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. 

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?

Tags: Freelancing, Janus, pushmi-pullyu