Thailand: My Very First Solo Trip -- Mistakes I made

Thailand is a special one for me on my top 10 list. As you can tell by the photos, this was a while back— back when I first discovered my love of being Abroad and way before I even thought about being A Bald.

Thailand was the first place I had ever solo traveled to, my first hostel experience, and the first time I fell prey to the classic tourist traps 😂 (but more on that later).

It’s crazy looking back at these photos and thinking about how much I’ve experienced, I’ve learned, and I’ve grown since then. I vividly remember how awkward and uncomfortable I felt walking into that hostel for the first time– So aware, shocked, but excited of the fact that the closest soul that wasn’t a total stranger to me was thousands and thousands of miles away from me.

I was alone.

…but not for long.

After a full night of literally zero sleep (thanks jetlag), I began meeting people and quickly learned that amazing, friendly people are everywhere. All it takes is a smile and a “Hello”, and that anxiety and loneliness instantly begins to vanish.

Since it was my very first solo trip, I made tons of mistakes and wasted a lot of money… I’ll share them so hopefully you can avoid making the same mistakes:

1 - Traveling too fast

I know, we all have limited time. But I took 8 flights in the span of the 10 days I was in Thailand...absolutely insane. I just tried to do too much. I would have been better off picking my top 2 locations and really enjoying them instead of sitting in airports and planes my whole trip.

2 - Preplan if you’re going to, or don’t. But pick one.

If you’re the type of traveler that likes to plan each day before you get there, go for it. I left my itinerary open to stay open to spontaneity (good idea), but what actually ended up happening is my discomfort with the uncertainty allowed me to be convinced to go to a travel company in Bangkok to help me plan the rest of my trip (bad idea). Mediocre hotels, half my rides didn’t show up, and I wasted multiple hours sitting in a not-so-nice travel agency office. I could go on…

3 - Spending an exorbitant amount of money on classic tourist traps

In this case, Thai suits. While touring around Bangkok after being awake for something like 36 hours, I let the tuk tuk driver take me to an upscale suit shop after a local at one of the temples raved about it 🙄. I figured I’d check it out and maybe take advantage of the conversion rate. After all, I did just start my first big boy job out of college, so maybe I could use a nice shirt or two.

I arrived at the shop, and the shopkeeper was so nice, charming, and welcoming. He poured me a local beer “on the house”, and combined with my already poor judgement from the lack of sleep… it was over for me.

Probably the easiest sale that dude had all year. And boy, did he take advantage of it. He upsold me left and right – throwing in “free” this, and “discounted” that.

I walked out of that shop substantially poorer… I’m too embarrassed to even remember how much I spent, but it was easily north of $1000– probably twice as much as the flight I bought to get there 🙃

The best part is that I had to rush the process because I was leaving Bangkok the next day. So my freshly tailored suits ended up fitting less-than perfectly when they did eventually arrive back in the US.

To their credit, their suits did seem very nice, and if I had time to go back to the shop for a final fitting, I’m sure they’d fit better, too. They also went above and beyond and brought the suits all the way to my hostel to try to fit them as best they could. (Imagine walking into your hostel room and some naïve American is trying on a bunch of suits 🤣)

Photo Gallery