How To Get Your First Freelance Client On Upwork (Without Leaving Your Job)

by John McIntyre

This is a guest post by Austin Lee. Austin is a freelance copywriter who helps 6 and 7-figure businesses grow sales with engaging email autoresponders. 

That sh*t doesn’t work, trust me.”

From the depths of my parents basement, terrified of returning to the whipping post of the corporate grind — my friend said these deflating words to me over Skype.

He was talking about Upwork, the world’s largest online freelancer marketplace (formerly Elance).

Apparently it’s a hell-pit where poor freelancers go to work for slavelord clients, who pay so little that you’re forced to scrape by on a diet of beans and rice.

Trusting my gut and the research I’d done on this hotbed of freelancing opportunity, I decided NOT to listen to him…

Or any of the other dozens of friends, parents, and well-intentioned people trying to steer me towards safer employment options.

Instead, I learned how to get my first client, create a self sustaining business, and more than 3X my rates in under 6 months, using the ideas I’ll teach you here.

What’s more, you don’t need to quit your job to get started.

So if you want to start getting clients, but didn’t know where to start like me…

Maybe you’ve listened to these common, but completely untrue myths about freelancing on Upwork:

* You must accept $4/hr to compete with labor in India, Philippines, etc.

* You need experience and a thriving network in the industry

* You need a website, and a deep, relevant portfolio of winning copy to land clients

The truth is, once you understand WHAT people are looking for on Upwork (hint: it’s not “expert” copywriters), and how to fill the empty voids…

You can start getting clients quickly, ignore the haters, and start making real money.

How To Get Off The Blogging Hamster Wheel, And Start Earning Faster

Before getting my first client, I spent months studying copywriting, starting a blog, and going balls to the wall in “education mode.”

I learned a TON about the craft, human psychology, and writing sales letters.

But I wasn’t creating anything valuable. And that’s where a lot of newbies go astray.

In fact, I remember reading a guest post on Tim Ferriss blog… and looking back, this advice sounds insane to me.

While I love Tim’s blog, this guest recommended slogging through 9 months of blogging to “build a reputation” and hopefully attract clients.

This sucked me into a black hole of wasted time — where I cranked out tons of work for no money, and wrote blog posts nobody read.

When you get down to the brass tacks of finding your first Upwork client, they won’t give a damn about the book review you wrote about The Ultimate Sales Letter, if you’ve never written a sales letter.

They want to know “can this guy or gal DO the job?”

(Side note: education IS mission critical to your success as a freelancer.)

To learn how to sharpen your copywriting skills for 100X less than a year of college tuition, check out this killer post by John that helped me get started.

In this post, however, I will focus on delivering high quality results in a low-risk, learn-as-you-earn environment)

So how do you go 0 to 60 without blogging your brains out of your ears?

How I raised my rates from $14 to $55/hr in 6 months — without any prior experience

I’ll show you the steps I followed to break into Upwork, without selling my time for pennies, and without building a website or printing a single business card.

You can use Upwork as a launch pad to get a taste of the action, see if you like it, and even keep your day job while you run your test experiment after your 9 to 5 (think of it as your 5 to 9).

Even one or two hours a day of focus is enough to get paying clients within the first two weeks.

Remember, if you’ve ever written a high school essay, a letter to a friend, or a cover letter…

…you can become a copywriter.

In fact, John, along with Ben Settle (email marketing boss), and many others — all agree you DON’T need to be a great “writer” to get good at writing copy (note from John: I dropped out of high school and skipped university, so you definitely DON’T need to be a great “writer” to become a paid copywriter).

Now that we’ve roundhouse kicked the excuses to the curb, let’s begin.

Step 1: Create An Account

Sorry for the non-step. This is as easy as getting a Gmail account, so god help you if you can’t figure it out.

Quick pro tip: find a decent-looking profile picture. If you don’t have one, take a smiling headshot against a white wall.

Upwork is a place to do business — and the fact is, people like to do business with other people, not anonymous profiles.

A nice photo adds a layer of human-ness and professionalism (even if you work in your sweats).

Here’s a good article that shows you how to get a great headshot for free.

Step 2: Select Your Menu Of Skills

In the “My Skills” portion of the profile, choose your focus areas. If you don’t have many skills, no worries — choose the categories you are interested in.

I chose copywriting, sales writing, blog posts, and email copywriting to start out.

The system I’ll describe to you today is tailored for copywriters, but many of these principles can be used effectively in ANY industry.

Step 3: Write A Basic Profile Description

Describe your value. Be enthusiastic. And keep it brief.

Early on, you will likely get started on smaller projects. Given these parameters, clients will be less concerned about credentials, and more interested in the question:

“Can you get the job done?

I’ll show you how to answer that question in step 4.

At this stage, think of your writing as a commodity. Do a killer job, and provide excellent service, but ONLY focus on the essentials — which are:

[+] Applying to, and landing jobs (don’t limit yourself, a broad range of sample categories will paint you as a dynamic freelancer)

[+] Complete the jobs successfully, and on time. Every time.

[+] Get great reviews from your early clients, and keep working for them if it’s a fit (this will lay the groundwork for building into higher paying gigs down the road)

Step 4: The #1 Shortcut To Getting Upwork Clients

This is where it gets interesting, and it’s also where 99% of new freelancers fail.

So, wield this strategy like a samurai sword, again and again, to outcompete freelancers with more experience than you.

The idea is to create hyper-targeted samples, tailored to the specific needs the clients lists in their proposal.

I learned this by studying Danny Margulies’ kickass blog, Freelance to Win – another fantastic resource for accelerating your journey to freelance success.

This is the job description of my first client, a real estate firm in Massachusetts.



Option 1) The Mini-Me Sample

Using the job description above, you could do a simple google search of “real estate blog posts” or check out a local RE/Max site and view their latest posts.

Look at samples of popular posts, see how they’re structured, and then create your own “mini-me” version of something similar, but not exact.

Let’s say you decide to model your sample on a post titled: “How To Stage Your Home For Sale On A Budget.”

(“Staging” is simply getting your home pretty/organized for sale)

Keeping it to ¾ of a page or less — write your own version, in your own words.

Deliver quality, but keep it simple (remember: you aren’t creating a masterpiece, just enough to demonstrate what you can do, so avoid spending more than 30 minutes).

Here’s a few ideas for headlines of short posts you could write for this topic:

  • 3 Easy Ways To Stage Your Home On A Shoestring Budget
  • How To Stage Your Home Without Spending $2K To Hire A Pro
  • Do-It-Yourself Home Staging In 3 Simple Steps

Attach these to the proposal message you send in. This will give the client a taste of your style, and what they can expect for your first job.

When you begin approaching the proposal process like this, you are effectively cutting to the front of the line.

Even if the other freelancer might beat you in a general copywriting duel — this approach gives you a fighting chance — because YOU went directly to the core of your prospect’s most pressing concern, and they will thank you for it.

Let’s be clear: I’m not trying to pump you full of airy promises of making easy money.

This takes work.

I didn’t get my first gig until I had submitted ~25 proposals. And the second client took more than 40 proposals.

There will be rejection. And sometimes it’ll sting.

But if you stick with it, the process will snowball on itself as you:

  • Improve your writing skills
  • Hone in on the proposal process (and get faster at it)
  • Gain a priceless, real-time look at what real clients need (and develop your skills/proposals around those needs)

You also build valuable experience talking to prospects about how you might help them.

Many of these prospect can (and will) turn into long-term clients if you aggressively try to solve their problems.

Again, these skills simply don’t come out of reading all the books, and lurking in the background — you’ve GOT to get boots on the ground and start working with clients.

So now you see… this process isn’t really “faking it” at all.

It’s delivering bite-sized proof of your skills, and indicating a sharp understanding of what they need. Clients will love you for this.

But what if you aren’t starting from square 1, and you have some pieces under your belt?

Option 2) Leverage Your Existing Assets & Skillz

If you’ve ever written ANYTHING creative for a past employer — a press release, a marketing brochure, even a quarterly report — you can use these as ammunition in your search process.

My first job out college was in real estate. Even though I was in a completely unrelated niche of this multi-trillion dollar industry, I made sure the client knew my background.

At the time, I was also working on launching a photography business. I’d written a cold email for brokers around the Denver area and was pitching them on my services.

(Note: the attached sales copy had not been proven. In fact, it hadn't even made me a single sale yet. Point is, you can easily create your own relevant samples to get clients.
(Note: the attached copy sample had not been proven. In fact, it hadn’t even made me a single sale yet. Point is, you can easily create your own relevant samples to get clients as long as you give them an honest taste for your work.)

Again, my sample was not an exact fit. But it was relevant enough to highlight: a) my writing; and b) a rough familiarity with the industry.

If you have experience or writing samples in a certain industry, keep your eyes peeled for jobs in your areas of knowledge (i.e. real estate, SEO) and exploit them when they arise.

John talks a lot about empathy here in this blog — because it’s something your copy should be dripping with.

It doesn’t matter WHO you are selling to, they want to feel understood, like you are speaking directly to them.

My proposal above is far from perfect, and honestly a bit more rigid and “professional” than I recommend, but it worked because I leveled with the client, communicating:

Hey, I know where you’re coming from, and here’s specific proof I can do the job.

This was back in April.

Since then, I’ve more than tripled my rates with most of my clients, which let me finance a move from Denver to San Diego, where I currently live and work, two blocks from the beach.

Point is, this is an epic training ground for new copywriters.

Before learning how to use Upwork, I was scared shitless, with no idea how to land clients.

I’d even started talking to local recruiters about finding a “real” job again…an idea that horrified me.

But with a novice-level understanding of copywriting, and the patience to lob in dozens of these custom-tailored proposals, I made it happen within a few weeks.

Nowadays, only about half of my business is still on Upwork.

The other half are referrals I’ve landed from long-term clients I found on the platform, who liked the work I’d done for them.

“But Austin, I’ve got a full time job and six pet goats to feed, I don’t think I have time for this.”

I get it.

While I was getting started, I was working on two other businesses, which only left about 3 hours a day to invest in the copywriting.

You might have even less time, which is still okay…

Because once you log in and check out the list of available jobs, you’ll see that Upwork is a deep, and constantly-renewing source of copywriting gigs.

And it’s growing. But don’t trust me, go create a profile, and check it out for yourself here.

Regarding your time concern, let me ask: “How serious ARE you about this?”

All it takes is a few weeks of experimenting for an hour or two after work. If you can’t invest the time, then this probably isn’t for you.

Worst case?

You end up with a portfolio of sample writing, and improved persuasive writing abilities (which you can use in ANY written communication where you want someone to take a specific action).

Best case?

You get your first client, use the momentum to continue taking new jobs…

And in a few months you could be earning enough to quit your job, or bank a new stream of revenue.

All without risking the expensive startup costs, capital investments, and other risks involved in building traditional businesses.

If you’re interested in becoming a copywriter, let the wise words of Bruce Lee guide your next step:

“If you spend too much time thinking about a thing, you’ll never get it done.”

Go get it done, and let me know how you go!

If you want to boost the conversions of your sales copy, then you’ll need to find your message-to-market match. Get the 5-step questionnaire to dial in your match with Austin’s M.E.M.E. Marketing Guideor click the link to learn more about Austin. 

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