The Greatest Challenges I’ve Faced While Traveling Alone

Last Updated on October 7, 2023

There aren’t many experiences I can think of that assist in the process of growing up more than leaving home on your own free will to travel the world alone. With or without anyone else, the world remains a huge place and the process of navigating it teaches you skills and lessons that I’d say are quite a bit difficult to obtain through other means. I do think solo travel is something everyone should strive to experience.

After leaving the USA in July of 2018 to travel abroad, I began one of the most difficult challenges I have ever tackled in my life. This trip, which began with 4 weeks in Greece, would mark my first time ever experiencing long-term backpacking, traveling all by myself, and eventually, rekindling a romantic relationship that carries on to this day.

It Begins with a Decision

Living abroad all on my own has been both the most rewarding and the most difficult thing I’ve ever done in my life. After graduating from university, I had a big decision to make: the decision of what to do next. Initially, I went on to gain some work experience developing a skilled background in insurance, finance, investing, and business before deciding to leave everything behind to tackle what would soon become the scariest challenge I’ve faced in my life: traveling and living abroad all by myself.

Nothing in the world could have prepared me better for the series of events that would soon follow. I would have to learn to support myself financially, emotionally, socially, and in every other way that adults do. Time to spread my wings and fly.

An Introvert… Traveling Alone?

The Challenges of Solo Travel

I wasn’t afraid of being of my own. While I do consider myself a people-person, I’m also a proud introvert. When people first meet me, they are sometimes surprised to learn that fact about myself. I guess it’s because, under normal circumstances, I’m not shy.

Being an “introvert” has less to do with how comfortable you are around people (shyness) and far more to do with where you draw your energy from. For that reason, traveling alone has been one of the most refreshing things I’ve done in ages; especially after graduating college and leaving behind my work in the financial industry where every aspect of being successful involved surrounding myself around people. I didn’t dislike it – in fact, I loved it. I thrive in great company and treasure my relationships with friends and family above all else, but that may also be why I need time alone at the end of each day.

Some time away from everything does the soul good. And that it did. While traveling so far, I’ve met amazing, unforgettable people. What a time to be alive.

“You’re never really alone when you travel alone.”

A half-truth. I agree that there are endless opportunities to meet new people while traveling. Like at home, you can find really fascinating people abroad. The friendships you make will broaden your horizons and help you form a fuller picture of the world.

A Sense of Stability… Living Nomadically

Despite constantly meeting new people, you may find that the lack of stability and dependability can wear you down. As an introvert, I found myself really susceptible to that specific aspect of traveling alone.

Long-term travel has a special way of magnifying everything that you experience. As much fun as I was having meeting new people all the time, nothing ever stopped me from missing Jorge and my family and friends from back at home at any point. I suppose it is just in my nature to be that way. I can’t help but feel a pang of sadness every time I think about the tradeoff that I make when I’m living internationally because I know it also means isolating myself from the people whom I love and want to be around.

In part, homesickness led me to take a pit-stop back in the USA around Thanksgiving of last year to be with my family and friends again. I think it is really important to do that. During that stretch of time, my Spanish boyfriend and I coordinated some plans for the upcoming year to spend an “extended” time living in closer proximity to one another. That’s what brought me to where I’m living right now: here in Spain!

Current Location: Madrid, Spain

Spending time with this one!

My boyfriend

Having already been in a long-distance relationship with Jorge since 2015, I’ve grown accustomed to the feeling of being geographically far away from the very people I want to keep in close contact with. I think that experience helped me mentally prepare for the social shift that comes along with living in another country. Nothing really prepares you, but that helped.

We All Have Our Own Paths

Perhaps one of the most bittersweet parts of nomadically moving around is that you have say goodbye just as often as you meet those same incredible people. I’ve never been good at goodbyes. I get really emotional at the very thought of parting ways from people who I am fond of.

Even in hindsight, I remain sensitive to the very thought of goodbyes from the past. As I tried writing this post, memories came rushing back from all the good times I enjoyed along the journey thus far and I had to stop several times to process everything going through my head. Maybe it is because the memories are still recent and vivid but I can’t help but feel like I’ve left a part of my heart behind in each of the cities I’ve had the pleasure of visiting. The impact that the people whom I’ve met along the way have had on me is greater in scope than any of them will ever understand.

The World Is More Connected Than You May Realize

Where Do You Really Belong?

The more I travel, the more I realize that “home” is less about having a specific spot on the map to throw a label on and more about recognizing where you feel the most happiness and love. Despite the way travelers sometimes feel, no one ever said you have to limit yourself to only having one place to call home. At no point have I ever questioned my sense of belonging to my family and friends back in the United States. Still, as I spend more time in Spain and these other countries that I’m exploring, I fall in love with them more and more. We’re less different than you’d think. I somehow feel connected to each of them, even the ones I clearly don’t “belong to.”

Traveling Alone in the Digital Age

The internet has been immensely helpful to me with keeping in touch with my relatives, close friends, and even acquaintances. I am really grateful to social media for that reason. I have Jorge to keep me company but I would never want to lose ties with any of my friends or family from back at home. Technology is great for that reason; it helps. Our digital lives are so apparent that sometimes I have to purposefully take a step back from my work to do things offline just for a break from all the gadgets. I think this is a challenge that a lot of travel bloggers and digital nomads face. I’ve been making a conscious effort to try to live more in the moment and to be 100% present in my daily life as often as possible.

Finding a Routine While Living Abroad

Finally, I’m still adjusting to this whole new life in Spain and I am trying to develop a balanced routine that grants me enough time to work, study, take care of myself, and still find time to pursue to my hobbies and passions. I have a ton of crazy stories from my previous destinations that I can’t wait to share with all of you. I’m determined to share them all with you guys.

I’m going to find the time to write everything down while still making the most out of each new day that I have the gift of spending in these incredible countries. I appreciate your patience and understanding in case the order of my posts appears a little wacky for this reason. It would be a pity to omit some of the stories about things that happened just for the sake of keeping everything perfectly chronological. Hope you don’t mind! Looking forward to sharing more of my backpacking and long-term travel memories with you! 🙂

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  1. so good to hear from you, Rocky. You sound happy, which is wonderful. Kudos for going your own way. I imagine it can get a bit lonely, but your thought process makes so much sense. Home is a word not a place. Looking forward to the stories of your adventures! Take care.

    1. The Rocky Safari

      So good to hear from you too! Thanks so much for following along, it really means a lot to me!! ☺️ I’m definitely really happy now. How are you?? I hope you’ve been doing well too!

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The Rocky Safari