9 Things I’ve Learnt From 4 Years Of Working As A Freelance Writer

No, that's not my desk...

Earlier I was sat thinking of how my three-year work anniversary is coming up – three years of working for myself, that is. I quickly realised, however, that I was wrong in my calculations; it hasn’t been three years since I bid the corporate world goodbye and started working as a freelance journalist and copywriter – it’s been four. Four whole years! For two of those years, I was based in Dubai and for the remainder, I’ve been on the road. It’s flown by so quickly that apparently I blinked and missed a whole year.

It’s been quite the experience.

People are full of praise for the ‘bravery’ of going it alone, and in many respects, they’re right – you do need to have a good amount of fearlessness to say goodbye to a regular paycheque and the other benefits of working for a company, and go solo. So long certainty. So long health insurance. So long paid holidays.

But hello, freedom.

While there certainly are many negatives to this choice of path, there are also many positives. I wouldn’t recommend this to everyone, though, and I am constantly reassessing whether it’s the right choice for me. At this moment in time, I’m really happy and that’s what matters.

Over the last four years, I’ve changed a lot professionally and I still feel I have an infinite amount of things to learn about freelancing and entrepreneurship. However, saying that, I do feel that I’ve grasped the basics of what works for me and what doesn’t. Here are some of the lessons I’ve learnt to date about working as a freelance writer (although I’m a writer, I’m sure most of these apply to all freelance careers):

If you don’t think of career progression you will stagnate and get bored

Most freelancers whom I know aren’t too sure what to do with their new found freedom at some point or another. All of a sudden you realise that you’re responsible for EVERYTHING – from finding new business, to ensuring you get paid, to setting goals in order to further your career and prevent stagnation. And the latter is certainly one element I’ve struggled a little bit with, especially over the last few years as the novelty of working solo started to wear off and I found myself thinking “what next?”

In the absence of regular feedback from a manager, it can be all too easy to stagnate. After all, in a company, career progression can be pretty straightforward – you go from one role to a higher role, and with that comes an increase in pay and benefits, as well as the psychological boost of getting a promotion.

Freelancers don’t have that. We’re responsible for our own growth, which can seem a bit overwhelming at times.

It’s something I definitely didn’t really think about too much back when I wrote this post on how to make it as a freelance writer. I was fine with it for the first year or so, but following that I started to feel pretty miserable. At the time, I couldn’t quite pinpoint why I was feeling down about work, but I realised that I missed having some form of feedback from someone higher up than me – someone with more experience.

I work with some lovely editors, and a lot of them, more often than not, will tell me I’ve done a great job. But that’s it; you don’t get any feedback on what you can do even better next time, what your strong points and weaknesses are; the kind of feedback you only get from working closely with someone on a daily basis. I also started to feel bored because I wasn’t being challenged enough – I got to the point where I could do what I do in my sleep.

So this year, I decided to make career development a priority, and made a list of goals that will help me to grow, from growing this blog into something bigger, to pitching to international magazines for work. This means that away from the work I’ve already been doing, I’m adding new projects and prospects, and (hopefully!) growing in the process.

Steps to take:

  • Stop thinking of yourself as a ‘freelancer’ and start thinking like an entrepreneur. What is your saleable skill and how can you make the best use of it? Can you hone in on a specific aspect of your experience and ‘sell’ it? For example, I noticed one writer started also utilising her skills as a graphic designer and launched a side business creating front-page newspaper spreads that people buy as wedding gifts.
  • What do you need to do in order to grow this year? Take a course? Approach your business from a different angle? Pitch for new business in a market that you haven’t tried before? Make a list of things that take you out of your comfort zone and will give you a good sense of achievement, and make them part of your goals.

You should always, always, always have an emergency fund

Money can be an issue when you work for yourself.

Maybe you’re lucky and you’ve found clients who pay on time, but, unfortunately, more often than not getting paid is an issue for freelancers. There are ways to make it less stressful – for example, you can charge a certain amount of money upfront. But where freelance journalism is concerned, you’re at the mercy of your publisher. Until that article gets published, you’re not getting paid.

Then there are the times when work dries up for a while (yes, it happens even to ‘veterans’ like me), the times when a magazine folds and your article goes unpublished, the times when some unexpected bill falls at your feet with a thud.

In short, I’m not sure how I would have made this work had I not had a chunk of savings in the bank. As much as you plan, sometimes you will fall shorter than you expected, and it’s nice to have a security net to fall on when those days arrive. I think I’ve saved myself a lot of stress by having some money saved.

Steps to take: 

  • If you’ve yet to quit your job to go freelance, make sure you save a good amount of money to keep you going during lean times. I’d recommend at least six months worth of whatever salary you’re currently earning.
  • Charge your clients a 50 per cent deposit when possible.
  • During ‘good’ months, it’s easy to get carried away with your spending, but I’d recommend you put some of it away for a rainy day.
  • Try to find clients whom you can do regular work for on a retainer – this will ensure that you have at least one steady amount of money coming in on a monthly basis.

Multiple income streams are the way to go

This is something that I’m only just realising and I wish I had worked on it previously. I think in the past I was a lot more tolerant of ‘lean’ months. I was just starting out, after all, and I was thankful for the fact I was able to make it work. When I had the odd month or two when work was low, it didn’t bother me too much.

Now, however, I really don’t enjoy it.

I’m at a point in my career where I don’t want ‘quiet’ months, and while I know this is part and parcel of working for yourself, I also know that there’s more that I can do in order to avoid these lulls. This is why one of the goals I’ve set myself for 2016 is to set up multiple streams of income, which means diversifying away from only making money from freelance writing.

I know monetising a blog isn’t easy, but one of the things I’m working on is building the traffic here to a level where I can make at least a bit of money back from it, whether that’s through eBook sales or affiliate links. I’m also working on finding more clients to whom I can offer my writing services through monthly retainers.

Another idea I have is to do a yoga teacher’s training course so that I have another string to add to my bow. My ex suggested to me on many occasions that I should do the course as he knew how much I love yoga and thought that teaching it would perfectly complement the isolating aspect of being a writer. And he was right – it would be a great thing to do as well as writing, however, I’m still not 100 per cent sure and I won’t do it until I know it’s definitely the right thing for me (and my prospective students!).

Steps to take: 

  • Think of what other skills you have in addition to your main freelance gig. Is there anything you can develop further through a course and then do as a side job?
  • If you’ve been running a blog for a while, think of whether you can monetise it. There’s a wealth of information on the internet on how you can do this while staying true to the ethos of your blog.

The key to productivity is a to-do list with set timings

I’ve struggled with productivity over the years. Left to my own devices, I’m the type of person who will have a big burst of energy for a few days, which is then followed by a couple of days of apathy. And while being a freelancer allows you the freedom to work like this, I’ve realised that it doesn’t serve me well and that I’d rather be working on my goals consistently on a daily basis rather than on a random whim.

My main ‘flaw’ when it comes to this is procrastination. I know a lot of writers suffer from it, but I decided this year that I no longer wanted it to rule my life, and so far so good. I’ve found one technique works in particular; I now have a set daily routine that consists of yoga and meditation, followed by an hour of reading emails, managing my social media accounts and setting goals. While I’ve always worked with to-do lists, I now go a step further and list out exactly what I’m going to do and the time I intend to do it by. So the list looks like this:

Screen Shot 2016-02-11 at 17.57.08I’ve read endless articles on productivity and how to stop yourself from procrastinating, and this technique is the one that works the best for me. I tend to do the big things that I’m avoiding first, as not only does that mean I get them out of the way with at the beginning of the day, but it also means I have the fun stuff to look forward to later on.

This also makes me accountable for my own time. Having a to-do list without timings was only half of the battle; yes it helped me to stay organised, but I wasted a lot of time ‘wondering’ what I should do next, and flitting in between the various tasks (note: research has shown that multitasking is disastrous for productivity, so it’s best to avoid that, too).

Now, however, I decide from the beginning of the day what I want to do when, and I feel a great sense of accomplishment every time I cross something off the list. It also means that I complete everything on the to-do list and don’t carry things forward to the next day, which is something I used to do a lot.

Steps to take: 

  • Find what works best for you and your personal goals, and experiment with various techniques before settling on what suits you. For example, are you a morning person? Or could you benefit from doing other things in the morning and working throughout the afternoon and into the early evening?
  • Read articles on websites such as Entrepreneur to get advice on how to stay productive.
  • Know when to admit that an old schedule/way of working isn’t serving you anymore – sure, it may have worked for you at one point, but if your gut instinct is telling you that you can do better, then you probably can.

freelance writing advice

SelfControl is the best app ever invented

I love and hate social media in equal measure; I love that it enables me to stay in touch with my friends and family, that I can use it to source great news stories, and that I can also share my own blog content with the world through it. However, it’s a big time waste. All it takes is to open the Facebook tab under the guise of “I’ll just quickly check my newsfeed” and before you know it, it’s two hours later and you’ve read ten articles on Donald Trump’s hairpiece and gone through four of your friends’ photo albums.

Social media updates come in 24/7, which means you can literally spend entire days on it. Yes, it is also greatly useful, but if you’re not careful you can end up wasting valuable work time.

Enter SelfControl. This application enables you to block websites for a set period of time. During that time, even if you uninstall the app, you’ll still not be able to access the sites on your ‘black list.’

Best application ever!

I’ve become good at policing my own social media usage of late, but I think that’s in part due to the fact I’ve been working with SelfControl for so long that I have seen the benefits of uninterrupted work time firsthand. But whenever I feel I’m lacking ‘self-control’ or I have a big deadline looming, I set the app and get on with it.

Steps to take: 

  • SelfControl is only currently available for Mac users. Windows users can try StayFocusd instead, which does something similar and is available as a Chrome extension.

It’s a lonely profession

During my first years of freelancing, I struggled with loneliness a lot. As someone who’s always enjoyed my own company, I didn’t think that it would be an issue. I quickly realised that you take the interactions you have with colleagues on a daily basis for granted – yes, you’re not sat having deep and meaningful conversations with people at work, but there’s something comforting about the little office banter you have throughout the day.

I discovered that I was actually a lot more social than I thought I was.

The problem was, during those first months, I didn’t realise I was lonely. I felt a sense of emptiness, yes, but I couldn’t quite pinpoint what was causing it. I figured it out, though, and now that I’m aware of it, I know how to try and combat it.

Depending on where you are in the world, and what your situation is, you can do different things. If you’re settled in one place permanently or for a longer stretch of time, you can find fellow freelancers to work with, even if it’s just for a few hours a week. You can all arrange to meet at someone’s place or in a co-working place; in Ubud, ‘digital nomads’ make use of Hubud, for example.

Co-working spaces are popping up everywhere around the world, so even if you don’t have anyone to go with, you can still head to one of these places, make use of the facilities and enjoy having people around you. This can similarly be achieved by breaking up the day and going to coffee shops to work instead of staying isolated in your room/home.

Steps to take: 

  • How social are you? Some people can cope with being alone for longer than others, so it’s important to maintain levels of social interaction that will keep you happy as an individual.
  • If you’re new to a place, a great way to meet people is through the website Meetup. On there you’ll find groups on anything from ‘Singles in Town’ to ‘Expats in XYZ place’ and ‘Photography Walks’ that schedule meetups through the site. It’s a great way of meeting like-minded people and staving off isolation.

Your friends and family are a gold mine of contacts and advice

I’ll make a confession: in some respects, I’m not a very good businesswoman. What I mean is that, until recently, I HATED asking people for things like contacts, or doing any form of networking. And yes, while I did manage to get work without having to do these things, I realised that I’m actually not doing myself any favours by not approaching people whom I know for help or advice.

When I think of how many people have approached me for help over the years, I realise that we all do it. And I’d like to think I always try and assist in whatever way that I can, whether that’s by giving advice to someone who’s emailed me to ask for tips on how to get started as a writer, or forwarding a contact to a friend that I know can help them with something they’re struggling with.

So I asked myself “Do I think less of people for asking me for help?” And the answer was: not in the slightest – so why do I have this fear of reaching out for help?

Since then, if I need something, I’ll ask – whether it’s for the name of someone who may be able to help with an article, or whether I touch base with a friend who I know works for a big company that may need some copywriting done. And sure enough, I have got a lot of work by doing this.

So, in short, don’t be afraid to ask people whom you know for help/advice/contacts/all of the above!

99% of the times it’s not glamorous

Instagram has a lot to answer for if you ask me. I used to look at the photos of people who work remotely and think: now THAT’S living the dream. Sure, it all looks so pretty: your shiny new MacBook parked next to your latte/fresh coconut/cocktail on a coffee shop table/bar top in Thailand. “Look at me, I’m living the life! No more office blues!”

Bullshit.

Don’t get me wrong, I’m guilty of the aforementioned, and let me tell you now – yes, I do work from coffee shops and bars, and yes, I do have a mid-afternoon mojito if I feel like having one, but if you want to make money and stay afloat, this profession is hard.

Yes, I don’t have to get up at a set time if I don’t want to, and yes, I can take the afternoon off to get drunk during Happy Hour. But this happens once in a blue moon; as often, let’s say, as you getting the afternoon off work because the company’s Internet is down.

I love the freedom that freelancing and location independent work gives me, but I think it’s important to remind people that it’s not all sunsets and sangria. Most of the people whom I know who work like I do work damn hard, and 99 per cent of the work isn’t even remotely glamorous. It’s hard, it’s uncertain, and it’s not for everyone.

So before you quit your 9 – 5 thinking this is the easy option, take a good hard look at whether this is for you – yes, it has its many benefits, but it also comes with its pitfalls like with anything else in life. Let’s stop glamorising it, please.

Reassessing your goals and needs on a regular basis is imperative

When I quit my job to travel and work on the road back in 2012 I wasn’t sure how long I’d last. I had an “I’ll try it and see what happens” kind of attitude. I told myself that if it didn’t work out the way I had hoped, or if I finished travelling and realised I wasn’t making enough money to enjoy a comfortable life, I’d get a job again.

Four years later and I’m still going strong.

However, that’s not to say that I’m done with office life for good. Sure, it would take an incredibly interesting job to lure me away from my freedom, but would I do it if the right opportunity came up? You bet I would. Just like you shouldn’t get comfortable in a job, you also shouldn’t get comfortable in your freelancing career.

For example, if you feel you’re stagnating and you’re not sure what next step to take, an office job could be exactly what you need to acquire new skills. Likewise, if you’re sinking and you can’t earn enough money, admitting this to yourself and doing the ‘stable thing’ is better than living in denial and waiting until things get really bad.

I do consider all of this on a regular basis. For now, I’m happy with the way it’s all going and I’m very much experimenting with various things this year, but that’s not to say that if I reassess in a year’s time and realise that getting a job is better for me that I wouldn’t do it. I also regularly scan the job market to see what kind of positions are available, because you never know when your dream job may pop up somewhere.

I guess my point is, I wouldn’t consider it a ‘defeat’ if I decided it was best for me to get a job this time next year. I will continue to do what’s best for me, my health and my career.

Steps to take: 

  • Regularly take a step back and reassess your situation – is your career still making you happy? Are you earning enough to fund the lifestyle you want to have? Are you comfortable or merely getting by – and, if it’s the latter, is it having a detrimental effect on your health and wellbeing? Office blues isn’t the only thing that can make you depressed – I’d hazard a guess and say worrying about money/work 24/7 has a similar effect.

Further Reading

The Freelancer Life – Is It All Worth It? from Travels of Adam – This is a good read for those wishing to understand more about the ‘other’ side to freelancing – the less glamorous/more realistic one.

The Freelancer Life – Is It All Worth It?

How I Make A Living As A Digital Nomad from Free Candie – Rather than show you how to make a living on the road, Candice, who’s one of my favourite bloggers, takes a look at how she does it. I always enjoy reading posts like this in order to see how others make it work.

How I make a living as a digital nomad

How The Hell Do I Afford To Travel? from Mostly Amélie – I like this post, as it gives you an idea of the various ways people make money while on the road – there’s no ‘one way’ to do things, and more often than not, the people who I know who work remotely come up with their own, ingenious ways of making money as they go along.

HOW THE HELL DO I AFFORD TO TRAVEL?


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What have you learnt during the time that you’ve worked for yourself?


  • Thank you for writing this post, seriously! I’m debating wether or not I’m ready to hit the road of full-time freelancing or if I need to get myself a normal job… Still not sure about which is the answer, but this gave me a lots to think about! 🙂

    • Andrea

      I’m so glad you found it useful. Feel free to get in touch if you have any questions – always happy to help. It’s not the easiest of routes to take, but I cannot deny that I’ve had a lot of fun along the way 🙂

  • I really need to start using SelfControl I think!

    • Andrea

      It reaaaaally helps me!

  • Triona McBride

    SelfControl is a great tip, thanks for that. Having freelanced for 2 1/2 years and then returned to a job in Dubai for 6 month and now returning to freelancing again, I completely empathise with all of this. Money can be a struggle (mostly because I went crazy when I had two retainers and then they ended around the same time, through no fault of mine!) and that was why I took a full time position again. It was difficult to adjust, having had my own freedom and flexibility for so long but in actual fact it helped me realign with my goals and focus on what I wanted to do next.
    Great article and I wish you the very best, I’ve always enjoyed reading your articles.

    • Andrea

      It’s always difficult when you lose a client; I remember a major client of mine downsized back in 2013 and it had a massive effect on my business. I was writing so much for them that I didn’t really think to look for any other work, which I quickly learnt was a mistake. But you live and you learn.

      I definitely think it’s important to always reassess where you’re at with it all – I too would take on a full-time position if for whatever reason I wasn’t able to make this work anymore, and I’m sure many freelancers before us have done the same.

      Thanks for the lovely feedback and I’m glad that this was helpful for you 🙂

  • That’s a great point about career progression and professional development! It’s so easy to forget all those other things you do in the workplace beyond just your work. Thank you!

    • Andrea

      Thank you so much – I’m glad you found it helpful. And yeah, it took me a while to figure out that I needed to continue to find new ways to challenge myself, but I got there in the end!

  • This is such a great post Andrea! I feel like I really need to take some steps into getting income now that I’ve been on the road for almost 2 years and going off of mostly savings. Unfortunately, I’m one of those people who have no business sense at all and hate networking and asking people for help. And I am a really bad procrastinator too! Ugh… so many bad habits! I’m really impressed with how many tasks you’re cramming into a day. But yeah, your post is giving me a lot to think about!

    • Andrea

      I hoped it helped a little? Let me know if you ever need some advice – more than happy to help in any way that I can. I’d suggest starting to do little things and building it up, rather than leaving it until the last minute and panicking once you’ve run out of money. And yeah, I really know it’s easier said than done – I am the QUEEN of procrastination, so this doesn’t come easy to me at all! But I’ve learnt that doing a little each and every day is better than leaving things or avoiding work all together.

  • Andrea, thank you for this insightful post! I can see you put a lot of effort into it.
    I used to think that freelance job’s rainbows and smiles but now I know it’s hard work often exceeding “normal” 9 – 5 schedule.

    • Andrea

      You’re welcome, Joanna 🙂 Yeah, I think it almost reached 4,000 words, haha. And yeah, I know that there are some people who have managed to set up passive streams of income and probably only work a few hours a day, but I’m pretty sure they’re the exception. If I knew their secret, trust me, I’d be doing it, too. Who wouldn’t want to work less and yet still earn well? 🙂

  • Hi Andrea, Thanks for the shout-out and for the insightful piece. Your comments about loneliness ring so true for me and it’s something I struggle with a lot. Really appreciate it <3

    • Andrea

      You’re very welcome, Adam. Your post really resonated with me. The loneliness part sucks – I hope you’re finding it more manageable as you go along?

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