Fight for Your Vacation Rights: How to Negotiate Time Off to Travel

If you’re like me, your travels are limited to the days you can take off work. These all-important vacation days are like winning lottery tickets – the key to my freedom to explore the world. I takes a lot of patience to grow my PTO accrual but once I have enough days saved up, I’m booking trips and adventures in a blink of an eye.

A lot of people assume the amount of paid time off you’re given is a fixed amount. What you need to realize is that just about everything is negotiable in the workplace, and that includes your travel time. If you’ve found yourself on the short end of the stick when it comes to time off, it may be time for a conversation with your boss. It can seem scary, but you might just walk away with more opportunities for adventures! Read on for some tips on negotiating extra time off, which you can put towards traveling.

First, take some time and do an honest reflection on your performance and position. If you’ve had a stellar year and have gotten positive feedback and performance reviews, you’re in a better position to negotiate. If you think you’ve come up short on some goals, focus on improving before asking for more perks. Timing your conversation shortly after a formal review or a major project success is always best!

Before you schedule a meeting with your boss, think about what a “win” will look like to you. Being able to directly ask for what you’re looking for makes the process easier and shows you’ve put some thought into it.

Keep in mind that having more time to travel doesn’t have to mean straight up extra vacation days. Sometimes having the ability to work remotely or making up time off by working longer days elsewhere works, too. For example, if I can take a day off and make up the time by working an extra hour for a few days, I get an instant three-day weekend without dipping into my vacation days. If I can work remote, it allows me to work in paradise.

When you finally get into your meeting, get to the point and be assertive. Tell your manager what you would like to see (an extra week off, ability to work remotely one week a month, etc.) and highlight why you feel you are deserving of the extra perk.

Tying it to your great job performance, increased responsibilities, or recent project success is a natural approach to take. In addition to presenting reasons why you are entitled to extra benefits, explain to your boss the positive impacts that traveling more will have – increased morale, better work-life balance, and increased job satisfaction.

If your boss seems willing to consider some remote work opportunities, get them onboard entirely by proposing a trial run. This will help them see that working outside of the office can be productive and viable.

For example, I worked remotely for a week from home as an experiment. I was able to show my boss I could still lead meetings, meet deadlines, and accomplish my workload without being in the office. If anything had gone awry (it didn’t), I could have easily gone into the office which allowed my manager to feel comfortable with the situation. The experiment worked well, and I was able to get my manager’s buy-in after the trial run!

Sometimes you can’t walk away with an instant win. Rather than accepting defeat, see if you can come up with an action plan that opens the conversation later. Maybe you and your boss can identify some key targets or goals that if you meet, you’ll get your extra time off. It shows your company that you aren’t just looking for a benefits handout and are willing to put in the work to get the rewards you are looking for. It’ll help you stay motivated and make that well earned vacation even sweeter.

Your boss may reject your offer – if that’s the case, think of the impact it has on you. Traveling is good for your soul and being able to have a life outside of work is important. If you’re okay financially, see if you can swap your raise or bonus for more time off instead. Otherwise, if you can’t get the time off you need, consider if working for the company you are at is worth it. It may sound extreme, but how will you ever get to see the world if you can’t get the time off you need? Employment is a two way street and you should feel fulfilled and valued as a person.

I followed these steps to negotiate a working environment and schedule that helps me maximize my time off and travel often. Having the ability to see the world motivates me and boosts my happiness with my employer.

Here’s what I’ve been able to work out with my boss in addition to the company-wide PTO all employees get (I’ll accrue three weeks of vacation in 2019):

• Ability to take one day off each pay period (every two weeks) by working a little longer on the other work days during that time. I simply work over lunches two times a week and come into the office a little earlier than I used to in the mornings.

• Increased flexibility to set my hours each day. I’m able to come into the office extra early in order to leave earlier in the afternoon, which makes evening flights or nightime road trips incredibly easy for me. No one likes to waste time off for the transit portions of travel.

• Opportunities to work remotely. By showing my boss that working remotely doesn’t mean I’m any less productive, I have her buy-in to work outside the office occasionally. I’ve been able to fly places for extended weekends and simply bring my laptop to get some hours in. Working by the beach is still a vacation to me!

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How many vacation days to you get a year? If you feel like you’re coming up short, don’t be afraid to speak up and work with your boss. Companies want their employees happy since it often leads to direct, positive impacts on your work. You are in charge of your life. Come up with a goal, pursue it relentlessly, and don’t settle.