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How to ensure 2019 is your best freelancing year yet

By November 28, 2018 June 29th, 2019 8 Comments

We are only five weeks away from the new year. I’m not really one for new year’s resolutions, but I do love to reflect and take stock on where things are at and think about what the next stage of my freelance writing business might look like. With December and January looming, it’s important to carve out some time to think about your approach for 2019. Here are 4 ways to help make 2019 your best year yet.

How to ensure 2019 is your best freelance writing year yet

When I first started freelancing it was a hobby.

It was a “I can’t believe people are going to pay me to write articles!” kind of hobby and in the early days I never thought that I would ever say I was a full time freelance writer and not a social worker.

I think some of my early success in freelancing was due to the fact that I didn’t have a plan – I was just pitching ideas that resonated with me, hoping that editors would commission me, but not really expecting anything in return.

So, I want to preface this post by saying that I don’t think you always need to have a strategy and goals, especially when you are starting out.

But, that said, if you do want to ramp up your business in 2019, hit new targets or even change direction, then now is the time to start.

Once you’ve made the decision to be a freelance writer (in whatever capacity) I can’t tell you the importance of spending some time working towards making your goals happen.

Otherwise the time passes and you’re not making strategic decisions about how your business can support you to live the life you want.

In December 2017, I gave you some ideas for how to have a great start to 2018.

This post builds on that one, with four strategies that you can implement to ensure that your start to 2019 is as fruitful as it can be.

1. Set clear expectations about your availability and workload for January

There’s a pervasive idea in the freelancing world that work drops off in January.

So much of this received wisdom says that you might as well go on holiday because the publishing world is pretty much dead at the start of the year and many corporate clients won’t be in the office.

I’ve found the opposite is true.

The last couple of years I have worked in January (starting from around the 7th January so I still get a decent break) and I have to say that by and large, most of my editors and clients have also been working.

Yes, some stop commissioning as early as November and others don’t start commissioning until the end of January, but last year I picked up lots of work simply by letting editors and clients know that I was around and available.

Of course, I’m not advocating that you work in January if you really need and want a break, but if you have the capacity and the ability to knuckle down to work while everyone else is on holidays, then call it early.

And by that I mean don’t just make the decision to work in January, but make sure you let your editors and clients know that you will be working.

The editors and clients I did this with were grateful that I had let them know and were also happy to outsource some of the work they thought they would have to do before the Christmas and New Year break.

And likewise, if you’re not planning on working, send them a courtesy email to let them know when you’re back on deck.

2. Focus on one thing that you want to change

Freelancing can be overwhelming.

Each day there is lots to do (pitching, writing, invoicing, following up, admin – the list goes on) and it can be tricky to even put your head up to see what direction you’re going.

My advice?

Pick one thing that you can do in December that will set you up for success in the new year.

Maybe you want to start writing for more corporate clients in 2019.

Ask yourself: What can I do in December that will help make that happen?

You might make a list of companies you want to send letters of introduction (LOIs) out to and research the best person to contact. But you don’t actually have to send them – yet.

You might reach out to clients you’ve previously written for but lost touch with and let them know you’ve got capacity to take on work in the new year.

You could increase the number of meaningful connections you have on LinkedIn in the area you are focusing on.

Or maybe you want to break into writing for a specific publication.

You might follow the editor on Instagram or Twitter and start to comment on their threads (building familiarity and a genuine relationship with them).

You might read through back issues of the publication and thoroughly analyse it.

You might workshop pitches with a friend or a writing coach .

Whatever you do. Choose one thing. Just one thing.’

Do that thing.

And then do the next thing.

I’ve found that having a limited and specific focus is really helpful in getting things done.

Break your big goal into tiny, manageable chunks and if you do one small thing each day towards your goal pretty soon you’ll reach it.

3. Check your mindset

Lots of writers I know and work with are wonderful, wonderful writers. They’ve got the craft down pat. But confidence? Not so much. Self-belief? Nope. Solid work habits? Sometimes.

I think it’s really worth spending time thinking about your stumbling blocks.


Fear of failure?

Low confidence?

Not knowing where to begin?

Scared of success?

All of the above? (I know that I’ve experienced every one of those)

As freelancers, we have to be the creative, the CEO, the PR, the visionary, the secretary, the executive assistant and the accountant.

It’s okay, in fact, it’s totally normal to have worries about being and doing all that.

You don’t have to change who you are or how you work. But you do need to recognise if any habits or traits are getting in the way of your success (however you define success).

Notice them. And wonder about them.

Procrastinating getting started on a piece of work? Ask yourself what’s behind your reluctance to get started.

I am a terrible procrastinator, and for me, lots of my procrastination comes down to not wanting to experience the discomfort of working on an article that is hard to write, doing writing that’s less than thrilling or interviewing someone who intimidates me.

These days I acknowledge that I don’t want to do the thing (whatever it is) and say to myself, “I’m going to do this for 20 minutes, and then I can stop.”

I’ve found that to be really helpful.

Has it cured my procrastinating tendencies? No.

But I know that’s how I roll. That by noticing and inwardly remarking on how I’m feeling about a certain task almost relieves the feeling. Almost.

So if you’re feeling scared to pitch an editor? Go gently and be curious about the root of that fear.

We all have inner voices that speak to us, encourage and discourage us, but I really think it’s about recognising and becoming mindful of what they are telling us.

And like any good writers, we need to fact check what those voices are saying.

4. Know that things don’t always go to plan

You can have goals and a business plan, but the uncomfortable truth is that so much is out of our control.

I do a business plan at the start of every year and check in every three months or so, but I still recognise that things don’t always go to plan.

The trick is striking the delicate balance between having aspirations, persistence and strategies to meet achieve our goals, but also being flexible enough to pivot when things aren’t working.

It’s not always clear when you need to stop and change tack, but if you know that this freelancing journey isn’t always going to be smooth and seamless (in fact, it rarely is), that in itself can be a great comfort.

I know this isn’t a quick and easy list of tick box things you can do to get your 2019 off to a roaring start (apart, perhaps, from the first one), but I think the last three points are part of the deeper work of being a freelance writer.

It’s not an easy road, but it’s an incredibly rewarding one. Especially if you lay down strong foundations to start with.

Are you thinking about 2019? What are some of the things you want to achieve?


  • Ricardo says:

    Hi Lindy ,

    As usual, really, helpful and inspirational. I totally related with you on "starting as a kind of hobby ", since I’m working ─as a writer as well─ for a corporation. So let’s say for me now is more a Plan B, a way to be involve in different projects and prepare the ground for my next life step.

    So my goals for 2019 are to keep enjoying this, reach new travel publications and learn as much as possible of this amazing job.

    Greetings from Cape Town!

    Ricardo from Textonality

    • Lindy Alexander says:

      Hi Ricardo,
      Thanks so much for your comment and kind words. Sounds like you’ve got a clear vision for what you want for next year – keep us posted!

  • Lisa Smyth says:

    This has prompted me to write a goals list – thank you! I am currently drowning in work – not a bad problem to have, but also not entirely healthy with lack of sleep and not having time for friends and family. I’ve said yes to everything. Now, I need to figure out what exactly I want 2019 to look like so I have a life outside work.

    • Lindy Alexander says:

      Oh Lisa, the end of year deluge can be brutal! Once things start to ease off, make sure you schedule in some time to rest up a bit and then take yourself out for a lovely lunch to do your goals list – you deserve it!

  • Leah McLennan says:

    I love this post, I haven’t figured out yet how I should try to mould 2019. But I will! What I do know if that since I’ve hired a desk at a co-working space and got out of the house away from the mess I have tripled my productivity. I’m so surprised at this. So one of my plans for 2019 is to stick with the office. But there aren’t any yummy cookies in our office!

    Greetings from Broome!


    • Lindy Alexander says:

      Thanks Leah 🙂 Love that you’ve been able to ramp up your productivity by moving into a co-working space. I’m much more productive at mine too. You may need to be the chief cookie maker?!

  • JoAnna says:

    This is an excellent article, Lindy! As a freelance medical writer, I was determined not be in a work slump in January. I reached out to potential clients in November; as it turns out, they were in need of exactly what I was pitching and look forward to working with me in the new year!

    Your advice in this article really hits the nail on the head. It’s definitely a keeper! 🙂

    I will share this article with my other freelance colleagues.

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There’s never been a better time to be a freelancer. But how do you make the leap from writing as a hobby to full time freelancing? The Freelancer’s Year has all the tips and tricks you need to be a successful freelance writer.