LANDING YOUR FIRST GIG ON UPWORK

TOWOBOLA, Olamide
7 min readJul 22, 2020

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Landing your first gig on Upwork

Hey! I’m sure you enjoyed reading my last blog post — “Getting Started on Upwork — The Beginner’s Guide”. You can still read HERE.

Now, let’s roll into today’s topic;

You have signed up for a freelancer account. You have spent hours filling out your profile to perfection. You might even have spent countless days writing and submitting proposals with little or no conversion.

Relatable right?

Well, you’re not alone here. In fact, this is something a lot of new freelancers are struggling with when they first jump into the difficult world of Upwork and other freelancing platforms like Fiverr, Guru, and Freelance.com. Unfortunately, it’s an experience that eventually leads people to come to the wrong conclusions about freelance platforms as a whole.

However, I often find myself saying to my students, “Upwork is not the problem” but “your approach to Upwork is the problem”. It’s been just a few years freelancing, I made up my mind to stop asking “where are all the clients?” You know why? They’re busy hiring freelancers who don’t ask where all the clients are.

FLAWED CONTENT

The internet is filled with garbage advice on every imaginable topic, from marketing, designing, and, of course, freelancing. Many of the materials you’ve read about being a freelancer on Upwork is focused on traditional thought. Approaches that seem sensible, but in reality, they fall flat in the kind of online setting that Upwork harbors. Despite popular belief, success on Upwork (or any freelance platform) is not predetermined.

The reality is this:

  • You don’t need to have prior experience
  • You don’t need to have a portfolio
  • Qualifications are not required

Any “material” that says otherwise is only spewing inappropriate advice that has long passed its sell-by-date. It’s the kind of stuff that lingers on old forums and blogs like a fart in the elevator. Regardless of how dedicated you are, if you follow the wrong advice, you’ll just keep spinning your wheels until you burn out and join those who peddle the cliché “Upwork is hard”.

MY “SECRETS”

I put “secrets” in inverted commas because, despite the very few people who actually implement them, they’re not secret at all. Ready to blow your mind? These are the three main secrets that I’m going to discuss in this blog post, and yeah, I learned these secrets from a top freelancer, and it has helped greater:

  • Confidence
  • Technical Skill
  • People Skill

Before you face the palm and click away, bear with me for a moment. You already (hopefully) know that being confident is crucial to success. This isn’t a new thing. But, if there’s one thing I’ve come to understand, it’s that knowing all this stuff isn’t enough on its own. The goal is to get a grip on these secrets and consistently focus on your overall Upwork approach. Then (and only then) everything else is going to start clicking in order.

Okay, it’s time to get your wet-suit on because we’re about to do a deep dive.

CONFIDENCE

Being confident in laymen’s terms is simply establishing yourself as an expert on a given subject. In reality, some people don’t see themselves as “confident” in anything. The fact is, you’re hard-wired to think that way, and it’s a product of a cognitive bias. Clients are going to Upwork because they don’t know how to create a website. They don’t know how to write a convincing copy or landing page. They don’t know how to create an iOS app or design a product UI. Assuming you know more than they do, you are an authority in their eyes. All that remains to be done is to help them realize that fact.

HOW TO PROJECT CONFIDENCE ON UPWORK

Being confident or being knowledgeable about a given subject is not enough to land clients on Upwork. You need to learn how to grow your confidence and market your knowledge before you can really start capitalizing. So let’s look at a few specific tactics that you can use:

Offer Suggestions

When you read a job posting, take some time to make tailored suggestions based on the subject of the task in your proposal. Understanding job postings is a skill. For example: if the client is trying to increase the conversion rate for his landing page, check out the website and give the killer tip that can be used for quick-winning. Not only does this prove to the client that you know your onions well, but this value-first strategy will land you more gigs subsequently.

Understand the client’s needs

Oftentimes, I read proposals that are entirely focused on freelancers and their experience, skills, abilities, — Blah — Blah. The problem here is that you don’t become an expert by telling anyone that you are an expert. It’s perceptive, and the easiest way to influence such thinking is to put the client’s job in the spotlight. Whether it’s in your profile description or in your proposal, you should be involved in aiming to help the client get his job done professionally, rather than selling yourself. There’s a big difference between the two and believe me, the mind-set you carry will definitely influence how you draft your proposal. If you have to struggle to write a proposal for a job, then, it’s probably not worth sending. Most clients aren’t looking for world-class experts. They just want someone who cares about doing the job, and is willing to work hard to make that happen.

TECHNICAL SKILLS

Technical skills come down to whether or not the client believes you can do the job. Of course, you are inheriting a certain level of credibility when you effectively position yourself as an authority. But this isn’t always enough. Not only do you need to show your abilities, but you need to provide some sort of proof that you can get the results. This is where portfolios and high-level testimonials play a large part for many people, but they are not necessarily compulsory.

Attach Relevant Samples.

Yes… I told you that having a portfolio isn’t a necessary component to being a successful freelancer on Upwork. However, it is important not to throw the baby away with the bathwater. Samples are also extremely valuable when it comes to conveying credibility, and if you don’t have a portfolio to choose from, you can just build them on-the-fly. The biggest effect you can have on your proposal is not by submitting long or complicated write-ups, and it isn’t even about outstanding quality. Don’t tell clients what you can do for them. Show them what you can do for them.

Add 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.

All you have to realize is…

Nobody said your testimonials must appear exclusively on your Upwork profile, and neither did anyone says they should come from Upwork itself. In other words, you can source testimonials from past clients, colleagues, or even friends and relatives, and then you can simply paste them straight into your cover letter or upload as your portfolio.

PEOPLE SKILL

A lot of this stuff comes down to just being human, and, as simple as it may sound, you’d be astounded by how many proposals read like a letter to the President.

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

Always Address the Client by their Names

If there’s an easy way to make a good impression right from the start, it’s by addressing the client with their actual name. As a client on Upwork, even though I have specifically stated my name in the job description, I still find that more than half of freelancers that applied failed to include my name in their proposals (which places them promptly in the rejected archives) Can’t you see a name? I have some sly tricks to find the name of a client, but I’m just sharing them with my subscribers so you’ll have to read till the end to subscribe to my newsletters.

Profile Overview

See the little circle next to your name on Upwork? That’s right, your profile picture. That little beauty is one seriously overlooked piece of real estate, and using a cropped FB picture from your friend’s stag-party just isn’t going to cut it. Not this time. The biggest impact you can make with your profile picture is a smile. And not only a casual smile, but the biggest full-on ear-to-ear smile you can muster. A real smile is incredibly strong. It communicates ease and openness, transparency, and trustworthiness. It is probably the most immediate way to convey likability to your Upwork clients.

Conclusion

Understanding and applying these core secrets will not only make it possible for you to secure your first Upwork job, but they are the key to landing consistent work on the platform. And while I’ve just scratched the surface of the individual techniques, the lessons in this article alone will bring your head and shoulders above the competition.

Feeling confident, huh? It’s time to get back to Upwork and win your first job.

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I hope you found this blog post helpful, and you learned one or two things? Let me know in the comment section. Whilst accessing the blog post is free, SHARING with others is MANDATORY. I’d love to reach a larger audience that would glean one or two and advance their freelance journey. My job is to see you grow and become better.

I’ll be sharing more Upwork and freelance tips — from step-by-step proposal writing guides to finding a niche, how to optimize your profile, and more!

Do you have any questions on freelancing? I’m happy to help.

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TOWOBOLA, Olamide

Hi there. My name is Olamide Towobola, a freelance coach and copywriter. I share helpful tips and resources on freelancing, digital skills and remote work.