We were lucky to catch up with Katherine Bailey recently and have shared our conversation below.
Katherine, appreciate you joining us today. Early in your career, how did you think through the decision of whether to start your own firm or join an established firm?
When I first started out, I was all about corporate life. My dream since high school was to work for Disney in some creative capacity, and I actually landed that dream job as a Marketing Strategy Associate at Disney Springs. But you know what they say about the best-laid plans, right?
In April 2020, the pandemic hit, and I found myself furloughed. Talk about a plot twist! But here’s the thing – I’m not one to sit around twiddling my thumbs. So, I decided to dip my toes into the freelance world. It was supposed to be a temporary gig, just to keep my skills sharp and pay the bills. Little did I know, I was about to stumble upon my true calling.
Fast forward to October 2020, and boom – layoff city. My Disney dream had come to an end, and I thought my world was crumbling. But you know what? Sometimes when one door closes, a whole hallway of doors opens up. I landed a Content Manager role at a big recruiting company, which was great on paper – promotion, fancy title, steady paycheck. But in my gut? I knew something was off.
After about six months of trying to convince myself that a steady paycheck was most important, I took a leap of faith. I quit the corporate gig and dove headfirst into freelancing. It was scary, exhilarating, and absolutely the right move for me.
Now, here’s where it gets really interesting. In June 2021, Disney came knocking again with an amazing opportunity – Digital Product Operations Manager, working on the parks and the 50th Anniversary Celebration. Younger me would have been over the moon. But you know what? After taking the role and returning to Disney on an amazing team, I realized that Disney wasn’t my dream anymore. Freelancing was.
In January 2022, I made the hardest (and best) decision of my career. I said goodbye to Disney (again) and hello to my freelancing LLC. And while I loved my team at Disney, let me tell you, I haven’t looked back since.
Looking back, I wouldn’t change a thing. Those twists and turns, the ups and downs – they all led me to where I am now. I’m living my passion every day, helping brands rock their marketing plans, crush their social media strategies, and nail their ad campaigns. It’s not just a job for me – it’s who I am.
So, was it the right choice? Absolutely. Would I recommend everyone jump straight into freelancing? Not necessarily. My journey taught me invaluable lessons about resilience, adaptability, and listening to your gut. It gave me experiences in different industries and roles that now help me serve my clients better.
For anyone out there wondering if they should take the leap into freelancing – here’s my advice: trust your instincts, be prepared to work hard, and don’t be afraid to pivot when something’s not working. Your dream job might not look like what you initially imagined, but when you find it, you’ll know. And let me tell you, it’s worth the journey to get there!

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
Hi there! I’m Katherine, a passionate Marketing Freelancer with a knack for digital storytelling and a love for all things social media. With over 7 years of experience under my belt, I’ve had the incredible opportunity to work with a diverse range of clients – from Fortune 100 brands to local businesses in the Orlando area and around the US.
My journey in the marketing world has been quite an adventure! I’ve worn many hats, from crafting magical experiences at Disney to supporting large marketing agencies. Each step of the way has taught me something valuable, shaping me into the versatile marketing pro I am today.
So, what exactly do I do? Well, I’m your go-to gal for all things marketing and social media strategy. As your dedicated marketing partner, I’m here to elevate your brand in the digital landscape. My comprehensive services include:
✨ Marketing Strategy: Developing tailored, goal-oriented plans that drive measurable results for your business.
✨ Social Media Management: Crafting engaging content and implementing growth strategies for both organic and paid campaigns to boost your online presence.
✨ Content Creation: Producing compelling written content across various formats, including blog posts, social media updates, and user-generated content that resonates with your target audience.
✨ Paid Social Media Advertising: Optimizing your ad spend through strategic campaign management, ensuring your message reaches the right audience for maximum ROI.
What sets me apart? It’s my ability to seamlessly blend into your team. I’m not just a freelancer you hire – I become a part of your team and brand’s story. I take the time to really understand your voice, your goals, and what makes your brand unique.
What am I most proud of? It’s the relationships I’ve built and the growth I’ve helped fuel. There’s nothing quite like seeing a client’s eyes light up when their social media engagement skyrockets or their ad campaign hits it out of the park.
If you’re looking to inject some fresh, strategic energy into your marketing efforts, I’d love to chat. Whether you need a complete marketing overhaul or just want to level up your social media game, I’m here to help bring your brand’s story to life in a way that captivates and converts.
And for those of you just starting your freelance journey, I’m happy to help! I’m passionate about sharing my experiences, tools, and insights with aspiring freelancers. If you’re new to freelancing and looking for guidance, feel free to connect with me on LinkedIn. I always love connecting with fellow freelancers and entrepreneurs.
Let’s make marketing magic, together.
https://www.creativelykatherine.com/contact
hello@creativelykatherine.com
https://www.linkedin.com/in/katherine-foote/

What do you think helped you build your reputation within your market?
Building a strong reputation in the marketing freelance world has been a journey of consistent effort and genuine relationship-building. Looking back, I can pinpoint several key factors that have contributed to my success:
1. Authenticity: In an industry often clouded by buzzwords and fleeting trends, I’ve always strived to be genuinely myself. This authenticity resonates with clients and fellow professionals alike, fostering trust and long-term relationships.
2. Reliability: Consistently delivering high-quality work on time has been crucial. In the freelance world, your reputation is only as good as your last project, so I’ve made it a point to exceed expectations with every client interaction.
3. Unique Blend of Experience: My background in both corporate environments and freelancing has given me a distinctive perspective. This diverse experience allows me to bridge the gap between traditional corporate strategies and the agile approaches needed in today’s fast-paced digital landscape.
4. Networking: I’ve actively engaged in both online and offline networking opportunities. Building genuine connections within the industry has not only led to new opportunities but has also helped me stay on top of emerging trends and best practices.
5. Consistent Content Strategy: LinkedIn has been a game-changer for me. By consistently sharing valuable insights, case studies, and industry observations, I’ve positioned myself as a thought leader in my niche. This regular engagement has significantly expanded my reach and attracted clients who resonate with my approach.
6. Continuous Learning: The marketing landscape is ever-evolving, and I’ve made it a priority to stay ahead of the curve. Regularly upskilling and adapting to new technologies and platforms has enabled me to offer cutting-edge solutions to my clients.
7. Client-Centric Approach: I’ve always focused on not just meeting client needs, but truly understanding their business goals. This approach has led to more impactful strategies and, consequently, stronger testimonials and referrals.
8. Transparency: Being open about my processes, pricing, and capabilities has helped set clear expectations from the start. This transparency builds trust and often leads to smoother, more productive client relationships.
By consistently applying these principles, I’ve been able to build a reputation as a reliable, knowledgeable, and authentic marketing partner. It’s been a gradual process, but the effect of these efforts has been instrumental in establishing my position with my clients and in the market.

What’s a lesson you had to unlearn and what’s the backstory?
The biggest lesson I’ve had to unlearn is the glorification of hustle culture that’s deeply ingrained in corporate America.
Early in my career, especially during my time at high-profile companies like Disney, I fully bought into the idea that success was directly proportional to the hours you put in. Late nights, working weekends, and being constantly “on” were badges of honor. I thrived on the adrenaline rush of meeting tight deadlines and being the go-to person who could handle anything.
But as I transitioned into freelancing, I began to see the toll this mindset was taking. The burnout was real, affecting not just my personal life but, ironically, the quality of my work too. That’s when I had to critically examine this “always on” mentality.
Unlearning hustle culture has been transformative. Here’s what I’ve come to understand:
1. Work is important, but it’s not my entire identity.
2. Quality over quantity in productivity.
3. Work-life balance is essential for long-term success and satisfaction.
4. Setting boundaries is necessary and respectful to both myself and my clients.
5. Taking time off is an investment in my well-being and the quality of my work.
Now, I still love working hard and giving my all to my clients. But I’ve learned to do it in a way that’s sustainable and healthy. I’ve set clear working hours, learned to say no to overwhelming projects, and made sure to carve out time for self-care and personal interests.
The result? I’m producing more valuable work for my clients, feeling more fulfilled, and ironically, seeing more success in my business. It turns out that when you’re not constantly exhausted, you have more mental space for creativity and strategic thinking.
This journey of unlearning has been crucial in shaping my approach to freelancing and how I mentor others. I always emphasize finding that sweet spot between ambition and well-being. Because a successful career should enhance your life, not consume it.
Contact Info:
- Website: https://www.creativelykatherine.com/
- Instagram: https://www.instagram.com/creatively_katherine/
- Facebook: https://www.facebook.com/creativelykatherine
- Linkedin: https://www.linkedin.com/in/katherine-foote/




Image Credits
Creatively Katherine Brand Photos – Sydney Tobin Photography

