This Was Supposed to be Easy Podcast

Making friends as an adult isn't always easy. And keeping those friendships? Sometimes that's even harder! As our lives change, so do our relationships, our priorities, and the ways we connect. This week, Amy and Cheryl revisit one of the conversations that inspired This Was Supposed to Be Easy in the first place: friendship. From loneliness and shifting social circles to Myrtle Beach adventures and the importance of having a friend who will talk to absolutely anyone, they're exploring why friendship takes intention at every age.

What happens when friendships fade, when life takes us in different directions, or when we simply wish we had someone to call for dinner? With laughter, personal stories, and practical ideas for finding connection, Amy and Cheryl remind us that friendships don't have to stay the same to be meaningful - and that finding your people might begin with trying something new, volunteering, or simply being brave enough to say hello.

This Week's Challenge: Think about where you find yourself laughing, feeling connected, or genuinely enjoying the company of others. What's one small thing you could do this week to create more of those moments?

Some people like Broadway. Taylor Priest has seen 281 performances, keeps a color-coded spreadsheet of every show, has Playbills covering four walls, travels across the country to catch favorite performers, and never leaves home without her emergency “purse Sharpie.” So yes, we invited her on the podcast.

But this conversation isn't really just about Broadway. It's about the joy of having a thing - something you love enough to follow, learn everything about, make spontaneous trips for, and share with the people around you. Taylor joins us to talk Mamma Mia! (all 20 times), stage doors and Tony Awards, favorite performers, secret show trips, our “secret society of showgoers,” and why sometimes the best part of loving something is watching someone else discover it for the first time.

This Week's Challenge:

Have you ever walked out of a conversation thinking one thing - only to discover the person beside you heard something completely different?

Same words. Same room. Completely different story.

In this episode, Cheryl and Amy unpack why our brains don’t simply record what happens. We filter conversations through our past experiences, expectations, relationships, and even what we expect to see or hear. From red playing cards and moonwalking bears to creepy (or delightful!) ice cream trucks, they explore just how differently two people can experience the exact same thing.

They also talk about what to do when those differences actually matter: assume positive intent, get curious about the story your brain is telling you, ask “What did you mean?”, reflect back what you think you heard, and recognize when it’s important to say, “Wait—that’s not what I said.”

And sometimes? Maybe you just let the fried rice go (iykyk).

A question to carry with you:

🎧 Listen in, then come find us on social and tell us: What helps you when you and someone else walk away from the same conversation with two completely different versions of what happened?

Disappointment is one of those feelings we all experience, and one we're surprisingly quick to talk ourselves (or someone else) out of.

This week, Amy and Cheryl talk about what happens when reality doesn't match what we pictured: the birthday that didn't feel like the milestone we imagined, the plans that fell apart, the things we wish we'd done differently, and those moments when we're disappointed in ourselves. What if, before looking for the silver lining or rushing to fix things, we simply gave ourselves permission to admit: I'm disappointed.

They also explore what it means to sit with someone else's disappointment without trying to make it better, why two conflicting feelings can both be true, and how to move from disappointment toward learning, grace, and whatever comes next.

The takeaway: You don't have to live in disappointment—but you are allowed to visit. Feel it. Get curious about what you were hoping for. Decide whether there's something to learn, repair, or release. And then, when you're ready, move forward.

This week's invitation: Think about a disappointment you've been carrying. Is there something you need to acknowledge, something you can learn, an amends you need to make—or something you're finally ready to put to rest?

What makes some gatherings leave us feeling energized, connected, and glad we came while others just feel like another thing on the calendar?

Inspired by Priya Parker’s The Art of Gathering, Amy and Cheryl explore what changes when we stop thinking only about what we’re planning and start asking why we’re bringing people together in the first place. From dinner with friends and family celebrations to conferences, retreats, meetings, and travel experiences, they talk about the small choices that can completely change how people experience being together.

Along the way, they dig into the energy of a space, why a gathering begins long before anyone arrives, the surprisingly important things people want to know ahead of time (yes, including food, parking, and what everyone is wearing), and how thoughtful hosts create the conditions for people to feel comfortable enough to actually connect.

Takeaway:

This week:

What turns an ordinary cup of coffee into something you look forward to? Why does Sunday dinner feel different from simply eating dinner? And why are there certain little things we do with family, friends, or coworkers that we would genuinely miss if they disappeared?

In this episode, Amy and Cheryl explore the power of rituals—the repeated moments that carry meaning and help ground us in our lives. From morning coffee and quiet time to family dinners, workplace celebrations, candles, birthday meals, and even the annual Nelson Week T-shirt reveal, they talk about the difference between a routine, a tradition, and a ritual—and how intentionality can transform something ordinary into something meaningful.

They also explore why rituals can create connection and belonging within families, friendships, and workplaces—and why the best shared rituals aren't simply another obligation. Sometimes the moments that matter most are the ones we collectively decide are worth doing again. 

As we move into fall and toward the winter months, take a look at the rituals already woven into your life. Which ones bring you joy? Which ones help you feel connected or grounded? And which ordinary routine might become something more meaningful if you approached it with a little more intention?

What makes someone more than a favorite singer or celebrity? In this special episode, Amy and Cheryl are joined by friends Holly Hoffman and Kim Davidson for a conversation about why Dolly Parton became something more - a source of joy, possibility, generosity, and, of course, plenty of sparkle.

There are Dolly wigs (yes, on an audio podcast), concert tickets that definitely blew the budget, Dollywood memories, records, chip clips, an emotional-support Dolly, favorite songs, and lots of laughter. But the conversation also goes deeper into the Dolly behind the rhinestones: the storyteller, businesswoman, philanthropist, proud Appalachian, champion of children and books, and woman who seemed determined to use what she had to make life a little better for someone else. The group reflects on Dolly's extraordinary Imagination Library legacy, including a contribution from Dr. Chad Waldron, and on what all of us might learn from the way Dolly chose joy, stayed true to herself, and gave back.

Because maybe the best way to describe Dolly's legacy is also the simplest: the world is a little better because Dolly Parton was in it.

There’s something about the shift into fall that just feels different. The sweaters come back out, favorite drinks taste better, the leaves start changing, and suddenly there are little things everywhere to look forward to. In this episode, we’re talking about the sights, smells, tastes, traditions, and plans that make us excited to welcome the “-ber” months.

But maybe our love of fall is about more than pumpkin spice and cozy blankets. A changing season can also bring that feeling of a fresh start—a chance to reset, notice what we’re anticipating, and decide how we want to experience the months ahead. Because January doesn’t get to have all the fresh-start energy.

This Week’s Challenge

Choose one thing you want to look forward to this fall and put it on your calendar. It can be as simple as a walk through the changing leaves, a favorite fall drink, a cozy movie night, a trip to the pumpkin farm, or trying something completely new. Give yourself something to anticipate—and then make sure you actually do it.

Season 3 is here—and we're starting with a question: What do you want to be new at?

We're talking about trying things without needing to master them, letting curiosity lead the way, and remembering that growth doesn't always mean doing more or becoming better. Sometimes it's about play, discovery, a little bit of awe—and continuing to become more fully who we already are.

Takeaway

Try This This Week

And as we begin Season 3, we want to hear from you. What are you curious about? What do you want to try? What conversations do you want to be part of? This season, we're making more room for your stories, your questions, and this community we're building together.

Guest Links:

This Was Supposed to Be Easy

What exactly happens at a writing retreat?

There were moments when we would look at the clock and realize several hours had passed. We were working, talking, researching, writing, building databases, sharing ideas, eating, laughing, taking breaks, and then diving right back in. Staying immersed in the work gave ideas time to connect and conversations time to develop. And that opened the conversation even further, because this idea can extend far beyond academic

Maybe you work remotely with a team and would benefit from protected collaborative work time. Maybe you have a creative project you want to give more attention. Maybe you want to paint, scrapbook, journal, read, organize your family photos, work on a grant, finish a report, plan something new, or finally move forward on the project that has been sitting on your list for months. A retreat creates intentional space for something you value. Holly also reminds us of the power of the social experience. Talking, laughing, sharing ideas, checking in, and encouraging one another can build momentum. Working alongside people who care about the work and care about you can create energy that carries the project further.

Want to Try It?