This Was Supposed to be Easy Podcast

We Thought Traveling Abroad and Feeling Connected to your Ancestors Was Supposed to Be Easy Episode Description What happens when a lifelong dream finally becomes reality? In this 2 part episode, Amy sits down with Cheryl to unpack her May 2026 adventure through Sweden, Finland, and Estonia. As someone who has spent years reading about Nordic culture, hygge, cozy living, and her own Nordic roots,...

Episode Description What happens when a lifelong dream finally becomes reality? In this 2 part episode, Amy sits down with Cheryl to unpack her May 2026 adventure through Sweden, Finland, and Estonia. As someone who has spent years reading about Nordic culture, hygge, cozy living, and her own Nordic roots, Cheryl shares what it was like to finally experience these places firsthand. From Swedish me...

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 d...

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...

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 mis...

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. Th...

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 pro...

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 relatab...

In this episode of This Was Supposed to Be Easy, Amy and Cheryl are joined by special guest Ranee Conley for a heartfelt and thought-provoking book club-style conversation about The Midnight Library authored by Matt Haig. What begins as a casual discussion quickly unfolds into a deeper exploration of life’s choices, regrets, wishes, purpose, and the stories we tell ourselves about “what could have...

In this episode of This Was Supposed to Be Easy, Amy and Cheryl dive into a thoughtful and relatable conversation about books, reading, and the way stories shape connection. What starts as a simple reflection on shared reading habits unfolds into something deeper, how books become bridges between people, spark meaningful conversations, and open doors to new perspectives. Whether you’re an avid rea...

In this episode, Cheryl and Amy welcome guest Casey Sterle for a conversation that feels both deeply personal and incredibly relatable - parenting, but through the lens of joy. Casey begins by sharing her story as both a longtime educator and a mother of four, offering a perspective shaped by decades of working with children and raising them across many stages of life. From early childhood through...

What happens when a fiction book opens the door to a very real conversation about time, memory, connection, and the lives we’re living right now? In this episode, Amy and Cheryl start by talking about The Seven Year Slip and quickly find themselves reflecting on something much bigger: how strangely time can feel, especially in the years since the pandemic. They explore how easily we lose track of...

When was the last time you truly paused to celebrate something you did? Not brushed past it. Not minimized it. Not immediately moved on to the next thing—but actually let it land. In this episode, Cheryl and Amy explore something that felt surprisingly hard to answer in real time: why we struggle to celebrate our own accomplishments. Through personal stories—from milestone birthday trips to promot...

In this episode, Amy turns the microphone toward Cheryl to reflect on her most recent study abroad trip to Reggio Emilia, Italy—a place known around the world for its innovative approach to early childhood education. But this conversation goes far beyond travel stories. Instead, Amy invites Cheryl to unpack what it really means to design and lead a meaningful travel experience for others. Cheryl s...

Sometimes the hardest part of friendship isn’t love or intention, it’s simply finding the time. In this week’s episode, Amy and Cheryl reflect on a recent gathering with their long-time book club friends. What started as a simple plan to reconnect turned into a deeper conversation about how difficult it can be to get everyone together as life becomes busier and schedules become more complicated. T...

Saying “no” sounds simple in theory, but in real life, it can be anything but easy. In this episode, Amy and Cheryl explore what happens when we set a boundary and the other person doesn’t listen. Why do some people treat “no” like it’s negotiable? When does persistence cross the line into pressure? And how do we stay grounded in our boundaries without damaging relationships? Through personal stor...

What happens when you want to say yes… but your body, your calendar, and your capacity are quietly begging for no?   In this episode, we explore the complicated practice of saying “no” — especially when the invitation is meaningful, the people matter, and part of us truly wants to say yes. What happens when our desire and our capacity don’t match? When we can technically make it work… but at a cos...

Episode 50 feels a little like a birthday, not brand new, not frantic, but grounded in everything we’ve lived and learned along the way. In this milestone episode of This Was Supposed to Be Easy, Amy and Cheryl pause to reflect on what 50 conversations have taught them about connection, joy, growth, confidence, listening, and honoring the seasons of our lives. What started as an idea that felt “su...

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 o...

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...

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 e...

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...

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 lettin...

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...

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. T...