I like to give practical advice to people who ask me about what it’s like working for yourself. I’ve assembled lots of tools and strategies to help me manage projects and clients, but the truth is that I think personality and attitude have more to do with it than anything. Not being too afraid to proceed on a trial-and-error basis, being comfortable with mess and quick to abandon structure for fun and being supple in the face of chaos are very helpful when dealing with the confusion and uncertainty inherent in creative self-employment (and the universe in general).
Given the personal inclination, creative self-employment isn’t really as risky as you think. If you’re under 30, it’s quite possible that you won’t see the same quality of life as your parents. And if you do, you won’t get there the same way that they did. The factors that configure national economies and workforces have changed so much that the conventional path—graduate from high school, go to university, go to grad school, find a job with a reliable employer, trade your time for money—doesn’t yield predictable results anymore. But even when it does, where does that path actually take you? Fulfilment? Indentured servitude? A necessary but unpleasant compromise?
Maybe, if there is no real security to be found in pursuing the traditional goalposts we’re pointed at, there is no real risk in disregarding them altogether.
Okay, I am aware that I’m approaching this from a relatively privileged position: I have a graduate degree, a dependable partner and educated parents who emphasized happiness over financial stability, I live in a country with a social safety net and a favourable attitude towards entrepreneurship. I’m also not delusional: supporting myself with freelance work comes with extra helpings of normal anxieties about self-worth and ability, not to mention financial worries absent a guaranteed monthly paycheque. But what I want — what I really, actually want at the core of my real self — is not capital or power or security or admiration. It’s autonomy: the ability to say no to everyone and everything except the quiet but insistent voice that comes from deep inside. And for some reason, it’s the one thing that I will make any sacrifice for.
I suppose it’s more like a mindset than a dream or an aspiration. I refer to it as the Wayward Path: there are no fixed long-term goals, there are no guaranteed methods for success — not even a solid definition of what success is. The Wayward Path has no map, only the conviction that following it is its own reward. Its virtues are Self-Reliance, Flexibility, Creativity, Cooperation and Iteration. Its process is imagination, practical breakdown, iterative progress and then a return to imagination.
If you find yourself drawn along a similar route, let me offer you some advice:
Accept that procrastination, disorganization, chaos and existential fragmentation are hazards of life in general and will colour your efforts to establish and maintain an ideal working environment. Realize that you, the creative centre, organizer, manager and auteur extraordinaire, are part of the problem. Even the best, most disciplined humans occasionally degenerate into floundering turds spinning in the toilet bowl of existence from time to time. Circumstances may have you at the centre of your own grandiose hollywood biopic or underneath the heels of unreasonable villains: you need rules and methods that function independently of your fickle moods and the roller-coaster nature of a creative business. You need to trust yourself that even on the shittiest of days, you can depend on the environment you’ve created and arsenal you’ve assembled in order to follow through on your obligations.
Sometimes, you will do well. Sometimes you will fail. They will feel very different but they are the same. Do not let either stem the flow from the bottomless pit of creativity (I call it The Hole) that lives inside you. There is always more, deeper, further. Trust technology / techné, your tools and your craft, to bring to life those inklings that spring up into your conscious mind. But build boundaries, because the world will squeeze you into a tiny corner unless you fight back. Maintain perspective: everyone has their own important shit going on and you are probably not at the top of that pile. (This is a sweet mercy to remember when dealing with multiple clients at the same time.) Feel entitled to cultivate bravado alongside humility, because the last thing you need in your way is a fragile ego.
And when a voice comes to you at night asking what it’s all for, remember: you do it to be free.
