Episode 15 | The Lie of the Career Ladder: Kathleen Ross on Finding Freedom, Leadership, and AI
What if the career ladder you’ve been climbing… isn’t actually taking you where you want to go?
This week on Marketing Your Way, I’m joined by Kathleen Ross — award-winning CMO, creative leader, and fractional brand strategist — for a real and refreshing conversation about what it really takes to build a career that aligns with your life.
From publishing to product launches, from corporate burnout to reinvention, Kathleen has seen it all. She’s worked with some of the world’s most iconic brands — BMW, Vera Wang, MONAT — and now helps marketing teams navigate creative leadership and AI innovation on their own terms.
5 Key Takeaways:
1. Your corporate career is your launchpad.
Kathleen credits her years in publishing, events, and global brand marketing as the foundation that made her successful as a fractional CMO and consultant. The network, skills, and leadership experience she gained were invaluable in building her own business.
2. The “career ladder” is a myth.
Careers rarely move in straight, predictable steps. Kathleen’s path looked more like a roller coaster—full of pivots, side hustles, and unexpected connections that shaped her trajectory.
3. Burnout can be a turning point.
Kathleen experienced burnout three times in her career. Each time, it pushed her to pause, reassess, and make changes—sometimes leading to completely new opportunities she wouldn’t have found otherwise.
4. Entrepreneurship isn’t automatically “better.”
Running your own business brings flexibility and choice, but it’s not easier than corporate life. Both paths have challenges, and the right fit depends on your personality, values, and season of life.
5. AI is an amplifier, not a replacement.
Kathleen is passionate about helping marketers use AI to enhance their creativity and productivity. She emphasizes the importance of women being part of shaping AI tools to reduce bias and create better outcomes.
Connect with Kathleen:
· Instagram: @kathleenrosscreative
· LinkedIn: Kathleen Ross
· Website: www.kathleenrosscreative.com
Resources & Mentions:
✔️Book: Time Traps by Todd Duncan*
✔️FloDesk — the easiest, most beautiful email marketing platform out there. Stunning templates, simple automation, and no list limits. Get 50% off your first year: Sign up here
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Hi, I’m Anastasiia!
Ukrainian-born, Miami-based, and someone who spent over a decade building a successful marketing career before finally building something that felt like mine.
I didn’t leave corporate on a whim. I left because I wanted creative freedom, flexible time, and a business that aligned with my life — not the other way around.
It started as a freelance gig. Then a full roster. Then a boutique real estate marketing agency. Now, it’s also this — an education platform and podcast that helps women like you transition from “stuck” to “started.”
I’m here to teach you how to build a business that fits your goals, your energy, and your version of success.