How to Maximize Your Entry Level Vacation Time

Me, using my vacation time in Brussels

Getting your first “big kid” job is an exciting time. All of a sudden, someone is paying you more money than you’ve ever had in your life along with a suite of mysterious “benefits” like healthcare, 401K’s, commuter benefits, and other fun things that you aren’t quite sure what to do with. Among this list of acronyms benefits, is every wanderluster’s jackpot, the vacation time, commonly known in HR acronym jargon as PTO. You mean they’re going to pay me for not working, what?! If you’re anything like me, after working years of hourly summer jobs and school year internships, this seemed to good to be true. But it IS true. Cha-ching.

After the shiny newness of your first big kid job starts to wear off, you realize that the salary which was more money than you could even fathom spending when you took the offer doesn’t actually leave you with a whole lot after bills and that you actually should maybe figure out what the heck a Roth IRA is and whether you have one. You also realize that the AMAZING free vacation time that people are paying you to take, doesn’t actually leave you with as much time to travel the world as you initially thought it did.

With Scrooge McDuck money pit and endless vacation dreams squashed, it’s time to start thinking strategically. Most entry-level jobs offer a range of PTO that falls somewhere between 10-15 days of vacation. Some offer more, few offer less than 10. Some employers will roll sick days and vacation days into one category, others will separate them out. Christmas is another hit or miss benefit, with some employers giving a certain stretch of the holiday period off, and others just offering Christmas and New Year’s Day.

Scrooge McDuck dreams crushed, image via

In the interest of transparency, I will share what I receive as part of my benefits package. I’m lucky that I have a fairly generous package for an entry level hire. I receive 15 days of accrued paid vacation, which I acquire at a rate of 1.25 days per month. These roll over every year, so if I don’t use them up, I do get to keep them. I also get 3 personal days which do not roll over, so I’ve got to be careful and make sure those have been used by the end of the year. This gives me a total of 18 vacation days. I also accrue sick days at a rate of 1 day a month, which is nice, because if I get sick I don’t have to worry about the days dipping into my vacation pot. In addition to federal holidays, I also get from noontime Christmas Eve until January 2nd off, which including weekends, means nearly 9 days off at the holidays.

As I said, I’m pretty lucky in that I’ve got a decent amount of vacation time, separate sick and vacation funds, and I don’t have to take any vacation time off for obligatory family festivities at Christmas ( I mean I would want to take this time off, but it’s awesome that I don’t have to).

At this stage in my career, I feel rich in vacation time, but in comparison to more senior people, not to mention our European counterparts with their 5 weeks + vacation time, mine looks less grandiose. How many vacation days I have left is absolutely a top determining factor on what trips I can take and when.

That being said, I’ve picked up a few tricks over the course of my first year in the “big kid” world of PTO that can help you stretch out your vacation time as much as possible.

Be strategic about timing vacations with holidays. Memorial Day, Columbus Day, etc. especially for the international flights; these aren’t too impacted by holiday price hikes. Leaving on a Friday after work and staying through to the following Sunday gives you a 9 day vacation using only 4 precious vacation days.

Book the night flight, book the night flight, BOOK THE NIGHT FLIGHT. Honestly, I can’t say this enough. Booking the night flights prevent you from losing a day of vacation through travel. You might be a bit groggy on day one when you arrive, but don’t waste two of your vacation days on getting to and from your destination.

If you’re lucky enough to get to travel for your job, see if you can tack on a few extra days to explores where you are or go to another nearby destination. This is the ultimate budget travel pro-tip, because the company will pay for your ticket and all you need to cover is your expenses for the days you aren’t working. For example, when I was living in England, I went on a work trip to San Francisco, took a cheap internal flight from San Francisco to Boston, visited my family for a few days, and then flew back to London. My flights from London to San Francisco and Boston to London were covered by my employer. You can also do the even cheaper option of staying at the destination for an extra few nights. This is great on those business trips that take you somewhere you’ve never been before and are super pumped to see, but end up being all business and no sightseeing for the work portion. All it costs you is accommodation and food for the extra days you are there!

On a similar note, if you work at large company with international offices but don’t have a ton of vacation time, see if you can work remotely at one of the international offices. I’ve had friends who have done this, planning vacations for a week or two, but then dropping into the local branch of their company and borrowing a free desk for a couple business days. Doing this, means you can have that one week or two week vacation, even if you don’t have quite enough vacation days to get there. It’s also a good solution to pacify your boss for those of you working in offices that “couldn’t possibly manage, if you took two consecutive weeks off”. This can also provide a neat opportunity to get to know some of your global colleagues and maybe even get invited to some local events and activities.

If your office has it, take advantage of summer hours. Many offices in the U.S. have flexible hours in the summer months. This can mean a variety of things, but most typically means that they let you out early on Fridays. I have a friend whose office gives her a couple extra vacation days, to be used in the summer. In my office, we have the option of working a few extra hours Monday through Thursday, and then taking Friday’s entirely off.  Whatever your summer office perk, take advantage, it’s a fantastic way to squeeze in some extra weekend trips without dipping into your PTO bank.

If you get time off at Christmas, use it! Holidays are a tricky time because you’re expected to be certain places, but if you’ve got the time off, see if you can rally the other adventurers in your family and propose a Christmas vacation. A friend of mine convinced her family to go to Bermuda for the holidays last year, and they loved it so much they’ve decided to make it a new annual family tradition.

If you’re dreaming of more long-term travel, having a full time job doesn’t mean that the dream has to die. This one is a little trickier to negotiate, but it is possible. If your job allows vacation days to roll over, consider talking to your boss (many months in advance), about your ambition to take a long term trip. One of my colleagues, a little more senior than me, so I think she gets 20 days of vacation annually instead of 15, is spending the entire month of July in Ghana. She made it work by limiting her vacations to weekend getaways and saving up her vacation time for about a year and a half, and now she’s off on this amazing trip for what feels like an insanely luxurious amount of time. This one is more complicated than simply asking for a week off a month in advance, because you need to be able to leave your job responsibilities for an extended period of time. You’ve also got to be smart about when you ask for the time. Summer is a good time to take off, because most companies tend to slow down major business in the summer. Asking in the height of busy season? Not necessarily the smartest strategy. Not all employers will say yes to an extended vacation, but if you don’t ask you’ll never know. If you’re willing to be flexible on the time and give lots of notice, your employer might be able to accommodate. Not taking a proper vacation for a year and a half sounds extreme at first glance, but when you think that most people only take about one major vacation a year, waiting a few more months to have enough vacation for the trip of a lifetime doesn’t sound all that bad.

The final most important thing is to use your vacation! I am adamantly against the aspect of American work culture that frowns upon using up your vacation days. Would you decline one of your pay checks because you felt guilty accepting the money? Hell no. So don’t decline to accept your vacation time; it is part of your compensation package just like your salary. Don’t allow peer pressure to dictate what is rightfully yours. In fact, I just came across this article in the Harvard Business Review
a few weeks ago which suggests that people who use their vacation time have a 6.5% higher chance of getting promoted than those who leave large amounts of vacation time on the table. Do you need any more of an excuse?

Get out there and explore, wanderers! Are there any tricks of the trade that I have missed?


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