Episode Summary: "Reinventing Your Career (Again and Again)"

Podcast: This Is Woman's Work with Nicole Kalil
Host: Nicole Kalil
Guest: Ilana Golan (Founder, Leap Academy)
Date: December 29, 2025
Episode: 374

Episode Overview

In this episode, Nicole Kalil invites Ilana Golan—tech entrepreneur, mountaineer, podcast host, and founder of Leap Academy—to unpack the complex, ever-present theme of career and life reinvention. Together, they challenge old paradigms around "woman’s work," offer actionable advice on navigating transitions, and celebrate the courage it takes to reinvent over and over again. With candor and humor, they reframe reinvention as not just an option, but the new norm.

Key Discussion Points & Insights

1. The Necessity and Normalcy of Reinvention

00:55–04:28

• Nicole reflects on her own expectation that adulthood is about "figuring it out once," only to discover the ongoing need for reinvention:

  "It turns out life isn't about figuring it out once. It's in reinventing yourself over and over again." (02:00)

• Ilana emphasizes that with the current pace of change, reinvention is not a rare event but a frequent necessity:

  "We do this all the time. In fact, at this pace of change, we're going to do it every year or two, so we better get really, really good at it." (04:30)

2. Finding Your 'Zone of Genius' by Following Breadcrumbs

04:28–09:02

• Ilana outlines how pivotal clues from past experiences—“breadcrumbs”—illuminate your true strengths and passions.
• Example: Ilana realized her strength was not just in technical skills, but in client interaction and connecting with people.

  "There's always like transferable skills. There's always a path. Success leaves clues. And if you can start looking for those clues, you actually are going to start understanding what is your zone of genius." (04:40)

• The importance of telling your story based on who you want to become, not just who you’ve been.

3. The Role of Experimentation and Curiosity

09:02–13:18

• Nicole and Ilana agree that many women feel pressure to be certain, which hinders experimentation and growth.
• Ilana introduces the concept of treating career moves like startup experiments:

  "In the world of startups, we experiment all the time... Why are we not doing this for careers? It's actually the same." (10:39)

• Key insight: Adaptability is now measured as AQ (Adaptability Quotient)—a crucial skill surpassing IQ and EQ in today’s workforce.

  "It is actually AQ... Adaptability quotient. With the pace of AI...reinventing, leaping is actually becoming the most important skill for the future of work." (11:54)

4. Reinvention After Setbacks, Failure, or Pain

13:18–18:37

• Nicole shares:

  "My biggest reinventions came out of some of my hardest, most challenging, most painful experiences." (13:41)

• Ilana recounts being ousted from her own company, highlighting the need for grace, healing, and eventually experimentation:

  "You can't really tell your story when the wound is really bleeding, but you can tell your story from the scars." (14:41) "Think about it as experimentation... It's not suffocating. All you need to decide is, is it worth five more weeks or do I want to switch to something else?" (16:20)

• The “5 days, 5 weeks, 5 months” framework for testing new directions.

5. Portfolio Careers: The New Model

22:48–28:09

• Ilana defines a portfolio career as a blend of stable income plus additive ventures that create "ripple effects."

  "One career is probably not enough if you want more from your life." (23:15)

• Stability (anchor income) allows risk-taking in other ventures.
• Most millionaires have 4+ income streams—a model Ilana encourages for fulfillment, impact, and resilience.

6. Actionable Steps to Reinvent & Advice for When You're Stuck

28:54–34:53

• When reinvention feels too daunting, Ilana recommends:
  • Identifying and focusing on your “must haves.”
  • Releasing the need to “have it all at once.”
  • Understanding it's the meaning, not the challenge itself, that holds you back:

    "It's never the challenges that stop us. It's always our belief around the challenges and the meaning that we're giving it." (29:46)

  • Surrounding yourself with others who “leap” and support your growth.

7. Reframing Reinvention as the Road, Not a Detour

31:27–34:53

• Nicole sums up:

  "Reinvention is no longer a detour. It's the road we're on." (32:04)

• Ilana normalizes reinvention within roles and organizations—not just via job changes, but shifts in function, responsibility, or approach.

Notable Quotes & Memorable Moments

• "We collect breadcrumbs along the way, experiences, wins and losses, joys and pain, success and failure. And those give us hints about who we're becoming and where we're headed next."
  —Nicole Khalil (03:10)

• "At some point people were starting to come to me, not for business-related stuff, but for asking me about their careers... Our ecosystem will already hint us about our zone of genius and we're just not attentive enough to see the clues."
  —Ilana Golan (08:00–08:56)

• "Adaptability, reinventing, leaping is actually becoming the most important skill for the future of work."
  —Ilana Golan (11:54)

• "You can't really tell your story when the wound is really bleeding, but you can tell your story from the scars."
  —Ilana Golan (14:41)

• "The hardest thing in a goal is to let go of what society expects from us...the hardest thing is the emotional part of it."
  —Ilana Golan (30:42)

• "Reinvention is the work of the brave. The people who refuse to see stay stuck, who collect the breadcrumbs of their lives and decide to make something bolder, truer, and worth reinventing for."
  —Nicole Khalil (36:34)

Timestamps for Key Segments

| Timestamp | Segment | |:-------------:|:------------------------------------------------| | 00:55–04:28 | Framing reinvention as an ongoing necessity | | 04:28–09:02 | Finding your zone of genius, telling a new story| | 09:02–13:18 | Embracing experimentation, AQ over IQ | | 13:18–18:37 | Moving forward from failure, 5/5/5 framework | | 22:48–28:09 | Building a portfolio career | | 28:54–34:53 | Advice for reinvention when feeling stuck | | 31:27–34:53 | Reinvention as the new normal | | 36:33–36:59 | Nicole’s closing reflection on courage & reinvention |

Resources and Where to Learn More

• Ilana Golan: alanagolan.com, leapacademy.com
  • Free assessment, training, and 15-minute strategy session offered via Leap Academy
• Connect with Ilana and Leap Academy via their respective websites and social media (links in show notes)

Tone and Style

The conversation is candid, empowering, and honest, mixing humor and hope with actionable strategy. Both Nicole and Ilana use personal examples to make reinvention less intimidating and more accessible, encouraging the audience to embrace change as both normal and exciting.

For new listeners:
This episode is a handbook for anyone feeling “stuck” or craving change. Expect inspiration, practical frameworks, and permission to rewrite your life’s script—however many times you need.