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What I wish I had known when I was starting out as a freelancer

By January 22, 2020 April 28th, 2021 14 Comments

I’ve been a freelance writer for 10+ years now. It seems such a crazy thing to say, given that in my 20s I couldn’t ever imagine a time when I wouldn’t be a social worker.

I’ve always loved writing.

Ever since I can remember I’ve put words down in order to process my thoughts and express feelings I couldn’t manage to say.

When I lived in Uganda in my mid-20s, people would reply to my emails saying, “You should write a book”.

In my mid-30s when I was doing my PhD my supervisor would always complement my writing style (My research skills? Um …. not so much).

When I started freelancing, I never had a vision to become a full time freelance writer.

I was simply seeing if I could write something that someone wanted to publish.

And slowly, I realised that I wanted to be a freelance writer.

It’s been a lovely, organic journey.

But it does mean there are things I wish I had done differently when I was starting out as a freelancer.

Being a writer is not only about writing

What do you do?

I’m a writer.

Writer. It’s such a simple word.

But actually, what I didn’t realise when I first started freelancing is that hiding behind the word ‘writer’ is a lot of other words.

There’s pitching, prospecting, invoicing, interviewing, following up, transcribing, chasing payment, researching, editing, networking … the list goes on.

As a newbie freelancer, I pitched, got commissioned (if I was lucky), wrote the story and invoiced.

But as my business has grown, I kind of wish I had known that I’m not going to spend most of my days writing.

Rather, the writing bit is only part of what I do.

I’ve had to learn loads of new skills on the job.

And I think I would have preferred if I was a little more prepared.

I probably would have set myself up with a simple, free invoicing software from the beginning (like this one).

I definitely would have kept better records of all my contacts and pitches.

And I would have set up a system for recording receipts and anything that I could claim on tax.

Hindsight is a fine thing, eh?

But having simple, effective systems in place from the get-go means you’re setting yourself up for success.

Setting limits is essential

For years I was so thrilled that editors and clients were going to pay me for my words, that I said yes to every opportunity.

I am, by nature, a person who finds it hard to say no.

But I wish I had known at the beginning that setting limits and strong boundaries is crucial to maintaining your freedom (and sanity) as a freelance writer.

While I really don’t believe that writers need a routine, I do think I would have benefited from setting some limits.

Too often in the early days I was working until 9.30pm.

I worked every weekend, I interviewed experts in my car in my lunch break (while I was still working as a social worker).

Or I took on corporate projects that were beyond my capabilities.

It’s only been in the last few years that I finally cordoned off weekends.

And now 95% of the time Saturdays and Sundays are family time.

And it’s only been recently that I’ve decided I really need to do something about my procrastination.

It was after reading this stunning article about what technology is doing to us that I have committed to pursuing distraction-free work time.

The author of the article above quotes research that found that when people work on computers, their attention breaks every 40 seconds.

Less than 20 years ago it was every three minutes.

I found that such a scary statistic.

I know that I am like a meerkat every time my phone buzzes or I get a notification on my computer.

My concentration is broken and I need to do something about it.

And COVID-19 hasn’t helped either.

But I wish I had set limits earlier.

Because it’s too easy for the flexibility of freelancing to turn into a burden.

One where it’s hard to know where life starts and work ends.

Be patient, grasshopper

I think one of the reasons I love freelancing so much is because of the many spikes of joy you can get like …

Sending off a pitch you’re excited about

Getting your first byline in a publication you love

Writing content that aligns perfectly with your values

Getting a commission

Receiving an email from an editor offering you work

But I’ve found that while my efficiency has meant that I can usually turn out work quickly, I haven’t always taken the time I needed to consider pitches, replies or even where my business is going.

I tend to be quite impatient about what I want to achieve and when I want to achieve it by.

But I wish I had known that freelancing is about playing the long game.

One of my first (big) commissions was with a Sunday paper.

I was absolutely thrilled with the editor commissioned me and even happier when I got glowing feedback from her.

Each week I checked excitedly for my article to appear.

Do you know how long it was between submission and publication?

Nine months.

I had almost given up on ever seeing that piece, despite the same editor commissioning me since I submitted it.

So my advice is this: Be patient, my friends.

Editors take time to reply to pitches.

It takes time to build relationships with clients.

But it’s about the compound effect – where little small steps add up over time to make a big impact on your life.

So yes.

I would tell myself to slow down.

Don’t be in such a rush.

Don’t expect everything to happen immediately.

Because even once you reach your goals, you’re going to want something else.

Something more.

And that takes time. And patience.

Feedback is not criticism

Okay, I should clarify.

Sometimes, feedback from editors and clients is criticism.

I’ve definitely been on the blunt end of some ALL CAPS feedback from an editor that didn’t feel like anything other than condemnation.

But in the beginning, I took feedback and requests for edits from editors and clients as a sign that I had failed to do my job properly.

I didn’t realise that feedback is all part of the process, and in fact, I should have viewed it as a conversation.

A conversation to learn more about my writing and where I could improve.

Now I’m not saying this is easy.

It’s not.

No one likes to send off a complete article only to get it back with track changes all over it.

But in the beginning, I often felt that once I submitted an article it was done.

And sometimes, it was.

But sometimes I received requests for more information or changes, and because I saw those as criticisms, my confidence was knocked.

Now I realise that it’s all part of the gig.

I now expect and even welcome feedback.

And now I see it as a way of working with the editor or client to produce an article that really works for the readers.

Saying no creates space for what you really want to do

It’s taken me a long old time to learn to say no.

I’m still working on getting that simple word out more regularly, but in the last few years I’ve said no to all kinds of things.

No to low-paid work

I’ve knocked back press trip offers

I’ve said no to interviews and speaking opportunities

Refused to commissions from editors

No to networking events

And even though this may all sound very negative, by saying no, I’ve created space for what I want to do.

Saying no to low-paying work means there’s space to accept or pursue high-paying gigs.

Saying no to press trip offers has meant more time with my family or not going on a trip simply because I’m flattered to be asked.

I’ve said no to speaking opportunities if I don’t think the audience will get value from my message. Or if I think the investment would be too great from my perspective.

It’s taken me years to get to this point.

But I can see what a dramatic impact it’s had on my business.

I only wish I had started sooner.

Give people the benefit of the doubt

It can be isolating being a freelancer and I think sometimes that time we spend by ourselves can mean we create stories not only on the page, but in our heads.

It’s easy to think things like:

My editor hasn’t replied, they’re ghosting me, they hate me and my work.

My editor has requested changes or edits, they’ll never want to work with me again.

A client doesn’t have any work for me this month, they’ve found another better writer.

An editor says ‘I’ll keep your idea on file”, they won’t.

I’m as guilty as anyone, jumping to conclusions about people’s motivations.

But in most cases, I’ve found that there’s a reasonable explanation for their behaviour.

And the truth is, we don’t have any control over how people respond to us, our articles, our LOIs or our pitches.

I wish I had known before I began freelancing that there’s usually a side to the story that I haven’t considered or thought about before.

And that goes for the stories I’m writing too.

What about you? Is there anything you wish you had known when you were starting out as a freelancer?


  • Tracy Kaler says:

    Thank you for writing this post! I can so relate to all of it. Life as a freelancer is tough, but you have to be on the five or even ten-year plan for it to pay off. At least, that’s what I’m counting on. 🙂 And I am so glad that I’m not alone in procrastination and tech distractions! Maybe in 2020, I will conquer those two evils. Happy New Year!

    • lindyalexander says:

      Thanks so much Tracy, yes, I think a 5 year vision is a good one to have 🙂
      Let’s conquer the two evils together this year!!

  • Lauren says:

    This is a helpful post.
    I’ve been freelancing (mostly) full time since September and have only had one commission so far. ( I also had content work and I need to get new clients). Some days it feels like a black hole. Some days I’m super motivated and others, I really question “Why I’m doing this and if it will ever take off?” I know I must be patient and persistent. I also have to trust that when I get rejections that say, hey not a fit but please keep pitching, that it’s a good sign. Alas, It will be interesting to see how 2020 goes for me.
    Thanks for all your posts and keeping things honest and real. It makes all the difference!

    • lindyalexander says:

      Hi Lauren,
      Thanks for your comment. I know those feelings of super motivated vs the black hole well! One thing that really helped me (and helps me still) is having a few freelance friends that I text or message throughout the week. We check in on each other, talk about what we want to achieve and I’ve found that really helps.
      But yes, it’s absolutely a great sign if you’re getting feedback that says ‘keep pitching’. I’m sure it won’t be long until your patience and persistence pays off.

  • JoAnna says:

    I can relate to all of these! Something I wish I’d known when I started freelancing about 5 years ago was to be very clear on what services I do and don’t offer. In the beginning, I offered writing services that I had experience doing, but didn’t enjoy doing. Fortunately, I didn’t get any queries from potential clients about those services. But, after a year or two of freelancing, I revamped my services to offer only what I was passionate about and enjoyed doing.

    • lindyalexander says:

      Oh, that’s a great point JoAnna, thank you. It’s great that you’ve been able to run your business writing about what you love. For me, if I have a dull feeling in my gut (or a feeling of slight dread) when I see a proposal from a client, I know it’s not a good fit. I’ve only recently started saying no to that work though. It’s a bit of a work in progress!

  • K. Wright says:

    I also can relate to all of these, especially the points about being patient and responding to feedback. I struggle with patience and feel so defeated when I put in lots of work and don’t see results right away. And I just got edits back from an assignment and felt pretty bad since it essentially meant having to rewrite the entire piece. The logical part of me knows that patience and feedback are part of the process but it’s still easier said than done most of the time.

    It is comforting to hear from a long-time freelance writer who has been through most of what I’m experiencing. I hope to get better at being patient and accepting feedback over time.

    • lindyalexander says:

      Yes, you’re so right. It is easier said than done. And as I read your comment, I also just received feedback on an article for a corporate client which means I have to go back and interview another person and make some significant changes. It does sting and at times it can make me question if I’m really cut out for being a writer or doing a particular kind of work, but those thoughts soon fade when I put the feedback into action. I think the more feedback we get the better we are at accepting it, it’s where the learning is and my focus is on actioning their comments as soon as I can. Good luck and I hope your piece isn’t too onerous to rewrite.

  • Lana Wildman says:

    These are all excellent reminders–thank you! In regards to receiving feedback, it’s been helpful to learn to sort client preferences and general pissy-ness from genuine “better writing” suggestions. Like all of us in some manner or another, some clients fixate on odd things, like never, ever using certain words, or never accepting something with certain categories flagged by their favorite grammar checkers. I fix to suit, keeping in mind that these fussy rules are entirely subjective and my next editor probably won’t even notice the same “crime”. And some clients, I find out too late, are perpetually in a bad mood and don’t like anything. But real objective evaluation is priceless, so even while I squirm and soothe my pride, I try to soak in what they’re telling me.

    The long view is my current struggle. I think I’m heading the right direction now, after having done less than helpful things for too long. I will persist.

    • lindyalexander says:

      Lana, I had to smile when I read your comment about ‘general pissy-ness’ and I totally agree. That’s a great point you raise about keeping in mind that what works for one client, isn’t necessarily going to be the same for the next. Thanks for your comment – I find I’m always evaluating where I’m going and what I’m doing, but sometimes it’s good to be on autopilot just for a bit and take the short/middle view 🙂

  • Jenny Bioche says:

    Ok thank you I am normal. I had a healthy freelance writing career in the 90’s. Then came the web, and my third child, then a fourth and I hung it up as my family required my time and energy. With an almost empty nest, and failed dabblings in “real jobs”, I have been exploring getting back into freelancing. My first pitch was to a regional magazine, of a region where I used to live, editor contact came through a writing friend who wrote for the mag regularly. Full blown rejection with great “feedback”. I licked my wounds, took this summer off to take writing classes, memoir master class, but THANK you Lindsey as this is encouraging. The long play, the 5 year idea. I figured if I wasn’t back and cracking within 3 months it was useless. It’s all about deciding, pitching, and the patience. Will keep you posted on my progress. Big hugs from the US. Jenny B

    • lindyalexander says:

      Hi Jenny,
      Thanks so much for taking the time to comment. I love that you accepted that feedback and took action with your classes. 3 months is a short time in freelancing – I think of it like turning around a huge ship – it’s going to take time, but you’ll start heading in the right direction soon. And yes, please keep us up to date with how you’re going!

  • John says:

    Hey Lindy. I have been freelancing for over 20 years. Whenever anyone asks me what’s the first thing they should do when they go out freelancing, my response has always been – “see your accountant.” This is a business you’re about to enter into and so you need to know some business basics about what you are about to embark on before pitching for new work. You also need to know the many ways the tax system can benefit the way you work.

    • lindyalexander says:

      Hi John,
      Thanks so much for your comment. What great advice, and very prescient as I’m just about to look at getting a new accountant who really ‘gets’ freelancing!

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