CASE STUDY: What I’ve Learned About Freelancing

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Last year, I was delighted to share a HomeWorkingClub success story about Lyn McNamee. An ex-teacher turned freelance writer, Lyn is a “graduate” of my Freelance Kickstarter course, and is now a well-established freelancer working entirely on her own terms.

I commissioned Lyn to write this article, looking back on the things she’s learned about freelancing over the past few years. I’m sure many readers will find some very interesting insights here!

Over to Lyn!

More than ever before, now is a great time to be a freelancer. While layoffs loom in many traditional industries, freelancers seem busier than ever. Globally, it’s estimated that around 1.57 billion people are self-employed or freelancing — something I had no idea about when I joined the ranks in 2020. 

I procrastinated about quitting my stressful teaching job for years. Then, when the world locked down, I decided, “it’s now or never.” I’ve never regretted that decision.  

Even though I was a freelance novice, I had a fair idea of what to expect in those first few months, thanks to joining the Freelance Kickstarter Course. But, of course, putting theory into practice takes things to a whole new level. Now, two years on, I’ve experienced first-hand the many joys (and a few downsides) of freelancing. 

If you’ve been sitting on the fence, wondering whether to leap into the freelance world, this article may help you decide. 

Freelancing is fun, flexible and frustrating

One of the best aspects of freelancing is the freedom to travel. If I want to hop on a plane and visit my grandchildren for a week, I can! It’s just a matter of packing up my laptop. 

On the other hand, I take my laptop everywhere, and there are very few days when I’m not writing, no matter where I am or who I’m with. Occasionally that means socialising during the day and typing half the night to keep on top of the work. 

Some jobs are pure joy. You love the subject, the client’s a dream, and the pay is terrific. But freelance work can be relentless, too. When there’s a deadline looming, you can’t stop because it’s 5 o’clock; you must keep going until it’s done. If that means you’re still working at midnight, so be it. 

And crucially, you can’t let the quality drop just because your client has thrown up a heap of extra work at the last minute. (True story!) 

Flexibility also means choosing when and where I work each day, which is a huge bonus.

In summer, I go cycling in the morning and write in a shady spot when the temperature soars in the afternoon. And in winter, the reverse is true. I can down tools and get outside whenever there’s a break in the weather. 

Lists and routines save the day

Flexibility is great, but having a routine is crucial, too. You can easily waste a whole day going down rabbit holes on Google. Then there are video games, social media and people who think you’ve got heaps of free time because “you’re at home all day doing nothing.” All those are excellent timewasters but terrible for productivity.

Establishing a routine that suits your energy levels and lifestyle takes care of all that. You can ring-fence work time and respond to requests outside of that. 

I’m obsessed with lists because they keep me on track with work and general life. Creating a list sets you up for the day, and I love ticking off the items and seeing that visual confirmation of all I’ve achieved. 

Each night I list the next day’s tasks for writing, fitness, meals and even meeting friends or housework. Some people prefer a morning plan, but I like the evening. It helps get all your “must do that tomorrow” ideas out of your head and onto paper. I sleep better knowing I won’t forget something crucial overnight. 

It might seem strange that I include horrible housework and fitness in my lists, but when you’re working at home, it’s easy to get lost in one task. Scheduling them means I get up and move regularly and have some variety throughout the day.

HWC has heaps of good advice on being productive at home, so check them out if you find that time runs away. 

I don’t mind paying Upwork’s fees

Growling about Upwork fees is a favourite pastime for freelancers. Upwork charges you 20% of the first 500 USD you make with each new client. And when you’re getting started on the platform, you pay for Connects too. That’s because each job application costs between two and eight Connects.

These fees do seem harsh when you’re just getting started. However, once you hit the $500 mark with a client, the payments drop to 10%, which doesn’t seem nearly so bad. 

I don’t mind paying to use Upwork’s platform and services. They bring me lots of clients, sort the money and give me a safe place for messages and files. 

Being on Upwork has helped me start a successful freelance career. The HWC Freelance Kickstarter Course devotes a whole section to the ins and outs of Upwork, and that’s a massive bonus for anyone new to the game.

Don’t take rejection personally

Rejection is a fact of life in freelancing. You can spend ages perfecting a response to a job on Upwork and not score an interview. Or you send an enticing pitch to an editor, and back comes a “no, thanks.” 

And when you do win a job, it takes a bit of time to gel with the client. Sometimes they love what you’ve done straight away. But other times, you get lots of notes or corrections, or they ask you to do things differently next time. 

Everyone makes mistakes, especially when you’re new to a job, so I know they’re not a reflection of my writing skills. Instead, I take everything as an opportunity to learn and improve for next time. I’m grateful that many clients have taught me new skills and given me time to understand them.  

Sometimes I’m lucky enough to work with an editor, and that’s pure gold. Editors are wonderful. Every time I get an article back with suggestions for rewrites or edits they’ve made, the changes seem so obvious I wonder why I didn’t see it before. 

Not knowing my niche turned out to be a bonus

There’s a lot of advice out there about working in a niche. That’s great if you know about in-demand stuff like technology, finance or health. I don’t! 

So, instead, I looked for jobs where I’d learn a lot and have fun doing it. 

That means I’ve enjoyed a wide variety of work over the past two years. For example:

  • I’ve written a non-fiction book and some children’s stories 
  • Created video scripts and written courses
  • Written newsletters  
  • Learned how to research articles and write listicles and product reviews 
  • Listened to countless podcasts to repurpose them as articles 
  • Turned a PhD thesis into a series of articles for an education website
  • Dissected a self-help book and distilled its advice onto a set of game cards. 
  • Interviewed fascinating people to learn their story
  • Written four magazine articles 
  • Created website copy and a sales page
  • Learned three different content management systems for various blogs 
  • And I’ve worked on three enormous online summits. (That meant watching hundreds of interviews and summarising their content, which the organisers then sold as a book.) 

Many jobs are one-offs. You do the work, get paid and never hear from the client again. No problem. But other clients offer regular work, and others return at intervals or recommend you to their friends and colleagues.

Every job adds experience and expertise and builds confidence to keep learning, say yes to new opportunities, and raise your rates. 

I was thrilled when I landed my first-ever client on Upwork. He paid the princely sum of $10 per article, and it took me hours and hours to research and write each one. I’ll always be grateful to that client for taking a chance on me. 

Fortunately, I don’t have to write $10 articles anymore. Nowadays, my clients pay $120 to $300 for a web article and more if the article is published in print. 

One thing that hasn’t changed — I still take ages to write a good piece. Sadly, I don’t think I’ll ever be one of those writers who churn out a blog post in a couple of hours.

You can kickstart your freelance career at any age

Freelancing has changed my life. I love setting my own hours and working to my own rhythm, but even after two years, I’m really just getting started. How many 60+ year-olds can say that about their jobs? 

But here’s the thing. My clients care about their work, not my looks, so my age hasn’t been an issue. So long as I’m approachable and produce great work on time, they’re happy, and so am I. 

So, what about you? Are you stuck in a rut and wondering how to change your life? Looking at retirement but still want an income? Tired of the corporate rat race? Could freelancing be the answer? My experience proves you don’t have to be an expert to get started.  

You do need determination, courage, and a willingness to learn and grow. You’ve got those skills, for sure.

Put your dreams into gear and kickstart a new career today. 

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