4 Dynamic Female Professionals Share How They Took Control of Their Professions as Freelancers

Jean Weiss
Jean Weiss
March 8, 2021
March 8, 2021
4 Dynamic Female Professionals Share How They Took Control of Their Professions as Freelancers

There’s no way to sugar-coat how difficult 2020 was, especially for working women. Nearly 3 million women in the U.S. have lost their jobs since March 2020, forced to scramble to make ends meet in the midst of an unprecedented crisis. And for those that kept their jobs, more working moms than dads were saddled with juggling childcare and home-based education. The impact has been especially tough on single moms. To make matters even worse, the pandemic-induced recession has caused a wage gap between men and women of 5 percentage points.

But there’s good news on the horizon, especially as we turn our focus to celebrate International Women’s Day on March 8. Many women are regaining control and revitalizing their professions as freelancers. They’re finding steady, flexible and sustainable work through talent platforms like Upwork. Here are the stories of four successful professional women who made the leap and never looked back.

A viable path to launch or restart your career as an independent professional

Shari Cruz

Shari Cruz
Area of Expertise: Instructional Design
Years on Upwork: 10
Earnings to-date: $200,000+

Shari Cruz had just graduated with a master’s degree in educational leadership when she was first introduced to Upwork. A military veteran, Cruz was discharged from the U.S. Marine Corps following a hip injury. She used the remains of her GI Bill for graduate school. When it came to finding a new job, she faced a number of hurdles. She was newly married with a newborn, and her husband was an active-duty service member, which meant frequent moves.

Cruz applied to and considered several entry-level positions, but none made sense given the salaries and amount she would need to spend on childcare. She was looking for something that would keep her professionally challenged while giving her flexibility to move on a dime, and, if needed, parent solo.

She came across Upwork and found jobs that not only were a better fit for her skill set but also enabled her to work remotely. “Upwork was the first step I needed to find my professional path and has continued to be a consistent source of reliable work and income no matter what other twists life has thrown along the way,” she said.

Cruz’s strategy paid off. Working with clients through Upwork, she quickly gained new skills and confidence, winning clients and building out her expertise across a variety of industries, departments, and organizations.

Cruz also quickly realized she could use Upwork job postings as a way to track the skills she needs to stay competitive. “Over the years, this has led to me learning a multitude of new software and trying out several new approaches relevant in my industry.”

Cruz is now ready to go after a doctoral program in instructional design. “Knowing that I have Upwork as a flexible but reliable source for income is what allowed me to apply to that program.”

When COVID hit, her flexible freelance schedule allowed her to quickly adjust to changing family needs, including a military transfer from Hawaii to Maryland. “I was able to scale my projects to accommodate,” Cruz said. “When everything else was unknown and unsteady, my family and the work that I needed for my own sense of purpose and sanity were still there as my rock.”

Cruz encourages others to view Upwork as a viable way to achieve their own professional goals. For those just starting out, she suggests spending a week researching what clients are looking for before setting up your profile. “Take note of the key technology, skill sets, and requirements that you see dominating the feed,” Cruz said. “Then, set up your profile using the relevant keywords that align between what you have to offer and what you see being requested. If needed, take the additional time to create some sample work. Then, start bidding! It's an active platform, so don't get discouraged if you don't land a project right away.”

Cruz said to customize your cover letter every time. She also suggests using downtime between projects to learn new skills. “If there are any skills that you see requested that you don’t possess, take the time to upskill while you wait to land your next contract. Once you get a couple of bites, the feedback loop will help build your credibility on the platform and the bigger fish will start to see you too.”

Fulfilling work, with a flexible schedule to care for family

Shari Stephens

Shari Stephens
Area of expertise: Marketing Strategist
Years on Upwork: 2
Earnings to-date: $100,000+

Life turned on a dime for marketing strategy expert Shari Stephens when her husband had a stroke, and she became the sole family earner. She needed to work from home so she could oversee and navigate the new normal. She turned to Upwork for flexibility and found unexpected positives along the way.

Working on Upwork allowed Stephens to structure her own schedule so she could take her husband to the medical appointments needed to return him to good health. When she and her husband adopted two children, now ages 7 and 5, the schedule flexibility again came in handy. Stephens could still work and care for her kids, with enough free time to build strong family bonds.

The silver lining for Stephens is that, despite life’s setbacks, she’s enjoyed a satisfying career as an independent professional. She’s expanded the scope of skills that she offers to companies of all sizes, including the Fortune 500, and built a reputation for doing good work. “I have been everything from stay-at-home mom to a national brand strategist for corporate America,” Stephens said. “Freelancing has been one of the most fulfilling professional experiences for me.”

Stephens was relieved that she’d already made the transition to freelance before the pandemic began. “Otherwise, there would have been no real way to work, as my husband and I are both high-risk,” she said. “The opportunity that I have via Upwork has kept my family afloat and safe. Even with the children being able to attend school virtually, the flexibility I have in creating my own schedule has made this easier to ensure income is coming into the home.”

Stephens encourages anyone with a marketable skill to consider freelancing, saying work will always be there for qualified and experienced individuals.

Her tips for success are to be consistent, follow up, and bid on opportunities daily. “Do great work and build relationships with your clients,” Stephens said. “Give them the same great customer service you would if you worked for someone else. Understand that you are a business owner and that you have the benefit to work on your own terms and do what you enjoy. You have the benefit to work on your terms and do what you enjoy. If you find yourself in need of flexible professional opportunities, Upwork provides a dynamic platform for finding them.”

From toxic marriage to financial freedom and flexibility

Jenn Lester

Jenn Lester
Area of expertise: Email Marketing
Years on Upwork: 5
Earnings to-date: $100,000+

Jenn Lester was leaving a toxic marriage after 16 years and looking for a way to support her two teenage boys and a baby as a single mom. She’d always been a strong writer, so decided to try her hand at freelancing. “Given our circumstances, I didn't want to be away from my children 40-plus hours a week working full-time,” she said. So she explored a few talent platforms that would allow her to work from home when she wanted and settled on Upwork because she thought it offered the best opportunity to chart her own path.

Her choice paid off. Lester started out small, charging only $15 an hour but quickly gained experience and positive feedback, and she upped her skills. The work allowed her to support her family financially and be there when they needed her.

Eventually, she increased her rates. In one year, she doubled her income. Now, she’s raised her hourly rate to $125 and typically works about 15 to 20 hours a week. Lester is especially appreciative of recent changes on Upwork that make it easier to grow her business, like Project Catalog, and fast access to payment.

Today, because of freelancing, Lester has created the lifestyle she wanted. “It didn't happen overnight, of course, but sticking with it, serving my clients well, and continuing to up my skills has allowed me to reach a point where my family is comfortable,” she said.

Lester now has time to volunteer at her kids’ schools, take classes to improve her writing skills, and workout, including pursuing her passion for running. “I’m participating in a series of races across all of the different ecosystems in Texas—this weekend, it’s the Chihuahuan Desert and, next month, I'm racing through the mountains,” said Lester. “I wouldn't have had the time or money to do this if my work situation were different.”

Lester has been strategic in how she uses Upwork to identify new professional opportunities. She scrolls through projects and rates to see what's in demand and how much businesses are paying. Then, if it's a niche she’s interested in, she’ll fine-tune her skills in that area.

Email marketing is one area she’s noticed is really hot. “That's where I'm focused these days,” Lester said. “I took a course and it's paying off.”

Lester is also hoping to launch an agency on Upwork and creating a personal blog focused on her passion for running and how she funds it through her freelancing business. “I'm also helping my son, who is about to graduate from high school, get set up on Upwork,” she said. “What better job in college than one where you can set your own hours and determine your own income? He's sold on it too.”

The pandemic took its toll on Lester, as with everyone else, especially in the beginning. “I was suddenly faced with three kids at home, plus me trying to work from home and keep my head straight,” she said. “I was really busy from February through May ... and, honestly, it was hard to balance it all because there are so many opportunities and companies that use Upwork. So, if one of my clients was impacted by COVID and no longer needed me, there was another client just around the corner who had pivoted their business and was in need of my services.” The work stream continued consistently, allowing Lester to take a summer break to focus on her kids.

Lester often gets offers of full-time work and always turns them down because she loves the freedom and autonomy that freelancing on Upwork provides. For others wishing to try a similar path, Lester said the commitment pays off. “It might feel overwhelming or intimidating at first,” she said. “There's a learning curve, and you've got to build trust and credibility. It took me about six months to reach the point where I felt like I could build a sustainable freelancing career. But I am so glad that I did.”

Hassle-free connection to clients and time for the work that matters

Laura Pennington Briggs

Laura Briggs
Area of expertise: Content
Years on Upwork: 6.5
Earnings to-date: $400,000+

Freelance as an independent career path is here to stay, said content expert Laura Briggs. Briggs has tapped into a global client base through Upwork that’s added income streams to her content business and given her the opportunity to work flexibly, become a book author, TEDx speaker, and even start a nonprofit teaching military spouses how to freelance from anywhere. “I love that Upwork helps connect me with clients,” she said. “It’s allowed me to take my independent career anywhere, which was vital as my husband was on active duty in the U.S. Navy.”

Along the way, said Briggs, running her own freelance business has helped her learn how to negotiate contracts like a pro, and gain confidence as a business owner. It’s also provided an essential heads up when she needs to develop additional skills to quickly adapt to a constantly changing workforce. “Upwork gives me my first clue that a skill is in demand because I can literally see it popping up in job postings,” said Briggs. “I've been able to charge more, work with better clients, and learn many new things because of this.”

During COVID, freelancing provided stability and steady income. “Knowing that there is always a place I can turn to generate more income if I wanted to is a huge help to me,” said Briggs. “I also love that I have a place where people can see actual client feedback. That social proof is powerful and helps when clients are nervous about hiring a new freelancer. My presence on Upwork has definitely helped raise my visibility and profile overall.”

Briggs said she has earned more than $400,000 during her time on Upwork and has formed long-lasting relationships with clients.

Take control of your professional goals on Upwork

Despite the unprecedented hardships and setbacks faced by millions of working women due to the impact of COVID, there is hope for a better future. As the experiences shared by these four women show, no matter what the reason or circumstance, there’s always an opportunity to continue in your professional life where you left off or begin anew.

At Upwork, we are committed to helping women create a professional path that meets their needs and their schedules on their own terms. Are you ready to start building your career as an independent professional on Upwork? Sign up to get started today.

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