Autonomy vs. Resources
One of the trade offs of working for yourself instead of a large company is that when you go to work for yourself, you give up resources for autonomy.
Autonomy means you can act faster to implement your own ideas.
Want to update your website? You just go do it.
Want to pitch a new client? You dig up their e-mail and shoot them a note.
At a large company, you would probably have to go through many layers of management or committees to get anything done.
That being said, once an idea is approved, you have more resources (money, personnel, contacts, etc.) to execute.
If you have a big idea that you want to implement working for yourself, you will need to find ways to make do with less money, less people, etc.
Yes, you can update some text on the website pretty easily, but can you design a new app? You will need to hire a software developer and spend tens of thousands of dollars.
So ask yourself what pain is more tolerable to you. The pain of being resource limited? Or the pain of trying to persuade a committee to implement your idea?
If you choose to be resource limited, you should probably work for yourself.
If you prefer to work with large teams and get buy in, you should probably work as a W2.
Want the full playbook? Check out Going 1099.