In this episode of UH-OH Conversations with Cohesive Leaders, Ben-Jamin Toy chats with Jake Isaacs, a serial integrator, fixer, and behind-the-scenes operator who has made a career out of turning chaos into order.
Jake shares his unlikely start working for the Chicago Bears as a teenager, his journey through hospitality, tech, and nonprofit leadership, and why he proudly embraces the role of “number two” in business. But the heart of this episode is Jake’s candid story of a career-defining UH-OH: a careless text message that nearly derailed his trajectory as a young hotel manager.
Listen as Jake unpacks the fallout, how he rebuilt trust, and the leadership lessons he carries into his work today. From the importance of firing fast to the value of showing up even when it’s uncomfortable, this episode is full of wisdom for anyone who wants to grow as a leader without pretending to be perfect.
Failure isn’t fatal. It’s just your first attempt in learning.
Check this out: https://www.thecohesiveleader.com/Community
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