Getting Started on Upwork: A Case Study

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I love sharing stories of success on HomeWorkingClub. Case studies are something lots of readers ask me for, so I’m delighted to share this account of getting started on Upwork.

I particularly love it when advice I’ve provided plays a part in peoples’ success. As such, you can imagine my joy when I saw this post on the site’s Facebook advice group (you can join free here).

Upwork Testimonial screenshot from Facebook

One aspect of running this site that can be rather demotivating is knowing that the advice does work, but that a fair proportion of people read it and don’t act on it. Thankfully, I know that plenty of people do, because many have been kind enough to let me know.

There’s nothing to stop you joining that list of people if you’re prepared to do the work and invest in yourself.

After all, getting as much freelance work as you can handle is a very pleasant problem to have!

I particularly like this case study, because Lyn has built up her freelance business under the shadow of Covid. Regardless of the doom and gloom out there, there’s no shortage of work there for the taking.

With all of this in mind, I contacted Lyn and asked if she’d mind doing a case study interview. I hope it encourages some readers to “pull the trigger” on a freelance career. At the end, I’ve added a few pieces of advice summarising what you can learn from Lyn’s experience.

Hi Lyn, I know exactly who you are, but readers may not. Please can you tell us a little about you and your background?

My husband and I are the classic teacher/farmer couple. He works the sheep farm and until two years ago I taught full-time at our local three-classroom school.

We met when I moved from Auckland (New Zealand’s biggest city) right to the other end of the country. I was only 22 and had no desire to live in a rural life. Moving for a couple of years was meant to be an adventure before I went travelling overseas. But I met a farmer and the next thing I knew we were married and had four children.

I love teaching but I’ve always wanted to be a writer. So, when our first grandchild was born, I decided it was time to start a new career as a writer so that I could spend more time with him. I wanted a flexible career that I could travel with as well.

I still teach one day a week and do a bit of substitute teaching and that gives me a small but regular income. That’s important because it means that I have been able to build up my writing without the pressure of having to earn a living from it straight away. I like moving into it gradually.

How long have you been freelancing?

I started my blog in 2018 and used it to practice writing and to learn about WordPress and blogging in general. If you count teaching part time, I’ve been doing that for two years. During that time, I did a few magazine articles, guest posts and articles for other websites, however I only started on Upwork in March 2020 during NZ’s Covid Lockdown.

What kind of work do you do?

It has taken me a while to find the sort of writing work that I can do. I don’t know enough about computing and software. I hate copywriting and I’m a bit old fashioned for modern teaching websites. There is a lot of work for people who have technical skills (my son-in-law found it easy to get work writing about gaming and stuff because he knows a lot about that).

I experimented with various things – ghost writing a children’s book; writing articles about cameras, lenses and audio recorders for an audio and photography website; My favourite job in those first few months was writing a “how to blog” course based on a book that my client had written. That was a lot of work but used my blogging knowledge and teaching knowledge, so I really enjoyed it.

The main work I’m doing now is writing articles which become the show notes to accompany various podcasts and similar jobs interpreting videos into articles for business clients. I love doing those but each one takes me quite a long time to do. In fact, the length of time it takes me to write a piece is my main limit at the moment.

I talk a lot on the site and on our podcasts about “paying your dues.” Would you say you’ve had to do that? Any examples you can give?

If you costed out the time it took me to research and write those camera/recorder articles (I knew nothing about either thing) I probably did them for about 5c an hour!

I enjoyed writing them but it was hard work for very little money. Importantly though, it gave me experience, proof that I could pitch to and get a client, and practice in research and writing to someone else’s standards and requirements. I had to write in his voice which is very different to my usual style.

Please can you tell us a bit about your experience getting started with Upwork?

I was accepted to the website as soon as I applied. I’ve heard of people being rejected but I didn’t have to wait at all.

I check my job feed regularly. Some weeks there are no jobs that I want to apply for, but often there will be several possibilities.

One of my main criteria is that I think I’ll enjoy doing it and that I’ll learn something while doing it.

Upwork has a lot of helpful information on its website. I am starting to delve into that now because the more you know the better you can use the platform.

Upwork makes it easy to apply for jobs and they keep good records for you. You can make invoices and things for non-Upwork clients too, I think.

What would you say are the bad points about the platform?

It is not fun to lose 20% of your pay each time you do a job. That’s the hardest thing, but I do accept that I’m paying for their services and they give quite a lot. I’m very wary about what I apply for as well. I don’t look at anything that seems like it could be a scam.

A lot of clients use Upwork because they want their job done cheaply. Some of them have totally unrealistic expectations. They want high quality work but only want to pay peanuts.

You mentioned in your comment that you now have as much work as you can handle, how did that come about?

Once I got a few clients that gave me confidence. I learned how to write a pitch that would appeal to clients. I have a portfolio which shows a range of writing styles now. Also some five-star feedback from clients. A lot of them rebook me for other jobs too.

Part of it is that I am not a fast writer so it takes me a few hours to do an article. That’s something I’m working on.

You’ve written a few articles for HomeWorkingClub over the years too. I remember you wrote one on WordPress a long time ago? How did that come about?

I found HWC when it was quite a new site, and it had lots of good advice. I wanted to write but I was incredibly nervous about putting myself out there. Very nervous about being rejected. I procrastinated for months.

Then HWC started running a series which was a case study of someone just getting started on Upwork. What impressed me was the way the guy had pitched you on the off chance. He was brave and it paid off.

I didn’t know much about working from home at that point but I did know what it was like to use WordPress as a beginner and it seemed like a lot of people were talking about blogs, so I wrote a confident pitch about that. Luckily for me you accepted.

What three pieces of advice would you give to a new freelancer wanting to get started?

  • Don’t take rejection personally because you’ll get a lot of it. Just accept it and move onto the next opportunity.
  • Keep trying, don’t give up and keep learning with every job. Each job will give you confidence for the next one.
  • Put together a portfolio that shows what you can do. One of the reasons I started my blog was to get some example pieces. Look for writing that you’ve done in other places too. I adapted some of my lesson plans from school as examples of course writing. I have also included a couple of my best newsletters.

What do you plan to do next? Any specific goals?

I have so many. I would love to write more courses and I’d like to try my hand at ghost writing a book.

I want to improve my note taking techniques and the speed at which I can create an article from scratch. I have written the draft of a book and have some ideas for a series of picture books, so I really need to get onto that.

I have ideas for reorganising my blog too, but that is probably last in line.

How do you cope with home working generally?

Something I thought hard about when I decided to start a freelance career was how to build social interaction and exercise into my days.

I have joined a little fitness club in our area and I make sure I go to a yoga class and a fitness class there each week. We work out but we also talk before and after so that covers both needs.

I go for a walk on our farm each day too. I still teach one day a week and do some substitute work. That is partly so that I get to stay in that world and keep in touch with people there. I also visit various friends and family regularly and I plan to volunteer at some stage.

I tend to write every morning and evening and do other things in the afternoon. I guess the takeaway for home workers is that you need to make sure you don’t get isolated and unfit by staying at home and working all the time.

So, build social interaction, exercise and relaxation time into your days.

Anything else you want to add?

I love the flexibility of working from home. My mum has been ill recently and it is easy for me to take my laptop, jump on a plane to visit her and still keep up with my work.

I think it’s a good idea to put yourself out there in lots of ways. Although my blog is not making money it did get me a presence on the internet.

A magazine editor wanted an article written about one of our local tourist attractions and while she was doing a search on it she found an article I’d written on my blog and approached me to write the article. That was a big boost and led me to pitch them on some other article ideas which they accepted.

You need to build up relationships with people. Do your best work and exceed expectations.

Always be open to advice. Don’t be afraid of editors. I have always found that their advice improves the article and usually teaches me something at the same time.

Key Advice for Getting Started on Upwork (and with Freelancing in General)

A big thank you to Lyn for sharing her experiences. Here are a few key tips that I think many readers could learn from:

Put Yourself Out There

If you don’t ask, you don’t get! Lyn is one of several people who has “cold pitched” article ideas to me. If I think they will be well-written and on a subject that will interest readers, there’s a good chance I will commission them – and the same applies to plenty of publications.

I’ve perhaps opened the flood-gates there! But the key thing is to contact relevant people with relevant ideas. Editors and bloggers get dozens of emails that they ignore every single week, but they do usually at least glance at them all. Make the right suggestions and choose your targets wisely, and you may well get a response.

Pay Your Dues

Regular readers and blog listeners will know that “pay your dues” has become a bit of a catch-phrase for HomeWorkingClub! But this case study proves the point.

The early days of freelancing often mean working for next to nothing while you prove yourself and build up positive feedback. Those who turn their noses up at doing that never get to experience the good bit that comes next.

Concentrate on Work that Inspires You

As I was publishing this post, it occurred to me that Lyn’s not only got all the work she can handle, she’s also choosing what to apply for based on her interests. What a great position to be in after six months!

But it’s a wise strategy that feeds a virtuous circle: Apply for work you’re passionate about > Do it well > Get great feedback > Find it increasingly easy to win more of it.

So What Next?

If you’re inspired by Lyn’s account of getting started on Upwork, there’s nothing to stop you doing the same.

4 thoughts on “Getting Started on Upwork: A Case Study”

  1. This is fantastic! It’s great to see that Lyn has done so well, and I really love the tip about focusing on choosing assignments you enjoy to get more of the freelancing work you love. This is a strategy I’m going to use in October.

    I, too have more writing work than I can handle now. I started working full time in 2018, and like you mentioned, I had to pay my dues. During those early months, I started out in Textbroker. Then I also did an article for you and even several for your wife. I hired a writing coach and moved on to Upwork, where I got several great gigs and clients I still work with today. From there, things exploded. I have regular ongoing monthly work with five clients and I work many many many more hours a week than I should, but I love my life! I suspect you’ve influenced many more people than you imagine, Ben.

  2. Hello Ben

    Great to read Lyn’s case-study, I see many parallels with my own experience @ PPH. I will at some stage chronicle my progress. I do find your newsletters interesting and I’ve referred several others to your Homeworkingclub.

    Les (wardwordy)


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