People always talk about the United States being much more amenable to entrepreneurism. From my experience, I would agree that this is true - culturally. However, taking the leap from salaryman to entrepreneur or freelancer in the USA is much more risky than in Canada, and the reason for that is health care.
The US system of patient-or-insurance-paid health care is a great social control system to encourage people who aren't otherwise wealthy to find corporate jobs and stay in them. I don't really want to get into the debate about quality, access, costs, or even social justice - but I seriously doubt that I would have pursued my decade of freelance work and now the challenge of starting a new independent venture if I had to worry about either large insurance payments or massive costs in case of some terrible disease or accident.
I had always understood that health insurance in the US was expensive, especially if you're paying for it yourself, but then I read this post from someone leaving his day job:
Obviously, I can take advantage of COBRA with my current employer, which might be a viable short-term option (up to 18 months). This would be about $1500 a month (for family coverage), so it’s a bit expensive.$700 to $1500 a month? That's decent rent in downtown Toronto. I've been considering getting rid of my car because I don't use it much and it would be good to not have to spend the extra $1500 a year to keep it insured. If I had an extra $1500 a month in expenses ($18,000 a year!), I'd probably have to give up on Shindig and get a full-time job in the J2EE pits at a bank or something.
Since LogicalVue is a corporation, there are also several small-company health care plans that are available. First, Maine has something called DirigoChoice health care. It’s administered by Harvard Pilgrim and would run about $1,100 a month or so ... And I also have a couple other plans from Anthem and Aetna that run about $700 to $1,100 depending on deductibles and coverage.
Of course, Canadians end up paying for health care through our taxes - but the nice thing about that is that we only have to pay out so much once we're already making good money, not when we're struggling to get things started.
So, in this case, a bit of socialism can actually help small businesses and entrepreneurs.