When Your Old Ways Stop Working | FREEDOM DECODED Ep 54: A Podcast From Demir & Carey Bentley
Mon Jan 26 2026
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Time stamps:
01:49 - Flying the Plane While You’re Still Building It
04:58 - The Advantage of a Clean Slate (Building vs. Resetting)
05:52 - The Importance of Specific KPIs in Ambiguous Roles
06:59 - Creating a “Headline” for Your Year
07:18 - You Only Have One Priority: The New Job
07:48 - Transition as Opportunity, Not a Problem for the Old Team
08:39 - Don’t Make a "Mona Lisa" Out of the Transition
10:08 - Time-Boxing Support to Avoid Becoming the Permanent Middleman
11:00 - Expectations Management as a Leadership Tool
12:00 - The Risk of Overlong Transitions
13:00 - Stress-Testing the “Best Case” Plan
14:15 - Comfort Bias Toward the Old Role
15:30 - Delegation as a Development Opportunity for Others
16:45 - Redesigning the Transition Model
17:05 - Best Case vs. Worst Case Thinking in High-Stakes Moves
18:15 - The Perfectionism Trap in Leadership Transitions
21:00 - Shifting from Execution to Strategic Visibility
22:30 - Health as a Non-Negotiable Constraint
22:55 - Stress-Testing Assumptions vs. Being Negative
25:00 - Gradual Boundary Enforcement Over Abrupt Pushback
28:30 - Professional Liabilities: When Overthinking Stalls Progress
30:00 - Transition Clarity Prevents Emotional Damage
37:07 - Creating a "Breadcrumb Trail" of Accountability for Your Team
41:15 - Putting Order to Chaos: Leveraging Process Skills
43:47 - Clarity as the Definitive Attribute of Great Leaders
44:45 - Using AI as a Thought Partner for Leadership
46:05 - Translating Strategy into Living Documents and Processes
51:34 - Relieving Managerial Pressure Through Ownership
52:40 - AI as a Brain Accelerator, Not a Miracle
53:44 - Becoming the Leader Who Sees the "One Key Thing"
Check out our FREE masterclass all about How To Plan The Perfect Week In 30 Minutes Flat: https://bit.ly/3eEZ9AQ
Check out our website: https://lifehackmethod.com/
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Grab a copy of our BOOK here: http://winningtheweek.com/ Join Lifehack Tribe: https://members.lifehackmethod.com/join-lifehack-tribe SUBSCRIBE to our podcast on the platform of your choice! Spotify: http://spoti.fi/3pNtPVe Apple Podcasts: http://apple.co/3tiIpWW Or subscribe to our YouTube channel: https://www.youtube.com/c/LifehackBootcamp Time stamps: 01:49 - Flying the Plane While You’re Still Building It 04:58 - The Advantage of a Clean Slate (Building vs. Resetting) 05:52 - The Importance of Specific KPIs in Ambiguous Roles 06:59 - Creating a “Headline” for Your Year 07:18 - You Only Have One Priority: The New Job 07:48 - Transition as Opportunity, Not a Problem for the Old Team 08:39 - Don’t Make a "Mona Lisa" Out of the Transition 10:08 - Time-Boxing Support to Avoid Becoming the Permanent Middleman 11:00 - Expectations Management as a Leadership Tool 12:00 - The Risk of Overlong Transitions 13:00 - Stress-Testing the “Best Case” Plan 14:15 - Comfort Bias Toward the Old Role 15:30 - Delegation as a Development Opportunity for Others 16:45 - Redesigning the Transition Model 17:05 - Best Case vs. Worst Case Thinking in High-Stakes Moves 18:15 - The Perfectionism Trap in Leadership Transitions 21:00 - Shifting from Execution to Strategic Visibility 22:30 - Health as a Non-Negotiable Constraint 22:55 - Stress-Testing Assumptions vs. Being Negative 25:00 - Gradual Boundary Enforcement Over Abrupt Pushback 28:30 - Professional Liabilities: When Overthinking Stalls Progress 30:00 - Transition Clarity Prevents Emotional Damage 37:07 - Creating a "Breadcrumb Trail" of Accountability for Your Team 41:15 - Putting Order to Chaos: Leveraging Process Skills 43:47 - Clarity as the Definitive Attribute of Great Leaders 44:45 - Using AI as a Thought Partner for Leadership 46:05 - Translating Strategy into Living Documents and Processes 51:34 - Relieving Managerial Pressure Through Ownership 52:40 - AI as a Brain Accelerator, Not a Miracle 53:44 - Becoming the Leader Who Sees the "One Key Thing" Check out our FREE masterclass all about How To Plan The Perfect Week In 30 Minutes Flat: https://bit.ly/3eEZ9AQ Check out our website: https://lifehackmethod.com/