Finding Strength in the First Lily Pad | FREEDOM DECODED Ep 49: A Podcast From Demir & Carey Bentley

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Time stamps:

00:00 - Intro

01:12 - Jill’s Search for Stability. Carey and Demir sit down with Jill, a 61-year-old widowed caregiver and contractor, who is balancing the heavy load of supporting her aging parents, guiding her adult son, and navigating unpredictable contract work. Together, they reframe the chaos of her many roles into one clear priority: stabilizing her income as the first step toward freedom.

14:02 - The Pull Between Purpose and Practicality. Jill wrestles with a crossroads: choosing between the steady path of contracting and the purposeful path of widow coaching.

17:35 - Networking Without Pitching. Carey introduces a powerful reframe that networking isn’t about selling yourself, it’s about genuine curiosity and relationship-building.

27:06 - De-Risking for Runway. Creating a stable income first provides the “runway” to test, pitch, and refine without the crushing pressure of immediate success.

30:14 - The Two-Hour Job Search Mindset. A streamlined, structured approach shows Jill how job hunting can become a focused two-hour weekly system instead of an all-consuming grind.

33:53 - From Connections, Not Clicks. Why organic validation through people and businesses beats early spending on ads.

34:42 - A Bills-Paying Job Stability starts with securing a role that covers the basics, creating space for bigger goals.

36:00 - Running Multiple Searches at Once to keep several paths alive in parallel without overwhelm.

37:00 - Imperfect Action Over Perfectionism. Demir stresses the mantra of massive imperfect action: take so much action that it would be unreasonable not to see results.

37:39 - Blowing Apart the “Ball of Crazy.” Breaking big, messy challenges into sequenced steps—one lily pad at a time.

40:00 - The Hidden Value of Strategic Roles. Some jobs offer priceless exposure to networks, systems, and opportunities—even if they’re not the highest paying.

41:02 - Three Criteria for the First Lily Pad Job: Financial stability, Time stability, and Leverage into future opportunities

43:36 - From Overwhelm to a Clearer Path. What began as tangled goals transforms into a linear, actionable process centered on stability and momentum.

44:10 - The Six-Month Test & Massive Imperfect Action.

44:46 - Process Over Outcomes & The Power of One System.

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