Career Coach | Speaker | CEO | Certified Rule-Questioner

I took the “right” path. But then I questioned everything

I started my career the way a lot of high achievers do, following the most prestigious door that opened. On paper it looked like a very intentional climb. In reality, I was figuring it out as I went, and quietly wondering why so much of it felt wrong.

I wasn’t bad at any of my past roles. I was actually pretty good at most it. But there’s a particular kind of exhaustion that comes from being competent at something that doesn’t fit. Where you’re performing well, but feel like you are in fact performing. I kept waiting for it to click or change. It didn’t.

What changed everything was learning to ask a different question. Not “what am I supposed to do next?” but “what do I actually want and why?”

That sounds simple, but it wasn’t. It took a decade of internal torment, a master’s degree in organizational psychology, and more than a few uncomfortable conversations to get me there.

But once I started asking that question, everything shifted.

Five Careers. Fifteen Years. Zero Regrets

Each move taught me something about organizations, leadership, and the gap between what companies say they value and how they actually operate. That accumulated knowledge is what I bring to every coaching session and every stage I step onto. It’s not theory. It’s pattern recognition built from living it.

Finance

Lehman Brothers

Consulting

Bain & Company

Hospitality

Starwood Hotels

Tech Startups

Various stages

Founder & CEO

Reworkit

The quick highlights

MA, Social-Organizational Psychology, Columbia University (Teachers College)

15+ years across finance, consulting, hospitality & startup tech environments

Certified Professional Co-Active Coach (CPCC), Co-Active Institute

Led teams from 2 to 100+ employees, including salaried and hourly staff

 What makes me different

I grew up in a multiracial and interfaith household, which meant I spent my whole life learning to hold multiple perspectives at once. That’s not a soft skill. It’s the foundation of everything I do.

I’m not here to tell you what to do. My job is to help you get clear enough on what you want that you can figure it out yourself. I ask good questions. I notice patterns you can’t see because you are too close. And I have a tendency to say the thing everyone in the room is thinking, but nobody has said yet. Clients tell me that I’m like the friend who will actually be straight with you, but make you feel good about it.

What people are saying…

  • “I feel like a different person! Overall, I feel so much more [equipped] to handle situations that come up at work (and in life)! I feel less chaotic and more in control of what options are available to me.”

    — Joy C., Director of Operations

  • “Jess was able to help me realize my value as well as my potential. Through thorough assessments, conversations and gentle nudging I feel more confident in the value I offer and how to actualize reaching my potential.”

    — Teaira P., Human Resources Leader

Me today

After all those years of trying to figure out what “success” meant to me, I finally landed exactly where I need to be. I love running my business, Reworkit, I love working with my clients, and I fully enjoy my life outside of work. I currently reside in Brooklyn with my daughter and partner. In the little free time I carve out as a working mom, I love to watch Bravo tv shows (I’m a big Housewives fan and frequently incorporate into my work) and building my Lego collection (because why should kids be the only ones who get to play?).

Want to work together?

Looking for coaching or corporate workshops?

Visit Reworkit

Want Jess to speak at your next event?

See speaking info