How To Get Your First Job On Upwork Using These 3 “Secret” Ingredients

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You’ve signed up for a freelancer account.

You’ve spent hours filling out your profile to perfection.

And you’ve wasted countless days pumping out proposal after proposal without so much as a rejection email to show for it.

Sound familiar?

Well, you’re not alone. In fact, this is something a LOT of new freelancers struggle with when they first jump into the difficult world of Upwork.

And, sadly, it’s an experience that ultimately leads people to come to false conclusions about the platform as a whole.

But, as I often find myself saying these days, the problem isn’t Upwork. The problem is your approach to Upwork.

Flawed Advice

I want to start off by saying that it’s not your fault.

The internet is riddled with garbage advice on every topic imaginable, from relationships, to marketing, and, of course, freelancing.

Most of the stuff you read about Upwork is based on traditional thinking. Approaches that work great in the real world, but in reality, they fall flat in the kind of online environment that Upwork harbors.

Despite popular belief, success on Upwork (or any freelance platform, for that matter) isn’t predetermined.

The truth is:

  • You don't need previous experience
  • You don't need a portfolio
  • And you don't to be qualified

Any “resource” that says otherwise is just spewing flawed advice that’s long passed it’s sell-by-date. The kind of stuff that lingers on old forums and blogs like a fart in an elevator.

It doesn’t matter how dedicated you are, if you’re following the wrong advice, you’ll just keep spinning your wheels until, eventually, you burn the f**k out.

Why Should You Listen To Me?

I just told you that most of the “Upwork advice” out there is total crap, so what makes mine any different?

It’s a good question, and one I hope you at least pondered in the back of your mind.

All I can say is, unlike most of what you read nowadays, I’m actually applying what I teach in my own business. (In fact, you can head over to my Upwork profile right now and confirm for yourself.)

And what I’m about to share with you is the exact strategy I used from the beginning, allowing me to secure copywriting work at $35/hr, and closer to $100 only months later.

And I did it...

  • Without ANY copywriting experience
  • Without a SINGLE portfolio piece
  • With ZERO relevant qualifications

But more than that, I did it regardless of having virtually no history on Upwork, and with more established copywriters were charging less than I was.

How I Pulled It Off...

I’d like to tell you that I’m gifted. I’d like to tell you that I’m incredibly intelligent and that I somehow managed to “hack” my way to the top.

But the truth is, I was just lucky.

Before I started freelancing on Upwork, I was already very familiar with the platform because I’d been using it to hire freelancers for almost 5 years.

Being on the other side of the fence for so long gave me a distinct , unfair advantage when I eventually did switch sides.

And because of that, I was quickly able to reverse-engineer the core ingredients. The same ingredients I’m about to share with you.

The 3 “Secret” Ingredients

I put “secret’ in inverted commas because, despite very few people actually implementing these, they’re not really secret at all.

Ready to have your mind blown? These are the 3 core ingredients we’ll be tackling in this post:

  1. Authority
  2. Credibility
  3. Likability

Before you face-palm and click away, bare with me for a moment.

You already (hopefully) know that being authoritative, credible and likable are crucial ingredients for success. That’s not a new concept by any means.

But, if there’s one thing I’ve come to realize, it’s that just knowing this stuff isn’t enough by itself.

The key is getting a handle on these ingredients, and actively working them into your overall approach on Upwork. Then (and only then) will everything else start clicking into place.

That includes:

  • Your profile overview
  • Your proposals
  • Your work samples
  • Your communication

Alright, it’s time to get your wetsuit on because we’re about to do a deep-dive.

Ingredient #1: Authority

Being an authority, in laymen's terms, is simply establishing yourself as an expert on a given topic.

And that’s the word people get hung up on. In fact, most people don’t see themselves as being an “expert” on anything.

The truth is, you’re hardwired to think that way, and it originates from a cognitive bias called the Dunning-Kruger Effect.

Hence, the corollary to the Dunning–Kruger effect indicates that persons of high ability tend to underestimate their relative competence, and erroneously presume that tasks that are easy for them to perform also are easy for other people to perform. - Wikipedia

To put it plainly, “authority” is subjective.

Clients go to Upwork because they don’t know how to build a website. They don’t know how to write compelling copy. They don’t know how to build an iOS application...

Assuming you know more than they do, in their eyes, you are an authority. All that’s left to do is help them realize that fact. (And again, it is a fact.)

How To Project Authority On Upwork

Being an authority -- or being knowledgeable on a given subject -- is not enough to land clients on Upwork.

You need to know how to project your authority and market your expertise before you can really start to capitalize.

So let’s look at a few specific tactics you can use:

#1: Offer Suggestions To Demonstrate Value

Whenever you get the opportunity, take some time to make tailored suggestions based on the subject matter of the task.

For example: if a client is looking to improve the conversion-rate for a landing page, check out the page and offer a killer tip that can be implemented for a quick-win.

Not only will this prove to the client that you know your shizzle, but this value-first approach will land you more gigs than you’ve had hot dinners.

#2: Dig Deep Into The Client’s Needs/Pain Points

All too often do I read proposals that are entirely focused on the freelancer and their experience, qualifications, ability,… blah blah.

The problem here is that you don’t become an authority by telling someone you’re an authority. It’s perceptive, and the best way to influence that perception is to put the spotlight on the client.

Whether it’s in your profile overview or in your cover letter, you should always be aiming to help the client, as opposed to selling yourself. (I cover this more in my cover letter analysis post.)

There’s a huge difference between the two and trust me, the mindset you go into this with will almost certainly be carried over in your writing.

#3: Communicate With Power

Alright, so this isn’t a “tactic” per se, but your ability to communicate with power is possibly the single most important factor when it comes to projecting authority -- so it has to be said.

For them most part, communicating in the right way stems from believing not only in your ability to deliver results, but also in the true value of your services.

(Wait, you do believe in the value you’re offering, right? Good.)

Not only that, but once you stop clamouring for clients and and start putting yourself in an “overbooked mindset”, you’ll naturally remove any semblance of desperation from your communication.

Ingredient #2: Credibility

Being “credible” ultimately comes to down to whether or not the client believes you can do the job.

Of course, you do inherit a certain level of credibility when you effectively position yourself as an authority…

...but that’s not always enough.

Not only do you need to demonstrate your expertise, but you also need to provide some form of evidence that YOU can get the results.

This is where, for many people, huge portfolios and high-level qualifications play a big part, but they’re not necessary. (In fact, they are among the least effective ways to establish credibility in my opinion.)

How To Establish Credibility On Upwork

There are a few ways I like to do this on Upwork, and each one is tailored to a specific, but universal goal.

Paint a picture of the end result.

I realize that’s sometimes easier said than done, but let me give you a few specific tactics you can use to achieve that.

#1: Give Them The Blueprint

This is something I’ve yet to see any other freelancers using, and it’s a technique I dubbed, “The Mind Map Method”.

Basically, it works by creating a mind map (or any other visual medium) that outlines your process from start to finish. I won’t go into it here because I wrote an entire post on it, so I highly recommend you check out.

There’s a fair bit of setup time to it, but once you’ve created your mind map, it’s something that really sets you apart from everyone else. Besides, it can be used repeatedly, so it’s absolutely worth the upfront investment.

#2: Attach A Highly-Relevant Sample Piece

Yes… I told you that having a portfolio isn’t a necessary component to being successful on Upwork. But let’s not throw the baby out with the bathwater.

Samples are still incredibly important when it comes to conveying credibility, and if you don’t have a portfolio to choose from, you can simply create them on-the-fly.

The biggest impact you can make with your proposal isn’t by submitting something super long or complex, and it isn’t even necessarily about outstanding quality…

...It’s about relevance.

Fortunately, starting from scratch and creating proposals on a need-to-have basis puts you at a massive advantage, because you’ll always have a scarily relevant sample to attach alongside your cover letter.

#3: Cough Up Some Stellar Testimonials

Nothing screams credibility like someone else vouching for your services, especially when the results speak for themselves.

If you’re just starting out on Upwork, you probably don’t have any Upwork feedback to leverage for this, and that’s okay. While this does seem like a bit of a catch-22, there’s a pretty simple workaround.

All you have to realize is...

Nobody said your testimonials must appear exclusively on your Upwork profile, and neither did anyone say they should come from Upwork itself.

In other words, you can source testimonials from from past clients, colleagues, or even friends and relatives, and then you can simply paste them straight into your cover letter.

Ingredient #3: Likability

“Likability” is often attributed to in-person scenarios, but I can tell you now, the same principles apply online, and Upwork is no exception.

The funny thing is, most freelancers tend to overlook this ingredient, and it’s one that will almost always give you the edge over your competitors.

Fortunately, only a slight shift is needed to take full advantage of this, and you’ll slap yourself once you realize just how powerful it is.

How To Be Insanely Likable On Upwork

A lot of this stuff comes down to just being human, and, as obvious as that may sound, you’d be amazed at just how many proposals read like a letter to the President.

Again, let’s look at a few specific tactics you can use:

#1: Address Each Client By Name (Seriously)

If there’s one stupidly easy way to set a good impression right from the start, it’s by addressing the client by their actual name.

Yet, even when I’ve clearly listed my name in the job description, I find more than half of applicants still fail to start their cover letter with it. (Which promptly lands them in the rejected archives.)

Can’t see a name? I’ve got some sneaky tricks for finding any client’s name, but I only share them with subscribers so you’ll have to gimme your email if you want in. 😉

#2: Inject Complements Where Appropriate

I struggled with this myself at first because I really hate forced compliments. (They’re so pronounced and full of intent.)

But I quickly figured out that even a subtle compliment slipped into your cover letter can go a long way, and if you know where to look, it’s really not hard to find a genuine reason to make one.

It could be as simple as...

  • Complementing the design of the client’s website
  • Acknowledging a need for the client’s product
  • Showing an interest in the client’s business or market
  • Thanking the client for a detailed job description
  • And literally dozens more...

Such a small thing, but it really does work wonders when it’s said in the right way and with conviction.

#3: Show Dem Pearly Whites

See the little circle that appears next to your name on Upwork? That’s right, your profile photo.

That little beaut is one seriously overlooked piece of real-estate, and using a cropped FB picture from your friends stag-party just isn’t going to cut it. Not this time.

The biggest impact you can make with your profile photo is to smile. And not just a casual smirk, but the biggest full on ear-to-ear smile you can muster.

A genuine smile is incredibly powerful. It communicates ease and openness, approachability and trustworthiness. It is perhaps the single most immediate way to express likability. - The 11 Laws Of Likability

Wrapping It Up

Understanding and applying these core ingredients will not only allow you secure your first job on Upwork, but they are the key to landing consistent work on the platform.

And while I’ve only scratched the surface on the individual tactics, the lessons in this article alone will put you head and shoulders above the competition.

Feeling confident? It’s time to get yourself back on Upwork and win yourself that first job.

Good luck!

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