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The contradictory world of the freelancer

From the outside, freelancing must look pretty romantic – lie in bed until 11, work in your underpants and shave once a week. And, most of the time, it is exactly like that. But there are times that rip the ‘free’ right out of ‘freelancer’, leaving you with nothing more than a lancer – which, as we all know, is a type of cavalryman who fought with a lance. 

Lucky old Janus could admire the key to the new year and watch the darts at the same time
Lucky old Janus could admire the key to the new year and watch the darts at the same time

No, scratch that. What I really meant is that there are times when the good things and the bad things about freelancing end up balancing each other out in an intriguingly complicated way. So here are a few observations on the Janus-like, pushmi-pullyu world of the freelancer – so much more conflicted than you thought…

  • Insecure yet secure. As a freelance, you never know where the next job is coming from, making your income profoundly unreliable – on the face of it. But, once established, you can build up a client base that is varied in terms of sector, geography and organisation type, and that diversity constitutes a kind of security. The employee, by contrast, is a hostage to fortune, dependent on one company’s success.
  • Senior yet junior. If you’re a freelancer with a few years on the clock, you can often find yourself being briefed and managed by those with far less experience. But your role is always to take direction, never to give it. You may have to bite your tongue when asked to work with approaches or timescales that you know from long, hard experience simply won’t work.
  • In control, yet constrained. The appeal of the oft-discussed ‘freedom to control your workload’ soon fades when you realise that controlling your workload means declining work. So who are you going to turn down? Will you risk alienating a longstanding client, or nipping that potentially fruitful new relationship in the bud? If anyone (including you) depends on your freelance income, saying ‘no’, in practice, takes some nerve.
  • Sincere yet manipulative. As a freelance, you often find that work contacts, and even competitors, become friends. Many clients jump at the chance to confide in a knowledgeable outsider with no political axe to grind. But when friendship and work overlap, it’s hard to be sure of your own motives. Are you paying that compliment from the heart, or because the recipient could hook you up with some work?
  • Rich yet poor. Unlike most professional employees, the freelancer can ‘turn up the machine’ by adding extra hours into the day that are actually rewarded with cash money. As a result, it’s possible to boost your income quite significantly. But because your future income is always in doubt, it can be difficult to pluck up the courage to spend the spoils. 
  • Unfettered yet beholden. One of the best things about freelancing is being free of the tie to one company, or the obligation to work with one boss. But freelancing isn’t retirement. Instead of being under one big thumb, you’re under lots of little ones – dancing to the tune of all your clients at the same time. And it doesn’t always feel that much like freedom.
  • Lonely yet connected. You’ll probably spend a lot of time alone as a freelancer. Depending on your character, that might be a plus. However, in my experience it’s particularly tough to take setbacks such as high-quality proposals that are ignored, highly regarded clients who defect and high-value invoices that are unpaid – all on your own. On the other hand, social media lets you build up an extensive network of people in just the same boat.

Is it all worth it? Well, it’s not for everyone. But if you can handle an unstructured day, motivate yourself and do without the lure of ‘career prospects’, I think the pluses outweigh the minuses. Now, I wonder if I should get out of bed?

Comments (12)

  1. Interesting points Tom. I’m addressing them all in my next book. As you say, it’s not the life for everyone, but when it works, boy does it work!

  2. Really interesting read Tom. Thank you. You’ve captured the conflicting positions brilliantly. I feel your pain! I’d also second Andy re. the benefits being fantastic if freelance life is a good fit for you. There are so many pluses to this way of working. When I go back into agencies and do the occasional in-house day, I notice them even more.

  3. I’d also say that as you become more experienced, your clients can become more senior along with you. These days I am often working directly for MDs, CEOs, directors and “heads of…” rather than marketing execs. Not always, but mostly. Anyway, humility is a wonderful thing!

    Positioning yourself as an expert also gets you listened to more.

  4. I think people need to realise the amount of business management involved, too.

    A lot of people just dream about spending all their time doing what they love – and don’t realise how much time as a freelancer they’ll also have to spend on the various administrative tasks, on accounting (even if you have an accountant, there’s always the joys of invoicing), on customer relations, etc. As an employed copywriter, they wouldn’t have to worry about these tasks.

    On the other hand, it really does make you a lot more organised by default and gives you a better understanding of how all these elements work best together.

  5. The life of the freelance is becoming increasingly attractive to me as I struggle with a life of ‘office politics’… but I think people underestimate just how much work goes in to building it up from scratch – some excellent points, thanks!

  6. Thanks to everyone for the comments.

    Rowena’s quite right to point out the administrative/business side, which could easily take up 20% of your time in some weeks – particularly if you include marketing tasks (and blogging!).

    I think it’s a real strength of the freelance copywriter that they can talk to clients, particularly SME clients, as a business owner rather than an employee. A couple of years’ freelancing provides an ideal education in cash flow, turnover vs profit, client relationships, marketing and a host of other issues that SMEs lose sleep over. As a result, the freelance copywriter is very well placed to understand the priorities of the SME client.

    Sally – you’re right, it does take a lot of work. I was ‘lucky’ in that I was made redundant, and simply had to get it sorted if I was going to work freelance. I’m sure it’s a lot tougher to make the decision to jump ship, unless your job is truly awful. As the saying goes, ‘when it’s a must, you’ll find a way’.

  7. I love this post and its list of dualities describing freelance life.

    Related to “in control, yet constrained” and “rich, yet poor,” I would add “boundless, yet limited.” As sole-proprietor creative workers, sooner or later we face the dilemma of “scaling” business. The possibilities are, ostensibly, endless.

    Yet an experienced freelancer’s work isn’t replicable. Unless we sub-contract creative work–doable, I suppose, but tough for a number of reasons–it’s very hard to expand business.
    .-= Lorraine´s last blog ..“Linchpin” by Seth Godin-Review by MarketCopywriterBlog.com =-.

  8. Very, very true. You could add a couple more:

    Versatile yet unemployable. After a whole career being my own boss, I know a lot of things, I have many skills and there are lots of jobs I could do really well; yet I’m pretty sure no employer would hire me as an actual full-time employee because seeing so much self-employment on a CV scares them. To them, I would look too independent-minded, challenge their authority and have more willingness to walk away from a bad job.

    Sane but crazy. It’s very rational to be self-employed if you can make it work; there genuinely is more freedom, money and self-respect in it. But some of the stuff we have to put up with defies belief. I’m pretty sure that any wage-slave would find aspects of choice completely insane. No paid holidays, no cover if you’re not working, feel sick? tough, get on with it, training – what training?, no promotion and no pay rises for doing nothing new.
    .-= Matthew Stibbe´s last blog ..It’s not rocket science: 100 rules for NASA project managers =-.

  9. Great post Tom. I’d also add Focused yet Distracted. Even for the hardest working freelancer, spending one’s downtime (some of it, anyway) to market, blog, tweet, network etc can go against every slothful bone in one’s body (as he writes from the couch… watching Wimbledon.)

  10. You just described my new career move in one fell swoop. It’s not an easy road, that’s for sure.

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