Obstacles Faced While Planning a Trip Around The World

When we started throwing around the idea of traveling the world for six months there were a lot of roadblocks preventing us from committing to the journey. Most of our hurdles are probably the same reasons that would prevent other people from taking that plunge as well—things like our house, the dog, bills, taxes, mail, cars, and of course, a lack of money.

With both of us supporting ourselves through freelance work, neither of us has steady income, and neither had saved up money for a trip like this. On top of that, I have a car lease that doesn’t end until February 2018, we have a dog that we love, a mortgage to pay, phone bills, taxes to file, and the list goes on. It was super overwhelming for us to start considering how we could possibly walk away from all these things, but a little pep talk from a good friend of ours, we were finally convinced that these roadblocks were just that—roadblocks. In the big scheme of things, none of them were a big deal, and they could all be figured out and overcome.

Power Couple | Darlene & Fat

We knew we wanted to take this opportunity to travel because we aren’t guarantee tomorrow. Plus, if we decided to wait six months or a year after we got married we’d probably find other excuses to add to our list as to why the trip wasn’t possible. Who knows, maybe by then we would have full-time jobs or a baby on the way. Now is the time, so we need to make it happen.

To begin the process of breaking down all the barriers in our way, first we wrote down everything that was stopping us. Second, we wrote down what had to be done in order to jump over each hurdle. Third, we organized the list into a timeline of when we would need to take action for each item, as some things were more immediate than others. And finally, we got to work!

Click here to download a copy our original list to see what it looked like when we started.
(It changed as we went along, but this is how it began.)

Now that we had our game plan in place, we needed to act on it. Neither of us is very patient by nature, and we were both really excited about the trip by this point, so we didn’t waste time in starting to check things off the list. What we learned was that with the list in place, nothing was overwhelming anymore and each thing seemed a lot less stressful.


What will we do with our cars?

This is personally the biggest stress for me. I’m locked into a lease contract until February 2018. I called to see what my options were to get out of the lease without having to pay a penalty or fine, and the options were essentially to find someone else to take over the lease, or to have someone buy the car from the leasing company. Sounds easy, right? Not hardly! The lease transfer process is a long one, and they don’t make it easy for you.

I washed the car, Fat took some photos of it, and we posted two listings on the Craigslist—one to take over the lease, and another to buy the car. Right away these seemed to be a great hit! Several people emailed and showed interest in both posts. However, there were two problems: First, the people that responded to the lease take over were afraid to move forward once they heard the phrase “credit check”. Second, the people that wanted to buy the car were offering close to $5,000 less than I need to pay off the car. After a month with no luck from Craigslist, I paid $300 to SwapLease.com to post my ad on their site. However, two days later someone from Craigslist contacted me and went through with the credit check process that everyone else was scared of. After the credit process, I found out that the person didn’t get approved. So I had to contact Swaplease.com and have them activate the post. At this point we are still sitting and waiting…

For Fat’s car that he owns outright, we looked into a monthly parking garage and found local options for around $50 a month. However, when doing research we heard things from other travelers that said they had troubles with their car after they left them for six months. So instead of paying $300 to have the car sit there, we decided he will sell it on Craigslist just before we leave. The car is old and needs some work anyway, so it really wouldn’t be worth hanging on to.


What are you doing with the dog?

The initial plan for Hercules, our 16lb Yorkie, was to have my mom take him to Buffalo, NY, after the wedding. Since she has a dog of her own Hercules would have someone to play with, so that made us happy. We planned to pick him up after we returned to the U.S. and take him back home with us. However, once we started trying to check off the action items under the “Dog” heading on our list, we realized there were a lot of small obstacles in the plan that added up to a lot of extra money and stress—finding out which airline allows dogs, the costs associated with flying a dog, figuring out the size of the carry-on crate, getting a check up at the vet, needing a travel release form, sleeping pills for the dog, figuring out the most convenient flights for the long trip, etc. In the end, we decided to figure out a “plan B” that would save us money, time, and hassle.

Our next plan was to find a foster home for Hercules that we trusted—and trusted to give him back to us when we got home, haha! We needed to find someone that would be happy to take care of him, so we posted our situation on our social media, and it wasn’t long before we found the perfect couple. Fat’s friend and girlfriend live couple blocks from us and already have a Yorkie mix puppy. They were planning to get another dog and thought this was a perfect trial to see what it was like to have two dogs. It was perfect! In the meantime the dogs have been enjoying puppy play dates and sleep overs, so they are pretty much best friends now!


What about your house?

Since we the condo, we decided to put it on the market for a six-months lease, fully furnished, and include the utilities. Leasing the condo this way accomplishes a few things—neither the future tenant nor we will have to go through the hassle of transferring the utilities back and forth, we can charge for more the rental, and it’s less that we have to move into storage. We did some research on how much we could charge per month, came up with a fair rate, cleaned the house, shot photos of it, and posted it on Craigslist and a few other sites in September. Darlene also posted the listing on her Facebook page, where we got a little traction. As I write this a friend of a friend who found the post on Facebook is flying down from Portland to check out the place and (hopefully) sign the lease agreement. Again, fingers crossed and we’ll keep you posted!


What are you doing with your belongings?

One of the fortunate things about our condo is that we have an 8ft x 10ft storage closet in our garage, so we will be able to keep our personal belongings locked in there while we’re gone instead of spending money to rent a storage unit. With that said, even though we don’t have THAT much stuff between the two of us, we still did what every other traveler has said to do and purged!

We decided that there was no need to keep certain things—it’s all just stuff, and if we need it later, we can buy it again. We scheduled a day to clean out our storage room, closets, drawers, entertainment center, etc. We set up a mini photo shoot for stuff we could sell on Craigslist—things like home gym equipment, camera gear, a bike, random electronics, backpacks, and luggage. We then posted it all on Craigslist. We have been slowly getting rid of things while brining in some extra money for the trip.

We also tried to sell some clothes and shoes to Buffalo Exchange, but it wasn’t a huge hit. The things Buffalo Exchange didn’t take we just donated to the Salvation Army. There were also a lot of things we simply threw away. The process of purging actually felt nice because it reminded us that these possessions are just stuff with no meaning. Having each other is more important than owning things.

Power Couple | Darlene & Fat


What about tax season?

Since we are both self-employed, filing taxes is more of a process than if we were employees so Fat contacted his accountant to discuss what to do. We thought it may be a big problem or hassle that we’d be out of the country during tax season, but the CPA simply told us that we’d file together since we’d be married by then, he’d file an extension, and then we’d have until October 2017 to finish filing. Easy! So the plan is to enjoy our trip, not worry about taxes, and take care of everything once we return.


What about the mail?

After juggling around a few ideas like getting a local P.O. Box and having a friend check our mail we decided will have our mail forwarded to Fat’s mom’s house in Louisiana. We will FaceTime her every so often to see if there is anything important we need to take care off.


The Next Steps

We’ve taken massive action, and the plan is in motion. We will also cancel our gym memberships as well as the Hulu and Netflix accounts to cut our monthly expenses, and Darlene will get rid of her phone, leaving us with only one phone bill on Fat’s plan that has unlimited international texting and data. If you want to learn more about how we are budgeting and funding our extended travel, check out the post that goes into detail about that.

Our pre-trip obstacles aren’t much different than what you may face if you were considering extended travel. If you really want to make it happen, you need to take a step back from the big picture, break it down into small, manageable pieces, figure out a game plan, and take action. Remember, if it’s something you want to do, you can always figure out a way to make it work!