It’s nearly two years since I started freelancing. I was asked the other day how I got from my first steps as a freelancer to running my own business. It’s quite strange to look back at when I started out, and to reflect on how I got to where I am now. It wasn’t always easy but over the past two years I’ve not only become a successful freelancer but I’ve improved my confidence and quality of life.
I wanted to write this post because I remember how scared and nervous I was when I began. I was constantly anxious, filled with self-doubt. I had zero confidence, and I looked around me and saw all these successful people and convinced myself that it would never be like that for me. I was sure that there was some magic formula to being a successful freelancer or businessperson, and that for someone like me it just wouldn’t be possible.
But it was. Here’s how I did it:
How it Started
I started out on Elance, a website where clients can post jobs and freelancers can bid on them. At the time I was working in a restaurant doing admin and books, trying to pay my way through my Masters degree. I was totally unhappy in my job and I wanted to have more control over my means of earning a living. With a Philosophy degree and MA, I knew that there wasn’t many jobs out there. And anyway, I hated working for other people. I was sat in my office one day, faffing around, and I came across Elance. I spent ages worrying whether it was a good idea. I was sure that no one would want to hire me. After all, I lacked any portfolio or freelancing experience. Who would want to hire me over people who had loads of experience? In the end I thought “Fuck it, what’s the worst that can happen?” I signed up, made a profile, read a bunch of articles on bidding on Elance, bid for a job and (to my surprise) got it.
Bidding on Elance

The thing about Elance is that there are always people looking for cheap labour, but equally there are people looking for quality labour who are willing to pay for it. I got my first break from Hampton Catlin, a developer who was looking for some content for a project. Lucky for me my zero star rating made no difference. He said he was “a sucker for giving someone a start” (he’ll always have a special place in my heart for that). Hampton was fun to work with and he loved what I did. This was a massive boost to my confidence and I felt ready to bid for more jobs.
Here are some tips for building your profile and bidding on Elance.
In case you’re interested, here’s that first job I bid for, along with my bid.
Hampton’s job:
I’m looking for a writer with good explanatory writing skills and is very competent with computers. I’m looking to have a series of articles produced that help non-technical users understand about preserving family photos. I am running a website that allows users to upload their family photos for longterm storage and so I’m looking to partner with someone who can produce publicly-viewable articles to drive traffic to the site.
For instance, an article about “How to make images smaller?” or “Why is my photo so huge?” or “Easy ways to cleanup images” or “What is DPI?” or “What DPI should I scan my photos with?”
You need to be computer literate and have Photoshop/Office installed. The articles will need to use both of these bits of software.
Also, I’d love to produce some articles about people losing their family photos or having hard drive crashes. I have a bunch of people to talk to about it off a HARO request.
This project may be a long term project depending on quality and popularity of output!
My bid:
Most of us, at some point in our lives, come across a massive box of family photos that has to be dealt with. Recently my boss dumped a huge box on my desk and told me to start scanning. There were recent photos, photos from the turn of the century, photos from England, photos from Poland. Many of the photos have been sat at the bottom of a box for years, many are damaged and need to be touched up. But I love photographs, I love the nostalgia and sense of the past that you get when going through a box of old photos. Luckily I love Photoshop as well and it is a perfect tool for preserving the past.
Trained in advanced Adobe Photoshop use and a confident writer, I’m the perfect person for this job. Examples of articles that I can produce would be:
– Should I bulk scan my images? – How to batch crop and straighten in Photoshop. – How should I organize and store my images? – What does “resolution” mean anyway? And why is it important? – The importance of backing up. – Using the clone stamp tool to touch up damaged images. – Now I’ve got all these images on my computer on my computer, what can I do with them?
I would absolutely love to write about people who have lost their family photos, whether through hard drive crashes or other means. I’d be happy to carry out interviews to do so. Another angle could be some articles on the phenomenon of boxes of discarded family photos showing up at flea markets and on Ebay.
What I can offer you: 1. High quality, proofread articles; 2. A light and friendly tone that will engage your reader; 3. Articles produced on time, with screen grabs from Photoshop if required; 4. A good working relationship; 5. Full dedication to your project for its duration.
Please refer to my portfolio for examples of my work, and to my website: www.siobhanmckeown.com
The Next Step
About 6 months of doing piecemeal work on Elance for lots of different clients, as well as doing my MA and working a part-time job, I virtually met James Farmer, who needed to blog at WPMU.org. I had been working with WordPress for a while, mostly as a hobby but also building the occasional client site. I knew even then that making good money from writing fiction, or even about arts & humanities, was a dream. Even bestselling authors don’t make that much money. Because so many people want to do it, the pay is incredibly poor for that type of work. But I could, I figured, write about WordPress.
I think that this is something that people who start out freelancing don’t realize. You don’t only have to use your career skills, you can use every skill you’ve got. WordPress was a hobby, it became a job. Don’t be afraid to use anything you have experience in as a freelancing skill. You don’t have to be paid at something to be good at it. I started blogging for WPMU.org with a few posts a week, but this quickly increased. After a while I was brave enough to ask for a pay raise (which I got) and then got another raise after a post that went viral. At the same time I kept on other clients who were bringing in steady income, most notably writing regular articles for Wix which provided me with steady income for months.
Quitting the Job

The jump from person with job who freelances on the side is a terrifying one. I can’t stress how much I hated my job. It made me totally miserable. I hated going in, I hated my arrogant boss who always thought he knew best. It made me feel like shit to sell my labour power to such an idiot. Despite things going well with freelancing I still needed that security blanket of a steady income. At the time I was working around 50-60 hours a week between freelancing gigs and work.
I had a particularly miserable experience just before Christmas in 2010. My office was at the bottom of a cliff by the sea, with a steep path through some woods going down to the sea front, or a windy road. When it snowed it was a nightmare to get to. We had particularly heavy snow one night. No one could get to work; all the roads were closed. But since I lived nearby I could walk. So walk I did. When I got in I said to my boss that I’d appreciate it if I could leave before it got dark as it was going to snow again and the path had been treacherous on the way down. He fumed at me, saying that he didn’t care about me, that I wasn’t going anywhere and basically I should fuck off to my office. Given that I did admin and there was no admin to be done, I had nothing to do but sit in my office, in the freezing cold (no double glazing), watching out the window as the snow fell over the sea. I nearly walked out.
The next week I went on holiday for three weeks. I freelanced the whole time and was totally flat out. When I went back to work after Christmas I managed 3 days before quitting. It was the biggest relief I’d felt in a long, long time.
Working a job you aren’t fulfilled by, or don’t care about, sucks, but working for an asshole in a job you aren’t fulfilled by is even worse. There are ways out of it. When I started freelancing on a whim I didn’t expect to be able to quit my job; six months later I was out.
Getting Comfortable
For the next year I wrote for WPMU.org, and did other things around Incsub. I found myself getting totally comfortable. I loved working there and having a team of people who were so much fun to be around. There were definite low moments, which people in the WordPress community will know all about, but mostly it was great and I made some fantastic friends.
Eventually, though, I started to get the feeling that I’d traded in having a job for having a job. I was working for one company, with the same group of people, but without any of the benefits of being employed (paid holiday, pension, bank holidays, etc). I wrote this up for Freelance Switch so you can read about it there. When the idea for Words for WP dropped into my lap I thought that maybe it was time to set up my own business. I created a Google form and sent it out to some contacts in the WordPress community. I was surprised when the response from many of them was “when can you start?”
Here and Now
In January 2012 I gave up writing for WPMU.org. It was a really hard thing to do, and I was again terrified that I was going to fail. Working there had become its own safety blanket and it was preventing me from going on and developing my own business and career. I was putting all of my efforts into someone else’s business instead of my own.
Now I focus 100% on Words for WP. I work with some fantastic clients in the world of WordPress and beyond, including ManageWP, OntheGoSystems, Sucuri, Piwik, PressCrew and Event Espresso. My client list is growing all the time and I’m always surprised and pleased at the emails that land in my inbox. I’ve recently employed a sub-contractor and am thinking about incorporating and expanding the business. The baseline $45 per hour I earn is considerably more than the $4.50 per article I got for those restaurant reviews. In fact, I work only 30 hours a week and I earn more than ever.
Highlights
I have a clear memory from when I started freelancing: I discovered Smashing Magazine. I loved everything about it – the detail of the articles, their quality, the overall style. I remember thinking “imagine writing for them – it’s a shame that they’d never want me.” Now I write regularly for them, working with super-lovely WordPress editor Jeff Starr. The day my first post went live on Smashing Magazine it was a real milestone. That gave me the confidence to push even further and I started sending pitches to online magazine that I had always loved but been intimated by, including Cracked, Freelance Switch and, most recently, The Quietus.
Two Years On
One of the most important things that this process has taught me is that if you don’t ask you don’t get. That may seem obvious, but I always used to second-guess people (I still do). I would think “they’ll obviously say “no”, why would they want me when they have all these other amazing, more impressive people?” And, if I’m honest, that feeling has not gone away. My most recent pitches for unsolicited work went to The Quietus about two months ago. I spent days in deep anxiety, with sleepless nights, and had convinced myself that they thought I was a dick. I (really) even dreamed about them thinking I was a dick. When they said they’d publish my stuff I danced around the living room, shocked and elated that someone wanted my writing. That still doesn’t go away, because, after all, I care about what I do. I still fear rejection, and rejection still happens. There is always doubt, but the doubt no longer induces paralysis.
The scariest thing when I started out what seeing all of these people who had already, in my eyes, made it. I had no conception of how to get from where I was to where they were. Even a year ago I saw a massive gulf and that gulf made me anxious. It’s not about getting from here to there in one leap, it’s about small incremental steps. I am naturally an impatient person, I want to be doing something right now, or I figure that it’s not worth doing. But starting out with that one job on Elance was the first step, and the rest went from there. And I’m still stepping, so who knows what will come next. I really don’t feel like I’m at the end, in many ways I’m just beginning.
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