I went freelancing relatively recently, but I think my situation was a bit unique. Going freelance for me meant I instantly made more than twice the yearly income, and I had two contracts spanning almost 2 years waiting for me. So, my opportunity meant I could stop commuting 2 hrs a day to an office, I could work closer to my home and my family, I could set my own hours (besides meetings and stuff), and enjoy almost a 300% pay raise.
Oh, and when I told my old boss I was thinking about leaving, he offered me a 10% raise. So yeah, the decision was more than easy for me! Good luck to you.
All freelancers situations are unique.
I think your situation is more like trading one job for another except with a different tax situation. This isn’t a bad thing, but it’s a good example of the different ways you can go.
I believe you have two ends of the spectrum when going solo in web development. I would call them freelancer and contractor.
On the freelancer end you put a strong emphasis on being an independent business and building your brand. On this end you probably take on a relatively larger number of clients and choose work which will specifically help you build your brand.
On the contractor end you tend to gravitate more towards a small number of clients or perhaps just one client. If you are in this situation may just sort of just fold yourself into that business rather than working on your own.
I think being on the contractor end can be more risky for a long term sustainable business. A business relies heavily on networking and marketing and the freelancer end is much more powerful for these sorts of things than the contractor end. The more clients you deal with, the more exposure you get, the more varied projects you work on and the bigger your network grows.
I also think Freelancer is ultimately more lucrative. As you build your brand, your perceived value goes up, you gain more demand and the rates you can charge go up.
Really this is all semantics though. Most people probably just have to take what they can. I would rather be making good money as a contractor than be a starving freelancer.
If you really want to start a great business, you won’t do freelancing at all. Your ceiling is the number of hours in your day. You are trading dollars for hours. Either find out a way to make money from the efforts of others or create something that you can scale better than your available hours. I mean, if you are going into business, you might as well do it right. 😉