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How to work out what’s holding you back

By May 27, 2020 10 Comments

When you think about your work as a freelance writer, can you easily identify what it is you lean on? Do you know what I mean by that? I mean: what’s your crutch? What’s holding you back? What’s the thing you use for support or reassurance that might have helped you at the beginning of your freelance career, but may not be that useful to you anymore?

Before I dive into the crutches of freelance writers (goodness, I have to be careful not to write crotch!) I want to tell you a short story about one of my crutches.

As lots of you know, I took up running a little while ago.

Okay, when I say I took it up, it sounds like I’m running a marathon every second weekend.

Believe me, I’m not.

When I started running, I loved the idea of exercise, but the reality?

Not so much.

But as I approached a milestone birthday I realised I needed to do something active.

Long story short, I took up running.

Very slowly. In every meaning of the word.

I started out with an app AND a running playlist on my phone.

Because heaven forbid I could just go for a run with only my thoughts and determination to keep me going, right?

Anyway, for about a year I used the app.

It got me to the milestone of running 5km.

But I always struggled with motivation and wanting to quit.

It was too hard. I was still too unfit. The hills were looming and I hated them. 

I looked at the numbers, the distance, the pace and I compared myself to friends who ran and who cranked out 5km in 20 minutes, when I was barely managing to get home in 35 minutes.

Then one day my running armband broke.

I told my partner I couldn’t possibly go for a run without it.

“Just try,” he said.

(And, as a side note, can I just say that he IS the kind of person who could run a marathon every second week without even getting puffed so I wasn’t too keen on taking his advice).

I tried to explain that I needed my armband, I needed my new program that told me to keep going, and told me how long and how far I’d run.

But I was wrong.

Completely wrong.

When your crutch doesn’t help you

I went for a run without my headphones in my ears and without my phone in my armband and I was totally surprised by how it felt.

I felt free.

This time, I ran longer (I think) and faster (I think) – and for the first time, I loved the run.

I thought I needed my app and the armband to keep me going, but in fact it was holding me back.

Okay, I hear you ask, but what the heck does this have to do with freelance writing?

A lot.

In my work with freelance writers over the years I’ve seen loads of writers using crutches that they’ve outgrown.

It’s helpful to use scaffolding at the beginning to help us reach our goals.

We might use a pitch template, sign up for a newsletter or join a Facebook community to give us guidance.

But sometimes when we reach our goals, we keep using these same tools or information, even when our goals change. 

And actually, we end up dragging our crutches behind us, rather than them helping us get to where we want to go.

Do you recognise any of these examples?

I see (and I’ve experienced) lots of freelance writers with different crutches, like:

  • You want to break into different publications, but you pitch the same, old magazines, newspapers or online sites because the editor knows you. Your crutch: It’s safe, comfortable and you’re not sure where else to pitch.
  • You’re making a little bit of money from your writing, but you just can’t seem to get any traction. Your crutch: Your wheels are spinning – you’re reading blog posts, listening to podcasts, doing courses, and accepting low rates because that’s all you’re being offered. You’re splitting your attention in a million different directions, unsure of what you should be focusing on. 
  • You craft beautiful pitches that editors show interest in, but if they ask for more information or for you to follow up when they have budget, you don’t. Your crutch: You’ve done the hard part (writing the pitch) but you hold yourself back from seeing it through. 
  • You love writing and have had success, but you’re not sure what to do next. You could try something new (either find new clients, try a new niche, look into corporate writing), but you don’t. Your crutch: You’re being held back by a (perceived) lack of time, procrastination, technology or a loss of passion for what you’re doing.

These are just a few crutches that I see amongst freelance writers.

But please don’t think that I’m judging you, because I’m not.

We all have crutches that we lean on and that become our habits.

I certainly do.

I know that one of my crutches is that I’m looking for comfort – I like writing for editors and clients who come to me (who doesn’t, I know!) but it does mean that I don’t spend as much time marketing as I should.

How to discard your crutch

The key to being a successful freelance writer is working out what’s holding you back from the next step.

Because that’s all you have to take.

The next step.

Even though you may have ambitious plans or annual goals you want to hit, all you can do is the next step.

So, what’s the next step for you?

For most of us, it’s thinking about what you might be leaning on too heavily and how it may be holding you back.

It’s not always easy to recognise what is helping and what is hindering us, so take some time to notice your habits and your thoughts about certain things.

For example:

When you go to send a letter of introduction to a potential client, what are you telling yourself or what are you thinking?

When you think about this time next year, what thoughts do you have about your freelance writing career?

What are you reluctant to do in your business?

Recognising these kind of blocks is the first step in standing up and letting go. 

Do you have a crutch that you’re leaning on? Have you managed to work out what’s holding you back?


  • This blog post couldn’t have come at a better time for me! I am working at a call center full-time and building a freelance writing business on the side with the goal of replacing my corporate income within the next 4 months. My biggest crutch is a perceived lack of time and holding myself back from seeing my pitches through. I even got an email about writing a guest post for Freelancer FAQs from Elna Cain herself but I haven’t responded with my blog post idea yet. It’s been almost a week. I am going to be writing back to her after I get off of work with my idea so I can move forward toward my goal, one step at a time. Thank you for the motivation, Lindy! I needed it more than I realized I did!

    • lindyalexander says:

      Ah Lisa, I’m so glad this post gave you some encouragement to keep going and take the next step. Definitely get back to Elna and let her know your idea – check in and let us know when you’ve done it and we’ll give you a virtual cheer 🙂

  • As I’ve mentioned in earlier comments, I’m still finding my feet in the freelance writing field. However, your timely post is just as salient to the beginner as it is for those further along the trail. 

    “We must use time as a tool, not as a crutch.” John F. Kennedy.

    It occurred to me, as I read your post, that a question I should probably reflect on more often is to ask myself, as I’m about to do something as a freelance writer,  if this activity is going to become a ‘crutch’ and how will I manage it. Your running and writing examples are excellent illustrations of this point. 

    Over the past few years, I’ve become more-or-less familiar with all of the literature in the productivity field. From Stoic philosophy to Seven Habits of Highly Effective People to the lastest NYT best-seller self-help guru. I suspect a lot of this reading has flipped over into crutch-realm. However, I have tried to adopt the following:
    – working to a system rather than some motivational goal.
    – scheduling my time and avoiding to-do lists
    – In the words of Sam Beckett, “fail, fail again, fail better”. 

    So I’ll continue to think about and reassess all those things that are holding me back professionally. The crutches that arrive like some annoying uncle who doesn’t know when to leave. They include over-checking for emails, networks, how I work with and source clients, professional courses, working with deeper focus, following through from pitch to final draft, podcasts and other distractions, time management, health, and so on.

    Sift through those habits, Work out which is a tool, and lose the crutches.

    • lindyalexander says:

      Thanks Richard, I always enjoy your thoughtful comments. I know that annoying uncle well 🙂
      A few years ago I tried to implement a ‘touch it once’ policy – where you don’t check email, but you process it and deal with it right there and then – but I gave up after a while. After reading your comment, it might be time to try again.
      It sounds like you’ve got a really good balance and are well aware of any potential crutches.

  • JoAnna says:

    Fantastic article! For me, I’ve become very settled in my writing niche: pet owner education. I have steady clients who pay me what I deserve, so it’s an easy crutch to continue doing only that type of writing. I’ve been wanting to do more human health writing, and have a great client in that area (yay!), but haven’t devised a strategy to reach out to other potential human health writing clients. My goal is actively to diversify my writing clients and breathe new life into my writing interests.

    • lindyalexander says:

      That sounds wonderful JoAnna, and how great that you’ve already got a stepping-stone client in the human health area. You can definitely use this to diversify and maintain your passion for writing.

  • Helen Iatrou says:

    My quarantine brain has had me splitting myself in so many directions but mostly reading article after article, rather than getting my head together and crafting a pitch or LOI and sending the damn thing. Now I realise that I just have to dedicate each day to one thing and focus on that. Thanks very much for this, Lindy!

    • lindyalexander says:

      Oh Helen, I hear you. I think putting the blinkers on and focusing on one thing (even if it’s for 30 minutes) is going to help move you in the right direction. Go well!

  • This is such a GREAT post Lindy! Lots of food for thought. When life is so busy, sometimes it’s hard to see the forest for the trees. Good to take a moment to pause and reflect.

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