This episode asks why freelancing is increasing and why some people leave it. Looking back at changes in working styles since 2020, we asked Masa, who began his career as a sole proprietor, what it takes to remain independent for the long term. The discussion offers concrete insights into preparation and output, often overlooked precisely because starting has become so easy.
The Growth of Freelancing Since 2020 and Masa's Position
HAL: This time, we are discussing why freelancing is growing and why some people quit. With remote work spreading since 2020, it feels as though more people have become freelancers. Did you also become independent as part of that wave, Masa?
Masa: No, I never took a salaried job to begin with. I have always worked freelance, as a sole proprietor, so it is not that I became independent after 2020. I have seen the increase since then more as a change around me than a wave I joined.
What Happened in 2020: YouTube, Video Editing, and Side Jobs
HAL: What kind of turning point for work do you think that period around 2020 represented?
Masa: I think 2020, with the pandemic, was when YouTube suddenly became widespread among the general public. People said video editing would become popular and could be done remotely as a side job. The term side job spread, and YouTube video editing became more widespread alongside it.
Why Some People Cannot Keep Going
HAL: Video editing became an accessible side job, and options increased. Now it feels as though that wave has run its course. Where do you think the difference lay between those who could continue and those who could not?
Masa: Freelancing fundamentally means starting an independent business. In older terms, it is essentially the same as a salaried worker leaving their job to open a ramen shop. Yet because it was easy to start, I feel quite a few people took claims that anyone could easily begin a side job online at face value. I think those were the people who struggled to continue.
Preparation for Independence: Training, an Offering, and Customers
HAL: So being easy to start does not mean being easy to sustain. What should people prepare before becoming independent if they want to continue long-term?
Masa: Independence is something you are supposed to prepare for. In the trades, an apprentice becomes fully qualified, leaves their master, and starts independently. That preparation is why they can keep going. You build skills and experience through training and start because you are ready. What really struck me from watching nearby was how many people started without either skills or experience.
HAL: Could you explain that preparation more concretely?
Masa: Business basically has just two things: something to sell and customers who buy it. If both are in place before you become independent, that is absolutely ideal. If they are not, you need a certain level of skill. When attracting a new customer, they look at your track record and skills, recognize the experience you have, and decide to hire you. You approach them after getting yourself into that position, so preparation really matters.
The Trap of Free Information
HAL: Is there anything people should keep in mind in addition to preparation, particularly today?
Masa: As I mentioned, there is a problem with taking free information on the internet or social media such as Instagram at face value. Information that is easy to get is being provided for free so the person sharing it can make money. You have to understand that as you listen. And there is really no easy path to riches.
Escaping the Cycle of Low-Paid Work
HAL: Free information has its provider's intentions behind it, and the sweeter the promise, the more care it needs. If you had to name one thing someone considering independence should assess, what would it be?
Masa: We have recruited people ourselves and received quite a few applications, but most applicants have very few skills and come saying they want work for experience. Without a track record or experience, they inevitably have to charge little. If they keep taking cheap work for experience, that way of working becomes a cycle. They grow older without escaping low rates and keep doing it without realizing.
Masa: By contrast, people who move up to better-paid work create their own pieces and release them themselves. They use those to approach higher-paying clients, gaining experience and a track record that lets them progress further. That becomes their cycle. So I think the most important thing is whether you can make something yourself and put it out into the world.
The 100-Project Challenge: Developing Skills and Generating Business
HAL: Publishing your own work sounds like the key to reaching the next level. How much work should someone aim to build up?
Masa: A hundred, really. A university student might use AI to build websites or apps; in the past, they might learn coding and build a hundred websites themselves. As they make them, they naturally release that output. It accumulates, attracts attention, and brings requests. So doing a hundred-project drill ultimately develops your skills and also serves as sales activity. If you instead keep accepting cheap work right in front of you, I think you become unable to escape.
HAL: If you were doing the hundred-project challenge now, what would you create?
Masa: AI videos. I would experiment with different ways of making them and create a hundred. And now you can also use Claude to build apps and websites, so I would keep going on that front too, with the momentum of making a hundred sites.
HAL: Thank you. Today we covered the growth of freelancing, the preparation needed to continue, and the hundred-project challenge of creating and releasing your own work. The key to escaping the cycle of cheap work for experience lies in the output you build with your own hands rather than someone else's free information. That was the message of this episode. Please watch the YouTube video for the practical methods and further discussion we touched on today. See you next time.
