The Workation Manifesto // How Companies Can Embrace Digital Nomadism Through Innovative Vacation Policies

Why current vacation policy solutions aren't working, and how companies can adopt workations to attract, retain and reward employees.

Published on
June 27, 2018

Employment trend reports and articles about the future of work, suggest that the modern workforce is undergoing a massive transformation. The way people work, the work they do, and how they get work done – everything is in a state of flux as a new generation of technologically savvy employees demand greater freedom and fulfillment from their careers.


The Problem

Throughout this transformation, one area has not been changed: vacation policy. Most companies in the United States offer an outdated vacation policy that isn’t in touch with the values of most workers. Most employers still over either 10 or 15 days off per year, and the U.S. is one of the few countries in the world without a minimum number of days off per year. In a 2014 survey by Glassdoor, only 25 percent of employees who receive vacation and/or paid time off reported taking 100 percent of their eligible time off, and 40 percent of employees reported taking 25 percent or less of their eligible time off. Especially among millennial employees, a fixed number of vacation days is viewed as a less valuable benefit, compared to broader  concepts like work-life harmony and the freedom to travel while holding a full-time role. Telecommuting and flexible vacation policies have become a standard negotiation point for high-quality talent, especially in tech-centric areas like San Francisco. Unfortunately, companies who are slow (or fail entirely) to adjust, are  mi unable to build and retain the most talented teams. 

Current Solutions

Some companies, however, recognize this issue and have been proactive in trying to solve the “vacation problem” for employees. These companies adopted one or more of the following solutions: 

The Unlimited Vacation Policy

Ah, the dream. Unlimited vacation policies seem like the perfect solution to many over-worked, under-relaxed employees. Some high-profile companies have decided to try implement the policy with mixed results. A few common examples include Gusto and Netflix. Gusto, formerly ZenPayroll, has headquarters in San Francisco and Denver, with employees working from all over the U.S. Gusto decided to implement what they called a “flexible vacation policy” that employed strict communication guidelines to help manage the fact that employees could suddenly work from anywhere at any time.  

At the end of the day, most companies that offer an unlimited vacation policy – crowdfunding behemoth Kickstarter is an example – realized that unlimited vacation policies actually discouraged employees taking vacation days. Instead of encouraging freedom, this policy resulted in  most employees taking no more days off than under a fixed vacation policy, or even take fewer days off per year. When Kickstarter learned this, they actually axed their unlimited vacation policy and increased the number of days off above the national average. The unlimited vacation policy sounds great on paper. It encourages employees to act as individuals, claim responsibility and ownership of their work, and conveys trust from the employer. However, experience has shown that it doesn’t improve the work-life balance of employees in the long run.  

The Team Retreat

At Outsite, we love team retreats. At Buffer, we love team retreats. We know the value of bringing employees together outside of the office to work, play, or combine the two. The team retreat is another solution many companies have embraced in trying to help their employees enjoy better work-life harmony and travel. We’ve detailed many times how companies have strengthened employee bonds, improved culture, and given back. When KIND Snacks came to stay at the Outsite Santa Cruz House participants quickly discovered how far  the team retreat concept has developed(thankfully)

from the sterile conference centers and ice-breakers of the 1990s to allow employees to connect in more meaningful and powerful ways.  

Team retreats are a valuable part of building your company culture and helping employees create a meaningful connection to their work and one another. However, these retreats (no matter how fun and adventurous) by themselves cannot completely solve modern issues of work-life harmony or having the freedom to travel. Team retreats are most effective when combined with another option such as remote work or “workation” options.  

The Remote Workforce

Thanks to the Internet, a remote workforce is now a reality. Some of the biggest, best companies in the world are successfully managing a remote workforce without hovering over each employee’s shoulder or using screen-monitoring technology to hold them accountable. If there’s one thing we’ve learned in the past decade, it’s that employees are far more productive when you give them the freedom to choose where and when they work. That productivity comes at a cost though. Increased productive time is just that: time. Remote employees often work more, take less time off, and have poorer work-life harmony because they can’t leave their work at the office – they literally live in the office! The before-mentioned Glassdoor survey found that “three in five employees with vacation/paid time off admit working at least some while on vacation. One in four report being contacted by a colleague about a work-related matter while taking time off, and one in five have been contacted by their boss.”  

This isn’t necessarily  bad thing from the employer perspective, of course. In addition to saving on office costs, having productive employees can really help the bottom line. But, it also comes with greater risk of burnout, higher turnover, and smouldering dissatisfaction that you can’t see or address because you’re not working with your employees. (In fact, combining team retreats with remote work is often a great option - because the team gets face-to-face time and it allows employers to address any issues that might go unresolved otherwise.) Remote workforces are a great solution to some business pressures – but again, they don’t solve all of them!  

Another Option: The Workation

Of employees who have worked while on vacation, one in three (33 percent) report doing so because no one else at their company can do the work. Other reasons for working while on vacation include: fear of getting behind (28 percent), desire for a promotion (19 percent), fear of losing job (17 percent), and wanting to outperform colleagues (13 percent), among other reasons. To add to this list of available solutions, we propose companies add X workation days on top of the vacation policy of their choice. 

 The workation concept could be used in conjunction with unlimited vacation policy, team retreats, and/or allowing your employees to go remote in order to create the best balance between productivity and happiness/health for your employees. We suggest that  employers  designate a specific number of “workation” days per year, in addition to any vacation days employees already receive. These days should be clearly defined and communicated, and counted separately for each employee. This can be especially useful for new mothers and fathers, as well as parents with small children or other dependents - and allow your team to access their talent, without forcing them to compromise on their priorities Encouraging both vacation and workation will allow each employee to take full advantage of creating work-life harmony as they see fit, while still encouraging productivity.  

Why It Works

Workations solve the problems of work-life harmony and freedom to travel because they encourage the employee to have both. It’s the equivalent of saying “Hey John, I need you to go lay on the beach in Hawaii for a while – while you’re there, please make sure you meet our monthly quota.” Of course, the company should be understanding of a slight dip in productivity during a workation but this is balanced by the upside of team member happiness. Workations encourage productivity in the same way that remote work does, but in smaller doses. They incite creativity and innovation by changing allowing your employees to choose different scenery that might inspire them. They enhance retention, and can foster team-building when employees come back more rested and enthusiastic for their work.  

Fresh Tilled soil

In advocating for adding a workation policy to your benefits plan, we wanted to provide you with at least one example. We found that Fresh Tilled Soil, a Boston-based UX/UI firm, has used a workation policy to successfully improve productivity and employee happiness. Back in 2012, Fresh Tilled Soil was super progressive in establishing an incentive-based workation policy. They laid out professional goals for each employee, and those that met the goal were allowed to take a workation in Costa Rica. Those that went enjoyed shorter work days, beautiful surroundings, and plenty of inspiration for when they came back to the office. While this was one of the only examples of any workation policy we could find, it shows how each company can A) implement a policy that encourages workations and B) takes advantage of the enhanced productivity, creativity, and retention that workations encourage.  

Bridging the Gap

Even if a workation policy isn’t possible at your company just yet, there are still ways to begin implementing a workation policy over time. If your company offers limited vacation time, it’s time to sit down and crunch numbers. Think earnestly about how much time you think each employee is productive each day, and how that might be improved by offering 1-5 workation days per year. If your company already has team retreats, start transitioning some of these into “team workations,” or schedule an additional retreat each year so that one is “work” and one is “play.” Spaces like Outsite are able to accommodate teams for both workations and retretas. If your company is remote, begin actively encouraging employees to take workation days if possible. Not all members of your team may be mobile, but with planning and clear communication, even the developer most glued to their computer can take advantage of a workation day or two. Some companies have begun doing this already: Gusto – in addition to their unlimited vacation policy – hosts regular team workations, as does educational MOOC platform Udemy. If you’re ready to start planning a team workation to see how it can help your company and potentially become a long-term benefit for your employees, feel free to contact us at Outsite with your questions.

Words: Rodolphe Dutel // Founder -, Head of Business Dev. - Buffer

& Emmanuel Guisset // Founder and CEO - Outsite

Photographs: Outsite

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