Turning Life Upside Down for the Love of Travel

May, 2015 – Birmingham, Alabama

You wanted this, right? I’ll admit I’ve asked myself that question more than a few times as we prepare for this journey, trying our damnedest to keep the train on the rails.

For those new to this blog (thank you for following!,) here’s a quick overview of what’s happening:

My husband Matt and I have been dreaming for many years of one day taking off to travel the world for a year or more. Underneath the surface, expansive, slow travel.

After much plotting and planning, that day is fast approaching – we depart May 10 – and every minute in the run up is a scramble to make it happen.

We’re both in our 40s, have recently left high-level jobs (as many have said, at the peak of our careers,) own two homes, are close to our families, and fortunate to have a large network of life-long friends. In other words, we have deep roots and many reasons not to pick up and leave.

But, here’s the thing: we have to. We just can’t shake this need to get out of our comfort zone and experience the world.

Three days from now, we will begin the journey by moving over 5,000 miles away to the smallest town either of us has ever lived to date, Vattaro in the Trentino region of Italy. The population is roughly 1,000, but when you add in horses, cows, goats, crowing roosters, a few surly dogs, and a herd of cats…let’s just say, there’s a lot of life in this tiny place. We will spend two months here while Matt prepares for the Maratona dles Dolomites. I’ll be writing (for work and pleasure,) learning to cook pasta, making cheese, studying Italian, and running the hills. Once the bike race is finished, we plan to enter the “free flow” zone and travel where the wind – with the aid of the cheapest bus, train, ferry, or flight – takes us.

Every day it seems at least a dozen people ask how it’s possible to pull up stakes and chase a dream. The short answer is: it isn’t for the faint of heart.

I have benefited from writers who have shared their stories including Nomadic Matt and Hektic Travels, so in the same spirit of sharing with hopes the info helps someone else – if only to let you know you are not alone and/or encourage you to take the leap – here’s an overview of our process.


Making the Commitment
How do you leave your life behind to travel? Let’s face it: The time will never be right. There will never be enough money. Important things will always be developing within your family. Career gaps are always a risk. There will forever be a long list of reasons not to go. If you really want it…make a decision to go and run full speed ahead, stubbornly toward the goal.

Raiding the Piggy Bank
Let’s be clear, we’ve spent years prepping and saving for this opportunity. But, even with smart planning, it’s still daunting financially. In fact, if we thought too much about the money, we’d never make the leap. At the risk of being repetitive: there’s never enough money.

So, with that out of the way, let’s talk savings. “In ten years, we will quite our jobs and travel the world,” once that statement was said out loud, the goal was set, and saving became fairly easy. We both took on extra work, logging in more hours than ever. I even stayed in a crazy, dysfunctional work environment longer than I should have just to bring in more money. And, in maybe our smartest move financially, we began hosting travelers through Airbnb. Every bit of that rental income went into our travel fund. (Travelers funding travel, it’s a beautiful circle.)

Personally, I employed the “one less” strategy. Goodness knows, I love being out on the town and socializing and had no interest in cutting the “fun” out of my day-to-day existance, so I merely scaled back. One less lunch out. One less drink at happy hour. One less flirty skirt or gotta-have pair of shoes. One less trip to the drugstore (the money I could spend on cheap hair care products and makeup is truly embarrassing.) All the way around, having the simple little mantra of “one less” running on loop through the brain works wonders.

Not Ready to Sell, Yet Ready to Move On
For the past ten weeks, we have been guest room and apartment surfing in our hometown. Why? Because that’s what it took to reach the goal. We love our house and aren’t ready to sell, so renting was key to our traveling budget as well as peace of mind. We found the ideal renters, but they needed to move in before we could leave on the trip. I can’t lie: it hasn’t been easy living in our city, yet not in our home. We laugh about it almost every night as we drink wine in the living room of a friend’s (wonderful) apartment, feeling like we’re already on the road. And, if I’m honest, I think we needed this transition to toughen us up and get us ready for living out of a backpack again.

Pursuing Passions that Pay
As we all know, these days it’s possible to work from anywhere and we’ve been lucky enough in the past to travel extensively while still holding down full-time jobs. Now, because we want more of a life change, we’re going “whole hog” with me quitting my long time job and focusing on freelance writing and Matt selling his business to follow his passion for cycling and bike touring. We’re excited to see where our new career paths might lead. Stay tuned!

Staying Healthy
Through the end of the year, we have a (surprisingly) comprehensive plan through Blue Cross that covers us while traveling abroad up to 80%. After December, we will most likely go with a World Nomads travel policy possibly in conjunction with or in lieu of a U.S. health insurance policy. I’ll update this info as we go through the process.

If We Can’t Use It, Why Did You Sell It To Us? aka Getting There
In the first of what I’m sure will be many mistakes in this process, we fucked up when buying airline tickets. Apparently a one-way ticket to Europe is a no-go.

Unfortunately no one told us to be allowed to board the outgoing flight, you must show proof of a return ticket to the U.S. (not just proof of onward travel to say Croatia or India,) or the very airline who sold you the one way ticket won’t let you fly. It took a whopping three hours (of our lives we’ll never get back) on the phone with Delta (in addition to the hour fifteen for the original one-way ticket booking) to get it cleared up and a round ticket confirmed without penalty. Good thing, time is cheap these days.

We may use the return flight in three months as an opportunity to pop back in the US, visit with family and friends, then go back out on a Round the World ticket. Or we may just burn the tickets and keep on moving.

This is the annoying stuff that takes forever and a day to sort out.

Greetings From
This has to be the least sexy topic in the whole wide world. Unfortuantely, it’s important. What to do about mail? A P.O. Box isn’t the answer, who would check it?  You can forward mail. Problem is, we have no forwarding destination. Many travelers rely on forwarding to their parent’s home – but we’re in our 40s and that seems oddly like a fail. For now, we’re converting everything possible to online payment and correspondence and thanking our lucky stars that our renters – who are also friends – have agreed to sort through the clutter.

An equally sexy topic is cell phones. I just bought a dual SIM card BLU phone – so in theory, I’ll keep my U.S. number (mainly because I have a contract with AT&T through September) with a minimal text plan and get an international SIM card (with an Italian number) for calls and data. Two SIMs and two numbers on one phone…this shouldn’t be confusing at all. Matt’s AT&T contract has expired so he plans to get a T-Mobile international call and text plan for $50/month, no contract. And, my mom and I have spent the last few hours today testing video calls on Skype and ooVoo.

Letting Go of the Dream (Car)
I would have never guessed the most difficult thing for me to let go of is my car. It’s nonsensical. I am not a car person. Hell, I barely drive and I’m terrible at it. But, several years ago I bought my dream car (used): a convertible VW Beetle. I love putting the top down and driving around town. So now, do I sell it?

The easy answer is to sell both of our cars and not have the hassle or expense (update: Matt sold his today and as of Saturday will be happily car-free.) But what happens if we decide to stop traveling and come home nine months from now. Buy another car? That seems like a bigger hassle and more expensive endeavor. (Insert whining moment: Chasing a dream is hard.)  So, who knows, Saturday may find me driving the dream to CarMax and swapping it for freedom (or not.)

Saying Goodbye to Stuff
This has been my favorite part of the process so far. Getting rid of stuff has been (all caps, in bold, with neon) liberating. Taking bags of clothes and accessories to Goodwill, selling a few good items, and kicking tons of junk to the curb. Even if you aren’t leaving to travel the world, I highly recommend a grand purge. You’ll feel ten pounds lighter mentally.

Here are two great pieces of advice I received from friends:
1. When it comes to clothes, separate everything into categories: work, cocktail, party, outdoor, etc. Then pick 3-5 things in each category that make you feel GREAT, not good…downright smoking hot fabulous. Nothing else is worth taking up space.
2. When it comes to books (a big issue for me,) why not play curator and pair a book you love with a friend? For the past three months, every time I show up at someone’s house for dinner or meet for drinks, I bring a book I think my friend will like. It’s been more appreciated than I would have ever imagined and I love knowing good books have found a good home.

Gearing Up
I never thought I would love gear as much as I do. Every day, I fight the urge to buy the side-loading backpack I’ve coveted. I’m telling myself the backpack I have is just fine (stupid, hard to sort out top-loader that it is) and the money should be saved for a boat excursion, train ticket, or wine tasting – or maybe just for groceries.

I also have a perfectly good, fairly new laptop, but it’s big and heavy so I will take the plunge here and gear up with a new, lite, travel-friendly device. I am having a hard time deciding between a traditional laptop and a chromebook. Here’s what my uses are: writing and filing stories, uploading photos, social media posting, blogging, web surfing. Nothing more complicated. I am incredibly impatient and want a device that moves fast. That’s it. Suggestions?

The Last Time
We are milking this “leaving” thing for everything it’s worth and then some. When someone asks us to make plans with them, we’re all over it. After all, this may be the last time we see them for a while, right? We’re equally enthusiastic about food we’ll miss while traveling in the small towns of Italy. Thai food for the third night in a row? Hell yes! Mexican food for lunch and dinner? Right on.

Basically, saying “no” doesn’t seem to be in our rep at the moment. Write ten new articles, commit to a road trip to see the family, plan two parties, throw a yard sale, – all within a week. Yep, let’s squeeze it all in while we can!

More to Come
We’re enjoying every minute of this crazy process and hope you’ll enjoy living vicarioiusly through this project.

We truly hope our journey inspires our friends, family, and readers to chase a dream or two of your own. If you share our wanderlust, this list wasn’t meant to deter you in any way…just to show you it’s possible!


12 thoughts on “Turning Life Upside Down for the Love of Travel

  1. Fantastic article! I wish you both the best of everything in your travels, and wish I had half the energy, enthusiasm, and confidence that y’all have.

    Liked by 1 person

  2. Congrats on ALL of your stuff – both the acts of ‘letting go’ and the acts of ‘going’. I’m so proud of you guys and I know you will REPRESENT the ‘ham in grand style. Drink it all in!

    Liked by 1 person

  3. Excellent article. I enjoyed reading about what went right but also what did not. I wish you two the best on your adventure.


  4. Jessica,

    Hi, I met you at one of the 3rd Tues. My name is Nina. My husband, daughter and I had a similar outlook on life and decided to just pack a car and go to Merida, Mexico for 9 months. I have reflected on many of your experiences and same feelings. The adventure was one of the best things I did for myself and my husband thinks It was the highlight of his life. In 2 years we plan to go to Western Europe for 4-5 months. Since we will be nomads, staying no more than 3 weeks per country, I am hanging on to every word and experience you write. For example, just since we have been to Mexico, 2 years ago, technology like the phone, computer and digital photographs have advanced and I found your information on phone and “ooVoo” was new info to me (We use Skype). I love my Kindle Fire but it is so heavy, I will have to buy a lighter computer. I am curious to know what you purchase. Anyway, I just wanted to say, “I get it”. Many people just had a blank look on their face when we told them of our plans. Good luck and we will live vicariously through you until we go on our voyage. Nina


    1. Thanks Nina! I love hearing your story – and I also have big love for Merida. And, I can’t wait to follow your adventures in Western Europe. Thanks for the note!


  5. Last week I purged five garbage bags-worth of stuff, and it felt SO GOOD. Also, I’m still a big fan of your book idea and cherish the one you gave me at Christmas! Can’t wait to read about your adventures.

    Liked by 1 person

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