The Problem Isn’t Effort, It’s the System

Filing taxes in Japan isn’t hard because people don’t try.

It’s hard because the system was never designed for individuals navigating it on their own, especially freelancers, first-time filers, and foreign residents.

Every year, the same story repeats:

• Confusing forms filled with unfamiliar terms
• Instructions that assume prior knowledge
• Fear of making a mistake and being penalized later

Most people aren’t trying to avoid taxes. They’re trying to do the right thing, without accidentally doing the wrong one.

Who Struggles the Most

Some groups feel this pain more sharply than others:

• Freelancers and sole proprietors
• Foreign residents dealing with language barriers
• Side-hustlers filing taxes for the first time
• Employees with complex deductions

For them, tax season isn’t just paperwork. It’s weeks of uncertainty and second-guessing.

Why Existing Solutions Fall Short

There are ways to get help, but none are ideal.

• Accountants are reliable, but expensive and hard to scale
• Tax software often assumes you already understand the system
• Government documentation is accurate, but rarely approachable

Each option solves part of the problem, but none solve it end-to-end for everyday people.

The Hidden Cost of Getting It Wrong

The real cost of tax confusion isn’t just financial.

It’s:

• Hours spent searching forums for reassurance
• Stress about missing deductions
• Anxiety over compliance and audits
• Delaying important financial decisions

Taxes quietly become a mental burden, something people dread instead of understand.

Why We Started HelpMyTaxes.jp

HelpMyTaxes.jp started with a simple idea:

What if tax filing felt more like a guided conversation than a legal exam?

The goal isn’t to replace accountants or give legal advice.

It’s to:

• Break complex steps into plain language
• Ask the right questions at the right time
• Reduce uncertainty, not add to it

In short, help people move forward with confidence.

Trust Is Not Optional

Tax data isn’t just numbers.

It includes:

• Income and employment history
• Family and residency information
• Financial behavior over time

If people are going to trust a product with that data, trust can’t be an afterthought.

Privacy, security, and transparency have to be built in from day one, not bolted on later.

What This Blog Will Cover

This blog is a place to document what we’re learning while building HelpMyTaxes.jp.

That includes:

• Product decisions and tradeoffs
• Technical challenges behind the scenes
• Mistakes, dead ends, and course corrections
• How we think about cost, privacy, and scale

No hype. No buzzwords. Just real problems and real solutions.

What’s Next

In the next post, I’ll share why building a product like this eventually led us to rethink how we use AI, and why relying entirely on proprietary models wasn’t the right long-term choice.

If you’ve ever felt lost during tax season, you’re exactly who this product, and this blog, is for.

Thanks for reading. The journey starts here.