How to Find Time to Go on Extended Travel With Your Family

Winter vacation in Puerto Rico

Winter vacation in Puerto Rico

For most parents, finding the time away from work or businesses and syncing that up with their kids schedules is the hardest part of going all in for extended foreign travel. Most parents are stuck in jobs that are 9-5 with “slow” times around the holidays (i.e. July 4th and Christmas). Organizing a week or two of travel around these times would be the first logical step, since it’s socially acceptable to be away longer around this time of the year. Anything longer normally would be a “Do you still want this job?” conversation with your boss when you put in your PTO request.

Here’s the dilemma: You want to get away with your kids for as long as possible, but want to keep your job intact, and would certainly want to avoid the congestion and the high prices of travel around the holidays.

How can you solve this challenge? Let’s break this down by answering three separate questions:

1. How long do you want to go?
2. How will you negotiate that amount of time with your boss?
3. What is the best timing of the year to travel with your kids?

How long do you want to go?

With no limiting factors (time, money, etc.), how long do you want to spend locked up with your kids in a hotel room or one-bedroom apartment in a foreign land? If your tolerance level hasn’t been tested yet on the road, perhaps start with one week and then work your way towards longer trips.

For truly authentic and immersive experiences, I’ve found the sweet spot at 3 weeks per country. 2 weeks in Lima left me wanting more of the culture and the scenery of Peru. 5 weeks of steak-eating and wine-drinking binges while dodging dog poop all over the sidewalks of Buenos Aires, Argentina left me missing the comforts of home towards the tail end of the trip.

Most workers in the United States can swing at least 3 weeks of PTO per year. Add holidays, comp days, paternity/maternity leave, and sick days and the sky is the limit on how much time is available to take off. U.S. workers reported earning 14 vacation days in 2013 on average, but claimed only 10, according to Expedia’s 2013 Vacation Deprivation survey. In addition to that, Hotwire discovered that Americans leave an average of 12 paid accrued vacation days unused. According to these statistics, time for extended travel is available, but amazingly most Americans aren’t fully utilizing all of their opportunities.

Want to do business in Europe during the month of August? Not a chance. Everyone is OOO and you cannot do anything about it.

Want to get a reply from a manufacturer or agent in China in January? Don’t even think about it. The greatest annual human movement is occurring before the Lunar New Year Holiday.

In other countries around the world, it is socially acceptable to disappear from the face of the earth for a month at a time. In the USA, it’s all about making it socially acceptable for your situation. Set an amount of time you want to take off for your trip and negotiate that amount of time with your boss.

How will you negotiate that amount of time with your boss?

Now comes the scary part: Facing your boss and giving any indication that your job is not the most important thing in the world because you need to take three weeks off to take your family to go swimming off the beaches of Spain.

Most people cut themselves short and assume the worst case scenario. The internal monologue typically goes a little something like this:

If I take three weeks off, people will disregard my OOO message and go straight to my boss for answers. My boss will subsequently get extremely frustrated for not being online during my vacation within the first week of me being away and will start a job requisition with HR for my position, hopefully to have a new hire in my seat at my desk upon my return. Pink slip will be ready in hand from my boss as soon as I get back to my desk on my first day back from three weeks off.

Most of the working population of the USA has already talked themselves out of the negotiation with their boss before they’ve even had it. They put in 5 to 7 business days PTO request to keep it short and sweet, so their job status is unchanged upon their return. The end result is half the vacation time is spent traveling to and from the foreign country with little, if any, meaningful local experiences to be had during the trip with their kids.

Here was my conversation with my boss from a Fortune 50 company:

Me: “I have an event in India in October. From my experience of traveling there right before the show starts, I’m a complete zombie from jet lag and have not been able to function coherently when I get on the ground. Would it be possible to fly out a few weeks earlier to stay with family in Asia so I can get time adjusted and be on the same time zone as my Indian counterparts leading up to the event?”

Boss: “Sure. I don’t have a problem with that. I’ve worked in Hawaii for a week before. As long as you get your work done.”

Me: “Oh yes, I’ll be online on California time. From my experience, I won’t be sleeping on Asia hours until about a few weeks in, so I’ll be wide awake during the middle of the night in Asia.”

Boss: “Yes, that’s fine with me. I really don’t care where you work, as long as you get your work done.”

Me: “Great. Thanks for your flexibility and understanding.”

After that conversation, it was like the gates of heaven opened right before my eyes. The prospect of extended travel, while keeping my day job, was becoming more of a reality. With the green light from my boss for a remote foreign/on the other side of the world working agreement, I booked the flight to China, with a stopover in Hawaii for a week. I ended up being in China for almost a month before my India event.

Days were spent with my family and 1-year old daughter making the rounds with relatives and slowly drinking green longjing tea all day long over card games while looking out at the beautiful West Lake of Hangzhou.

Due to the time difference, I normally was able to answer any urgent emails for the day by replying in the early morning in China, which was the late afternoon in the USA. Most conference calls with colleagues in the States were scheduled for late night China time/early California time. I also was available online from the hours of 11pm to 8am China time every night. Obviously, this was not realistically feasible, but with the advances of technology and masked “availability,” how many instant messages and phone calls did I receive that were important and urgent during that one-month span? Zero, Nada, 零.

And what did I come back to after nearly 2-months “away” from the office? Exactly the same way I left it. Job still intact, but richer in travel experiences, nonetheless.

My example may be an extreme and fortunate one, but you can free yourself from the grip that your job has on you. If a remote working agreement is not in play, then start with a three-week PTO/holiday/comp day all-in-one request. If long vacations are frowned upon at your company, then you can position the request as any or all of the following:

1. A necessary recharge of the batteries that will make me a 3x better employee when I get back.
(Play the card that this is actually benefiting your boss by him/her granting your wish to cash-in the PTO you’ve earned.)
2. Something that has been in the works for years.
(Play the guilt card.)
or one that usually works…
3. A family obligation that I cannot get out of.
(Yes, you owe this experience to your kids and you are not lying to your boss.)

And if your boss continues to push back after all of those reasons, as a last resort, tell him/her that you’ll be available for any urgent and important “fires” that need your personal attention. Offer your personal email address as the conduit for these inquiries, as you will not be checking business email inbox during your trip. 9 times of out 10, your boss will not disturb you on your trip. Most of the times it’s just a heat check for them to make sure they feel secure with you being committed to the job.

Now that you’re free from the reigns of your 9-5 job and you’ve finally got liberty for at least 3 full weeks, syncing that up with your kids’ schedules is the next challenge.

What is the best timing of the year to travel with your kids? 

The months of July, August and December are the not the most ideal times to travel with kids. Not only will it put a bigger dent in your bank account, you’ll have to deal with the stress of full flights, long lines, and increase the chances of running into travelers who want to be Debbie Downer and ruin your travel experience abroad.

If your kids are not in school yet, then the world is your oyster. All you need to do is get the extended time off with your boss, as previously explained.

If your kids are in school, talk to their teacher(s) and see what is the longest allowable time they can be out of class without getting de-enrolled and negotiate for at least a week more on top of that. By positioning it as adding value to their classroom, as your child will come back more grounded and fresh with worldly experiences to share with fellow classmates, their teacher will welcome the possibility of having a local-born exchange student in their classroom.

Once you’ve got the green light to take your kids out of school for at least 2-3 weeks, the task is to figure out when’s the best time of the year to travel to the destination you’ve identified.

We traveled south of the equator to Buenos Aires in November and December and were in tank tops, shorts, and flip flops for our entire trip there, while all of my colleagues, friends, and their kids were bundled up in the Bay Area. Besides the cold, they had to deal with darker days that ended at 4:30pm due to the onset of Daylight Savings Time.

Find the sweet spot of what your destination’s best travel times are, when you can take off from work, and when your kids can be taken out of school. Once you’ve figured that out, get on Kayak.com, find the best airplane tickets, and book your trip so you cannot back out of setting sail for your adventure with your kids.
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Challenge: Mark 3 weeks on the calendar in 2014 as the time for your extended family vacation. Commit to making the preparations to take that family vacation by putting in your vacation request and booking your airplane tickets.

Cliff Hsia is a writer, husband, and father, who is determined to live a better than normal life by traveling the world, slowly and purposefully, with his wife and two young daughters. His writing has been featured on MSN, TODAY, The Huffington Post, The Good Men Project, and other publications. He writes about travel, parenting, and lifestyle design.

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