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S2: Episode 65: We Thought Helping the Children in our Life to Be New at Something Was Supposed to Be Easy
Jun 3, 2026
40m 20s
S2: Episdde 64: We Thought the Next Chapter (College) Was Supposed to Be Easy
May 27, 2026
49m 16s
S2: Episode 63: We Thought Talking About Mental Health Was Supposed to Be Easy
May 20, 2026
42m 49s
S2: Episode 62: We Thought Slowing Down with Nature Was Supposed to Be Easy
May 15, 2026
33m 00s
S2: Episode 61: We Thought Playing by the Rules Was Supposed to be Easy (and Fair)
May 6, 2026
47m 35s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/3/26 | ![]() S2: Episode 65: We Thought Helping the Children in our Life to Be New at Something Was Supposed to Be Easy | Trying something new sounds exciting… until you're actually the beginner. In this episode, Amy and Cheryl sit down with friend and guest Erin Smith-Gaken to explore what happens when we step outside of our comfort zones. The conversation begins with children and activities sports, dance, hobbies, and the growing pressure to specialize at younger and younger ages but quickly expands into a larger discussion about comparison, confidence, grit, and what it means to be a beginner at any stage of life. Together, they explore how parents, coaches, and communities can either encourage or discourage growth, why being "new" has become so uncomfortable, and how many of us carry those same fears into adulthood when considering career changes, new hobbies, or unexpected opportunities. Whether you're helping a child discover their interests or wondering if it's too late to try something yourself, this conversation is a reminder that growth rarely begins with expertise, it begins with curiosity. About Our Guest Erin Smith-Gaken is a learning and development professional, parent, and lifelong learner who recently made the transition from higher education into corporate learning and HR. As the mother of two children, Erin brings both personal and professional perspectives to conversations about growth, confidence, and trying new things. Her passion for helping people step outside of their comfort zones shines throughout this thoughtful discussion. Key Topics and Takeaways Why children are often expected to specialize in activities at increasingly younger ages. The difference between exploring interests and feeling pressured to choose a lifelong path. How comparison can discourage both children and adults from trying something new. The importance of creating environments where beginners feel welcome. Why grit develops through struggle, practice, and persistence. The role parents play in supporting children through success, failure, and uncertainty. How social media can distort our understanding of learning and mastery. The challenge of career transitions and recognizing transferable skills. Imposter syndrome and the belief that there is only one "right" path into a profession. Why curiosity is often the first step toward personal growth. The importance of allowing ourselves to be beginners again. How supportive relationships help us take risks and build confidence. Memorable Lines "The skill of learning to be new and step outside and take risks is so important all throughout your life." — Amy Bond "Almost feeling like you've missed the boat before you're eight." — Cheryl Priest "We're no longer coaching to teach and learn something new. We're coaching for enhancement." — Erin Smith-Gaken "I think we get stuck in the idea that there's only one route from point A to point B." — Erin Smith-Gaken "I'd like the box to be gone." — Cheryl Priest "Sometimes it's our own selves that are getting in the way of trying something new." — Erin Smith-Gaken "Growth rarely starts with confidence. It starts with curiosity." — Inspired by the conversation Challenge for the Week Think about something you've always been interested in trying but never pursued because you felt too old, too inexperienced, or too far behind. Now ask yourself: What would happen if I allowed myself to be a beginner? What am I afraid might happen? What could I gain if I tried anyway? Then take one small step. Sign up for a class. Watch a tutorial. Attend a meeting. Ask a question. You don't have to become an expert this week. Just give yourself permission to begin. Additional Resources Carol Dweck's work on Growth Mindset Brené Brown's research on vulnerability and courage Angela Duckworth's work on Grit TED Talk: The Power of Believing You Can Improve by Carol Dweck TED Talk: Grit: The Power of Passion and Perseverance by Angela Duckworth | 40m 20s | ||||||
| 5/27/26 | ![]() S2: Episdde 64: We Thought the Next Chapter (College) Was Supposed to Be Easy | This week, Amy and Cheryl sit down with residence hall director and higher education professional Jessa Heroux-Croy for an honest conversation about the transition to college - not just for students - but for the families and supporters who love them. From roommate dynamics and campus culture to homesickness, connection, and learning how to support young adults without rescuing them, this episode offers practical advice and emotional reassurance for anyone navigating the college transition season. Whether you’re preparing to send a student off for the first time, welcoming one back home for the summer, or remembering your own experience of figuring out who you were in those years, this conversation is full of warmth, wisdom, and perspective. Guest Introduction Jessa Heroux-Croy is a residence hall director working in higher education and student affairs. She lives and works on campus alongside university students and supports them through everything from move-in and roommate conflicts to leadership development, connection, and personal growth. Passionate about student belonging and communication, Jessa brings both professional expertise and personal experience to conversations about what it really means to transition into college life. Key Topics & Takeaways Why campus “fit” matters more than prestige alone Questions families should ask during college visits The hidden emotional transition of coming home after freshman year How roommate conflicts are often really communication conflicts Why students need the act of connection to be intentional, not passive What residence hall staff actually do to support students Ways parents can shift from “fixer” to “coach” The evolving culture of dorm life after COVID and technology changes Creative ways families can stay connected beyond care packages What students really need before moving into the dorms Common dorm shopping mistakes and overlooked essentials Why getting involved on campus early on matters so much Memorable Lines “You can’t wait for connection to come to you. You have to meet it halfway.” Jessa Heroux-Croy “Who do you need me to be for you right now?” Amy Bond “Sometimes students are communicating, you’re just not understanding the way they’re trying.”-Jessa Heroux-Croy “College is 100% what you make it. What you’re open to is what you get out of it.” - Jessa Heroux-Croy “You’re always the parent, but you start transitioning more into the coach.” - Amy Bond “What does communication mean to you?” - Jessa Heroux-Croy “Say yes to everything and figure out what works for you.” - Jessa Heroux-Croy Challenge for the Week If you know a child, student, or young adult preparing for a transition this year, ask them one intentional question this week: What are you most excited about? What are you nervous about? What kind of support feels most helpful to you right now? And if you’re the one entering a new season yourself, consider:What would it look like to stay open instead of trying to have everything figured out already? Additional Resources Explore your future college’s housing and residence life webpages before move-in Look for orientation events, involvement fairs, and student organization showcases Review residence hall prohibited items lists before shopping Encourage students to fill out roommate compatibility forms honestly | 49m 16s | ||||||
| 5/20/26 | ![]() S2: Episode 63: We Thought Talking About Mental Health Was Supposed to Be Easy | In this episode of This Was Supposed to Be Easy, Amy & Cheryl sit down with Dr. Allison Arnekrans, counselor educator, clinician, and private practice owner, for an honest conversation about therapy, emotional wellness, relationships, and what it really means to care for ourselves in a world that often expects us to “just keep going.” Together, they explore the realities of counseling, the misconceptions people often have about therapy, and why emotional health deserves the same level of attention as physical health. The conversation also touches on high-achieving women, communication, burnout, vulnerability, and the importance of feeling truly heard. This episode is thoughtful, validating, and deeply human, whether you’ve been in therapy for years, are considering it for the first time, or simply want to better understand yourself and the people around you. Guest Introduction About Dr. Allison Arnekrans Dr. Allison Arnekrans is a professor of Counselor Education at Central Michigan University and a practicing clinician specializing in women’s issues, high-achieving professionals, couples communication, and emotional wellness. With experience in both higher education and private practice, she brings a grounded and compassionate perspective to conversations around therapy, relationships, and mental health. Dr. Arnekrans is passionate about helping people feel seen, understood, and empowered in their personal growth journeys. Key Topics & Takeaways Why therapy is often misunderstood The difference between “listening to respond” vs. “listening to understand” How high-achieving individuals can struggle silently The emotional load many women carry behind the scenes Why vulnerability can feel uncomfortable but necessary Communication patterns in relationships The value of emotional self-awareness How counselors balance empathy with professional boundaries Why growth often begins with honest conversations The importance of normalizing mental health support Challenge for the Week This week, try creating space for one deeper conversation. Instead of rushing to fix, advise, or respond, practice simply listening. Ask someone: “How are you really doing?” “What’s been weighing on you lately?” “What do you wish people understood better about your experience?” And if you’ve been considering therapy or additional support for yourself, let this be your reminder that asking for help is not weakness, it’s self-awareness. | 42m 49s | ||||||
| 5/15/26 | ![]() S2: Episode 62: We Thought Slowing Down with Nature Was Supposed to Be Easy | What if something as simple as stepping outside… isn’t actually simple anymore? In this reflective and eye-opening conversation, Amy and Cheryl sit down with Dr. Joellen Lewsader to explore what it really means to slow down, reconnect, and be present in nature. What starts as a conversation about a sabbatical becomes a deeper realization that many of us have lost touch with something essential. Through her experience studying sylvotherapy (forest bathing), engaging with nature-based research, and intentionally shifting her life’s focus, Dr. Lewsader shares how reconnecting with nature is not just a peaceful idea… it’s a practice. And maybe the biggest surprise?Slowing down, being present, and disconnecting from technology, things that seem like they should be easy, actually take intention, time, and relearning. This episode is a gentle invitation to pause, breathe, and reconsider how we move through the world. 🎤 Guest Spotlight: Dr. Joellen Lewsader Dr. Joellen Lewsader is a professor of early childhood development and learning in the Department of Human Development and Family Studies. With a PhD in Human Development and Family Studies, her work bridges research, teaching, and real-life applications, particularly in the early childhood space. During a recent sabbatical, Dr. Lewsader shifted her research and personal focus toward nature-based learning and well-being. She explored sylvotherapy (forest bathing), engaged in interdisciplinary learning through Native American studies, and conducted research on children’s connectedness to nature and biophilia. Her work highlights the powerful role nature plays across the lifespan, from supporting children’s development to helping adults reconnect with presence, purpose, and well-being. Through both her research and personal journey, she brings a thoughtful and deeply human perspective to what it means to live more intentionally. 💡 Key Topics & Takeaways The moment when perspective shifts from “how long I’ve lived” to “how much time I have left” Why reconnecting with nature often requires intentional unlearning What forest bathing (sylvotherapy) actually is, and what it is not The surprising difficulty of being present without technology How nature impacts our nervous system, stress levels, and overall well-being The idea that humans and nature are deeply interconnected (and what that really means) Why re-entry after rest (like a sabbatical or vacation) can feel harder than expected The importance of daily, intentional practices, not just one-time experiences How children naturally connect to nature, and what adults can learn from that The concept of biophilia (our innate or learned love of nature) Why slowing down is not inefficient, it’s necessary Memorable Lines “How much time do I have left here, and what do I want to focus on?” - Dr. Joellen Lewsader “I’m finally getting glimpses of what I want it to feel like.” - Dr. Joellen Lewsader “Leave your phone inside.” - Dr. Joellen Lewsader Try This: Challenge for the Week Step outside… without your phone. Start small: 5 minutes No destination No task Just notice: What do you hear? What do you see that you normally miss? What happens when you don’t rush? Bonus:If you’re with a child, let them lead. Follow their pace. Notice what they notice. Additional Resources Explore the concept of forest bathing (sylvotherapy) Look into biophilia and children’s connection to nature Try simple practices like mindful walking, sitting in nature, or observing without distraction Visit local parks, trails, or even your own backyard with fresh intention | 33m 00s | ||||||
| 5/6/26 | ![]() S2: Episode 61: We Thought Playing by the Rules Was Supposed to be Easy (and Fair) | What if one of the biggest things we were taught about life… wasn’t entirely true? In this deeply honest and eye-opening conversation, Amy and Cheryl sit down with Dr. Sherene McHenry to unpack a belief many of us were raised with:If you’re kind, if you follow the rules, if you treat people well… everything should work out. But what happens when it doesn’t? Dr. McHenry shares her personal and professional journey of realizing that while kindness matters, it’s not enough on its own. Relationships aren’t always easy, and without boundaries, conflict skills, and emotional awareness, even the nicest people can find themselves hurt, overwhelmed, or taken advantage of. This episode explores the hard truth: not everyone plays by the same rules. And learning how to navigate that reality might be one of the most important life skills we develop. Guest Spotlight: Dr. Sherene McHenry Dr. Sherene McHenry is a full-time author, speaker, and relationship expert with a doctorate in counseling. With decades of experience as both a counselor educator and practitioner, she brings a deeply grounded, real-world perspective to the complexities of human relationships. She is the author of multiple books, including Pick: Choose to Create a Life You Love and Navigate: Understanding the Five Types of People, where she helps individuals better understand themselves, others, and the patterns that shape their interactions. Dr. McHenry’s work focuses on equipping people with the skills many of us were never formally taught—how to set boundaries, navigate conflict, and build healthy, sustainable relationships both personally and professionally. Her approach blends practical tools, lived experience, and emotional honesty, making her insights both relatable and transformative. Key Topics & Takeaways The belief many of us were raised with: “If you’re nice, others will be nice back” The difference between problem solving vs. problem managing How “taking the bait” keeps us stuck in unhealthy dynamics The two common defensive reactions to feedback: Blowing up (intimidation) Breaking down (emotional overwhelm) Why boundaries are not punishment, they’re protection How emotional manipulation can show up in subtle ways Why “canceling” people too quickly can do more harm than good The importance of giving people the opportunity to grow How to recognize when a relationship is no longer safe or healthy The role of therapy, journaling, and self-awareness in healing The truth: healthy relationships require courage, not just kindness Memorable Lines “I thought everything was going to be fair and easy… and then life hit me.” “Nice people without boundaries are the least equipped for difficult people.” “Why do you always take the bait?” “When people tell you who they are, believe them.” “You don’t solve every problem; you learn to manage some of them.” “This relationship works as long as you have no needs, no feelings, and no wants.” “The only thing worse than being brave… is staying stuck.” “If it bothers you for more than an hour, it’s worth addressing.” “You earn your way into my life, and I get to choose how close you come.” Try This: Challenge for the Week Think about a relationship or situation in your life that feels… hard. Then reflect: Have you been trying to solve something that actually needs to be managed? Is there a boundary you haven’t clearly communicated yet? What truth about your feelings have you been avoiding? Then take one small step: Write the letter (even if you don’t send it) Practice the boundary out loud Or simply name the feeling you’ve been pushing aside Additional Resources Pick: Choose to Create a Life You Love by Dr. Sherene McHenry Navigate: Understanding the Five Types of People by Dr. Sherene McHenry Try journaling or writing a “freedom letter” to process unresolved emotions Consider working with a licensed therapist for support with boundaries and conflict Connect with us Website: https://supposedtobee | 47m 35s | ||||||
| 4/29/26 | ![]() S2: Episode 60: We Thought Finishing Simple Tasks Was Supposed to be Easy | We’ve all had those moments, the quick errand that turns into a three-hour adventure, the “simple” task that somehow spirals into a full-day project, or the thing we swore would take five minutes… and absolutely did not. In this episode, Amy and Cheryl go back to the heart of their podcast title and unpack the reality behind it: life rarely goes as easily (or quickly) as we expect. Through relatable, laugh-out-loud stories, from store hopping for a single item, to international hotel mishaps, to crafting projects gone sideways, they explore why “easy” isn’t always easy. More importantly, they invite you to reframe those moments: What if these frustrating experiences are actually the stories we’ll laugh about later? What if they’re what make us more interesting, more connected, and a little more human? Key Topics & Takeaways The myth of “quick and easy” tasks, and why they often expand “Give a mouse a cookie” moments that derail our time The internal debate: call vs. text vs. email (and when none of them work!) When systems should be easy… but absolutely aren’t (hello, cancellations and subscriptions) The hidden cost of DIY: time, energy, and frustration Finding humor in everyday inconveniences Reframing frustration into connection and storytelling The power of asking: What’s the hack? Memorable Lines “I thought this would take 10 minutes… and suddenly it’s half my day.” - Amy “There is no true sound method to that madness at all.” - Cheryl “You must do the thing you hate.” - Amy “It should have been easy… but it kept revisiting me.” - Cheryl “It is never going to be simpler if I make it myself.” — Amy Try This: Challenge for the Week Think about one thing this week that should have been easy but wasn’t. Then reflect: What made it harder than expected? Is there a “hack” you discovered (or could try next time)? How might this become a story you laugh about later? Bonus: Share your story with someone, you might be surprised how quickly it turns into connection. Additional Resources “100 Bad Days” by AJR Reflect on your own “this was supposed to be easy” moments as journaling prompts Connect with us Website: https://supposedtobeeasy.com/ Our Podcast Home: https://supposedtobeeasy.podbean.com/ Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy We want to hear from you! Follow and share your key takeaways, ideas, and inspiration! | 29m 21s | ||||||
| 4/22/26 | ![]() S2: Episode: 59 We Thought Talking About Life’s Choices Was Supposed to be Easy✨ | life choicesregrets+3 | Ranee Conley | AudibleThe Midnight Library+5 | — | The Midnight LibraryMatt Haig+2 | — | 43m 55s | |
| 4/15/26 | ![]() S2: Episode 58: We Thought Making the Time to Read Was Supposed to be Easy✨ | readingbooks+5 | — | GoodreadsApple Podcasts+5 | — | shared experienceaudiobooks+2 | — | 33m 20s | |
| 4/8/26 | ![]() S2: Episode 57: Parenting with Joy (Even When It’s Hard)✨ | parentingjoy+3 | Casey Sterle | Apple PodcastsSpotify+3 | — | educationmotherhood+2 | — | 57m 10s | |
| 4/1/26 | ![]() S2 Episode 56: We Thought Using Time Was Supposed to be Easy!✨ | timememory+6 | — | Apple PodcastsSpotify+4 | — | The Seven Year SlipCOVID+3 | — | 31m 15s | |
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| 3/25/26 | ![]() S2 Episode 55: We Thought Celebrating Our Wins Was Supposed to Be Easy!✨ | celebrationself-acknowledgment+3 | — | — | — | milestonepressure of timelines+3 | — | 28m 16s | |
| 3/18/26 | ![]() S2 Episode 54: Planning Meaningful Travel – Lessons from Reggio Emilia✨ | traveleducation+3 | Cheryl | Apple PodcastsSpotify+3 | Reggio EmiliaItaly | Reggio Emiliaearly childhood education+3 | — | 38m 52s | |
| 3/11/26 | ![]() S2 Episode 53: We Thought Scheduling a Night in with Friends Would Be Easy✨ | friendshipscheduling+3 | — | Apple PodcastsSpotify+2 | — | book clubcompromise+2 | — | 25m 39s | |
| 3/4/26 | ![]() S2 Episode 52: We Thought Listening to Someone Say No Was Supposed to Be Easy✨ | boundariescommunication+3 | — | Apple PodcastsSpotify+3 | — | saying nopersonal stories+3 | — | 38m 33s | |
| 2/25/26 | ![]() S2: Episode 51: When You Need to Say No (Even When You Don’t Want To)✨ | saying noself-trust+3 | — | — | — | capacityexhaustion+3 | — | 38m 49s | |
| 2/18/26 | ![]() E2 Episode 50: We Thought Creating 50 Episodes of a Podcast Was Supposed to Be Easy✨ | connectionjoy+4 | — | E2Apple Podcasts+4 | — | milestonehonest conversation+4 | — | 47m 26s | |
| 2/11/26 | ![]() S2 Episode 49: We Thought Building Hope Was Supposed to Be Easy | In a world that feels loud with bad news, Cheryl and Amy slow down to talk about something both tender and surprisingly practical: hope. Inspired by a conversation between Mayim Bialik and Simon Sinek on optimism vs. pessimism, they explore what hope really is (and what it isn’t). Together, they name how easy it is to spiral into helplessness—and how hope can be a mindset plus action, not denial or “marshmallow fluff.” From “good news” algorithms, to boundaries that protect mental health, to Cheryl’s seed-ordering ritual as a tiny act of future-facing faith, this episode offers grounded ways to build hope—especially when it doesn’t come naturally. The conversation closes with Emily Dickinson’s “Hope is the Thing with Feathers,” an invitation to carry hope together. Key Topics and Takeaways Hope vs. Optimism (and why it’s not toxic positivity): Hope doesn’t ignore hard things—it acknowledges reality and believes change is possible. Hope is buildable: You’re not either “born hopeful” or not. Hope can be practiced and strengthened over time through small, intentional shifts. Mindset + action: Hope isn’t passive wishing. It includes agency (“I have influence”) and pathways (finding a route forward)—a nod to Snyder’s Hope Theory and VIA Character Strengths. How to “train your attention” toward hope: Curating what you consume (news, social media, “good news” accounts) and noticing kindness in everyday moments can restore perspective. Boundaries are part of hope: Being hopeful doesn’t mean giving everyone access to you. Protecting your mental health can be a hopeful act. Hope and grief can coexist: Amy names the difference between hoping and wishing—how “wishing things were different” can activate grief, and how hope can live alongside grieving what was or what could have been. Micro-practices that cultivate hope: “Two good things” noticing (acts of kindness, small goodness) Hope journaling (future-oriented reflection + next steps) Turning hope into a SMART goal (one small step counts) Having multiple pathways ready (Plan A, B, C) Leaning on hopeful people—hope grows when shared Memorable Lines “True optimism, true hope, is actually grounded in action.” “Hope is mindset plus action together.” “It’s not blinders… it helps to see the good things that are also happening.” “One of the ways for me to remain hopeful is to be aware of what I need to be hopeful… and it doesn’t mean everyone gets access to me.” “I wish you peace… I hope you find comfort… I hope you meet your goals in a way that doesn’t cause harm to other people.” “I’m going to grieve the loss of what was… and hope for the best.” “There’s so much hope inside the seed.” “Hope grows when it’s shared with others.” This Week’s Gentle Challenge Try a “Hope Practice” for several days—small on purpose. Choose one: Two Glimpses of GoodEach day, notice two moments of kindness, humor, or decency (tiny counts). Write them down or text them to someone. Hope Journaling (5 minutes)Answer: What’s one thing I’m looking forward to?Then: What’s one baby step I can take this week?Bonus: Write two alternate pathways in case your first plan doesn’t work. Plant a Seed (literal or metaphorical)Do one small future-facing action that says: I believe something good can grow here.Order seeds. Start a file. Send the email. Make the appointment. Take the walk. And if you’re willing: share your hope practice with Cheryl and Amy—your story might become someone else’s “crumb” of hope this week. Note: This episode reflects personal experiences and cited research summaries; it’s not therapy or legal advice. For personal situations, consult a qualified professional. Connect with us Website: https://supposedtobeeasy.com/ Our Podcast Home: https://supposedtobeeasy.podbean.com/ Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy We want to hear from you! Follow and share your key takeaways, idea | 32m 57s | ||||||
| 2/4/26 | ![]() S2 Episode 48: We Thought Accepting a Leadership Role Was Supposed to Be Easy | Leadership is often talked about as a natural next step, something you should want, something that comes with clarity, confidence, and readiness. But what if that story no longer fits? In this episode, Amy and Cheryl unpack why so many capable, thoughtful people are hesitant to step into leadership roles right now. Through honest reflection, real-world examples, and a post-COVID lens, they explore how leadership has changed, why it feels heavier than it used to, and what organizations (and individuals) might need to rethink if they want leadership to feel sustainable, and worth it, again. This conversation isn’t about convincing anyone to lead. It’s about understanding what leadership actually costs today, what support is missing, and how we might redesign leadership in ways that feel human. Key Topics & Takeaways Why does leadership no longer feel like an obvious or attractive next step for many people How COVID, burnout, and constant change reshaped expectations of leaders The emotional and invisible labor that often comes with leadership roles Why boundaries, clarity, and support matter more than ever The difference between being good at your job and wanting to manage people How organizations unintentionally push strong contributors away from leadership Rethinking leadership as a choice, not an obligation Memorable Lines “Leadership used to feel like growth, now it often feels like weight.” - Amy “We tell people they should want leadership, but we don’t always tell the truth about what it requires.” - Cheryl “Not wanting leadership doesn’t mean you lack ambition.” - Amy “Support isn’t a perk, it’s the infrastructure leadership needs to survive.” - Cheryl This Week’s Gentle Challenge Take a few minutes to reflect on your own relationship with leadership: What parts of leadership appeal to you? What parts give you pause? If leadership felt more supported, more bounded, or more human, would your answer change? There’s no right response here. Curiosity is the goal. Note: This episode reflects personal experiences and cited research summaries; it’s not therapy or legal advice. For personal situations, consult a qualified professional. Connect with us Website: https://supposedtobeeasy.com/ Our Podcast Home: https://supposedtobeeasy.podbean.com/ Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy We want to hear from you! Follow and share your key takeaways, ideas, and inspiration! | 47m 51s | ||||||
| 1/28/26 | ![]() S2 Episode 47: We Thought Clearing the Space (and the Noise in Our Heads) Was Supposed to Be Easy | This episode starts with what feels like a small win—and quickly reveals why it’s anything but small. Cheryl shares the surprisingly profound experience of clearing off her desk for the first time in a long while, and how that physical shift immediately changed how her brain felt. Amy picks up the thread by introducing a personal change project she’s beginning as part of her doctoral program: an eight-week experiment in organization. Together, they explore how clutter isn’t just about “stuff,” but about habits, unfinished business, mental noise, and the weight of all the things we keep meaning to do. Amy reflects on the tension between being a collector of meaningful materials and recognizing when something no longer serves her current work or life. Cheryl offers solidarity, not expertise—sharing her own struggles with letting go of notebooks, curricula, and “just in case” resources from years past. As the conversation unfolds, the focus widens from physical space to headspace, and finally to time. What happens when we stop carrying unfinished tasks around in our minds? How much energy is lost to reminders we haven’t acted on yet? And what might shift if we dealt with the small things instead of letting them pile up—on our desks and in our thoughts? This episode marks the beginning of an eight-week shared experiment. Amy and Cheryl invite listeners to join them in choosing one habit, one space, or one pattern to gently work on—together, imperfectly, and with curiosity. Key Topics & Takeaways How physical clutter directly impacts mental clarity The difference between “new you” and new habits Why buying organizing tools isn’t the same as using them Letting go of materials tied to old roles, certifications, or identities The mental weight of unfinished business (and why it matters) Organization as a form of self-support, not self-improvement How clarity can change our experience of time—even when schedules stay full Using accountability and shared reflection to support sustainable change Memorable Lines “I physically feel less scattered in my brain because my space is a little less cluttered.” “It’s not a new me. It’s new habits.” “My space feels muffled—like a room full of people talking.” “The weight of unfinished business is very significant.” “I’m really good at creating a beautiful space. I’m terrible at keeping it that way.” A Gentle Challenge for Listeners Choose one space—a desk, a drawer, a bag, or even a digital folder—and try this: Make two piles: This has fully lived its life This might still have a purpose (I’ll decide later) Deal with one piece of unfinished business that’s been taking up mental space. Notice how it feels—not just in your space, but in your body and your thoughts. You’re invited to stick with this for the next eight weeks, checking in with yourself (and with us) along the way. Resources & References Mentioned Change management and behavior change theory Dr. Katy Milkman’s work on habit formation and change Marie Kondo’s approach to decluttering (informally referenced) Use of digital tools (including ChatGPT and search) as alternatives to holding onto physical materials Full-spectrum light therapy and the impact of winter on mood and focus | 35m 40s | ||||||
| 1/21/26 | ![]() S2 Episode 46: We’re Trying to Amplify What’s Been Working To Make Life Easier | As the calendar flips to a new year, the pressure to fix everything can feel loud and relentless. Eat better. Do more. Be better. Start fresh, again. In this episode, Amy and Cheryl slow things down and talk honestly about what it feels like to re-enter life after a break. Instead of chasing a total reset, they explore a gentler question: What if we kept the things that are already working and let them lead the way? This conversation is about resisting urgency, noticing what’s steady, and choosing intention over overhaul as we step into a new year. Key Topics & Takeaways The overwhelming “fix everything” energy that often shows up in January Why constant self-improvement can crowd out reflection and rest The difference between resetting and re-entering How small, already working habits can act as amplifiers for more Letting lived experience, not social pressure, guide next steps Permission to move into the new year without a full life overhaul Memorable Lines Amy: “It feels like everywhere you look; someone is telling you what needs to be fixed.” Cheryl: “I don’t know that I was ready to jump back in at full speed.” Amy: “Maybe we don’t need to start over maybe we need to notice what’s already holding.” Cheryl: “What if keeping what works is the work?” A Challenge for the Week Instead of asking “What do I need to change?”, try this: Name three things that are already working in your life or routines Ask yourself how you might protect or gently expand one of them Let that be enough for now No overhaul required. Additional Resources & Gentle References The concept of “re-entry” vs. “reset” after rest or time away Reflection practices that focus on continuity instead of reinvention Conversations about seasonal energy, pacing, and sustainability Connect with us Website: https://supposedtobeeasy.com/ Our Podcast Home: https://supposedtobeeasy.podbean.com/ Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy We want to hear from you! Follow and share your key takeaways, ideas, and inspiration! | 23m 33s | ||||||
| 1/14/26 | ![]() S2 Episode 45: We Thought Traveling Internationally Was Supposed to be Easy | In this episode of This Was Supposed to Be Easy, Cheryl invites Amy to finally share the story behind a “trying something new” moment she’d been dreaming about for years: Amy talks about why the country has felt like a long-time pull, what surprised her most once she arrived, and how traveling so far for the first time challenged (and affirmed) her relationship with newness, discomfort, and letting go of expectations. Along the way, the two reflect on what it means to stop waiting for something to feel “easy” before you do it—whether that’s planning a trip, pursuing a big goal, or simply giving yourself an unscheduled day to breathe. Key Topics & Takeaways Why New Zealand was a “trying something new” momentAmy shares how New Zealand has called to her since 2018, when she first encountered early childhood research connected to the country, and how that dream never fully went away. The reality of travel vs. the story we tell ourselves about itAmy admits she expected entering the country to feel intimidating, but it ended up being far simpler than she imagined, especially with English (and Māori) visible everywhere. The “getting there” part was easier than expected… the coming home part was notAmy describes the different emotional/physical experience of the long travel days and how adrenaline, planning tools, and listener tips helped. Tiny culture surprises that reminded her: you’re not in the U.S.From walking patterns in stores (left vs. right) to the surprising reality of no iced tea and very little ice, Amy shares the small moments that made the experience feel real. Expectation shifts: childcare center visits + the train ride that didn’t happenAmy talks about really wanting to visit early childhood programs, but running into practical barriers (including the inability to call local numbers). She also describes deciding not to take a 10-hour train trip for a one-hour stop and how that became a “next time” plan instead of a disappointment. Letting go of “I should be doing more”One of the biggest takeaways: giving herself permission to rest even in another country without guilt. Strengths in action: learning as a travel compassAmy notices how her “learning” strength shaped her solo days—libraries, museums, cultural experiences, and conversations with locals. Don’t wait for it to feel easy — make it possibleAmy shares a practical mindset shift: prioritize what matters by investing money, time, energy, and planning in small ways over time. Memorable Lines “New Zealand specifically… kind of calls to me.” — Amy “Don’t… wait for it to just magically happen, or feel easy.” — Cheryl “In making it possible, it felt easy on the other side.” — Amy A Challenge for the Week Choose one thing you’ve been “waiting to feel easy” before you do it and take one step to make it possible instead. Here are a few easy-to-try options (pick one): Make a tiny “future me” fund (even $5/week) for something you want to do. Cancel one subscription and redirect that money toward your goal. Spend 20 minutes researching the thing (watch one vlog, read one thread, save one article). Plan one unscheduled block of time this week,no list, no errands, no productivity pressure. Just be. Then ask yourself: What changed in my body when I stopped waiting for easy and started choosing possible? Connect with us Website: https://supposedtobeeasy.com/ Our Podcast Home: https://supposedtobeeasy.podbean.com/ Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy We want to hear from you! Follow and share your key takeaways, ideas, and inspiration! | 44m 22s | ||||||
| 1/7/26 | ![]() S2 Episode 44: We Thought Bringing in the New Year and Setting Intentions Would be Easy | It’s officially 2026, and we’re starting the year the way we love best, together. Amy and Cheryl are joined by two of our favorite returning guests, Dr. JoDell Heroux and Dr. Holly Hoffman, for a warm, funny, and unexpectedly grounding conversation about intention-setting, growth, and how we want to show up in the year ahead. This episode feels like a cozy “book club meets reflection circle,” full of laughter (including orange peels that are not pizza), gentle wisdom, and questions you can take with you into the rest of the year. Guest introduction Dr. JoDell Heroux returns with her signature blend of insight, honesty, and heart, sharing what it looks like to live in your values, make space for creativity, and reject the pressure to always be productive. Dr. Holly Hoffman brings her joyful, connection-first energy and reminds us that meaningful relationships can be found everywhere, even on a flight when you didn’t pay to pick your seats. Key topics and takeaways A question to start your year: What’s something new you want to learn or try in 2026? Creativity as care: JoDell shares how doodling became a mindfulness practice, and how giving yourself permission to create (without producing) can unlock new energy and ideas. The power of “unproductive” moments: Quiet drives, clay play, doodles, rest… and how those things can make us more connected and more present. Travel dreams and “homebody eras”: New Zealand kindness foundations, Sweden/Finland/Estonia adventures, Ireland and Scotland dreams, and the very real joy of staying home with your dogs. Reflection across the year: What are you proud of from 2025, and what do you hope you’ll be proud of when 2026 ends? Values in action: Living in alignment with your core values can create contentment, clarity, and a deeper sense of balance. How do you want others to feel after interacting with you? The group shares intentions like valued, important, authentic, and truly connected. Memorable lines (quotes) “The more we take time to be what we would consider unproductive, the more productive we end up being.”-JoDell “I want people to feel valued… like their time, their brilliance, their person was valued.”- JoDell “I want them to know that they’re important… their ideas, their presence is important.”- Holly “Somebody in my presence would feel like they could be exactly who they are, and that that’s okay.”- Amy “How can I bring time back in and offer it to others?”- Cheryl A challenge for the week Pick one question from this episode and write your answer down, no overthinking, just honesty. Try one of these: What’s something new you want to learn or try this year? Where is somewhere new (or different) you’d like to go, or how do you want to experience “home” differently? What do you want to be proud of when this year ends? How do you want people to feel after interacting with you? Bonus: share your answer with someone you trust, or with us. Connect with us Website: https://supposedtobeeasy.com/ Our Podcast Home: https://supposedtobeeasy.podbean.com/ Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy Stay curious, stay connected, and keep wondering. | 39m 47s | ||||||
| 12/31/25 | ![]() S2 Episode 43: We Want Wintering and Setting Intentions to be Easy (Part 2) | As we close out 2025, Amy & Cheryl invite listeners into a gentler way of approaching the new year—one rooted in wintering, reflection, and intention rather than pressure-filled resolutions. Building on last week’s conversation, this episode explores how tools like bingo cards, vision boards, wishes, and “words of the year” can help us move forward without urgency or all-or-nothing thinking. Through stories of seeds, silence, family life, and personal growth, Amy and Cheryl offer permission to slow down, tend to what matters, and trust that even quiet movement is still meaningful progress. Key Topics & Takeaways Why traditional New Year’s resolutions often create pressure, guilt, and burnout The concept of wintering as a season for reflection, rest, and gentle dreaming Using bingo cards, vision boards, or wishes as flexible intention-setting tools How breaking goals into “baby steps” can support motivation and self-compassion Letting intentions stay open-ended so they can grow in unexpected ways Challenging all-or-nothing thinking (full wins, half wins, and hearts count too) Creating categories for intentions (rest, relationships, personal growth, energy) The importance of curiosity when comparing how others approach goals Making space for quiet—silence, slowness, and reflection—as a form of care Moving forward without speed, urgency, or a perfect master plan Memorable Lines & Quotes “Moving forward doesn’t have to be fast to be meaningful.” “Permission to be human gives us permission to show up less than perfect.” “What if we thought about direction without the speed… yet?” “It doesn’t have to be all or nothing—sometimes it’s a half-heart.” “Wintering invites us to tend, not push.” “Slower movement is still movement.” “There have to be seasons where it’s not about becoming more, but becoming truer.” “You don’t have to do everything right now.” “What do I want to nurture and offer care and attention to?” Resources & Episodes Mentioned Episode 42 – Wintering, Rest, and Reflection Referenced multiple times as the foundation for this continued conversation VIA Character Strengths Assessment Discussed in relation to love, learning, wisdom, and shifting priorities Intention-Setting Tools Referenced Bingo cards (annual or seasonal) Vision boards Wishes rituals Word of the Year practices Upcoming Resources Watch our social media for additional details on categories of rest will be shared via social media and the website | 25m 44s | ||||||
| 12/24/25 | ![]() S2 Episode 42: We Think Wintering Should be Easy (Part 1) | As the year winds down, Amy and Cheryl explore the idea of wintering, not just as a season, but as a necessary pause. In this first part of a two-part conversation, they reflect on rest, unfinished goals, shifting intentions, and the tension between wanting to slow down and still having responsibilities. This episode is about giving yourself permission to rest, reflect, and soften before deciding what comes next. Key Topics & Takeaways What “wintering” means beyond cozy aesthetics The pull between hibernation and ongoing responsibilities Reflecting on goals without labeling them as success or failure Why bingo cards allow for reflection that SMART goals sometimes don’t How intentions can shift as life unfolds The importance of rest in creating space for clarity and future direction Different types of rest and how to identify what you need right now Letting go of internal criticism and practicing grace during reflection Memorable Lines Amy: “Creating some time and some space to not have to produce as much.” Cheryl: “You don’t know what you don’t know.” Amy: “I don’t think I failed. I think I reprioritized my time, effort, energy, and resources. Amy: “When I rest, it gives my brain the space to reflect.” This Week’s Gentle Challenge As you listen, ask yourself: What type of rest do I need right now? Is it: Intellectual rest Emotional rest Sensory rest Social rest Physical rest Spiritual rest Mental rest Choose one area and give yourself permission to lean into it, without guilt, productivity pressure, or needing it to lead somewhere yet. We will be posting ideas for each on our Social Media and website! Additional Resources Wintering: The Power of Rest and Retreat in Difficult Times by Katherine May Making Winter: A Hygge-Inspired Guide to Surviving the Winter Months by Emma Mitchell Atomic Habits by James Clear Connect with us Website: https://supposedtobeeasy.com/ Our Podcast Home: https://supposedtobeeasy.podbean.com/ Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy We want to hear from you! Follow and share your key takeaways, ideas, and inspiration! | 30m 56s | ||||||
| 12/17/25 | ![]() S2 Episode 41: We Thought Listening to Holiday Music Was Supposed to be Easy | Holiday music has a way of time-traveling us straight into our favorite memories, whether it’s vinyl spinning in the living room, singing in the car on a long road trip, or turning decorating day into an event. In this episode, Amy and Cheryl talk about the songs that shaped their holiday seasons, the “rules” about when it’s acceptable to start listening, and how music helps us create memories that stick. Plus: holiday concerts, cozy movies, and a listener invitation to help us build the ultimate winter-holiday playlist. Key topics and takeaways Why holiday music is so powerful: it connects to our senses and makes memories more vivid (and more retrievable later). Nostalgia playlists: childhood albums, record players, and the songs that instantly bring you back. When is it “allowed” to start holiday music? November 1st, day-after-Thanksgiving traditions… and yes, even August (no judgment… mostly). Holiday decorating as a whole experience: music, rituals, themed trees, and making the work feel worth it. The “new music vs. traditions” debate: keeping favorites sacred while still letting new songs earn a place in your holiday story. Holiday concerts & events: Nutcracker, orchestral shows, jazzy Christmas, Mannheim Steamroller, and dream events like Trans-Siberian Orchestra and candlelight concerts. Holiday movies as mood-setters: from classics like Elf and Home Alone to cozy, predictable Hallmark/streaming movies you can wrap gifts too. Songs you love… and songs you cannot: the funny (and emotional) stories behind the “skip it immediately” list. Listener invitation: share your favorite winter-holiday songs, especially from holidays and traditions beyond the ones Amy and Cheryl grew up with, so we can build a community playlist. Memorable lines “One of my favorite things about the holidays… is music.”- Amy “What makes Christmas special to me is that it’s a finite amount of time.”- Amy “We are saturated in Christmas music.”- Amy “It’s important to me to be in that top 0.5% of listeners…”- Cheryl “You’re not watching it because you’re like, ‘What’s gonna happen next?’ You’re watching it because it’s sweet and mindless.”- Amy “Those times that our senses are engaged, those are those moments when we might remember a moment.” - Cheryl “I would love for our listeners to share some of their favorites.” - Cheryl A challenge for the week Pick one memory you want to strengthen this season and pair it with a song on purpose. Choose a “signature song” for decorating, baking, driving, or wrapping gifts. Play it every time you do that activity. Notice how quickly your brain starts linking the music with the feeling. Bonus: add one new-to-you holiday song to your rotation and see if it earns a permanent spot. Additional resources or links The Art of Making Memories (book mentioned by Cheryl) We’ll be creating a Winter Holiday Playlist, and we want your favorites! Connect with us Website: https://supposedtobeeasy.com/ Our Podcast Home: https://supposedtobeeasy.podbean.com/ Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy We want to hear from you! Follow and share your key takeaways, ideas, and inspiration! | 36m 25s | ||||||
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