When Your Dream No Longer Fits- Looks Like Work, Season 3, Ep 2

Written By Chedva Ludmir
Natalie sitting on a swing at the beach, overlay text Looks Like Work season 3 episode 2, When Your Dream No Longer Fits

There’s a specific kind of ache that comes not from failure, but from success.

You set the goal. You crushed it. You got the title, the paycheck, the LinkedIn clout.
And then… you look around and realize:
This life you worked so hard for?
Doesn’t actually feel like you.

In this conversation with Natalie Rozenboim—former COO of Resonai and recovering overachiever—we talk about what happens when the dream you built doesn’t fit anymore. And how confusing (and lonely) that moment can be.

Together, we unpack:

  • Pandemic-era plot twists that made us question everything

  • The guilt of walking away from something that “should” make you happy

  • The difference between quitting and evolving

  • How generational perspectives (hi, Boomers) complicate it all

  • And why the sunk-cost fallacy is basically the corporate version of “but I already bought the dress”

This isn’t an episode about throwing it all away for a cottagecore life (though… tempting). It’s about making space for the truth that our desires evolve—and so must our definitions of success.

Natalie drops a question that hits like a lovingly aimed frying pan to the face:
👉 “Am I building the life I want to live, or do I feel trapped in this life? And what am I going to do about it?”

It’s brave. It’s inconvenient. It’s necessary.

So if you’ve been quietly Googling “career pivots at 37” or journaling your way through some unsettling clarity, you’re not alone. This one’s for you.

 

Am I building the life I want to live, or do I feel trapped in this life? And what am I going to do about it?

 

Resources & Mentions:

Chedva Ludmir
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Creating Safe Places - Looks Like Work, Season 3, Ep 3
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The Questions We Don’t Dare to Ask- Looks Like Work, Season 3, Ep 1