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The Allure of Life Sabbaticals

An Interview with Remote Year Founder and CEO, Greg Caplan

— January 20, 2020 — Business
As technology evolves, it becomes adopted in different spheres of social and professional life. In the workplace, the move to digital methods of interaction and communication has necessitated a shift in the way in which people perceive the traditional nine-to-five. With the ever-growing, hyper-connected environment, more and more individuals look for ways to take advantage of the liberties that technology affords them and this demand is disrupting long-standing office structures and methodologies.

Remote Year was born out of this shift. The company seeks to “change your life personally and professionally” by orchestrating a program that will allow individuals to work remotely, while still succeeding professionally. Most recently, the company has collaborated with Simplii Financial that informs their service, with a focus on financial feasibility.

Trent Hunter spoke to Greg Caplan – founder and CEO of Remote Year, about the company’s conception and the ways in which it helps participants reach life-changing experiences, without compromising career growth.

Can you speak a little bit more about how the traditional workspace has changed in recent years?

What we are seeing is a radical evolution of the workplace and it is all powered by technological growth. We are becoming increasingly more productive as we move to things like cloud-based communication and as our interactions become digital. What this shift is doing is it is allowing people to really break free of the traditional office environment and get great work done from anywhere. As we think about these technologies, they do not only permeate the office, but also people's personal lives. These innovations enable individuals to really unshackle themselves from traditional things that require physical effort and time -- digital banking replaces going to the bank on foot, for example.

What's really special is that people are no longer encumbered by things that keep them in one place and instead experience a degree of freedom that pushes them to really get out in the world and explore as they reach life-changing experiences. Our goal at Remote Year is to help people take advantage of this new flexibility and inspire them to take the leap to get out of the office; to use technology as a tool that is liberating and allows them to explore beyond the walls.

What do you think the breaking point in employee behavior was that necessitated this change?

According to a recent survey, two-thirds of Canadians are interested in opting in for a life sabbatical and they are really starting to put their foot down. That's crazy! It really has become a mega trend. Acknowledging that this experience is something that you'd like to do, that you'd like to take advantage of the new-found flexibility in the workplace, and realizing in what ways digital technology can help you do this freely, is the process that allows the shift. The growing demand for experiences such as these is what really catalyzes and accelerates this change -- maybe, it is even more rapid than anyone expected.

How did Remote Year come about and what gap does it fill in the industry?

I'll take you back to 2014. I was working in Chicago on a nine-to-five work schedule. You'd come in the same office every day, met by a sea of desks full of people who looked kind of uninspired by what they were doing. I personally felt stuck. I wanted to get out, see the world, do something different. So, I found some consulting work that I could do from anywhere and I was preparing to leave and travel. But what I really wanted to find was also a community. I hosted a dinner one night with a group of my best friends and asked them their opinion on a gig of this kind. I told them that we could work remotely and travel together. These people were from a relatively traditional career background -- think, consultants and investment bankers. They all looked at me as if I was crazy and said that what I was proposing didn't make any sense.

How does Remote Year curate its programs? What are the factors you consider?

The key innovation behind Remote Year as that it helps people be successful while working remotely and living abroad for extended periods of time. The way we curate our offering is really focused on that. We have built our travel experience, we have secured accommodations in the form of apartments that we rent, and we have workspaces in every city we operate in. All of these decisions are made with a focus on helping people stay connected and productive throughout the entire journey.

Then we turn to how we manage community. Everyone's focused on being successful and productive professionally. As a result, we plan all the events and activities to help people grow and advance in their field, while also being conscious of their working hours. We really are building these programs from scratch, emphasizing this new type of travel experience that is a hybrid between a holiday and professional growth. It's about being productive and being inspired.

The program is really for anybody who wants to pursue something professionally -- about 54% of the people in our programs work full time for one company and about 46% are independent professionals who either own their own business or are freelancers.

Any success stories that you could share with us?

On average, 90% of people who opt in for Remote Year say that they are more productive on our programs than they are in the office environment. This supports the idea that when people work remotely, they have an easier time prioritizing and focusing on getting things done. In the office, on the other hand, you can get distracted by your coworkers and not finish the task-at-hand efficiently enough. You feel like you are getting judged on your office etiquette and other factors. When working remotely, the only way you get judged is by your work output and that is what really motivates people to get things done. This is why many participants in the program are successful, constantly growing and changing, getting promoted.

Where do you think the workspace will be in 10 years?

The workplace is evolving very rapidly and the main catalyst for this evolution is technology. It is helping people communicate in an efficient and novel way by causing a fundamental transition from an offline, in-person communication style to a digital one. The migration to the digital sphere enables people to correspond from anywhere, facilitating a seamless operation for any team. I think this will continue to evolve.

Digital connectivity will also make it easier for people to mix and match talent and allow teams to collaborate in unique and interesting ways, which will strive toward increasing output and productivity. We're going to see all kinds of new, exciting innovations along the way and the workspace in 10 years might not be compatible with these very structures, full-time, long-term work relationships we have today.

Could you tell us more about Remote Year's collaboration with Simplii Financial?

Simplii Financial held a study that I mentioned before, the one that revealed that two-thirds of Canadians want to take a life sabbatical. We saw an opportunity here and we entered a collaboration with Simplii to help Canadians understand how to make all of this possible in a way that is financially compatible. And sometimes, this option is even more affordable if you live in a city like Toronto or Vancouver where the renting prices are genuinely high. We hope to grow this passion for adventure and make our service available to Canadians all across the country. The goal of our collaboration is to make that happen. We're super excited to work on this together and change a lot of lives across Canada.

Photo Credits: Remote Year