How to Get Started With Freelance Writing Through Upwork

Today, I have a post from Kevin Flynn.

If, at first, you don’t succeed, try and try again. Persistence is the key when it comes to any new business venture. I learned this early on when I decided to become a freelance writer. My goal was to do it full-time at some point, but that didn’t happen overnight.

My journey began nearly 20 years ago. It started as a mission to pay off debt. My income wasn’t covering my overhead. Credit card balances were climbing, rent payments were late, and utilities were always on the verge of getting shut off. Something needed to change.

Social media was in its infancy at that time. Sites like Myspace and Friendster were the “next big thing.” Mark Zuckerberg and Eduardo Saverin were pushing a new site called The Facebook. Twitter and Instagram weren’t even concepts on a whiteboard yet.

This was the world I lived in. I believed that doing business online was the future, but I had no real evidence to support that belief. Despite that, youthful enthusiasm took over, and I created a profile on a freelance website called Elance, which would eventually become Upwork.

Freelance Writing Through Upwork

Creating Your First Writer Profile

No one gets it right on the first pass. As writers, we learn that early on. When I created my first writer profile, I made many mistakes. It was evident through the body of work I displayed that I had minimal experience, but I “overinflated” my profile to try to land better jobs.

It didn’t work. Potential clients saw right through it, and I was deluged with low-paying jobs for questionable clients. I was desperate to get started, so I took my first offer. The client was a Las Vegas escort site that wanted erotica content: two cents a word.

I’ll get into the dangers of underselling yourself below. For now, new writers need to understand that honesty truly is the best policy. If you’re new, write your profile based on your education, motives for being a writer, and short-term goals. Someone will hire you.

As time goes by, you can modify your profile and add published work. If you pretend to be someone you’re not in the beginning, you won’t meet expectations, and your online reputation will suffer. Enter the freelance world as a newbie, and you can build momentum.

Setting Your Price to Make Writing Worthwhile

I wrote one-hundred 500-word articles for that first client and made a whopping $1,000 on the job. It took me over to month to complete the project. At the time, I still viewed writing as a “side hustle,” so it was all just extra cash to me. It certainly wasn’t going to pay my bills.

Most of my friends thought I was nuts, and they were right. I justified the lower word rate because I was “new,” and I thought I’d get offered higher-paying projects as I gained more experience on the platform. I was wrong. The two-cent jobs kept on coming.

Elance didn’t have the same features as Upwork today, so I couldn’t see what other writers were making. I could only see their bids, and I always went low to win jobs. It wasn’t until 2015, when Upwork took over, that I learned about premium business models.

Studying economics will teach you that charging a higher price for premium service will give you a more sustainable business model. I made $4,000 in my first year as a freelance writer. I’ll make $75,000 this year, and I work fewer hours. I did that by raising my prices.

This is one of the keys to being a successful freelancer. With Upwork, you can do searches for any position and find out what everyone else is charging for an hourly rate. Don’t set yours low to underbid everyone. Real clients prefer quality over discount pricing.

Finding a Niche Market and Owning it

I am a financial writer with a 99% job success score and a “Top Rated Plus” rating on Upwork. That didn’t happen until I stopped being a general article writer and started doing financial content exclusively. Check the job board. Financial writing pays 400% more.

No, I did not simply declare myself a financial writer and re-write my profile. The niche I’m in requires specialized education. While I was still writing part-time, I took a job as a fintech coach and went back to school for accounting and finance.

This is another point I want to hammer home. You can make a nice part-time income on Upwork and still work a regular job. I used that part-time income to learn something that would help me increase my writing income. Today, I don’t need another job.

Financial writing isn’t the only high-paying writing niche on Upwork. Technical writing pays well, as does sales copywriting if you’re into that type of thing. I’m currently learning all I can about the cannabis space. That’s a “budding” niche market with a bright future.

Own your space. I rarely put job bids in because I have steady clients. They come to me when they need something. That could be weekly, monthly, or occasionally. It all balances out. I even have Upwork recruiters sending me jobs now.

Maintaining Long-Term Client Relationships

Constantly searching for new jobs is a tough way to make a living, but we all need to do it when we first start. It’s what makes freelance work so stressful. That’s why seeking out and maintaining long-term client relationships is essential. I have several that are over five years old.

A “good” client likes my writing style and isn’t constantly complaining or asking for re-writes. I’ll accommodate the negative folks when they come along, but I never take a second job from them. I am always available for good clients.

I start each week by sending a message to all my steady clients to let them know I have the capacity to do work for them that week. I let them know if I’m taking some downtime or going on vacation. I no longer fear losing a client because I’m not available 24/7.

Speak to your clients. I do all my work through Upwork because the payment system is secure, and I only pay them 5% on most of my jobs. That doesn’t mean I can’t call or do a Zoom meeting with a client. The better they know me, the less likely they will go elsewhere.

Set Up an Accounting and Record Keeping System

Upwork won’t send you a 1099 unless you make over $20,000. That doesn’t mean that you shouldn’t report the income. They are making direct deposits into your bank account, so there’s a money trail there if the IRS decides to look at your finances.

When I switched to financial writing, I set up an LLC and subscribed to FreshBooks to keep track of incoming payments and expenses. Other freelancers, I’ve spoken to use QuickBooks. Some keep track of things on an Excel spreadsheet. It doesn’t matter how you do—just make sure you track your earnings to minimize the headaches come tax season.

On February 1, 2020, I quit a job making over $100K a year to become a full-time freelance writer. I’ll easily make $75K this year and never work more than 30 hours a week. It took me a few years to get here, but I’m happy I put the time and effort into it. You can do it, too.

Kevin D. Flynn is a former fintech coach and financial services professional. When not on the golf course, he can travel with his wife or spend time with their eight wonderful grandchildren and two cats.