My Career In Being The World's Biggest Troublemaker

Let's Be Honest with Kristin Cavallari

Dear Media

Society & Culture, Relationships

4.2 • 2.9K Ratings

🗓️ 2 September 2025

⏱️ 52 minutes

🔗️ Recording | iTunes | RSS

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Summary

In this episode, I’m reflecting on all the questionable life choices I got into growing up... starting as early as 4th grade when my diary got me in trouble, to running around Chicago when I was supposed to be in class, piercing myself, sneaking out, getting picked up by the cops, and yes… that one shoplifting incident that earned me 100 hours of community service. I share why my mom had to pull me out of 8th grade and how I basically made a career out of being a full-time troublemaker. Now that my own kids are in this era, I’m seeing it all from the other side, and realizing how my wild past made honesty the #1 thing in my house today.

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Transcript

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0:00.0	The following podcast is a dear media production.
0:04.4	This is Let's Be Honest with Kristen Cavalery, a podcast all about getting real and open on everything from sex, relationships, reality TV, wellness, family, and so much more.
0:15.4	And just a fair warning, there will probably be some oversharing.
0:21.5	I have a co-host. warning, there will probably be some oversharing. Because I got all the power, yep.
0:27.1	I have a co-host today if you're watching Teddy.
0:28.5	My doodle.
0:29.6	My little doodle.
0:30.9	He's my baby, man.
0:33.0	Oh, Teddy, you're almost two years old.
0:34.9	He is huge.
0:39.4	I had no idea how big he was going to get. He was a rescue, but he, I know.
0:46.7	Hi. He thinks he's still 10 pounds and he always just wants to be in my lap. But, oh, I love him.
0:53.9	I love my little teddy boy. But hi. Happy September. How is it already September? I don't understand.
0:55.3	I don't understand where this year went,
1:01.9	quite honestly. The fastest year of my life. What the heck? Okay, bye, Teddy. Teddy's leaving. It's crazy,
1:07.2	but I'm so happy that it's September. Fall is my favorite time of year, especially in Nashville.
1:13.0	Nashville is beautiful. If you guys get the chance to come to Nashville and you can pick when it is, come during the fall, September, October. Best months here. All the leaves are
1:19.3	just beautiful and it's not so crazy hot. So I'm really happy about that. Also, Camden and I have
1:25.5	been golfing a lot, a lot. Camden is obsessed with golf and so I've been
1:31.5	taking them and I grew up going to the driving range. I mean, I love to hop golf, you know,
1:36.3	but I've never actually played. But Camden and I first played over the summer. We played
1:40.8	nine holes. And I really, I was like, okay, I kind of get it now. I'm all in on golf. And so that's what we've been doing. Pretty much every weekend I've had the kids, Camden and I have golfed. I've taken all three of them, but the little two don't really necessarily like it that much. Camden's locked in on it. And so we golfed Sunday two days ago when you're listening to this. And now it's, it's so nice because
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