This week on Shimmy Says, Alan Shimel gets personal and reflects on the importance of perspective in leadership. He begins with the Pittsburgh Steelers and the news that longtime head coach Mike Tomlin stepped down after 19 seasons. Not fired. Not forced out. He chose to step away, closing the chapter on one of the most consistent coaching tenures in modern sports.

From there, the conversation widens. The way fans react to winning without championships starts to look a lot like how leaders talk about technology today. We live in an era of extraordinary innovation, yet executive conversations are often dominated by frustration. AI is dismissed because it’s “only as good as human-written code.” Cybersecurity is labeled as “never finished.” Digital transformation is criticized for taking too long.

Alan challenges that mindset by connecting sports fandom with leadership expectations in business and technology. He explores how entitlement creeps in when success becomes normal, why progress is often judged by snapshots instead of long-term arcs, and why leaders need to zoom out to truly understand what’s working.

If you’re feeling frustrated with where technology is right now, this episode offers a reset. The days are long. The years are short.

That’s what Shimmy Says.

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