FREELANCER SPOTLIGHT: Lindsey Flagg

At Freelance Insider, we highlight the real stories behind freelance work. How people get started, what they’ve learned, and what keeps them going. This week, we’re featuring Lindsey Flagg, a digital marketing consultant who has carved out a career that blends strategy, execution, and continuous growth.

The Path to Freelancing

Lindsey began freelancing two years after college, but her journey started well before that. With professional experience in education, sales, and digital marketing, she developed a versatile skill set that made independent consulting a natural fit. It wasn’t a straight path, but it was the one that allowed her to fully use her strengths while creating a career on her own terms.

Today, Lindsey provides digital marketing support to a range of clients across industries. Her services include social media management, content writing, blog scheduling, keyword research, and marketing operations. She also creates graphics and video content using platforms such as CapCut, Canva, and Final Cut Pro. It’s a blend of creative and tactical work, something she’s grown to love.

What Sets Her Apart

Lindsey brings a full-picture mindset to everything she does. Her background enables her to think like a strategist while handling the detailed tasks that keep digital campaigns running smoothly on a day-to-day basis. Whether she’s developing a content plan or scheduling blog posts, she understands how the pieces fit together and how to keep them moving.

What truly sets Lindsey apart is her commitment to learning. She doesn’t wait for someone to tell her what to study or adopt. She takes the initiative to attend webinars, pursue online courses, and teach herself the tools her clients need. This mindset hasn’t just made her more skilled; it has directly led to new contracts and long-term partnerships.

“Continuous learning is more than helpful as a freelancer; it is vital.” Lindsey said.

The Role of Community

In addition to technical growth, Lindsey points to her involvement in volunteer work and professional organizations as a major contributor to her development. These experiences have expanded her network, improved her communication skills, and helped her stay connected in a field where many work solo.

She encourages other freelancers to do the same. Whether it’s attending local events or volunteering in a professional capacity, staying connected to a broader community has made a real difference in her journey.

A Career That Keeps Evolving

Lindsey is still growing, still learning, and still finding new ways to deliver value to her clients. She doesn’t claim to have all the answers, but she’s proof that freelancing can be a powerful career path when you combine curiosity, adaptability, and a willingness to show up and figure things out.

📍 Indiana, Greater Chicago Area
🔗 Connect with Lindsey on LinkedIn

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