There are two ways of going into business for yourself: The way described in books, and the way that it really happens.
On the surface, the standard advice sounds sensible in its caution: Do your research before beginning, build up your business on the side, and don’t quit your regular work until you have at least $100,000 in business lined up. Follow this advice, and you’ll never do anything rash or ruinous.
You will also, very likely, never go into business for yourself at all. The chances are, you will always find the moment not quite right, and decide to wait until you have a little more work in reserve, or finish paying off a particular debt.
While I applaud the standard advice in theory, I don’t think that any of the self-employed people I know – and I know dozens – ever followed it. Instead, most people seem to follow one of two paths.
On the first path, people find themselves unemployed or under-employed, and figure they have nothing to lose by starting their own businesses or setting themselves up as independent consultants. Sometimes, they have wanted to work independently for years, but never had the courage to do so before. Other times, they seize on the idea in their current crisis. But, however they reach the point of decision, they have reached a point at which they are desperate, and, perhaps, tired of working for other people who seem no smarter than them. Having nothing to lose is a wonderful motivator – even better than deadlines – so people on this path set out to do whatever it takes to establish themselves, working hard and borrowing money if they have to.
On the second path, people never make a conscious choice to work for themselves; their career just works out that way. Maybe contracting is the easiest way to break into a line of work. Or maybe they start taking on extra work in the evenings and the weekend to help pay the mortgage or to bring in a little more income. Slowly, their regular work becomes less important to them, and their sideline grows until, suddenly, they realize that it means more to them than whatever they’re doing for their regular pay cheque. They discover that they like the independence, and, at an opportune moment, they consciously choose it.
My own route to becoming a freelance journalist is an example of the second path. I don’t think I ever had a moment when I consciously decided to be a consultant. Nor do I seriously believe, as I sometimes joke, that I avoid full time employment because companies I join have a tendency to have financial crises six months after I come on board. Being a communications consultant was just the easiest way to break into technical writing and marketing when I shifted from academia. Before long, I had the experience and the income that I didn’t need to look for full time work – in fact, a permanent position would have meant a reduction in income. I wavered a bit because of a personal crisis and the excitement of the dot-com era, but I eventually found myself doing more and more journalism, and being more and more bored with office work. Eventually, I had an epiphany about which I enjoyed best, and I never looked back.
But, whichever your path to working for yourself, I think that what matters is that you are most comfortable with independence. Desperation drives many other people to take small consulting contracts or even set up their own businesses, but most flee back to the security of full-time employment as soon as it’s offered. Rather than sensible planning, what unites the self-employed is that, when they stop to think, they really would prefer to do things for themselves.