Side Jobs for Freelancers: How I Kept Myself Afloat in the Early Days

By Chelsea Baldwin, Contributor, on April 5, 2017

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In the early days of my career, I hated this piece of advice: “It’s not what you know, it’s who you know.” I found this particularly irritating because I came from a tiny town in the middle of nowhere and I didn’t know anybody or know of any good side jobs for freelancers. Plus, it was always people from that same tiny town giving me that piece of advice … and they always dished it out with a heavy side of victim mentality. It was said as if I’d be happier and better off if I gave up and resigned to a small town, low-income fate.

But I wasn’t about to accept that advice at face value. So what if I couldn’t land a big city job because I didn’t know anyone? I was going to “make it” one way or another — and for a nobody who knew no one, the internet offered a pretty promising pathway there.

However, when I set out on my own as a freelancer, I had to take some jobs to pay the bills. They weren’t all ideal, but they were all with great clients that helped me network, get to know the right people and build my career to the point of not needing job boards anymore.

If you’re at the point of needing job boards, don’t worry. Here’s how to make them work for you.

1. Find Jobs With Popular Companies You’re 60 Percent Qualified For

A big block most freelancers face in landing good jobs is that they don’t meet all the qualifications. If they don’t have all the “required” experience listed, they don’t apply. Which is a huge mistake.

At one point, I was surfing the job boards and found a job producing a podcast and making YouTube videos. I had years of experience in the kind of marketing talked about on the podcast, but I didn’t know the first thing about editing videos or extracting an mp3 file from an mp4 or editing out background noise.

But, it was a great opportunity, and I was about 60 percent qualified for it. So I went for it and used the next two steps to land it.

2. Make Up for Your Lack of Experience With Enthusiasm

Here’s the truth: 99.99 percent of all job board applicants write the exact same thing in their messages. (I’ve done some hiring for assistants myself, and can vouch for this.) What they write to try to “impress” the person hiring is a predictable formula full of boring words that only makes the reader’s eyeballs glaze over. So write something a little gutsy.

Instead of starting out with something like:

Hi [name],

I’m super interested in your listing for a freelance blogger because I’ve worked in this sector since 2008, and have 5 years of professional writing experience.

Try something like:

Hi [name],

I couldn’t help but chuckle at your requirement for the freelance blogger you want to hire that says they need to know WordPress. (Don’t worry, I was totally laughing with you.)

In my previous role as [job title], we used to work with some freelance bloggers that HR picked out for us, and I swear it actually cost us money teaching some of those guys how to use WordPress before they actually contributed anything.

Do you see the difference? In the first one, you’re just another person desperate for the position. But in the second one, you’re talking with the client cheerfully, as an equal, and you’re saying something memorable.

Here’s a hint: When you speak with them as an equal, you put yourself on equal footing with them. If this is an instance of you not having 100 percent of the experience required, this is crucial to helping you land it. It can even give you a psychological advantage in the mind of the client over someone that has more experience than you. I’ve seen it happen.

3. Reach Out to the Job Poster on LinkedIn

You don’t have to use LinkedIn necessarily, but make sure you reach out to them via a different platform than the one they’ve specified in the job listing. I like LinkedIn because no one actually uses it for its intended purpose of business networking. Sure, you use it to add people you know, but how much messaging and commenting does the average user do there? Almost none. So even though it might take a few days for the client to see your message, contacting them there will help you stand out from the crowd.

All you need to do is copy and paste your original application message and make a few wording tweaks. This step, more than anything else, helped me land those great side projects in my early days — like that podcast opportunity.

Two Big Tips for the Road

Beyond writing a gutsy message and using LinkedIn for more attention, here are two major tips that will help you land great side jobs:

1. Follow the Directions in the Job Listing to a T

If they tell you to use a certain subject line in the email, use it. If they tell you to write, “I love the smell of monkey armpits” in the second paragraph, do that too. Some of them might be outrageous, but they’re included to weed out applicants that can’t follow directions.

2. Be One of the First Applicants, If You Can Help It

At the beginning of a job application process, your client will always be more enthusiastic about it than at the end, especially if they’re using a job board to source applicants. If it’s in your control, be one of the first applicants. This gets your engaging message in front of their eyes before they’re bombarded with a million not-so-exciting messages and helps you stick out in their memory — which really increases your chances of landing the gig.

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