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When I decided to become a freelance copywriter nearly 3 years ago, I was a little nervous.

And when I say nervous, I mean TERRIFIED.

Until then, I had only written as a hobby, with no pressure, feedback, or deadlines.

The stakes were low. There was no risk that anybody would read my stuff and send me a nasty email saying, “You expect me to pay for this %#&!-ing piece of crud?!?!?”

Come to think of it, there was no risk that anybody would read my stuff, PERIOD.

My writing (and ego) was blissfully protected from the cold, harsh realities of the business world.

But getting paid to write is a whole different ballgame. The mere thought of being hired by a company expecting MY writing to boost THEIR profits made me queasy.

It’s a big responsibility.

I’m just a regular guy, typing (somewhat slowly) on my laptop, sipping Starbucks and wearing an old pair of crocs. But a marketing expert?


Diving headfirst into freelancing felt like going from casual swimmer to professional lifeguard.

I needed baby steps. Small projects with low expectations. Clients with modest budgets, who were okay with not getting Dan Kennedy or Joe Sugarman caliber copy.

The Conventional (Flawed) Approach

I scoured forums and blogs, looking for the fastest way to break into freelancing. Some suggested inventing make-believe projects out of thin air, and writing made-up copy for “pretend” clients. Then after a few months, I could put it all together and call it my portfolio.

Others advised creating a blog that no one would ever be likely to read, and writing dozens of blogposts, then showing it to prospects in the hope that a blog with no readers would somehow impress them.

But those ideas didn’t make sense to me (and I suspect others), for a few reasons:

  • It’s hard to stay motivated when you know it’s just a test run
  • Without genuine deadlines, I tend to work painstakingly slowly
  • Most importantly: I was not looking to create a random portfolio. I wanted to become an expert writer, and the “fake” approach would not produce those results. The only way to elevate your game is by getting cold, honest feedback from a paying client

Besides, it’s pretty demoralizing to write dozens of blogposts for 3 or 6 months, and end up with a grand total readers.

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With my limited professional experience (and by that, I mean zero), I needed to get assigned real projects and build a genuine portfolio fast. I also needed a low-pressure environment where I could make mistakes and not suffer long-term repercussions.

I realized that Upwork (formerly Elance) was the perfect place to launch my career. (It doesn’t matter if you plan to use Upwork as your long-term source of clients or not, it’s a great place to gain traction at the early stages either way.)

Here are 8 reasons why:

1. Many Upwork clients are willing to give Newbies a chance.

When creating a job posting, clients have 3 choices: Entry, Intermediate, and Expert. When they pick “entry level”, they’re essentially saying “I have a low budget. I know I’m not getting a stellar freelancer, and I’m okay with that.”

This keeps pressure and expectations relatively low. (Tip: Even if you do entry projects, put in the time and effort to create something awesome. For clients, the only thing better than getting a quality product, is getting a quality product when you expected mediocre. It’s a slam-dunk way to get clients to leave you a great review.)

2. You’ll build an impressive online resume.

By getting hired and completing projects, you’ll develop your Upwork profile, and have a recorded work history and reviews under your belt, all verifiable on a well-known third-party website. That gives you serious credibility early in your career.

Even if you end up working elsewhere long term, you’ll be way ahead of the game by showing prospects you’re an established professional with a record of similar projects. Plus, you may not need to ask clients for testimonials, which can be awkward and uncomfortable, because Upwork asks them for you.

3. Improve your skills dramatically faster.

When you work for real clients, (even ones with “entry level” budgets) you will feel highly motivated to deliver something great and perform at peak level. It helps you get a good review, feel a sense of accomplishment, and most importantly, you’ll genuinely want to boost your clients’ business, which is the reason they hired you. Tackling projects is the “fast-track” way to gain real expertise in any niche.

4. Get paid to learn.

Either way you’re planning to spend time learning, perfecting your skills, and developing a portfolio. Why not get paid to do it?

5. Live links to your samples.

When you create a piece of copy or graphic design for someone’s website or landing page, it has a good chance of being published live on the web.

Which means that instead of sending a “pretend” sample in boring PDF format, you can send clients a real live link, which is way more impressive, and shows prospects your work as a final product, leaving nothing to the imagination. Some clients even ask you to send live samples.

6. It’s fun.

There’s nothing like the thrill of doing a paid project, and the adrenaline rush of meeting a deadline. You get to send your deliverable to the client, sit back as they review it, and (hopefully) get a response telling you how much they like your work. It can be an awesome experience.

7. Deadlines are your best friend.

Unless you’re super disciplined, you will probably procrastinate a little with your own practice writing. It’s human nature. By accepting real jobs for real people who set real deadlines, you’re guaranteed to move faster than virtually any other option.

8. It’s free.

You’ve got zero to lose. Just set up an account, and bid for jobs. Worst case scenario, if it doesn’t work out, you can always close your account. What are you afraid of?

Dry-runs don’t do the trick

Nothing replaces real-world experience. You can land a plane in the Hudson a thousand times in a flight simulator, you still won’t be prepared to sit in the cockpit, a flock of geese just having destroyed all four engines.

There’s a reason many career fields have internship requirements. Walking a tightrope with a net underneath simply won’t prepare you to walk across Niagara Falls.

That’s why Upwork is ideal for your freelance internship.

If you’re planning to spend time studying your field before you dive in, I recommend taking on real jobs.

You will learn everything you need, faster than you ever imagined. You’ll develop a “live” portfolio, pick up valuable real world experience, get great reviews, and...oh yeah, you’ll get paid to do it.

As a Newbie Freelancer, I don’t care how many online courses you take, you won’t be prepared to take clients until you dive in and swim with the sharks. (Don’t worry, most clients are gentle sharks like Robert Herjavec, not Kevin O’Leary.) Sooner or later, you’ve got to take the plunge. No matter how much time you spend in the shallow part of the ocean, it won’t get less scary.

Why not hold your breath and get it over with now?

Josh Margulies is a Freelance Copywriter. His “no-fluff” blog and podcast, Fast Track Freelancer, teaches newbies and veterans how to achieve continued success. To get Josh’s free emails with his personal strategies to attract more clients and write better job proposals, click here.