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The 6 inevitable truths about being a freelance writer

By February 17, 2021 14 Comments

There are certain realities you need to prepare yourself for if you’re a freelance writer, or want to be one. This is not about working from home and finding yourself in your pyjamas at 3pm (although trust me, that may well happen). And it’s not about friends who think you are permanently available for coffee because you are freelancing. No, this post is about my inevitable truths of being a freelance writer.

The 6 inevitable truths about being a freelance writer

1. You’ll get knocked down, but you’ll get up again

(With apologies to those people who now have this song stuck in their head).

It is a truth universally acknowledged that freelance writing involves a lot of rejection.

Rejection comes in lots of forms – an editor saying no to a pitch, an editor not responding to a pitch, a client asking for a endless rewrites and so on.

A few years ago I interviewed the wonderful poet David Whyte for DumboFeather magazine.

He spoke to me about how traditional craftspeople work – they spend a third of their time preparing, a third of their time working and a third of their time cleaning up.

The actual doing part (the harvest) is just one portion of our freelance lives. 

But it takes a lot to lay the groundwork properly and do good work.

David spoke about the importance of humiliation – that we can’t avoid humiliation or being rejected.

“Humiliation has that beautiful root of humilis, meaning ground or soil,” he told me.

“So both the ground that you come to and the soil from which the new harvest is grown. Every path you try to take in life, whether it’s the path of relationship; intimate relationship or the relationship of a mother or father to a child, or in marriage, or the relationship to your work and vocation, or the relationship to yourself, you will have your heart broken on each of those paths.

There’s no path that any human being can take without having their heart broken.

“We spend enormous amounts of willpower trying to find a contour to follow where we won’t have that imaginative organ broken apart.

So the only question seems to be, will you have your heart broken with something you care about?”

When he said this to me, I felt like the world stopped.

I think sometimes it’s tempting to try and avoid rejection and failure, but they are both an inevitable truth and part of being a freelance writer.

You don’t have to love rejection (or the fear of it), but are you going to let it stop you?

2. Other freelance writers are the best

Ever since I started freelancing, I’ve been part of a lots of writers’ groups.

Most of these groups are online and are fantastic communities.

Having a space where you can ask questions, vent and celebrate is important when so many of us are scattered across different countries, sitting at our kitchen tables, co-working spaces or cafes.

And when I first started freelancing, I made a concerted effort to reach out to freelancers I admired like Libby Hakim, Megan Blandford and Lani Goonesena who, like me, had come from non-journalistic backgrounds, were parenting young kids and writing full time.

I was interested in the stories they were writing, the balance of content/copy/feature writing they were doing, and just generally how they were finding freelance life.

Fellow freelancers also make the best colleagues – often they are happy to proofread pitches or articles and offer advice about places to pitch (or avoid).

Some of my closest friends are now freelance writers who understand instantly about the challenges, pressures and joys of this work.

As I start to put more energy into running online courses for freelance writers, I also regularly pass work onto other freelance writers.

Freelancers I know have done this for me in the past.

They’ve introduced me to editors, passed on work when they were too busy and suggested me when clients were looking for a writer.

I really believe that collaborating makes us stronger.

This is what we would naturally be doing in a regular office environment (and yes, out in the wild).

I know in some freelancing circles there is a reluctance to be generous with ideas, advice or support because there is a sense that all we are all in competition.

But I don’t buy that.

Our ideas may be competing, but I’m not.

I don’t have a problem passing on information about a particular publication I write for if someone is genuinely at a loss with where to find contact details or the like.

If someone is pitching the same editor as me and they have the stellar idea and I don’t, then honestly, I’m happy for them.

Because I’ve found that most freelance writers are generous and supportive and if you give freely, that comes back to you ten-fold.

3. You need to invest in yourself

Whether you go to conferences, do a course, meet up with more experienced freelancers, listen to podcasts or read books about writing, it’s vital to develop and hone your skills.

In order to grow your business (even if you’re a micro-business of one), you need to invest in yourself.

There are so many opportunities out there that it can be overwhelming to know what to choose.

Ultimately you need to make decisions that will (eventually) get you where you want to go.

Sounds so simple, eh?

In the past I’ve bought courses, tickets to online conferences and watched webinars without asking myself how it’s going to help me reach my goals.

I used to pitch publications in a scattergun way, without considering if writing for a particular publication would meet my goals.

Those goals might have been anything from learning more about a particular subject, meeting my income target for that month, or getting a commission in a specific publication.

It can be scary to put time or money into something, especially if you’re not sure it’s going to ‘work’.

But there are no guarantees.

In 2020, I invested $15K+ in a year-long intensive program and I felt absolutely sick handing over that kind of money.

But when I did, I knew I had to make my commitment worthwhile.

So I went all in.

And I’m so glad I invested in myself and my business.

That’s where the growth happens.

4. Case studies and experts won’t get back to you until right on your deadline

If you don’t take anything else away from this post, do this one thing:

Tell case studies and experts that your deadline is earlier than it is.

There are two kinds of deadlines in freelancing: 1) when you need to file to the editor and 2) the deadline you need to hear back from case studies and experts.

If your article is due on Friday, don’t tell your case studies that.

Instead, tell them the latest date you can to speak to them (ideally a few days before the actual latest date) or when you need their email responses by.

The most stressed I’ve been is when I’ve told case studies and experts my date for submission, assuming they’ll do the maths and get back to me in time for me to transcribe their article (affiliate link), and include their comments into the piece.

But they don’t.

So now I tell them it’s due a week before.

Even two weeks before it’s due.

Then I tell them when I need their comments by.

I always give them a date – not ‘at your earliest convenience’.

I give them a concrete day and time.

Because there’s nothing more stressful than your article hinging on a case study who hasn’t got back to you in time.

5. You’ll say yes to the wrong things

For a short word, ‘no’ can be awfully hard to say.

At least, it is for me.

In my early years of freelancing, I said yes to a lucrative project that I knew wasn’t a good fit for me.


Because I was flattered the organisation had approached me, because the remuneration was excellent and because I had capacity.

I started the project and resented each time I’d work on it because I didn’t enjoy it. At all.

And honestly, it was beyond my abilities.

I knew as soon as I was approached that this wasn’t a good move.

But I still said yes.

Because I didn’t want to say no.

But that was a huge mistake.

After that experience I’ve learnt to take my time and really evaluate opportunities as they come.

Another inevitable truth of being a freelance writer is that you’ll say yes to the wrong things.

But that’s part of the learning process.

The real mistake is if you keep saying yes to the wrong things.

6. Freelance writing is both tiring and exhilarating

In a regular job you have down times, you have periods where you can ease off a bit and you’ll still get paid.

Freelancing, not so much.

But, you can’t be productive all the time.

I’ve definitely had lots of days where I just can’t motivate myself and end up surfing the web.

Or I puddle about on news sites, pretending that I’m researching story ideas.

On those days, it’s best to shut down the computer and take a total break.

Since I’ve been a full time freelancer, I don’t think I’ve ever worked so hard in my life.

But I look at the articles that have been commissioned and published, the words that I’ve written, the income in my bank and I’m proud.

I have been responsible for every single dollar that I’ve earned and there really is no better feeling.

That’s balanced out by feelings of total exhaustion, though.

There have been weeks where I’ve had nine feature stories due and I’ve felt like I’m drowning in work.

But one of the promises I have made in this freelance life is to do what I say I’m going to do, when I say I’m going to do it.

And there’s nothing better than getting to a Friday evening when all the articles are in and done.

And you get a little breather, just for a couple of days.

Before it starts all over again on Monday.

And that’s yet another truth of being a freelance writer.

Once you’re established, there’s a real sense of momentum and movement.

And I wouldn’t change it for the world.

What are your truths about being a freelance writer? 


  • Jennifer Morton Writer says:

    Hi Lindy – what I want to know is how do you work on and write 9 features in a week? I’m struggling with 4 (3 really because 1 is a travel review) and I’ve had 2 weeks in total.

    • Lindy Alexander says:

      With difficulty, Jennifer! I looked at all my due dates (one on Monday, four on Tuesday, one on Wednesday and three on Friday) and worked out roughly how long each would take to write and organised my time accordingly.
      It’s been pretty stressful!
      I have three more features (all 1200 words +) to go (all due Friday) and I’m nearly done with one, three-quarters of the way through the next and haven’t started the last one, but I have done all the interviews and know the structure.
      I’m not in a hurry to repeat this experience, but it has taught me just how much I can get done when I focus and stop checking email/twitter/facebook every 10 minutes!

  • Michaela Fox says:

    YES! Oh I can relate to all these 7 truths! I especially like what you say about the importance of collaborating and sharing knowledge. And no. 7 is so true – much like parenting!!!

    • Lindy Alexander says:

      I hadn’t thought of that about number seven, but I think you’re right Michaela!

      In terms of collaborating, the more I work as a freelancer the more I think it’s the only way to survive and be successful. After all, all the articles we write are collaborations with case studies, experts etc.

  • Persephone Nicholas says:

    Hi Lindy,
    Great post. You are absolutely right about the importance/value of collaborating and sharing with fellow freelancers. Being a freelance writer can feel like working in a vacuum and having like-minded ‘colleagues’ to bounce ideas around with is invaluable, no matter how long you’ve been doing it.
    Best of luck with the 9 articles : )

    • Lindy Alexander says:

      Thank you Persephone 🙂

      How lucky are we that we are working in a time when you can so easily connect digitally and remotely to other freelancers so that we do feel that we have ‘colleagues’?

      Thanks for your good wishes with my articles – I’m getting there. SLOWLY.

  • Karen Smith says:

    Learning to say no in any form of free lance or consulting job is very important.
    Good to see you mention it. Knowing you are not a good fit for the work or an organization is important.

    And yes. We have a choice about sharing. Good to see you have found those with this attitude.

    • Lindy Alexander says:

      Thanks Karen, I must admit I’m only at the start of my journey of saying no! Finding other freelancers who are open, honest and willing to share their experiences has been wonderful.

  • CJ says:

    You’re right, it’s amazing how much more I can do when there’s a deadline. Suddenly I’m productive! I’ve been more selective about what I do lately. I wrote quite a bit for free to start with, and I don’t do that any more, nor any of the really low paid jobs. Connecting with other freelancers online has been incredibly important to me. I’ve learnt so much and it’s good just to know that other people are doing it successfully. I don’t know many writers in real life, so without the internet I’d feel very alone. Good luck with the nine articles – just think how amazing you’re going to feel when they’re all done!

    • Lindy Alexander says:

      Deadlines are the best (sort of). That’s great that you are starting to move away from free/low paying work, and I think connecting with other freelancers often gives you the confidence to do that. There are so many great opportunities to connect with freelancers online and IRL.
      I have just finished the 9th article. Need to have a break and then come back with fresh eyes before I re-read and then hit send. Whew! What a week.

  • Daniela says:

    This is a fantastic post Lindy. Very helpful to a newbie like me. Cheers! PS Do you have a similar post on the business side of things?

    • Lindy Alexander says:

      Thanks so much Daniela. I don’t have a similar post on the business side of things but what a great idea – I’m scheduling it in! Thanks 🙂

  • Anna Frymire says:

    So grateful and happy I found your site. Thank you for sharing your expertise. Everything you described is what I’ve experienced so far (just on a smaller scale). After seven years in nonprofits and juvenile justice, I left that career. I’m in a fortunate position where I have the money to not make money (for a time) so I took the leap. With that said, I know that I took this leap without planning (which is odd for me because I plan just about everything). I followed my gut. Following my gut was fine at the beginning, but now I need a schedule for my days and a strategy. Thank you for your helpful tips!

    • Lindy Alexander says:

      Hi Anna, thanks so much for your comment. I think it’s wonderful that you’ve followed your intuition, but you’re right, having a plan and strong habits really helps confirm that your gut instinct was right. Keep in touch and let us know how you are going.

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