My Tesla FSD Experience as an Insurance Agency Owner & Claims Exec
My Honest (and Slightly Life‑Changing) Tesla Experience: An Insurance Guy’s Take
4 min read
Chris Bakes
:
March 11, 2026
Last weekend I was cruising from Chicago to Eastern Kentucky in my Tesla in full self‑driving mode to watch my boys play baseball. The car was doing its thing while I was doing mine… Teams calls, ESPN Chicago, eating a Filet O Fish because Lent is Lent, thinking through work ideas and basically doing everything except watching the road. I know, I know. But here we are.
Somewhere in that mix the ESPN announcer reminded everyone to change their clocks for daylight savings. Then he added that most devices automatically update themselves now. That part stuck with me. Not the time change… but the idea that something we used to do manually has quietly become unnecessary. And for the record, I’m fully Team Daylight Savings. Just pick a time and stick with it. I don’t need my sleep schedule thrown into chaos twice a year like I’m training for a NASA mission.
And that sent me down a rabbit hole thinking about how much tech has changed in my 45 years… and how much faster it’s accelerating.
I still remember when my parents brought home our first microwave. I looked at it like it was a miracle.
“So we can heat food without the oven or stove?”
Mind blown.
If you wanted to hang out with your friends, you called their house on the wall phone or you walked over and hoped they answered the door. That was it.
The 90s had their own vibe.
Blockbuster on Friday nights.
TGIF with commercials you actually had to sit through.
Recording songs onto a mix tape with surgical precision.
And the massive 50‑disc CD changer stereo that doubled as furniture. Back then I honestly thought technology had peaked.
I got my first Blackberry pager and instantly felt like a high‑powered executive. I could read one line of an email and check my calendar, and I genuinely walked around like I was running national intelligence. If you had a Blackberry back then, you know the feeling. You weren’t just checking messages. You were “mission critical.”
When I turned 21, the only place you could legally gamble was Vegas. You had to actually get on a plane, walk through a casino that smelled like cigarettes and broken dreams, and hope your buddies didn’t convince you to double down at 3 a.m.
Now I can wake up at 6 a.m. and bet on Korean baseball while drinking pre‑workout. I can build a 20‑team parlay from my couch in 12 seconds and lose it in 13 seconds. Don’t judge me.
And online shopping… back then you had to physically go to the store, talk to a human and hope they had what you needed. Now my porch sees more foot traffic than a mall during the holidays. Some days I’ll open the door and there are so many Amazon boxes stacked up I wonder if a second family moved in. I love my wife and kids, but there are definitely moments I wish online shopping had never been invented.
Back then; we thought we were living in the future because we had Caller ID and Internet.
I had no idea what was coming.
Now my daily routine feels like something out of the future.
I wake up to a smart alarm that simulates sunrise.
I check my sleep and recovery data from my Galaxy Ring.
My workouts sync to the cloud to tell me whether I’m rested, stressed or ready to push harder.
I listen to audiobook chapters through wireless earbuds.
I commute in full self‑driving mode and talk into my Plaud AI device to drop reminders, tasks and content ideas.
When I get to the office, my AI agent has already prioritized my day. It logs into LinkedIn for my 5‑5‑5, pulls up overdue tasks, drafts messages in my tone and helps me clean up business responses.
Every meeting gets recorded and summarized. Action items are created automatically. Notes are logged in Microsoft Notes before I even close the call.
Throughout the day I use AI to handle the heavy technical tasks that used to eat up hours. It helps me polish RFPs for Sedgwick Auto so I can focus on strategy instead of formatting. It helps me build and optimize website content for Pro Insurance Group, whether that’s rewriting service pages, improving SEO or learning the backend structure that helps customers actually find us. Ten years ago I never imagined managing both an insurance agency and a major auto operation with this level of automation… and honestly, if you told 2006 me that AI would be helping me write insurance content, I would’ve laughed and gone back to thinking my Motorola Razr was the future.
When I have downtime I’ll ask Grok something simple like whether I really need the new hot and cold Theragun that promises to “unlock peak recovery,” or if I’m just bored and pretending I’m training for the Olympics. I’ll also ask if it’s a smart idea to buy whatever overpriced supplement influencers swear will turn me into Captain America or if I should add another unnecessary smart gadget to the house that I’ll use twice and then forget exists. And when I ask Grok what meal I can make with three random ingredients, it answers like I’m hosting a cooking show. “You can easily make a pan‑seared garlic lemon chicken with a reduction sauce.” No I can’t, Grok. I have mustard, shredded cheese and a protein bar. Please relax.
Things that felt impossible in the 80s, 90s or early 2000s are now just part of my Tuesday morning.
If technology has evolved this fast in my lifetime so far, what does the next stretch look like?
What kind of world will my kids grow up in?
What will my grandkids see?
Does work ethic matter if everything becomes automated?
Do we lose real communication?
Do we become a society where robots cook, clean, respond, drive and handle everything while people sit inside glued to screens and never leave their homes?
Some people might love that idea. Not me. That sounds like a prison.
I’m not rejecting technology. I use it more than most people. I embrace it. It makes me more efficient, gives me more time and helps me lead both Pro Insurance Group and Sedgwick in ways that simply weren’t possible twenty years ago.
But I’m not letting technology become my entire reality either.
I’m still going to the American Legion on Friday nights.
I’m still talking sports and hanging out with friends.
I’m still planning pool parties.
I’m still having real conversations with real people.
I’m still doing what’s best for my family, my friends, my employees and my company.
Technology should make our lives better, not smaller. It should support us, not replace us.
I hope my kids and eventually my grandkids grow up in a world where tech enhances their opportunities but doesn’t take away the things that matter. I want them to work hard. Build real relationships. Go outside. Talk to people. Learn. Fail. Grow. Be human.
That’s the future I want. And I think it’s still possible if we stay intentional.
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