Avoid These 5 Mistakes I Made on My First Solo Trip
Updated: Apr 27, 2019
I have exactly zero photos from my first solo trip, which was a week-long visit to a beach town in Portugal when I was 20.
Because I was embarrassed of how the trip went! I made a lot of mistakes, and it didn't go well. Sure; in the long run, I learned from my failures. They helped me build my foundation as a solo traveler. But at the time, I wanted to run from the experience. I didn't want to even face or admit the fact that my first solo trip was largely a failure, much less learn from it.
So we often hear that making mistakes is key for growth, and that's totally true. But here's why I don't want you to make these particular five:
Because together, they made me form a negative image of a city, of solo travel, and of my own capabilities. And that's a step I'd like you to just be able to skip. 🤷🏻♀️So if you want to avoid my pitfalls (which are common ones) to get YOUR first solo trip off to a better start, read on!
1. I felt sorry for myself. My first solo trip was unplanned. I'd been traveling with friends in Europe after studying abroad, and they had other plans with family for our final week of the trip. I had seven days to fill, so I decided to get the cheapest ticket I could find to any beach. I ended up in Portugal.
Taking this trip solo was a last-minute decision and a last resort—something I only did because I had no other options. So before I even arrived, I already felt sorry for myself. Instead of seeing it as an opportunity to design a trip exactly to my specifications and preferences, I turned it into a burden. I fell into the trap of society's false logic that says it's unnatural to be alone, that you must always be half of a pair or a member of a group.
And once I arrived, my trip didn't immediately turn into a giant party where I was surrounded by cool, interesting new friends and flowing champagne. So I felt even more sorry for myself. The only giant party I had was a pity party for one. 😑 Instead of taking advantage of the awesome privilege I had to explore a new place on my own schedule, I wallowed.
What to do instead: Appreciate the opportunity. Traveling is a luxury, as is traveling alone. Take joy in embracing a new challenge, and remember that every mistake or difficult situation is a learning opportunity that'll make you a stronger traveler.
2. I arrived at night. Because the flight that got in at 2am was cheaper. Nowadays, my advice is to never put money before your safety or peace of mind, but I didn't know that then. It was hard to find a taxi, and once I did, I was terrified every minute of the ride. I was hyper-aware of being alone with a male driver I couldn't communicate with as he whisked me away into the unfamiliar night. So I started my trip with these feelings of fear, and they carried through for the entire week.
Plus, things never seem to look quite as positive at night as they do in the light of day. There's a quote I like from The Bean Trees by Barbara Kingsolver, and it's a Southern expression a character's mother likes to tell her: Even a spotted pig looks black at night. 🐷🌙 Your brain can play tricks on you at night, making things seem worse than they are. So not only is it safer and logistically easier to arrive during the day, but it also can set an entirely different, more positive tone for your trip.
"Even a spotted pig looks black at night." -The Bean Trees
What to do instead: Simple. Arrive during the day whenever possible! It's safer, easier, and gets your trip off to a better start.
3. I chose the wrong accommodation. If you think that where you stay as a solo traveler doesn't matter, that all you'll be doing is sleeping there, flip that mindset around right now! Where you stay is another factor that can set the tone for your whole trip—for better or for worse.
In my case, I pretty much picked the first hostel that popped up. After I checked in, I was led to my private room...across the street and around the corner. 🤨 It was in a separate building from reception, a strange setup I still haven't seen since then. I soon discover there is no. one. else. staying in this entire "hostel," so I'm hyper-aware of being completely alone in this huge, old building. I was scared the whole time.
So not only was I not able to meet people at my accommodation (there were none), but the fear and paranoia I felt at being so alone put a dark cloud over my stay. I was scared to go out, and I was scared to go back. There was nowhere I felt truly safe or calm, and that obviously had a negative effect on my attitude towards the trip and towards traveling alone.
What to do instead: Look at reviews carefully before booking. If you're staying in a hostel (which I highly recommend for your first solo trip), choose one with a common area, dorm-style rooms, and high ratings for a social atmosphere.
4. I was too quick to judge. I have a now-comical line I wrote in a travel journal at that time that illustrates this: I hope these days go by fast. I thought I was more self sufficient than I am. I’m not at all, I need people. I can’t even last one day here without feeling oppressively lonely and lame. So good luck to me.
Guess when I wrote that? 👀 Less than 24 hours into my week-long trip. I put a big "NOPE" stamp over solo travel in my mind just a few hours into my first experience. My (severely limiting) mindset was: You're either cut out for something, or you're not, and you'll know right away. Clearly I'm not cut out for solo travel, or I'd be having the time of my life right already. As a shy, reserved person, I didn't expect to enjoy the trip, and I turned out to be right. Self-fulfilling prophecy.
Although that line from my journal makes me laugh now, it also makes me SO sad. Because I know this way of thinking is really common. As a result, so many of us miss out on things that could turn out to be our most fulfilling experiences—even our lifelong passions. But we're not giving them (or ourselves) a chance.
What to do instead: Be gentle with yourself and patient with the experience. View it as a challenge and a learning opportunity instead of a quick test that will decide, for the rest of your life, whether you're cut out for this activity.
5. I was ashamed of failing. After I made my (premature) proclamation that I'm NOT the right person for a solo trip, feelings of shame and guilt set in. You can imagine that those were also big blockers to my enjoyment of the rest of the trip.
I was embarrassed because I felt like I overshot, I got in way over my head. Like a kid who thinks she can play in the big leagues and ends up getting trampled. I also felt guilty for basically wasting a trip that many people would jump at the chance to take. So, like my unpleasant hostel, these feelings were a factor in creating the dark cloud that I had over my head the entire week. I didn't explore, I didn't try to start conversation with anyone. I didn't even try any restaurants! I felt so bad that I lived on bread and cheese from the grocery store, eaten alone in my room, the whole time. 🤦🏻♀️
What to do instead: Again, be patient with yourself. Recognize that solo travel is a big undertaking, a challenge. As with any challenge, things likely won't click perfectly right away. Don't let fear or frustration get in the way of truly giving this experience a real chance.
Here's the thing: You'll make mistakes when you travel alone. You'll make mistakes in most every aspect of life, because that's what humans do. But now at least you can avoid these five solo-travel mistakes that I made! They formed a negative combination that almost made me give up solo travel forever—when now, it's become a huge, important, and highly impactful part of my life.
Happy mistake-making, and happy travels!