How to Travel While Working a Traditional Full-Time Job

Every time I go on a trip, without fail, I get at least one message in my inbox saying “How do you get to travel all the time??! Do you work?!” I figured it was about time for me to address one of the most common questions I receive and give you tips on how you too can travel while working a traditional full-time job.


Traveling with a traditional full-time job, I will admit, is one of the trickiest. When I say “traditional”, I am referring to one with a set schedule (typically 9-5, Monday through Friday, but doesn’t necessarily have to be) and not referring to digital nomads or people working remote who are also working full-time but have more flexibility to travel.


I realize that adding in a spouse and/or children adds on another layer of complexity, but there are great learnings you can take from my tips below that you could apply to your situation.


So before I get started, a little backstory on my professional career... After undergrad, I ran a non-profit in Bali for a bit, then returned to my home in Austin and worked at an advertising agency for three years. This was my first experience with limited vacation days and where I had to learn to strategize if I wanted to continue traveling. From there, I moved to NYC to start business school. During these two and a half years, I had tremendous flexibility to travel given that I was once again a full-time student and had summers, winter breaks, and spring breaks off again. About six months ago, in September of 2017, I returned to the corporate world and since then have had to return to strategizing when it comes to planning my travels. I have limited vacation days and set company holidays again, limiting my flexibility to travel. While it is challenging, it is not impossible.


Below are my top strategies that have helped me maximize the number of trips I take in a year while working a traditional full-time job.


1. Combine your vacation days with company holidays

I touched on this on my Q & A blog post, but this tip is my most important strategy to maximize the length of your vacations and the number of vacations you take a year. Extend the length of your trip by adding on vacation days to an existing company holiday. Even better, take advantage of weekends before/after to truly maximize your trip duration. Say for example, that July 4th lands on a Friday and your company is off. You could take off on a trip Thursday evening after work, July 3rd and return Sunday, July 13th. You just maximized the length of your vacation by combining your company holiday and two weekends, leaving you with a 10-11 day trip while only using 5 paid vacation days! Talk about incredible.


If your company offers Summer Fridays (some companies during the summer give their employees off every other Friday, or half-day Fridays, or some even every Friday off), take advantage of these days off and book a long weekend trip or include this Friday and weekend to your existing vacation. This summer I will have every other Friday off, so I will definitely be taking advantage and planning a bunch of long weekend trips!


2. Do not take random days off just for the hell of it (use your sick days for that)

I treasure my vacation days like gold, so you will never catch me taking a vacation day just because I need a mental health day or to run errands, which surprisingly to me, many of my colleagues do. If your sick days are separate from your vacation days, do not use your vacation days for random lounging at home or just to run errands. Most company policies allow you to use your sick days for mental health days or to go to medical appointments, so always use your sick days before taking a vacation day.


Similarly, if my flight leaves at 4pm, for example, I am only going to ask for half a vacation day from work rather than a full day because that half day will come in handy during another trip.


Be methodical about when you take days off and treasure those babies like gold!


3. Book travel as early as possible

One of the biggest negatives of traveling while working in a traditional job is that most of your trips now fall during high-season times. Everyone is traveling during major holidays, so prices will generally be higher.


If you know you will be traveling during high-season times, you should book your flights as early as possible! In all my years of travel, I have rarely seen ticket prices go down from when I originally looked. Most of the time, ticket prices will only continue to increase as the date approaches and less seats become available. This is very much true for holiday dates and major events like Coachella, the Olympics, or the World Cup to name a few. If you know you want to take advantage of your holiday weekend, look at flights months in advance. Don’t worry about having all the details of the trip ironed out before-hand; book the flight, then worry about the details.


Similarly, what I do if I know I want to travel a certain weekend I will usually book my flight before waiting for friends or family to decide whether they want to join. I am still annoyed at myself for waiting for friends to decide if they wanted to take a trip together for President’s Day weekend, because as expected, we waited too long for everyone to decide and then flights got too expensive and we went nowhere. As much as I love my friends, I won’t be making that mistake again. On the other hand, I have booked flights on my own and then invited friends to join and they have! My strategy is to buy my tickets in advance, being fully ok with it being a solo trip, and if friends want to join then terrific! It’s a win-win in my book.


4. Don’t pick a destination, pick a low price

Because you are likely traveling during high-season times, do not focus on booking your flight to specific dream destinations. Focus instead on finding which locations are the cheapest during this time. I have highlighted step-by-step instructions here on how I use Google Flights to see the prices during a certain date for ALL places in the world in one handy interactive map. I have also included instructions on a tool that allows you to see what the flight prices are on any given day once you narrow down your destination.


Traveling during high-season holiday times is not the time to focus on your bucketlist destinations. If your bucketlist destination happens to be the cheapest option during your travel dates then amazing, but if not, go somewhere else that’s awesome and save the bucketlist destination for a low-season travel time. Keep in mind that low-cost destination doesn’t necessarily mean boring, you may just discover other incredible destinations that you didn’t realize were affordable to travel to during this time!


5. Consider celebrating certain holidays abroad (& bring your family along!)

I know this might not be something you’ve considered doing, trust me, the first year my mom told me we were traveling together during Christmas I was not a happy camper. I have lived in various parts of the country and abroad and coming home for Thanksgiving, Christmas, and New Years were non-negotiables for me. However, after doing this a couple years now, traveling with my immediate family to different destinations for Christmas and/or New Years, I came to realize that what was most valuable to me was getting to spend that quality time with the ones I loved and missed the most. Personally, I enjoy spending Thanksgiving and Christmas at home, but I have loved spending the New Year in a new part of the world and starting off the new year doing what I love most!


If you happen to not celebrate certain holidays (for example, Christmas) and have these days off at your company, even better! Make use of them and go on a vacation!


As I mentioned above, flights tend to be pricier around holiday times, so keep that in mind. You will need to take my tip #4 to heart on this and pick a destination that’s affordable during these days and leave the bucketlist for low seasons. The company I work for closes for 10 days between Christmas and New Years which is amazing; however, it means that I will almost always be traveling during high-season and will need to strategize as much as possible.


Well, there you have it; my top (not-so-secret-anymore) strategies on how I manage to always be traveling while working a traditional full-time job. Whether you have children, a spouse, or traveling solo, apply these strategies as you’re planning out your travels for this year and years to come!


Til next time!

❥ Ashley


Be sure to pin this image below to your Pinterest board!