The Interview

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A chance encounter between a quirky Minnesota transplant and a feather-dreaming Chicagoan unfolds into one of the most charmingly unconventional job interviews you'll ever witness. Seated in a bustling coffee shop, Debbie—self-described "brave chickadee" and certified judo master—meets potential employer Mr. Winjoe with a refreshing blend of nervousness and unfiltered honesty.

The conversation weaves through unexpected synchronicities (his recurring dreams about feathers meeting her bird-related self-descriptions), the cultural shock of navigating Chicago's "alphabet of trains," and Debbie's colorful backstory that includes training at "Rasmussen's Judo Center" after feeling like "an ugly duckling" in Minnesota. Her animated storytelling reveals both vulnerability and resilience, especially when casually mentioning her healthcare has consisted of "a halfway decent Dollar Tree first aid kit and a wing and a prayer" for years.

What transforms this meeting from merely amusing to deeply touching is the genuine connection forming between these strangers. When Mr. Winjoe offers Debbie not just a well-compensated position ($35/hour with benefits described as "a bushel of health insurance"), but also accommodations in his carriage house—effectively rescuing her from the downtown YMCA—her emotional response captures the profound impact of unexpected kindness. "I think I've died and gone to heaven," she exclaims, before pledging to be "the best gosh darn assistant" on either side of whatever geographical landmarks Chicago might have. 

Have you ever experienced a moment when someone took a chance on you, completely altering your life's trajectory? This conversation reminds us how authentic human connections can create opportunities more meaningful than any perfectly crafted résumé. Subscribe for more stories that celebrate the beautiful unpredictability of human connection.