Out of nowhere, I found myself wondering what the old bloggers are up to these days. Iwa Tower, Majimaji Party, Yagipe, Ikehaya, Hitsuji. Between roughly 2015 and 2018, the Japanese internet had a breed of people known as "pro bloggers."

"I dropped out of university." "I quit my job." "I made a million yen a month from my blog." Announcements like these filled the Twitter timeline almost daily. "Still wearing yourself out in Tokyo?" "Live doing what you love." Those slogans make me wince a little now, but back then they sounded genuinely fresh.

You could live without working for a company. With one laptop, you could work wherever and whenever you liked. There was a real expectation in the air that the internet would liberate individuals from organizations.

About ten years have passed. A bit of digging shows that a surprising number of them are still going strong. Jinpei Yagi turned self-understanding into a business. Hitsuji develops WordPress themes. Keita Oki runs a content production company, and Hitode reportedly built enough wealth from blogging to reach FIRE. Of course, there are also names you hardly hear anymore.

What's interesting is that most of the ones who made it are no longer "pro bloggers." They won their freedom through blogging, and then, to keep that freedom, they walked out of blogging.

They needed to break free from the very work they had taken up to be free.

The Other Company Outside the Company

The appeal of the pro blogger life, I suspect, was never just the money. No boss. No commute. No packed trains. You decide your own hours and your own place. It was a small act of rebellion against letting a company manage your life.

But once your blog pays the rent, a different problem shows up. Drop in Google's rankings and your income drops with it. Change the algorithm and the value of everything you've written can shift overnight. No matter how hard you work, you are not the one who decides where you appear in the search results.

As an employee, your boss decided how you were evaluated. Once independent, the algorithm decides. Of course the two aren't the same. Google is not your employer, and a blogger is free to choose their work. Still, in the sense that decisions shaping your livelihood are made somewhere beyond your reach, the structure is similar.

You stop worrying about your boss's mood and start worrying about your search rankings. You stop checking your pay slip and start opening Google Analytics several times a day, like a day trader glued to the ticker. You were supposed to be free, yet the numbers push you around more than ever. I'd bet there were days like that.

Quitting your job and living without depending on anyone turned out to be two entirely different things.

Building a House on Rented Land

Come to think of it, the history of the internet may just be this same story on repeat. Write a blog and anyone can own a media outlet. Upload to YouTube and anyone can be a broadcaster. Use social media and you can reach tens of thousands of people. And now, with AI, a single person can produce software and content in bulk.

Things that once required belonging to an organization are being opened up to individuals one after another. That is unmistakably technological progress. But that freedom comes with one condition: you operate on top of a platform.

Work on YouTube and you follow YouTube's rules. Draw traffic from Google and you adapt to Google's criteria. Sell an app and you abide by the App Store's or Google Play's terms. If you use the system, all of that is only fair.

Even so, there is a strange asymmetry here. In effect, you are building a house on rented land. Users pour time and effort into building assets on that land. Meanwhile, the roads that carry those assets to people are controlled by the landlord, the platform. A hundred thousand followers doesn't mean a post reaches a hundred thousand people. Hundreds of published videos don't guarantee anyone will watch the next one. Ranking first in search doesn't give you the right to keep living there.

You built it yourself, yet you can't decide its value on your own. Put plainly, the land is appraised by the landlord, not the tenant.

What's more, the bigger the platform grows, the more people move in. Lower barriers to entry create opportunities for people who couldn't participate before. At the same time, competitors keep putting up houses on the neighboring plots. When anyone can do it, anyone will show up.

The very technology that frees individuals slowly erodes their scarcity. A rather ironic arrangement.

YouTubers Are Walking the Same Road

Watching today's YouTubers, I get a similar feeling. Not long ago, simply making a living from ad revenue on videos was news. Film what you love. The views go up. The ad money comes in. Plenty of young people dreamed of a life that ran on nothing more than that.

Now, though, more and more popular YouTubers are launching apparel brands, opening restaurants, or selling their own products. People who made their name on YouTube start businesses outside YouTube. I've seen this scene before. It's exactly the same picture as bloggers who made their name on blogs and then started selling things outside them.

Sure, some people earn plenty from ad revenue alone, and YouTube as a market isn't going anywhere. But staking most of your income on view counts is a fairly precarious position. New creators appear. Audience tastes shift. The criteria change. You get older, and making the same kind of videos becomes harder.

So you make your own products. You build your own brand. You connect directly with your own customers. Alongside the rented land, you buy up little plots in your own name. Seen that way, starting a business outside YouTube isn't mere money-grabbing; it's a hedge against an uncertain future.

And before you know it, the person who didn't want to be tied down by a salaried life has founded a company, hired employees, and is running an organization. They are building, with their own hands, the very thing they once wanted to escape.

Of course, an owner and an employee differ in position and discretion, so it isn't a simple contradiction. Still, the pursuit of freedom ends with you shouldering more responsibility and a bigger organization. Life is funny that way.

And Now, With AI

Lately, solo development with AI is all the rage. Even without much programming knowledge, you can build an application by giving instructions to an AI. Images, video, articles too. One person can do what used to take a company.

I think this is a genuinely big shift. Just as blogs gave individuals a media outlet and YouTube gave them a broadcast station, AI is trying to give them something like a development team. Work that took several people runs with one, and ideas that once needed funding can take shape at low cost. A future where you live off your own product without belonging to a company has become far more plausible than before.

But here I can't help pausing. Doesn't that sound a lot like the future the pro bloggers were describing ten years ago?

Back then, people said anyone could build a media outlet as long as they had WordPress. Now people say anyone can build an app as long as they have AI. Back then, the hope was that writing lots of articles would raise your income. Now the hope is that if you build lots of apps, one of them will hit.

Of course, the two are not identical. Blogs and software differ in the value they provide and in how they make money. Still, the plot is much the same: barriers to entry collapse, and new success stories of individuals emerge. And whatever anyone can make eventually loses the value of merely being able to make it. Just as running a blog stopped being special and editing video stopped being rare, building apps will probably become ordinary too.

When that happens, what remains? The ability to write code, or to wield AI? Or the ability to find whose problem to solve, and which one? Probably, the easier making things gets, the heavier the question of what to make becomes.

There is one more problem: to whom, and how, do you deliver the product? AI may lower development costs, but users won't gather on their own. Just as bloggers once depended on Google Search, solo developers may come to depend on App Store rankings and social media algorithms. Building the house has become almost free, but the land is still rented.

Gaining the freedom to make doesn't give you the freedom to reach people. Perhaps the bottleneck on freedom simply moves somewhere else.

Beyond "Anyone Can Do It"

Technological progress increases the number of people who can do things. That in itself is wonderful. But more people being able to do something isn't necessarily the same as more people being able to earn from it.

More people writing blogs doesn't give readers more time. More people making videos doesn't stretch a viewer's day past 24 hours. More people building apps doesn't change the fact that we only use so many apps on our phones each day. No matter how much supply grows, human time and attention barely grow at all.

The result is more people fighting over a limited pool of attention. To win that attention, they adapt to the platform's mechanics once again. They pick titles that get searched, make thumbnails that get clicked, and choose words that get shared. What gets seen takes priority over what they actually want to make.

Before long, someone who was supposed to be doing what they love is making what the algorithm loves. Of course, this doesn't apply to everyone. There are lucky people whose passions happen to match market demand.

Even so, this is where the difficulty of "live doing what you love" lies. The moment you turn what you love into work, that work has to be judged by someone and paid for. As long as you live in a market, you can't only do what you love. The freedom to make a living from what you love and the freedom to do only what you love may look alike, but they are completely different.

What Is Freedom, Anyway?

Having come this far, I started wondering what freedom even is. Not working for a company? Not being told what to do by anyone? Living wherever you like? Having enough money? Each of these is surely part of it.

But living without depending on anyone is probably impossible. Employees depend on their company. Freelancers depend on clients, bloggers on search engines, YouTubers on platforms and viewers. Entrepreneurs depend on customers and markets, and even investors aren't independent of markets and social institutions. Whatever life you choose, you'll be renting land from someone.

Seen that way, freedom may not mean eliminating dependence, but being able to choose what you depend on. Not having your life collapse if you lose one source of income. Being able to choose other work if you come to hate your current job. Being able to quit something you loved once you no longer love it. Having enough room to take a shot when you want to start something new.

Freedom, then, is probably not the absence of constraints but the state of not losing your options. That may take money, or skills, or connections with people. And it also takes reexamining your own values from time to time.

It's Fine for What You Love to Change

Watching the old pro bloggers, I noticed one more thing. It's fine for what you love to change.

Someone who loved blogging in their twenties can come to love building businesses in their thirties. Someone who goofed around on video can want a quiet life in their forties. Declaring "this is how I'll live" once doesn't oblige you to keep doing it forever. People change.

The internet, however, dutifully preserves your past self. What you said, filmed and wrote ten years ago all stays right where it was. So when you start doing something different, people say you've changed. You used to say freedom mattered more than money. You used to say nobody needs a company. You used to say you'd live only doing what you love.

But is that really a contradiction? If anything, it would be far stranger not to have changed your mind in ten years. Someone who vowed to live freely ends up losing the freedom to change their own values. That's putting the cart before the horse. Your present self has no duty to keep defending the ideals your past self proclaimed.

I'm no exception. When I reread posts I wrote on this site ten years ago, my face sometimes goes hot. Why I haven't deleted them is something I'd rather you didn't ask about.

"Living Doing What You Love," Ten Years On

You don't see many people aspiring to be pro bloggers anymore. Yet blogs are still here. The job of YouTuber will likely take a different shape someday too. And the AI solo development that's booming now will surely be completely ordinary ten years from now.

When that time comes, what will today's AI solo developers be doing? Some living off their own products. Some running companies. Some back in other jobs. Some who built enough wealth to stop working. There will be all kinds of lives, and some of them will be enjoying something entirely different from ten years before. I think that's fine. If anything, being able to change like that may be what freedom is.

The pro bloggers used to say, "Live doing what you love." I think I once took that to mean doing the work you love for the rest of your life. Now I read it a little differently. Living doing what you love isn't a vow to keep doing it forever. It means being able to choose your life over again, even when what you love changes.

So that's where a trivial question about what the old pro bloggers are up to these days has led me, a long way from where I started. One thing, though, is certain. The freedom they were after back then surely wasn't blogging itself. Blogging was just a means of getting that freedom, and the means changes with the times. From blogs to YouTube, from YouTube to AI, or on to something that doesn't have a name yet.

Every time a new tool appears, someone says, "Now individuals can be free." The same thing will no doubt keep happening. Even so, the human wish to be free doesn't change.

Depending on the things that give us freedom, while trying to become free of them. Maybe that is what it means to live on the internet.