What happens when you're a Five and a mom? This week’s episode is a special podcast takeover by Enneagram experts Sam E. Greenberg, PhD and Melissa Kircher—both Fives and both moms. They swap stories, laugh about their quirks, and get painfully honest about the challenges and strengths of navigating motherhood as a Five. Whether you’re a Five parent yourself or trying to understand one, this conversation pulls back the curtain on what it’s really like to raise kids as a deeply introspective, ene...
Jun 10, 2025•1 hr 12 min•Ep. 49
Some rabbit holes are deeper than others, and as Fives we often fall in headfirst. In this episode, we explore the obsessive way Fives pursue information: how it starts, what fuels it, and what happens when it spirals out of control. We share personal stories of late-night research binges, conspiracy rabbit holes, and the paradox of being both empowered and paralyzed by too much knowledge. We also look at what pulls us out—how connection, embodiment, and purpose help break the loop. IN THIS EPIS...
May 21, 2025•1 hr•Ep. 48
We Fives often pride ourselves on intellect, but emotional intelligence is a whole different skill set. In this episode, Sam E. Greenberg, PhD. joins us to explore what emotional intelligence actually means, why it's challenging for Fives, and how our relationships have pushed us to grow. We share real-life stories about misreading emotions, struggling to stay in our bodies, and the surprising benefits we've discovered from learning to feel more deeply. We also dig into the shadow side of emotio...
Apr 29, 2025•49 min•Ep. 47
Fives often feel like outsiders, but what if the group we’ve always longed for already exists? In this episode, we invite two longtime friends to join us for a candid conversation about what it’s really like to be friends with a Five. From hilarious stories to hard truths, we explore the highs and lows of maintaining deep, long-term friendships—especially when you tend to live in your head. We reflect on shared histories, missed connections, and the emotional work required to sustain meaningful ...
Apr 22, 2025•1 hr•Ep. 46
In this live episode, we explore a surprising tension many Fives feel: the deep desire to be known and understood, and the equally strong instinct to hide. We unpack what’s really behind our aversion to vulnerability, how our subtypes shape this dynamic, and what it takes to show up even when we’d rather stay in our heads. We also check in on how we’re actually doing, share what we’ve been researching lately (spoiler: lots of ChatGPT experiments), and talk about our current areas of growth. Plus...
Apr 15, 2025•1 hr•Ep. 45
Fives pride ourselves on independence, but friendship requires letting people in. In this honest and deeply personal episode, we explore what friendship means to us as Fives—and why it’s so complicated. We share stories of how our personalities have made friendship harder, how we’ve grown to value it more, and the unexpected ways we’re learning to show up more authentically and connect more deeply. From childhood loneliness to cold plunges and community-building, we dive into the vulnerabilities...
Apr 08, 2025•1 hr 28 min•Ep. 44
This is an After Thoughts episode, an unstructured, unedited debrief of everything we didn't say in the last episode—this time unpacking our conversation on intuition . And boy, does this one take some turns... We get into how our Five wings shape the way we approach intuition, with Josiah leaning more into the mystical side while Cody stays grounded in practicality. That leads us into a discussion on how our worldviews have shifted over time, especially in relation to religion, belief, and ques...
Mar 27, 2025•1 hr 24 min•Ep. 43
Fives rely on analysis and clarity, but intuition offers something logic can't: a deeper wisdom that defies explanation. In this episode, we explore what intuition is, why Fives struggle to trust it, and how embracing it can positively influence our lives. We share our personal experiences with intuition, examine how it's different from emotional decision-making, and discuss unconventional theories that stretch our understanding of time and consciousness. We also dive into the tension between in...
Mar 20, 2025•51 min•Ep. 42
Can Fives really be expressive and outgoing? The stereotype says no—but we’re here to challenge that idea. In this episode, we unpack the myth that Fives are always quiet, reserved, and withdrawn, and we share our own experiences of learning to express ourselves in the world. Plus, we introduce a new structure for our live episodes, featuring a mix of community engagement, deep dives, and a little bit of fun. We also announce huge changes to the podcast, including moving to a weekly format, merg...
Mar 13, 2025•59 min•Ep. 41
Fives value logic and control, but anxiety challenges both. In this episode, we explore how Fives experience anxiety, why we often rationalize instead of feeling it, and how avoiding it can make things worse. We share personal stories, unexpected ways anxiety manifests in the body, and strategies that have helped us manage it—including some unconventional ones. We also dive into the tension between self-reliance and vulnerability, the impact of anxiety on relationships, and the surprising power ...
Mar 06, 2025•1 hr 8 min•Ep. 40
What's your attachment style as a Type 5? In this season finale episode, Sam E. Greenberg joins us again to walk us through Attachment Theory and what we can learn about being a Five by studying the different Attachment Styles. If the Enneagram has helped you as a Five and you're curious about another framework you can use to better understand yourself, then this episode is for you. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/39 to join the conversation! ...
Apr 09, 2024•59 min•Ep. 39
What keeps Type 5s from connecting? In this episode, we delve into Josiah's experience of identifying and dismantling the things that were holding him back from connecting with others, and why connection is so important for Fives. If you've ever found it difficult to connect with others as a Five, then this episode is for you. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/38 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tai...
Apr 02, 2024•1 hr 5 min•Ep. 38
Are you on the spectrum or are you a Type 5? In this episode, we join Sam E. Greenberg to explore the overlap of traits between being a Five and being on the autism spectrum. We also talk through Cody's experience of being diagnosed with Asperger's and how that shows up for him as a Five. If you've ever wondered about the difference between being a Five and being on the spectrum, then this episode is for you. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/37...
Mar 26, 2024•54 min•Ep. 37
How do Type 5's feel about commitment? In this episode we share how we've handled various types of commitment as Fives and how we might approach commitment in a way that doesn't burn us out. If you've ever struggled with commitment as a Five, this episode is for you. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/36 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind. 🔹 Practical strategies to st...
Mar 19, 2024•57 min•Ep. 36
How do Type 5s feel about incompetance? In this episode, we delve into why we get so triggered when people around us are incompatent, why Fives have a fear of incompetance, and what steps we can take to start overcoming this fear. If feeling incompatent has ever held you back as a Five, then this episode is definitely for you. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/35 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tai...
Mar 12, 2024•56 min•Ep. 35
How do Type 5s handle being part of a family? In this episode, we delve into what family life was like growing up as Fives, how useful the internal family systems framework is, and what we want our own family dynamics to be. And we talk about Josiah's hair for like 20 full minutes for some reason. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/34 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind...
Mar 05, 2024•1 hr 28 min•Ep. 34
What do Type 5s think about therapy? In this episode, we sit down with Liz Landry, friend of the show and licensed therapist, to talk through what to expect from therapy as a Five, what has held us back from going to therapy in the past, and how to find a therapist that works for you. If you've ever considered therapy as a Five but have been on the fence about it, then this episode is for you. Note: You can follow Liz on Instagram at @yourhonesttherapist . Want to know what other Fives are sayin...
Feb 27, 2024•48 min•Ep. 33
This is is our most requested episode to date, so we gave the crowd what they wanted. And it's a bunch of nonsense, so you're welcome :-) The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind. 🔹 Practical strategies to stop overthinking and start engaging. 🔹 Growth, connection, and energy management—without the fluff. 👉 Sign up free at enneagramfive.com/newsletter . *** RECOMMENDED NEXT EPISODE: ➡️ #27: Subtypes *** CONNECT: 📷 Connect on Instagram 🧵 Connect...
Feb 20, 2024•1 hr 56 min•Ep. 32
How do Type 5s deal with feeling down? In this episode, we dive into what it feels like to be depressed as a Five, various triggers that cause us to feel down, and some techniques we've used to climb back out of the abyss. If you've ever struggled with depression as a Five, then this episode is for you. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/31 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactiv...
Feb 13, 2024•1 hr 5 min•Ep. 31
What are the nine levels of health for a Type 5? In this episode, we join once again with our good friend Sam E. Greenberg, PhD (a.k.a the Enneagram Sexpert) to deep dive on the levels of health and what they mean for Fives. If you've ever wondered why one moment you feel like a sage and the next moment like a schizoid, then this episode is for you. PS. Go follow Sam on Instagram at @ennea_gasm ! Want to know what other Fives are saying about this episode? Visit enneagramfive.com/30 to join the ...
Feb 06, 2024•1 hr 18 min•Ep. 30
What do Type 5's think of conspiracy theories? In this episode, we dig into Josiah's philosophy of conspiracy theories and why they're so important for Fives (and everyone, according to him). So grab your tin foil hat and join us as we see how far down the rabbit hole goes. Note: For more info on this topic, check out Wendigoon's Conspiracy Theory Iceberg series Want to know what other Fives are saying about this episode? Visit enneagramfive.com/29 to join the conversation! The Newsletter Built ...
Jan 30, 2024•1 hr 37 min•Ep. 29
How do Fives feel about Politics? To kick off Season 4, we unleash our inner anarchists and share our own political journeys, as we resist the urge to burn the system down and instead focus on building something new. If you have political opinions but never share them because you feel like it's pointless, then this episode is for you. Note: For a deeper dive on some of these topics, Josiah recommends the book The Crash Course by Chris Martenson. Want to know what other Fives are saying about thi...
Jan 23, 2024•2 hr 21 min•Ep. 28
Why are some Type 5's so different from others? In this season finale episode, we bring back Sam Greenberg, aka the Enneagram Sexpert , to deep dive on the Social, Sexual, and Self-Preservation subtypes of Type 5 and how instinctual stacking works. You also get to listen in as we attempt to figure out our own subtype stackings in real time. If you're looking to gain better clarity on the wide variation in the different types of Fives, you'll definitely want to listen to this whole episode. You w...
Sep 27, 2022•1 hr 18 min•Ep. 27
How do Type 5's deal with uncertainty? In this episode, we talk about how we handle uncertain times as fives and what we can do to thrive rather than spiral. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/26 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind. 🔹 Practical strategies to stop overthinking and start engaging. 🔹 Growth, connection, and energy management—without the fluff. 👉 Sign up...
Sep 20, 2022•49 min•Ep. 26
Want to know what life is like as a female Type 5? In this episode, we interview 3 female Fives from our community about their unique experiences, what motherhood is like as a Five, and what advice they would give to other female Fives like them. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/25 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind. 🔹 Practical strategies to stop overthinking and s...
Sep 13, 2022•54 min•Ep. 25
Is life meaningless? Does anything matter? In this episode, we unpack why Type 5s tend to embrace nihilism and how we can live with the absurdity of our existence. Yay! Want to know what other Fives are saying about this episode? Visit enneagramfive.com/24 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind. 🔹 Practical strategies to stop overthinking and start engaging. 🔹 Growth, connection, and energy management—without the fluff....
Sep 06, 2022•53 min•Ep. 24
Ever wonder what those lines are coming out of Type 5 on the Enneagram? In this episode, we share our experiences integrating to 8 and disintegrating to 7, as well as the pros and cons of each. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/23 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind. 🔹 Practical strategies to stop overthinking and start engaging. 🔹 Growth, connection, and energy mana...
Aug 30, 2022•1 hr 8 min•Ep. 23
Do you feel like you fit in anywhere as a Type 5? In this episode, we delve into what it means to have a community, why it's often so difficult to feel like we belong to any group, and how we've overcome the challenges of fitting in. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/22 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind. 🔹 Practical strategies to stop overthinking and start engaging...
Aug 23, 2022•1 hr 12 min•Ep. 22
How do Type 5's handle grief? In this episode, we bring professional therapist Liz Landry back onto the show to unpack how we grief, why grief should be understood outside the context of death, what to do when people around you are grieving, and whether or not it's weird that death doesn't bother Josiah. This conversation is comprised of segments originally recorded as a live video stream for our Enneagram Five: After Hours podcast. To view the unedited live stream, as well as the rest of our Af...
Aug 16, 2022•1 hr 6 min•Ep. 21
What do Type 5's think about death? In this episode we delve into our personal experiences dealing with death and the thought of dying ourselves, and dig into why death bothers some of us more than others. Want to know what other Fives are saying about this episode? Visit enneagramfive.com/20 to join the conversation! The Newsletter Built for Fives 🔹 Get weekly insights tailored for your overactive mind. 🔹 Practical strategies to stop overthinking and start engaging. 🔹 Growth, connection, and...
Aug 16, 2022•56 min•Ep. 20
