How to Take a Sabbatical without Breaking Your Business

Brad Johnson: DJ, welcome to the show, my man. Glad to have you here.

DJ DiDonna: Hey, great to see you.

Brad Johnson: Well, today, we’re going to get into a fun one, that’s very on topic for the show, Do Business Do Life. You’re getting ready to drop a book. In fact, as this episode drops, I think it’s going live, and it’s the whole concept of a sabbatical and how that actually can impact your business in a good way, both personally and obviously if you’re running a business. So, it’s a really interesting thing to think about because, like, taking more time off actually helps my business grow. It’s kind of counterintuitive. But let’s start with, like, what’s the difference. I’ve taken a lot of vacations over the years, but what’s the difference between a vacation, a sabbatical? How do you define those two?

DJ DiDonna: The reason I set out to do this is because I took a sabbatical myself, which we can maybe get into later, but every person who has taken a sabbatical has also taken a vacation. And all of those people are saying there’s something profoundly different here. Because it’s pretty obvious that a vacation is great. A longer vacation’s probably better, but there’s some aspect around the duration of time off and what it allows you to do, both accomplish but then also psychologically and identity-wise, like allows you to really separate from work, that is the difference. And so, when I got back from my sabbatical, when I was reaching out to other people who had done it, every single person was like, “That was a transformational experience,” you know, “Top experience of my life.”

And I’ve started a couple of companies based on academic research, and I was like, “There’s no research out here about this.” Anecdotally, people write a blog post here and there or tell their friends, but I feel like the magnitude of change was such that it required a deeper dive and some evidence behind it. And so, also, no one had defined a sabbatical. This term kind of comes from academia. The first sabbatical policy was set up by Harvard in the late 19th century. And so, I think people use the term sabbatical because it lends this kind of, like, prestige or gives you permission in a way that just saying something like, “I’m burnt out. I need to take some time off,” or, “I want to spend a couple months with my family,” doesn’t lend the same kind of, like, identity or permission.

Brad Johnson: Yeah.

DJ DiDonna: So… Go ahead.

Brad Johnson: On that note, in our conversation before we hit record here, you actually have done some academic research on, like, the time horizon actually needed to fully mentally unplug, to kind of be free for, like, “Wait, what do I actually want to do in life?” Like, what serves me versus me just going to the same company for 40 years because I need a paycheck? So, what’s the data show?

DJ DiDonna: Well, I think what happens over the course of most sabbaticals is there’s this first phase of healing, detoxing, however you want to think about it. So, both like the physical body, right? We’ve had people that have eczema, that have ulcers, that have trigger fingers, sleep issues. And so, giving time for your nervous system to reset and come back to a bit of baseline. And that will take up to six to eight weeks, depending on, are you coming out of a traumatic situation? Most sabbaticals are catalyzed by a relationship crisis, a job crisis, a health crisis, either yours or someone else. And so, if that’s how you’re entering it, it’s going to take you a lot longer to get back to baseline.

And then the next phase is usually this kind of like experimentation, exploration. So, to really do both of those justice, I feel like you need to take at least two months. I would recommend kind of four to six, if possible. I think having a summer, kind of aligning it to your kids’ summer break, or even if you don’t have kids, giving yourself an adult summer is a pretty good entry, but ideally longer. You’d be surprised how fast four or six months flies by, and frankly, how little time that is in the span of your career. You’re working 40 years from high school or college to retirement, 50 years. It’s 1% of your working life.

It’s a rounding error, but the memories and the inflection points and the pivots that you make from that time are what’s called peak life experiences, so up there in importance and significance in your life, with the birth of your child, your wedding day. So, like, investing 1% of your time over the course of a career can have such a meaningful impact.

Brad Johnson: Yeah. Well, and I want to visit, and you kind of touched on it earlier. Typically, a crisis is what is the inflection point for a sabbatical. And it’s interesting, your background, you actually were in fintech. Finance, I see it happen a lot. Lots of burnout because it’s just like more, more, more. More appointments, more revenue, rinse, repeat. I’ve literally cooked myself the last 10 years. You know, that’s kind of how. So, was that kind of what happened with you on the fintech side? It’s like, “I’ve grinded for so long.” It was kind of that crisis that took you this direction that then led to the discovery of like, “Wait, there’s more to this”? Like, what was that path for you?

DJ DiDonna: On the surface, that’s what it looked like. It was, I mean, literally on the surface, my co-founder, my business partners, they’re looking at me, I’m looking more ragged. I’ve got even worse kind of scraggly facial hair than I do now. Like, I just kind of let myself go, and I wasn’t really excited to go to work. And this is a job that I created the company. We co-founded it. It’s doing good work in the world. We had a great company culture. It was my dream job. And so, to burn out slowly from that and not feel like I could show up for my partners in the company and our customers, was really disorienting, because you’re like if you burn out from the life that you’ve always wanted to create, and I imagine a lot of your listeners, like, you finally created this life that you want.

You hang up your own shingle. You’re starting your own thing. To burn out from that is tough because then you’re like, “Well, if this doesn’t satisfy me, what will?” And so, that was one angle of what was happening for me. It was kind of like pushing me, pushing me out. But there was also this pull, from inside, from things that I always wanted to do with my life, parts of myself that I felt like I wasn’t honoring. You know, like the spiritual search, spending more time with family, spending time on my health and relationships, really getting outdoors and being like, “Well, how can this have a huge part in my life?” So, I think the burnout and the crises are the things that unfortunately often have enough weight to shake us out of our rhythm.

And the goal is that we live lives where shaking ourselves out is the norm, so we can actually be called towards something that we want to accomplish, something quieter that’s actually more important as opposed to urgent. I think that’s kind of like the spectrum that I think about. We spend all of our time serving the urgent, and the important kind of gets put to the wayside.

Brad Johnson: What was the most surprising thing for you personally? I mean, maybe give us a little context. How long was the sabbatical? What was kind of the structure? Where’d you go? And then I’d love, like, once we have context, like, what was the most surprising thing you learned about yourself during that time?

DJ DiDonna: So, before I answer that, I want to have like a little bit of a moment where, for everyone listening, when you listen to what someone else chooses to do on their vacation or their sabbatical, it can feel like it creates a little bit of distance because you might not be in that life stage, or whatever. And so, I would encourage folks to first kind of sit back and say, like, “What would you do if you had three months to do anything?” Right? A sabbatical is not a tangible thing. It’s like an empty space for you to put something you dream of doing. What would you want to do that you would regret on your deathbed or upon retirement, or not being able to tell a story to your grandkids?

And kind of like hold that idea in mind, because me describing my sabbatical might not be what you would design or what you have available. But what I did… So, I really wanted to invest in the spiritual side. I felt like it was important to me, but I was not putting the effort towards it. And I wanted to get outside and get outdoors, and so I did this six-week walking pilgrimage in Japan. You visit these 88 temples where the monk that brought Buddhism from mainland China to Japan. A totally bananas endeavor pushed me in ways that as, like, an avid outdoors person, I was like, “It’s just walking.” But it was tough. A lot of rain, a lot of rainy days.

Brad Johnson: How long was the walk again?

DJ DiDonna: It was about 900 miles.

Brad Johnson: 900 miles? In what timeframe?

DJ DiDonna: Yeah. About six weeks. So, like…

Brad Johnson: So, what’s that averaging a day?

DJ DiDonna: …less than a marathon per day. Yeah.

Brad Johnson: You’re averaging a marathon a day?

DJ DiDonna: Well, less than a marathon, yeah.

Brad Johnson: And I’m assuming this is not flat. This is…

DJ DiDonna: Yeah. Like some days with a lot of ups and downs, other days where you’re kind of on the ring of this island, and it’s not cool or interesting. You’re kind of walking alongside of a road, getting from one temple to another.

Brad Johnson: That’s wild.

DJ DiDonna: But in retrospect, I wouldn’t do it again. I’m glad I did it, but there’s no way I would do it again. But it was a great mix of physical activity, so getting out of your head and into your body. I think a lot of people, like, you’re like, “Oh my gosh, I’ve got time away from work. I want to be fluent in a foreign language. I want to write a book.” Like, all of these things where you trade some activity, and some activity that usually lives in your head, for some other activity, right?

Brad Johnson: Trading one stress for just another form of stress and pressure.

DJ DiDonna: Yeah. And I think primarily, like, living in your head, right? We live in our heads. We live in our computer screens. And so, getting outside and actually being in the weather and stretching your muscles and doing something physically demanding, I think, helps with the detox. Lots of research on walking and like the impact on thinking and health, and that sort of stuff. I don’t think anyone recommends walking for six weeks. And then also investigating something that is intrinsically important to me. So, it might sound like hard work. It was hard work, but it had this value of like, can I accomplish something this big? Do I want to have a more kind of spiritual, reflective life?

I’ve got the haircut for a monk, but I learned very quickly that like it’s just not my personality, but it’s nice to check that off the list. And so, that was like the marquee event I’d say for my sabbatical, like the one I really wanted to do. I accomplished it. You know, put it on the billboards. But a lot of the stuff that made the biggest impact in my life was very close to home. So, my mom was sick at the time, kind of cooking dinner for her every night, being there present with my family, where the prior eight years my company was based in Peru. I was living all over the world, traveling to emerging markets. So, that thing which doesn’t look impressive, you can’t quantify it, but that time was so valuable for everybody. And then other things like I remodeled my kitchen.

Brad Johnson: Hey, can I ask a personal question there?

DJ DiDonna: Yeah.

Brad Johnson: But like your mom, she was sick. Is she still with us? Did she pass away?

DJ DiDonna: No, she’s here. But it was kind of like an inflection moment where she needed to kind of get better. And it was one of those things where you could easily work through it. You could do the minimum. You could go visit. But actually, that presence and being able to step into the caregiver role is just not something that you can do when you have a job.

Brad Johnson: Well, and the other thing like in the big scheme, you compared the timeframe of the typical sabbatical, like 1% of your working life. I think it was Wait But Why. There’s a really cool blog out there.

DJ DiDonna: The boxes?

Brad Johnson: Yes, where it shows the percent of time you will spend with your children as a parent or as a kid with your parents. By the time they graduate high school, I think it’s like 75%, 80% is gone because you just got the holidays or the little pieces from there.

DJ DiDonna: Totally.

Brad Johnson: So, you bought some of that back with your mom, which is really cool.

DJ DiDonna: Yeah. Kind of like increase the size of the grid or whatnot, right? Like time that I wouldn’t have had. And time she wasn’t doing incredibly well, but it’s not at the end of your life, right? You’re getting some time while you can still take advantage of it and both be present. So, yeah, I think, and then small things, like remodeled my kitchen, which I think was good psychologically for me to get my Microsoft Excel fingers, like swinging a hammer and feeling capable.

Brad Johnson: There you go. Feel like a man for a few weeks at least.

DJ DiDonna: Yeah, until you see the finished product. But it felt good. And really, I think psychologically and emotionally, I was grieving a little bit of the loss of the realization I can’t go back to my own company. It demands something of me that I can’t give. And more importantly, it’s okay to have a dream job that you pursue for a chapter in your life, and that not be your dream anymore, and that not be the type of work you want to do. That’s like a part of the story, I think they don’t tell you. It’s like, “Chase your dreams,” and then what happens if the dream kind of shifts as we grow and evolve as people? You have to step back and say like, “Okay, what did I do well? What do I want to change? What should I do differently next time?”

Otherwise, you’re just going to keep moving forward, and the next incremental step you take is going to look a lot like the one you did before. So, it really gives you a chance to zoom out. Someone described it as a near-death experience where you’re like, you’re kind of zooming out like the Ghost of Christmas Past or whatever, and seeing how you’ve been living, seeing how you feel now, and really able to get a sight line of where you’d like to head next.

Brad Johnson: Yeah, I read a post a few years back. It was actually around the time that Triad was being formed, so call it five years, where I had left a long-term career as kind of an intrapreneur to venture out to be an entrepreneur. And it said there’s this common thing that happens for an entrepreneur, like we all have that fire. Like, living your dream, putting your own shingle up, whatever we call that. And then you go do it. And then if you’re not careful, you look up three or four years later, and you left the prison that was built by somebody else, and then you started building your own around yourself accidentally without realizing it. And I’ve heard a lot of entrepreneurs because it’s hard.

You know, you’re grinding. One of my entrepreneur friends, he said, “You’ll have the most freedom you’ve ever had, and you’ll never be able to truly go on vacation. Because when problems happen, guess who they call?” Right? And that was like the best explanation I ever heard. So, it sounds like this created space to truly ask yourself real questions that sometimes you want to ignore when you’re in it and give yourself the space to create clarity of what do I actually want. That’s what I hear kind of coming out of this as a theme.

DJ DiDonna: Totally. And it sounds silly, right? It sounds like I know what I want, or I can go to a cafe over the weekend and kind of reflect, or a weekend retreat. But I think one of the things we found in the research, I call it functional workaholism, where we talk a lot about burnout, which I think is kind of like an end state. Like, you have no more left to give, you know? But what I think is more present in the folks in our research and people I talk to is just this notion that the soup that you’re living in, like the water you’re swimming in, is, it’s stressful, it’s time scarce, it’s difficult. And so, it’s hard to fully make a rational choice and an authentic choice when there are so many demands on you and when your health and kind of abilities are detrimental a little bit.

 

So, really getting yourself to a place of healing, energetic, creative, want to go out and grab the world by its tail again, before making that next decision. Otherwise, you’re kind of grocery shopping while hungry, and you’re just like, “Oh my God, I’m hungry, and like, I got to get that snack,” and move on to the next thing.

Brad Johnson: I don’t know if your book goes into this, but I don’t know if it’s adrenaline fatigue or cortisol, where you’re constantly back to the soup or the water you’re swimming in, especially at the founder level, which is a lot of this audience that’s watching or listening, because they’re financial advisors. They’ve got to be great financial advisors. Oh, yeah, and also run a business while you do it with a good culture and operations that work and hiring the right people, and all the other stuff. So, did you find anything, or do you hit on that? Like, this fatigue where you’re almost… I love your analogy of grocery shopping while hungry, and you almost have to, like, chill out for a bit before you can actually, like, think straight.

DJ DiDonna: Yeah. And I feel super passionately about this because I was a founder, and I think writing a book is like founding as well, but solo founding. But the prison metaphor you talked about is totally right, which is the worst-case scenario, I think, in entrepreneurship, and I teach entrepreneurship as kids kind of starting out on their journey. Like, the worst-case scenario is that you spend too long working on the wrong idea, and so you don’t do the work upfront to say, like, “Could this work? Will this be as big as I want it to? And do I understand the signals that are telling me that I should stop,” right? And the second worst-case scenario is that it’s successful, but it depends entirely on you or majorly on you, right?

So, you’ve kind of created something that you can’t step away from, which I think is bad for you and your personal health when you’re going through it. And then also, you haven’t created something sustainable that can outlive you, which is bad for your employees, bad for your customers. And so, I actually view a sabbatical as a mandatory kind of litmus test for if you’ve created a sustainable, successful business. If you create some… And no entrepreneur’s taking a sabbatical in the first five years, right? Like, that’s not what I’m suggesting. If you create a business and you can’t step away 7, 10 years, fully step away for months at a time and have the business run, you’ve created a prison that you can’t escape.

And you’re not doing your employees a favor. You’re not doing your customers a favor. You’re not doing your investors a favor. And so, I view it as, like, a practice both personal health and humanity’s sake. But then also, is the company resilient? Do you have junior employees that can step up, have stretch experiences, and cover the ship in your absence? Do you know, like, can you truly know which parts of the business are not healthy when you’re outside of it, until you see it happen? And do you know which parts of the business actually run well or better without you in it? And then you can come back in and say, like, “I’m going to pick this up. I’m not going to pick this up. Wow, I really need to hire someone.”

And fundraising is a big one, especially for founders. It’s like, “I need to hire someone that can tell the story, that can do sales,” because founders often get saddled with doing the founder sales. So, you can know that theoretically all you want, but until you fully step away and see, “This worked, this doesn’t work, here’s how I show up at work and at home,” it doesn’t feel real.

Brad Johnson: It’s an interesting theory that makes all the sense in the world. It’s almost stress testing your business. I mean, it’s literally what we coach on all the time at Triad. A lot of advisors are founders that get here, and we call it the advisor-in-charge model. One of my friends said, “You know, most financial services firms I’ve experienced are built on an individual charismatic personality.” Not a business, a person.

DJ DiDonna: Totally. Yeah.

Brad Johnson: And so, what we coach on is actually how to move from that into business owner, into CEO, someday into board member, if it makes sense. But to me, it’s kind of winning in two ways. It’s the healing or the brake that you need as a human. And when the business is ready, like you said, not in the first five years when we’re getting the thing off the ground, but it’s step one of a stress test. In fact, I had a business coach, that’s exactly how he did it. He said, “I will take a sabbatical one year from now,” he told his team. He said, “It is our job to prepare the business to allow for it.” And so, it was almost like this project, so he could build it. And then the next year, he doubled it. He went from one month to two months. So, it actually was the force that made him create the business in a way that allowed for it, which was really cool to kind of back into it that way.

DJ DiDonna: Yeah. And I’d be really interested to hear how the business went, also how the perception and experience of the people left behind, because I do think it’s a collective project, and especially if you then take it one step further, which is, “Okay, I’m doing this. Now, can I help enable my employees to do it?” And so, it becomes this, like, equitable benefit that everyone gets, which makes the organization resilient at all levels, and then also creates a benefit that people are obsessed with. Their commitment to the company and loyalty and ability and desire to, like, recruit people to join, skyrockets.

And so, I think you’re describing the exact steps that I would take, you know, create something that’s manageable, plan in advance, see how that feels, and then expand it to the level that works for you. And you can kind of explore some of those deeper aspects of extended leave.

Brad Johnson: Was it Jim Collins that came up with the hit-by-bus test? I’m trying to remember if it was, like, in his book or if I picked that up somewhere else.

DJ DiDonna: Yeah. His thing about, like, the right people in the right seat on the bus is in my book, and I think I don’t know where the hit-by-bus thing goes, but yeah. I mean, like you have to. People will leave the company, right? And you, as a business owner, you’re not guaranteed another day, right? So, it’s your responsibility to make sure that thing can survive you.

Brad Johnson: Well, I love how you kind of waterfalled it. And by the way, this is another learning to be a great business owner and CEO. It’s almost like everything in finance trains you the exact opposite. So, you pass the first level, and then you get to the second level, and all the rules flip upside down. Because most advisors, the only reason they survived by jumping in the deep end was, “It all lands on me. I’ve got to do more door knocks, more cold calls, more whatever,” fill in the blank. But then that’s exactly what gets in the way of them scaling a team. They have to go from I to we. And so, now, if step one is, “Build the business in a way I can take a sabbatical,” great for you, empowers the team, kind of creates some space at the top for people to grow.

But now if you flip that, now you have to do the same for you, so now your team can run without you hit by bus, which is a more resilient business, which is awesome, because there’s cross-training that has to happen. You know, step in for a month while this person’s out. More systems. It’s a really cool concept. Because I’d never taken it kind of that next level down.

DJ DiDonna: Yeah, and I think it’s the most equitable benefit that I think you can give. I’m kind of modeling this theory of change around parental leave, which paid parental leave, we still have the worst coverage in all high-income earning countries. But, like, the US has made a fair amount of progress, 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. But when someone leaves for parental leave, they’re gone long enough that other people have to carry the water for them. Like, it’s not like a vacation where it just kind of piles up while you’re gone, and you do it when you come back.

And so, the work gets done, and you have some warning, and so you can kind of divvy out the work. But the people carrying that water don’t necessarily get that benefit, right? So, it’s like a one-way, you take care of another person during a time in their life that they need help. Whereas a sabbatical, like, you carry water for someone, and then you’ll get that later, right? And so, it makes it actually exciting, like I’m carrying, I’m doing this work for so and so, and then in three years they’ll do it for me. So, it builds a camaraderie that I think is pretty unique among benefits.

And the other thing, I worked with this financial advisory firm called Brighton Jones in Seattle. And the founder, his father passed away when he was early, when he was really young, and so he wanted to have this experience of spending time with his kids before he got too old. So, I think they had three kids, and they spent six months traveling around the world. And then he got back and said, “We’re making this, like, not only available to everybody, but mandatory.” They have something like between 100 and 200 employees. And especially in financial advisors, as y’all know, it’s like you want to have these long relationships with your clients, right? And if you’re in a bigger firm, if you only have a relationship with one financial advisor, then that person leaves and they take all their clients with them, right?

Or if that person gets sick or goes on leave, like, then the client is dealing with these other advisors who they’ve never met before, and they might not trust as much. So, for both parties, the company and the customer, it’s not great. So, by having this policy that was equitable across the whole company and then also made the company more resilient, made the customers served better, and then had those people want to increase their loyalty to stay at the company, because they’re like, “Listen, every 10 years I get six months off.” So, it kind of serves all needs in a cool way.

Brad Johnson: Well, being a guy that’s coached for 20 years in financial services, one of the biggest enemies to scaling a team is the old saying, if you want something done right, you got to do it yourself. And what you just hit on that the advisor doesn’t always see is that thinking stunts their growth, building a team, but even worse, they serve their clients at a lower level. Because if they go on vacation ever, now their clients have one person to call that’s not there that they email, they get an out of office. And so, a team-based approach in finance, which is what we coach on, Triad advisor model, there’s actually three different advisor hats, and it’s more like a pod, exponentially better feedback from clients because they’re served while that advisor is in appointments, instantaneous, high-level, team-based approach to a financial plan.

And what happens when done over time, instead of the sales funnel being market, sell, market, sell, the backend becomes the sales funnel as well, where it’s sell, serve, sell, serve, and they’re telling their friends about it, you know? So, it’s bringing referrals on the other side. So, a million percent what you just said, building the model in that way, but creating the constraint that forces it actually ups the client experience. It doesn’t decline because you’re on a six-month sabbatical. I haven’t seen people do it to that level, but I’ve seen people build teams with like, “Cool, I can go to the lake house for a month. This is nice.”

DJ DiDonna: Yeah. Totally.

Brad Johnson: Any other learnings from that case study right there that were surprising for you?

DJ DiDonna: I just, I feel like companies talk about creating company culture, and we’ve seen it over the years where, like, you put a ping pong table in the break room, or pizzas on Fridays, or something. And when I was there interviewing the CEO, Jon Jones, they had like a slideshow from someone that had just gotten back from sabbatical. And again, because it’s equitable, it’s not building resentment because it’s available to everybody. People were excited. They’re sitting there, they’re watching, they’re hearing about how it went. They’re asking about best practices on how to do it. So, it created this company culture that I think most folks would dream of because not all companies can give you, like, mission and purpose, especially the younger generations. They trade purpose, flexibility, mission for salary all day. And so, most companies can’t give an inspiring mission, right?

Brad Johnson: Did you say, like, just to understand, because we’ve got some advisors out there like, “Interesting idea. Sounds tough to pull off,” they’re kind of like debating in their head right now.

DJ DiDonna: Yeah.

Brad Johnson: What was the track? Was it 10 years earn six months’ sabbatical?

DJ DiDonna: Yeah, if memory serves me right, it was something like 10 years, six months, or maybe 10 years, four months paid, and then you can add two months unpaid or somewhere in there.

Brad Johnson: Okay. So, that was my next question. So, the company paid for four months of it, which is just you get paid your salary over that four months, but they’re not paying for the actual sabbatical, are they? Or they’re paying for the trips, and whatever they do?

DJ DiDonna: Yeah, and I think from my research, listen, people, if you can hold their benefits and hold their job, most people are like, “That’s enough. I’ll save up,” right? I think if you can give salary, partial salary, that’s where it really starts to become more possible for many people and equitable because at the end of the day, like you’ve got a mortgage or you’ve got rent or you have these kind of recurring costs, and it’s going to cost you more, obviously, to be somewhere else. And so, best practice is some sort of full pay, some sort of pay. But you know, at least kind of benefits and holding their job. But just to wrap up that thought, like the idea that people want mission and purpose, and you can’t always supply that at your job, right?

By giving them the gift of time to do what’s meaningful to them, you’re able to kind of like keep folks happy and build culture, and it doesn’t just all rest on the type of work that you do because not all folks are as passionate about the things that we start or that we care about, right?

Brad Johnson: Yeah. And interesting aside, I’m just thinking of like the ancillary benefits here, in finance, I mean, a lot of groups say this, but finance is such a relationship business it’s like, “Do I trust you to manage my million dollars that I saved my whole life or my five or whatever the number is?” And also, most advisors are trying to help their clients towards an end destination of a retirement, which is a form of an extended sabbatical, some would say. And so, the more you’ve kind of lived it, walked it, it’s like I don’t just say it, I do it. I believe it. And I want to help you on that same path.

There’s so much synergy there where, I mean, everybody in finance loves to talk about trips and travel and restaurants and cool places to check out because a lot of their conversations day to day is they’re helping other people do that. So, I feel like you’re almost doing market research that you get along with the sabbatical in our space. Do you see other side benefits?

DJ DiDonna: Yeah. And also, I think the role and the responsibility of the financial advisor, in my mind, is to help people live a good life in addition to like feel less stressed out about money and feel more permission to use it and to live a good life sooner as opposed to pushing it all to retirement. Because the odds that both you and your partner make it to retirement healthy, able to travel, like your mind is all there, right, like the odds of both of you make it there and get to do all the things you’ve spent your entire life pushing off to be able to do is not a great bet. And so, the idea that you can help your clients and help yourself pull some of that retirement forward in little chunks and think about it responsibly from a financial standpoint.

Like, save for five years to be able to allow yourself to do this. Obviously, no one or very few people can take a sabbatical tomorrow. But what are you doing in 2031? And that’s part of your goal. Like you are saving a little bit more to do something that’s important to you, and then you’re ensuring that you’re not going to have as many regrets when you get older because you actually are able to do stuff that’s important to you sooner.

Brad Johnson: Yeah. You hit the word regret earlier, and I wrote it down over here. And Jeff Bezos has this concept of regret minimization. It’s like what do you want to make sure you’re lying on your deathbed and kind of the final thoughts going through your head, kind of reflecting back? What’s the stuff you want to make sure you’re not thinking about or regretting? And it’s interesting just to tie a personal story to this and the concept of your book, which by the way, I don’t think we’ve mentioned the name, Big Time Off. Officially, I’m not sure exactly when this will drop, but July 21st, 2026. My wife had one of those regret stories, and it was actually her grandma who, lifelong Catholic, taught at a Catholic school, like go to mass two, three times a week sort of Catholic.

And her mom, of course, grew up Catholic. My wife went to Catholic school. Her grandma didn’t make much, but she was a product of the Great Depression, scrimper, saver, like cash in coffee cans. And the trip she talked about as a widow, because she lost her husband kind of early, is, “I want to take my whole family to Italy to see the Pope.” And it never happened. And her mom today still regrets, because she died with over 60,000 in the bank, and it ended up just getting distributed to the kids. And here’s the reason it never happened. There was never a perfect time. This kid’s got a sport. That’s going on.

And I’ve seen that to be one of the biggest thing that gets in the way is you talk about it, but you never take the action of like, “One year from now everybody’s invited. Here are the dates, and we would love for you to be there, but if you can’t, that’s okay. But we’re going.” Like, I’ve just found like as long as you give enough space on the front. And so, in turn, I saw this story play out. I’m like, “We are not repeating this story ourselves.” So, 2018, we took our full family, so our family of five, Sarah, myself, our three kids, and her parents to like an epic… It was only three weeks, so I guess it’s a vacation, not a sabbatical by your definition, but it felt very healing.

DJ DiDonna: Yeah. Bigger vacation than most Americans will take in their life.

Brad Johnson: And it was magical. Her parents still talk about it. We still talk about it, and there are just these lifelong memories that I will treasure until the day I die. And there’s the piece of me that I was like, it feels very fulfilling to know you won’t have myself with that regret, my wife with that regret that’s kind of repeating the narrative you don’t want to repeat. So, I love that frame. Are there, like if you were selling sabbaticals, are there other things that you would just love to speak to the audience and say, “Here’s some other things to think about so it’s not just a cool podcast you listen to,” and you’re like, “Oh, that’s cool,” and then five years from now you didn’t do anything with it? What are thoughts there?

DJ DiDonna: Yeah. No, listen, I love that story, and tying it back to the concept of regret minimization, I talk about as regret insurance. So, it’s like ensuring that you won’t have those regrets. And part of that is doing a bucket list trip, having a memory that you talked about, our folks in our research talked about, again, having a peak life experience. So, you created a peak life experience for everybody involved that they will talk about for the rest of their lives, at the cost of what? Like a few weeks’ vacation and however many thousands of dollars. Like, what’s the cost not to do that? Like, what would someone pay on their deathbed? You miss some kids’ sports games or a tournament, but you’ve literally created something that will be a key memory in all of those people, all those people’s lives.

And so, again, I would encourage your listeners to, like, can you go to a cafe over the weekend by yourself, no phone, no music, just journal, and be like, “What are the things that I really would want to have done in my life?” And just allow yourself to imagine wildly, right? And just write them down. Like, you don’t have to do them. Just write them down. And then I think ask yourself like, “How would I do these things? Are they possible? How much do they cost? How much time would they take? What are good inflection points in my kids’ life or my spouse’s life,” or your own life, to say, like “When my kids leave, like empty nester, my wife and I are going to take a renewed honeymoon. It’s going to be three months, and we’re going to plan for that,” right?

So, I can talk about all the findings from the research around like increased confidence and creativity and perspective and health and healing, but at the end of the day, it’s about being more human and going out and getting some of the things that you want to that are meaningful to you, and giving that gift to the people in your life as well, whether it’s being in service to friends or family, because you have more time flexibility. Or a funny story from the research where a woman whose husband was a lifelong trial lawyer, but he always wanted to write the great American novel. He studied English in college. They got married early, started having a family. And so, he took three months off.

And during those three months, he got to walk his two girls to school, he got to be home for breakfast and dinner every day, which was very rare normally. And he just went upstairs and started writing. And after about two months, he just tore the manuscript up, threw it in the trash, and was like, “Nah, I don’t want to do this.” And went back to being a lawyer. And you would think that that would be a bummer for him, but he was like, “Great, I got to give it a shot.”

Brad Johnson: Regret minimization, check. Didn’t want to actually be an author.

DJ DiDonna: And his wife was like, “I didn’t have to hear him b*tch about not getting to write a book.” And his daughters were like, “I got to see my dad.” And his daughters have gone on to take sabbaticals with their family. And so, it’s just this squishy thing where, as you said, there’s never a good time. And so, I think the only thing we can do is try to be as concrete as possible about what are our big kind of life goals, priorities, wish lists. And they don’t have to be some crazy accomplishment. Like, Elizabeth Gilbert talks about how saying “Find your passion,” is intimidating, but if you say like, “What are you curious about?” it’s more accessible, right? For me, it was like reinvesting back in music and creating music and singing.

It can be like pottery. It can be getting yoga teacher certified or scuba dive certified, living with your kids in another country, putting them in a school in another country, and giving them that cultural experience. So, that’s the gold at the end of the rainbow. And I think by truly having the idea and planting that seed in your mind, it can blossom. But giving yourself that permission to view it as a possible life you could live.

Brad Johnson: Well, it was interesting because I was kind of feeling like I was finding a theme in these sabbaticals where the place mattered, where it was like it’s got to be, obviously, you went to Japan. My closest thing to a sabbatical would’ve been Italy. Just magical places that were kind of bucket list sort of destinations, maybe new culture. But the story about the lawyer you just told, he actually sounds like he just hung out at his house for two months.

DJ DiDonna: Yeah.

Brad Johnson: So, maybe place doesn’t matter as much. I know it’s a variable, but how’d you see that play out?

DJ DiDonna: Yeah, I think best practices for getting the most juice out of a sabbatical, like duration, so like how much time can you create disconnection, how disconnected and unplugged are you, and experimentation. Like, are you actually trying to live out different lives, like give living a different way a real shot? That disconnection piece can happen geographically. I think getting to another time zone, getting to another culture, where even crossing the street or going to the grocery store feels like new and interesting, is really helpful. It’s like a shortcut. It’s like a hack. But so many inspiring stories are from folks that come from more modest means or have a limited amount of time or constraints, because aligning, can your partner take time off while you’re taking time off?

Stories where people’s kids talk about these like daddy weekends or mom road trips where they’re going to visit, like a presidential library four hours’ drive away. Like, getting one-on-one time with each of your kids, which is difficult, right, but is really special for those kids. One of the people in the study lived in San Francisco, and she wanted to kind of volunteer, see what is happening in the city, so she started volunteering. She started swimming out in the bay, things that allowed her to experience the place that was her adopted home in a way that solidified it as like, “Oh, this is my home now. I’m plugged into civic organizations in a way that you don’t have time to do, most people don’t have time to do with work.”

And really being like a good citizen, right? And a good person, not just a person that treats the city like an ATM or like a temporary stopover. So, I think I’ve got a whole chapter on that in the book, like more kind of modest sabbaticals, and how you can take the most juice from it.

Brad Johnson: Sabbaticals on a budget, is that the name of it?

DJ DiDonna: Yeah. And your story, I think, is a great example, which is you got to see how different a three-week trip is than a week or a two-week trip.

Brad Johnson: Yeah.

DJ DiDonna: And then imagine if you’re able to do that, and then also have like a little bit of time for just you and your wife or your family. You also throw in like a weekend where you’re on a retreat or something. And then two, three months disappear pretty quickly, but like the kind of magnitude of the change and the things you’re able to try is increased, so.

Brad Johnson: So, I love that. I’m a very, like, the way my brain thinks is systems and logic, which my wife is not sometimes a huge fan of. So, if I’m creating the variables that you started to see for themes of a great sabbatical, time unplugged, disconnect, I think you said, how’d you define that one? Just time?

DJ DiDonna: Yeah. Well, so duration, there’s time, disconnection, there’s an element of time.

Brad Johnson: But disconnection, like, I could take an eight-week sabbatical, but if I’m checking emails every day, that’s not a sabbatical. I’m not disconnected.

DJ DiDonna: Yeah, exactly. So, disconnecting from work, I’d recommend folks you have an away message that’s like, “I am gone doing family stuff. I’ll be back on August 2nd. Every email will be deleted between now and then. Shoot me an email on August 2nd.”

Brad Johnson: Hey, back to stress testing your business. Hey, they’re being forwarded to this person who will handle it while I’m out. Now, you’ve literally passed the hit-by-bus test.

DJ DiDonna: Yeah. And one of the CEOs I’ve worked with, I think, had the gold standard here, which he said that like, “I’m deleting the emails. I’ll be back on this date. If it’s important, like, here’s my contact person,” right? And then the contact person has the bat phone. And if he needs to be called in, they will call.

Brad Johnson: Like a death in the family. Like, this is really important. You need to know about it.

DJ DiDonna: Totally. And so, he had that person who works in the business, and he was like, “You can make all… I bestow you the power to make all business decisions but for X, Y, Z.” And then he had another person that was kind of from his personal life to serve as that firewall as well, and just be like, “Hey, I want to protect this time with my family.” They spent like a month in France and then were back home around Boston after that. And he’s like, “I just want to have this time where I’m just not thinking about any of that stuff.” And I think the more sacred you can make that disconnection, the less time you need to really get to the good stuff, right?

But a lot of people will be like, “Oh, I’ll take, like, one consulting gig a week. It’s like two hours. That’ll allow me to take more time.” Then you’re prepping for it.

Brad Johnson: Or you’re toggling and it’s just…

DJ DiDonna: You can’t travel. Do I have Wi-Fi? Like, all that kind of stuff. And so, I recommend just, like, disconnect for as long as possible. And then that last piece…

Brad Johnson: And so, like, just to control the variables of the game so you can win it. Probably like delete email off your phone. Delete any apps that are like Slack or something like that. Or just throw your phone away and just take a personal bat number only.

DJ DiDonna: Yeah, get like a burner, like Mint Mobile phone. Sponsored by Mint Mobile.

Brad Johnson: Go back to a flip phone. Motorola Razr.

DJ DiDonna: Yeah, it’s like Google Maps, basic messaging. So, again, we all know how distracting it is. We all know how I could be on a pilgrimage in Japan, and read the news with like a flick of the thumb, which just ruins your day

Brad Johnson: Okay. So, duration, disconnect, and did you say experiences? What was the third one?

DJ DiDonna: Yeah, experiment, right? It’s like what kind of hypothesis are you testing? Is it around being more outdoors? Is it around doing more kind of tactile art, creative things? Is it around writing a book, being the primary caretaker? So, just having some stuff that you’re kind of like, “What would this be like? What would this life be like if I was living it for real?” Because on a sabbatical, you’re kind of being, whereas on a vacation, you’re doing. Like, I got this and this and this, and if the flight gets canceled, the whole thing is ruined. Where a sabbatical, you’re like, “I’m going to be into this identity for a couple of weeks, see how it feels, and then move on to the next thing.”

Brad Johnson: So, an interesting alignment with your experiences. Did Airbnb come into any of your research at all? Because there was a really cool finding they had.

DJ DiDonna: No, tell me.

Brad Johnson: So, there was an early blog post by the founder, and he talked about what creates an 11-star experience for the people that stay at their homes. And one of the themes they found is if people get a little bit uncomfortable, if they do something new they haven’t done before, it’s a more memorable trip, and they rate it higher. So, I’ve always talked about bungee jumping. I’ve never gone bungee jumping. I go stay at this Airbnb. I actually bungee jump while I’m there. Level of experience just went up. And so, back to your experiences, kind of combining that with curiosity to pull on that thread, you did something uncomfortable. Like, that many miles in six weeks is wild.

Like you said, you’re not sure if you’d do it again, but it sure took the experience up a notch or two. You stretched yourself. Do you feel like just if you’re your own psychologist, like that going back, you’re like took it up a couple of notches? Or like playing with your own psychology, what’d that do if you delete that and didn’t do it?

DJ DiDonna: Yeah. I think I talk about, so the act of stepping away, I mean, a lot of people have to quit their jobs to do this because the company doesn’t offer it, and they just get to the point where the value that they think they’ll get from it is better, is more than the comfort of staying. So, you’re already doing something uncomfortable by living out this kind of countercultural life, right, taking extended leave. And then when you come back from that, and you realize that everything’s okay and you’re better off, that builds confidence because you’re like, “I did something difficult. I did something counter-cultural. I made the decision. It was intrinsically motivated, and I survived and I thrived.”

And so, from a macro experience, you’re doing something that builds confidence. And then the micro experience inside the sabbatical, you’re often pushing yourself to take on an identity that you’re a financial advisor, now you’re like playing at an open mic in a bar. Right?

Brad Johnson: Right.

DJ DiDonna: So, that’s like a different experience that gives you confidence that you can do all sorts of other things. There’s the physical stretch. And so, you think about like building a muscle, you have to break the cells down in order to rebuild. I mean, you know more about building muscle than I do, which anyone watching the video podcast will see.

Brad Johnson: Trying to stave off old age, my man. That’s all it is.

DJ DiDonna: So, you got to experiment and break down in order to build. And so, in so doing during sabbatical, trying new things on for size, you’re like, “I’ve got more ideas, new ideas. I’ve got the confidence to go out and attack them.” And that’s where that experimentation says, “You know, I actually want to go experiment with running my own shop as opposed to working for someone else, or coming back and working in a very different way that might have felt like I was not as career oriented before, but now I’m like, “Man, I want to spend more time with my kids and put work in like a bucket, so that I can be more present with my family.” So, you hit on an important piece there.

Brad Johnson: All right. I know we’re getting towards the end. I want to tie it back to business here at the end because pretty much most of the audience is probably running a business or kind of running their own book of business. If I was to play out this, “Okay, this sabbatical thing sounds cool,” and then kind of that next level down, “What if we built a model that our team could do that?” one of my fears would be, well, what happens if somebody finds themself on their sabbatical and doesn’t come back? It’s like I created the program that was kind of the exit door to the business. Do you have anything in your research that shows companies that have implemented this, like, how many people stay, how many people go? What’s that look like?

DJ DiDonna: Yeah. It’s this concept of creating a golden parachute, right? And you see in a lot of businesses, they’ve built in these inflection points. In most tech companies, you have, like, four-year vesting, right? And so, like, you vest your options over four years, and then what happens when people get to that point is that most of them leave, right? And so, there’s always inflection points, I think, that companies build into their business where it makes sense for folks to leave. So, it’s seemingly a bad idea to do that. But what I would say is Warren Buffett talks about how time is the enemy of the mediocre company, but the friend of the good company.

Like, on a short-term basis, even if someone leaves or if someone steps away, that’s not great, right? We’re all measuring on, like, short-term quarterly performance. But on a medium-term basis, like, if someone who as soon as you let them off the leash or gave them a little more rope, they left the company, probably weren’t doing their best job, right? They probably weren’t doing their best work. Bring someone in that wants to be here. Or C, like, if you give someone that chance to take a step away and invest more in their personal life, maybe they come back more loyal, and they can see, like, the light at the end of the tunnel every seven or ten years.

And so, they’re loyal to you for letting you do that. They have a light at the end of the tunnel they can work towards. It feels more sustainable, as opposed to getting to the place where you would build up pressure and then leave. And so, I think you have to compare apples to apples, which is, people will leave anyway. People will leave regardless. Some people might leave resentful of you, burnt out, whatever. It’s better to prepare and plan the organization for their departure, which is what you’re getting with the sabbatical. You know in advance, you’re kind of like identifying what all things they can do. You’re distributing their tasks to other people, versus having someone burn out and leave. So, that’s the comparison.

Like interestingly, in the research, and we don’t have enough data points to kind of say this for certain, but over 80% of people that get a sabbatical policy, return to the company, right? And 100% of the people who take a sabbatical and quit their jobs are leaving the company.

Brad Johnson: Yeah.

DJ DiDonna: And so, it’s like I think the battle is, can you keep people engaged? Can you keep people there? Can you keep your best performers? Versus can you pretend like no one’s ever going to leave, by not offering something like this?

Brad Johnson: Yeah. And as I think about it, so let 80% stay. Okay. They’re coming back recharged, fun stories, especially if there’s a program in place. It’s like replanting the seed for those that are maybe a few years out from it. So, now they’re probably staying because they’re looking forward to when they get to do it themselves. But the 20% that left, my gut tells me the first thought of leaving didn’t happen on the sabbatical.

DJ DiDonna: Totally.

Brad Johnson: It was already happening, and that was just kind of the final piece of it. But I look on the backside of it. Okay. So, somebody leaves the company, and your last moment in that company was I did a four-month sabbatical, I did a six-month sabbatical. They’re probably still going to say some pretty cool things about that company.

DJ DiDonna: Totally. Yeah.

Brad Johnson: You know? “Hey, it wasn’t a fit for me forever, but man, it was a good run, and this is how my last four months were spent.”

DJ DiDonna: Yeah. And again, that 80/20, there are so many variances and types of companies and things like that, so I wouldn’t use that as, like, a hard and fast rule. But let’s take it as an example. That’s not 20% of your company is turning over every year. That’s, like, if you offer it every five years, it’s like 4% turnover. I don’t think many companies are getting 4% or fewer turnover. In Silicon Valley, it’s like 20%, 40%. Like, keeping someone for four, five, ten years is a huge win, right?

Brad Johnson: On just the frameworks you’ve seen, and I know there’s a lot out there, I’m sure. So, the finance company that was, it sounds like 10 years to earn your four-month or six-month, which is, I mean, that’s like half a year off, so that makes a lot of sense. But what is the cadence? Do you see, like, is it the first five years typically, some form opens up, 10 years? What’s kind of the frameworks you see?

DJ DiDonna: I think five years is a good one because it gets you past that four-year kind of, like, vesting cliff, right? I mean, it takes you a year plus to get even up to speed, and so, how long can you have people working at full capacity before they want a break? And so, I think especially for the shorter sabbaticals, like two months, six weeks kind of thing, I think five years is great, right? You have something to look forward to. You have enough time to kind of, like, build up and show your value, understand what kind of job you’re doing. But I think probably, like, seven, ten years for the longer ones, where you’re really, like, rewarding kind of long, long tenure.

Brad Johnson: Well, a lot of companies, I don’t have our benefits package right in front of me, but I feel like by the time you hit five years, most people have probably had the ability to, like, get up to three or four weeks of vacation, somewhere in that. It’s probably middle ground. So, now you hit five years, you just say five year you get a double, where it goes from four weeks to eight weeks or three weeks to six weeks.

DJ DiDonna: One time. Yeah.

Brad Johnson: But here’s the caveat, you have to take it all at once.

DJ DiDonna: Yeah.

Brad Johnson: And you’ve got to build your division in a way that allows for that, so you can actually, going all the way back to the beginning, like, it’s actually killing two birds with one stone. You’re building a better business, and kind of putting these little mile markers along the way for people to look forward to and work towards. So, that’s not that big of a stretch, really, when you break it down that way.

DJ DiDonna: Yeah, it’s a cool challenge, right? You’re taking a summer off with your kids or with your family or by yourself in five years. Get to a place where you can handle that, and the business can handle that.

Brad Johnson: There’s another company, I forget which one, that there’s two set times a year, they force their entire team to work remote. And it’s like, it goes something with their business cycle, so it’s like two weeks, two weeks.

DJ DiDonna: Well, I think more and more, the time between Christmas and New Year’s has basically become like a week-long holiday for a lot of companies, which is great. I know, I was just at LinkedIn headquarters. They shut down the week of July 4th every year. And so, I think more and more people are like we saw during the pandemic, we see with remote work, like we can take our foot off the gas a little bit, and get more out of folks overall, burn fewer people out, and just realize that there are many different ways to work that can be successful. And this is asking people to experiment with something else, which is just what’s the treasure that lies on the other side of preparing the organization, preparing yourself, giving your family a gift that’ll last a lifetime. In the scheme of things, it’s a rounding error on the amount of time you work and the amount of money you make.

Brad Johnson: Well, and some other really cool entrepreneurial stories that I’ve seen, like Steve Jobs famously took a long sabbatical to India or roamed around somewhere over there. And that was great.

DJ DiDonna: Yeah. Studying calligraphy.

Brad Johnson: Yeah, it kind of tied some ideas together, and when he got back, he’s like, “Let’s do this.”

DJ DiDonna: Totally. And that was a forced sabbatical, right? He got fired by his own company.

Brad Johnson: Yeah. Round two as a CEO was better for him.

DJ DiDonna: Yeah.

Brad Johnson: Well, my man, this has been an awesome conversation. So, I mean, number one, you’ve grown up in finance, so you’ve experienced some of the burnout that can happen. But I love how you’ve created a framework that’s really cool, so excited to dive into the book when it officially drops. We’ll give some copies away here to the audience. And final question on my side, which looks like my light just went off here, but Do Business, Do Life, that is the concept. It’s build a business that blesses your life, that doesn’t become your life, that kind of integrates, which is very aligned with our whole conversation today. So, I would love to hear DJ’s definition, like, if you were to define Do Business, Do Life for you, what would you say?

DJ DiDonna: Yeah. I mean, I think your sign illustrates it, which is just like life is much bigger, right? Life is bigger. It’s in all caps than business.

Brad Johnson: We’re turning it back on for you.

DJ DiDonna: There we go. And so, I think that’s the right look. It’s the foundation. Like business supports life, not the other way around. I think one of the misconceptions is that by taking a sabbatical, you don’t value work. You don’t want to work. You’ll never come back to work. I’m talking about spreading like a very concentrated chunk of life throughout like a really hardworking life, on the business front. And I think the proof is in the pudding, in our research, in the book, so encourage people to check it out. Encourage people to ask other folks in their life who have taken an extended leave to get kind of permission, and just really see, like, what are the other ways that I could be living life, and how can business enable that as opposed to kind of control and take over?

Brad Johnson: Well said. And you basically wrote a book on it, so I’m sure there’s a lot more in the book too. So, DJ, I’ve really enjoyed the conversation. Picked up a lot personally. Great timing. Getting ready to go on vacation here in a couple of days with the full fam. So, I’ll make sure I put some of the practices, although shorter duration, into place. I need to find something to get a little uncomfortable with while I’m there, so.

DJ DiDonna: Awesome.

Brad Johnson: All right, my man. Until next time. Appreciate it.

DJ DiDonna: Great chatting.