This Was Supposed to be Easy Podcast

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 bec...

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...

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...

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 a...

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 “mar...

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-C...

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-w...

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 ...

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 o...

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 r...

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...

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 c...

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 stic...

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 ...

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.

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