Introduction
I left the web startup I joined as my second company in August 2022, and became a freelance engineer in September. The main goal was a pay raise. Not many people around me go freelance in their 20s, but if you are in a similar spot and considering it, I hope this is useful!
Agents
The agents I used!
Levtech Freelance
This is the freelance arm of Levtech, an IT-specialist agency. I also used them for my mid-career move. They are strong on IT, so I recommend them! You get introductions from the agent, and you can also search for companies yourself.
TechBiz
https://freelance.techbiz.co.jp/
An agency that includes tax-accountant support. They will walk you through filing the notification of opening a business and the tax return for free. The flow is mostly: they introduce companies, you pick the ones you want, and you interview.
How the job search went
Schedule
| Period | What happened |
|---|---|
| Late April 2022 | Decided to resign and change jobs. |
| Early May 2022 | Told my manager I would leave. |
| Early July 2022 | Started the job search in earnest. Interviewed after work. |
| Mid-July 2022 | Got an offer and ended the search. |
| Late July 2022 | Last day in the office. (Resignation date: August 31, 2022) |
| September 1, 2022 | Started at the new company. |
Freelance hiring closes much faster than new-grad or mid-career hiring (mine took 10 days). On a mid-career move, a company might wait a month from offer to acceptance. On a freelance move, they will wait a few days at most (up to about 5). It is hard to hold several offers and keep interviewing for better terms, so start with the companies you want most.
Companies often look for people who can start in 1 or 2 months. Listings for a September 1 start began trickling in in early July, then increased in mid-July, late July, and early August.
What actually happened
I applied to 5 companies and got 4 offers. I did not get an offer from the highest-level company I most wanted to join, but compared with my first job search it went very smoothly. Leadership experience and mentoring new grads counted for a lot.
From looking at roles, even for Java there are plenty of remote roles if the stack is Spring! The one I joined is a fully remote Spring project.
What to do before you start looking
Same basics as a mid-career move: ship results at work that you can talk about. I also wrote up that first job change — take a look!
【Job Change】From an SIer to a Web Startup: My Engineering Job-Change Story!
Learn tech with high market value
To raise your rate, work with languages and tech that the market pays for! Talking with agents, these were especially high-rate and worth learning:
- Go
- Kotlin
- React.js
- TypeScript
Looking at listings, those languages do show up at high rates a lot. Spring, which I use, is reasonably high, but it still feels a step behind.
How it felt after switching
The biggest worry about going freelance is will I actually be good enough? On that point: if you were good enough as an employee, you will be fine! You do not suddenly do something completely different just because you are freelance. Culture differs depending on whether the company is more SIer or more web-startup, and the level differs by engagement. Your role also depends on how you were hired. Whether you “cut it” depends more on the company you join than on employee vs. freelancer.
Paperwork to become a sole proprietor
Going freelance means a pile of paperwork. I also wrote a recap — check that too!
【Social Insurance and Tax】Money basics freelancers should know!
National Pension
As an employee you are almost always on Employees’ Pension. As a freelancer you have to enroll in National Pension yourself. You can pay by bank transfer or credit card, but you need to file a transfer request. Acceptance takes time, so for the first 1 or 2 months you will pay with a payment slip. You can file by mailing the forms, but you cannot file before your resignation date. Prepare the documents and send them after you leave!
What to submit
- Application
- Transfer request (if you want bank or credit-card transfer)
Deadline
Within 14 days after leaving the company
National Health Insurance
You also have to enroll in National Health Insurance yourself (unless you join a union plan). Same as National Pension: bank transfer is available, and you can file by mail. Prepare ahead and send after the resignation date!
What to submit
- Application
- Transfer request (if you want bank transfer)
Deadline
Within 14 days after leaving the company
Notification of opening a business
As a freelancer you are a sole proprietor, so you need to file a notification of opening a business. Most people also file for blue-form tax returns as a tax-saving measure, so file that at the same time!
If you use the freee accounting software, you can finish this online. I recommend it!
What to submit
- Notification of opening a business
- Application for approval of blue-form return
Deadline
Within 1 month of the opening date

