The Human Freelancer

Happy and honest self-employment for conscientious newcomers

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If you’d prefer these pearls of wisdom and vitriol to be poured directly into your brain, watch this audio/slide video of the same presentation. If you’re wondering what the hell this is all about read this.

Almost 15 years ago I was where you are now – bright eyed, feeling pretty good about my degree, ready to make a mark on the world with my talents.

What actually happened was I woke up in the twilight of my twenties, an injection-moulded, 9–5 corporate drone sleep-walking into the grey wilderness of middle-management. Aged 28, the highlight of my month was collecting a salary then spending it on shiny crap I didn’t really need.

Because success is wearing a suit and hating your job, right? Moaning about never having enough time or money. Then taking up golf so you can get away from your fat wife.
Well it doesn’t have to be that way
You don’t have to do what everyone else thinks is respectable and correct. Instead, you CAN listen to that little voice inside saying you’re meant to be your own boss. You CAN earn a living doing what you love.

So I’m here to sell you freelancing, which is more than a career – it’s a way of life. And life should be about fulfilment, happiness and living responsibly.

In this session we’ll explore whether it’s right for you, what the freelance lifestyle is like and how to get started. When we’re finished here I’ll hopefully have sped up your transition to freelancing or at least convinced you there’s a lovely, alternative way to spend the rest of your life that doesn’t involve debt and arguments.

At the end we’ll pretend you have some questions for me but everyone can just sit in silence and stare. Sound good? OK.

Is freelancing right for you?

Yes it is. Obviously. It’s brilliant: no question. Who doesn’t want a life without alarm clocks, to make an honest living using your talents, meet new people, learn new skills and do something different every time you go to work.

Anyway, more of that later. Right now there’s a more pertinent question: are you right for freelancing? Because there’s a certain type of person who takes to it more naturally.

The type of person to whom freelancing will come more naturally tends to be quite independent. They’re free-thinkers which is probably why they never quite get on with authority figures, especially if they think they can do a better job than their boss. They’ll quite happily get on with things in their own time because they’re organised and can motivate themselves to do things. When they make a promise they stick to it because they hate letting people down – they’re very honest and principled. People sometimes say they’re the type of person who could turn their hand to anything, whether it’s computers, baking, DIY – whatever they just seem to be quite handy.

My wife told me off for writing something as prescriptive as this because she thought, ‘oh you’ll upset those poor students if you crush their dreams by telling them they’re not fit for freelancing.’

What I’m trying to say is that freelancing isn’t for everyone and some people are more natural at it than others. But don’t worry if this doesn’t sound exactly like you – I’ve met some real arseholes who do quite well for themselves so there’s hope for you yet.


Freelancing demands a lot of courage too. People will tell you you’re brave to snub salaried employment and go it alone, when in fact turning your back on conventional employment is actually really easy, because it’s rubbish.

The hard part (and you’ll find very little support for this) is that freelancing is very emotionally demanding, it can be lonely and it really tests your self-esteem. So to get the most out of it as a career it really helps to quite self-aware, and ready to learn and grow as a person.


Note that you don’t have to be a ‘creative genius’ to freelance. It’s all very well being a tortured visionary but if you don’t know how to relate to people and prefer living in a basement full of prawns you’re no good to anyone.

I know one guy who makes a living out of basically making people feel good about themselves on teleconference calls. Yes – you can make a living out of being a people-person.

What the freelance lifestyle is like

Here’s a typical day: I’ll get a call out of the blue from someone who’s heard about me and likes what I do. They’ll invite me to collaborate with them, I get to learn something new, make new friends, then write about it (or photograph it). When it’s finished they pay me money, tell me how pleased they are then ask me to work with them in the future and tell all their colleagues.

You get to do awesome jobs like this one I did for Ecology Building Society – photographing sustainable eco-buildings, meeting the people who live in them, eating free pizza and travelling to beautiful, remote, parts of Scotland and Devon.

Then you get other jobs which are total shit. Like this one I did for a well-known regional development agency who basically wanted me to write what I was told – really dull corporate bollocks about economic growth targets, it was essentially an open invitation for huge multinational tax-dodgers to come and gang-rape Leeds. I got so stressed and poorly doing that job. It was awful.

There’s a reason I chose these two examples, because it’s only during the highs and lows that you learn stuff about yourself. Yes, full-time salaried employment provides ample opportunities to get depressed and ill, but it lacks the variety and freedom, as well as the highs that freelancing brings. This is what I mean by the spiritual side of freelancing – because living a fulfilling life is all about new experiences and going outside your comfort zone.

Remember, freelancing is a way of life. Full of variety, empowered personal growth. And best of all you’re in control. Everything you do is your choice, not just in your free time, in your day job, every day.

Your job role changes too – that idea you’ve got in your head right now about what it is you might do: it’ll be radically different a few years from now, I guarantee. Getting fatter and picking up your salary every month isn’t living. New challenges everyday on your own terms is.

How to get started

Get a shit job. Yes that’s right – despite what I said earlier.

Do a few years hard grind – ideally at a large institution so you really feel what it’s like to be a very tiny cog in a very large machine, where all your days bleed into one, stumbling from one meaningless action to another, each of less consequence than the last.

I suppose there’s also some merit in seeing how spectacularly inefficient the gears of British commerce really are – that way you can see what needs fixing by a diligent freelancer like you.

So there really is no better way of truly appreciating just how awesome being your own boss is than doing shit jobs.

Foster self-belief

I wrote a chapter about this in my book. It basically says you have the right to call yourself whatever you like. I’m not talking about pretending to be a doctor or judge or anything because that’ll get you in lots of trouble.

What I mean is when someone asks what you do, you have as much right as anyone else to say you’re a freelance copywriter, graphic designer, biscuit detective – whatever. It doesn’t make you a fraud to call yourself that from day one. It took me a while to feel confident enough to call myself a copywriter, I’d skirt around the issue by mumbling about writing, but eventually I realised most people are quite trusting – they accept what you tell them at face value, in fact often they don’t really care. What really matters is talking with conviction and passion about what you do, that means more than whatever label you attach to yourself.

I brought this up because one common mistake everyone makes is to go hunting for courses to make yourself feel better about ‘not being qualified’ (notwithstanding that some professions do require certification, like doctor or judge).

I say just go for it. Learn as you go along if you’re not entirely sure. Paying money for a course won’t fix your lack of confidence. Getting on and mastering something will.

Most freelancers I know learn on the job: when a client asks you to do something it usually involves lots of other little bits you wouldn’t usually know how to do. So you go and take a look at whatever it is and weigh up whether it’s worth having a crack at. You do it, then chalk it up on your little list of success stories.

Like, I’m here in my capacity as a highly-experienced freelancer. You believe that, probably because I sound convincing. No one’s ever asked to see any proof of that. I could be a right deviant, maybe I am – just making this all up as we go along. Who knows…

Finding work

There’s loads of dispiriting advice about finding work so I won’t cover old ground. What works for me is doing a good job for clients so word gets around, keeping a lively web presence (blogging, tweets etc.) There’s really no secret to this, despite what people tell you: it’s all word of mouth so be nice to people, be genuine, ask questions and explore what you’re interested in anyway – you’ll pick up work as you go along. Volunteering for charitable causes is how I started, maybe look into that.

Let me reassure you: after a couple of years freelancing, something ALWAYS turns up. It’s really weird but you work finds you through the weirdest, chance encounters you can possibly imagine.

A freelancer friend of mine, one of his biggest clients is an old neighbour of mine from Harrogate. What he doesn’t know is the only reason we got chatting was I left the toilet window open while I was having a sit-down interlude. I’d turned round to locate the toilet paper and my face met my neighbour below, and we got into a nice, long chat about how he was a publisher who needed a web designer. So I basically won some work for my mate stood with my pants around my ankles.

So the rule is you never know where a conversation will end up. And it really really helps not to be a dick to people.
Less money means less pressure and less work
When it comes to designing a life with less work, conventional wisdom says you have two options. You can either work hard for a short while, save the money then eventually work less, or you charge more for what little work you do do.

Intense, hard work for short periods sounds like a death sentence to me, and generally speaking, once us humans get a whiff of financial rewards for hard work we tend to get greedy. Then before you know it you’re lost in a downward spiral of spending to compensate for your loss of free time and energy. And that completely misses the point of what we’re trying to achieve here anyway.

The second option (increasing your rates) is a bit cheeky. It’s not fair to make other people to fund your lifestyle choice if you’re already charging a reasonable amount for your time and effort.

The quickest, easiest and most empowering way to work less is to liberate more of what you already earn by reducing your outgoings. You also instantly reduce the need to work as much, as well as the pressure to earn.

There is no secret to it. It’s just simple prudence and a few simple changes like eating less meat, or using public transport which save you so much money.

If you go into freelancing to get rich then you’re coming into this for all the wrong reasons and sadly we can’t ever be friends.


I wanted to mention this because one of the early stumbling blocks you’ll encounter is working out what it is you offer. Again, all those dull books on self-employment will teach you to ‘identify a market opportunity’ or ‘capitalise on a marginal gap in the marketplace with maximum profitability’.

Trying to fit your creativity and eclectic talents into a commodity product that people can pick up off the shelf is a recipe for personal misery. Besides, not one client has ever came to me and said “I’ve got a completely standard job for which I want completely standard copywriting”, it doesn’t happen – everyone thinks their project is unique and needs a totally bespoke service.

A more fulfilling way to look at marketing yourself is think about what you enjoy – what are your hobbies, what did you love doing when you were little? Then work out how those skills are useful, or transferrable to different industries.

Don’t compromise on what you want to do with your life – yes you won’t be a millionaire anytime soon but you’ll be happy and eventually attract more of the kind of work you’re naturally good at.

Recap & finish

So there you have it. Hopefully some of that bilge resonated with you. If that person I described earlier (basically a stubborn anarchist) sounds like you then you’re already halfway to getting the most out of freelancing, but do a few crap jobs first so you really appreciate your freedom later.

I’ve described the wonderfully smug life of a freelancer: work less, do more of what you enjoy. Who doesn’t want to do that? And in case you’re wondering yes I have a mortgage and other grown-up responsibilities but why let them get in the way of having fun? There’s no such thing as work-life balance, only life and your career is a huge part of that so why be miserable all the time?

You might need to do some boring stuff like learn about tax and law but it’s really really important that you foster belief in yourself and learn to listen and trust yourself. There’s no performance reviews or sick pay when you freelance so you have to look after your well-being: yes, push yourself but remember why you’re getting into this in the first place: to do what you love.

Done properly, self-employment is a journey of both good and bad experiences where you grow as a person and learn more about yourself than you ever would smashing your head against a desk in an office.

The Human Freelancer book

LOOK! There's a book full of this shit and more!

Self-help business books perpetuate the myth that success is relentless growth and more of everything means progress. They preach about bookkeeping and market research: things you might need to do of course. But let’s face it they’re fucking boring.

The Human Freelancer book is your antidote: stuffed full of emotional support and insightful advice for vulnerable newbies to self-employment like you.

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