1. Extra financial security and these things. I honestly belive the best way to secure a good future in this areas is to get into farming somehow. Not necessarily doing the work on the land you don't want to do, but having access to foods you actually know how they were generated is the point. For example one could form a group of like-minded people and have one local farmer as some sort of service provider. Something along that line will be far more important in the next decades than the thing with the car.
2. To make a career out of freelancing, the key is always raising your rates. There are copywriters who earn ~30,000$ per assignment (which they say takes 4-5 weeks). Well, you can count these with the finger of one hand, but the principle is the point. That means, if you want to earn more it is not required for you to un-freelance.
3. Instead of founding an agency you can develop trusted teams for various kinds of works. So you can have the adventure of working on bigger projects if you like or check out other industries than your "home play".
4. The passive income thing does not mean you have to do products (and thusly becoming a manager/owner again). You can have a couple of projects where you get paid with royalties, at least partly.