DJ DiDonna was running a successful fintech company that he co-founded after business school. Over the space of seven years, he grew the business across four continents while living in Africa, Asia and Latin America. 

But when this dream career path led to burnout, DJ decided to take some time out. On a four-month sabbatical, he travelled through New Zealand, walked a Buddhist pilgrimage on a Japanese island, and spent time connecting with his parents.

After returning from the journey, DJ made the decision to move on from his business, which was acquired within a year. Embarking on a new pathway, he harnessed his experience to establish The Sabbatical Project, working with a research professor to build a better understanding of sabbaticals and the benefits they can bring.

In this interview, DJ recalls the events that led to his own decision to take a sabbatical, his experiences during the time off, and how it has impacted his life since. 

What inspired your decision to take a sabbatical?

I think I’d always had this underlying urge to take a large block of time off and do things that you just can’t do in the confines of a regular job and career. You know, if you want to walk the Camino de Santiago or do a big mountaineering trip, you just can’t do that. Especially within the American vacation confines, if you take two weeks off in a row, people kinda look at you a little strangely.

About six years in, my co-founder and I looked at each other, and we were just burnt out. No one had prepared me for the reality of being burnt out from my dream job. I created a company, created a culture, it was doing good in the world. I was getting to see and live and work in exotic places and learn a lot.

You hear about burnout like “oh, I was working in this accountancy firm and I hated my life”. But that was not me.

After a while, we just said we need to take some time off and get some separation. Then we spent a little over a year building the business up to the point where it could afford for me to do that, and I took off.

As a business owner, how did you prepare for such a long absence from your role?

It’s not like we were a Fortune 50 company, but I think the lessons apply to all sizes of company. The biggest mistake that a business leader can make is assuming they’re irreplaceable. And if you build a business to function in a way that you are irreplaceable, you’ve done a bad job.

And so, frankly, it was pretty easy. We just established it as a priority, and we hired people to fill in the gaps. The idea is that when you come back, you either figure out that you made a good job of that, or you actually were instrumental in some of the areas in which you tried to fill holes, and then you can address that.

More often than not, especially from the conversations I’ve had with business leaders, they’ve realised that other people can do their work. Then it frees them up to do other work that only they can do, or it gives them perspective about what their role should be in the future of the organisation.

DJ DiDonna
Dj DiDonna during his days as a fintech business owner

Did you meet any kind of obstacles in your personal and social life? If so, how did you navigate them?

As I’ve heard from a lot of people’s sabbatical stories, I was at an intersection of a lot of aspects of my life. The end of a relationship, burnout at work. And so it’s hard to tell which came first, the chicken or the egg. Did I hasten those endings, or were they the catalyst for the sabbatical itself?

From a logistical standpoint, I had a mortgage, and so you find renters. And you think about your finances a little bit differently and say, alright, what are the costs that I should continue to bear, and what are ways I can even make money when I’m gone, by renting out my place and things like that.

You just align what life would be like without work, without a paycheck, without being in the same geographic location, get it on a list and solve the problems.

“I just needed a catalyst to get myself out of there. The business will never let you go if you don’t make yourself leave.”

You were away for four months on sabbatical. What did you do with the time off?

There’s a clinical definition around the inability to get stuff done and low energy – that’s where I was. And to not even have the energy to plan a once-in-a-lifetime trip was pretty depressing, and it becomes a bit of a vicious cycle. I just needed a catalyst to get myself out of there. The business will never let you go if you don’t make yourself leave.

I had a couple of friends who had just gotten married. I officiated their wedding, and they were doing a second ceremony in New Zealand. So I used that as the catalyst. I hadn’t really planned on going to New Zealand, I just kicked it off there.

There were a couple of things I wanted to do. One of my parents was in a health crisis, so I wanted to spend some time with them. And two, I wanted to walk this pilgrimage in Japan. I’d done a part of the Camino de Santiago in Spain, and I thought something that slowed me down and nourished my spiritual side was really what I hadn’t been doing in a while.

In New Zealand I did some mountaineering, travelling around, bought a motorcycle, did a meditation retreat. And then I went to Japan, where I spent six weeks walking on this Buddhist pilgrimage on the island of Shikoku.

Do you have any particular standout memories from your sabbatical?

So many. I wrote and performed my first song. I helped my Dad remodel a house. I helped to get my Mom in and out of hospital care. Finishing that walk in Japan was pretty tremendous. There’s just so many memories.

One of the things that stands out is that on the pilgrimage, they have this notion of ‘osettai’, which is basically people giving you gifts for no reason. So you’re walking around, you’re wearing a big straw hat, you’re dressed in these sashes, you carry this stick with a bell on it, with all your possessions on your back, and people would just come up and give you free stuff, because they could see you’re a pilgrim. Whether it’s an orange in the morning, or money in a coffee vending machine, or picking you up when it’s raining and hosting you at their house. So you have this barrage of daily trials and tribulations, just like everybody does in normal life, but you also have this steady stream of strangers giving you small acts of kindness. That combined as a whole is pretty staggering.

Dj on a pilgrimage in Japan
DJ took part in a Buddhist pilgrimage on the Japanese island of Shikoku during his sabbatical

What did you learn from your time away from work that you would never have learned while you were in your regular working routine?

Partly the oversize role that work had taken in my identity. I think it was particularly difficult for me, because I started a company and it was doing good. That’s a hard existence to leave, because you feel an obligation to keep doing it.

The second thing was how you generally escape yourself. I remember the way I went about tackling the pilgrimage was very fast. I was passing everybody, I was by myself, it was kind of like a physical feat I was overcoming. About three quarters of the way through, I realised that I had no reason to hustle through it. I had no deadlines on the other side, and I was causing real physical damage to my body by doing so.

So I promised to take it slower and cap the number of kilometres I walked per day. That lasted for another week. I realised at the end that I couldn’t really change my wiring, but what I did instead was I got to the finish in the amount of time that I wanted to, but I stuck around there for a couple days and gave care packages to people starting out on their pilgrimage.

So I didn’t slow down, but I did take the thing that I do and approached it in a more gratitude-focused, caring way, which I think is the best I can do with my constitution.

What were the biggest challenges in resuming your working life when you returned from your journey?

I think it opened up a bit of a Pandora’s box. Once you see inside, back to who you are and your core self, it can be tough to get as excited about the things that you were motivated by before.

I think what was going on in my case is that I was changing and I was evolving, but I wasn’t allowing that to show in my work. It was clear that I needed to move on, start the next thing, and empower people inside the organisation to take over.

So I used it as a reflection to come back and have the courage to move on.

“I’m still pursuing things I think are important, but I think I’m more comfortable doing something that doesn’t have prestige wrapped around it.”

Do you think your sabbatical experiences had a long-term impact on the way you approach work?

Yeah, of course. I’d always heeded my own call, as far as what I wanted to do. I think it just shored up that decision being a good one.

I think probably the biggest change is the understanding that you can take time periodically to reassess what you thought you should be doing and what you are doing, and realign it to reality. To reorient yourself with your map.

I’m still pursuing things I think are important, but I think I’m more comfortable doing something that doesn’t have prestige wrapped around it. I kinda lost that desire and need. And, taking that osettai lesson, I hope that I’m doing things that are helpful to other people, as opposed to just for myself.

Have you made any big lifestyle changes as a result of your sabbatical experience?

It’s tough to disentangle the nature of the work that I was doing before with what I’m doing now. It’s also tough to disentangle the changes related to age and just growing up. For example, I don’t have the energy to do the Herculean tasks that I was doing with the business before. And I’m not sure if I couldn’t do that now just because I’m older, or because I made that conscious decision.

There’s a saying in vipassana meditation, and Dan Harris has famously created a company and written a book about it, but I think I changed 10%. I meditate more, I’m calmer, just aligning the ship a little bit closer to the direction that I wanted to go. And those little changes add up over time.

What has been your career direction since returning from your sabbatical?

Totally different. After I left, we got acquired within a year, so that closed that chapter and gave me a little bit of a narrative about being a ‘successful’ business person.

The thing I like about how things turned out is that I actually made the decision to leave the company before I knew it would be ‘successful’. I made that decision to leave based on what I learned and what I knew about myself.

As far as the kind of work I’m doing now, it could not be more different. I teamed up with a professor and did qualitative research. I learned how to do that in order to make the case for sabbaticals, and really understand that my experience was more universally applicable.

DJ DiDonna TEDx talk
DJ giving a TEDx talk about sabbaticals

Are you happy with where you’ve been going?

I believe strongly in what I’m doing. I believe strongly in the power of this amount of time off, and that the world would be a better place if everyone were enabled to do so.

It’s very different. I don’t think that what I’m doing right now is best aligned to my personality. I really miss working with people, and starting and growing organisations. But I think this is a really important phase in getting all the information together and getting it out in a way that can help make a difference.

I guess I’m more comfortable with things being in phases versus being a “this is my dream job, I will do it until I die” kind of approach.

What advice would you give to someone who is considering taking a sabbatical, but might have reservations about it?

There are different types of reservations. In my experience it’s been financial reservation, it’s perception optics, and then it’s responsibilities. And those are serious issues for people. They’re not imagined for a lot of folks.

I guess what I would say is, think back to what stories you want to tell about your life to your grandkids. Think about what lessons you want to pass along. And think about whether those stories are actually possible in your routine life.

I suspect most people have a bucket list that you can’t just accomplish on weekend trips and things like that. And I think the idea is powerful enough that once you actually think of those things that you want to accomplish, it becomes self-evident.

Did you enjoy DJ’s story? You can find more inspiration in our series of career break interviews. To begin planning your own sabbatical, our ultimate guide provides the foundations.

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DJ DiDonna was leading a successful fintech company when he took a four-month sabbatical that led to a new research project. #sabbatical #sabbaticals #timeout #timeoff #careerbreak

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