Becoming the CEO of Your Career - Looks Like Work, Season 1, Ep 9
There are career pivots, and then there’s Maya Grossman—who went from 24/7 travel agent to tech marketing executive to Silicon Valley CMO… and then walked away to become a full-time career coach.
In this episode, Maya shares how she built a 15-year marketing career that spanned Microsoft, Google, SodaStream, and more—by being intentional, proactive, and unafraid to ask for what she wanted (including creating her own job before it existed). But when the dream job stopped feeling like a dream, Maya did what most people don’t: she reinvented.
We talk about burnout, ambition, mindset, and why the real key to career success is asking one deceptively simple question:
👉 “What am I optimizing for?”
what we talked about:
Starting out as a travel agent and working up to tech executive
Building a brand for Microsoft for Startups from scratch
The moment she realized she was climbing the wrong ladder
What it really takes to pivot—yes, even at the top
Turning a side hustle into a business (with systems and strategy)
Reframing success through ownership and impact
Using LinkedIn (and consistency) to build authority
Favorite Takeaways:
“You own your career. Not a company. Not a manager.”
“You don’t find your passion. You create it.”
“Career planning is like going to the gym. You won’t get a six-pack after one workout.”
If you’ve ever felt trapped by your title, burned out by your “dream role,” or unsure how to pivot without burning it all down—this one’s a permission slip and a playbook.
Maya’s Guiding Question:
“What am I optimizing for?”
Whether you’re chasing a promotion, a sabbatical, or a softer life with sharper boundaries—this one question can change everything.
“I don’t think I had anything special—just awareness and initiative.”
Listen to this episode on Spotify | Apple | Wherever you get your podcasts
Resources & Mentions:
Catch up on previous seasons of Looks Like Work wherever you get your podcasts: Spotify | Apple | Podbean
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