Travel Tips

The rarely discussed realities of traveling with your 9-5 remote job

toes in the sand

You decided you wanted to travel for awhile and still have income, so you took to YouTube and the blogging world to figure out how to make this happen.  Everyone you watched or read suggested asking your boss if you could work remotely, so you bit the bullet and asked….and the answer was… YES!!  Smiling and excited beyond belief you skip back to your desk and start dreaming of the exotic places you could go while working remotely.  Before you get too far ahead of yourself planning, let me give you a few truths about traveling with your remote job that your favorite YouTuber or blogger might have missed.

Now before I go into this let me explain where my realities come from.  Both Drew and I work for companies in the insurance arena.  My job is completely remote, meaning I have never met my boss, I was hired remotely and my equipment was sent to me.  Drew worked in the office and asked to work remotely  and was finally able to starting in June so we know quite a bit about remote jobs.

Reality #1: Equipment

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While you are daydreaming about traveling at your desk take a good look at your equipment on your desk.  Do you have a desktop computer or a laptop?  Do you have a phone on your desk? A printer?  Everything currently on your desk will come home with you.  About 95% of companies will not issue you a laptop just to work remotely you get what you currently have.  Both Drew and I were issued desktop computers with two monitors….that right there makes flying anywhere hard…but you can still drive just plan for the computers to take up space.  And before you ask, yes we did request laptops, and the answer was NO.

Reality #2: Schedule


Still daydreaming about traveling?  Take a moment to think about your schedule.  What are you currently working (9-5 Eastern Time)? This is what you will still be working when you work remote.  Just because you work remotely does not mean you will get a chance to make your own schedule.  Even with my job being completely remote, I am required to work 8 hours straight and cannot change my schedule day to day.  However I was allowed to chose my 8 hours as long as they were between the business hours of the company.  Drew is allowed flex time, which means he can start work anytime between 6:30 and 8:30 in the morning and his schedule day to day can vary, still working 8 hours straight.  This is especially important to think about when you are planning on traveling with your job.  Typical check out times are between 11 and 2….are you going to take a half day? Sick time? Run up to Starbucks on lunch and work from there till quitting time?

Reality #3: Home Base

Now this reality covers a broad field, but I think home base is a good title.  If you are completely remote like I am you will be required to put your home address on file.  Now you can change your address, but you have to have one on file that you can be at in two days or less.  The reason for this is because the company will send you a new computer, computer parts or whatever you need to that address if something breaks and most likely it will be overnight or two day shipping.  Now on the flip side of that Drew’s company will send a support person to the house if his computer breaks so while traveling he either has to take sick days till he can get back home and then call the support department, or book it to beat the support person to the house.  In some cases, for the people that didn’t start out as a remote employee, your job might require you to go into the office if the computer system is down and support can’t get you back up and running.

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Reality #4: Internet

Now this one most people do not think about since everywhere has wifi these days right?  Not necessarily.  To connect to the VPN and use our claims processing system we are required to have a certain speed.  I am required to be hard wired, although I have used wifi in a pinch, just for the speed.  Why is this important?  Public wifi (think hotels, starbucks, etc) rarely make the cut for internet speed.  This limits where you can work from even more.  Now your company probably doesn’t use our systems, but make sure you ask about internet requirements before you leave the office for the last time so you don’t get a surprise later down the road.

Reality #5: Time

Think about how you feel when you leave work for the day.  Do you feel energized?  Probably not, it’s been a long day at work and going home to sit down and relax is high on your list of things to do.  People have the misconception that if you do the same job from somewhere else it’s magically not going to be as stressful.  This is important to realize because if you travel with your current job you are probably not going to see much during the week due to work being stressful and you being worn out and just wanting dinner and relaxation at night.


Please do not take this as me trying to dissuade you from asking your boss to work remotely and traveling with your current job.  The reason I decided to write this was because I had heard from almost every Youtuber and some bloggers that have done “how to work and travel” videos and posts, that asking your boss to work remotely was the same as all the other remote jobs (like blogging, designing online courses, writing ebooks, etc), and the truth is it’s not.  While traveling is still possible, as we have found out, it’s not as simple as grabbing your laptop and catching a flight like people have portrayed it, but although there are quite a few challenges, it’s still easier than traveling with your office based 9-5 job!

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