Interrogating Your Calendar

In this episode of the Wholistic Productivity Podcast, Chris LeBrun sits down with executive productivity coach and bestselling author Demir Bentley to challenge one of the most dangerous productivity myths of our time: that success requires constant hustle, long hours, and personal sacrifice.

Demir shares his powerful personal story of burnout on Wall Street—and the moment a health crisis forced him to completely rethink how work, time, and success actually function. From that experience emerged the Winning the Week method, a practical framework designed to help high achievers reclaim their time, reduce overwhelm, and create sustainable momentum without burning out.

In this episode, you’ll learn:

• Why hustle culture often leads to burnout instead of results
• How to plan your week in a way that actually works in real life
• The difference between a wish list and a realistic plan
• Why putting personal priorities on your calendar first matters
• The four types of freedom that redefine true productivity

Show Links

http://winningtheweek.com 

https://www.instagram.com/lifehackmethod_/ 

https://www.linkedin.com/in/demirbentley/ 

https://www.youtube.com/c/LifehackBootcamp 

https://lifehackmethod.com/ 

Chapters

00:00 Introduction
02:41 Welcome Demir Bentley
04:02 Demir Bentley's Journey from Wall Street to Wellness
07:03 The Shift from Hustle Culture to Planning
10:15 Recognizing Rock Bottom and Embracing Change
14:08 The Digital Nomad Lifestyle
16:59 Understanding the Four Freedoms
18:55 The Winning the Week Method: Overcoming Resistance
21:51 Leveraging Priorities for Long-Term Success
22:49 Winning Your Week Method
30:06 Leveraging Time for Productivity
31:12 Interrogating Your Calendar
34:29 Understanding Time Supply and Liabilities
36:10 Calendarizing Your Tasks
41:19 The Importance of Accountability
45:40 AI: The Future of Productivity
51:43 Busting Myths About Productivity

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