When Failure Isn’t an Option: A Chicago Woman’s Story of Grit & Survival episode artwork

EPISODE · Mar 12, 2026 · 28 MIN

When Failure Isn’t an Option: A Chicago Woman’s Story of Grit & Survival

from Chicago Real Estate Insider with Amanda McMillan · host Amanda McMillan

Chicago women in business face challenges few people talk about. In this episode, I sit down with Kim Blackburn, owner of Red June Cafe, to talk about grit, survival, entrepreneurship, motherhood, and why failure was never an option.From growing up on a farm and learning hard work early, to becoming a single mom, building a successful small business, surviving cancer, and navigating over 15 years as a woman business owner in the city—this is an honest conversation about what it really takes.In this first episode of SheCago Stories, we discuss:The realities of running a small business in Chicago* Why “work-life balance” often feels impossible for working women* How adversity can either break you—or force you to level up* The pressure women feel to succeed without showing struggle* The power of community, resilience, and self-trust* What Kim wishes she knew earlier about money, confidence, and riskThis episode is for the Chicago working woman who is building a career, raising a family, running a business, or simply trying to hold it all together—while wondering if she’s doing enough.If you’ve ever felt like quitting wasn’t an option—but exhaustion was real—this conversation will remind you that you’re not alone.🎧 Watch or listen to the full episode for a raw, meaningful discussion about women in business, entrepreneurship, motherhood, failure, and survival in Chicago.

Episode metadata supplied by the publisher feed · Published Mar 12, 2026

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When Failure Isn’t an Option: A Chicago Woman’s Story of Grit & Survival

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