This Was Supposed to be Easy Podcast

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...

Amy and Cheryl say yes to a “hen party” weekend that turns into glamping-in-domes magic in northern Michigan. What starts as “are we really camping?” becomes a masterclass in trying new things the comfy way, surrounded by friends, thoughtful details, and just enough nostalgia to spark joy. Together they unpack how environment, company, and baby steps can make new experiences feel safe, meaningful,...

We thought nice would be easy… but it turns out kind is braver. In this conversation with Swedish play advocate Suzanne Axelsson, we unpack why “niceness” can be a hollow performance while kindness is a courageous practice rooted in empathy, listening, and community. We explore how adults and children learn the skills underneath kindness (self‑regulation, curiosity, patience), and how play creates...

In this episode, Amy and Cheryl dig into the messy, often misunderstood, and absolutely necessary practice of delegation. From laundry lessons to grading papers to letting AI pick up some of the load, they explore the ways we resist delegation, the excuses we use, and how learning to let go can bring freedom, growth, and even joy – and it’s NOT cheating! Highlights Why women, in particular, often...

Season 2 is here! We tried something new – this podcast – and we did it! Amy and Cheryl set the tone for another year of trying new things—big and small—while keeping our “permission to be human (and messy)” vibe. From first-time international travel to experimenting with edible flowers and dreams of glassblowing, forest bathing, mocktail making, and maybe even sea kayaking, we invite listeners to...

We did it - 25 episodes, 21 Wednesdays in a row (Week 1 we launched 4)! In this special season finale, Amy and Cheryl reflect on what it means to wrap up Season One of This Was Supposed to Be Easy. From family adventures and Broadway moments to pumpkin bread, golf cart confessions, and everything in between, this episode is part celebration, part reflection, and part look ahead. In this episode, y...

Amy and Cheryl are back, and this week we’re tackling the mythical creature that is…the never-ending to-do list. You know the one the list that magically grows every time you cross something off. From summer chaos and office clutter to misplaced microphones and the myth of “when things slow down,” we’re sharing the real-life mess behind our own lists (and laughing along the way). We’re diving into...

Following our two-part deep dive into finances with Jeremy Bond, we’re shifting gears to get real about credit cards, the good, the bad, and the lessons learned along the way. In this candid conversation, Amy and Cheryl open up about their first experiences with credit, the cultural pull of “cool” store cards, and the pitfalls that come with not understanding interest rates or payment schedules. T...

In Part 2 of our conversation with Dr. Jeremy Bond, we dig even deeper into real-world money habits,  from splitting raises between “today you” and “future you” to creating simple systems that keep saving automatic. Jeremy shares candid stories from his own financial missteps (hello, Jaguar!) and how those experiences shaped his perspective on debt, lifestyle creep, and building true financial ind...

Money talk can feel overwhelming and let’s be honest, most of us didn’t grow up having open conversations about it. In this episode, Amy and Cheryl bring on their first-ever male guest (and Amy’s husband!), Dr. Jeremy Bond, to help break down what personal finance actually looks like in real life. Jeremy shares how our early experiences shape the way we think about money, why “wealth” isn’t always...

In this reflective and engaging midyear episode, Amy and Cheryl invite listeners to pause and check in on their intentions, goals, and growth in 2025 so far. Rather than pushing productivity or grinding toward unrealistic timelines, they approach the idea of goal setting with gentleness, curiosity, and joy. Through the lens of their personal “Bingo cards,” they unpack what’s working, what needs to...

In this caring and introspective episode, Amy and Cheryl dive into a conversation about guilt, specifically how it manifests in the lives of women. They explore the internal and external pressures that make women feel like they need to constantly “do more,” and they challenge the cultural norms that glorify busyness while devaluing rest. The conversation unfolds around themes like: Feeling guilty...

In this heart-to-heart episode of This Was Supposed to Be Easy, Amy and Cheryl open up about the winding, sometimes bumpy journey of confidence at different stages of life. From the myth that confidence simply comes with age to the surprising moments that can shake it, they explore where confidence shows up, where it wobbles, and how curiosity, courage, and micro-wins help us grow along the way. W...