Think Fast Talk Smart: Communication Techniques

226. Reinvent Yourself: Turning Uncertainty Into Opportunity

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Sep 2, 2025

In this enlightening discussion, Ilana Golan, founder of Leap Academy and host of the Leap Academy Podcast, shares her expertise on personal reinvention. She highlights the importance of being 'leap-ready' by asking three critical questions: Why me? Why this? And why now? Golan emphasizes honest communication as key to navigating life changes and encourages proactive assessment of personal fulfillment. Discover how to communicate confidently through transitions and embrace uncertainties as opportunities for growth!

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ANECDOTE

Career Built By Breaking Barriers

Ilana Golan described a career of barrier-breaking roles from corporate executive to F-16 flight instructor and founder of Leap Academy.
She attributes her path to persistence and a habit of pushing boundaries rather than innate talent.

INSIGHT

Always Be Leap Ready

Golan warns against 'sleepwalking' through life and urges continual intentionality about what's next in your career.
She says being 'leap ready' means always knowing where you're trying to go and building your personal brand toward it.

ADVICE

Listen For Wake-Up Signals

Scan for signals like burnout, waking at 3 a.m. with unease, or diminishing fulfillment as prompts to consider a pivot.
Use those feelings to intentionally decide what responsibilities or skills you want next rather than reacting impulsively.

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Reinventing your life or career starts with reflection and conversation.

Making the leap — to a new career, to the next stage of a relationship, or to a different version of yourself — requires honest communication. For Ilana Golan, being “leap-ready” requires that we answer three questions: Why me? Why this? And why now?

Golan knows all about these leaps, as her career spans corporate executive roles, entrepreneurship, and even F-16 flight instruction. As the founder of Leap Academy and host of the Leap Academy Podcast, she helps equip others to navigate their own personal and professional reinventions. As she says, “It’s really about communicating from the vision,” which starts as an inside job. “Why is this the right thing for me right now? You convince yourself first, because when you're [at] peace with what you're trying to do, it's a lot easier to convince others.”

In this episode of Think Fast, Talk Smart, Golan and host Matt Abrahams explore how honest communication shapes every stage of reinvention, whether that’s listening to the signals your mind and body are sending you — like “sleepwalking through life” and imagining something more — or articulating your pivot in ways that create understanding rather than resistance. Wherever you hope to leap, Golan’s insights show how to communicate through change with confidence and clarity.

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Chapters:

(00:00) - Introduction
(02:17) - Breaking Barriers & Career Patterns
(02:56) - Waking Up to Change
(04:20) - Signs It’s Time for a Pivot
(07:23) - The Rise of Portfolio Careers
(10:55) - Communicating Career Leaps
(14:07) - Finding Clarity in Reinvention
(19:36) - The Final Three Questions
(22:31) - Conclusion

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