As part of a native advertising assignment, I developed this branded content pitch for Upwork, targeting the gig economy audience of Forbes.
This native ad presents a first-person narrative backed by freelance strategies and data insights on platforms like Upwork. It’s styled to blend into Forbes' editorial voice while positioning Upwork as the go-to platform for sustainable freelance careers.
I centered storytelling around my lived experience as a full-time creative director and freelancer. Paired with data, branded visuals, and CTA design strategies, it demonstrates how relatable storytelling and brand alignment can build trust while meeting user needs. It’s a reflection of my ability to merge authenticity with brand goals.
The Side Hustle Economy:
Can You Really Make a Living Freelancing?
Can You Really Make a Living Freelancing?
By Selena Carter | Sponsored by Upwork
I’m a Creative Professional, with 20+ years of experience, who is taking the leap into entrepreneurship.
I’m a Creative Professional, with 20+ years of experience, who is taking the leap into entrepreneurship.
For years, I believed that success meant climbing the corporate ladder—steady paychecks, a retirement plan, and the comfort of knowing where my next project was coming from. My mom has worked for the same company for almost 35 years. I may not have that level of tenure but it sure feels like a slog either way. As someone who thrives on creativity and connection, in an industry that is always evolving, I often felt like I wasn’t. I wanted more flexibility and ownership of my work. But most importantly, the freedom to choose the projects that excited me and where I worked on them. That’s how I knew it was the digital nomad life for me.
That’s why I started freelancing, but I didn’t do it alone. While I still work full-time, my path toward freelancing has been shaped by the mentors, friends, and circles of entrepreneurs I’ve intentionally networked with. These are the people who have made the leap before me, who showed me what’s possible, and who introduced me to Upwork. The platform that changed their careers and their lives. But could it help me change mine?
The Rise of the Freelance Economy
Over the last decade, freelancing has shifted from a side gig for extra cash to a legitimate and pivotal industry career path. According to Upwork’s Freelance Forward Report, 64 million Americans freelanced in 2023, representing 38% of the U.S. workforce.
According to the data, this shift is driven by a few things:
• People want to work on their terms, not someone else’s schedule.
• Corporate layoffs and job instability leave professionals wanting to explore alternative income streams.
• Platforms like Upwork are making it easier than ever to connect with clients globally.
These points were certainly true for me. For professionals considering freelancing, these numbers seem quite encouraging. The data shows that full-time freelancers earn as much or more than they did in traditional jobs. But I can attest, making the leap takes more than just talent. It requires strategy, persistence, a willingness to build your business.
Learning from Those Who’ve Made the Leap
During my time in house and in agency, I’ve networked with some amazing people. Sure, some loved their jobs. Others felt stuck in corporate roles but are now thriving as independent professionals. Their stories gave me the confidence to start my own transition and have been guiding the roadmap to do it right.
My longtime friend and mentor George, for example, was a senior copywriter at a marketing agency I worked with for a few years, always meeting tight deadlines, but never feeling like he had control over his work. When the company downsized, he decided it was now or never. I found another job. He signed up for Upwork, landed his first gig within a week, and started stacking contracts. Now, he works with global brands, sets his own hours, and has doubled his income compared to his old job.
Sophia, a fellow creative mom, was juggling a full-time graphic design job and family life when she realized she needed more balance and more income. She started with small illustration gigs on Upwork, and within months, she had a steady stream of projects and regular clients. Now, she’s a successful freelancer working from home, giving her the flexibility to be present for her kids while still growing in her career and taking it to places she never expected.
My mentor Tony, a creative powerhouse in multi-cultural agencies, was one of the first Black art directors I had ever met. When we met though, he was feeling burnout creeping in after years in agency. He’d grown in the ranks in Austin, Texas and was finally in what’s considered the multi-cultural Ad mecha – Atlanta, Ga. But, the long hours and the client pressures took a toll on him. He started freelancing on Upwork part-time, like I am now, taking on design work that truly excited him. Within a year, he had built a strong client base and took the leap into full-time freelancing. Now, he remotely during his travels and has the creative freedom he always dreamed of.
Turning a Side Hustle Into a Full-Time Career
Unlike my friends and mentors, I haven’t quit my full-time job yet, and most successful freelancers don’t either. Transitioning from a steady paycheck to freelancing takes planning. I’m grateful I built a village of mentors who have found success and shared their insight on the best way to do it : step by step. Especially for a single mom like me. Here are some of the tips I use to get closer to my goal of being a digital nomad:
1. Identify What Makes YOU Marketable
Not every skill translates into a high-earning freelance career, so the first step is figuring out what people will actually pay for. Upwork’s data shows that some of the most in demand freelance skills include graphic design, copywriting, digital marketing, web development, and consulting.
https://www.upwork.com/research/in-demand-skills-2025
For me, I’m leveraging my background in public speaking, brand strategy, design, and copywriting, which are all marketable and things I genuinely love doing. If you know anything about designers, you’ll know that not many love speaking in front of a crowd, let alone a team of CEO’s.
2. Get yourself out there — on Upwork
One of the biggest challenges in freelancing is finding steady work. A strong profile includes your resume and portfolio, and it’s how potential clients decide whether to work with you. Tony, George and Sophia all told me the below are key and they’ve worked for me:
• Highlighting real results for past clients like testimonials.
• Narrowing down a niche to stand out in.
• Crafting a compelling pitch that solves a client’s problem.
• Narrowing down a niche to stand out in.
• Crafting a compelling pitch that solves a client’s problem.
3. Be real about your income goals
“The dry spell” is one of the biggest reasons people hesitate to go full-time freelance. Having a stable consistent income is comfortable. As a single mom, I know that’s the one thing that keeps me from jumping ship and diving head first into a full-time freelance career. That’s where platforms like Upwork come in.
https://investors.upwork.com/news-releases/news-release-details/upwork-study-finds-59-million-americans-freelancing-amid
My friend Sophia made sure she had three months of savings before quitting and had the loving support of her husband, while my mentor Tony diversified his income with a mix of one-off projects and long-term contracts to create more stability. Whether you have support at home like Sophia, are dependent-free like Tony or a single mom, like me, it’s important to know the difference between what you need and what you want.
4. Self-employment is challenging – but you CAN overcome.
Adulting is hard. Every career has challenges and freelancing is no different. I’m glad I had my friends and mentors to share some of their obstacles and solutions with me early on:
• Create a buffer fund before transitioning and setting up recurring contracts with reliable clients. It’s better to go in with some cash and clients than to start from empty with no safety net.
• Setting clear boundaries with clients helped them avoid burnout and it’s easy to work ALL THE TIME when running your own business. Don’t become your own toxic boss.
• Imposter Syndrome can be good for you! Work through it. It’ll keep you fighting to be the best. Just don’t let it hold you back. We have to focus on results and client success stories rather than self-doubt.
• Don’t hesitate to pitch a project at a price point you think is high if you’re questioning your current rate. You’d be surprised how many yeses confidence will get you, even if you “fake it ‘til you make it.”
Freelancing Is a Lifestyle, Not Just a Job
Now that I’ve seen firsthand how freelancing has changed the lives of so many, first-hand, I know it’s not just a dream. It’s doable. They’ve proven that with the right tools, the right network, and the right mindset, you can take control of your career.
For those considering the leap, my advice is this: surround yourself with people who’ve done it, learn from them, and take the first step. Platforms like Upwork make freelancing more accessible than ever, and with the right approach, you can absolutely turn your side hustle into a thriving career. I hope to take the final leap next year. I’d say wish me luck, but based on my trajectory, hard work and the regular flow of clients I’m building on Upwork, I think I’ll just say – Join me!
Ready to make the jump? Set up your profile on Upwork today and take the first step toward freelancing on your own terms.