Twice in the last 24 hours I’ve come across two glimpses into the life of the freelancer / writer that struck a chord.  Chris Guillebeau, who is the author of an inspiring and useful manifesto called 279 Days to Overnight Success also sends out a weekly newsletter called “The Art of Nonconformity [AONC].”  From his last newsletter, about the life of a freelancer:

It’s always fun to go on vacation as a self-employed person because a) you still have to work, and b) no one thinks you do any work to begin with.  So then when you go on vacation they say, oh, must be nice that you don’t have a job and can do that.  Meanwhile on vacation I work six hours a day instead of ten.

And then I came across this passage in Anne Lamott’s “Bird by Bird, Some Instructions on Writing and Life”:

Every morning, no matter how late he had been up, my father rose at 5:30, went to his study, wrote for a couple of hours, made us all breakfast, read the paper with my mother, and then went back to work for the rest of the morning.  Many years passed before I realized that he did this by choice, for a living, and that he was not unemployed or mentally ill.  I wanted him to have a regular job where he put on a necktie and went off somewhere with the other fathers and sat in a little office and smoked.  But the idea of spending entire days doing someone else’s work did not suit my father’s soul.  I think it would have killed him.  He did end up dying rather early, in his mid-fifties, but at least he had lived on his own terms.

And my reflection is this: life, especially professional life, is becoming much more like freelancing.  The most important decisions we make every day – even if we have “regular jobs” – are how to spend our time, defining what success looks like for ourselves and for our customers, and figuring out who our customers are and how best to serve them.  This is where we all have the most leverage, and it’s a shift that’s happened in this last decade as markets have fragmented, costs of production have plummeted, and networks have become ubiquitous.  And it means that we all are, to a greater or lesser extent, a lot more like freelancers than ever before – and if we’re not acting and thinking like freelancers we’re missing an opportunity.

It’s easy to romanticize the life of a writer or a freelancer – in reality, as Chris reminds us, it’s hard and uncertain because you have to have the discipline to decide how to spend your time and to create the structure you need to produce your work (your art).

But what’s deceptive about “regular jobs” is that it’s incredibly easy to fool yourself into thinking that these aren’t your choices to make – because you have a full inbox and lots of meetings to go to and a boss telling you what you have to get done and when.

The moment you start looking at the 24 hours in your day and how you’re going to spend them, the moment you open the door to the possibility that you could wake up at 5:30am to do what you do best – whether blogging or writing or learning a new craft (or programming language or computer software or foreign language), or just going above and beyond for the job that you already do and love – is the moment you open the door to real possibility.