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Friday Fail Forward - The To-Do List Trap

Friday Fail Forward - The To-Do List Trap

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About this listen

Ever feel like a productivity failure because you can't get through your daily to-do list? You're not broken - you're just human. In this episode, Heather breaks down the science behind why we're terrible at estimating time and shares practical strategies to stop the self-sabotage cycle.

What You'll Learn
  • Why we overestimate what we can do in a day but underestimate what we can achieve in a year
  • The "planning fallacy" and how it's sabotaging your productivity
  • How to audit your persistent tasks: delegate, schedule, or delete
  • The 3-3-3 rule for realistic daily planning
  • How to stop negative self-talk about productivity

Chapters:
  • 00:07 - Introduction to Fail Forward Friday
  • 00:58 - The To Do List Trap
  • 05:27 - Reassessing Your Daily Tasks
  • 08:43 - The Importance of Small Wins
  • 10:55 - Embracing Productivity and Self-Kindness

Key Takeaways

The Planning Fallacy: We consistently underestimate task completion time by 25-50%, even with previous experience of similar tasks taking longer.

The Compound Effect: Small, consistent actions over time create massive results, but we can't see it day-to-day.

The 3-3-3 Rule: Each day, pick 3 important tasks, 3 admin tasks, and 3 small wins to celebrate.

Your Friday Challenge

Look at your current to-do list and pick the 3 things that have been there the longest. For each one, make a decision:

  • Delegate it - Can someone else do this?
  • Schedule it properly - Give it realistic time allocation
  • Delete it entirely - Does this actually need doing?

Practical Tools Mentioned
  • The Sunday Audit: Weekly review of your ongoing to-do list
  • The Delegation Detector: If it's been on your list for more than a month, it needs action
  • The Compound Tracker: Keep a weekly wins list to see your actual progress

Quote of the Episode

"Productivity isn't about doing more things. It's about doing the right things. And sometimes the rightest thing is to stop beating yourself up for being human."

Resources Referenced
  • Daniel Kahneman and Amos Tversky's research on the planning fallacy
  • The compound effect of small consistent actions

Connect with Heather
  • Website: www.choosinghappypodcast.com
  • LinkedIn: https://www.linkedin.com/in/heatherbond/
  • Instagram: https://www.instagram.com/hvmasters/

About the Choosing Happy Podcast

The Choosing Happy Podcast is for transformational practitioners - coaches, consultants, NLP practitioners, hypnotherapists, and energy workers - who are ready for uncomfortable truths and real transformation. New episodes drop three times a week: Monday myth-busting, Wednesday real wins, and Friday fail forward sessions.

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Available on: Spotify, Apple Podcasts, Google Podcasts, and all major podcast platforms.

Episode Length: 12-15 minutes

Release Date: 15 August 2025

Tags: Productivity, Time Management, Personal Development, Coaching, NLP, Self-Compassion, Planning Fallacy

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Companies mentioned in this episode:

  • Daniel Kaneman
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