Career Lessons + 5 Years of Building Marketing Happy Hour
Five years ago, Marketing Happy Hour was launched from scratch — Canva logo, Google searches, and zero podcasting experience. In this milestone episode, Cassie walks through the full arc of her career: from a self-pitched internship at a Florida restaurant group to a pivotal move to New York City, from leaving a stable agency job to start her own business in 2019, to building MHH into the community it is today. Cassie gets refreshingly honest about the comparison trap of entrepreneurship, why she stopped chasing the "big brand on the resume" and started following what she actually loves, and the one piece of advice she'd give her younger self.
Key Takeaways:
// Cold pitching with concrete ideas beats cold pitching with just your resume. When Cassie landed her first internship — at a restaurant group with no open listing — she didn't just ask "can I help?" She came with specific ideas and made it easy for the hiring manager to say yes. The lesson: don't make the person on the other end do the work of figuring out how you fit.
// The biggest career accelerator is often the move you're scared to make. For Cassie, that was packing up and moving from Tampa to New York City. It pulled her out of a hospitality bubble and into big brand, agency-level experience that changed everything. You don't have to move across the country — but being open to expanding the type of roles and environments you're in is what unlocks the next level.
// Build a career on what you keep saying yes to. Cassie still doesn't have a singular "dream job" figured out — and she's at peace with that. What she does know is the types of projects that light her up: podcasting, production, storytelling, events. Following that thread, rather than a fixed five-year plan, has shaped her career more than any roadmap would have.
// The comparison trap is real — but it can be reframed. Everyone's timing is different. Everyone's journey has challenges you can't see from the outside. Instead of comparing, Cassie recommends using other people's careers as a research tool: study how they got there, reach out, ask questions, and let it inform your own path rather than measure against it.
// Give yourself grace. The advice Cassie would give younger Cassie — and the one she still needs to hear. You won't be perfect every day. Not everything has to make sense right now. Be patient with the journey, surround yourself with the right people, and trust that the pieces are connecting — even when you can't see how yet.
Connect with Cassie: LinkedIn
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