Reinventing Your Career (Again and Again) with Ilana Golan | 374

Dec 29, 2025

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If you grew up thinking adulthood meant “figure it out once and then coast,” this episode is your loving wake-up call. Reinvention isn’t a plot twist anymore — it is the plot. Careers shift, relationships change, industries get AI’d, and your dreams evolve faster than your LinkedIn headline.

In this conversation, I sit down with Ilana Golan — F-16 flight instructor turned tech exec turned founder & CEO of Leap Academy, a career reinvention platform that helps driven professionals leap into leadership, entrepreneurship, and portfolio careers.

We talk about what it actually takes to reinvent yourself (again and again), build a portfolio career that doesn’t burn you out, and turn your hardest seasons into rocket fuel instead of reasons to shrink.

Because staying stuck isn’t a personality trait. It’s a habit. And you’re allowed to outgrow it.

In This Episode, We Cover:

Reinvention as a life skill, not a crisis – why you’ll need to reinvent every 1–2 years in today’s world, and how to stop making that mean you did something wrong.
IQ, EQ, and now AQ (Adaptability Quotient) – the new metric that matters
Breadcrumbs & clues – how to spot your zone of genius in the patterns, feedback, and “random” skills you’ve picked up along the way.
From failure to fuel – how Ilana rebuilt after being kicked out of her own company, and how to move from spiral to experiment when life blows up.
The 5 days / 5 weeks / 5 months framework – a simple, non-scary way to test new directions without burning your life to the ground.
Portfolio careers 101 – what they are, why one job won’t meet all your needs, and how to add new income/impact streams without looking like a confused hot mess.
Stability and possibility – how to choose a “baseline” role or revenue stream so you feel safe enough to play, experiment, and leap.
Reinvention after rejection, grief, or trauma – why you can’t tell your story from the open wound, and how to move from bleeding to scar to superpower.

Because the moment you stop chasing the life you think you should want, you finally make space for the one that was meant for you all along.

Thank you to our sponsors!

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Connect with Ilana:

Website: https://www.ilanagolan.com

Leap Academy: https://www.leapacademy.com

IG: https://www.instagram.com/ilanagolanleap

LI: https://www.linkedin.com/in/ilanagolan/

Youtube: https://youtube.com/@ilanagolan-leap-academy

LeapCon (free gift and discount code): http://leapacademy.com/tiww (Code: TIWW)

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