How to build freelance confidence

by Tom Albrighton 13 March 2014 Freelancing

It’s strange when novice copywriters ask me for advice, as if I had all the answers. On the inside, I still feel like a charlatan, somehow getting away with it despite the constant risk of being ‘found out’.

At the same time, though, something has changed in the nine years I’ve been freelancing. I’ve found some ideas and approaches that have helped me gain confidence – or at least operate better without it. In this post, I’ll try to explain what they are.

Confidence doesn’t come easy for freelancers.

Going freelance isn’t just about switching to a new way of working. It’s about taking on a new way of living, a new way of understanding your life.

As a salaried employee, your work is relatively easy to keep in its box. It’s centred on a particular place – an office, probably – that you go to, work at, and then leave. It’s generally bounded within certain times, outside which you are ‘off duty’. And as long as you meet the demands and expectations placed on you, you’ll be rewarded with predictable, pre-agreed amounts of money and free time.

As a freelance, all that changes. Suddenly, your work, your money, your home life and even your health are constantly in flux, linked together in a poker game where every play matters, everything affects everything else and the stakes could hardly be higher.

freelance factors

If you take that big job, you won’t see your daughter this weekend, but maybe you could take her on holiday. You really need to do some work on the house, but that will mean less productive time at the keyboard. Putting in extra hours will generate some welcome extra cash, but what about that pain in your shoulder?

You face this new reality in a context of endless, turbulent uncertainty. Your timetable, previously so ordered, descends abruptly into chaos. Some jobs are delayed interminably, then cancelled. Small jobs get big, big jobs get small. Jobs you thought could wait are suddenly, unfathomably urgent. In place of a single boss, you have multiple minibosses – and there’s absolutely no law that says their demands can’t be in conflict, or that the tasks they give you have to add up to a neat eight-hour day or five-day week.

Then there’s the money thing. Now, every hour must be counted and costed. Every pound has to be hustled for, negotiated, billed and chased – and nothing will happen unless you make it happen. Your potential income, so stable as a salary-earner, now hangs permanently in the balance, fluctuating wildly on the whim of someone you’ve never met, someone who may be nothing more than an email address to you. Add dependants into the mix and all this takes on an unwelcome extra edge.

If you’re lucky, you’ll get support from friends, family or maybe some sort of professional network. But unless you’re talking to another freelancer, nobody will really understand what it’s like to be out there on your own, putting yourself and your self-worth on the line in a market that can feel indifferent at best, downright hostile at worst. And at the end of the day, it’s your work, your decisions, your money, and no-one else’s. When the chips are down, nobody’s got your back. In this sense, a freelancer is always alone.

And that’s the context in which you have to start building up your confidence.

Confidence affects ability.

It wouldn’t be so bad if confidence (or the lack of it) was just something that lived inside your head, like a catchy song or irritation at Jeremy Clarkson. In fact, it touches every aspect of your freelancing life: how you describe yourself and your work, how you position yourself in the market, which jobs you go for, how you negotiate prices and timescales, how you handle feedback and how you meet challenges like non-payment and losing clients. For freelancers, confidence is destiny.

Adapting Kate’s idea, consider a simple mathematical model where confidence is a moderating factor on ability. So if your confidence is 70%, you can use 70% of your ability. In this world,  someone with far superior skills but puny 60% confidence in them (A on my diagram below) will underperform someone with modest ability and rockin’ 90% confidence (B).  confidence affects ability Obviously, people can’t be reduced to bar charts, but the point stands. You can only use your abilities to the extent that you believe in them. Or, to put it another way, big ability won’t compensate for little confidence. Sad but true.

Confidence is a choice.

The first step to becoming confident is deciding to be confident. I’m not saying that you’ll magically become confident as soon as you make that decision. I’m saying that you won’t start becoming confident until you do. The choice to be confident is necessary, but not sufficient: if you want to climb the top step, you have to climb the bottom ones first.

Perhaps there will be many steps to take before you feel confident. But none of them will happen unless you want them to. You’re not going to ‘just’ become confident, any more than you’re going to ‘just’ learn Chinese. And you’re certainly not going to become confident against your will.

Confidence is a muscle.

If confidence affects ability, it follows that you should actively work on it, not just passively accept your lot. If you care about developing your hands-on skills – writing, design, web development or whatever – you should also develop your confidence in those skills. That’s what makes the difference between a hobby and a viable freelance career.

Building confidence simply means edging outside your comfort zone whenever you get the opportunity to do so. As a freelance, those opportunities will surely come; the most obvious one is being asked to do something you’ve never done before. If conditions are favourable – for example, the request is from a client for whom you’re already the ‘go-to’ supplier – then take the plunge.


Once you’ve put yourself in a few confidence-testing situations, you feel confident about trying a few more. You’re not just building your confidence; you’re also building your ability to develop confidence. In other words, you’re learning how to learn, as well as learning. And before you know it, you turn around to look at the view and realise you’ve actually climbed a pretty big hill.

Confidence is a way of seeing.

Once, when I was feeling fed up with my publishing job, I sullenly told my boss that I was thinking about going freelance. He told me I’d just be ‘scrabbling around for work’. And I didn’t go freelance until many years afterwards.

Logically, I can see that his remark was coloured partly by his own freelancing experiences, partly by a desire to retain the editor he’d just spent two years training up. But it cut deep at the time, and gave me an enduring sense that I wasn’t cut out for freelancing somehow, or that freelancing just wasn’t viable as a lifestyle. And although I’ve obviously moved on from that, I still remember the conversation, nearly 20 years on.

My response to this episode was determined by my explanatory style. This determines whether we internalise the causes of events, or see those causes as outside ourselves. If your personal explanatory style is positive, you tend to blame others for bad events and take credit for good ones, and vice versa if it’s negative. Very negative explanatory styles have been linked with depression.

Of course, there are shades of grey between these extremes, and people’s reactions vary, but the point remains: if the way you respond to events or feedback isn’t helping you, maybe you could change it. Some responses close down your options and rob you of control, while others give you power, perspective and choice.

This table shows a few things you might hear as a freelancer, and how you could interpret them in different ways.

Actual words spoken Less confident interpretation More confident interpretation
‘Go freelance and you’ll struggle for work’ ‘He’s talking about me. I couldn’t be a freelancer’ (internal, pessimistic) ‘He’s talking about himself. My experience will be different’ (external, optimistic)
‘We’re not sure about the direction you’ve taken’ ‘I’m incompetent’ (internal, pessimistic) ‘They didn’t brief me properly’ (external, optimistic)
‘We’d like you to make a few changes’ ‘They don’t like what I’ve done’ (external, pessimstic) ‘I’m nearly there’ (internal, optimistic)
‘We really like your work’ ‘They don’t really know what they’re talking about’ (external, pessimstic) ‘I am talented and professional’ (internal, optimistic)

Similarly, here are some situations you might face, and different ways of viewing them.

Real-world situation or event Less confident interpretation(s) More confident interpretation(s)
Client tries to negotiate a lower price ‘They won’t use me unless I reduce the price’ ‘They want to use me, so I don’t need to reduce the price’
Client moves on or stops using you ‘They hate me’

‘I’m rubbish’

‘I let them down’

‘I can provide more value elsewhere’

‘Their loss’

‘They’ll be back’

Lots of local competition Not enough work to go round There must be lots of work to support all these people
Another freelancer has better clients, website, portfolio etc ‘I’ll never be like that’ ‘They’re further along the road than me. That’s where I’ll be one day’

If you were trying to make purely rational decisions, you’d be concerned that these interpretations, while helpful, might be pushing you into either fundamental attribution error or its converse, actor-observer bias. But in this context, you’re sacrificing objectivity for psychological support. At some points in your freelance career, the ‘problem’ of overconfidence is just what the doctor ordered.

Remember, none of this has anything to do with reality. It doesn’t mean you ignore feedback, run your business recklessly or pretend you never need to improve your skills. Rather, this is an interpretation of reality that you choose to adopt when you need confidence and strength. Whether the beliefs are true or false is irelevant; the point is whether or not they’re useful.

Confidence is something you already have.

If you feel unconfident, it’s easy to think of confidence as something ‘out there’ – a ‘thing’ separate from yourself that you need to acquire somehow.


As I’ve argued, hoping for confidence to ‘just happen’ is like hoping for a rainbow: it’ll arrive eventually, but you could be waiting a long time. This perspective robs you of control and makes you an observer of the events you want to influence. It’s far better to adopt one of the core tenets of NLP: you already have all the resources you need.

In other words, you already have confidence – you just need to nurture and refine it. And even if you don’t, you definitely have the ability to acquire confidence. Everything you need is already close at hand.

Seeing confidence as already part of you is much healthier than seeing it as some alien thing that’s going to come and sit on your shoulders. You’ll never become something you fear or despise.

Confidence is a lie you tell yourself until it comes true.

‘If I felt more confident, I could act more confident!’ That sounds logical and obvious, and it is true, but the causality runs both ways.

The mind and body are co-dependent, like a bicycle and its rider: you move by balancing, but you also balance by moving.

In other words, if you act as though you’re confident, by modelling the movements, body language and speech patterns of confident people you know, you can start to feel the emotions that go with the actions. Stand up straight, square your shoulders and look up to the sky, which is the place to look for a brighter future.

Confidence, like its opposite, lives in the body as much as in the mind, so physical activity can help a lot. When my daughter was a toddler, she went to a scheme called Tumble Tots, where preschoolers learn skills like climbing, balancing and throwing. This massively increased her confidence with all types of challenges, not just physical ones.

Regular readers will know I’m always on about running. That’s because fitness isn’t just about maintaining your body as you might maintain your car. It’s about taking care of the whole system: your mind, your body and your emotions. Confidence has its roots in all three.

Confidence is created twice.

In fact, everything is created twice: once in thought, and then once again in reality. Before you physically write something, or design something, you imagine the finished work. Success depends on how well you can turn your imagination into reality – and the more convincing your mental image, the easier it is to make that happen.

Confidence is exactly the same. Imagining yourself acting confidently is a great way to ‘bootstrap’ yourself into a more confident frame of mind – particularly if you’re about to try something completely new. Picture yourself dealing with the situation in a confident way makes it feel more natural and predictable when the time comes to do it for real. Instead of going out on a limb, you’re just fulfilling your expectations.

Even after almost a decade as a freelance writer, I’m still beset by doubts before I start a job. I won’t understand the topic. I won’t be able to meet the brief. I won’t have any ideas. To combat that, I run over the micro-actions that I know I’ll soon be carrying out – reading through the source material, creating a document, setting up headings. In my mind, this turns the writing process into a known, safe journey that I just have to start and then move through step by step, as opposed to an unpredictable voyage through chaos and uncertainty. Start with the end in mind and you’ll arrive sooner than you think.

Confidence is becoming, not being.

Confidence is important, but so is perspective. It’s easy to look at other people and think they have everything handled – particularly if you’re watching their personal ‘highlights reel’ on social media. Buf if you could look inside their heads, you might see a very different picture.

The very best people are usually insecure and fear being ‘found out’. And I mean the very best people. I once asked David Ogilvy when he finally felt secure about himself and his reputation. ‘About five years ago,’ he replied. He was 85.
Steve Harrison, How to do better creative work, p.27

I think we’d all like to be insecure like David Ogilvy. He knew the value of his work and his ideas, but his attitude was very far from blind, complacent self-assurance. Instead, it was about self-awareness and the desire to keep getting better. For me, this is the best kind of confidence: determined without being heedless, focused without being blinkered, responsive without being weak.

Maybe confidence means always travelling, never arriving; or always becoming rather than being. Maybe you’ll never be truly confident in the sense of telling yourself ‘I am confident’ and believing it. Maybe your confidence will be something that only others can see, like your sex appeal. None of these things mean that your confidence isn’t real, or that it won’t work – just that your ideas about it might need to change.

Confidence is an option.

There are lots of reasons to want confidence. But there are plenty of reasons not to want it too.

In Keith Waterhouse’s novel, Billy Liar talks about ‘wearing [his] sensitivity like armour’. If you’re naturally shy or introverted, you might feel that a lack of confidence is part of your personality; an amulet you don’t want to let go. As I’ve explained, explanatory style has its roots in childhood, so changing it might feel like a betrayal of who you ‘really are’.

You might associate confidence with being brash, overbearing or crass. Or you might also look at stereotypically confident people and feel that you don’t really want to be like them. If you’re a creative, for example, you might not want to be like an agency suit.

Then again, maybe you’re uneasy about all the self-help pop-psych BS I’ve been handing you in this post. Believe me, I understand – while the ideas are useful, there can be an undercurrent of selfishness and vanity to the whole self-help project.

If you feel this way, remember that you don’t have to be all confidence, all the time. If confidence is a choice you make or an act you put on, it follows that you can drop it when it’s no longer useful. Becoming confident needn’t mean becoming a different person. It can be nothing more than having more options in certain situations, or seeing things a certain way when you want to. In fact, if I had to sum up the whole of this post in three words, I’d simply say: you can choose.

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  • bravenewmalden

    I’m going to cut this article out and impale it above my desk, or whoever’s desk I’ll be sitting at next week. It’s totally nailed my particular and seemingly permanent doubts about being a freelance copywriter (or any kind of copywriter), right down to the pain in my shoulder.

  • Thanks for the kind words Kevin. I think my shoulder pain, which is invariably on the right-hand side, is due to excessive mouse use. Maybe if I could just type the text right first time, I wouldn’t have to fiddle with the damn thing so much.

  • bravenewmalden

    There’s still be Scramble, though – that doesn’t help.

    I’m currently undergoing a course of acupuncture to try to alleviate the pain. Not sure if it’s going to work but it’s certainly making my wallet a lot more supple.

  • bravenewmalden

    There’d.

  • Maybe we only have a finite number of words we can use in a lifetime, and there we are splurging them all on Scramble and Words With Friends…

  • Excellent post Tom – and essential reading for anyone considering freelancing.

  • Thanks for the kind words, Huw.

  • This is a really great blog post Tom and that negative self talk exercise is really useful. I must say, going freelance has increased my confidence in my work no end. There’s something in having to juggle all the pressures you mention that really builds your character, I think. Do you think you’re more confident as a result?

  • Jeannie Goodrum

    Excellent! Very encouraging words!

  • Claudia

    Brilliant, brilliant, brilliant and illuminating post! Thank you! You made my day..in these days when I’m thinking of giving up and am actually re-thinking and re-considering everything I’ve done in life 😀 Thank you

  • Ed

    I’m certain that this is one of your best posts yet. In particular, those tables represent very well the typical psychological processes we all go through.

    It reminds me of the 3-tier system of “Comfort zone, Stretch zone, Fear zone”, which I think is in line with what you’ve said here.

    Your comfort-zone may never allow your talents and confidence to grow. Your fear-zone will likely cause you such stress and uncertainty that you’ll find yourself shying away from future opportunities.

    But time spent in the stretch-zone is an ideal balance of building confidence on top of experience: a middle ground between stagnancy and crippling doubt.

  • Siobhan Morton

    Thanks for this! I am on the brink of setting my freelance website live but have been stalling. Why? A lack of confidence of course – but these words have inspired me to get on with it 🙂

  • Nick Hall

    Excellent stuff, we all suffer the demons at some point. I studied a lot of NLP for the sales and copywriting side and found one amazing technique from Paul McKenna. Take the negative voice and you find it always has the same tone. It’s a parent, horrible boss or an overbearing teacher, listen and it’s there. It’s in the same place, too, relative to your eyeline. He said move it, change the voice to something shrill and weak, and it’s power instantly diminishes. It sounded mental, but it worked.

  • Yes, I think the fact that these techniques sound mental does put a lot of people off trying them – as does McKenna’s previous life as a stage hypnotist. But for the price of a paperback and a few minutes doing purely mental exercise, or listening to some audio, it has to be worth a try.

  • Thanks for the kind words Siobhan. I’m glad the post was helpful.

  • Thanks for the kind words Ed. The comfort, stretch, fear model is very much in line with my thinking.

    Last year I had to speak in public at the first PCN Conference, which was a daunting assignment for me. The dread of addressing a large group hung over me for the whole of the summer. When the time came, it was no big deal. So I’d definitely agree that while the net result was positive in terms of developing confidence, the cost in terms of the stress beforehand was pretty high. If I could have chosen, I would have addressed a smaller group first, but I had no choice but to go headlong into the FEAR ZONE…

  • Some great advice Tom. Posts like these reverberate far beyond copy.

    Also, on a similar note to others, I should add that reading your book alongside scattered blog entries has finally given me the confidence to start the freelance journey, so cheers for all the indirect encouragement. Will see you in the howling corridors of Twitter.

  • Thanks for the kind words! Hope the freelancing works out and see you on Twitter…

  • Work YourWords

    Brilliant, thanks for writing this. I got here via your perfect diatribe against networking (I was consumed by networking angst) and now I’m feeling all soothed by your confidence massage. It’s kind of like therapy coming over here 🙂

  • Thanks for the kind words! I’m glad you enjoyed the post.