like if my business is going through a financial dip, I think, well, is it because I work this way and I have so much free time and am I just being lazy and I should work harder but I've worked too hard to get here that I don't want to unwind that and I want to find a new way and carve a new way forward that is less time and still abundant in the other ways. But those voices creep in because you're right, it's not the norm and it's not what everyone else is doing and sometimes it's hard not to internalize that and just think, am I just a nutcase? You know what I mean? Am I like delusional? I always have that thought. Am I delusional?
I think it takes a lot of time to deprogram. Because you know that the more you work, the more money you can make, right?
Yeah.
So it takes a lot of time to deprogram that. It takes time. And this is why I would encourage you, and I'd love to be a thought partner to try to figure out how to take an extended time away from this thing. I mean, Jonathan did what, one or two months away? I know Jesse Hempel from LinkedIn did as well. It's like it can be done. Even if you're a content kind of producer. You just have to plan it out two years in advance. Right. You can't just pull the shoot. So having to be a thought partner, as you think about setting it down.
For a bit, I love that. And I think a month. Cause even Jonathan said, I'll link to it in the show notes. He did this great one month post. Like after his sabbatical, he did this. How did it really go? And even in that he said a month is way too short. In like he had done all this work to create that month and carve out that month. Cause we both produce 12 episodes a month. So it means the month prior you're kind of cramming in 24 if you don't give a two year Runway like you're suggesting. And a month, that's just the detox. A month is just the detox. So totally I agree with you that it would be unfortunate to do all the work of preparing for sabbatical only to reach the end of it feeling like, oh my God, that was way too short. I'm not even rested, let alone like enlightened, like whatever else.
Yeah.
Last question before we wrap up. I love that you embarked on this research. Is there one thing that has surprised you most since you've started researching and working on the book that you didn't see coming?
We've already talked about the functional workaholism, which was quite surprising. I think how people work is not related to what they do. I had started my dream company. It was doing good in the world. They had a great culture, it was fast growth. And I thought that you burn out from something that you don't feel purpose around. Like you burn out from banking or consulting, but you don't burn out from your dream job. That's totally wrong. So people, it doesn't Matter kind of what they do for work. It matters how they work. That's what kind of like precedes burnout. One thing that I thought was interesting was, and this is a self serving comment is just when I took time off, I didn't know anyone who had done something like this. It was just kind of like, I don't know how to move forward. I have to do something. I will take time off. And through researching the book and doing these interviews, I've found just so many pockets of people from different cultures and people who have this traditions in their family where it's totally fine and acceptable. It's like there's these two tracks of folks, folks who kind of are just burning out and thinking this is the only way to work and other folks who are as successful, if not more than those folks and taking huge chunks of time on a regular basis off. So the whole point of the book is to bring these stories up to the fore so that they can actually be a part of the discussion around how we work. So I guess I kind of cheated and said too, but that's what I'd say.
If you could give fellow business owners permission to do something differently or drop something around all this, what would it be?
I think just how tightly business owners are grasping their roles in the company. And it might be correctly. They might actually have created a company that will fail if they step away from it. But more times than not, what I've seen is when you step away, it's not only the only way to kind of give yourself a break and renew yourself for the next leg of the race. It's the only way to see what works well and what doesn't. Without you there, you can't simulate it. I'm just reminded of a private school, boarding school entrepreneur in South Africa who stepped away. And it was the year before their 10th year anniversary, the African Leadership Academy. And he came back and the operations which he had kind of prided himself on went tremendously well without hiring anyone else. Just kind of empowering the folks who were already there, giving them stretch experiences. The fundraising fell off a cliff. And so he was like, okay, I'm not going to pick operations back up. I'm going to leave that to the folks who stepped up. And then my job now is to figure out how to fill this gap of fundraising so that it doesn't fall off a cliff when I step away. Because that's not sustainable. It's not a good company to create. So I would just challenge business owners to not consider themselves Successful until they've found a way that their organization can run without themselves in the seat.
That is so true. So we have permission.
It's almost the opposite of permission slip, right? It's like, wait, before you pass, go. One of my mentors, mbs, Michael Bungay Stanier, he said to me, maybe someone said it to him. So this is passed through the phone tree of entrepreneurs that whatever the founder is strongest at, the business will be the weakest at. And that is so true because it's the stuff that we hang onto and we hoard and we love and we don't teach anyone how to do because we're like, oh, I'm so good at that and I enjoy it. And then therefore, the business has this big void in it.
I love that. Yeah.
And thank you for the reminder of, like, just take a look at that stuff and that. I love the example you gave that. Okay, so something does go wrong while you're away. Most likely it's not the end of the world. It's actually highlighting the next area for development for the business. I love that he didn't just step back in. He said, oh, wow, they really need to develop this capability without me. So kudos to him.
Yep. Cool.
Dj, this is so fun. I love that you're studying this. As soon as I heard you on Sparked, I knew it would be great to get you on the show. So thanks for spending some of your free time with us. Where can people find you and keep in touch as you work on this book project?
I'm on LinkedIn, djddana and the sabbaticalproject.org we have a budding Facebook group. If folks are, you know, just want to get some kind of like real time advice and starting a LinkedIn group as well. So there's coaching, there's like free community. Yeah, just find us.
Amazing. I know it seems like this is one where what you're building, having a critical mass of people, as you said to say, this is possible. You can do it, kind of root for each other just to have the courage to take more time off than feels comfortable.
Absolutely.
Awesome. Thank you so much, dj. And big thanks to everybody who's here listening.
If you've listened this far, you get a gold star.
Thank you.
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