Why It’s Worth It | Ever notice how we remember every painful detail of running into the wind but quickly forget when it’s at our back? Here’s what’s fascinating: this isn’t just about exercise. We systematically overestimate the obstacles we face while underestimating the advantages that help us along. When volunteers did a mix of easy and hard exercises, everyone thought 70-75% were difficult, even though it was actually split 50-50. Katy Milkman explores this “headwinds-tailwinds asymmetry” through the remarkable story of Antarctic explorer Richard Byrd, whose tale of survival gets remembered for its hardships while his incredible advantages often go unmentioned.

Katy starts with Richard Byrd’s 1933 Antarctic expedition, where he spent seven months alone in temperatures below minus 70 degrees. His generator malfunctioned, filling his hut with carbon monoxide. He couldn’t cook food, struggled to communicate, and wrote farewell notes expecting to die. Three rescue attempts failed before his team finally reached him after 66 hours of travel. His book “Alone” became a classic tale of man versus nature, cementing his reputation as a heroic explorer battling impossible odds.

But historian Daniella McCahey reveals what often gets overlooked. Byrd came from the Virginia “aristocracy”, one of its most influential founding families. His brother was a governor and senator; his wife was an heiress. Close family friends included the Secretary of the Navy. He counted Henry Ford’s son and John Rockefeller Jr. among his supporters. The Navy promoted him to Admiral at 41, fifteen years before his peers. This gave him access to equipment, personnel, and legitimacy that opened doors everywhere. His expeditions used cutting-edge technology: wireless radio (barely 20 years old!) allowed him and his team to be the first explorers to use voice communications in the Antarctic. 

Tom Gilovich from Cornell explains this tendency to focus on headwinds over tailwinds. When cyclists face wind resistance, they fixate on it; when wind pushes them forward, they adapt quickly and forget. His research shows this pattern everywhere. First-born children insist that their parents were harder on them than on younger siblings. College athletes each believe their sport demands the most sacrifice. In lab studies, people consistently overestimate how many difficult tasks they completed versus easy ones.

The mechanism is simple: we must pay attention to obstacles to overcome them. Advantages work silently in the background, requiring no attention. When hikers walk the 211-mile trail between Yosemite and Mount Whitney, those going north-to-south and south-to-north both claim they hiked uphill more than 50% of the time. Logically impossible, but psychologically inevitable: uphill takes longer, demands more attention, burns into memory.

This asymmetry matters most for gratitude. We lose sight of what we should be thankful for, feeding resentment and entitlement instead of appreciation. Tom suggests zooming out to see the full picture, like viewing our lives from above. When we only zoom in on details, obstacles dominate our view. His advice: when asking “is this fair?” we naturally list ways we’ve been disadvantaged. Dig deeper for hidden advantages. Consider the opposite of what comes naturally.

Byrd’s story exemplifies this perfectly. His book focuses on darkness, cold, poisoning, and isolation. But without family connections, government support, free equipment, media coverage, and mechanical transportation, he never could have attempted the expedition. He faced real dangers and showed real courage. But remembering only the headwinds while forgetting the tailwinds distorts both history and our own self-understanding.

Background | In this episode, Katy Milkman hosts Tom Gilovich, whose research reveals how our tendency to focus on obstacles shapes our perceptions and decisions.

Key Takeaways:

• We systematically overcount obstacles: In mixed easy/hard tasks, people estimate 70-75% were difficult when it’s actually 50-50. We spend more time and attention on challenges, making them loom larger in memory.
• Advantages work invisibly: Headwinds demand attention to overcome; tailwinds operate silently in the background. Byrd’s connections and technology enabled his expedition, but they get forgotten next to his struggles.
• Everyone thinks they have it hardest: First-borns think parents were tougher on them, athletes believe their sport requires the most sacrifice, etc. We’re acutely aware of our own obstacles, blind to others’.
• Time distorts perception: Uphill hiking takes longer than downhill, so both directions of an in and out hike can feel “mostly uphill.”
• Gratitude requires deliberate effort: Our natural focus on obstacles feeds resentment and entitlement. Zoom out to see the full picture, and actively search for hidden advantages typically overlooked.
• Consider the opposite: When asking “is this fair?” we list our disadvantages automatically. Dig deeper for advantages. In reflective moods, we can access what we’re grateful for.
• Both struggles and supports matter: Byrd showed real courage facing real dangers. But remembering only hardships while forgetting enabling factors distorts reality, crucially limiting our self-understanding and gratitude. 

Source | Choiceology: Obstacle Illusions – Season 15, Episode 3 (April 21, 2025) 

About | Katy Milkman is a behavioral scientist, Wharton professor, national bestselling author, and host of Choiceology, a Charles Schwab original podcast that melds conversations about science, research, and human quirks to help us make better decisions and avoid costly mistakes. She also produces an insightful free newsletter, Milkman Delivers (sign up on her website!). Katy believes the key to changing ourselves for good lies in better understanding the internal obstacles that hold us back.