How to Get More Freelance Gigs: Tap Into a $2.5 Billion Market

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Chris Misterek

Few words will get as polarizing a response among freelancers and side hustlers as Upwork.

Depending on who you ask, it’s either a fantastic platform to connect with well-paying gigs and quality clients … or it’s a hopeless, desperate race to the bottom, overly-competitive bloodbath with no chance of success.

Like a lot of things, the truth is probably somewhere in the middle, and a lot of your outcome will depend on your strategy and how well you show up.

Upwork is the world’s largest freelance marketplace. The platform booked $2.5 billion worth of work last year, so there’s no shortage of cash flowing — if you know how to get it flowing toward you.

To help is do that, I invited 2020’s most popular guest, Chris Misterek, back to the show.

Chris is a web design pro who’s booked over $80k worth of work through Upwork.

(We’re going to focus on Upwork but these same rules apply for other freelance platforms as well, like Fiverr or Thumbtack — so get ready to set yourself up for success.)

Tune in to The Side Hustle Show interview to learn:

  • how you can set up your Upwork profile for success
  • why Chris says niching down will help you secure more jobs
  • how to pitch clients the right way to increase your chance of landing your ideal jobs

Set Your Profile for Success

“When you are setting yourself up on the platform, you’ve got to think through the eyes of your potential client,” Chris explained.

One of the most common mistakes Chris sees freelancers making when creating a profile on Upwork is focusing on themselves. Doing things like talking about how awesome they are, providing a long list of skills, extensive experience, and so on.

If you want to set up your profile for success, Chris said you should start by looking for the connection between what you have to offer and what a client is looking for.

He went a step further and said that if you get to the point where you’re having an actual conversation with a client, you should be using the pronouns, “you”, or “your”, at least every seven or eight words.

If not, you’re not talking about the client enough and you’re probably talking about yourself too much and trying to position yourself as the “hero”.

You have to think of the client as the hero. Your role is to guide them to become more successful, Chirs explained.

Include Rich Elements in Your Profile

Chris said it’s worth spending the time to fill out your entire profile to the max as you never know what is going to be the deciding factor in someone hiring you.

This has worked out well for him, and a couple of examples he shared was;

  • Being hired by someone from Texas who picked up on the fact that Chris went to college in Dallas and liked that about him.
  • Being hired by a course builder who loved Chris’ short profile video he made.

Upwork gives you the option to record a video for your profile. Chris said that doing so is important when creating your profile – no matter how shy or introverted you are.

You don’t have to have any video production or editing skills either. Chris recorded his video on his MacBook camera, edited it in iMovie, added some music, and that was the first time he’d ever edited a video.

Niche Down

“The more that you can niche down with who you are, what you do with what tools you use, and who you serve, actually opens you up for most success,” Chris told me.

Chris explained that a lot of freelancers are afraid to niche down and be very specific about what they’re offering as they think it will lose them a lot of potential clients.

But trying to cast a wide net has the opposite effect and makes it less likely you’ll get hired, Chris explained.

The more specific you are about what you can do and the types of clients you’re looking for, the more chances you’ll have of attracting those clients.

For example, instead of saying you’re a web developer or even a web developer with JavaScript experience. Chris said you could say you’re a mobile and web application developer who specializes in React and serves the health and fitness industry.

If you’re looking to work with clients in the fitness industry, you’re going to stand out as a freelancer with the exact skills and experience they’re looking for with that in your bio.

You can also add industry-specific accolades that will catch the eye of prospective clients. Chris knows a graphic designer who has earned more than $500,000 in the last four years on Upwork by doing this.

She puts “featured in Business Insider” in her title. So, it’s clear that her work has been used in one of the largest online publications and adds some social proof to the quality of her work.

Use Social Proof and Testimonials

Obviously, when you’re new to Upwork it’s hard to display social proof for your work and you won’t have many reviews on your account.

Upwork doesn’t want freelancers linking out to their own websites and examples of their work elsewhere on the web, as this takes people off their platform.

They do, however, make it possible for you to email previous clients you’ve worked with outside of the platform and send them a form to fill out.

This form asks for feedback on a project you’ve worked on, or it can just ask for a character reference. This feedback then shows up on your Upwork job profile and is a great way to get some social proof as a new account.

Be Specific With Your Skills

Another tip Chris shared, and this is something that also worked out really well for him when he got started, is to be specific with your skills.

Upwork allows you to list 10 or so skills in your profile. When Chris started out he only listed four skills because he said he really only had four relevant skills at the time.

This worked out to his advantage as he listed OptimizePress, a WordPress plugin as one of his skills. He ended up getting a lot of work from clients looking for someone experienced in using that exact plugin.

We’ve seen this before on the Side Hustle Show: guests specializing in one specific software and positioning themselves as the go-to expert.

Like Brad Rice, who booked more than $225,000 worth of Salesforce consulting work, and Paul Minors who built his virtual software consulting business around Asana.

The beauty of doing this is that new software is coming out all of the time, so you can position yourself as an early adopter of a new software product.

Bid on the Right Projects

“You can waste a lot of your time bidding on projects that you have no business bidding on,” Chris told me.

The last thing you want to do is spend a lot of time unsuccessfully bidding for jobs on Upwork. It’s time-consuming and demotivating.

Upwork provides you with some filters to help you narrow down the jobs you want to bid on, and Chris said you should use this to your advantage and find the jobs you’re more likely to be successful for.

Some of the filters Chris recommends using are:

  • Number of proposals – The more proposals a job has, the harder it is getting in front of the client. Chris filters down to jobs with 5 or fewer proposals so there is less competition.
  • Location – A lot of clients in the US only want to work with freelancers based in the US. You can filter jobs down to reflect only these (or whatever country you’re in).
  • Experience level – Upwork splits experience into three levels: entry, intermediate, and expert. You can filter jobs to match your current experience level, but your level of expertise largely comes down to where you view yourself in the market.
  • Hourly rate or fixed price – Most people have a preference on how they want to be paid. On Upwork, you can look for jobs paying either an hourly rate or a fixed price, and of course, look for jobs in your desired pay range.
  • Dollars spent – You can filter on the amount of money a client has spent on Upwork before. You may be more comfortable working with a client that’s more familiar with Upwork, or vice versa.

Chris said that all of these filters are great for helping you narrow down the types of jobs you want to – or should – be bidding on. But ultimately there is no one-size-fits-all, you’re going to have to find out what works best for you with some trial and error.

Set Up Notifications for Jobs

To further reduce the chance of missing out on jobs, once you’ve set up your filters you can save those filters as a kind of quick access to the main job feed.

Upwork then gives you an RSS feed of jobs matching your criteria. Chris takes that RSS feed and runs it through a newsreader app called News Explorer. This app has a one-off fee of $4.99 and sends push notifications when jobs matching your criteria are in the feed.

Chris has all of his job filters saved and the RSS feed set up to run through the app and he gets a notification on his phone when a new job gets listed matching his criteria.

A word of warning; Chris said the notifications are not always instantaneous. If you’re actively looking for a job you should refresh the job postings on Upwork more often so as not to miss out.

Another tool Chris knows some people use but he’s not used himself is called LeapFrog Leads. For $20 this service will send you notifications when jobs matching your criteria are posted on Upwork.

How to Pitch a Client for a Job

Finding jobs you want is one thing, pitching a client in the right way is going to be what gets you the job.

That first impression you make can make or break your pitch, so it’s important you have an effective outreach strategy.

Chris said the key is to make your pitch as client-specific as possible. Every client has their own unique personality, and Chris looks closely at the personality in the job description.

For example, if he can see that they’re very formal and all business, he’s going to get straight to talking business.

On the other hand, if they’re using “bubbly words” and coming across as very relatable, Chris said he’s going to talk about their business and try to create a relationship before getting down to business.

When it comes to writing the pitch, Chris said you should start out with some kind of value proposition. Followed by identifying some deeper motivations that the client may have as a way of demonstrating that you really understand what they’re trying to accomplish.

An example he gave was that no one buys a drill because they want a drill. People buy a drill because they want to put a hole in a wall or do some other DIY work.

What you could do is say that you don’t just want to put a hole in a wall for the client, you want to help them hang a picture of their family that will bring them joy.

That’s likely to provoke a much more emotional motivation than simply saying you can help put a hole in a wall.

When to Talk Money

Another mistake a lot of freelancers make is quoting a price or agreeing to a fixed rate before fully understanding the size of the job.

Chris saves talking about budgets and pricing until he’s actually having a conversation with the client. He’ll put a ballpark figure in his covering letter if it’s been requested, otherwise, he leaves it out until he can speak with the client.

Any Surprises/Mistakes Along the Way?

“I have made more mistakes as a freelancer, specifically on Upwork than I even care to talk about,” Chris told me.

One mistake that stands out was the second or third job that Chris got on Upwork. He said “yes” far too quickly to take the job without fully understanding the project.

It wasn’t long before Chris got shut out of the client’s website and the client was asking for a full refund.

The moral of the story here is that no matter how eager you are to secure a job, you need to be slow to start a contract.

Once a contract is started, it’s going to end with you getting feedback which will affect your job success score, Chris explained.

Coming back from negative feedback can be really hard, so be careful about what jobs you say “yes” to.

What’s Next?

Chris has a free training at the end of August called Three Simple Steps to Land High Paying Clients on Upwork.

In this course, he talks more about some of the things he’s discussed in this episode. That free training leads onto a paid course he created that helps freelancers become top-rated and highly paid freelancers on Upwork.

You can find out more about his free and paid courses by visiting (I asked and he said it would be relevant for freelancers in other niches as well, not just web design.)

Chris’ #1 Tip for Side Hustle Nation

“Figure out how to create systems and workflows that make it easier to scale.”

Links and Resources from this Episode


  • Skillshare – Get a free trial of Skillshare Premium Membership, with unlimited access to 30,000+ on-demand classes!

skillshare 2021

  • Self-Publishing School – Register for the free on-demand training on how to go from blank page to published author and receive a free copy of the bestselling book, Published.

self-publishing school

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

5 thoughts on “How to Get More Freelance Gigs: Tap Into a $2.5 Billion Market”

  1. Apparently you have to make a complete profile before you can see what work is even available on A quick look has turned into a project in itself.

  2. I make about $60k a year on Upwork working about 25 hours a week as a copywriter/content creator. It takes finessing and time to get it going, but it does work. I need a platform that regularly pays directly into my bank account, that’s flexible, and where I can work whenever I want around my kids’ schedules. Their reports and tools also make my accounting easier. I know there’s a fee on your projects, but meh… just bake it into your rate. At this point clients find me and ask me to apply to their jobs – I rarely bid on projects anymore. I also convert about 80% of the proposals I do end up sending.

  3. When the student is ready, the teacher appears. It just happens “that” teacher is usually Nick Loper and his fabulous posse of guest authorities. I’m building my freelance book of business (again) after another decade in Corporate America (again). This info is a huge help, thank you.


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