Becoming UnDone, Episode 141
Ilana Golan: Turning Setbacks Into Success With Strategic Career Leaps
Host: Dr. Toby Brooks
Date: November 9, 2025

Episode Overview

This episode features Ilana Golan—Air Force veteran, tech executive, serial entrepreneur, and founder of Leap Academy—who shares her powerful journey of resilience after facing major professional setbacks, including being ousted from her own startup. Dr. Toby Brooks and Ilana discuss how high achievers can transform painful endings into new beginnings by embracing intentional, strategic career leaps, building portfolio careers, and redefining success through every phase of life.

Key Discussion Points & Insights

1. Ilana's First Major Leap: From Israeli Air Force to Tech Leader

• At age 18, Ilana became the first woman commander in an F16 pilot training squad, making life-and-death decisions far beyond her years ([08:48]).
  • Quote: “I got to be the first woman to become a commander in the squad... it gives you a lot of confidence, but also a lot of teaching moments.” —Ilana ([08:48])
• Early experience in breaking through barriers instilled resilience, grit, and the ability to act despite feeling unready—skills foundational to entrepreneurship and leadership ([09:53]).

2. The Ousting: Peak to Crash in a Day

• After a successful career in tech (Intel, startups, executive roles), Ilana co-founded a Silicon Valley startup with a long-time friend. They raised three times more than their goal, valued at $5 million ([12:23]).
• On the very day she celebrated with friends and family, her co-founder told her she was out. Suddenly: “No job, no startup, no investment, and my ego deeply crushed.” ([17:26])
  • Quote: “My identity, Toby, was always attached to my title... suddenly I was a nobody.” —Ilana ([17:26])
• The emotional fallout included shame, regret, and complete loss of direction ([18:31]).

3. Navigating the 'Purpose Storm'

• Ilana describes the aftermath as overwhelming, lost, and sleep-deprived, physically and mentally unwell ([19:49]).
• She tried to muscle through by overdoing: “throwing spaghetti on the wall,” but nothing was strategic or intentional.
• Regret was a necessary, galvanizing emotion—solidified during a personal cancer scare:
  • Quote: “I needed to feel that regret. That regret was something I never want to feel ever again.” —Ilana ([24:01])

4. Redirection Versus Failure

• Ilana reframes all failures as redirections, not endings:
  • Quote: "All the failures should be redirected... they’re teaching us something.” —Ilana ([25:23])
• Her setback led directly to the founding of Leap Academy, a business helping others leap successfully.
• Entrepreneurship is not always the answer for everyone—having intentionality and a personal strategy is more important than blindly chasing “success” ([25:23]).

5. Strategic Leaping & Portfolio Careers

• Ilana warns that today, staying in a single corporate path is riskier than ever—everyone should be “leap ready,” building personal brands and multiple streams of income ([31:31]).
  • 62% of top performers have more than three streams of income.
  • “Even if you’re staying [in your job], you always want to know what’s next.” —Ilana ([31:31])
• Importance of strategic, not reactive, choices—deliberately designing one’s next leap rather than just “throwing darts.”

6. Recognizing When to Leap

• Ilana emphasizes always being prepared to transition—even if you aren’t planning to leave yet ([31:31]).
• Key signs include misalignment with your values, desire for broader impact, or finding yourself on autopilot instead of being intentional about growth.
• High achievers should cultivate advisory, board, speaking, and mentorship opportunities as “insurance” for inevitable change ([31:31]).

7. Helping the Driven, Not the Unmotivated

• Leap Academy’s process isn’t for the complacent; it’s designed for high achievers who know they’re capable of more but need guidance and community ([36:09], [38:42]).
  • “They all know there’s more they can achieve... they don’t want to feel regret. They want to create something incredible.” —Ilana ([38:42])

8. Redefining Success in Life's Phases

• Success is not a static checklist; it evolves with life phases (financial goals, growth, impact, balance) ([42:17]).
• Quote: “No career will give you all of them…you can have all of them, just not at the same time.” —Ilana ([42:17])
• Allow yourself to focus on different ‘must-haves’ in different seasons—give yourself permission and grace to pivot, pause, or re-prioritize ([44:18]).

9. The Power of Community and Asking for Help

• High achievers often struggle to ask for help or admit vulnerability after big wins, but community is critical for rediscovery and next steps ([40:51], [41:21]).
• Finding peers in similar situations at Leap Academy was liberating for many, including Ilana herself.

10. Saying No & Working Smarter

• Success isn’t just working harder, but being intentional about what aligns with your purpose. If it doesn't "feed and fuel" your purpose, it's a distraction ([48:05]).
  • Prioritize what’s truly impactful and learn to say no.

Notable Quotes & Memorable Moments

• “I needed to feel that regret. That regret was something I never want to feel ever again.” —Ilana ([24:01])
• “All the failures should be redirected... they’re teaching us something.” —Ilana ([25:23])
• “Even within the same corporate role, you still want to create a bigger impression of yourself... you want to be leap ready to the next role.” —Ilana ([31:31])
• “They all know there’s more they can achieve in life, and they want to...they don’t want to feel that regret.” —Ilana ([38:42])
• “No career will give you all of them...You can have all of them, just not at the same time.” —Ilana ([42:17])
• “If it doesn’t feed and fuel my purpose, it’s a distraction.” —Toby ([48:05])

Timestamps for Key Segments

• Ilana’s Air Force story and first leap: [08:48]
• Being ousted from her startup: [12:23], [17:26]
• Navigating despair and rediscovering self: [18:31] – [21:11]
• Cancer scare and epiphany: [22:44] – [24:01]
• Reframing failure and the birth of Leap Academy: [25:23]
• Strategic approach to career changes: [27:54], [31:31]
• Building portfolio careers/multi-income streams: [31:31], [34:41]
• Patterns among high-achieving clients: [36:09], [38:42]
• Challenges with vulnerability & community: [40:51], [41:21]
• Redefining success and life’s phases: [42:17] – [46:02]
• Saying no and being intentional: [48:05]
• Ilana's future: the next leap (upcoming book, scaling Leap Academy): [50:08]

Lighthearted and Personal Moments

• Song for Ilana’s life montage: "Some Top Gun song, probably. … It opened possibilities I didn’t even realize." ([48:39])
• Host Toby’s support: “Consider me in because I am all in on Leap Academy.” ([52:48])
• Ilana’s parting humility: “Toby, you are an incredible interviewer … incredibly talented at what you do.” ([53:05])

Where to Find Ilana and Leap Academy

• Leap Academy: leapacademy.com
• LinkedIn/Instagram: Ilana is active and welcomes genuine connection ([53:30]).

Takeaways

• Setbacks hurt, but reframed intentionally, they provide the fuel for future impact.
• Be deliberate about your career and growth—prepare for the next leap before you truly need it.
• Remain open to reinvention; success can and should look different as you grow.
• Build a community; high achievers struggle alone, but thrive together.
• Define what matters to you in your current life phase and organize your goals accordingly.
• Above all: resiliency, reinvention, and leaping strategically are not just possible, but necessary in turbulent times.

Summary by Podcast Summarizer AI