How to Work and Travel: The Ultimate Guide to Traveling with a Full-Time Job

How to work and travel - F*ckity bye - funny travel blog

I talk a lot about different ways of putting together money to travel on this blog (restructuring your spending habits, making money online, etc).

As it turns out though, a lot of the adult world is already making money via a traditional, full-time job or as it's called in the "Oxford English Dictionary":

A 9 to 5 (noun) /Ay•Niyn•T-ooh•Fai•v/: Having stable work from 9 am - 5 pm in exchange for your mortal soul.

Alright! I admit that's not the Oxford definition of a full-time office job.

I also admit that I'm probably projecting some of my more negative personal experiences here. Some people love their job and wouldn’t trade it for anything in the world! Kudos to those of you that feel that way and let me know if your place of employment is hiring (I'm begging you).

Whether things are going well at your job or not, if you're working full-time and are interested in traveling the world you've probably run into the same problem most people in your position have -

A lack of time.

Therein lies the catch-22 of how to work and travel:

"I had time to travel but no money, so I got a job to fix that problem and now I have money to travel, but no time."

In helping people manage this dilemma, I've arrived at four solutions about 99% of the time that we will quickly explore over the course of our ultimate guide on how to work and travel with a full-time job!
(Cue my super cute "numbers cut out of orange construction paper" header icons!)

number 1 icon on orange construction paper with drop shadow | fckitybye.com | by Ryan Somohano

Fit Your Travel Dreams into Your Company's Vacation Allotment

At most companies, you’re allowed two weeks (10 business days) of vacation time each year. If you let your team know in advance that you’ll be taking your full two weeks consecutively, you should have no problem getting that time approved.

If you feel like traveling is only going to be possible during your allotted vacation time, consider using a few of these techniques below to try and squeeze a couple more vacation days into the mix:

Wrap Your Time off Around a Company Holiday

Traveling on (or very close to) a holiday is expensive given airfare hikes. But if a holiday were to fall in the middle of your traveling, since you'd normally have that holiday off, it wouldn't count as one of your vacation days and your airfare shouldn't be inflated.

Let me clear that up with an example - If you normally get Memorial Day off, coming back on the Monday of Memorial Day (or even within a couple of days of it) is airfare suicide. If you were to leave on a two-week trip the week before Memorial Day though and came back the week after, you'd get a free day off in the middle of your adventure (since your office is closed on memorial day) and you'd pay normal flight prices since you didn't fly in close proximity to the holiday.

Bookend Your Time off with a Non-Travel Holiday

You can technically start or end your trip on or within a couple of days of a holiday and not overpay for airfare. The only catch is that the holiday needs to be a non-travel holiday.

This type of holiday that I've found the most success with is Martin Luther King Day. A lot of offices do not shut down for MLK day and most people who do have the day off won't be traveling so airfare remains largely unaffected.

Stockpiling Hours

This is a trick I have found a lot of success with and if you have a reasonable manager you can too!

What you do is arrange to work extra hours each day and for those extra hours to count towards time off. For example, if you want to add two extra days to your travels, that's sixteen hours of paid time off you'd need (assuming you work an eight-hour day). That means, if you work an extra hour every day for sixteen days, you could accrue the two days you need and extend your paid vacation by that time!

Get Sneaky

This is the old, "calling out sick the day you were supposed to return from vacation" trick. Unless you're new to the workforce, my guess is you've either tried this move yourself or have given the stink eye to another employee you've suspected of pulling this stunt.

There's no way to avoid suspicion if you do this but at the end of the day, if you don't do it often, silent suspicion is all the blowback you're going to endure.

If calling out sick seems too obvious, you can get more creative and say your flight has been delayed due to weather, technical issues, a sick passenger, etc. Just make sure you know your manager well enough to safely assume that they won't do too much digging (for example, if you work for a private investigator you probably want to avoid everything in this paragraph).

number 2 icon on orange construction paper with drop shadow | fckitybye.com | by Ryan Somohano

Ask Your Company for Unpaid Time Off

If you have dreams of spending a month in South America but cry yourself to sleep at night knowing you won’t be able to do that until you retire, consider having that conversation with your manager. You’ll probably want to leave the part about crying yourself to sleep out, but if you let her/him know what your aspirations are and they value you as an employee, they'll probably work with you.

When asking to add additional unpaid vacation time onto your company's paid vacation allotment, it may be that your manager tries to haggle with you on the amount of time off you're asking for. Be prepared to either negotiate or have a good response ready to impress upon them the importance of getting all the time you're asking for.

You're welcome to use my pre-written ask below:

"Your counter proposal is completely reasonable and it means an incredible amount that you're willing to work with me on this but I can't impress upon you enough how big of a dream this trip has been for me. I'm asking you for a month off because I've thought about this for years and I know that's the amount of time I need to fulfill everything I'm setting out to accomplish. I understand the position that puts you in and I feel bad for having to impose on you this way but this isn't a vacation for me, it's something I need to do. I'll come in early, I'll leave late, I'll do anything you want me to do, just please... work with me on making this dream happen for me."

number 3 icon on orange construction paper with drop shadow | fckitybye.com | by Ryan Somohano

Get Approval to Work Remotely

If you’re fortunate enough to have a job that you can technically do anywhere with an internet connection then tell your manager that you’d like to travel for longer than your vacation allotment and would be willing to work on the road for the additional time you're requesting.

This is a practice commonly referred to as telecommuting.

If you work for a major company you might be surprised as to the infrastructure that's already in place that allows you to do this. One of the years I was working an office job I was getting sick A LOT (probably my body going on strike against the work stress it was constantly under) and amidst my badgering people for work-from-home solutions so I wouldn't need to come in ill, it was discovered that my company had software I could install on my work laptop that would allow me to access its network from anywhere in the world!

Talk to your manager about what's possible and if they don't have any information, ask your company's IT person for a solution.

Another angle you can try is if your company has branches in other parts of the world, you can ask if you can work out of a more exotic, alternate office location for a period of time.

This solution has the added benefit of you interacting with colleagues from another part of the world and exchanging workflow solutions. Your manager may see this as an opportunity that could end up benefiting the company and consequently, may be more open to giving their approval.

Now I get that working remotely while traveling means WORKING while TRAVELING, but hey, I’d rather work from a beach in Jamaica than from an office in New Jersey. When 5 pm rolls around you can shut your laptop, party until the next morning, and clock in at 9 am from your hotel room wearing nothing butt  your birthday suit.

Pro tip for working remotely: Be sure wherever you're traveling to has reliable internet and stay aware of what time you'll be expected to work if there's a time zone difference between your main office and travel location.

number 4 icon on orange construction paper with drop shadow | fckitybye.com | by Ryan Somohano

Save and Quit

No, this isn’t a tutorial on closing word documents. I mean saving money for a little while and then quitting your job.

"This solution is too heavy! Go back to talking about working on a beach and making butt puns like you did a few sentences ago."

Sorry dude, I'm limited to one butt pun per article.

Quitting your job isn’t for everybody and you need to seriously consider if it’s worth it to you. But if you work for a company that's completely inflexible with your work/life balance, then you have to decide between living with them micromanaging your aspirations or you leaving.

Unless you’ve already been thinking about leaving your job for other reasons, I recommend trying to work something out with your manager before resorting to this  how to work and travel ultimatum.

If after trying everything this solution is all you're left with - I totally get it.

I’ve seen people with jobs where "two weeks vacation" means a day or two every couple of months, never two weeks consecutively. I've seen places where if a senior employee requests vacation time after you during the same period, you have to drop your vacation to cover them. I've seen places where you're made to feel horrible for stepping away from your desk for any amount of time to do something you enjoy.

There are a lot of places that just don't get that you have an identity outside of your work. If that sounds like where you're at now and you can afford it, my advice is that life is short and you shouldn’t let a job keep you from your dreams.

And don't get discouraged if you can’t afford it. That’s where the “save” in this "save and quit" solution comes into play (read this great article to put yourself in a saving mindset).

Fun fact about me, I've personally exercised the save and quit  option before. I didn’t do it because I couldn't negotiate extra time off. I did it because, after two years of giving my team everything I had, I wasn’t passionate about what I was doing anymore.

I don’t regret it.

Fall sunset in Portland, Oregon on a hike near the japanes gardens in Washington Park | fckitybye.com | Photo by Ryan Somohano
One of the things leaving my job allowed me to do was take a break from Los Angeles and experience my first real Fall in the Northwest... oh, and it also allowed me to build this travel blog;P

Wrapping Up How to Work and Travel: The Ultimate Guide to Traveling with a Full-time Job

If you take one thing from this ultimate guide on how to work and travel, let it be that honest, open communication with your manager will almost always bring you to a solution you can live with when it comes to balancing full-time work with your travel ambitions.

Your manager as a business person should want to do everything they can to not lose a good team member. Your manager as a person-person should want you to be fulfilled in your personal life. Don't be afraid to give them the information they need to be able to achieve those ends.


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