On The Career I Almost Left
Reactive vs. intentional--the difference changes everything
Another career and life pivot point post growing a LIB → 26M in 2 years, a move to CA, and two under two.
Esther Perel says we can have two or three marriages to the same person, because of how much we change. The same is true of our careers.
Mine started with a panic move — a professional singer and actor--what I always wanted to be as a kid, then suddenly a Customer Service Associate at a seed-stage startup. That one panicked, reactive decision launched a career in operations leadership in tech.
Now my pivots are intentional. Today I wrapped a call with a VP of Talent Development at a Series E, newly acquired, multi-billion dollar company. We talked about his transition from CEO → Product → People, and my own — very deliberate — as I explore my next chapter.
But years ago, I told my CEO I was burning out after years of leading operations — work I deeply loved. In the middle of another sprint of major growth ahead of a merge, he asked me to make a call: step up into an even broader role, or find another path. Either way, he'd support me, but I had to choose.
External recruiters had impressive roles on the table. Internally, there was a strategic product path. But I was panicked, and frankly, I didn't want any of it.
My friends, partner, and therapist were supportive, but none of them could help me think through an actual decision. Everyone had a personal stake in my choice, or just didn't understand the startup world. Also, I wasn't asking myself the right questions: What do I want? Who do I want to become? What kind of work actually excites me?
So I made a decision from exhaustion and burnout. I moved into product. I learned a lot — but it wasn't the right fit.
In retrospect, I never wanted to leave operations at all. I just needed mental space. I wanted to leave the burnout, develop other parts of myself professionally, and let go of the parts I'd outgrown.
I eventually left. And this time, I made deliberate choices — a new line of business in a completely new domain, then co-founding a startup, then building my coaching and consulting practice. And now, again.
You will always be busy. You probably already know you need a change. The hard part — and the more empowering, authentic, and sustainable path — is getting intentional about it.
Hi, I’m Sarah Caliendo! I’m an ICF-credentialed executive and career coach and operational consultant with 20 years of experience working with senior leaders in tech and fast-moving companies. I help leaders navigate career transitions, pivots, and organizational growth — with a people-first approach. I’m based in The Bay Area/Silicon Valley, but I work with clients globally.