From Side Hustle to Passport Stamps: How Freelancing is Taking Me to Thailand

When I dropped out of college, I didn’t have a plan mapped out at all. What I did know was this: I wanted to figure out a way to make money from my laptop so I could see more of the world. Not someday, not in ten years when I had “enough” saved up, but now.

Fast forward to today, and this October I’m taking my very first international trip—outside of a cruise—to Thailand. Ten whole days exploring temples, beaches, and night markets. And here’s the part that feels surreal: I’m able to take this trip because of the side gigs and hustles I’ve pieced together over the last year.

I’m not raking in six figures. I’m not one of those Instagram-famous digital nomads with brand sponsorships and unlimited flights. Honestly? I’m just making enough to support my lifestyle and carve out the freedom I wanted. And for me, that’s the dream.

Why Freelancing and Travel Work So Well Together

When I first started freelancing, I wasn’t thinking “this is going to fund a trip to Thailand.” I just wanted flexibility. I wanted to be able to set my own schedule, to work from anywhere with Wi-Fi, and to build something that felt like mine.

The more I leaned into freelancing, the more I realized how naturally it fits with travel:

• You really can work from anywhere—whether that’s your living room, a coffee shop, or a beachside Airbnb.

• You get to choose which clients and projects you take on.

• A handful of smaller gigs can add up and give you a safety net.

• Freelancing (like traveling) constantly pushes you out of your comfort zone.

I think that’s why I love the connection between freelancing and travel. They’re both about building a life that doesn’t have to look like everyone else’s.

My Side Hustles

The backbone of my freelancing right now is writing. Blog posts, articles, web copy—if it involves words, I’ve probably dabbled in it. Writing has been the main skill I’ve leaned on to bring in steady income.

But freelancing, at least for me, isn’t just one big job. It’s a patchwork quilt of side gigs:

• Freelance Writing → My main source of income.

• Admin + Assistant Work → A few light tasks for small business owners who need extra help.

• Other Odd Projects → I’ve said yes to random gigs here and there when they fit. Ans honestly, not all of them have been on my laptop. I've scrubbed a lot of toilets and walked a lot of pups for some cash.

  
  

None of these gigs by themselves would feel “huge.” But together, they’ve given me enough stability to pay my bills, enjoy some flexibility, and now—finally—take my first international adventure.

When I think about it in travel terms, it’s even more motivating. A $100 blog post? That’s a week of meals in Thailand. A $200 admin project? That covers a flight between Bangkok and Phuket plus a night in a hotel. Framing gigs this way makes it feel so real—like each piece of work is a step closer to my next stamp in my passport.

Where I Found Work

The question I get most often is: Where do you actually find these side gigs?

The truth is, it’s been a mix.

• Freelance Platforms: I started on sites like Upwork and Fiverr. Yes, competition is tough, but landing even one client builds confidence (and your portfolio).

• Networking: Once I got a few clients, referrals started happening naturally. Sometimes friends of friends, sometimes people who read my posts online.

• Putting Myself Out There: Honestly, just talking about what I do has opened doors. A simple “I do freelance writing” has led to opportunities I never expected.

And here’s a lesson I learned quickly: you don’t need 20 clients at once. A handful of steady, reliable ones can make all the difference.

Balancing Work and Travel

I’d be lying if I said freelancing while traveling is easy. There’s a lot to juggle—deadlines, spotty Wi-Fi, and the temptation to just skip work and go explore.

But here’s how I’m planning to balance it during my Thailand trip:

• Work Ahead: I’m batching a lot of assignments before I go, so I can truly enjoy time off.

• Set Expectations: Letting clients know early that I’ll be “out of office” for ten days helps everyone.

• Pack Smart: My laptop, a travel adapter, and a good pair of noise-canceling headphones are non-negotiable.

• Stay Flexible: If something urgent pops up, I can always carve out a few hours in a café.

The beauty of freelancing is that I can take this time off. I don’t have to ask a boss for permission. I just organize my projects, plan ahead, and make it happen.

The Bigger Picture

This trip to Thailand isn’t just about the destination. For me, it’s proof that leaving college to chase this laptop lifestyle was worth it. It’s proof that the late nights writing, the early mornings doing admin work, and the uncertainty of piecing it all together can actually pay off—literally.

I may not be making “tons of money,” but I am building something sustainable. Something that allows me to live, explore, and keep moving toward the life I want. And that feels richer than any paycheck I could have gotten in a job I didn’t love.

A Note for Anyone Dreaming About This

If you’re reading this and wondering if freelancing could work for you, here’s what I’ll say: start small. Take whatever skill you already have—writing, designing, organizing, teaching—and see if someone will pay you for it. Land one gig. Then another. Before long, those little wins stack up.

I’m not here to sell the idea that freelancing is glamorous or easy. It’s not. But it is freeing. It’s empowering. And it can be the bridge between your everyday life and the adventures you’ve been dreaming of.

This trip to Thailand is my first big milestone. I know it won’t be my last. And if I can build this patchwork life of side hustles to make it happen, I promise you can too.