A beginner’s guide to freelance mistakes & how to avoid ’em

Iona Bain


This is what I shout every morning, ala Mel Gibson in Braveheart, when I leap out of bed, skip down the stairs to have my first kale shot of the day, dance over to my laptop and tappity tap tap for a few hours before I go swimming with dolpins, freebasing off a Corfu cliff-top and honing new platitudes to publish on LinkedIn.

That’s what some misguided souls believe freelancing is like (although TBF, the LinkedIn thing applies to any fool with too much time on their hands in the office).

Yes, freelancing should be about having total power over your time and micro-managing your career *just* as you would like it to go so you can do enjoyable and interesting things with your life.

But the bland euphemism of “challenges” doesn’t do justice to the rage of wrestling with intermittent broadband connection, the existential dread of not getting enough work, of failing to head in the “right” direction (whatever that might be) or at least failing to head in that direction quick enough to keep up with those scary people who seem to have Twitter implanted as a chip in their brain.

The truth is that a typical day in the life of a freelancer is…well, there is no typical day. Sometimes, I don’t know where I’ll be and what I’ll be doing from one week to the next. Even as I write this, I may be asked to take part in a series of TV debt reports next week. Or I may not. I may be seriously considering scaling up the Young Money Blog with an interested company one week, dismissing it as an irrelevant side-goal the next. The satisfaction derived from a job well done, of spending one more day doing things on my terms (relatively speaking), of having time to dream and live…this is beyond precious and never to be forgotten in the face of too many conflicting pressures, too much solitude and not enough “validation” from the  world.


Freelancing is tough AF. Not going down the mines, working in call centres, switching off the life support machine tough. But tough in its own, strangely worthwhile way. The toughness – the complexity and richness – is possibly what makes it so masochistically appealing.

It’s the feeling that you can “progress” in a deep, well-rounded way. You have the space to learn what you need to learn and make the journey you need to make. You can thrive, then go off the boil, possibly lose the plot for a while, then make a comeback as spectacular as Craig David’s. It might be stressy, but compared to a sterile office job, it just feels more alive. More real.

But if you didn’t learn from bad experiences, you would just be going round the same track, over and over again, reliving the most nightmarish aspects of being a freelancer without ever enjoying the wonderful and liberating upsides. Well, no more. In case you’re heading down this alley, imma do you a fava.

Here are the biggest mistakes I made in my early days of being self-employed. I splay these boo-boos across the interwebs for no reason other than…if someone had told me this when I first started, I’d have been super grateful. Pay it forward and all that. Here we go.

Error 1: You pick the wrong business for you

You try to fit a square peg in a round hole, and you come out with a very chipped peg and an empty hole (err, let’s move on…)

You have to understand what you’ve got to offer – your skills, knowledge and experience – but also what suits your temperament. Okay, none of us will find the perfect job or client, but the work we do has to suit our personality and strengths. For instance, I hate doing the same things over and over again. I need to find new topics to write about, new approaches, new channels, new goals or I get bored and rebellious. Months spent doing work that you find neither enjoyable nor do-able will wear you down and make it all the more likely that you’ll quit prematurely, all for want of a more targeted and discerning approach. You need to set aside a few hours a week to make approaches to the kind of clients you’d ideally want – don’t just rely on people knocking on your door, no matter how many there are or how “flattering” it might be to get those knocks.

Error 2: You go for bad boy clients


You get hit on by a new client, they woo you with a great chat-up line, you get into bed with them and then…they never call you again. Which isn’t so bad – not all jobs will turn into long-term relationships – but what if they don’t pay you on time? Or if they keep changing their brief so as to make you work longer than is reasonable? Or the ones who abuse, belittle or undermine you whenever you communicate with them? This may initially seem like a price worth paying to get work but in the long-term, you’ll become severely demoralised.

Doing work for unworthy clients never pans out well. It’s a two-way street and you have every right to walk away from a prospective or ongoing client if you have a bad feeling (subject to the terms of any existing contract you’ve signed).

Error 3: You get railroaded into free or underpaid work

Once, I was in contact with a PR who represented a City superwoman. He wanted me to chair several sessions at a conference he was organising. It was unpaid, but he was prepared to offer me expenses to make a “generous” exception. I said I was interested, but would need to think about it. Chairing is a surprisingly niche skill and requires time-consuming preparation. Imagine my surprise when the programme for the conference turned up in my inbox and I was confirmed as the chair for several sessions. I expressed my confusion to him, having never agreed to such a commitment, only to be told that I couldn’t pull out because it would cause a good deal of inconvenience. I told him (politely) where to go.

I’m not saying you shouldn’t do pro-bono work at all. I sometimes chair conferences or write articles/blogs for free (nearly always if a charitable organisation is involved). But it depends on the effort involved and the return I would get in publicity, goodwill among key contacts or industry credibility. You should never work for free if someone else is doing the equivalent work for payment, or if you suspect you’re being roped in as a pliant youngster. Anything coming from a commercial organisation that doesn’t immediately mention price or at least explain why they can only pay expenses immediately raises my hackles.


Error 4: “Just slide the pizza under the door, Mary”

Do you remember the sitcom Third Rock from the Sun? There is an amazing episode from 2000, where alien-in-disguise Dick (John Lithgow) discovers the internet and gets completely hooked. He starts teaching his university classes via a web cam and eventually ends up glued to his computer day and night, prompting him to tell his colleague, Mary, to “slide the pizza under the door” so as to avoid interrupting his web binge.

Sometimes, being a freelancer can be a bit like that. And sometimes, there isn’t that much you can do about it. But it’s seldom necessary to spend YOUR ENTIRE DAY sat in front of a computer. And it’s really dumb when you think that this is one of the reasons why you got out of the full-time game in the first place.

But I totally get why it happens. I was raised Catholic and I’m a freelancer – guilt’s my middle name. I’m often fretting if I’m doing enough work, which can make peaceful downtime elusive. The only solution is enforced breaks. That means lunch away from the computer, going for a walk at least once a day, exercising a few times a week, taking complete days off (with phone un-tethered from your person) and setting personal goals. I would go quietly round the bend if I didn’t play musical instruments and take part in concerts/gigs every so often. And accept invitations that get you out of the house – I know this makes me sound like an infirm granny, but there you go.

Error 5: “OMG! This is going so well!”

Freelancing is a cruel mistress. Just when you think you’ve got enough work to keep you in craft ale for months and you can finally sit back and enjoy that Netflix boxset without recrimination or anxiety, BOOM. The work starts drying up, your clients start deserting and you’re thinking “what the hell happened?”

There is no room for complacency when you’re self-employed. Relying on one or two clients is suicidal when you think about all the things that could go wrong. They could pay late, sack you, go bust, get caught up in a sexual harassment scandal…who knows. For instance, as a journalist, I am semi-reliant on having good relationships with certain editors. You click with some, you don’t with others. It happens. But imagine when the editor who faithfully listens to your ideas and gives you work moves into another job (as they wantonly do!)…you might be glad that you fostered other contacts or even other freelance routes.

It seldom helps to pigeon-hole yourself as That Guy/Gal who does That Thing anyway. You’re probably more versatile than you think, and you won’t know what career potential you have until you say yes to new opps. Keep different irons in the fire.

Error 6: You take yourself too seriously

Chances are that whatever you’re doing, it isn’t UN peacekeeping, keeping people alive or going on an Armageddon-style mission to blast asteroids away from earth. Your job or business should definitely have some tangible use to others, and hopefully do some real good, but when you start believing the world revolves around you (as will happen from time to time), you need to get some perspective. After all, there’s only one individual who thinks that they’re the most important person on earth with any real, scary justification – Donald Trump.

And on that cheery note…happy freelancing!


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