I ended up working as a developer for an digital agency based in Toronto. It was relatively small (~10 people, in total) but catered to some huge clients. I realised that, with experience in freelancing (managing my own time and projects), consulting (working with non-technical clients on technical projects) and development itself, my skillset was varied enough that the jump from freelancer to simple subcontracting to business owner shouldn't actually that large a move. Once I thought of that, not doing it seemed impossible. I can't say it's been as smooth-sailing as I thought but I've been doing it for a little 2 years now and we're still here.

The biggest shock was probably the amount of time it takes to simply manage the business. While I was used to a degree of bookkeeping and simple project management from freelancing, I wasn't quite prepared to spend a fifth of my time managing the everyday flow of the business, as I find myself doing now. It's a natural progression, but I still can't say I'm quite used to it. I am better at planning for it though, and ensuring that my time spent project managing is taken into account. Hope that helps.