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Thoughts & Perspectives from Chris Bakes

Real‑world stories, personal commentary, and everyday insights on business, family, sports, tech, and whatever else deserves a good conversation.

 

These are the stories I’d tell you over coffee — business lessons, family moments, real-world insurance insights, and the occasional obsession with Teslas, baseball, or whatever else grabs my brain at 4 AM.

 

Personal Story

Chris Bakes and his sons Brayden and Ryan during the 2026 Illinois State Redbirds baseball season.

5 min read

Baseball, Business, and Fatherhood: The Long Game Continues

The end of a baseball season is never easy. No matter how it ends, you always find yourself looking back. The wins, the losses, the stretches where...

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Chris Bakes's daughter at her Huntley High School graduation, the image behind his Executive Insights essay on watching her grow up.Chris Bakes's daughter at her Huntley High School graduation, the image behind his Executive Insights essay on watching her grow up.

2 min read

The Blink of an Eye: Watching My Daughter Graduate

I always heard people say, “It goes fast.” I believed them. Kind of. But not really. This past Saturday, sitting inside Northern Illinois University...

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Alarm clock set to 4 AM, the image behind Chris Bakes's Executive Insights essay on rebuilding routine and discipline.

3 min read

The 4 AM Reset: How I Took My Life and Routine Back

Around September of 2025, I hit a wall. Not the dramatic movie-type wall where you sell everything and move somewhere quiet. This was the slow creep....

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Chris Bakes's twin sons in their high school baseball uniforms, the image behind his Executive Insights essay on baseball, business, and fatherhood.

4 min read

Baseball, Business, and Fatherhood: The Long Game

Friday, February 13th is opening day for my twins, and it’ll be the first time I get to watch them take the field together in a college uniform....

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2026 Tesla Model S in Pro Insurance Group's review of Tesla FSD by insurance agency owner Chris Bakes

3 min read

My Tesla FSD Experience as an Insurance Agency Owner & Claims Exec

My Honest (and Slightly Life‑Changing) Tesla Experience: An Insurance Guy’s Take

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