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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.

 

Person holding a miniature house model, representing homeowner insurance protection and property coverage.

3 min read

Common Myths About Homeowner Insurance in Illinois

Owning a home in Illinois comes with many unique risks, including the possibility of damage from yearly snowstorms and tornadoes. The last thing homeowners need is to worry about their insurance, how to manage their policies, or how to make sure...

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A split-era collage showing a Blockbuster store, VHS tapes, and a flip phone transitioning into a Tesla in self-driving mode, AI tools on a laptop, and modern smart rings.

4 min read

From Blockbuster Nights to AI Running My Day: The Evolution of Tech

The Evolution of Technology and What It Means for the Next 45 Years Last weekend I was cruising from Chicago to Eastern Kentucky in my Tesla in full...

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Alarm clock set for 4 am with a list of things to do for the day

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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Baseball field on opening day representing the connection between 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

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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