Choiceology with Katy Milkman

Episode: "Why Starting Over Hurts"
Date: September 22, 2025
Host: Dr. Katy Milkman
Podcast by: Charles Schwab

Episode Overview

In "Why Starting Over Hurts," Katy Milkman explores a powerful but often invisible bias: our aversion to retracing our steps or starting over, even when it's clearly the best path forward. Using stories from history and new behavioral science research, the episode investigates why we resist abandoning sunk effort and doubling back, and how this affects the decisions we make—from as grand as building the Panama Canal, to as mundane as reassembling furniture.

Key Discussion Points and Insights

Everyday Examples of "Doubling Back Aversion"

00:08 – 02:02

• Listeners share relatable stories:

  • Furniture Assembler describes assembling a bed frame incorrectly but resisting the urge to take it apart and start over, only to waste more time struggling with mismatched pieces.
  • Cyclist recounts stubbornly insisting on a bad bike route during a trip, unwilling to backtrack even when it became clear the path was worse.

• Katy Milkman: Summarizes, "No one wants to backtrack. Even when it's the best option. It makes us feel like our past effort has been wasted." (02:02)

The High Stakes of Refusing to Start Over: The Panama Canal

03:05 – 17:00

• Historical Case Study:

  • The French attempt to build the Panama Canal, led by Ferdinand de Lesseps, failed in part due to an unwillingness to abandon the original (sea-level) plan, even when evidence mounted that a lock-based canal would be more feasible.

• Clifford Theiss (Professor of Economics):

  • Details the immense ambition and challenges of the canal project.
  • Highlights the environmental and geologic difficulties that made a sea-level canal nearly impossible.

• Daniel Dimatos (Financial Historian):

  • Describes Lesseps’ refusal to listen to engineers’ warnings and stick with a plan resembling his previous success (the Suez Canal).
  • Quotes:
    • "Lesseps, even at the end of 1886, is not convinced that a sea level canal cannot be built." (14:20)
    • "He had spent years convincing investors to invest in his company on the basis of a sea-level canal project." (15:41)

• Outcome:

  • The French effort fails: bankruptcies, lost lives, and an eventual American takeover, which succeeds only after switching to a lock canal design.

Behavioral Science: Research on Doubling Back Aversion

18:00 – 34:50

What is Doubling Back Aversion?

• Definition:
  • “A reluctance to pursue more efficient means to a goal when doing so requires undoing progress you’ve already made.” (Narrator, 18:00)
• Katy Milkman introduces: Professor Clayton Kricher, co-author of research on the topic.

Everyday Examples

• Clayton Kricher:

  • Shares personal examples—walking the wrong way out of his building and refusing to double back, and refusing to accept a more efficient flight route because it would require returning to his origin.
    • "The idea of retracing those steps...seemed crazy, and I didn't do it. But...if that stopover were somewhere else...I would have happily done that to shave a few hours off..." (20:16)

• Katy Milkman:

  • Connects this to work tasks like revising academic papers:
    • "It feels so painful to undo the work we’ve already completed." (21:42)

Experimental Evidence

• Kricher describes lab experiments using VR navigation:
  • Participants consistently chose longer, less efficient routes to avoid doubling back to their starting point, despite being aware it was less optimal.
  • "People are about 25 or 30 percentage points less likely to want to actually double back...even though it was going to save them time in the end." (24:30)

Why Does This Happen?

• Waste Aversion:
  • People dislike feeling their prior effort was wasted, and experience discomfort when they must "undo" completed work, even if it's the most efficient path forward.
  • "Turning around, starting over, kind of makes you feel bad about the effort that you’ve already put in." (27:13)
  • Ironically, by trying to avoid feeling bad about waste, we waste more time and resources.

Comparison to Sunk Cost Fallacy and Escalation of Commitment

• This bias is distinct in that the goal is never abandoned, just the route to the goal:
  • "For us, the question is never whether you should abandon your goal altogether. ...The question is how exactly are you going to get there." (29:55)
• Even when initial choices aren’t “your fault,” the aversion persists.

Strategies for Overcoming Doubling Back Aversion

32:26 – 34:31

• Be Forward-Focused:
  • Redefine “waste” to include wasting more time/resources by not taking the more efficient route, even if it means undoing prior effort.
  • "We have to be better at accepting that the past may be fixed, but we have full potential to change how we live our lives in the future." (33:44)
• Self-awareness and Practice:
  • Recognize the aversion and intentionally choose efficiency over sunk effort attachment.

Notable Quotes & Memorable Moments

• "No one wants to backtrack. Even when it’s the best option.” — Dr. Katy Milkman (02:02)
• "Lesseps, even at the end of 1886, is not convinced that a sea level canal cannot be built." — Daniel Dimatos (14:20)
• “Turning around, starting over kind of makes you feel bad about the effort that you’ve already put in. ...the irony is...you're going to actually waste more time in the future by taking those longer, inefficient routes.”— Clayton Kricher (27:13)
• “For us, the question is never whether you should abandon your goal altogether. …It’s more about what’s the right means…” — Clayton Kricher (29:55)
• “We have to be better at accepting that the past may be fixed, but we have full potential to change how we live our lives in the future.” — Clayton Kricher (33:44)
• “Once you recognize doubling back aversion, you can approach these moments with the awareness that going backwards is often the best way forward.” — Dr. Katy Milkman (36:33)

Timestamps for Key Segments

• 00:08–02:02: Listener stories: Furniture assembly & bike trip
• 03:05–17:00: The French Panama Canal failure
• 18:00–21:21: Defining doubling back aversion; everyday examples
• 23:33–26:01: VR experiment shows reluctance to retrace steps
• 27:13–29:09: Why we avoid starting over; comparison to sunk cost fallacy
• 32:26–34:31: Strategies for overcoming this bias

Tone and Style

The episode blends engaging storytelling, relatable humor, and accessible science. Milkman’s tone is empathetic, curious, and supportive, encouraging listeners to reflect on their own experiences and decision-making patterns.

Conclusion

"Why Starting Over Hurts" reveals why we’re so resistant to abandoning work midstream—even when logic dictates it’s the best path. Whether assembling a bed, choosing travel routes, or constructing world-changing infrastructure, our reluctance to double back can cost us time, resources, and missed opportunities. But by identifying this bias and focusing on the future rather than irretrievable effort, we can make smarter, more flexible choices.

For further reading and resources, see Clayton Kricher and Christine Cho’s paper, "Doubling Back: A Reluctance to Make Progress by Undoing It,” linked in the show notes and at schwab.com/choiceology.