Can I continue to be a freelancer? For life?

the company you build is only what you build it to be.

if you want to build it with your freedom in mind, there are ways.

Hopefully while freelancing you'll meet lots of different people and leave a good impression. Then in later years you should have enough of a network to get a sufficient amount of requests for freelance work. I am not that old yet, but I've seen it work for some older friends.

I don't see why a company should be inherently more secure than working as a freelancer.

You should check out "4 Hour Workweek" by Tim Ferriss. I'm only halfway through, but he has already touched on a lot of concepts that I think would really hit home with your concerns for freedom.

I run 'yet another web design company' and while I don't have a family, my social life is rewarding and I don't usually put more than 30-40 hours in a week.

Why do your friends and family think that? Do you agree with them?

Given your freelance background, I would imagine you might know more than most first time entrepreneurs? I haven't met any business owners who surrender having a life for their biz (though I haven't met any multimillionaire business owners, either). Perhaps finding patterns in your freelancing and building those solutions into products while continuing the per-project work would be a good in-between to help you decide?

Why not? I work as a freelance software consultant, and I just switch between working on other people's projects and working on my own projects as needed. I don't have any plans to stop this anytime soon. Maybe as I get older I'll change the ratio of consulting/not-consulting to provide for a family, or I'll find some other way to generate money and stop working as a consultant, but I really see no reason not to just do this indefinitely.

Freelancing is good, but is it sure? If yes, then don't care and live the way you like, if no, then think again.

A company = Hard work, but is more sure than freelancing

Do you have health and long-term disability insurance? If you tomorrow get into an accident and lose all your fingers, are you going to end up living in a box on a street corner? If you make sure that your freelance gigs pay you enough to take care of that part of life, there's no reason why you can't continue doing what you are doing for as long as it makes you happy.

Dude, you're missing the best part: maybe you won't be the one who has to do the actual work.

Spend your time making sure the work's good, meeting customers, making business.

Then, eventually, stop even doing that and live off your equity in the company.

I've known many people who've made a living well into their 50's doing freelance work, and they lived quite comfortably (nice car, nice house, nice and long vacations, etc.). Not web design, but I can't imagine IT and database apps are dramatically different from design for freelancers. I did freelance work on and off for about five or six years, and was always well-paid when I did.

Treat your customers better than they deserve, work dramatically harder than you would if you were on the payroll, charge through the nose, and make sure you interact more with the customer than the design (or servers, or database, or whatever; the way you explain things is more important than what you do...you have to do a good job, but if you fail to explain it well and in a way the client understands, you won't get referrals and you won't make the client happy). These are the keys to living happily and being well-paid in a freelance business.

It's difficult as a solo consultant to build a sustainable business: you have only your hours to sell, it's difficult to stockpile them, and jobs arrive unpredictably. When you are busy it's hard to look for additional work, so that porpoising (alternating periods of work and idleness) is hard to avoid. I would look to join up with another two to four like minded consultants. This gives you an opportunity to spread out your marketing and sales efforts across the group, take on larger assignments, and have backup in case of illness or other temporary inability to complete the job. Partners also give you time to renew and enhance your skillset--obsolescence of expertise is another business level risk--and others to compare notes with in new or challenging situations.

I have a few thoughts on that, because my work/life concept is basically the same as yours.

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.