How to Negotiate for More Vacation Days

Late capitalism is only going to be kind to a handful of people in the end, and none of them was ever going to be you. If you’re fortunate enough to have a full-time job with benefits, you might get stuck thinking salary’s the only thing you can negotiate for. It’s time to fix that by negotiating for more PTO.

“There are a lot of trends that are going on in this area that are kind of shaking up the traditional way of thinking about requesting time off,” said Tony Lee, Vice President at the Society for Human Resource Management. “A lot more companies now are adopting unlimited vacation time, where they’re allowing employees to take off whenever they need to as long as they fulfill their job responsibility. So that’s key. And then you also have a fairly large number of companies that have created paid time off banks, where you can bank time and it doesn’t differentiate between sick leave and vacation time -- you get however many days a year and if you don’t use a week in 2019 you still have it in 2020. So employers seem to be embracing greater flexibility in terms of time off.”

Per the Bureau of Labor Statistics, the average American has 10 paid vacation days after they’ve been working at their company for one year. If we were in Europe or Australia we’d get double that, but we are not, and thus so we don’t. There are, however, ways to make the most of what you have.

Negotiate when you get the job offer

This is the ideal time to angle for more PTO. When you’re offered a job (congrats!) the first thing you should do is almost always to ask for more money. But if they say no, you should definitely counter by asking about more vacation days. If they say yes (congrats!) you should still ask about more vacation days. 

“An employee should think about vacation time no differently than any other aspect of their compensation,” Lee said. “So they get a compensation package that includes salary, it includes medical benefits, vision, dental, all that. So when they’re thinking about negotiating for time off, sometimes they can move things from one place to another.”

And then again during a performance review and/or salary negotiation

“You’re having your annual performance review and you say, ‘hey, I’d like to talk about a pay increase. I’ve had a great year, you agree that I’ve had a great year, I’d like to look at a potential pay increase,'” Lee said. “If the response is, y’know, ‘eh, it’s not in the budget, we’re not looking at pay increases this year,’ the employee needs to be prepared with what else is important to them that they can negotiate for. So it may be that the most important thing to me is an additional week or time that I can use however I like.”

Especially if you’re in relatively good standing with your employer, you should consider doing this every time you’re inquiring about a raise or promotion or anything else benefit-related. And whenever it’s possible, prepare for the negotiation by asking friends in similar jobs what their PTO package looks like. If it’s better than yours, let your employer know. PTO transparency can be just as useful as wage transparency.


Courtesy of Virgin Voyages

Free time is a non-negotiable, but when it comes to how you spend it, having it your way is essential. No matter your definition of vacation, Virgin Voyages offers it all, from yoga on an open air rooftop deck with unobstructed ocean views to turning up at an exclusive beach club experience in the Caribbean.

Know how much you’re asking for and why

There’s no hard rules about how many more days is the right number to ask for, but an extra week is probably a safe bet. And if you had more vacation time at your previous job -- which is often the case, since you might have been there for years -- you can absolutely make the case that your new employer should at the very least match that number. Frame it as a matter of experience -- you might be new to this job, but the level of experience you’re bringing corresponds that of someone who’s been at the company a while longer, and accordingly receives more PTO. If they say they can’t start you off with the amount you asked for, ask if they can stagger the increase.

“Do a little research before you go in and have that conversation, so you can come in and say, ‘hey, did you realize [tons of] companies do have unlimited time off, or they have paid time off banks and we don’t -- is that something that were considering?’ There’s a lot of research out there,” Lee said with a laugh. “Frankly, as an employee you can find the research you like best and use that.”

Be prepared in case they call your bluff

As with all negotiations since the beginning of time, the real upper hand is determined by who’s more willing to walk away. It’s a tight job market out there, and not everyone can be expected to double down on their request for more PTO and take their talents elsewhere if the boss says no. But if you’re fortunate enough to have other prospects, then you should make sure they know that.

“You have to position it as, ‘look, I’m doing a very effective job, and this is something I need, and if you value my contribution then please consider giving me this additional time off.’” Lee said. “Because remember, we’re in an environment where the next thing you say is, ‘I don’t want to be in a position where I have to find another job where I can get more time off.’”

Always get it in writing

You don’t need a formal contract drawn up or anything, but you should never leave the details of a successful negotiation up to memory. If your boss doesn’t offer to get the increased PTO in writing themselves, politely follow up over email so you have receipts.

“Email’s fine,” Lee said. “What you want is, if you’re negotiating with your boss, then you want to get it in writing from the boss.”

Unionize your workplace

Your boss may well be a lovely person, but they are not your friend, or your family, or whatever else they assure they you they are in your onboarding packet from HR. The best way to ensure that you have equitable benefits and protected PTO and comp time is to be a member of a union. (Disclosure: Thrillist's editorial employees are unionized with the Writers Guild of America, East.) 

Don’t think about PTO just in terms of number of days -- get creative

“Frankly, what we hear about even more [than number of days] is flexibility of schedule,” Lee said. “What comes up a lot is, ‘I have a long commute and I want a flexible schedule to minimize that,’ or, ‘I have care responsibilities and I want a flexible schedule so I can get home by 4 every day to meet my kids.’”

You might want to ask about specific schedule modifications that make things easier for you to manage your other responsibilities. Or, depending on your personal preferences and the nature of your job, about modifications that even come out to the same amount of PTO as before -- like working four 10-hour days four days per week instead of five eight-hour days.

“Remember, for a lot of people it’s not taking extra time off because they’re going to the beach,” Lee said.”It’s because they've got to care for a parent or a child or have an obligation of some sort.”

That said, there’s nothing wrong with using extra PTO to go to the beach. Spend the time how you like -- it’s yours now.

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Kastalia Medrano is Thrillist's Travel Writer. You can send her travel tips at, and Venmo tips at @kastaliamedrano.