I've worked at more than ten companies over my lifetime — including part-time jobs — yet I have no skills or experience that would seem useful for remote work. Hello Work told me plainly that someone of my age, without specialist qualifications, would find it very difficult to earn a stable income working from home. Even so, a combination of painful workplace experiences and the encouragement of the Libre Arts University community pushed me to try something I'd been curious about for years: overseas remote work.

Discovering the AI trainer role

After watching several YouTube videos on overseas remote work and researching through LibreCity's knowledge library, I came across an idea that genuinely surprised me: there are jobs for which simply being a native Japanese speaker makes you a sought-after candidate.

These are AI trainer roles. Tools like Copilot, ChatGPT, Gemini, Claude, and Perplexity AI all need to be optimised for different languages and cultures — and the people who help with that process are called AI trainers or annotators. No advanced English required; native Japanese fluency is the key qualification. I thought: if a job like this really exists, I have to try it.

The YouTube channel that helped me most was run by someone born the same year as my son — and with a name that sounded identical to his (though written with different characters, I'm sure). I took it as a sign.

Creating an English CV with AI

Overseas platforms require an English-language CV. I gave ChatGPT my Japanese résumé and work history, explained that I was applying for AI annotation roles, and it produced a complete English CV at remarkable speed — tailored to highlight what would appeal to that kind of employer. I also added a photo (recommended for building trust) using a free online tool, with ChatGPT guiding me through the steps when I got stuck.

Registering with overseas platforms

I signed up for LinkedIn, APPEN, OneForma, Upwork, DataAnnotation, Outlier, TELUS, and more. The process required uploading identity documents — my driving licence, my My Number card — which felt uncomfortable. I'll admit I had a moment of anxiety after it was all done, wondering whether I'd been too reckless.

With the time difference between Japan and the platform support teams, any document upload issue meant waiting overnight for a response. It took patience, but each registration confirmation email that arrived felt like a small victory. I read every email carefully with the help of Gmail's translation feature and DeepL, and worked my way through to actually applying for projects.

One note of caution: LinkedIn job listings can include fraudulent postings. The videos and LibreCity articles I'd read warned about this, and it's worth checking carefully before applying.

Getting started — and the endless trouble

From registering on the platforms to actually starting work took nearly a month: applying for a project, passing a test, completing a short training, installing the required tools. And once I started, the troubles began in earnest — tools that wouldn't work as the manual described, login issues, error messages. Every problem meant contacting support and waiting days for a reply. For the first project I chose, Japanese-language skills alone weren't sufficient, which added another layer of difficulty.

Navigating unemployment benefits

In Japan, you can receive unemployment benefits while doing limited work — roughly under four hours a day, three days a week — without a reduction in your payment. The project I chose allowed a maximum of one hour of work per day, so I felt confident I was within the rules.

At my first certification appointment in early April, I reported my work honestly. I was told to declare even the time spent checking emails — and as a result, despite only actively working for about three days, my benefit entitlement was reduced from 28 days to 19.

It wasn't a full reduction, just a shift in the payment schedule — but combined with the need to complete two job-seeking activities between each certification, I decided to pause my overseas work until I'd finished receiving my unemployment benefits.

At my May appointment, I reported no working days at all — and still only received 24 days' worth. It seemed the staff had never processed a case involving overseas remote work before; there was a hushed discussion and a long wait. I hadn't done anything wrong, but it felt uncomfortable all the same.

The first payment

After all of that — on 15th May, ¥10,848 arrived in my Rakuten Bank account. That's 71.68 US dollars after exchange fees and deductions.

It's not a large amount. But earning my first dollars felt like something genuinely significant — a proof that it's possible. I'll need to retake the project test to resume work, but I intend to. This small first payment has given me real hope.