I recently quit being an independent contractor after 5 years and returned to being an employee. Let me outline my experience going from employee to contractor and back.

In general: I have been a software developer for 14 years. I love writing code but I also like to figure out the root of the problem and come up with the best solution. I started freelancing in Germany and continued to do so in the UK and the US.

The initial reason to go solo was mostly feeling based. I imagined being super flexible about what I could work on and wanted to have more time off even though it was unpaid. Additionally I thought I could spend some time to specialize in a field in order to get higher rates and maybe come up with a product idea. I also justified this move to myself with "I at least gotta try it". I was lucky to find a client pretty quickly and enjoyed the networking and finding follow up opportunities.

However a couple of things became pretty clear to me very quickly: the easiest way to work as a freelancer for me was to basically continue to work as a generic software engineer that knows $language for a client 5 days a week and then invoice them. I didn't really spin up additional income streams and I didn't even take more time off.

However there were a few things that kept me from returning into a regular job: The increased income (in my first year my income effectively increased by 50% even though I was doing the same work), the opportunity to switch "jobs" more often without it being perceived as being a flaky employee (this one is kind of a hack but nobody ever questioned why I was only working for 3 months for a particular client).

Things ultimately changed after I moved to the US because the calculation now wasn't only about pure money. I also would have to factor in health insurance cost (in Europe this is essentially the same wether you are freelance or not), there are other benefits like 401k contribution and employee stock buying programs that I needed to consider. But ultimately I was missing working on projects long term rather than just coming into a company churning out code. I also enjoy not having to write invoices anymore or doing a more complicated tax return or figuring out what kind of insurance I need. I am also glad that there is now basically no need for me to do any kind of marketing or sales related work.

In total I had 9 full time clients and a few short term projects (1-2 days). The short term projects were some of the worst days as a freelancer because the project was timeboxed and every time I scrambled to deliver on time.

In general I would say if you are an hourly/daily rate based contractor the only two reasons that I saw as an advantage was: more money and seeing more different projects. If you are willing to put up with the admin overhead of going solo I definitely recommend it, especially if you have a talent or are willing to do marketing and sales related tasks. I suggest however to be honest with the income calculation. If you compare your current job to something like 220 billable days as a freelancer (not unrealistic) you are going to see a big increase. But if you take into account the benefits and compare this to a competing employment offer, the income difference might not be as big.