How To Vacation Like A Boss On An Entry-Level Budget

Getting your first post-grad “professional” job is an exciting time. All of a sudden, you’re being paid more money than you’ve ever had in your life, plus you’re gaining a host of mysterious “benefits” like healthcare, 401(k)s, commuter perks, and other fun things that you aren’t quite sure what to do with. Among this list of acronyms benefits, is every traveler’s pot of gold: the vacation time, known in HR acronym jargon as PTO. If you’re anything like me, after working years of hourly summer jobs and school-year internships, paid vacation seemed like a luxury that is too good to be true.

After the excitement over your shiny new professional title wears 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. You also realize that the amazing free vacation time that you’re paid to take, doesn’t leave you as much time to travel the world as you initially thought.

I’m lucky that I have a very generous deal for an entry-level hire. I receive 15 days of accrued paid vacation, which accrue at a rate of one and a quarter days per month. These roll over every year, so if I don’t use them up, I get to keep them. I also get three personal days, which do not roll over. This gives me a total of 18 vacation days. I also accrue sick days at a rate of one 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.

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 (because we get a generous holiday break). At this stage in my career, I feel rich in vacation time, but in comparison to more senior colleagues, not to mention our European counterparts with their five weeks of vacation time, my vacation package seems less grandiose.

Here’s how I’ve been able to make the most of my vacation days with an entry-level contract, and an entry-level budget:

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

2. 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.

3. If you’re lucky enough to get to travel for your job, see if you can tack on a few extra days to explore 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 domestic 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.

4. 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 have 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 of business days. Doing this means you can have that one 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.” Finally, this can provide a neat opportunity to get to know some of your global colleagues, and maybe even get invited to some local events and activities.

5. If your office has it, take advantage of summer hours. Many offices in the U.S. have flexible hours in the summer months, which often 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.

6. If you get time off during the holidays, 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 holiday getaway. 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.

7. If you’re dreaming of more long-term travel, having a full time 9-5 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, who is a little more senior than me (she gets 20 days of vacation annually instead of 15), spent 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. This one is more complicated than simply asking for a week off a few months 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 to use the vacation. Summer is a good time to take off, because most companies tend to slow down in the summer.

Note: You should only try this one if you’re in good standing with your employer. I wouldn’t recommend making this ask after only three months on the job, for instance.

8. The final, and most important point, is to use your vacation days. 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 accepting 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 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?

Amani is a 20-something young professional living in Boston, who enjoys a strong cup of tea, a good political debate, and travel, not necessarily in that order. She writes about travel and the 9-to-5 grind on her blog.

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