24 Nov 2025 · 5 min
Filipino online freelancers often skip vacations even with unlimited PTO because they want to please employers, save leave for emergencies, or were discouraged by past jobs. John Jonas explains how managers can help: explicitly tell people to take time off, promise coverage is handled, and let them check in briefly if it eases their mind.
Welcome to the Secret Sauce of Outsourcing podcast that's dedicated to making you better at outsourcing. This is episode 168, why your OFS doesn't want to take a Vacation. So vacation is supposed to be a really happy thing. It's supposed to be relaxing and soothing, and that's often not the case in the Philippines, and especially not when working for you. So this is really interesting and I've thought about this over the years and I've just recently come to a better understanding about it. So we're pretty generous with paid time off at onlinejobs ph we tell people you can have as much paid time off as you want. We just want to know about it ahead of time if we can, or as soon as we can, know if you're sick or something like that. We don't track paid time off. We just let them have whatever they want. And yet I still feel like people are really hesitant to take a vacation. We want them to take a vacation. We want them to have a break from work. We want them to know that we appreciate them and we appreciate their hard work. I want them to be healthy. Giving as much time off as we can is our way of doing that. And yet still it's a struggle. And I thought this was kind of unique to us. And then I get this email from Andrea, so here's what it says. When I hired my OFS in October 2020, I told her she got 10 US holidays and she was welcome to exchange them for holidays she preferred. She was also granted two weeks of paid vacation upon completing six months. She has taken hardly any vacation time. So I addressed it, asking if it was cultural or something else. She let me know it was cultural and that previous employers discouraged vacation time. I assured her we wanted her to take a vacation, to come back refreshed and renewed and ready to work again. She was happy to hear that. So there's a couple things going on here that I've talked to my team about and things that I've realized over the years. So one, Filipinos are very eager to please. They want to make you happy. And if they find a job that they really like, well, not taking vacation is one way to make you happy. And that's how they see it. Another consideration here is that often Filipinos are hesitant to take their time because when they need time off, it's often long time that they need. So, like a death in the family or a serious illness will require them to be off for a week or two weeks or even longer Sometimes. And so they're hesitant to take their two weeks of vacation and use it on vacation when they know they're going to need to take care of their mother in law with that time or they think they might need to take care of their mother in law with that time at some point. So they'll want to save the time and bank it hoping that they can use it in the future even though they're still going to be hesitant to use it. So then in terms of discouraging, she says in her email that her OFS said her previous employer discouraged it. Man, I mean, I can understand why you might discourage someone taking paid time off, but how damaging is that to that person and their maybe to their working relationship with you or to their ability to be healthy. Right. So I would highly recommend not discouraging them from taking their PTO or even encouraging them to take it. Now let me tell you a story that happened to me this week. In fact, I mean this was yesterday, right as I was getting ready to record this. So we have someone in the Philippines whose wife recently had a baby. He took two weeks off for that because it was a struggle for her. That was a few months ago. Then a couple days ago he asked if it was okay if he could go and visit his family. He hasn't seen them in a while and he said this is going to be two weeks but I'll really, really try hard to work. And we were both me and my partner Dan responded to him and said, hey look you, you have unlimited paid time off. You're welcome to just take this time off. We don't care. Now he's actually a really important programmer for us. He's in the middle of a really important project. We're trying to improve the search on onlinejobs.ph because our search sucks and our current system won't allow us to improve it. So we're changing the system over and he's in charge of this and it's taking a long time as is, but he was still really concerned about taking the time off when he had taken time off before, even knowing he has unlimited paid time off. And so we had to encourage it. Hey look, take the time. Yes, we know you took a couple weeks before. That has nothing to do with now. We want you to go take this time off if you can. This is what we said. If you can check your email still regularly and if there's something you can do to push this project forward, like you're working with a couple other people on it. If there's something they need from you. If you can take care of that while you're gone, that'd be awesome. But otherwise you're fine to take the paid time off. So just a number of things that you can do to help your team with their paid time off. Recognize that people get tired of work. Your OFs probably get tired of it too, and they need time off. They need a vacation. They might need some encouragement from you.
