8 Ways the Most In-Demand Freelancers Get High Paying Assignments

Side hustles have become decidedly mainstream: Freelance marketplace website Upwork estimates freelancers now compose around 38 percent of the US workforce. That means 64 million Americans are out there competing for the same assignments you are.

The increasingly saturated freelancer market means that brands have a wealth of options when they need quality work done—with the key word here being quality. In 2025, AI still hasn’t reached the same level of excellence as real people (OpenAI’s 14-million-dollar Super Bowl commercial that was developed entirely by humans).

At Masthead, we proudly hire freelancers for a broad range of creative and strategic work, from creating data-packed customer stories for big tech brands to developing highly detailed voice-tone strategies for nonprofit organizations. When we find talent, we truly value those people and turn to them first when new opportunities arise—we also pay them really well.

So how can you become a freelancer who’s always in demand—and one that can command a serious six-figure salary? Read on for best practices based on our own experience with freelancers, plus tips from Masthead colleagues and freelancers we know and trust.

1. Meet Your Deadlines

It may seem obvious, but there are lots of freelancers who regularly breeze past deadlines — sometimes without any communication. Set yourself up for client success by always meeting yours.

“If something comes up last minute where a deadline absolutely can’t be met (such as a family crisis, or your computer has fallen into the ocean…basically the only legitimate excuses I can think of that you wouldn’t know about in advance), communicate like crazy,” says Caila Ball-Dionne, Masthead’s Vice President of Editorial Operations. 

“The worst feeling as an employer working with clients is missing your deadline because you’re waiting on a deliverable with no idea when it will arrive.”

Bonus points if you’re a freelancer who delivers your work before the deadline, especially with the first assignment. Your editor or project manager will love having an extra day or two to work, and they’ll know they can rely on you in the future.

2. Make Yourself (Very) Available

Yes, part of the benefit of freelancing is being able to set your own schedule and work from anywhere in the world — but many of your clients work traditional 9-to-5 hours in certain time zones. If you want to be called upon — a lot — make sure you have strong WiFi and phone connections and can accept meeting invites during client hours.

If you’re going to be unavailable at any point (whether it’s for a weeklong vacation or a day of doctor’s appointments), give your regular clients a heads-up—well in advance. 

“Get it on their calendar early so they can plan around it,” Ball-Dionne says. “On that note, if you have assignments going on while you are out, present the solution to them of how it will be handled (which should never be, ‘We’ll push the client deadline’).”

Masthead freelance writer Diana Kelly Levey lets her steady clients know weeks in advance about the dates she’ll be away — even if she isn’t working on something for them at that time. “It gives me an excuse to check in with clients and let them know I have time before I leave to help out with work,” Levey says. “It’s a great way to get more assignments!”

3. Be Nimble

In an ideal world, all assignments would be very explicitly outlined right from the start and never change from there. But that’s not always realistic: Sometimes, clients have to make shifts in strategy or they simply change their minds.

In those cases, “be flexible when you can,” Ball-Dionne says. “This does not mean let yourself get trampled on, but if there are slight changes to an assignment that, in the grand scheme of things, are not going to create an excessive amount of work, roll with them.”

Adding an extra line or two to clarify a point in an article? Fair. Conducting more interviews or adding paragraphs? Worth a discussion with the client or your project manager to determine if you’ll need to expand the scope (and your compensation).

4. Be Proactive And Positive

Take small, proactive measures in your professional relationships. Ask your project manager or editor how they prefer to share information (such as via Slack, Basecamp, email, or on calls) and follow their style of communication. 

This small step will help you stay in a manager’s good graces. 

When challenges inevitably arise, don’t wait to be told what to do or groan when you’re asked to address them. At Masthead, we value freelancers with positive attitudes who always come to the conversation with potential solutions.

5. Treat Yourself As a Small Business

You may be one person, but you’re running a business — so it’s important to act that way. Build a professional-looking website with an updated portfolio and bio page.

Stay on top of unpaid invoices, use contracts, deposit payments in a business checking account, and pay taxes on time.

“Treating yourself as a business means keeping track of your invoices (not asking a client if you’ve invoiced them yet, in turn putting the work on them), and being as buttoned up as a small business owner has to be to retain clients,” says Ball-Dionne.

Always turn in clean work that was done according to the client’s style guide preferences. Saving them time by following directions is a simple thing, but it gets noticed by clients.

As a small business, you should also ensure that you have a clean, easy-to-navigate website live on the web—one that lists your services, examples of your work, and all the ways you can be contacted. While a LinkedIn profile is also extremely valuable (see more on this below), a website provides a great opportunity for brands and agencies to view your work.

6. Sell Yourself

Tooting one’s own horn can be tough, especially for people in creative fields or those who aren’t very outspoken. But to gain and maintain business, you have to turn in good work and make sure people know about what you’re working on.

Keep your LinkedIn profile headline, summary, and About sections updated so hiring teams and managers can easily find you. Share a recent testimonial from a client or a freelance project you’re proud of (you’ll generally need to be proactive and ask for this from a previous employer or hiring manager).

Even if you’re not looking for a full-time job, these kinds of updates are hugely helpful to agencies and brands to see what you’re up to and what you specialize in. 

Think beyond LinkedIn as well. Remind clients of the various talents you bring to the table and any new skills you picked up.

Remember to always be respectful of client confidentiality. Confirm with the manager whether you can mention their brand on your public website or social media pages if you’re promoting the work you did for them.

7.  Know When to Say “No”

It’s hard to turn down business, and if you’re available, saying yes to as many client requests as possible is a great way to show them you’re dedicated and up for the job. 

But, Ball-Dionne advises, “Say no when you are overloaded. Don’t let your client work suffer because you’ve taken on too much.

It’s also good when you are overloaded to let a client know your plate is full, but you will be more available on [a specific] date, if you have that information.”

There’s a good chance that if they want to work with you, they’ll wait.

You might be tempted to take on lower-paying freelance work to get exposure to a company you’re excited to work with or partner with a new agency. The temptation is real during slow times! Try to evaluate whether it’ll require too much time and energy that you should be using for higher-paying freelance work.

8. Ask for Referrals

Once you have a good working relationship with a manager (after a few assignments), ask if they would refer you to a different department or write you a LinkedIn referral. 

This could be as simple as: 

Thank you, [NAME], for the recent assignments. I really enjoy working with [COMPANY NAME]. Do you know of other departments or colleagues that you think could benefit from my services?  If so, I’d appreciate it if you’d keep my name in mind to pass along to them. 

If the client gives you a testimonial on a social platform like LinkedIn, ask them if you can use it on your website or other public platforms.

Referral work is one of the best ways successful freelancers get more freelance work without spending a lot of time and effort looking for it.

Ready to find great clients to work with? Apply to Masthead’s freelancer database.