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I Spent $100,000 on Upwork… Here’s My Advice for Freelancers

By Margaret Manning November 17, 2018 Managing Money

On the surface, freelancing sounds like an ideal option for older adults looking to make a little extra cash. It’s something that you can do from home, it allows you to leverage the skills that you earned over the course of your career and, for the most part, ageism is avoidable.

The reality, as many of the people that I have worked with have learned, is somewhat more complicated. I know some freelance writers and developers who make north of $100,000 per year. I also know ten times as many people who have earned next to nothing.

Over the last 10 years, I have worked on both sides of the freelancing fence. I have worked as a freelance writer, mostly to pay the bills while Sixty and Me became a viable business. I have also hired plenty of freelancers, spending more than $100,000 on web developers, writers, editors, researchers and virtual assistants.

Now, I would like to offer some advice for all of the people in our community who are just at the beginning of their freelancing adventure. Here’s what I learned by spending $100,000 on sites like

Don’t Try to Please Everyone – Stand Out!

Many people think that freelancing is a numbers game. They believe that you need to apply for 100 jobs in order to get responses on 10 and, hopefully, get to work on 1. What nonsense!

When I was working as a freelance writer, I was accepted for the majority of the jobs that I applied for. Was I smarter than the other applicants? No. Am I a better writer? Definitely not, although I do love to write!

The truth is that I stood out. I knew what kind of writing I wanted to do and the specific niche that I wanted to play in. Then, I did everything that I could to stand out.

Other people looking to hire a freelancer may disagree but nothing makes me pass over an application faster than the words “I can write anything.” Ok, that’s not entirely true. I usually look at the person’s writing samples (if they bother to send them!) Occasionally, I come across someone who genuinely is a writing prodigy. But, this is the exception, not the rule.

Even if you can “write anything,” you should tailor your response to the specifics of the project. Imagine what it’s like to look through 100 applications that say the same thing… “I’m fast, I can write anything and my writing gets results.” Don’t be the same as everything else! Stand out!

Don’t Sit Still – Start Doing the Job You Are Applying For

I’m always amazed by the number of writers who apply for projects and don’t have any public writing of their own to show off. Oh, sure, some of these applicants will have sample articles that they have written for other clients, but, most of them don’t have their own website.

If you are going to be a freelance writer, get up every day and write. If you don’t have any projects on a particular day, force yourself to write one, two or three articles on topics that you are passionate about.

Setting up a WordPress site is free (or $2.99 a month if you want a custom domain name). So, why in the heck wouldn’t you do what you say you love?

Side note: no-one wants to be a freelancer forever. Starting your own blog (or blogs) is one of the best ways to start your own business without a significant financial investment. Does it take time and effort? You bet! But, along the way, you will build a killer portfolio, find your voice and develop your own personal brand.

The same logic applies for freelance developers, designers and any other category of freelancer. That said, in my experience, people in these categories tend to be more likely to work on their own projects while they are waiting for freelancing work.

Take the Time to Respond to Jobs Properly

I delete more than 60% of the project applications that I receive on Upwork without even reading them. Why? Because they are cut and paste responses that make it clear that the freelancer in question didn’t even read the project brief.

Have some respect for yourself and the client and only respond to jobs that you are genuinely interested in taking on. It doesn’t take long to customize your standard pitch with a few words about why you are a great fit for a particular job.

Even if you are not an “expert” in a particular topic, chances are you can find a “hook” to catch the hiring manager’s attention. Likewise, if the contact at the client uses their name in the project description, why not address them by it in your response. These are small things that make a big difference.

For Goodness Sakes Have a Picture on Your Profile

Enough said.

Go Above and Beyond the Call of Duty

Once you have landed a freelancing job, do everything in your power to be helpful. I can’t tell you the number of times that a simple article project has turned into a longer-term and more strategic relationship.

Here’s a real example, a few years ago, before I started Sixty and Me, I took an article writing job with a technology company based in Washington state.

The original scope of work was to write a series of 10 articles for the company’s blog. I had an idea for an 11th article and wrote it for them for free. They were so happy with the results that they asked me to write 6 articles a month, which I did.

About 3 months into the project, I noticed that some of the articles that I had written had not yet been posted to the blog. I asked my contact at the company if there was anything that I could do to help. He told me that the problem was that they didn’t have anyone to manage their WordPress site. As a result, he ended up posting himself when he had time… which was rarely.

Since I managed my own WordPress blog, I offered to put together a proposal for looking after the blog for them. This would involve writing the articles, posting them to the site, finding licensed images to use, monitoring the site for spam, providing monthly reports on traffic and several other tasks.

The client was over the moon and accepted my proposal almost immediately. I also could not have been happier. I genuinely liked working with this client and since the work was more strategic than just writing articles, I was able to charge a premium for my services.

There are 100 smaller tips that I could give about “always getting everything in writing” or “letting go of clients that just aren’t fun to work with.” But, at the end of the day, if you follow the big picture advice that I have laid out here, you will do just fine!

One last thing – don’t ever let anyone tell you that you are too old to be a freelancer or that there is too much competition from millennials. When it comes to freelancing, your age and maturity are actually strengths. Why? Because, in my experience, you will be more likely to actually follow the advice in this article!

Whether you are a freelance writer, developer, editor, designer, virtual assistant or something else, I wish you all the best as you start your freelancing career.

Have you ever considered freelancing? Why or why not? What advice would you give other freelancers who are just getting started? Please join the conversation!

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The Author

Margaret Manning is the founder of Sixty and Me. She is an entrepreneur, author and speaker. Margaret is passionate about building dynamic and engaged communities that improve lives and change perceptions. Margaret can be contacted at

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