How to Actually Start Working Remotely (From Someone Who’s Done It for 10 Years)

So you want to ditch the office and start working remotely? Trust me, I get it. I’ve been getting this question non-stop, especially since remote work and digital nomad visas have become such hot topics.

Here’s the thing though—when I made the jump back in 2015, it wasn’t all sunshine and laptop-on-the-beach vibes. I took a massive pay cut and basically had to rebuild my entire career from scratch. But ten years later? Honestly, it was one of the best decisions I ever made.

If you’re serious about making this happen, let me walk you through exactly how to get started—the real, unfiltered version.

My Journey (Because I Want You to Know It Wasn’t Easy)

Back in 2015, I left my corporate job to travel through South America. Yeah, I was one of those people who quit to travel the world. Remote work was basically my ticket to sustaining that lifestyle.

But here’s what nobody tells you: remote work is a completely different ballgame from corporate. Not everything I learned in my previous job applied, so I literally had to start over.

My first remote job? About $500/month for part-time work. Yep, that’s the reality check right there.

And coming from the East while working with Western companies meant I had to unlearn and relearn so much just to adapt to how things are done. It was frustrating as hell, but absolutely necessary.

So if you’re feeling overwhelmed right now, just know you’re not alone. Everyone who’s made this transition has been exactly where you are.

Where to Actually Find Remote Work

When I started out, I tried a bunch of platforms: Onlinejobs.ph, Upwork, and Freeeup.

Onlinejobs.ph got me most of my early jobs, but I eventually had to step away. The platform was advertising cheap labor from the Philippines to businesses abroad, which created this whole situation where startups would lowball Filipino workers even when the work was exceptional. I experienced that geographical discrimination firsthand.

That said, if you’re just starting and have no idea where to begin, it’s unfortunately still one of the more accessible platforms. Full disclaimer: I haven’t used it in seven years, so I can’t speak to what it’s like now.

Upwork was super competitive back in 2015, and I’m sure it’s even more crowded now. But hey, you’ve got nothing to lose by trying.

Freeeup got me a couple of project-based gigs, which was helpful early on. Not sure how active it is these days, but again—worth creating an account.

Start With What You Already Know

Here’s my best advice if you’re feeling overwhelmed: start with skills you already have.

Good at accounting? Look for bookkeeping jobs. Know marketing? Try social media management. Don’t overthink it—just use what you’ve got.

The important thing is to get started and gain experience. You can experiment and improve your skills as you go.

And here’s something that helped me a lot: you may not always know what you want, but at least figure out what you don’t want. Use deductive reasoning when job hunting—it’s way easier to filter out jobs you hate than to magically know your perfect role right away.

My Pivot Story

I started with digital marketing and social media marketing because my corporate background was brand management. Turns out? I didn’t like it.

I also hated customer service, so I pivoted and taught myself to build websites using WordPress and Shopify. This was actually super helpful because now I can build sites for my own businesses instead of hiring someone.

I enjoyed website building, but dealing with clients who wanted endless revisions? That became exhausting real quick. The back-and-forth was never-ending, so I had to pivot again.

Then I transitioned to ecommerce, which turned out to be a really good move—especially when COVID hit. I was lucky to have a manager who provided learning materials about selling on Amazon.

That was eight years ago, and I’ve been in ecommerce ever since. But here’s the thing: ecommerce is constantly evolving, so I’m always learning about new marketplaces, TikTok Shop, live selling, and whatever comes next.

This is the importance of continuous learning if you want to keep working remotely.

Build Your Leverage

You need to create your own leverage so that:

• Companies come to YOU
• Companies pay the rate that YOU want
• Companies view you as an expert, not just another virtual assistant

You need to keep showing up, getting things done with minimal supervision, and over-delivering. Always.

Once you have leverage and experience, platforms like LinkedIn become game-changers. I’ve been using LinkedIn for seven years whenever I need a new remote job. Even when I’m not actively looking, companies reach out asking if I’m open to opportunities.

That said, I’m not telling you to avoid LinkedIn until you’re experienced. You can absolutely start applying to remote jobs there right now.

The point is: use whatever tools and platforms are available to you. You’ve got to be aggressive (in a good way) and put yourself out there. Keep trying, keep pushing, keep going.

The Real Talk

Starting over will test your patience and resilience. There’s no way around it.

For me, it was worth it because my love for travel is way greater than my love for a corporate job. Climbing the corporate ladder never interested me, so I made the leap.

Ten years later? Best decision of my life. If I had to do it all over again, I would—no questions asked.

You Can Do This

If you’re thinking about making this transition, I want you to know that it is possible. It won’t be easy, but it’s absolutely possible.

The key is to start somewhere, gain experience, experiment with different roles, and continuously level up your skills. That’s how you build a sustainable remote career.

So what are you waiting for? Your remote work journey starts now.

Have questions about starting your remote work journey? Send me an email—I’d love to hear from you!