What Would You Do with 100 Days Away from Your Job?


What would you do with 100 days away from your job? It’s a scenario most of us could only dream of. Today’s guest believes it could be the key to living a more fulfilling and authentic life. DJ DiDonna is the founder of The Sabbatical Project.

In this episode of the Courageous Podcast, host Ryan Berman and DJ DiDonna discover that sabbaticals and courageous decisions can both serve as regret insurance for your future self. DJ also speaks on what it will take to make sabbaticals more equitable for workers of all pay grades, and the importance of taking time for yourself before you feel like you need it. It’s a thoughtful conversation that reminds us the importance of stepping away from our daily grind every once in a while to reset on our career and life journeys.

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DJ DiDonna  0:01  

What are some of the things that folks wish they were spending the time on? I talk about it as things that are important, versus urgent. We’re always spending time on urgent things. And what we’ve seen in the research is a lot of people who feel like they have permission to do something like this had that example early on in life. And so, what experience would you like your kids to have that you didn’t get to have?

(Intro music 0:25-0:44)

Ryan Berman  0:45  

I am guilty of being sort of a work-to-live guy. And it’s all work to live, live to work. I love what I do. Look, I’ve been around a while. It wasn’t like I started that way. I kind of, like many, went through life just trying to survive my first job. Stumbled through what I liked. Didn’t get a say in who my boss was going to be. Always love being creative. But I think a lot of people now are in this work-to-work space, like work-to-work, work-to-work. Fear, fear, fear. “Do I have enough? Can I make it?” And so, I’m fired up about today’s conversation. Who I met very briefly in Banff at the gathering. DJ DiDona, hopefully, didn’t blow the name there, who is an author, who’s an entrepreneur. And I call you the expert on sabbatical, which is an interesting word that I hope we talk about a little bit. And just to let the audience in, DJ, before we kind of get this over to you. What the heck does a sabbatical mean in your mind? Can you start there?

DJ DiDonna  1:55  

Sure. First of all, what I’d say is that I would be happy if we didn’t have to use the word sabbatical. I think it’s a word that people use because it lends a kind of prestige and a justification for a whole lot of things, most of which is recovery, or doing something that you want to do. So, we borrow that from academia. But our definition of a sabbatical, because there isn’t really one, is extended leave intentionally spent away from routine work. So, extended, meaning longer than a vacation. Ideally, measured in months, not weeks…

Ryan Berman  2:37  

Not a weekend? A long weekend doesn’t count?

DJ DiDonna  2:40  

Yeah, exactly. I’m a bit of a stickler on this, and not one of those ‘five-minute meditation equals a retreat’ kind of people. And so, I think that there is something important about the duration of time off. Listen, everyone who’s taken a sabbatical has taken a vacation, but they’re saying something profoundly different is happening. Intentional, so you don’t have to intentionally lose your job or one of the antecedents to taking a sabbatical. Most sabbaticals happen without your permission. A health crisis, or job, or relationship issue. But once you are outside of the scope of doing your normal work, you have to stay there. So, your routine job, when you lose your job is to find another one. So, staying in that kind of uncomfortable liminal space is what we’re kind of after.

Ryan Berman  3:31  

I have a terrible confession to make and it’s about America, so buckle your seatbelts on this one. I almost feel like… And, by the way, I have not taken a sabbatical. So, according to your definition, I would love to take a sabbatical. I’m still trying to design a life where I get to do what I love and I have enough free time now, but I’ve not under that definition taken it. But here’s my confession; I think, although I haven’t taken one, I’ve tried to live enough experiences where I stay interesting. And I’m worried that we’re not as interesting as we used to be because we’re so afraid, and we need money. It’s like Maslow’s hierarchy of needs, and I’m not the educator, you are, right? So, is that what part of this is? Are we so afraid that we’re going to fall behind? Or, how we’re going to look. I guess maybe it just seems like there’s so much fear in keeping up with the Joneses. Having enough money to pay for stuff. Maybe we could kind of go back. How did you land in this space, and then, how long have you been researching it?

DJ DiDonna  4:48  

Yeah. And I think you bring up an interesting point. I’ve heard a lot of our sabbatical interviewees talk about wanting to run toward something, versus run away from something. Wanting to make decisions from a place of love, versus a place of fear. So, I think you’re dancing around a core thing that’s going on here, and a core suspicion that people have about how they live their lives and how it could be different if even for a little bit. I came into this mostly running away, I would guess, but running towards some things, which is, I was like you. Besides our similar haircut, I had never taken any sort of extended leave more than, I don’t know, 10 days since high school. I was 33, and I’d started my dream company. So, I think similar to you as well. I was doing exactly what I wanted to do. We had a social enterprise that was helping create a credit score in emerging markets. So, how do you get access to finance, to entrepreneurs across the emerging world? So, I am making a difference, great company culture, all the external indicators of success. New York Times article, Harvard Business School cases, all that stuff. And I just wasn’t happy anymore. Burnt out. I think one of the silver linings of the pandemic is that we can talk about burnout even more than we could five years ago, which I think is pretty tremendous. But I certainly didn’t have the story that you would burn out from your dream job. And so, partially, it was me wanting to do some things with my life that I hadn’t had a chance to do. Partially, it was just not being able to kind of function at the level that I wanted to, and that I had done in the past. And so, I took that time off, and we can talk a little bit about it, but everyone’s vacation is different. So, it’s of limited use, I think, for people. And I came back, and I had a completely different perspective on work, and life, and meaning, and identity. And I was just looking around saying, “This seems like the world’s best drug. Where’s the information about it?” That’s what kind of started me down this journey.

Ryan Berman  6:59  

I don’t know. You telling me not to probe makes me want to probe. So, I’ll tread lightly here. How long did you take off?

DJ DiDonna  7:08  

I took four months off, which sounds like the longest time ever. And I think anyone who’s gotten a chance to do that realizes that it just flies by. And if you’ve ever talked to your retired parents, your grandparents, days just fly by when you don’t have anything to do. And so, it’s kind of scary in that way.

Ryan Berman  7:28  

When you say it, do you feel like you took enough time off or not enough time off?

DJ DiDonna  7:33  

So, I took enough time off to kind of jumpstart the process. I think that another misconception that folks have about sabbaticals is that you’re going to take time off, and by the end of it, you’re going to be 100% certain and confident in this new version of yourself. And I think it’s really about starting a journey to figure out what’s your authentic self about what do you really want to be? How have you evolved over time? And zooming out to get some more context about yourself, versus delivering a solution.

Ryan Berman  8:08  

And then, did you go into the sabbatical going, “I just need a break”? Or, did you go into it going, “I’m curious about why are we burnt out as culture”? What questions do you have going in?

DJ DiDonna  8:25  

No, I went into it basically in kind of crisis mode, triage mode saying, “What does it mean to burn out from your dream job? Will I ever be happy again?” That kind of cycle. And I also had a list of things like most type A people would, which is, “Here are all the things I want to accomplish; I want to be a yoga teacher, I want to do guitar lessons, I want to be fluent in this, I’m going to do rock climbing guide.” And the only thing I really did was recover, rest, heal a little bit. Did a silent meditation retreat, and I did this six-week long Buddhist pilgrimage in Japan. And the only reason I mentioned that is because I’m super excited that Japan has opened back up to foreigners for the first time in three years. And, I’m actually headed there with my partner in two weeks. So, to do another small portion of it.

Ryan Berman  9:16  

Is there any way you’ll bring me back some affordable Japanese whiskey? Asking for a friend?

DJ DiDonna  9:21  

(Laughs) I don’t know if it’s going to be cheaper there. Though the currency is down like 20, 25% since the last time I was there.

Ryan Berman  9:27  

So, let’s let the audience in a little bit on our conversation right before we started recording which wasn’t long, because I don’t like doing that, because I want to keep it real. But you did ask me one very pointed question which is have I been on sabbatical before? And the answer is no, but I’m intrigued by it. I’m intrigued by the idea of the benefits that could come from it. And I have my own fears. I’ve got, like I said, I’m the only one that makes income right now in this family. I’ve got two little kids under the age of 10. But I feel like on the other side of all that doubt and fear, I see the benefits that could come with just get away for 100 days, and be inspired, and almost slow cook yourself and marinate in what’s possible. Not that you would, but if you were going to take me down as one of your clients and you are going to coach me through this process, where do you start?

DJ DiDonna  10:33  

First of all, out of curiosity, what would you do if you had 100 days? What are some things on your list? Or, what are some feelings that you’d like to have?

Ryan Berman  10:42  

Yeah, this is why I shouldn’t let guests ask questions. Great. 

DJ DiDonna  10:46


Ryan Berman  10:47

I already try to make time to think but the idea of going, traveling, and you said Japan, I would love to just go somewhere where I could be inspired. I like putting myself in the middle of the petri-dish and feel inspired by these different places. I’d say I do think time matters here, so if I get 100 days it’s very different than if I had six months. If I had 100 days. So, let’s hear it here. You should know some Jewish, so that means I’m already 12% guilt at all times. My family lives 3000 miles away from here. I have been sort of dying to go do something just with my mom. It’s been I think since high school. So, three decades since I think we’ve done just something, the two of us. I made the choice to move 3000 miles away, that was my choice. So, I’d love to do something with her. Probably not the Japan trip, but maybe there’s a retreat or resort we could go to and just let the emails collect in some other place, and sort of, shut that part of the world off, my world off. I think those are the two. I definitely feel like I need some me time. But then, I also want to reconnect with a little bit of my past because I’ve just been so far away from it.

DJ DiDonna  12:16  

Yeah. Those are great things to start with. And I kind of answered your question with just how I would approach it. It’s planting the seed of what are some of the things that folks wish they were spending the time on. I talk about it as things that are important, versus urgent. We’re always spending time on urgent things. And spending time with family is a very common one. And if it’s not a common experience on sabbaticals, it’s a common regret that people wish they would have done. So, countless friends and interviewees who got a chance to spend that one-on-one time with family, or their own family. So, you mentioned you have two kids, and what we’ve seen in the research is a lot of people who feel like they have permission to do something like this had that example early on in life. And so, what experience would you like your kids to have that you didn’t get to have? Or, what experience that you got to have would you like to replicate in some way? And one of the reasons why I don’t like talking about what I did on my sabbatical is if you’re single, and have some disposable income, and time, you can do a lot of cool stuff that is not possible in many different stages of life.

Ryan Berman  13:27  

So you went to space, basically?

DJ DiDonna  13:31  

(Laughs) Yeah. Some would consider Japan to be like a different galaxy. But yeah. So, I think spending time showing your kids, giving them an education in the world outside of where they’ve grown up, or if you’re in the city being a nature. Those are more difficult things to pull off than it is hopping on a plane to Japan, but the benefits seem to be tremendous for folks and not in that situation.

Ryan Berman  14:01  

I do think, and this is like the marketer in me, If you come from advertising and marketing, you’re constantly looking at trends and insights. And I got to be careful because maybe this is just me, I don’t think it is. I do think we’re putting an emphasis on experiences over stuff finally. Going and seeing things for yourself. And I even think because of the pandemic, right? We’ve been so holed up that the money is now going, the disposable income is being spent on experiences. I think my wife have done a pretty good job with our kids. They’re travel ready always now, which is cool. Now, they probably like it because they get their iPad for five hours on an airplane. But I think we’re very intentional about letting them see the world with us. My parents didn’t really do that with me. We saw a couple of places. I had a great childhood, not bad in any way, shape, or form. But I want to talk about the health benefits. Not just the obvious ones like, well, stress relief. It feels like to me sometimes when I’m writing on something, and I need a break, and I go away, and then, when I come back to that project, the floodgates open up. I feel like sabbatical is kind of like that as well. Is there any research that says, “Yeah, that’s kind of what’s happening”?

DJ DiDonna  15:27  

Yeah. So, we’ve done the research, we’ve started that kind of process which is I’d spent a lot of my career working with social scientists to try to take research and make it actionable. Make it practical, versus just sit on a shelf somewhere. And so, when I had the experience I did, I came out and started looking for collaborators to say, “Here was my experience,” and anecdotally, I’ve spoken to dozen or so people that echoed the importance of this time off. Like, “What can we learn about this that can be more broadly applicable, and more importantly, kick off a new kind of branch or avenue of research on well-being an extended time.” So, I think you hit the nail on the head with one of the most important things that’s going on is people are having time to rest and recover and restore. With the always-connected environment that we live in, it’s impossible to pull ourselves out for any extended time. But what we found is that what we kind of termed as functional workaholism. So, people once they got outside of that way of working and living, they realized that they were very unhealthy in how they were living, they just couldn’t see it at the time. And this would manifest in things like people having stomach ulcers, or trigger fingers, or all sorts of physical health impacts that they had been to numerous doctors for. They had obviously mentioned stress and they kind of shrugged it away like, “I’ll power through this.” And then, within a month of kind of being in Bali, or being away, that stuff clears up. And so, first of all, there’s actual physical, tangible health benefits. And I think the second thing is just more of this opening of the aperture of perspective of what’s important. And what we found, we don’t have enough data to say this definitely happens, but people return with a more prosocial mindset. So, they care more about themselves, their small family community, the community around them, and then, oftentimes, the world at large. And so, by kind of subbing that work stress and intensity, and focus out, you can reset to say, “What do I actually think is important? How has that changed over time, and how can I use my time to work towards those things?”

Ryan Berman  17:55  

I think we’re talking about people’s awareness here. Are you aware that you kind of need a sabbatical? And I guess the question is, can you short-circuit people? Or, do you have to wait till it’s almost like you’re at a point of no return? You’re just so stressed out and freaked out. And, like you said, now you’re running from something, versus running towards something. Is there a sabbatical quiz I could take to see exactly where I am on this spectrum?

DJ DiDonna  18:29  

I feel like you’re seeing me here, but on our website we do have like a little quiz to kind of tell you about what sabbatical archetype you are. I have aspirations to add kind of a burnout indicator, and things like that on it as well. But I think one of the most important things that I’m trying to get to, and the purpose of this organization that we kind of founded the sabbatical project, is to make sabbaticals equitable for everyone. Which, in order to do that, they have to be paid, they have to have benefits, which means companies and governments need to get involved. But the bigger goal is to have it not be solving a problem. You have to get to a place where there’s an improvement or a solution for something. But more doing it before you need it, before it’s an emergency. If you wait to get to the point where you have a health crisis, or a death in the family, or job crisis, you’re going to have to spend a lot of your sabbatical getting yourself back on level ground, versus, I think to your point, when you describe taking a sabbatical, I’m not sure anything’s wrong right now. You might say, “Hey, listen, I built this business. I like doing the work that I do, and I work to live.” But the opportunity is how could that be better? How could you bring new creative insights into your work? How could you bring more personal energy and agency? Or, maybe it’s just your return exactly the same but you got to have three to six months with your family, or with your mom, or with yourself that can change what you want to do in the future. So, yes on kind of solutions, and then, I think the goal is to get people to just view it as a normal part of life. Just like summers are when you’re a kid. No one would invent summers if they were worried about the learning outcomes, or the stress on parents, or anything. It doesn’t do anything except from what I know, I know it’s just fun. And it is like a vestige from the pressure on the agricultural calendar, or something.

Ryan Berman  20:30  

Unless you blew it during the year then you’re in summer school. I love that point. I love that point. That summer’s whole point is to be summer, just be summer. It must be nice, by the way, because I think if you go to college, you get summer and if you don’t, then you’re just sort of like, “Oh, here we go again.” is that the strategy? How do you normalize sabbatical?

DJ DiDonna  21:01  

Yeah. It’s adding a story to how we think about life goes. Right. The predominant story, I think, in the arts so far has been hustle culture. And some CEO like Elon Musk running three companies, and sleeping under the desk, and things like that. And I think the pandemic has helped shatter some of those things where people are like, “Oh, actually what the hell was I doing driving to work? Actually, I don’t love this work, I’d rather spend more time with my family, or I’d rather live in a beautiful place.” And so, what I’m trying to do is help people know that there’s successful, thriving, flourishing, happy people that also just integrate periods of time off and rest and recovery in their life. It doesn’t have to be graduated from high school or college and work until retirement, if you make it that far.

Ryan Berman  21:53  

So, I don’t think this is as clear as I wish it was, but maybe you could help me through this. Because, to your point, sabbatical to date is this… I think for most people, and even as I say it, it’s a truth for me. I think it’s hard to change people’s behavior and belief systems. So, I feel like sabbatical is the bucket list. It’s the thing you want to get to, you really haven’t put a plan in place, by the way, to get to it. But you’re like, “I’ve got a bucket list, that’s on my bucket list.” But seeing my mom, when I get a chance to do that — and clearly I’m showcasing myself as a mama’s boy today —  it’s not a bucket list, but my bucket’s full. My bucket is always full when I get a chance to spend time when my parents, and that should be normal. I find it interesting, because then, I don’t know what the ‘aha’ moment is, but this sort of bucket list is a real thing. I wonder if that plays in sabbatical land as a way to trigger like, “Okay, how did you feel doing this one item,” versus like, “No, my bucket’s full. I got a chance to actually take some time away.” And again, I have the luxury of a life, though I am trying to design it, that I get to pick and choose where I work, and how I can work, what projects I get to work on. Is there anything in that that’s like what you’re trying to do? Just make, again, the benefits of this.

DJ DiDonna  23:19  

Yeah. I think how you’re describing it is… Listen, I think you’ve gotten yourself to a place where you have more autonomy over your schedule and your life than most people. It sounds like you still obviously have some kind of restrictions with income and being the sole earner in the family, and kids at a certain stage, things like that. And I think it’s just about getting a chance to do the things you want to do before it’s too late. And I remember one of the interviewees talked about she wanted to be a global traveler. She had never really been outside the country that much and wanted that kind of identity and that experience that she didn’t get if you would have got backpacking, or something. And what she found is that she had this bucket list and she kind of knocked a lot of them off the list. It was like hiking the Annapurna circuit in Nepal, yoga training in India, and all that stuff. And she’s like, “What happens is the bucket fills back up.” You have more things and you realize the bucket list doesn’t have to be this finite thing that happens when you’re on your deathbed, but it can really just be like, “Here are things that I think are important that I value now.” And maybe by doing some of those things, you realize that, “Actually, what’s more important to me is going off in this direction.” So, people have described it as bringing lessons forward from the future that you would have figured out later. Like, “I thought I wanted to retire and live in Bali, but I went to Bali and it’s not for me. Okay, now I can cross that off and think about what else I want to do.” So, does that make sense?

Ryan Berman  25:04  

It does. I love that. I think that’s what it is. It’s back to the future. Like, you’re going into the future, and you just pulling it into here and now. So, speaking of talking a little bit about the future. You have a pretty cool expedition coming up. Would you agree with this? You live in California, not that you’re in Southern California, but you’re moving to a pretty cool part of the country pretty soon. Can you share what you’re going to be doing and where you’re going?

DJ DiDonna  25:33  

Yeah, I’m going to Boston. I got a job teaching entrepreneurship at Harvard Business School. So, I went there for my MBA. And yes, it’s interesting. I think that, again, the goal of the organization, and the organization, by no means kind of stops or slows down with this. It actually, I think, gives the movement a bigger platform, and better ability to work with companies to do experiments on sabbaticals, and that sort of thing. But I think one of the most interesting things about this, and it’s something that I’ll share with my students in the spring and beyond, is the thing that I thought it was really going to launch me into fame and sabbaticals on the norm, I got pulled at the last minute by an editor, and it was kind of like probably one of the lowest points on this idea entrepreneurship journey that I feel like I’ve been on for the past four years. So yeah. I like to kind of caveat the good news with if you’re doing something entrepreneurial, and obviously, the word courage is like floating all around your head on the video screen, it takes courage and it takes the ability to kind of withstand tough stuff. And the journey can be windy, but hopefully, it trends in the right direction.

Ryan Berman  26:47  

What do you hope comes from this trip for you? Or, is part of this… Now that you’re in the sabbatical space is not trying to predict the future, and just sort of be at peace in the messy middle?

DJ DiDonna  27:01  

Yeah. Well, I have a really good quote I think from [Inaudible 27:06] about that which is; aspire to live the question as opposed to the answer. So, I think this is another segment of the question. And the question for me now is, I’ve always thought that I would like teaching, that I’d be good at it. I’ve done some guest lecturing. And some of the most fulfilling parts of the business that I started is seeing young employees, and helping mentor them, and get them along on their journey. And so, it’ll answer a question, maybe I’m not good at it, maybe I don’t like it. But at least I won’t have to say, “I’ll teach at my high school when I retire,” which was my current plan. And then, you get to retirement, and you’re like, “I hate this,” or you don’t make it to retirement. And so, I think it serves as answering some personal questions just around work, and what I want to do, what I’m good at. And I think for the movement, it’s huge. You’re there kind of at the seed of capitalism saying, “Hey, everybody. I know you’re talking about IPOs, and raising VC money, but I’m over here talking about the importance of the life of an entrepreneur and an individual.” And what things might help make that life better, what things might bring more creative ideas that will feed into entrepreneurship. And you’ll get closer to companies, again, to tell this story about another way to work, another way to function as a company.

Ryan Berman  28:29  

So, my visceral response to all of this, there was two instant ‘aha’ moments, and I don’t like one of them. I think one of them is probably the problem, frankly. The first one I like. The first one is I can’t imagine this being a bad thing when you get to collide with amazing minds that want to do more, and be better, and make the world a better place. And I’m not just talking about the students, by the way. I’m talking about the staff that you’re going to build relationships with, and they have their own ideas, and the collision of those ideas is going to be an experiment in itself, let alone, the fulfillment that comes from teaching. This is the part I don’t like about me, and I think this is probably part of the problem, is the multiplier. I’m taking time off, where my mind goes as an entrepreneur myself is the return on it all. I guess it’s kind of right there, right? My book’s called Return On Courage. But I don’t know if that’s the answer. The answer might be why are we so caught up in multipliers in the first place, versus just providing true fulfillment, and joy, and liking your life, and doing what you need to do? But is that a normal sort of logical response for entrepreneurs?

DJ DiDonna  29:51  

Yeah. Listen, I think we live in a society where the predominant story around success is bigger, faster, better, richer. And so, that makes a ton of sense. And I do think the purpose of doing these studies with companies is to try to figure out, “Are we actually sacrificing something when we enable our people to take time off? Or, is it net neutral, or is it actually net positive? Do you have greater tenure? Do you have greater creativity and better kind of recruiting effects?” And all that stuff. Yeah, I think my second reaction to that is, you might benefit from taking a sabbatical. When I took it, I had this definition of success. And it wasn’t wealth, or anything, it was about the impact that my company was making and how excited I was about that. But I think it took the edge off a little bit, stepping away from that and saying, “Oh, actually, one of the things I enjoyed the most was I took my mom on a train trip across Canada for her 70th birthday with her and her college roommate. And I bought a ukulele, and wrote my first song and performed at a bar in New Zealand.” These are things that just don’t get you anywhere. They’re not in my LinkedIn profile. And they have just resounded since then and had a huge impact on me.

Ryan Berman  31:15  

I think they both should be on LinkedIn. We’re back to where we started, though, on, like, there is something about “Do I feel interesting?” Because both of those, I think are like, oh, that’s cool. I love where you went. Not why you did it, where you went. How it all sort of unfolded. When I think about the work that I’m trying to do, the ‘aha’ moment I had was being courageous actually makes us happier. It doesn’t feel like it in the moment because we’re afraid, or we have doubt. And we all as humans are scared at some level. It’s not something we like to talk about, and it’s back to awareness. But I think most of us, maybe you can pull in some of your research, are afraid of something. And when we actually go through that and challenge ourselves, and usually what I found is the destination is being happier. That is where fulfillment probably plays. It would be interesting to see, as you go through your journey here, what are the three massive outcomes both on a personal level, and then, on a professional level from sabbaticals. Maybe you already have this data, by the way.

DJ DiDonna  32:31  

Yeah, I can tell you a little bit about it. As you were talking, I was trying to look back. I was listening to one of your podcast interviews today where you were being interviewed and the person was kind of pushing you on the definition of courage. And as you’re describing it now, I don’t know how or if your definition has evolved, but it feels like making a courageous decision, and I’m obviously thinking off the top of my head here, but it feels like that’s always going to be a decision that’s more towards your authentic self. So, it might be hard to quit a job that’s prestigious, but it’s more authentic. It might be hard to stop someone saying something bad to someone else, but it’s more authentic to who you are and who you want to be. And so, it feels like making a courageous decision is going to get you closer to who you aspire to be, who you are, who you are your deep core self. And so, I think there’s a lot of alignment with sabbaticals there. It enables you to kind of step back from the noise of how you’ve been living, or just the life and society around you and really start to be able to listen to that little voice inside of you, or that voice of something you used to love to do that you haven’t put a lot of effort into, like drawing, or, for me, it was music. And so, I think that’s one of the outcomes is people having more authenticity because they’re able to spend time doing something that feels authentic to them, and also, zoom out to even figure out what authentic is for them now. The struggle that I had was just because you started your dream job eight years ago doesn’t mean that’s going to be your dream job in eight years. So, how do you deal with the fact that you change over time, and that sort of thing? I think one of the other takeaways from coming back from a sabbatical is that people feel like they have more autonomy. So, they feel empowered. They have kind of physically and mentally more energy to make decisions and do things. But they also have more courage because they’re like, “You know what? I just did something that seems really hard and weird to people on the outside, and it was fun. And I came back better for it. And so, if that was fun, then what else am I scared of that I can try.” And so you see people that are willing to ask for raises, ask for promotions, potentially leave, try to start their own thing. So, I think that’s one of the big outcomes as well.

Ryan Berman  35:05  

It’s classic storytelling one-on-one. Like, Joseph Campbell here, right? It’s the hero goes on the journey and has to go on the journey, by the way. And speaking of that, let’s talk about your journey too a little bit. So, obviously, this show is about courage. Do you feel like there was a moment where you’re just kind of going through the motions, and when you sort of stepped out of yourself, you’re like, “Dude, come on. What’s going on? I know what I need to do, and yet, I’m not doing it.” And just to sort of answer the question you posed a little bit ago, I haven’t seen much that’s knocked me off my definition of courage, which is knowledge, plus faith, plus action. And I think there’s many times in our lives where we know what we should do when we feel it’s the right move, and yet, nothing changes. Nothing happens. It’s the leap that we don’t take. Is there a moment for you on this journey, or before the journey started that you kind of had a WTF moment?

DJ DiDonna  36:12  

Yeah. I think you probably heard me… You might have left here before my closing keynote, but I talked about this ice cream sandwich moment where I basically was depressed knowing that I needed to take time off and pull the trigger. And it wasn’t until I ordered two ice cream sandwiches delivery to my house on a Friday night while I was watching Bojack Horseman on the couch that I was like, “Okay, this is the straw that broke the camel’s back here.”

Ryan Berman  36:46  

Poor ice cream.

DJ DiDonna  36:48  

(Laughs) But I think stepping back a year before that, our head of Asia had quit suddenly. Our largest contract was up for renewal, and I basically had to move from Boston to Indonesia to save that. I was the co-founder, I had to kind of set up this relationship. And I remember reading there’s a Wordsworth quote; ‘to begin begin.’ And I was like, “Man, I know that I need to do something different here, but I have to start in order to get there.” And so, that kind of marked the point where it kicked off the next 18 months of getting the business to a place where I could step to the side. Figuring out how I was going to do what I was going to do. Renting out my apartment, all the logistics. So yeah, I think that, again, that kicked off the whole journey. And I do think about the monomyth in the hero’s journey a lot around this stuff. You had to be very lucky to just be in the position that you’ve always wanted to be in at all times and not need any kind of tweaking that is outside of the realm of normal careers.

Ryan Berman  37:56  

I love ‘to begin begin.’ It’s a great piece of advice that I feel like you could teach your echo or to say when you start your day. I always find myself saying courage is regret insurance. We talked a little bit about regret already. And, as you think about what deathbed material might be for you, is there a regret that you have that you feel comfortable sharing here, or uncomfortable sharing since it’s a show about courage, I guess?

DJ DiDonna  38:32  

Yeah. I think first of all, I talk about sabbaticals as regret insurance. And so, that’s funny because I do think that it’s a way to make your regrets actionable. To actually act on them. So, I’m realizing we have a lot of similarities on how we think about this, which is great. I think that I’ve always been opportunistic, I’ve always taken, I think, the path that most folks would kind of hesitate to take. Obviously, taking a job teaching at Harvard Business School is not like a tough one to turn. The path here has been very not lucrative and risky. But I think what I’ve learned in the past five years since my sabbatical is I just really struggle not to be like, air quotes, “productive.” And thinking about how much flexibility I’ve had in the last few years, I can’t imagine I’ll ever have this much flexibility in my days, in my life, and what I do. And I also haven’t given myself permission to take out and ride the motorcycle to watch the sunset, or take a half day off and go on a hike or something. And so, I think that’s the thing that I know I need to work on. And I think that’s going to be something that when you think about retiring, that’s the big sabbatical, capital S is retirement. So, it’s something to work towards.

Ryan Berman  40:08  

This might seem like a silly one, but I’m very curious in your answer here. How important is it for you to make a difference? And I know that sounds like the silliest question in the world. But, what about making a difference in your world just for yourself? Which could sound slightly narcissistic if you think about it, but is this a failure, this whole experiment, if you don’t make an impact at the level that you can?

DJ DiDonna  40:43  

Yeah. That’s a great question. Super insightful. I guess, I definitely have always been oriented towards making a difference. I think I went to Jesuit High School, and they really… Talk about service, and things like that. So it’s been like, you talk about Jewish guilt, I’ve got the Catholic Jesuit guilt. And so, yeah. Actually, what I don’t talk about very often is I took another kind of mini-sabbatical the year after I took my sabbatical. And I was trying to kind of right the wrongs of my first sabbatical, which I spent mostly, in my head and I was walking like 10 hours a day. So, just like in my head kind of thinking, and trying to process, and figure out what I should do next, and how to feel good about what I was doing. And the next one, I was like, “I just want to do something that’s fun. And I’m not going to talk to anyone about what I did, it’s just for me and see if I can just enjoy it.” And I ended up renting a Land Cruiser and driving across southern Africa for a month. Just camping on the top of the thing in the literal kind of Serengeti, and Kalahari, and things like that. And so, I did it. I did it for a month. I was able to. All I did was wake up and drive around look for animals, and it was awesome. And so, I think I’ve seen glimpses that that’s possible. But yeah, maybe the courageous thing for me, and this sounds like a humble brag that you’d say at a job interview. But the courageous thing for me is to try to do something that I don’t think really matters that much, and instead prioritize my family, or something like that in the future. So, it’s a good prompt.

Ryan Berman  42:22  

Well, I think humble brag gets a bad rap. And I’m leaving myself open here a little bit because I just think, as a society, we’re kind of broken. And how did it happen? Social media, I don’t think helped most of us. There’s good parts of it too. But we spend a lot of time scrolling other people’s stories, versus scrolling ourselves, and seeing what are we really made of. And maybe there’s a way as you continue to develop the program that there is this joy and fulfillment for a higher purpose. And then, also this being at peace with, like, put yourself in a position to humble brag. Not because it’s cool that you saw animals, although I’m absurdly jealous, that’s on my bucket list, but because you just needed it. You just had to go do it. And there’s personal love that comes with that that I think we’re missing right now. And I don’t know if I’m speaking, like, I really feel like it’s like 10% me, and 90% as an observationalist what I see. And so, I’ll keep you posted too, by the way on what does my sabbatical look like. I don’t know if it’s going to be six weeks, or a week, or 10 days, I will tell you our friend, Chip Conley has graciously invited me down. I’m so excited for that. And that’s five days. And for me, it might as well be six months. I’m going to go down to Modern Elder Academy in Baja and just have some me time and see where it takes me. Good start for me.

DJ DiDonna  44:06  

Let me know when you go down, I’ll give you my tips from having spent over a month there this fall.

Ryan Berman  44:13


DJ DiDonna  44:14

I think you’ve got me thinking. So, one piece of advice that I give to companies is… And I think, as you say, everyone’s focused on meaning. Like, you want to find meaning in your work, which I think is in general a great thing. But I also don’t think that most jobs can provide meaning. I don’t think that most companies do something that’s extraordinarily mission-focused or can be. And so, I think the opportunity for companies is to say, “Listen, we want this to be very meaningful for you, but we know that we’re a post-it-note company,” or whatever. Sorry, 3M. “And so, what we can do is we can give you a great job, good benefits, yada, yada, yada. And every four years, you get three months to do whatever you want. So, make your own meaning, do the thing that’s important to you because you can’t get all this stuff from work.” And so, similarly, I think, if you do think about work as something that helps you make meaning, that you find meaningful, and you find impactful, take that time off to say, “I’m not accomplishing anything. I’m going to go look at animals, I’m going to take pictures, I’m going to play music.” And you have to kind of believe that sort of thing does add value in the long run. Or, you have to learn that it doesn’t matter if anything adds value. I think that’s the goal. So yeah, thanks for prompting me to think about it that way.

Ryan Berman  45:40  

I like that too. And in some ways, you’re back to ‘to begin begin.’ You don’t have to figure out the end, you just have to start and see where it takes you, which is a great, great, great lesson. All right, final words. What you said was beautiful there at the end, but are you nervous about this endeavor for you? Are you excited about it? Give it to me straight.

DJ DiDonna  46:05  

Obviously, I want to do the students well, but I think I’m not going to… I don’t really get nervous until like the night before. And everyone’s telling me I’ll do a good job, so I’m trying to prepare, but yeah. It’s just an exciting, hopefully not just once in a lifetime opportunity for me. 

Ryan Berman  46:26  

Silly question. Because you take stages, I take stages. You’ve seen the TED Talk and whatnot. If you haven’t seen DJ’s TED talk, go check it out, guys. You’re going to be on a stage for a living again. You are. Does that excite you or make you nervous?

DJ DiDonna  46:46  

Yeah. I think similar to this conversation, right? Right in front of me, I’ve been working on a chapter that actually wrote down at the Modern Elder Academy. And part of me is like, “I’m locked in, I’m working on this. Oh, man, I got this interview, I got to prepare for it.” And, actually, what it ends up doing is prompting a lot of other kinds of thoughts and making connections inside of me. And so, I think that commitment device to kind of pack things up in whatever state they are of readiness, and then, share it with other people is a good practice. And so, I’ll never be as prepared as I want to be. I’ll never accomplish the lecture as much as I want to. But the cool thing about Harvard Business School is its case study method. So, you’re really trying to facilitate a conversation, versus tell people everything which I think is way more interesting to me. Probably is easier to teach in some ways for someone with my personality.

Ryan Berman  47:46  

DJ, thanks so much for coming on the show. You know what I might do if you’re cool with it, I got my little newsletter that goes out every Thursday, maybe we could do five questions in February. So, you have like a month or so under your belt. Is it what you thought it would be? I’d love to just have a little bow on this conversation as you go through your journey. And let’s stay in touch, and thanks so much for sharing today.

DJ DiDonna  48:10  

Yeah, happy to. Great to finally connect.

Ryan Berman  48:13  

Thanks, man. Be good. Thanks for tuning in to this episode of The Courageous Podcast. If you enjoyed the show, don’t forget to rate and review us on Apple podcasts so more people can find us. See you again next week.

(Outro music 48:26-48:44)

[End Of Audio]

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