The Real Story of Working as a Social Media Manager: Lessons from Building The Winfield Creative

What is it really like to turn your passion for social media into a thriving business that serves your community?

Hi there! It’s The Winfield Creative’s Marketing and Content intern, Jesse Sandler, writing after being able to sit down with Brittany and learn about her career trajectory and her business. 

When people think about social media management, they often picture someone casually posting photos and writing captions from a coffee shop. However, after years of building The Winfield Creative from the ground up, Brittany Winfield can tell you that the reality is far more complex, but also infinitely more rewarding, than that stereotype suggests.

From Fake Websites to Real Impact

Her journey into social media management didn't start with a business plan or a marketing degree. It began with curiosity and creativity while making up fake websites for fictitious businesses with her cousins when she was young. When social media became part of everyday life during Winfield's middle school years, she was naturally drawn to its power to connect people across distances.

It wasn't until 2020, watching her beloved local businesses close their doors because they couldn't pivot to digital marketing during the pandemic, that she realized social media management could be more than just a hobby. It could be a lifeline for businesses struggling to stay relevant in an increasingly digital world.

The Reality Check: Discipline Over Dreams

Here's what they don't teach you in business school: quitting your 8-to-5 job to work for yourself might seem like a dream, but it requires an extraordinary amount of discipline to not just run a business, but to build it from nothing.

Winfield cites one of her biggest early mistakes as trying to do everything at once and digging a mile wide instead of a mile deep. She offered websites, email marketing, and social media strategy, thinking more services meant more success. Instead, it led to severe burnout and diluted expertise.

The turning point came when she asked herself two crucial questions: “What brings me the most joy?” and “What generates the most revenue?” The answer was crystal clear: social media strategy. From that day forward, The Winfield Creative became laser-focused on being the go-to trusted experts for social media guidance for Vermont businesses.

The Moment She Became a Real Business Owner

The most pivotal moment in her agency's growth wasn't landing a big client or hitting a revenue milestone, it was firing a client for the first time. As someone who is a self-proclaimed conflict avoidant, having that mature, professional conversation was terrifying to Winfield. Though it taught her to trust her instincts when the energy doesn't feel aligned and to put both her business's needs and her own well-being first.

The result ended up being that she landed an even better client who she absolutely loves collaborating with. Sometimes saying no to the wrong opportunity creates space for the right one.

Meeting People Where They Are

What sets successful social media managers apart isn't just technical skill, it's understanding that not every business has the same resources or capacity. At The Winfield Creative, tiered mentoring resources are offered so even startups with limited capital can access social media education.

The firm’s signature presentation, "Social Media On Your Schedule," answers the question: "If you only have 15 minutes to give to your social media plan, what should you do?" Because while businesses could grow faster with more time investment, that's not their daily reality.

Blending Passion with Purpose

One unexpected advantage in Winfield’s social media management career has been incorporating her passions for mental health advocacy and comedy into her teaching approach. These aren't topics you typically see discussed in entrepreneurship circles, but they speak to her heart and professional experience, allowing her to create memorable, interactive presentations that truly empower attendees.

Building Relationships Beyond the Screen

Social media management is fundamentally about human connection, and that extends to how you build relationships with clients and community members. Winfield’s approach centers on three fundamentals:

1. Connect with curiosity - Ask questions and actively listen
2. Tell people when they come to mind - Share relevant articles or simply let them know you're thinking of them
3. Speak their language- Avoid industry jargon that confuses rather than clarifies

The Ripple Effect of Good Work

The most rewarding aspect of working as a social media manager in Winfield’s mind isn't the follower counts or engagement rates, it's the real change she creates. She has seen the reduction of stress and overwhelm around social media in her local community. She has watched connections form between real people through strategic online presence.

Winfield measures impact both through data progression and transformative feeling. When someone approaches her after a seminar to share their takeaways, she knows an immediate impact has been made.

Paying It Forward

Success in social media management isn't just about building your own business, it's about creating opportunities for others. Winfield guest lectures at universities, runs internship programs, and constantly connects job seekers with employers, small businesses with collaboration opportunities, and entrepreneurs with the creative services they need.

The Evolution Continues

In the past six months, The Winfield Creative has grown to the point where Winfield has brought on a full-time freelancer for content creation, freeing her to travel across Vermont and connect with more entrepreneurs. 

The Real Reward

Recently, Winfield feels that she has reached a turning point in her entrepreneurship journey. She finally feels like she knows what she's doing and that she belongs in this world. That feeling of confidence and belonging is what she is most proud of professionally.

Working as a social media manager has taught her that success isn't just about growing follower counts or increasing engagement rates. It's about using your platform to help others succeed, showing up for your community, and building something that creates real value in people's lives.

If you're considering a career in social media management, know this: it's challenging, it requires constant learning, and it demands more discipline than you might expect. But if you're driven by genuine curiosity about human connection and have a desire to help businesses tell their stories authentically, it can be one of the most fulfilling paths you'll ever take.

The key is remembering that behind every screen is a real person with real goals, real challenges, and real dreams. Your job isn't just to manage their social media—it's to help them connect with their community in meaningful ways. And in doing so, you'll find yourself more connected to your own purpose than you ever imagined possible.

And if you’re considering hiring a social media manager, find someone who can meet you where you are and with whom you can have an open dialogue with. You should be able to connect with who is helping you connect.

In the end, the most important thing is that you do what feels right for you and your business.