Outgoing in high school: knew all 900 students
Oakley was so socially immersed in high school that he knew every student in a 900-person school — making his college withdrawal even more striking.
Snapshot · The Mel Robbins Podcast
Create a Happier Version of Yourself: Redirect Your Energy for Positive Thinking
Explore episode
Jul 2, 2026
Where this was said
Oakley's Story, Part 1: High School Highs and Why He Didn't Want to Leave
At 10:23 · chapter starts 8:47
Oakley's backstory is more nuanced than a simple 'loved high school' narrative. He hated school through middle and elementary school, had few friends, and struggled academically — so when high school became a genuinely transformative experience, the attachment ran unusually deep. He was team captain of two sports, knew all 900 students across multiple grades, mentored freshmen, and volunteered in the community. By the time college decisions arrived, he was already so invested in his current life that he couldn't get excited about any of the options ahead of him. He arrived on campus on a rainy move-in day, tried to hype himself up with received wisdom that 'college is the best four years of your life,' and immediately felt nothing but dread.
Oakley's High School Bliss and College Crash
Oakley hated school until high school changed everything — he became a team captain, a mentor, a community volunteer. Then college arrived and he wanted none of it. The higher your previous peak, the steeper the drop feels — and the more likely you are to compare everything that follows unfavorably to it.
Takeaway 1: You Can't Open a New Door If You're Gripping the Old One
Comparison to the past doesn't just make you sad — it makes you judgmental, isolates you, and inflates a fantasy version of what you left behind. Oakley spent 18 months deciding his college friends couldn't measure up before he'd even given them a chance. The first fix: stop using your past as a measuring stick for your present.
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