We continue our conversation by introducing you to the lesser-known but influential concept of sure loss. Sure loss explains why we often become risk-seeking precisely when we should stop, whether it’s because we’re holding on to a losing investment, staying in an unhealthy situation, or doubling down on a clearly failing strategy. When loss isn’t yet admitted but seemingly imminent, our brains work overtime to avoid making it feel more real, even if that means taking bigger and riskier bets. By using everyday examples of money, work, and relationships, we use this episode to reveal how the fear of sure loss can distort our judgment and why awareness is key to making smart decisions about when we persist, and when we walk away.

Chapter Markers:

0:00 – What “Sure Loss” Means

2:05 – The Coin Flip Example and Pain Avoidance

4:15 – Unrealized vs. Real Losses

5:00 – Why We Double Down Instead of Cutting Losses

8:10 – How Sure Loss Shows Up Beyond Money

9:00 – The Core Insight: When We Take Risks