One Year of Freelancing, part 2: Reasons to be Cheerful

In my previous post I outlined various mistakes I have made as a freelancer over the past twelve months. The road I travelled over that year began in a place called Hopes and Dreams and ended in a place called Desperate Poverty. Except, of course, it hasn’t ended, because I can’t be hanging around in Desperate Poverty for too long. Much as I’m attracted to the romantic image of myself as the penniless, starving writer, my cigarette the only source of sustenance and warmth as I give to an uncaring and uninterested world the fruits of my mind and craft, I realize it’s important not to be an idiot.*

I could, of course, go to a place marked Regular Job. It’s a safe, ordered sort of town for most of its residents—and, sadly, one of the least interesting places in the universe. Moreover, there is nothing much there for me. I am frankly unqualified and unsuited for most of what it has to offer. The only profession I am qualified for is academia. (And yes, I’ve heard and reflected on all the motivational talk from careers’ advisors etc. about the supposedly transferable skills I have—and it is rubbish. Short of spending years and thousands of pounds retraining, or competing with hungry young graduates for internships and entry-level jobs, there simply is no career for which I have any realistic chances.) As for academia itself, although I do actually still have a miniscule, meagrely remunerated university post, it was clear to me long ago that academia is not interested in me. I’m just too damn unconventional and brilliant (oh, yes! I say with my tongue firmly in my cheek) for the increasingly mind-numbing corporate world of academia. I loved my academic career and didn’t want to leave it. But looking back I have no regrets that I did: if I’d wanted to be a corporate drone, working 60 hours per week, oppressed by admin, metrics, endless performance and productivity reviews, and exploitative employment practices, then I’d have joined the City years ago and earned considerably more than the dismal salary of the modern lecturer.

A few weeks ago I made the decision to abandon for good any ideas of a return to academia. I suspect that half my problem over the past year was my wavering between the freelance path I was on and a desire to get an academic job. By not fully committing to either, I ended up being unsuccessful in both. I had to reassess, and, for the reasons I mention above, I came to realize that academia no longer appeals to me whereas freelancing does. I retain my interest in ‘academic’ things (like history, philosophy and so on, and indeed the nature and purpose of education itself), but I’d rather pursue them independently and in my own way—and since the modern humanities academic is usually preoccupied with filling in forms and worrying about productivity, most have little opportunity to pursue their subject in interesting ways. (Not that I want to give the impression that I’ve got a chip on my shoulder…)

Saying goodbye to academia for good is my first reason to be cheerful. It means I can direct all my energies and focus to the freelancing. And with this energy and focus comes more clarity. I recognize the mistakes I made, the wrong turnings I took, how I never had much control over what I was doing, with the result that it tended to drift. For example, tutoring initially struck me as a sensible option, one that aligned with my experience, skills and knowledge, and which fitted with my vague hope that I would get back to lecturing one day. But I learnt that private tutoring is a terrible sector—and not one for which I am well suited. (I don’t believe, for example, that education equates to ‘teaching to the exam’ which is essentially the only thing most tutees want from their tutors.) While I am open to taking on the occasional tutoring job, I’m going to be highly selective about what I do. If I am especially interested in a job, and believe that I am suited to it, then I’ll do it; but otherwise private tutoring no longer features much in my plans.

Since I’m in danger of sounding like Ian Paisley in saying ‘no’ to everything, it’s time for a ‘yes’ (and one or two more reasons to be cheerful). And it’s a ‘yes’ to writing. I’m a writer. It’s what I’m good at (feel free to disagree, but if you do, you’re obviously wrong because I’ve held your attention to this point in the article which means the writing is working), it’s what I enjoy doing, and it’s what I’m convinced I can make a living from.

Now, this is a blog article not a business plan. But it’s worth (since it’s cheering) to consider the nature of writing as a business—as I have been doing over the past few months. Every day billions of words are written and published, in the form of books, newspapers, magazines, web content, blog articles, and much more. Some of this is published for free; much of it earns the writer money either through direct sales or by carrying advertisements. It is a huge market.

So if you’re someone who can write well, as I can (feel free to disagree, etc.), then there is massive potential to be successful in this market. Above all, the digital revolution has transformed the possibilities for the writer. Blogging and self-publishing form an ever-growing chunk of the market; they are a large part of the future of publishing. In the past writers were often at the mercy of the whims of traditional publishers. Now anyone with something to write about (and boy, do I have a lot to write about), the ability to write it well, the time to write it, and the nous to figure out how to market and sell this writing has a decent chance of success. The extreme example is E.L. James, whose Fifty Shades of Grey trilogy began as self-published fan fiction and ended up netting her £97m (and counting). While James is clearly an outlier, many other writers are making a decent living in this world—and a growing number are actively choosing self-publishing over traditional publishing. And, while not abandoning other routes to getting published, it is the world of self-publishing that I’m entering.

I have, in fact, been self-publishing for quite some time. Over the past year I’ve written a lot across various blogs, and, partly out of generosity, partly out of business incompetence, I’ve given it all away for free. Actually, there are good business reasons for giving things away for free, and I certainly don’t intend to stop blogging and providing free content. But the point is this: writing is a business. It’s a business like any other: writers create and market products with a view to selling them. One of the reasons why I’m cheerful is that I’ve finally got my head around this; previously I treated writing too much as if it were a hobby, one involving the devotion of hours of my time to giving people something to read while I slowly starved—it took me a while, but eventually I detected a small flaw in that approach.

Another reason to be cheerful is that, having been studying this market for some time now, I’ve figured out various approaches and strategies that I believe have good chances of success. Maybe I’ll blog about them one day… But finally, and most importantly, I have various products (some under pseudonyms, which doesn’t mean that I’m going down the E.L. James route—or maybe I am?) that will be going to market soon. But you’ll just have to rein in your excitement at this development for a little longer…

This time last year I had a lot of optimism, but a terrible plan. Because of the latter I’ve ended up on the brink of destitution. It’s been an interesting lesson: optimism is important, but ultimately useless without a good plan. I believe now that I have a good, credible plan. I may be able to afford to buy food again. Hope endures.


*Knut Hamsun’s fine novel, Hunger, the story of a starving (and increasingly mad) writer is well worth reading as a corrective to this romantic notion of the artist/writer.

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

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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?

Hope, Experience, and Efficient File Management

It’s that time once again when hope joins battle with experience: the start of a new academic year. This year, I tell myself (as I have told myself every year since time out of mind), I shall be organized like never before. There will be no more coffee-fuelled all-nighters to prepare lessons; no more hours lost tracking down an old lecture to find it filed in my Music folder; no more staring blankly at my diary unable to decipher the name of the student I am supposed to be meeting; no more panic on an unmoving train because I have left a margin of error of less than a minute to arrive at a meeting. I will be a lean, keen teaching machine, gliding through preparation and lessons with elegance and efficiency, with plenty of time to write and research productively. I may even make some money at last.

If hope is outpointing experience by Christmas then I will be doing well.

First I need to find my desk. That involves hacking a path through piles of books and magazines to the area of my room where I last remember seeing said desk, and then excavating through the papers, unopened bills, junk mail, long-forgotten invoices, receipts, post-its, pens, pencils, paper clips, elastic bands and sundry miscellaneous items to what I believe will be the desk itself. Treasures, in the form of untouched Rizla packets, are likely to be found during this archaeological dig. All of this reminds me of how once, when I had an actual office in an actual academic department, I would advise students on the merits of efficient organization, advice delivered across a scenic landscape of mountainous chaos on my desk.

Then I need to sort out my computer desktop. Unlike my physical desk, upon which no organization at all can be detected, my computer desktop suffers from a worse state of affairs: a half-hearted semblance of organization. Clearly at some point (probably the start of the last academic year) I devoted a solid half hour of attention to this task before being distracted by a book that needed to be read, never to return. There are folders, inside many of which are further folders and files that logically belong there. Keeping them company are many other folders and files whose rationale for being there would surpass the wisdom of God. Different versions of my CV crop up incongruously in various locations as if it is a self-replicating, mutating virus.

Finally, emails… but that will surely, as always, be a task too far. (Ah, experience strikes an early blow against hope…)

I’ve come to realize that when it comes to organization I should either have none at all or a complete, fully worked out and implemented system. The virtue of the former (my preferred approach for many years) is that I became adept at storing relevant and important information in my head. It did not matter that a letter containing the time and date of an appointment was hopelessly buried beneath any one of several piles of papers, nor that I did not write down appointments in a diary, for I had already committed this information to memory. This non-system almost never failed. Problems arose when, having been foolishly seduced by the time-management and efficiency gurus, I introduced some formal systems of organization. Because I was never organized enough in the first place to introduce organization in the proper way (the fatal flaw afflicting these systems among the irredeemably disorganized), I ended up with a hideous hybrid, a jerry-rigged mishmash of systems and memory. So, some appointments ended up in my diary, and some were committed to memory—others ended up both in my diary and my memory, while others (the majority) ended up in neither.

The trick is to get beyond the overwhelming feeling that bureaucratic systems and organization suck the life out of existence, and to overcome an intuitive resistance to the idea that hope can only be realized by efficient organization. Are dreams really built on time management and effective filing systems?

The Festive Freelancer

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Merry Christmas! (Billy Bob Thornton as Bad Santa)

Spare a thought for many freelancers and self-employed at Christmas. A good friend of mine whose entire career has been spent in self-employment has always been unfailingly curmudgeonly at this time of year. I had never understood his loathing of Christmas. Sure, there are numerous annoyances (which do seem to accumulate as one gets older), but on the whole I always liked the idea of an extended and shared holiday season—a chance to catch up with friends, drink too much, party, read, sleep, the last of these probably being its greatest boon. What is not to like? Well, for a lot of freelancers, as I’m beginning to learn, plenty.

The biggest problem is that income dries up. Of course this doesn’t happen to all freelancers—it’s a good time of year to be a freelance Father Christmas, for example, so that’s an idea for a future revenue stream (but only if I could do it in the style of Billy Bob Thornton in Terry Zwigoff’s fine festive movie, Bad Santa). But for a lot of us, from about the middle of December until the first week of January, work becomes at best a trickle. Companies are more focused on planning the office party and the festive shutdown than they are on contracting writers, designers, developers and artists (note to self: freelance party planning as a possible business idea). Certainly the self-employed plumber stands a chance of landing a lucrative festive job as somewhere a boiler gives up the ghost on Christmas Eve, but the self-employed private tutor is holding out little hope that anyone will be making an urgent request for an A-level history lesson on Boxing Day (another note to self: HND in plumbing as idea for 2015?).

So the days pass without any money coming in—but a lot of it going out. That’s one of the biggest downsides to freelancing: the salaried employee not only gets to take guilt-free holiday, but is even paid to do so; for the freelancer, however, time off work is time not earning money, and when that time is spent drinking Buck’s Fizz, eating Quality Street and buying novelty Christmas socks as gifts then it involves spending the money that is not being earned. So what used to be the good things about the festive season—puffing on cigars and drinking lots of whisky being highlights—now turn out to be not so great after all; and all the bad things—engineering works on the railways, revellers with reindeer hats throwing up in the street, and, of course, the indescribably horrible experience of having to do a lot of shopping—just seem even worse.

Another downside to freelancing is that sickness, like holidays, is not paid for. And at some point during the winter I’m bound to catch a cold. Now is therefore the best time of year to do so, getting it out of the way while I won’t be earning money anyway. So that’s what I’d like for Christmas: a common cold, nothing too serious (I’m not expecting anyone to splash out on it), but quality enough to ensure I won’t be getting another one for many months, and ideal for re-gifting. Glad tidings of great joy indeed!

The Way of the Ronin

Once upon a time, provided you had the money, some knights could be hired for pay. They were the original freelancers: possessing a horse and a lance, and with no bond of loyalty to a lord, they were free. In feudal Japan the equivalent was the ronin, the masterless samurai famously depicted in Akira Kurosawa’s films Seven Samurai, Yojimbo and Sanjuro. The direct modern descendent of the knight-for-hire and ronin is the mercenary. But as I sorted out my purchase and sales ledgers yesterday evening, I romantically imagined that I too was part of this tradition. The knights and the ronin probably spent little time searching for mislaid receipts and invoices, but as free men offering their extensive skills in an open market are they not my spiritual ancestors…?

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What I’ll be wearing when completing my tax return

Well, probably not. But it’s a thought worth holding onto when I have to complete my tax self-assessment form. And I am drawn to what might be termed the freelancing philosophy. At the heart of this is the idea of being bound only to oneself, of being free. Being bound to a lord (or employer as we know them these days) is an uncertain business. Some are great and will value both you and your work; others, no matter what excellent service and loyal, even self-sacrificing, commitment is given them, treat you as little more than a figure in their budgets and will terminate the bond without even so much as a farewell. Far more appealing is to work for yourself, since you will be hard pushed to find anyone who values you or your work as highly. Of course, there are still budgets to worry about, but at least you will value yourself enough to want to continue employing you.

So one reason for going freelance is to step out of the occasionally ruthless, devaluing world of working for an employer and to step into the always caring, valuing world of working for oneself. That may sound like a negative reason—surely freelancing is a viable choice not simply because the alternative is generally worse? Indeed, to become a freelancer should be seen as a wholly positive decision. In my case it was a choice that I had long been drawn towards but had lacked the confidence, or what I thought to be the right circumstances, to venture my first step along this path. Recently, however, everything seemed right to make a go of it. And now, having advanced a few paces, I’m determined to keep going—for there is so much to love about this journey.

I love the feeling that (HMRC notwithstanding) I make the rules of my work. I can try different things, explore new directions, knowing that I am answerable only to myself for my decisions. If I have an interesting idea for a project I do not need to seek the approval of an employer to start working on it. I can freely pursue leftfield ideas. I have flexibility when it comes to choosing among the opportunities which come my way, and can focus on areas that I am passionate about. I have greater control over my time, and am able to allocate it throughout my life in ways that are meaningful to me. I am responsible for my success and failure—and that’s quite a motivation for devoting energy and effort to ensure the former.

Of course, freelancing is far from easy. I’ve only just begun this new life and quickly I have realized how much there is to learn. Marketing and networking, accounting and tax returns, balancing time and money, pitching ideas and experimenting with projects, and learning (as the medieval knight must have done) about getting back on the horse again whenever you fall off. I foresee numerous challenges and uncertainties ahead—which is precisely what the knight and ronin would have relished about the quest.