How to Ask Your Boss for More Vacation Time (The Right Way)

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Don’t get me wrong. I think you should love (or at least like) your job. A fulfilling career is one of the most satisfying things ever, and I hope that you have found, or are on your way to find, one. But no matter how much you adore your career, no matter how much it ‘doesn’t feel like work,’ you should still have boundaries. And everyone – you included! – deserves a break. 

It’s no secret that the United States has historically fallen short when it comes to shelling out paid vacation time. While some countries commonly offer up to a month (20 - 30 days) of paid time off for full-time employees, the United States hovers closer to just 10 days – two weeks for every ~50 weeks of work, and even that isn’t guaranteed. 

Over time, all this vacation suppression has created a sort of ‘fear’ culture around being away from the office. Situations like these are all too common in the average American workplace:

  • Hearing office gossip about how taking time off is bad, and will make you look like a careless employee

  • Learning that being on vacation might make you less likely to get promoted, or less likely to be respected by your peers 

  • Seeing your managers and/or execs not leading by example (i.e. never taking a vacation themselves) 

  • Being denied vacation requests for ambiguous or subjective reasons 

  • Receiving backhanded comments from coworkers or colleagues after coming back from your time off 

It’d be one thing if vacation time was just about appearances. But it goes so much deeper than that. Taking a break every now and then has been proven to make you happier, more balanced, and actually enjoy your life (and your work) more!

Let’s get into it.



The Time-Off-To-Happiness Ratio 

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Now, I don’t mean to be a downer about American vacation days. But I do believe there’s a lot of room for improvement. Lack of vacation time can result in pent-up stress, burnout, and depression, especially if work is causing you to miss out on trips with family or big life events like weddings and birthdays. In fact, it’s no surprise that the United States consistently ranks among the most stressed, angry, and worried nations in the world. 

On the flip side, American vacation culture is slowly beginning to see improvements in recent years. Americans are, on average, using more vacation days, and American employers are, on average, offering more vacation days year over year since 2015. But it wasn’t long ago (the ‘70s and ‘80s, to be exact) that Americans were actually enjoying an average of 20+ days of paid time off, and only now, decades later, are we finally inching back up towards closing the gap. While some companies are embracing new trends like unlimited time off or minimum suggested vacation policies, the majority of private sector company policies still look a little more like this:

  • 10 days after 1 year of service

  • 14 days after 5 years

  • 17 days after 10 years

  • 20 days after 20 years

That’s 20 years of work in the United States in order to earn the same vacation days as most entry-level Europeans. 

People who use their vacation time to travel, spend time with friends and family, and take care of their mental health are significantly happier and more productive at work. So… if you want to travel more and miss out on life events less, what should you do if you don’t get enough time off in the first place?

How to Ask Your Boss for More Vacation Time (The Right Way)

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When Accepting a New Job Offer

Evaluating or accepting a new job offer is usually one of the most ideal scenarios for negotiating additional vacation time. Your new employer expects you to negotiate during this phase, and they’re likely pretty eager to have you join the team, so use this knowledge to your advantage and carefully consider what kind of work package will make you happy, and respectfully make that request known. 

While most new offer negotiations are focused around salary, vacation time is another big topic to bring up. Explain how work-life balance (or travel) is important to you, and how it is one of the biggest things you take into consideration when evaluating a new work opportunity. Then, be prepared to explain how you will (or have in previous roles) demonstrated the ability to take time off while ensuring none of your work falls through the cracks. It’s also important to address whether your new employer’s vacation package is less generous than your current policy, in which case, you’d at least want them to be able to match what you currently receive in order to sweeten the deal. 

If your new employer can’t make any concessions about vacation time for whatever reason, consider whether other alternatives might satisfy your needs. Some questions you can ask:

  • What is the sick day policy, and can sick days be rolled over into PTO?

  • Can employees work remotely? Once a month? Once a week? Can you negotiate a weekly, or biweekly, WFH policy for yourself? 

  • Can you take a slightly lower salary in exchange for additional vacation time? 

  • Can you take unpaid time off, if needed? 

  • Do you have a flexible work schedule, or fixed hours?

When Asking for More Vacation Time from Your Current Employer

1. Get Familiar With Your Company’s Vacation Policy

The very first thing you should do is take out your company handbook. Look into and familiarize yourself with your company’s specific vacation policy. 

  • How many days are you offered? 

  • How does paid time off (PTO) accrue? 

  • What happens if you don’t use all of our vacation days in a calendar year – do they roll over or disappear entirely?

  • Is your sick day allowance bundled together with PTO, or separated?

  • Are you allowed to take unpaid time off if you max out on your PTO? 

If you’re considering a new opportunity elsewhere and trying to determine whether your current vacation time package will be a make or break, consider using your familiarity with your company’s policies as leverage and negotiate what you’d like your employer to provide, compared with what other offers might be on the table for you that are more generous. And, even if you’re not evaluating other offers, you can use this knowledge to help you prepare for a larger discussion with your manager regardless. The last thing you want to do is go into a negotiation and not know exactly what your policy does and doesn’t allow!

2. Plan Around Your Next Performance Review 

If you know you’ve done a stellar job and are expecting your next performance review to go really well, use this opportunity to ask for more time off, just like you would if you were negotiating a raise. 

It’s easy to get a bit emotional or heated when it comes to performance reviews, especially if you feel that you’re deserving of more than what you currently receive, but do your best to keep a positive, yet resolute, attitude. If you feel the conversation is going well, bring up your request for additional time off and see whether it’s something your company can accommodate. Here are a couple sample points you could try on for size:

  • I really enjoy working here, but additional time off would keep me happier and more productive at this company.

  • Would you be open to giving me an additional [X amount] of vacation per year in recognition of the hard work I’ve been doing, and the value I’ve been adding to our team?

  • I appreciate the positive feedback on my performance! I would be interested in discussing an increase in vacation time in lieu of a raise. Is that something you would be open to exploring? 

3. Prepare Proof Points 

When going into this conversation, assume your higher-ups need a refresher on all of the things you’ve done for the company, and come prepared to do some show-and-tell. Write down everything you’ve contributed – every goal you’ve achieved, every way you’ve enhanced your team, and every way you’ve grown since your last review. Bolster your argument with numbers, stats, or testimonials from peers, if you can get your hands on them. You need to be able to show your boss that you are extremely serious about the importance of taking time off, and you have the work performance to back up your worthiness of a PTO bump.

It could also help your argument to show how much you’ve contributed relative to how much PTO you currently receive. If you only have 12 days of PTO but you’ve been at your company 3 years, it could also simply mean you’re overdue an increase but it just hasn’t been discussed yet. 

Finally, consider whether or not the topic of wellbeing and avoiding burnout can help your case. Sometimes, explaining how many hours you put in on work, relative to the vacation time you receive, could use a reevaluation, and that you believe you could perform at an even higher level mentally and emotionally if you were offered some additional paid days off to relax and recharge. 

4. Time Your Ask Appropriately

Time can either be your biggest advantage or your biggest roadblock in this circumstance. If your company is having a challenging quarter or you’re in-between review periods, it may not be the best time to broach the subject of increasing your benefits. On the flip side, if your company is doing well and your team is in high spirits, or if you’ve just completed a massive project or up-leveled your responsibilities in some significant way, it could possibly be a great time to request a reevaluation of your vacation package. 

5. Get It In Writing 

If you are able to successfully negotiate additional PTO days, many companies will draft up a formal offer or notice that will reflect the change in compensation offered. Make sure you receive this documentation to review and sign off on. If not, start an email thread with your manager or HR team to seek written confirmation that you can reference later on, if needed. 



How to Use Your Increased Vacation Time

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1. Actually Use It!

This may seem obvious, but once you do receive increased vacation time (or, before you make your request, to prove that you are someone who actually values this benefit), you should actually use it. Sounds like a no-brainer, right? But you’d be surprised – Americans aren’t actually very good at taking time off. We just haven’t been conditioned to feel comfortable with it, or to save for it. In fact, in 2019, Americans left 768 million days of vacation time unused. What’s worse, a big chunk of those unused days were forfeited completely, adding up to over $65 billion in lost benefits earned after hours and hours and hours of hard work.

Now, I get it. It’s easy to feel a bit concerned about taking time off, especially if your office has created a bit of a culture around needing to be physically present in the office at all times. But, remember, the benefits you receive are yours to exercise. Your vacation package, if you have one, is written in a contract that you agreed to upon being hired. If you have any concerns about exercising your PTO, talk to your boss or your HR department who should be able to assist.  

Not sure where to go? Ease in and start close to home with a domestic getaway! My favorite USA travel guides can all be found here.



2. Schedule Your Vacation Time Well in Advance

It’s always a good move to put in any vacation requests well in advance, especially if you’re hoping to take more than one or two days off. The extra time will help you and your manager be able to prepare accordingly for your absence, assign any needed coverage, and manage outstanding projects ahead of time. 

If you know the time you’re requesting off is during a high-volume business cycle or the end of a quarter, it may help to also explain why you’re asking for these specific days off when submitting your request (i.e. a big life event or a family member’s wedding may be very good reasons to need the first week of Q4 off from work, and that context may compel your manager to more graciously evaluate the request). Additionally, you could also take this opportunity to present a plan for how your responsibilities will be tended to in your absence. 

3. Consider Off-Peak Timing for Vacation Requests

Whenever you can help it, aim to put in vacation requests at the times that will be most convenient for the company and for your team. Peak times (such as the summer and holidays) might be the most highly requested days your peers are seeking out. If you plan on traveling more frequently, try to be flexible about your requests and considerate of your other team members’ needs, and work around their vacations if you can.

For instance, if you know you want to travel in November but the rest of your team is planning to take the week of Thanksgiving off, offer to take your vacation during the first half of the month so you can be back before Thanksgiving and cover for another employee(s). 

4. Make Having to Cover For You as Effortless as Possible 

The more time you take off, the more susceptible you could become to judgment or scrutiny by other team members, even in the most casual of office settings. Whenever you’re planning to be out of the office for an extended period of time (more than 1-2 days), take all necessary precautions to assign coverage and tie up any ends with projects you’re working on so that nothing falls through the cracks in your absence. Empowering your team by making covering for you as easy as possible will go far in terms of proving you can be trusted to maintain a high output of work even when you’re not in the office. 

It also never hurts to thank your teammates profusely for covering for you, especially during busier times of the year. A cup of coffee, a gift card, or a quick lunch as a ‘thank you’ can go a long way, and could help demonstrate to your colleagues that you’re grateful and willing to return the favor the next time they’re thinking of taking time off. Taking time off isn’t just about whether your boss says yes or no. It’s also just as important to maintain a supportive and understanding relationship with your peers, so that you’re all equally helping one another to find work-life balance.

At the end of the day, and as cliche as it sounds, it really doesn’t hurt to ask when it comes to requesting more time off. The American workforce is slowly shifting its mindset towards work-life balance, but it’s up to you to evaluate whether your unique employment situation meets your needs or if there’s work to be done!


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How to Ask Your Boss for More Vacation Time (The Right Way) - Rachel Off Duty
How to Ask Your Boss for More Vacation Time (The Right Way) - Rachel Off Duty