• Chris Lawrence

How to Start Freelancing on Upwork in 2020:

Updated: Oct 12, 2020

One of the most common questions that I get on a daily basis is how others, friends, family — even people who follow me online, are growing more curious about whether it's possible to make an income that is based online and completely remote from an office setting. Upwork recently completed research that discovered a spike in the number of Freelancers in 2020; noting that about 36% of US workers reported that they were freelancing during the ongoing pandemic caused by COVID-19.

"Upwork’s seventh annual study surveyed more than 6,000 U.S. workers over the age of 18 and found that 59 million Americans performed freelance work in the past 12 months, representing 36% of the U.S. workforce, an increase of 2 million freelancers since 2019 [...] contributing $1.2 trillion dollars to the US Economy" - Upwork Press Release

The uptick in Freelancers in the US continues to grow as more companies turn to the flexibility of remote employees and having the ability to hire staff from around the world. But as the demand for remote workers grows, it can be daunting to get the ball rolling and land that first client.

Disclaimer: This article isn’t meant to be a one-click solution that fixes everything, and you most certainly won’t strike gold right away. While it’s possible, be prepared to do the work.

Finding Freelance Work:

A lot of people who asked questions simply just had no clue where to start. “Where do I FIND clients?” “How long till clients find me?”. These are all really good questions, but there’s not only one answer. Don't worry - you aren't completely on your own. As of 2020, I solely use Upwork for scouting projects because I've been able to connect with companies that relate to my interests and skills as a copywriter. Upwork isn't paying me to say all this, I'm just a huge fan of the platform.

Invest in Yourself & Your Skills:

As a copywriter, I intentionally block off a specific time each week to invest in my skills. Schedule time in your week to advance your craft, ensuring that you can further specialize your skills and learn other areas within your field that clients tend to need additional help. This brings me back to Upwork - because the projects are mainly out in the open for all to see, I keep track of the types of projects that I notice companies are constantly searching for. In August, I realized that SEO and Email Marketing projects were showing up on my feed more frequently, and I took a foundation course in both areas. The best part - it was free!

Keep Your Clients Coming Back For More:

You may think that the goal is to get your client to send their payment and that’s the end of the story, but that’s untrue. Every client that I work with, I strive to provide them with a level of service that is not only above their expectation but always want to keep them coming back to me anytime they are looking for similar work done. Freelancing is a competitive field, the number of Freelancers grows rapidly each year. Build an experience from the first moment you get in contact with a potential client; make it personal to the person who will read your proposals. Sending a Copy and Paste "here's how I can help" script with very little signs that you know about their company or project needs is an easy way to get overlooked. Create conversations that lead to solutions - don't put everything on auto-pilot.

Use Tools that Support Your Workflows:

Automation is a great way to not only build a seamless experience for your clients, but it also helps minimize certain administrative tasks that can take longer than they need to - like finding the perfect time to have an Introductory Call with a new client.

You: "How does 3 PM work for you?"

Client: "I have another meeting at that same time. How about 12 PM?"

You: "I can't do 12 PM, unfortunately - how about..."

Does this sound familiar? Notice how much back and forth this interaction is taking from both people. To avoid this, I use Calendly to handle all of the scheduling of my meetings because I set the times that I am available in advance, and send the link as needed. This reduces the back and forth, but also reduces the chance of being double-booked at the same time.

If you ask me, there's never been a better time to start exploring your options as a Freelancer. You never know what lies ahead and the awesome clients that you'll meet along the way.


This article was originally published on Medium in 2019 and has been updated since the original publication. Any hyperlinks in this article are not affiliate links and do not benefit me financially if you sign up. All thoughts are my own, and research has been cited.

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