Am I ready to go contracting ?

I have been working as contract/freelance for some years now and I’ve worked in a lot of different places. I meet a lot of talented people who are “permies” and I quite often get asked variations on the question, “I am thinking of going contract, what do you think ?”. I’m normally quite happy to give people advice on things like this. I am certainly happy to go through the pros and cons, the ups and downs, the ins and outs of life as a contractor. I will regale people with anecdotes, epic tales of heroism and horror, triumph and tragedy, success and suckiness etc, but at the end of the day my answer to the question “Am I ready to go contracting ?” or “Should I go contracting ?” will always be “No”, and I will tell you why.
Becoming a contractor is, above all, a leap of faith. It requires tremendous self-confidence, chutzpah, front, balls whatever you want to call it. You have got to be 100% sure of yourself. Sure you can get the job, sure you can do it, sure you can keep it or find another one quick. You have to be able to go and do the work every day, run the risks and go home every night and get a good nights sleep. If you are the kind of person who will lose sleep over the uncertainty associated with contract employment, “don’t even go there, Girlfriend”. You may be able to do the job but you will be tired and miserable.
And that’s why I say “No”. The very fact that you are asking the question means you aren’t ready. You will be ready when you know you are ready. If you need anyone else other than yourself to convince you that you should go contracting then you shouldn’t. You have to make that decision on your own and carry the weight and responsibility of it on your own. If there’s anything worse than finding yourself in the sh*t, it’s finding yourself in it and thinking “If only I hadn’t listened to whatshisname!”
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