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How to Land Freelance Writing Gigs

It’s all about perseverance and networking

Many writers dream of becoming freelancers.

You get the freedom and flexibility that comes with being able to set your own schedule.

You don’t have to sit in rush-hour traffic to get to the office and back— saving 50 minutes each day.

You get paid to learn lots of new things.

And — to the extent that you’re able to land clients — there’s no limit to how much money you can make.


If it were easy to lock down freelance gigs, even more folks would work for themselves.

As it stands today, 34% of the U.S. workforce — some 53 million people — are already freelancers; people who research such things suggest 50% of U.S. professionals will work as freelancers by 2020.

The writing, as they say, is on the wall.

If you want to be a freelance writer, you need to make some moves quickly — before there’s more competition.


Getting clients is definitely hard — but it’s not impossible.

May these tips guide you in your hunt.

1. Get your portfolio and clips in order

First things first: You won’t land freelance gigs when you can’t share examples of your best work.

Before you apply to freelance positions, organize your content and figure out which pieces are your strongest.

Most freelance ads ask you to submit relevant writing samples.

In my experience, hiring managers greatly prefer links to attachments. So publish your prized content online if it isn’t already. Make it easy for hiring managers to see how talented you are by linking directly to your best pieces whenever you apply for a gig.

No one reviewing hundreds of applications is going to fill out a form to access a gated asset.

2. Follow directions and customize your pitches

Imagine you’re applying for a freelance position at a SaaS startup and the ad asks you to submit four relevant writing samples.

Don’t send over two samples you wrote for that awesome company that sells refurbished industrial cleaning equipment (sigh).

Before you submit an application, read the directions to make sure you’re doing precisely what’s being asked. Not only will it prove that you pay attention to detail, many hiring managers won’t consider your application if it’s incomplete.


You won’t land too many gigs if you send the same pitch to every freelance job you apply to.

Every company is different — even those targeting the same customers in the same industry.

Sure, you might be able to reuse some parts of a cover letter.

But you’ll get better results when you customize each message.

Take my word for it: The one-size-fits-all approach is a shortcut that stifles conversions.

I’m not sure how, but these people know you’re firing off the same exact email to a million other companies.

Research each company before you apply. Tailor your outreach to each organization’s specific value proposition and personality. Look to see if they’ve been in the news recently and reference those items when appropriate.

And remember: Double-check your work and then triple-check it.

Sending over a note with glaring typos or broken links won’t impress anyone.

3. Look everywhere, be persistent and get ready for rejection

Even if you’re extremely talented at what you do, it’s not always easy to land a gig.

In fact, the average jobseeker applies for 27 positions before an offer is extended. Believe it or not, studies suggest only 2% of applicants are considered for the average position.

Due to the competitive nature of the business, it may be even harder than that to secure freelance opportunities.

Applying for freelance work, at least to a certain extent, is a numbers game. The more gigs you apply to, the more gigs you’ll get — fractions be damned.

Seek out clients you want to work with — but don’t put all your eggs in one basket.

When you’re starting out, peruse multiple sites each week and apply to everything that sounds interesting.

There are your standard places like LinkedIn, Craigslist and Indeed.

But there are also a number of writing-specific sites like ProBlogger, Online Writing Jobs and Freelance Writing.

You can find even more gig sites with a quick Google search.

Don’t forget that no matter how great a writer you are, clients will decide not to work with you — more often than not in many cases.

Don’t let these rejections deter you from finding the next opportunity.

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4. Put your best foot forward in each interaction

As freelance writers know too well, the needs of any client can change at a moment’s notice.

When that happens, don’t let your emotions get the better of you. Never burn a bridge.

Some of the best opportunities you’ll get will stem from word-of-mouth recommendations.

Do your best to always be pleasant, responsive and reliable.

That way, the people you work with will think of you whenever a friend or colleague needs your services.

Remember, you won’t get every single freelance gig you apply for — quite the opposite.

When you’re rejected, don’t reply with an expletive-filled tirade scolding the hiring manager for making the wrong decision.

Be professional and courteous in the face of rejection.

You never know if the writer the company selects will prove incapable of doing the job — and you, as their second choice, will be given a chance.

You also never know when a client that likes your work but recently had to let you go will recommend you to someone in their network.

5. Convince companies to hire a freelancer instead of a full-time writer

When a company advertises that it wants to add a full-time writer to its team, there’s still a chance you can convince them to try a freelancer instead.

From cost-effectiveness to unique expertise to flexibility, there are many reasons why companies prefer working with freelance writers and contractors instead of hiring full-time employees.

Just because a job ad describes a full-time position doesn’t mean it’s impossible to convince a company to try a different approach.

Don’t be afraid to apply to appealing full-time gigs.

Once you have your foot in the door, try and convince the recruiter or hiring manager to reconsider how they’re going to fill the position.

If it makes sense, volunteer to write a sample blog post to prove that you can do the job.

(In most cases, companies will compensate you for test assignments. But, depending on how much you want a certain gig and how well it pays, you may want to offer to complete a pro bono trial assignment to prove you’re the right person for the job.)

6. Prioritize your own professional development and learn new things

The more knowledge you have and skills you possess, the more attractive a freelancer you’ll become.

Be an autodidactic — someone who teaches themselves. Embrace a growth mindset and learn as much about as many things as you can.

Try new platforms. Follow thought leaders on social media. Keep tabs on your favorite brands to see what their approach to content creation looks like. Find several relevant publications to follow. Use resources like Khan Academy, Codecademy and edX to learn new subjects and skills for free.

For the best results, you first need to learn how to learn.

While you’re at it, practice just-in-time learning so you don’t spend a ton of hours studying up on things you won’t put into use right away.

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7. Market yourself

Freelance writers in the marketing world create content to help brands showcase their products and services. They also write thought leadership pieces to help executives and entrepreneurs market themselves.

Why not use your talent to market yourself similarly?

Use your own brand — You, Inc. — to attract new clients.

Create a brand if you don’t have one.

How?

Build a website to showcase your portfolio (sites like Weebly and Wix are freemium platforms that are quite intuitive).

Use social media to promote the content you write.

Publish blogs to increase You, Inc.’s brand awareness. Use Medium like me. It’s the smoothest publishing platform I’ve ever used.

You can also tap into your own network to see whether anyone you know needs any writing help.

Attend meetups and other networking events to get to know even more new people. You never know when an initial conversation can turn into a long-term lucrative gig.

8. Pursue systems — not goals

In his book How to Fail at Almost Everything and Still Win Big, “Dilbert” creator Scott Adams says that successful people develop winning systems instead of trying to reach specific goals.

Adams defines goals as “reach-it-and-be-done” situations and systems as “something you do on a regular basis with the reasonable expectation that doing so will get you to a better place in your life.”

Suffice it to say he’s no fan of goals:

Goals are for losers. That’s literally true most of the time. For example, if your goal is to lose 10 pounds, you will spend every moment until you reach the goal — if you reach it at all — feeling as if you were short of your goal. In other words, goal-oriented people exist in a state of nearly continuous failure that they hope will be temporary. That feeling wears on you. In time, it becomes heavy and uncomfortable. It might even drive you out of the game.
If you achieve your goal, you celebrate and feel terrific, but only until you realize you just lost the thing that gave you purpose and direction. Your options are to feel empty and useless, perhaps enjoying the spoils of your success until they bore you, or set new goals and reenter the cycle of permanent presuccess failure.

To illustrate: A freelance writer might set a goal of landing two new clients by the end of the month. If that person isn’t able to hit the goal, odds are they’ll be at least a little disappointed.

If they are able to reach their goal, they might celebrate for a bit — until the needs of one of their other clients shifts and their services are no longer needed.

Compare that to the freelancer who has developed a system that involves spending several hours each week looking for new clients.

At best, you’re busier than you can imagine.

At worst, you’re networking with new companies, which — sooner or later — will translate into some amazing opportunities.


The above is more or less the system I’ve been using for the last 2.5 years.

Maybe my system will work for you.

Or maybe it won’t.

You know yourself better than anyone else.

Develop a system that works for you — whatever that might look like.

Then you can live the freelance life you want.

Connect with me on Twitter and LinkedIn.