Hi Netflix,
I was freelance for about four years, working mainly for one company, then worked briefly with another company before deciding to set up properly as a ltd company, with my DH, in 2016. There was an element of risk involved because DH was leaving a full time job, but for me it was just a matter of carrying on freelancing in a more 'official' way.
I love it, it was the best decision I ever made and I kick myself that I didn't do it earlier. Yes, it has drawbacks - some days I feel utterly fucked off, tired and stressed. But that is more than balanced out by the days where I feel totally elated. It's definitely much more of a rollercoaster than being employed and you have to be prepared for that. It suits some people and not others. It definitely suits me!
The cons are obvious - having to bring in your own contracts, the worry of not making enough money, the responsibility for admin, tax, premises etc, shitty clients, late invoices, working long hours, etc.
The pros are great though - flexibility (I can attend all school events for my children, I just need to plan my diary) without anyone looking over your shoulder watching your time/days, control over who you work with and when, seeing the direct benefit of your hard work, rather than it being absorbed, unnoticed, into a big company, winning new contracts on your own merit (that's a high!), depending on your area you may earn a lot more than what you did as an employee, feeling like you're building something, like all your extra hours are worth it, having the opportunity to provide employment to other people (I employ my best friend as a contractor), a sense of ownership and meaning.
Remember too that if you build a successful company you may at some point in the future sell it - you are building an asset that could be very valuable.
I think apart from the money element a lot of the benefits are quite intangible. Yes, the lack of sick pay, maternity pay etc can be a bit terrifying but that's very quickly outweighed by the fact that if I get, say £20k for a project, that doesn't just get sucked into the Accounts department and slowly meted out to me according to my contract, that's my £20k and I can use it to build my business (or to buy insurance so I don't have to worry about getting ill!)
I'm worried about being too positive, because I know it's not for everybody - a friend of mine started his own business around the same time as me and seems to torture himself over it - he expects such a lot of himself and has no patience to wait and see how things work out. I think he'd be better off in employment - he needs quicker rewards and more direct encouragement (when you own your own business you absolutely must be able to sustain your own confidence, your success depends on it.)
I would say to give it a try and be ok with it if it doesn't suit you. Don't expect success instantly, you do have to hang in there. Some people will be very negative and put a dampner on it, you have to ignore that, much of it will be jealousy/not getting what you're doing. Look to the supportive people to sustain you. Find people in the same boat (this is a good start!). Good luck!!