This Was Supposed to be Easy Podcast

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...

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...

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 tha...

This Was Supposed to Be Easy with Amy & Cheryl The holidays are supposed to feel magical, connected, and full of ease, but often they come with pressure, unspoken expectations, emotional landmines, and complicated relationships. In this episode, Amy and Cheryl take a heartfelt and humorous look at psychological safety during the holiday season and all the ways it can be challenged. They unpack...

In this “oh no I do that” conversation, Amy and Cheryl explore the complicated emotions wrapped up in something that should be simple: giving a gift. From the meaning we attach to presents, to the anxiety of letting go once the gift leaves our hands, this episode dives into the psychology behind generosity, expectations, and the stories we create around what a gift “should” mean. With personal ane...

In this creative episode, Cheryl and Amy explore the idea of thankfulness as a lifestyle and how gratitude becomes even more powerful when shared in community. Together, they dive into playful, accessible, and joy-filled ways to gamify gratitude—from gratitude walks to Pictionary, paper chains, pottery, and meaningful group activities that spark connection. Whether you're looking to deepen your ow...

When the calendar starts bossing you around, joy taps out, so Amy and Cheryl share how they took it back: trading obligation math for memory-making, flexing dates, and building traditions that actually fit real life. Key topics & takeaways Why “the day on the calendar” doesn’t have to rule your plans Swapping obligation for flexibility (and sanity) Thanksgiving reimagined: restaurants, leftove...

Episode description Fresh off a “Joyful Leadership” workshop, Amy and Cheryl dig into the quiet engine behind joy and happiness: trust. They unpack how trust (or the lack of it) shows up at work, in partnerships, parenting, even in how we talk to ourselves. Expect real stats, relatable stories (hello, micromanaging), and practical ways to build, rebuild, and protect trust without burning out. Key...

Listener requests for real-life parenting topics led us to a candid conversation with Shannon, a newly divorced mom navigating co-/parallel-parenting with firm boundaries, smart tools, and a lot of self-work. From rewriting a custody agreement and using a parenting app, to protecting her peace (and her daughter’s), Shannon shares what helped, what she’d do again, and what she wishes she’d known so...

In this cozy, laughter-sprinkled episode, Amy and Cheryl kick off with weekend stories from Myrtle Beach and Mackinac Island, then dive into why our brains notice what we tell them to notice. Cheryl introduces the Reticular Activating System (RAS), the brain’s sensory filter, and the two explore practical ways to “train” it toward noticing the good and fueling joy without slipping into toxic posit...

Guest note: Our guest requested anonymity. We refer to them as Lee throughout. Episode Description In Part 2 of our dating series, Amy and Cheryl continue our sit down with Lee, a therapist and widow, who takes us behind the scenes of midlife online dating: the hope, the gut checks, and hard boundaries. We talk about AI-polished profiles, spotting scams, healing after heartbreak, and what it looks...

Guest note: Our guest requested anonymity. We refer to them as Lee throughout. Episode description In this warm, funny, and deeply honest conversation, Amy and Cheryl sit down with Lee to unpack what it’s really like to re-enter the dating world in midlife, after losing a spouse. From grief and menopause to algorithms and questionable selfies, Lee shares the highs, lows, and laugh‑out‑loud moments...

In Part Two of our listening series, Amy and Cheryl move from awareness to action. Building on Part One, they explore Stephen Covey’s levels of listening, how “pauses” create space for understanding, and four practical tools pausing, reflecting, reading nonverbals, and asking better questions that transform everyday conversations at home, at work, and with kids. Expect laughs (Grandma’s “selective...

Listening sounds simple, but as Amy and Cheryl discover in this two-part series, it’s one of the most misunderstood, and underdeveloped, skills we carry into our families, friendships, and workplaces. In Part One, the conversation dives into the culture of listening we inherit, the distractions that keep us from being present, and the surprising ways we confuse “hearing” with truly listening. Thro...