The Art of Conversation: How to Ask Your Boss for More Vacation

This year, I made the goal to travel more and spend more time with my family. Thus far, I have to admit that I've been pretty successful at doing both. Unfortunately, the U.S. is the only developed country that does not mandate vacation time— instead vacation time is seen as a perk. When employees do earn vacation time, it is generally only 2 weeks. Furthermore, many employees do not use all their vacation time because of fear of being laid off for doing so or of falling behind. Look, if you have this mentality: STOP IT! USE YOUR VACAY TIME GIRL!

After my most recent trip to Costa Rica, I felt inspired to put together this list of conversations you should have with your boss to gain more vacation time.

Talk to your boss about working remotely.

Why: Working remote provides you the ability to work from anywhere. Well, within reason, because you will need to take into consideration time zones if you work closely with others. At the minimum, with one “work from home” day per month, you can catch an evening flight 1 day earlier— for example, by working remotely every other Friday, now you can catch an evening flight on Thursday after work. Imagine waking up in your destination for a local breakfast, clocking in your 8 hours, and now having an extra evening to enjoy your new environment.

How: If your company (or even team) already had remote employees, great for you. Your conversation may be easier with your boss because he or she may have already experienced success with other remote employees. Before having this conversation with your boss, you should really take an authentic, objective look at your performance and responsibilities. If you are a high performer, proceed. If not, it's time to get realistic and improve your performance first. If you supervise others or have many in person meetings, there may be challenges with this work arrangement that you will need to address first. After all, remote or work from home arrangements are corporate privileges, not rights. Some remote arrangements you may want to consider is: 1 floating remote day per month, remote day every other Friday, and even remotely working permanently. You can read a good guide on how to approach your boss about the possibility of working from home here!

If traveling on the company’s dime, ask your boss if you can extend your trip if you find an equal or lesser value flight.

Why: If your work related business ends on Friday, you can extend your trip for 1-2 additional days with a major expense, airfare, comped. Obviously, this arrangement will leave more money in your pocket to either save for future use or to splurge on enjoying the city.

How: Review your company’s travel and reimbursement policy. Clarify any questions you may have about the policy with your boss. Then ask your boss about the company’s travel policy to see if this arrangement is permissible and if he or she approves of your proposal. If so, find a flight of equal or lesser value to extend your trip through the weekend. Be sure to affirm your agreement to pay for your extended hotel stay, food, and additional travel during the leisure stay of your trip. If your boss doesn't seem swayed, you may consider emphasizing how this arrangement is not costing the company additional, or may even save the company money. Plus, remind them about the benefits of vacation on employee retention and productivity.

Selfie game strong! Visiting the  Sheikh Zayed Grand Mosque . This moment was made possible because I asked my new job for unpaid time off during my new employee probationary period to visit the United Arab Emirates: Abu Dhabi and Dubai. 

Selfie game strong! Visiting the Sheikh Zayed Grand Mosque. This moment was made possible because I asked my new job for unpaid time off during my new employee probationary period to visit the United Arab Emirates: Abu Dhabi and Dubai. 

When accepting a promotion or new job, negotiate for additional vacation time.

Why: Vacation time is literally valuable. Each day of vacation is a day of income. This is a reason why when you leave your job, you are legally entitled to receive a monetary payout of your remaining vacation bank. Some companies are more willing to provide more vacation time versus more base salary because it costs them less. Additionally, a recent poll suggests that millennial are more willing to take a pay cut to gain more vacation time.

How: Instead of focusing solely on salary during negotiations, especially if your offer is competitive, consider asking for more vacation days. I personally haven’t had experience navigating this conversation, but I know friends who have successfully (and some not successfully) broached this conversation with their bosses. To learn several strategies on how to have this conversation with your boss, you can check out this article!

Talk to your boss about mental health days.

Why: I personally do not believe that employees should have to use vacation time for mental health recovery. Honestly, I feel it's unethical. If you battle with anxiety, depression or any other mental illness, heck even overwhelming stress, you should be able to use your sick to recover or recharge. After all, both corporations and employees benefit when mental health is taken seriously.

How: Fortunately, my current department seems to respect mental health— granted I work in healthcare and my department hires social workers and behavioral therapists. When I need a mental health day, I generally just text my boss that I need to take a sick day—no additional excuse or explanation given. We also have an internal policy in my department where our supervisors are not supposed to discuss details of our time off requests with other employees. If you do not know where to start to discuss mental health days with your boss, read this! If you have a mental health concern and you do not know how to discuss your mental health with your boss, read this article here!

Talk to your boss about an alternative work schedule.

Why: Employers are starting recognize more and more the importance of time off for increased productivity of their staff. With an alternative work schedule, you can earn guaranteed days off that you can use for vacation.

How: Normally, when we think of an alternative work schedule we think of flexible hours. For example, employees must arrive to the office between 7-9 AM and can leave the office between 4-6 PM. However, alternative work schedules also include compressed work schedules where you can work longer hours but fewer workdays. There are two common flexible working schedules that I know of: 9:80s and 4:30s. A 9:80 flexible work schedule is where you work 80 hours in 9 days— the 10th day is your flex/off day. A 4:30 flexible work schedule is where you work an extra 30 minutes 4 days a week for 4 weeks—the 5th day in the 4th week is your flex/off day. In some industries and companies, you may be lucky to find that these sorts of schedules are the norm (e.g. energy industry). However, if your company does not offer this arrangement up front, does not mean that you shouldn’t ask. You can learn how to request this arrangement from your boss by reading this article!

Crossing a hanging bridge more than 120 feet above the rainforest floor in the Arenal Volcano National Park in La Fortuna, Costa Rica. The views of the volcano and rainforest canopy were spectacular.

Crossing a hanging bridge more than 120 feet above the rainforest floor in the Arenal Volcano National Park in La Fortuna, Costa Rica. The views of the volcano and rainforest canopy were spectacular.

The above conversations definitely will take more effort and planning on your end. After considering which conversations may fit your needs and workplace, I think they are worth having with your boss. But, not all conversations will require preparing in advance a strategy. The following are conversations about vacation time that are more straightforward.

If you are an hourly worker, speak with your boss (and colleagues) about covering extra shifts.

Why: This is the perfect way to demonstrate your teamwork to your colleagues. By covering them while they are out, they will be more willing to cover you while you are out. Covering extra shifts will also help to pad your pockets so that you are not “losing” money while you are out.

How: Give your boss ample time to know your future plans. Explain to him or her that you are willing to cover additional shifts and secure a colleague to cover your shifts while out. In the days leading up to your vacation, be sure to volunteer for extra shifts when they become available.

Ask your boss if that is okay to use other paid time off (e.g.personal, family) in conjunction with vacation time.

Why: Your boss may be more than willing to let you tack on a few days of additional paid time off to extend your vacation.

How: Literally, just ask. Lol

Ask your boss to take unpaid time off.

Why: When joining a company as a new employee, after promotion, or when transitioning to a new department, you may find yourself in a probationary period where you are technically not allowed to use your vacation time. However, many employers are reasonable in granting unpaid time off for previously planned activities. If you are not in a probation period and find yourself a few vacation days short of being able to take a needed vacation, your employer may very well be fine with letting you extend your travels with a few days unpaid.

How: Once again, just ask. haha

Discuss earning compensatory "comp" time.

Why: For example, you typically work Monday through Friday. There is a special event on a Saturday that you have to work or volunteered to work. Consider, talking with your boss about using the additional hours worked as comp time for a later vacation.

How: You have the pattern now… simply ask. HA!


Have you had any of these conversations with your boss? How did it go? Did I miss a conversation? If so, share your conversation below!