What about an unlimited vacation policy?

A self-managed vacation policy sounds like a utopian dream. But its value for employees and organisations really depends on how it’s implemented and embraced by company culture.

By now, we hope the latest Uncensored article finds you by the seaside, relaxing next to the numbing sound of the waves, or perhaps at a mountainous hill filling your lungs with fresh countryside air. Maybe you are still planning, in excitement and last-minute panic, your next spontaneous getaway. 

Whichever the case may be, it is quite likely that a thought is currently slipping to your mind: wouldn’t it be wonderful to experience this kind of freedom whenever you’d like?

The idea of an unlimited or self-managed vacation policy may sound to some like a utopian dream. If it also sounds oddly familiar, it is because more and more companies are making it a reality, incorporating it as a part of their benefits offering. 

In an era where employee well-being is prioritised by many employment value propositions, unlimited vacation policies have emerged as a bold, modern perk that symbolises autonomy and trust, as well as a popular perk companies may need to consider in order to remain attractive to top talent.

But before you start packing your bags for that month-long retreat, it’s worth taking a closer look at what this policy means, and what else needs to be in place to fully make the best of it for employees and companies alike.

While the idea of endless holidays is appealing, it comes with its own set of challenges and complexities. And as alluring as the promise may seem, the value of unlimited vacation largely depends on how it’s implemented and, more importantly, how it’s embraced by the company culture.

It is actually a policy we include as part of our operating system at REBORRN. We have an unlimited, self-managed vacation policy precisely because we don't like to tell our people when or why to take their days off: as long as we deliver and have the expected impact, we can have as many off days as we may need. But we also believe that unlimited vacation isn’t a one-size-fits-all solution, and its success hinges on several critical factors beyond merely having it there.

So to accompany your summer, we gathered some perspectives by some of our own employees, as well as several testimonials from others who work for companies with unlimited vacation policies. Let’s take a look at how the policy can actually be all sunshine and no rain, providing benefits and avoiding potential traps and pitfalls.

🙏The Promise of Flexibility and Trust

As many of our testimonials confirmed, when done effectively an unlimited vacation policy is an offering of unparalleled flexibility for many employees. Anastasia Terzidou, Content Strategist and Operator at BORRN, actually describes it as a “real game-changer” for her. 

“It is fundamentally about trust”, she tells us. “We have the freedom to manage our own schedules, which means I can plan longer trips or take days off when unexpected things come up, without the worry of counting days. This flexibility is a real standout”.

Another employee, who has worked for multiple companies with unlimited vacation policies, also believes that when done right the policy offers benefits that extend beyond taking lengthy vacations to recharge your batteries. “It also allows for flexibility with your day-to-day life planning” she tells REBORRN.

“If you have personal appointments with a bank or a pile-up of errands, it's easy to take a day off without meaning you'll get fewer days to actually rest. Or, if it's been a particularly stretched month, you can give yourself a long weekend to allow yourself to perform better next week - instead of simply showing up as a zombie for work”.

🤝The importance of teams

As is the case with co-travellers, colleagues can really make or break the experience when it comes to unlimited vacation policy. 

Several testimonials we gathered identified the benefits of the policy for teamwork. But employees also believe that it only works, and doesn’t lead to chaos or resentment, when fellow teammates are trusted to manage their workload responsibly, and when teams form a robust safety net should a personal needs arise.

“From my observation, the success of such a policy heavily depends on the team dynamics. Our team members are chosen for their strong sense of ownership and responsibility, which minimises any potential negative impact on our workflow. There's a mutual trust that underpins this policy, allowing it to function effectively”, highlights Anastasia.

Another employee mentioned the importance of transparency and communication within and between teams of an organisation, as “without clear guidelines, it may lead to inconsistencies in employee availability, making it harder to maintain a steady workflow in projects”. A UK employee described to us a “summer of hell”, when “a number of colleagues simultaneously took time off, simply dumbing an unfeasible level of work responsibility to those who stayed behind”.

Ana Tsitsa, REBORRN’s Communications Manager, strongly believes that the potential pitfalls with unlimited vacation policy begin with the hiring process. “When a team is composed of top players who share the same values and purpose, which means sharing the same responsibility towards each other and the group, it's easier to maintain a balance between "official days off" and "too many days off."”, she says.

One of the potential pitfalls she recognises has to do with uneven distribution of time off within teams. Without clear guidelines, some employees may overwork out of fear of stigma, while others might take more days off, leading to scheduling conflicts and resentment. This unevenness can disrupt team dynamics and create an environment of discomfort and mistrust.

Then there is also the potential challenge she identifies, one of continuity. “An "unlimited days off" policy requires a proactive approach to project and task management to ensure continuity”, she notes. “This level of organisation demands excellent team and project management skills, which is not always the case, especially in diverse teams”

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🏖️Unlimited promises, less time off?

“There is a saying among many candidates: "if you hear that a company offers unlimited PTO, run as far as you can!"”, told us another employee, who has worked for multiple companies that offer unlimited vacation policies. “This is usually because such a benefit is frequently offered in startup environments which are by default very demanding and the promise for unlimited PTO is just not realistic in practice”, he added, clarifying the context.

But the start-up environment may not be the only case where an unlimited vacation policy can, paradoxically, lead to employees taking the same, if not less time off compared to a less flexible policy.

“I work for a big, US-based media company, and I can confidently tell you that literally nobody ever takes more than 20 days off, out of fear or shame, despite the policy" told us a US mid-level employee who is based in New York City. “It makes no difference”.

In both cases, the challenge lies in the gap between the promise and the culture that organisations actually offer. Despite the hypothetical possibility of unlimited vacation, employees have to first ask their manager for time off as something that is their initiative, and not something they are legally entitled to. “In many cases”, an employee with experience in Greece and the UK told us, “that means you're too afraid to actually take it”.

In fact, the data comparing time off in companies with limited and unlimited PTO tell a rather conflicting story:

• Namely’s 2022 unlimited PTO survey found that workers with unlimited PTO took an average of 12.09 days off, while limited PTO workers took 11.36 days off. It also found that workers are taking less time off in general than they used to, regardless of the type of policy.

• In contrast, a Joblist survey found that those with unlimited PTO took just 10 days off on average, whereas workers in an accrued PTO bank system took 11 days off. Additionally, 43.7% of respondents don’t feel like they took enough vacation time.

• Simlilarly, Sorbet’s 2022 PTO report found that workers with access to unlimited PTO still take about 30% fewer days off, on average, than those with more limited policies.

🤳But do you actually switch off?

There is also another way in which unlimited vacation policies can end up being less shiny. As some testimonials we gathered pointed out, sometimes this means that you may end up with days off that, well, aren’t really that off.

“Especially in periods where projects are really active, taking time off might make you feel the mental load of “abandoning ship””, a consultant told us, arguing that this might make it difficult to fully disconnect during some of your unlimited vacation time.

This problem, she believes, is also often compounded by the pressure to catch up on work after returning, which can diminish the intended benefits of rest. “But this is something that is definitely made better by having colleagues who really hold down the fort”, she is quick to add.

Another employee noticed a different pattern, one that affects expectations from people when they are on their time off. “I have noticed that sometimes people feel less guilty reaching out to you while on annual leave in organisations where you get unlimited vacations. In a way they are sometimes sort of considered less 'holy' than the fixed 20 something days you'd normally get” she points out, though she adds that this may stem from logistics perspective given the work that needs to be done.

“There's simply a realistic limit to how much time you can take COMPLETELY off”, she adds.

💼Pack your bags, managers!

As is the case with a number of benefits, for an unlimited vacation policy to actually work it needs to be effectively championed by a company’s leadership. Yes, sometimes, managers themselves need to admit that they need a little break, taking time off and setting the example for the policy for others to follow.

“There are many times where the direct manager influences the desire of people to make use of the benefit or not”, an employee combining experience in both the consulting and the tech industry told us. “First off, if they are not using this themselves, the team might be afraid to do so. Secondly, a manager can very easily cultivate the feeling of guilt to people that might consider using this”.

Anastasia Terzidou admits that, like many others, she was quite hesitant to use the policy because it sounded almost too good to be true. “Initially, this tentativeness meant I actually took fewer days off. However, over time, as I grew more accustomed to the policy, my confidence increased, and I began to take more advantage of the flexibility it offered”, she adds, noting that it is something she largely credits leadership for.

“Our managers don't just talk about the policy—they actively encourage us to take time off, especially after intense work periods. It’s not just a policy on paper; it’s a practice that we live, ensuring we really benefit from it”.

🏝️A Perk with Potential, Not a Standalone Solution

Take it from experience: unlimited PTO can indeed be a powerful tool for enhancing employee satisfaction and fostering a culture of trust and autonomy. It can lead to more rested and productive employees, and strike a good sense of work-life balance. 

It can be as dreamy as it sounds, but as the testimonials illustrate, it is not by itself a silver bullet.

Companies who offer it must actively create a context in which such a policy can thrive—this includes proper resource planning, cross-team communication, educating managers to lead by example, and fostering a supportive organisational culture where taking time off is genuinely encouraged and guilt-free. .

Without these critical elements, the promise of unlimited vacation can easily fall flat, leading to underutilisation and even unintended stress for employees. And instead of offering a benefit with value for your employees and organisations alike, you may just be building castles in the sand. 

“I had a brief stint at a company that advertised unlimited holidays but actually had an awfully toxic culture, where nobody had a concept of working hours vs personal life”, concludes one of the employees that shared her thoughts with us. “How do you shoot off to an island when everyone is slaving away and pointing fingers at each other? You simply don't. So an unlimited vacation policy is by no means a standalone solution”.

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Thank you for reading this week’s Uncensored article, the first one of our Unorthodox Benefits series. We will be back after a brief break (because everybody needs their time off) with an article exploring shiny perks like pool tables - and whether they actually matter.