One Year of Freelancing, part 1: The Mistakes I Have Made

To my first year of freelancing… a huge success!

I have been freelancing and writing now for about a year. In that time my skill set has made me wealthy and famous, my name has become a brand, I have no idea what the word failure means… oh, wait, I’m confusing reality with my application to go on The Apprentice. No, I’ve been freelancing for a year, my income has not yet matched the rent I’m paying (I try not to sweat the small stuff such as affording food and paying my bills), all my savings are gone, and I’m currently begging and borrowing (but as yet only contemplating stealing) in order to survive. So it’s been going splendidly.

Even if I didn’t actually want to freelance, what choice do I have (I ask myself rhetorically)? I have applied for several jobs over the past eighteen months, ranging from those where my experience and qualifications were completely aligned with the position, to the most basic jobs that I could have done with my eyes closed when I was 18 (and my eyes would have been closed, so unimaginably tedious were the jobs I was applying for). But I haven’t got close to landing any of them. There’s simply not much place in today’s job market for a man in his 40s, armed only with a PhD, a varied and successful background in academia, a capacity for independent thought and a sense of humour. Perhaps the problem is that I simply don’t get the soul-destroying values of most ‘work’ (which increasingly includes the work of academia and its brave new corporate mentality), the obsession with making profit out of producing meaningless shit, the ‘performance targets’, the valuing of numbers over people and, well, values, the human resources personnel (i.e. the corporate drones whose main purpose is to make employees redundant), the idea that productivity demands putting on a suit and tie and turning up to a dreary office at nine in the morning when, quite honestly, what would truly be productive (i.e. of benefit to the world) would be for me to lie in bed all morning thinking about Descartes and then sharing my thoughts in a blog article… I could rant on, but I won’t.

Fortunately no ‘sane’ employer wants me near a desk at nine in the morning, so I do get to sleep late and then pen thousands of words—the equivalent, in fact, of a couple of books over the past year, all of which have earned me the princely sum of £0.00 (exclusive of my expenses). So this is the life for me, and despite all evidence I retain an almost lunatic belief that it will work. Peer extremely hard and, as I will insist on telling the psychiatrists when they cart me away, grounds for optimism can be detected. One reason for optimism is in fact the mistakes I have made—or rather that I can recognize most of them. So here are the mistakes that I may or may not be repeating as I venture boldly into year two of freelancing/crippling poverty.

  1. Not having a good plan

Although I had long entertained the idea of going freelance, my actual step into it was the result of a neat government trick. There I was signing on as unemployed, for the government one more irritating confirmation of how badly they preside over society and the economy—so they gave me a little incentive to go self-employed, thereby taking me out of the unemployment statistics and saving on the welfare bill. It was dressed up as a scheme in which ‘employment experts’ would help participants to draw up a coherent business plan and get this plan up and running. But I think ‘scheme’ is too grand a word for it. ‘Crap’ would be better, and also a suitable description of my business plan which the ‘experts’ cheerfully waved through.

But I should be fair: I take full responsibility for my poor planning. I had some ideas—a mixture of tutoring, editing and writing—but with no clear sense how I was going to make them work. In part that’s the way of things: we learn through doing. But it helps if there is at least the semblance of a plan to give structure to the doing. As someone who had spent most of his life in a refuge from the ‘real world’ (i.e. in academia), I had little insight or idea of how to formulate a coherent strategy that may actually turn my vague ideas into a viable living. But worse was that the ideas were indeed vague, a sort of ‘I’ll do a bit of this, and a bit of that’ without really knowing much about what the doing and the bits and the ‘this’ and the ‘that’ were. In so far as I had a document headed ‘Business plan’, it should be filed under ‘creative writing’; since it was hard to identify in it either a business or a plan, it was more an invitation to drift aimlessly than a blueprint for success.

  1. Lack of confidence and belief

A bad plan is arguably better than having no plan at all, but not having confidence or belief in it or my ability to carry it out simply compounded its badness. Initially all was well: despite having had the recent experience of being made redundant from a job that I was good at followed by several months of trips to Walthamstow (an experience grim enough in itself) to sign on at the Job Centre (a whole new level of grimness which made me ponder on the happier times of my job cleaning toilets—yes, I have done that as well as give lectures on topics such as the philosophy of Spinoza), I began my life as a freelancer full of hope and joy. I held onto this unfamiliar state of mind for a surprisingly long time (it was a good two or three hours) before reverting to my more typical mentality of doubts and pessimism. And, frankly, one cannot afford doubts and pessimism as a freelancer (actually I could, because I had some savings, but you know what I mean).

Freelancing requires almost single-minded commitment, confidence and belief. I don’t think it is necessary to be quite as deluded in this respect as an Apprentice candidate, but it probably wouldn’t do any harm. Being convinced not only that the path will end in success, but also that you are utterly brilliant at doing what you do—yes, you end up looking like a dick, but who cares about that when the money is rolling in? (Well, I tend to actually, which is part of the problem.)

What happened to me was this. I started questioning whether I was really any good at all the things I wanted to do. I worried about the lack of money coming in. I wasted time and energy on agonizing whether to swap self-employment for regular employment, and more time and energy applying for jobs I didn’t much want (and yet more time and energy on feeling miserable about how my soul would be imperilled if I actually got one of these jobs). I started taking on far too much private tutoring, at the expense of those things such as writing that I really wanted to do and which have more long term potential, simply because tutoring brought some money in (but, as I hope to write in a future article, private tutoring is a dispiriting sector, abysmally paid and involving often demoralizing work and conditions). As my already bad plan started to turn into an even more directionless mess, my belief in my potential as a freelancer further plummeted. Desperately I would come up with ideas, only to panic and abandon them in a fog of uncertainty and despair. Feel free to follow the recipe in this paragraph: if failure is what you want to cook up, then I can guarantee that it works.

Above all, confidence and belief are about holding one’s nerve (for example, not letting panic compromise long-term aims by focusing on short-term work that ultimately yields little of enduring benefit) and being prepared to blunder, to make mistakes and to make a fool of oneself. The latter is especially important: among the wisest advice I have received from a close friend and artist is the necessity of taking risks, of diving in, of not letting the many mistakes and failures along the way distract from the path. All that involves almost total belief both in what one is doing and in one’s ability to do it—and total belief means not questioning whether any of this is deluded.

  1. Lack of marketing strategy and efforts

As an academic I preferred thinking about things such as whether early modern witchcraft can be explained sociologically or anthropologically rather than things such as marketing. But that mentality is disastrous for the freelancer. As I’ve learnt over the past year, marketing is, if not quite everything, then not far off it. You can offer amazing services, have loads of great content, be creating an amazing product, but unless it is marketed properly then little will come of it. Similarly, great marketing will make all sorts of crap successful (and explains why most of the stuff we own is really rather shit). All of that is, of course, obvious—or you’d have thought so.

In so far as I had any marketing strategy it was this. Set up Facebook, Twitter and LinkedIn accounts. Sign into them every now and then. Make contact on social media with people I know. Set up a website. Offer services and produce content that are of outstanding quality. Give away most of this for free or at ridiculously reduced rates in order to expand my potential customer base. (Yep, I’m using the lingo…) Tweet and post updates about it occasionally. Watch as the world quickly catches on to my brilliance.

It was the marketing strategy of someone who was both clueless and overly concerned about the possibility of annoying people.

What I’ve learnt—the insight I’ve gained from the mistake I have made—is that marketing needs to be done continuously, and that it needs to be fairly aggressive (and risk annoying people). Every day I should have been setting aside some time to promoting myself, which would have meant spending more time on social media than I generally care to. I should not have been shy of things that I normally consider ridiculous: amassing numerous followers and contacts; ‘liking’ tweets and updates about cute kittens; telling the world that I have just made myself a coffee as a prelude to writing a new article; sharing, liking and retweeting over and over again; repeatedly updating and tweeting about my own writing until the only way to shut me up is for sufficient numbers of people to read/download/pay for it. For someone whose preferred mid-morning activity is to lie in bed with a cigarette while reflecting on the beauties of anarchism or the merits of existentialism, spending that time instead in the less edifying milieu of social media does not come naturally. But it is essential.

So those are three mistakes. I have given this article the hopeful designation of ‘part one’. That means it may be followed by a ‘part two’—in which the intrepid and now penniless freelancer explains why, all these mistakes in year one notwithstanding, year two will be a story of success and glory. And that depends on whether, by the time I write the second part, I have got a plan, one in which I believe and have confidence, and one for which I have a marketing strategy.

It all comes down to one of the questions that historians occasionally ask: do we learn from the mistakes of the past, or are we doomed to repeat them?


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