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June 27, 2025 8 mins

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What You’ll Hear

00:00-01:00 | Welcome & Context | A quick recap of the three-part journey so far and why today is all about decisive action.


01:00-03:30 | The Decision Matrix Framework | Score traditional employment vs. entrepreneurship on 5 dimensions—Financial Security, Personal Fulfillment, Lifestyle Compatibility, Risk Tolerance, and Market Viability.

03:30-05:30 | The Hybrid / Portfolio Approach | How consulting bridges, side-hustle strategies, and phased transitions de-risk your next move.

05:30-07:00 | Your 90-Day Action Plan | Day-by-day structure for Foundation → Active Pursuit → Evaluation & Adjustment.

08:00-08:30 | Reality-Check Pivot Signals | Red flags that tell you it’s time to tweak or change course—without labeling it failure.

08:30-9:00 | Long-Term Lens & Final Charge | Two- and five-year visioning, plus your homework to lock in momentum.

Decision Matrix Cheatsheet

Rate each path 1–10 on the five dimensions, add the totals, and let the numbers spark an honest conversation with yourself (and your advisory board). A simple table or spreadsheet works; perfection isn’t required—clarity is.

🚀 90-Day Action Plan Highlights

  1. Days 1-30 – Foundation
    • Finish your matrix, calculate runway, refresh LinkedIn/resumé, validate ideas, rally your personal board.
  2. Days 31-60 – Active Pursuit
    • Apply, pitch, network hard; build an MVP if leaning entrepreneurial; stack certifications.
  3. Days 61-90 – Evaluate & Adjust
    • Double-down on wins, pivot from dead ends, weigh job offers, or set launch milestones.

⚠️ Pivot Triggers

  • Job Search: <60-day silence → widen geography, add contract roles, explore adjacent fields.
  • Startup: Crickets from target customers → refine offer, reposition, or rethink model.
  • Universal: Shrinking runway, family shifts, or unexpected opportunities → recalibrate.

📝 Your Homework

  1. Complete the matrix—today.
  2. Draft and calendar your 90-day plan.
  3. Share both with your advisory board for accountability.

If this series sparked clarity, pay it forward!
Rate & review on Apple Podcasts ⭐⭐⭐⭐⭐ and share this episode with a friend navigating their own crossroads. Your future self (and ours) will thank you.

Ready? The next chapter of your career isn’t going to write itself—go claim it.

https://midlifekicker.buzzsprout.com
On Spotify, Apple and wherever you get your podcasts.

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