Challenge: Make It Interesting

Conversations with Thomas

#Self-Improvement #Thomas Kevin Dolan #Personal Growth #Healing #Guidance #Clarity #Action #Fear #Framework #Motivation #Society #Relationship #Podcasting Education #Inspiring #Succession

46:43

Think you know ChatGPT's custom GPTs? 🤔 Probably not. Last week, we tackled the basics and what's new with OpenAI's refreshed GPTs. For this AI Working Wednesdays episode, we're getting into some advanced techniques to hep you win back time. ↳ using the crazy powerful o3 model to your GPT's advantage ↳ context stacking ↳ custom actions to connect to third party sites Yeah.... don't sleep on this one shorties. Ep 563: ChatGPT's New Custom GPT's: Advanced techniques to win back time Newsletter: Sign up for our free daily newsletter More on this Episode: Episode Page Join the discussion: Thoughts on this? Join the convo and connect with other AI leaders on LinkedIn. Upcoming Episodes: Check out the upcoming Everyday AI Livestream lineup Website: YourEverydayAI.com Email The Show: info@youreverydayai.com Connect with Jordan on LinkedIn Topics Covered in This Episode: Custom GPTs: Advanced Techniques Overview OpenAI's Context Stacking Strategy O3 Model's Thinking Capabilities Building Efficient Custom GPTs Custom Actions and API Integration Zapier Integration for Dynamic Data ChatGPT's Context Window Management Creating Evergreen Podcast Content Timestamps: 00:00 Custom GPTs: Evolution and Insights 03:23 "Mastering GPT Context Stacking" 09:31 "Context Stacking in Chat GPT" 11:20 GPT Context Switching Advantage 15:33 Customizable GPT Usage Explained 19:51 Evergreen Episode Update Strategy 21:44 Optimizing AI for Continued Learning 23:48 "O-Series Models: Advanced AI Capabilities" 28:41 Building GPTs for Episode Research 30:03 GPT Model Customization and Sharing 33:18 Securing API Keys in GPTs 36:55 Zapier Enhances GPT Email Capabilities 42:12 "Use Chrome Extensions for Tokens" 43:48 "AI at Work Wednesdays Survey" Keywords: OpenAI's custom GPTs, advanced techniques, save time, context stacking, o three model, ChatGPT updates, logic and reasoning, plan ahead capabilities, agentic tools, custom actions, third party data, API, building GPTs, leveraging AI, context window, transformer model, generative AI, organization usage, fine tuning performance, productivity enhancement, AI agents, AI tools integration, custom configuration, everyday applications, tech strategies, new rendition, midweek break, AI experts, smarter AI usage, AI-powered planning, AI transformations. Ep 563: ChatGPT's New Custom GPT's: Advanced techniques to win back time Send Everyday AI and Jordan a text message. (We can't reply back unless you leave contact info) Ready for ROI on GenAI? Go to youreverydayai.com/partner…

about a year ago 26:23

MP3•Episode home

Although it felt a bit nebulous, maybe even boring when I thought about sharing a conversation about challenge, I’ve landed on now seeing its merits.

During this podcast I’ll share some thoughts about challenge, challenging ourselves and what all of that really means.

Think back to the last time you challenged yourself.

Most likely, it involved leaving your comfort zone. There's a lot that falls under the umbrella of trying something new. For instance, maybe you ran an extra mile, woke up earlier than usual, or tried a new approach to solving a problem.

It doesn't matter if it's a small challenge or a big one, that takes a year to accomplish. It's still a challenge.

If you're on the road to self-improvement or personal growth, you need to know why and how to challenge yourself.

33 episodes

Challenge: Make It Interesting

Conversations with Thomas

published about a year ago

MP3•Episode home

Although it felt a bit nebulous, maybe even boring when I thought about sharing a conversation about challenge, I’ve landed on now seeing its merits.

During this podcast I’ll share some thoughts about challenge, challenging ourselves and what all of that really means.

Think back to the last time you challenged yourself.

It doesn't matter if it's a small challenge or a big one, that takes a year to accomplish. It's still a challenge.

If you're on the road to self-improvement or personal growth, you need to know why and how to challenge yourself.

33 episodes

#Self-Improvement #Thomas Kevin Dolan #Personal Growth #Healing #Guidance #Clarity #Action #Fear #Framework #Motivation #Society #Relationship #Podcasting Education #Inspiring #Succession

All episodes

Conversations with Thomas

1
Start with How You Failed 17:53

17 days ago17:53

17:53

A Gentle Note Before You Begin to Listen This space holds truth—and sometimes, truth is tender. The story I share here includes reflections on suicidal thoughts and lived experiences with mental health struggles. If this is a sensitive subject for you, please honor your heart as you read or listen. You have full permission to pause, skip, or return when it feels safe. You are not alone. Your well-being matters more than any story. If you or someone you love is struggling, I encourage you to reach out to a trusted support, therapist, or crisis resource in your area. There is help. There is hope. And there is healing. With deep respect for your journey — Welcome. Please begin when you’re ready. Start with How You Failed In this episode of Conversations with Thomas , we flip the script on how we usually measure success. Thomas invites us to start by sharing our failures—the messy, mortifying, oh-shit moments we’d rather keep hidden. Because when we tell the truth about how we fell down, we give ourselves and others permission to get back up. Drawing from his own life—like the day he almost ended it all at Bow Falls in Calgary—Thomas shares how failing to take his own life became his biggest triumph. That failure woke him up to the power of living, to the fierce desire to turn pain into purpose. And he reminds us: failure isn’t the end—it’s the forge that shapes us. Alongside personal stories and scientific insights (like how the brain’s error-monitoring system actually helps us grow), Thomas weaves in humor and heart, showing us that failure is life’s way of recalculating the route. He also shares how his own “coaching misfires” became the catalyst for authentic, human-centered connection—and extends an invitation to listeners to explore the gold in their own failures. So, take a deep breath and join Thomas in this brave conversation. Because in the end, our failures aren’t proof we’re unworthy. They’re reminders we’re alive, we’re learning, and we’re loved. Let your failure become the compass that points you to what matters most.…

Conversations with Thomas

1
Flawsome 13:15

5 weeks ago13:15

13:15

Best for: Humans. Especially the ones trying really hard not to be. Ever felt like a beautiful disaster wrapped in a hoodie of self-doubt? Good. You’re in the right place. In this heart-cracking, belly-laughing episode, Thomas explores the liberating concept of being flawsome —that sacred sweet spot where your mess meets your magic. Popularized by Timber Hawkeye in The Opposite of Namaste , flawsome is about embracing your imperfections not as liabilities, but as your own weird and wonderful superpowers. Thomas serves up soulful insight, relatable stories, a little science (just enough to impress your therapist), and a real-world practice you can do without needing to sage your house or solve your childhood trauma in one go. You'll meet flawsome legends like da Vinci, Lucille Ball, and Mr. Rogers—and also hear about that time Thomas accidentally called himself a "life couch" at a speaking gig. #TrulyIconic This episode is perfect for: • Anyone who’s tired of pretending they’ve got it all together • Recovering perfectionists • Folks still figuring-it-out • Anyone who’s ever autocorrected their “inner growth” into something much less holy • People who find Rumi and ridiculous real-life moments equally healing Come for the laughs, stay for the radical self-acceptance—and leave knowing you don’t have to be flawless to be fabulous.…

Conversations with Thomas

1
Rituals That Bind Us 12:24

7 weeks ago12:24

12:24

Rituals That Bind Us In this soulful and insightful episode, Thomas Kevin Dolan explores the quiet power of ritual—the small, sacred acts that tether us to meaning, to one another, and to ourselves. Broadcasting from Honolulu, Hawai`i, Thomas begins with a heartfelt land acknowledgment and a warm welcome into a conversation that blends research, personal story, and practical wisdom. From the science of rituals to childhood memories of finding peace in a field of grass, Thomas reflects on how even the simplest acts—like bedtime questions, noodle nights, or lighting a candle—can become anchors of connection and care. You’ll hear about rituals that have sustained his marriage, grounded his nervous system, and created a sense of home in the world. He also introduces “The R.I.T. Way”—a three-step method to help you reflect, intend, and tend to rituals of your own. Whether you already have rituals or are just beginning to notice them, this episode invites you to celebrate the beauty in the ordinary. To close, a powerful quote from Audre Lorde reminds us that caring for ourselves through intentional practices isn’t self-indulgence—it’s revolutionary. Expect: — Research-based insights on the psychological power of ritual — Personal stories from Thomas’s life and memoir Little Fag — A three-step method for creating your own rituals — A blend of humor, heart, and grounded wisdom — Gentle inspiration to make meaning in your own daily life Tune in and discover how ritual—no matter how small or quirky—can be a radical act of love.…

Conversations with Thomas

1
Thanking Our Mistakes 13:43

9 weeks ago13:43

13:43

Thanking Our Mistakes What if your biggest mistakes were actually your best teachers? In this heartful (and slightly sparkly) episode of Conversations With Thomas , we explore the radical idea of not just learning from our faults—but actually thanking them. You'll hear: • Why mistakes are neurologically good for us (yes, science backs your awkward moments) • A hilarious coaching fail that became a turning point • Two soul-nourishing practices to transform regret into growth • A love letter to 1988 (featuring a very delayed, very fabulous coming out) • How kintsugi, Carol Dweck, and cosmic whiteboards all tie into your healing journey This isn’t toxic positivity. It’s real, tender, sometimes cringey... and wildly human. Because your cracks aren’t your failure—they’re your art.…

Conversations with Thomas

1
The Platinum Rule 16:02

11 weeks ago16:02

16:02

The Platinum Rule In this episode of Conversations with Thomas , we explore a powerful shift in how we relate to one another: from the Golden Rule to the Platinum Rule—"Treat others the way they want to be treated." Thomas Kevin Dolan invites you into a soulful conversation blending science, story, and spirit. You'll hear insights from psychology, queer wisdom, and personal healing journeys—including a tender story from his book Little Fag: A Story of Self-Acceptance and Healing —that reveal how the Platinum Rule creates deeper, more compassionate connections. With a practical practice called The Platinum Swap , Thomas offers a tangible way to embody this heart-led principle in your everyday relationships. Whether with loved ones, chosen family, or even yourself, this episode is a reminder that true love begins with listening. What You’ll Learn: • The difference between the Golden Rule and the Platinum Rule—and why it matters • How empathy and interpersonal neurobiology deepen connection • Ways queer communities model expansive, attuned love • A story of relational healing through the Platinum Rule • A simple 10-minute practice to strengthen any relationship • How to love others (and yourself) with more nuance, care, and curiosity Who It’s Perfect For: • Heart-centered humans looking to deepen their relationships • Coaches, therapists, and helpers who value attuned connection • Those ready to practice empathy as a verb—not just a feeling…

Conversations with Thomas

1
KindFULLness 13:15

13 weeks ago13:15

13:15

In this warm, witty, and wisdom-packed episode of Conversations with Thomas , host Thomas Kevin Dolan explores the tender art of kindFULLness —a powerful blend of mindfulness and self-compassion. Through vulnerable storytelling, science-backed insight, and just the right dash of humor, Thomas shows how practicing kindFULLness isn’t about escaping life’s mess, but meeting it with a soft heart and curious mind. He shares personal stories from his memoir Little Fag: A Story of Self-Acceptance and Healing , including a middle school mirror moment and an emotional breakdown at his first Pride parade—moments where kindFULLness helped him stay grounded and whole. Thomas also breaks down what the research says, from cortisol reduction to increased emotional resilience, and offers a simple, guided practice to help listeners embody kindFULLness in their daily lives. If your inner critic needs a nap and your soul is craving a little grace, this one’s for you. What You'll Learn: • What kindFULLness is—and why it matters • How to spot your inner critic (and kindly tell it to pipe down) • The science behind self-compassion and stress reduction • A 4-step “Gentle Pause” practice you can use anytime • Why you can be a masterpiece and a work in progress Perfect For: Anyone who’s tired of beating themselves up and ready to show up with more softness, humor, and self-acceptance.…

Conversations with Thomas

1
Bridge Burning 21:37

16 weeks ago21:37

21:37

Bridge Burning How often have you heard quotes like these: “ Keep burning those bridges. It ’ s going to be lonely on that island of yours.” “ Don ’ t burn bridges you may have to cross later.” Or my favorite: “ Don ’ t burn a bridge and expect them to send a boat.” Usually, this is pretty sound advice. The one thing they are all missing is that little asterisk (*) that points to the disclaimer: • Unless that bridge is so screwed up that it might collapse and kill you at any moment. Sometimes you need to burn bridges in order to stop yourself from crossing them again.…

Conversations with Thomas

1
Grind or Ground 22:33

18 weeks ago22:33

22:33

Grind or Ground Grounding allows you to develop the capacity to appreciate your genuine rhythm and feel a natural, relaxing flow in both your internal and exterior worlds. Grind Culture is not really about Making It to The Top. It’s about trying to compensate for a lack of self-worth built in by a society that wants you to feel this way so that it can keep on producing and dominating everything. Rumi shares this: Out beyond ideas of wrongdoing and rightdoing there is a field. I’ll meet you there. When the soul lies down in that grass the world is too full to talk about. When you find that field. Share the location with me and I’ll meet you there.…

Conversations with Thomas

1
The 18-Inch Journey 20:39

20 weeks ago20:39

20:39

The 18 Inch Journey From this inner knowing comes great wisdom of understanding of the truth of your experience and your nature. When we look into our hearts, we are able to access that deep wisdom and use it to inform our minds with crucial information it does not receive from the outside world. It is easy to allow the heart to take a backseat because most of us spend a majority of our lives leading with our brains, preoccupied with the immense amount of stimulus coming from the outside (both good and bad). We must actively remember to check in and to connect with the heart. We need the hearts wisdom to help guide us through all of the outside stimulus. So remind yourself daily, hourly, from moment to moment and ask: • What is my heart telling me or wanting me to know? Become best friends, because if anyone has your best interests in mind, it’s your heart!…

Conversations with Thomas

1
Self-FULL 25:31

22 weeks ago25:31

25:31

Self-FULL Many of you know that I, at one time, had 9 other siblings. And of course, from my Mom’s vantage point, the best version of her children were the ones that weren’t going to be selfish. I was loved when I shared. I hated sharing with my siblings. Having nothing of my own growing up was quite painful. So as much as I learned to share, I preferred to be selfish, at least that’s what I wanted as a little boy. In therapy one day the idea of better self-care was bandied about by my therapist. “What would it be like to be more selfish”, my well-intended therapist asked. I remember starting to cry. Through tear filled eyes I said, “I always thought I wasn’t loved by my Mom when I was selfish.” It was a story I made up when she busted me for not sharing a block of Hershey’s chocolate a friend of my Dad bought for me. After getting me re-grounded he gently asked, “If there was term or concept that meant you focusing on you, but you didn’t use the term selfish, what would it be?” As my eyes lifted to meet his, I began to smile. “What about self-FULL? Would that work?” Like any good therapist worth their salt he asked, “Would that work for you?” “Hell yes!”, I said. In today’s podcast I want to breathe some energy into the concept of being self-full. I’ll also share 6 reasons why living “SELF-FULL” is incredibly generous.…

Conversations with Thomas

1
Badass Ancestors 20:49

24 weeks ago20:49

20:49

BADASS ANCESTORS James Nasymth shares this wisdom, “Our history begins before we are born. We represent the hereditary influences of our race, & our ancestors virtually live in us.” We are part of a lineage, a stream of intention and creation whose fountain springs from our ancestors. Their lives have been lived and completed with a beginning-middle-end. And yet, something of them lives within each of us. I feel compelled to include my ancestors as subject matter for this podcast & in doing so I’m inviting you to call your ancestors forward to listen with you today. Their forces have had a hand in shaping us. It’s a beautiful idea, to see ourselves as a stream, as a lineage, and important to remember and honor those who came before us. This podcast is being recorded in Honolulu, Hawaii. I acknowledge that the unceded ‘Āina, or land, in which I live, called Kakaako, is part of the larger territory recognized by Kānaka Maoli , or indigenous Hawaiians. I'm honored and grateful to be a guest of the Hawaiian Kingdom.…

Conversations with Thomas

1
Refresh 20:13

26 weeks ago20:13

20:13

Refresh I love the word refresh . It’s such a perfect word to describe starting again or returning to something. In fact, we even use it as a computer term. Sometimes when I’m working on my computer, leave it for a while, and then come back, things freeze up. Certain programs aren’t working properly anymore. So I have to refresh my computer screen. And there are times when that means I need to completely reboot. I read recently a very simple, both symbolic & practical, way to refresh your home - open the back door, let out the old energy. Open your front door let in the new energy. Letting in the freshness, letting out the stale. I sense it’s a powerful way to energize or re-energize our lives. In this podcast I’m want to share how it is we might consider a refresh on an emotional level. I’ll offer some very pragmatic ways to do this, all nestled in a bit of philosophy.…

Conversations with Thomas

1
Pause 31:09

29 weeks ago31:09

31:09

It is such a privilege to grow older & as I breathe into each day with gratitude, I realize there is a lot in my life that I find I cannot control. For what seems like a myriad of strategies, learned from brilliant therapists & terrific life coaches, even I at times fall prey to feeling helpless and distraught, while frantically trying to manage what is happening. I scramble to gain ground, when I fall out of integrity, as a way to make up for it. I plunge head first - not heart first - into emotionally charged confrontations nervously rehearsing and strategizing. Sometimes it all feels pretty shitty. The more I allow fear to rule the roost, the more frenetically my body and mind work. Days get overloaded with busyness. Movement feels imperative - which is usually just deflection - with me not wanting to deal with life. Planning for the sake of planning gets ramped up. Worrying, habitual talking, zero listening, fixing, posturing, texting, doom scrolling, binging, consuming, and numbing - these tactics run my life. In the world of doing, achieving and looking to the future, we seldom take the time to pause or be still. We may hear whispers that beckon us into stillness, but they are easily ignored. In this podcast I’m going to chat about how challenging it is to slow down when living in our fast-forward world. I’ll reflect, from personal experience, that there is always a price to pay if we don’t regularly take time simply to pause—to cease activity, to treasure quiet time, and to discern the deep meaning of life’s little moments.…

Conversations with Thomas

1
Are You Arguing With Reality? 29:02

31 weeks ago29:02

29:02

“When you argue with reality, you lose, but only 100% of the time.” I heard this quote for the first time when reading a book by Byron Katie, and my brain screamed that I really needed to pay attention to this sentence. As a WayFinder Coach trained in Byron Katie’s work, literally called The Work. Think about this; when we argue with reality, we are denying what is, what already exists. Who of you listening argues the fact that the sun comes up every day, and that the earth rotates around the sun? Imagine dying on that hill as you argue against these two bits of reality. I’m going to trust, not one of you does, because that is a part of reality that we have come to accept as truth. In this podcast I’m going to chat about accepting what is, how to more easily embrace reality & share some insight on how to make this common thread across our challenges: our inability to deal with reality - a wee bit easier.…

Conversations with Thomas

1
Challenge: Make It Interesting 26:23

33 weeks ago26:23