Take a Jill Pill

This week, I'm talking about a bizarre Tennessee death row story that has left me with a million questions, including some I probably shouldn't be asking, but you know I'm gonna.

We're also talking about imposter syndrome, why even the most capable people sometimes feel like they have no idea what they're doing, and what to do when your own brain starts working against you.

Plus, another strange encounter at Trader Joe's (shocking, I know), my Top 5 sandwiches, and listener questions about being single in your 40s, finding your passion, and irrational pet peeves.

A little dark humor, a little self-reflection, and a lot of unnecessary thoughts. Take a Jill Pill.

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

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http://takeajillpill.com

This week we’re talking about how to tell someone they smell (spoiler: I have no idea), side hustles when everything costs too much, whether you should finally start that creative project, making friends as an adult, friendship disappointment, feeling trapped in your job, and how to enjoy conspiracy theories without spiraling into despair.

Basically, you sent in your problems and I did my best to solve them. Some I actually had advice for. Others left me completely stumped. But somewhere along the way, a theme emerged about change, figuring out what’s next, and learning to hold things a little more loosely when life doesn’t look quite like you thought it would.

Plus, I’m sharing my Top Five Guilty Pleasures, the worst advice I’ve ever received, and what happened when I asked ChatGPT to warn people about me. (I asked it to be meaner. That was a mistake.)

Some problems have answers. Some apparently just get a “Good luck with that!"

And yes, Take a Jill Pill hats are officially live! Get yours here!

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

After a few weeks away, I’m back and we have a LOT to catch up on. I’m talking about finally starting to record my new album, including the song that had me crying in the vocal booth, and sharing my memories of September 11th and my family’s personal connection to that day.

Then, naturally, things take a turn because apparently AI might kill us all in ten years. So why am I still answering emails?

Plus: Nashville, Dunkin’, the Lindsay Clancy mistrial, Costco, minor inconveniences that cause me major irritation, listener questions, and a Jill Pill about why I’m done waiting for life to “settle down” before doing the things I really want to do.

Cheers!

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

This week, I’m talking about faith, foot balm, and a whole lot of things I don’t know.

After watching the documentary, Death of The Pastor’s Wife, I found myself thinking about my own complicated relationship with church, organized religion, and faith. I grew up in church, my faith is still a huge part of my life, and I also have a lot of questions. I’m sharing some of the experiences that shaped the way I see it all now, why I think putting people on pedestals can get dangerous, and why maybe one of the most honest things we can say is simply, “I don’t know.”

But don’t worry, we’re also discussing the Robot Olympics, ChatGPT getting things very wrong, my concerning habit of buying things online when I should be sleeping, and why TikTok apparently knows I need foot balm before I do.

Plus, my Top 5 things that were better in the ’90s, listener questions, and a Jill Pill about making a little more room for uncertainty.

Faith, foot balm, AIM away messages. We cover a lot of ground here.

Glad you’re here!

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

I’ve got a lot to catch you up on this week, starting with an important update on whether UPS pilots actually exist. I’m also defending my millennial commitment to ankle socks, preparing myself for Trader Joe’s pumpkin season, and getting excited about football season as well.

Then we’re heading down a few of the current rabbit holes I can’t stop thinking about, including Hayden Panettiere, Anthony Fauci, the Lindsay Clancy trial, and one very strange coincidence that has me asking questions.

Plus, I’ve got a new Top 5: ways to win me over…then listener questions, an update on new music, and a Jill Pill I almost couldn’t come up with. This is because lately I’ve realized I might be numbing out a little bit, and maybe we don’t always have to turn that into something we need to fix immediately. Sometimes it’s okay to give yourself a minute before you’re ready to feel everything again. Just my two cents.

Glad you’re here!

Host: Jill Pickering

Follow me at:

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http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

Kate Rapier is finally on Take a Jill Pill, and we’re answering the question a lot of you have been asking: What happened with Jill and Kate?

After more than 20 years of friendship, music, touring, songwriting, podcasting, and basically growing up together, a lot has changed. In this episode, Kate and I look back at how we met, the beginning of Jill and Kate, our years in the music industry, some of our favorite (and funniest) memories, and why we ultimately decided to end Jill and Kate.

And yes, we talk about the harder stuff too. The friendship breakup. The five months we didn’t speak. Why I wasn’t at Kate’s wedding. And how two people who had been more like sisters than friends found their way back to each other and rebuilt a friendship that looks different, and healthier, today.

We also get into Kate’s life now, divorce, motherhood, life after music, old Jill and Kate songs, touring stories, conspiracy theories, Trader Joe’s snacks, unfortunate facial injuries, and plenty of things neither of us planned to talk about.

If you followed Jill and Kate, listened to Girls Just Pod to Have Fun, knew us from our years touring and singing with Kelly Clarkson, or have simply wondered what happened between us, this one is for you. Pull up a chair and a glass of wine, put on some comfy clothes…we have a lot to catch up on.

Host: Jill Pickering

Guest: Kate Rapier

https://www.instagram.com/katerapier

Follow me at:

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Find Jill and Kate/Girls Just Pod to Have Fun at:

https://open.spotify.com/artist/3nOFoJxsyWVGxnFQMqjeH0

https://podcasts.apple.com/us/podcast/girls-just-pod-to-have-fun/id1303203325

I found myself thinking this week, I really wish someone had told me that.

Actually...I wish someone had told me a lot of things.

Things like the fact that almost everyone is making it up as they go. That your intuition deserves way more credit than you give it. That not every battle is worth fighting. And that some of the biggest disappointments in your life eventually become stories you tell without even thinking twice.

So this week, I'm sharing 5 things nobody really tells you, but maybe they should.

Plus, we end up talking about awkward Zoom goodbyes, Bryan Kohberger, New England accents, grammar, music, and a few listener questions along the way.

I hope one of these lessons meets you where you are today. And if nothing else, I hope you leave this episode feeling a little less alone in figuring life out.

Because remember…we're all kind of making it up as we go.

Thanks for listening to Take a Jill Pill!

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

This episode is exactly what happens when my brain is left unsupervised.

We're talking about Jimothy the raccoon, a restaurant that only sells deviled eggs (yes, really), a pedicure that turned into a full-blown character assessment, and the stranger who decided to perform karaoke directly into my ear.

Along the way, we also get into what caring for my mom with dementia has taught me about human connection, why age-gap friendships matter more than we realize, and the uncomfortable question I asked AI that completely called me out on my BS.

Plus:
• My Top 5 TV shows of all time
• Listener questions (including Noah Kahan's "Poop Gate," Trader Joe's, Dunkin', and some fascinating brain science)
• This week's Jill Pill:

I’m glad you’re here!

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

You voted, and this one won by a landslide.

This week I'm taking you behind the scenes of my twenty-ish years in the music industry…from touring the country in a silver minivan and playing biker bars to touring arenas with Kelly Clarkson and other artists. I'm sharing what life on the road was really like, the parts nobody sees, how one unexpected opportunity changed everything, and why touring wasn't necessarily always as glamorous as I imagined.

Plus: Backstage celebrity encounters, my top 5 venues I've ever played (#1 might surprise you), listener questions, and enough stories that this had to become Part 1.

Whether you've always been curious about the music industry or just want to hear how I once ended up wearing a "Fresh Meat" hat at a butcher shop on stage, this one's for you.

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

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http://takeajillpill.com

This week on Take a Jill Pill, I'm back after a week off and catching you up on everything: the guy who climbed the Empire State Building to propose (and got arrested for it), my Dunkin summer haul, and why the algorithm knowing my grocery store guy is getting way too close for comfort.

We also get into the marketing strategy behind Trader Joe's cashiers (yes, it's real, no, it doesn't change how I feel about the hummus), a very current conspiracy theory about CERN shutting down, and a Fourth of July story I wasn't planning on telling but somehow did.

Then it's the Top 5 things I used to care about and genuinely don't anymore, plus your questions on Taylor and Travis's wedding, Trader Joe's marketing, why I don't love soccer, and my family history.

And of course, today's Jill Pill: a question about what you might be avoiding and whether it's really worse than what's on the other side of it.

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

Therapist, author, and friend Dr. Lee Long joins me for a conversation that has genuinely changed the way I think about relationships, conflict, anxiety, and even everyday frustrations.

We start with Trader Joe's, conspiracy theories, and why humans are wired to search for meaning. Then we get into the powerful question at the center of Dr. Lee's book, WAIT, Where Am I in This?

Why do we spend so much energy trying to change other people? Why do certain situations trigger such strong reactions in us? Why do we spiral over unanswered texts, feel stuck in the same relationship patterns, or find ourselves getting way too angry at strangers on the road?

Dr. Lee explains how one simple question can help us stop looking outward for answers and start understanding what's happening inside. We talk about self-awareness, people-pleasing, mind-reading, control, emotional triggers, and the difference between focusing on yourself and being selfish.

He even walks me through my own road rage in real time, which was both enlightening and slightly humbling.

If you've ever found yourself thinking, "If they would just change, everything would be better," this episode might give you a completely different perspective.

Because the most important question you're probably not asking yourself is:

Wait... where am I in this?

You can find Dr. Lee Long here:

Get his book on Amazon or Audible: WAIT, Where Am I in This?

Podcast: Wait, Let’s Talk About That

Website: http://www.drleelong.com

Instagram: @dr.leelong

Host: Jill Pickering

Guest: Dr. Lee Long

Follow me at:

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http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

Disclaimer: We talk about a lot of therapy-related topics in this episode, but this is a podcast conversation, not a therapy session. Dr. Lee Long is not my therapist, and nothing discussed here should be considered mental health treatment or individualized professional advice. If you're looking for support with your own situation, please connect with a licensed mental health professional.

This week, we're doing something just a little different. I have a lot of random thoughts and so you're getting a really long audio message from IDK your BFF Jill, and I hope you're going to be okay with that.

We're catching up on a few ongoing sagas (still no Nancy Guthrie, still no bear spray), I scored the Dunkin' Pineapple Cup, and then I just…start talking. About everything. The random thoughts that live rent-free in my brain, the questions I have that I don't actually need answered, and a few things I learned this week that genuinely rocked my world.

We've also got top 5 karaoke songs, listener questions, and a Jill Pill about the freedom of just saying no.

It's a bit of a random episode, and very much an audio message I might send to my friends. So, here goes nothing!

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

This week, I have some thoughts about the NXIVM cult. What started as a self-help and leadership program somehow turned into a secret society, branding ceremonies, and a lot of red flags. I’m talking about how ordinary, intelligent people can get pulled into groups like this, and why it's not always as obvious as you'd think.

Plus, I'm sharing my Top 5 true crime and real-life drama podcasts, including some absolute favorites that will completely consume your life. (Links to them are below)

I’m also answering some listener questions about:

• Managing anxiety
• The mystery of Malaysian Flight 370
• Which kitchen utensil I would be (important stuff)

And for this week's Jill Pill, a reminder to be careful what you normalize…because the things we accept over time have a way of shaping our lives.

Grab your coffee, watch out for bears, and let's get into it.

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

Links:

Read The Goodpasture Chronicles

Escaping NXIVUM podcast

This is Actually Happening podcast

To Live and Die in LA podcast

S-Town podcast

Something Was Wrong podcast

Betrayal podcast

This week we’re talking about: yard sale anxiety, a disastrous run of Chipotle mobile orders, Dunkin’ freebies, emotional overwhelm…and somehow it all makes sense. (I think?)

I'm doing my first listener chat with Meghan…loyal Dunkin’ lover & fellow New Englander, to talk about the cult-like world of Dunkin’ giveaways, then I get into the three emotions that may be quietly sucking the life out of you: guilt, worry, and chronic overwhelm.

Plus, my top five kitchen staples, listener questions, celebrity crushes, and a reminder that sometimes it's okay to stop trying so hard and just start fresh tomorrow.

Take a Jill Pill and come hang out.

Host: Jill Pickering

Guests: Meghan - Fellow Dunkin’ Fan!

Follow me at:

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http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

This week on Take a Jill Pill, we’re covering Gerald the dolphin and his underwater cities, government bird drones, talking animals, dirty sodas, Gracie Abrams, and why I may officially be becoming a Bird Lady.

The episode starts with summer arriving in New Hampshire and me getting territorial over my beach walks…and somehow ends with me questioning whether pigeons are spying on us. (Have you ever SEEN a baby pigeon??)

I also share my top 5 birds (yes, really), answer listener questions about social media, starseeds, and life’s surreal “wow” moments, and talk about why nature might be trying to tell us more than we realize. It’s fun, chaotic, a bit thoughtful, and definitely one of those episodes where we just keep following the rabbit trail wherever it goes.

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

This week on Take a Jill Pill, I survive a fire ant attack in Nashville, witness a chaotic e-bike accident at a preschool soccer practice, and officially declare that the ants are seeking revenge after I mocked them online. My feet may never recover.

We also get into my growing fear of cruise ships, why flying suddenly feels more stressful than it used to, and the emotional devastation of Southwest changing literally everything.

Then we get into something a little deeper: public scandals, viral humiliation, and why the internet loves watching people fail. After listening to Oprah’s interview with Kristin Cabot from the infamous Coldplay kiss cam moment, I started thinking a lot about empathy, internet culture, and how easy it is to forget there’s a real human behind the meme.

Plus:

• My Top 5 obscure holidays
• Listener questions
• What’s currently sitting on my kitchen table
• The importance of celebrating small things

As always, it’s chaotic, reflective, unhinged, and hopefully a little comforting too. Glad you’re here!

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com

Welcome to my first ever Dear Jill episode. You sent in your questions (anonymously, don’t worry), and I’m giving you my honest, off-the-cuff advice. Am I qualified? Absolutely not. But I do have thoughts…a lot of them.

Before we get into that, I’m catching you up on a weekend in the New Hampshire mountains (where things get a little strange), a billboard that raised some serious questions about cremation pricing, and my strong opinions on “plogging” (why are we doing three activities at once??). Also, Effingham, NH. I mean, come on. My favorite town name.

Then we get into your questions. Everything from dealing with a family member no one likes, to friendship heartbreak, to being a chronic people-pleaser, to social awkwardness, to how to tell your girlfriend she’s not a great cook (gently). I’m answering it all in real time. No overthinking, just my best shot at being helpful.

For today’s Top Five, I’m sharing the top 5 pieces of advice I’ve ever received, then I answer a couple of listener questions, and wrap things up with this week’s Jill Pill, a reminder to stop riding everyone else’s emotional rollercoaster and start riding your own wave.

Take what works, leave what doesn’t, and let me know if I should ever do this again.

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

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http://takeajillpill.com

I may need to reevaluate my driving and my sanity, but we’re pushing through anyway.

In this episode, I’m sharing a couple humbling “slow down” moments from strangers on the road, (apparently I’m the problem), along with a small but mighty personal growth win (SRG) and a few life updates, including an upcoming Trader Joe’s giveaway and my latest Love on the Spectrum obsession.

Then we get into more chaos, including the pronunciation debate I cannot let go of. “Aunt” vs. “ant” is officially the hill I will die on, and yes, it involves me almost losing it in a very inappropriate moment.

From there, we get into conspiracies around celebrities who may have faked their own deaths, Tupac, Elvis, Princess Diana, Michael Jackson…and what would actually drive someone to disappear and start over.

I also share the top 5 celebrity deaths that shook me, why those losses hit so hard, and the strange way we grieve people we’ve never met.

We wrap it up with listener questions and a Jill Pill that might be exactly what you need this week: take the risk.

Host: Jill Pickering

Follow me at:

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http://instagram.com/takeajillpillpodcast

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http://takeajillpill.com

In this episode, I’m talking all things songwriting: the hits, the misses, and the really awkward moments in between...of which there are plenty.

I share how I got started writing songs, what it actually looks like to write in Nashville, and some behind-the-scenes stories from co-writing sessions including a few that were not exactly a natural fit. It’s a lot like dating if we’re being honest!

If you’ve ever wondered how songs come to life or what happens when they don’t, this one is for you.

I also answer your questions about the songwriting process, performing, and creativity, break down my top 5 songs of all time, and play an unreleased song I’ve never shared before.

I wrap it up with a Jill Pill that is simple but powerful: tell people what you see in them.

Glad you're here for another fun episode!

Host: Jill Pickering

Follow me at:

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http://instagram.com/takeajillpillpodcast

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http://takeajillpill.com

This one starts with decaf coffee and Starbucks anxiety…and somehow ends with me in a feud with a 90-year-old woman.

Her name’s Mary (not her real name), and yes…she does not like me. And yes, I care a little more than I should. Thumbs down, major glare energy. We talk about why we get hung up on people not liking us, why it’s uncomfortable when we can’t fix it, and when it’s time to just shrug and keep walking.

Also: I ran into my junior high “Boyz II Men” ex (of course I brought up the story), reflections on playing live again after the Hunter Hayes and Blü Eyes show, and a very serious, highly debated Top 5: Ice Cream Flavors. Yes, I’m an ice cream snob.

Take your daily dose of the Jill Pill. Side effects may include laughing at yourself, realizing some people just aren’t your people, and maybe caring a little less (in a good way).

Host: Jill Pickering

Follow me at:

http://instagram.com/jipimusic

http://instagram.com/takeajillpillpodcast

http://tiktok.com/jipimusic

http://takeajillpill.com