Let that sink for a second. 

At 43% of the US workforce in 2020, nearly half of US citizens are full or partial freelancers in one way or another. 

With massive economic changes as a result of COVID-19, even more people will be pushing into the freelance workforce. That means the question of how to perfect the freelance hustle looms even larger as more households depend on freelance income to thrive.

Whether you’re an experienced freelancer or new to the sector, there’s always an opportunity to up your game. Here we tackle resources and strategies freelancers can use to be successful in 2020.

How to survive working freelance in 2020

As with most things, there’s no magic formula.

Success as a freelancer in 2020 demands the right mix of human and technical skills. Even so, too many freelancers fear specialization. 

Naturally, they worry it will narrow the number of clients with whom they work. But wouldn’t it be great to have just a few, high-paying clients that you’re sure you can manage?

When freelancers specialize, they are claiming space to operate credibly within a market. Freelancers who specialize signal to potential clients that they’ve got the right expertise and aren’t spreading themselves too thinly or promising things they can’t deliver.

Your specialization should, of course, be tied to your experience, personality, and overall training within a specific domain. Any work samples you share with potential clients should demonstrate how you’ve shown results within your chosen specialization in your work with past clients.

The other great part of specializing as a freelance is that it helps you choose your clients more effectively.

With so many freelancers out there and countless job boards for gigs, showing up to such a broad market can be overwhelming. Digging into a focused (but hopefully not too narrow) niche can help you target those right-fit customers from the start.

Lastly, remember that you can still be a generalist in terms of hard skills while still specializing in certain sectors. In fact, that’s a good goal to shoot for—having skills that can largely span different industries alongside deep knowledge of a few domains. 

Even with freelancers scattered across a wide array of industries, there are still a few common threads that add up to a healthy freelance practice.

Know the market

Understanding the market you’re working in goes hand-in-hand with specializing.

Whether you cut your teeth at an agency or are self-trained and have always been a freelancer, clients will be looking for signs that you know their customers and landscape.

One good way to demonstrate this by sharing your knowledge about that market. Whether it’s a blog post on your own website or a short case study about a successful engagement with a client in the same industry, there are lots of ways to demonstrate that you get it.

Building some thought leadership content within specific markets is a great way to generate leads as well. Don’t hesitate to put your ideas out there as they’ll likely help you get connected to the right people.

Show your work

As a freelancer, your portfolio is your calling card.

These days, most potential clients care more about the good work you’ve done previously than they do about where you’ve gone to school. Past behavior tends to be the strongest indicator of future performance.

Potential clients are laser-focused on what you can do to help them reach their business goals. So the work that you show off should demonstrate exactly how you’ll help them achieve their many “jobs to be done.”

Think of your portfolio as the outfit you’d choose to wear to an interview. If you’re “dressing for the job you want,” your portfolio should dazzle potential clients and make them want the services that you’re offering for their own business.

Your portfolio of work is the most reliable indication of work quality that potential clients have to go on—and how you organize and share it speaks volumes about your freelance business.

Make sure it’s tight.

Be a learner

Every freelancer is on some sort of journey to increase their skills, grow their business, or at the very least maintain a stable list of clients.

That requires learning.

Clients’ needs will shift over time, requiring you to gain new knowledge and skills to sustain the working relationship you have with them over time. If you want to expand your services into new areas, you’ll need to learn those skills yourself or know enough to hire the right person with complementary skills.

Connecting to the points above, when you show your knowledge of various markets and share your work, you can also show potential clients that you’ve been on a learning journey and have grown your skills over time.

Demonstrate to clients that you’ve got that little intangible extra—a hunger to learn and grow—that could significantly enhance your work with them. It could be the difference between getting that contract or not.

Streamline your systems

Know your limitations.

For example, if you’re not a freelance accountant, hire a great one (or invest in top-notch accounting software). If research isn’t your strong suit, consider bringing on a virtual assistant to help.

Whatever the task, take a step back and decide what needs to be done by you versus what can be outsourced. Whether it’s a digital system or a human resource of some sort, you’ll need to be smart about the systems you build to support your freelance work.

This is often the hardest part for many freelancers—thinking like a business owner.

It requires them to step out of their domain expertise for a moment and engage with the less-than-sexy work of building business operations. Take the time to map out your time and monetary resources to better understand what sorts of systems you can afford while still running your business at an optimal level.


The other major trap for freelancers: Trying to do it all themselves.

It’s the dangerous side of our DIY culture. Sure, you might be able to cut some corners on expenses by spending a little extra time on those invoices or on business development—but that doesn’t make it a sound long-term strategy for your freelance business.

Instead, consider your freelance business goals and make some projections about how delegating certain tasks might help you get there more quickly. How could outsourcing key functions allow you to focus on more high-value work? What are you spending a lot of time on because it’s not within your skillset? How much is that costing your business?

Also, remember that delegating specific tasks allows you to help other freelancers while supporting your own business. And don’t forget that automation is a great way to delegate at a much lower cost, and such opportunities will only continue to grow.

Build human connections with clients

Here’s a big secret most clients won’t share: They hired you because they like you.

People don’t like to work with jerks or colleagues who make them feel uncomfortable. 

That’s why everyone talks about “cultural fit” in workplaces these days. And while some of that thinking can go unfortunately awry and reduce opportunities in the workplace for certain groups, most companies are genuinely trying to ethically and fairly find the right people to work with.

One of your goals as a freelancer is to make the experience of working with you feel comfortable and seamless. You should be able to fluidly embed yourself within a client’s workstream while also adding value through your own unique contributions.

Don’t just dive into the work with clients. Take a real interest in their backgrounds and expertise. Make an effort to get to know them outside of their specific roles. Share a bit of color commentary about your life outside of work so they can see you as a well-rounded person.

These human connections will make potentially challenging conversations about the work go much more smoothly. Building rapport with clients is a great way to ensure retention, as well. Most importantly, it just makes the workplace that much more enjoyable.

Working freelance in 2020 demands the right platform for success.

The steady increase in the number of freelancers only heightens the demands already put on the freelance workforce.

Competition is going up as new freelancers flood the market, income continues to be a major concern for freelancers, and clients are looking to get more mileage out of every freelancer with whom they work.

Freelancers being asked to continue delivering their core services at a high level of quality while also excelling at core business management functions and growing into service offerings. To make that possible, many freelancers are turning to all-in-one platforms that automate and accelerate how their freelance businesses operate.

In other words, modern freelance success demands a strong foundation.

These days, that foundation is a system that handles things like proposals, contracts, invoices, and expenses. As a freelancer, your livelihood is in those margins between what you bill to clients and what the real costs are for you.

Make sure you invest in a platform that maximizes your time and keeps you focused on your clients.