This Was Supposed to be Easy Podcast

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 relatable, laugh-out-loud stories, from store hopping for a single item, to international hotel mishaps, to crafting projects gone sideways, they explore why “easy” isn’t always easy.
More importantly, they invite you to reframe those moments: What if these frustrating experiences are actually the stories we’ll laugh about later? What if they’re what make us more interesting, more connected, and a little more human?
 
Key Topics & Takeaways
The myth of “quick and easy” tasks, and why they often expand
“Give a mouse a cookie” moments that derail our time
The internal debate: call vs. text vs. email (and when none of them work!)
When systems should be easy… but absolutely aren’t (hello, cancellations and subscriptions)
The hidden cost of DIY: time, energy, and frustration
Finding humor in everyday inconveniences
Reframing frustration into connection and storytelling
The power of asking: What’s the hack?
 
 Memorable Lines
“I thought this would take 10 minutes… and suddenly it’s half my day.” - Amy
“There is no true sound method to that madness at all.” - Cheryl
“You must do the thing you hate.” - Amy
“It should have been easy… but it kept revisiting me.” - Cheryl
“It is never going to be simpler if I make it myself.” — Amy
Try This: Challenge for the Week
Think about one thing this week that should have been easy but wasn’t.
Then reflect:
What made it harder than expected?
Is there a “hack” you discovered (or could try next time)?
How might this become a story you laugh about later?
Bonus: Share your story with someone, you might be surprised how quickly it turns into connection.
 
 Additional Resources
 “100 Bad Days” by AJR
Reflect on your own “this was supposed to be easy” moments as journaling prompts
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy
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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 been.”
Together, they reflect on how perspective shapes our experiences, why some paths feel meaningful while others fall flat, and how even our smallest decisions can ripple into unexpected outcomes. This episode invites listeners to pause, reflect, and consider what it really means to live a life that feels like your own.
 
Guest Introduction
This episode features Ranee Conley, a friend and colleague who brings both personal insight and deep reflection to the conversation. Ranee shares how this book impacted her in unexpected ways and sparked meaningful self-awareness around blame, perspective, and purpose.
 
Key Topics & Takeaways
The idea that every choice creates a different version of our life, and we don’t always see the full picture of those paths
How perspective shapes whether we see something as loss, growth, or simply a part of the journey
The difference between living for ourselves vs. living to meet others’ expectations
Why even the “perfect” life might not feel fulfilling without the lived experience behind it
The emotional weight of “what if” thinking and how the book challenges that narrative
Letting go of unnecessary blame and self-judgment (sometimes things were always going to unfold the way they did)
The importance of ordinary moments and intentional living, not just big life decisions
Reframing success and timelines because there’s no “too late” when something still matters to you
The realization that growth often comes from fully living one path, not constantly searching for or imagining a better one
 
Memorable Lines
“You only know what you know.” – Amy
“Why do I think I know better than someone else about their own life?” – Amy
“Do I want to do something intentional or am I going to jump back on the hamster wheel?” – Cheryl
“Acceptance isn’t giving up.” – Ranee
“You can’t skip the journey and feel right about where you land.” – Cheryl
 
Challenge for the Week
Take a moment to reflect on your own life, not the big, dramatic “what ifs,” but the smaller, everyday choices.
Where might you be holding onto unnecessary blame?
Are you living in alignment with what you truly value… or what you think you should value?
What is one small, intentional choice you could make this week that feels more like you?
 
Additional Resources
The Midnight Library by Matt Haig
Note: This episode reflects personal experiences and the opinions of the talent, it’s not therapy or legal advice. For personal situations, consult a qualified professional.
Connect with us
Website: https://supposedtobeeasy.com/
Our Podcast Home: https://supposedtobeeasy.podbean.com/
Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy
We want to hear from you! Follow and share your key takeaways, ideas, and inspiration!

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 reader or someone who “means to read more,” this episode invites you to reflect on how the stories you engage with influence your thinking, your relationships, and even your sense of self.
 
 Key Topics & Takeaways
Reading as a shared experience, even when you don’t read the same books
How curiosity about someone else’s reading can deepen connection
The idea that “reading” includes audiobooks and different formats
Books as conversation starters and relationship builders
The role of storytelling in expanding perspective and empathy
Why it might be time to bring book conversations into the podcast
 
 Memorable Lines
“One of the things we often talk about when we’re on our car rides… are the books that we’re reading or listening to.”
“You’ve read a book that makes me very curious, and so I read it…”
 
 A Challenge for the Week
Think about the last book (or audiobook) that stayed with you.
Now ask yourself:
Who could I share this with?
What conversation might it spark?
Take it one step further, recommend it to a friend, or ask someone what they’re currently reading and get curious about their answer.
 
Additional Resources
Consider starting a shared reading list with a friend or colleague
Have you tried the Goodreads app? It helps track your books and lets you share your reading list with friends!
Try alternating book recommendations with someone in your life
Explore audiobooks if you’re short on time but still want to engage with ideas
 
Ways to Connect
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy

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 middle school and beyond, she reflects on what it means to parent in real time - often feeling like you’ve figured something out, only to realize each child brings a completely new experience.
What stands out most in this conversation is Casey’s honest and refreshing perspective: parenting has been more joyful than she was led to believe. While she acknowledges the very real challenges - responsibility, exhaustion, and the weight of raising humans - she shares how laughter has become a central thread in her family life.
Together, they also touch on bigger ideas - how we look for the good in our lives, how joy can coexist with hardship, and how what we carry from our past (even generationally) shapes what we pass forward.
This episode is both a permission slip and a gentle reminder: even in the messiness of parenting, there is so much to laugh about - and that laughter matters.
Key Topics & Takeaways
Parenting can be more joyful than we expect, even alongside its challenges.
Laughter plays a powerful role in helping families navigate hard moments and build connection.
Each child and each stage of parenting brings something new, there’s no one-size-fits-all approach.
If we actively look for joy, we’re more likely to find it in everyday moments.
Joy and hardship can coexist - parenting is both deeply challenging and deeply meaningful.
Creating space for humor and lightness can support resilience for both parents and children.
What we carry from past generations includes not only hardship, but also resilience, laughter, and joy.
Memorable Lines
“I didn’t know how much I would laugh.”
“You might have figured it out for one… but it’s going to be different for the next.”
“If you look for joy, you’ll find it.”
“The world is a hard place… but we’ve got to keep finding the joy.”
“We laugh all the time - even when we maybe shouldn’t.”
 
Challenge for the Week
This week, try becoming someone who intentionally notices joy in your everyday life - especially in the middle of routines, chaos, or stress.
Pay attention to one moment each day that makes you laugh (or almost laugh)
Write it down, share it, or simply pause and let it land
If you’re parenting (or working with children), notice what happens when you lean into the humor instead of rushing past it
And a gentle question to carry with you:
What if joy isn’t something I have to wait for… but something I can practice noticing?
Note: This episode reflects personal experiences and the opinions of the talent, it’s not therapy or legal advice. For personal situations, consult a qualified professional.
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy
We want to hear from you! Follow and share your key takeaways, ideas, and inspiration!

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 where our time actually goes, how our perception of time shifts as we get older, and why quality time matters more than we sometimes realize.
From parenting milestones and doctoral coursework to scrolling, distraction, and flow, this conversation is a thoughtful reminder that while we can’t manage time itself, we can pay closer attention to how we use it.
Key Topics and Takeaways
How The Seven Year Slip sparked a deeper conversation about time and personal growth
Why the years since COVID can feel blurred, distorted, or hard to place
The difference between the person you were seven years ago and the person you are today
How children’s milestones can make the passing of time feel especially visible
The idea that we cannot actually manage time, but we can manage our use of time and our energy
Why tracking time can reveal surprising gaps between what we think we do and what we actually do
How distraction, phones, and multitasking can quietly steal connection
The role of quality time in relationships and why it matters so much
How flow can make time disappear in the best possible way
Why this might be the right moment to think more intentionally about who you want to become and how you want to spend your life getting there
Memorable Lines
Amy Bond: “It just had me thinking a lot about time as kind of a construct.”
Cheryl Priest: “You can’t manage time because time is constant.”
Cheryl Priest: “What you can manage is your use of time.”
Cheryl Priest: “I was not using the time in the way that I wanted to use the time, and I got caught.”
Challenge for the Week
Try a simple time-awareness experiment.
At the start of the week, write down how you think you spend your time. Include work, errands, family time, scrolling, rest, hobbies, and anything else that fills your days.
Then, for one full week, track how you actually spend your time in real time or at the end of each day.
As you compare the two, ask yourself:
Where is my time really going?
Where do I feel most energized?
Where do I feel disconnected?
Am I spending quality time on what matters most to me?
What is one small shift I want to make next week?
Additional Resources or Links
The Seven Year Slip by Ashley Poston
The idea of flow and how deep focus changes our experience of time
Reflection tools like weekly planners or time-tracking printables to better understand your rhythms and habits
Ways to Connect
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy

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 promotions, to simply finishing a semester—they uncover how often we skip over meaningful moments without acknowledgment.
The conversation gently unpacks the deeper reasons behind this pattern: the pressure of timelines, the fear of appearing boastful, the habit of deflecting praise, and the tendency to keep moving the goalpost instead of pausing to recognize progress.
Together, they reframe celebration as something much more accessible and necessary—not just reserved for life’s biggest milestones, but available in everyday wins, effort, and follow-through. They explore how celebration can fuel motivation, reinforce identity, and bring more joy into daily life.
This episode is an invitation to slow down, notice what you’ve done, and practice something that may feel unfamiliar—but deeply important: celebrating yourself.
 
Key Topics & Takeaways
Many of us struggle to name our own recent celebrations—we move quickly to what’s next instead.
Celebration often feels tied to an unspoken timeline, and if we miss it, we assume the moment has passed.
There can be a fear that celebrating ourselves will come across as bragging or being “too much.”
We frequently deflect praise, minimizing our accomplishments instead of receiving them.
Moving the goalpost keeps us from acknowledging progress—we wait for the “big” moment, then skip past it.
Celebration doesn’t have to be big—small wins, effort, and progress deserve recognition too.
Celebrating along the way can fuel motivation, reinforce identity, and support follow-through.
Accepting and modeling celebration helps others feel permission to share and celebrate their own wins.
 
Memorable Lines
“When was the last time you actually let it land?”
“We move right on to the very next thing.”
“Does missing the moment mean it doesn’t count?”
“Every step you take is worthy.”
“We move the goalpost and forget to pause.”
“Celebrate yourself like you would celebrate a friend.”
“Celebration can be fuel.”
“Let me just sit with this for a second.”
Challenge for the Week
Think about something you didn’t fully celebrate—a moment, a milestone, or even a small step forward.
Now revisit it.
Say it out loud: “I did this.”
Share it with someone you trust
Or create a simple ritual—light a candle, take a pause, write it down
Your celebration doesn’t need to be big or public. It just needs to be intentional.
And if you’re willing, ask yourself:What would change if I became someone who regularly celebrates my own wins?

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 shares what it’s like to guide a group of university students through a place she has now visited more than a dozen times. From organizing school visits and cultural experiences to managing the emotional dynamics of a group traveling together in a foreign country, she describes the invisible work behind the scenes of a successful study trip. Planning travel for others, she explains, means balancing structure and flexibility, making thoughtful logistical decisions, and considering the needs and personalities of the entire group.
One of the most unique aspects of Cheryl’s approach is her intentional focus on community building before the trip even begins. By using character strengths conversations and reflective practices, she helps participants understand one another and develop empathy before navigating the challenges of international travel together.
Amy and Cheryl also reflect on how meaningful travel often comes from the moments that aren’t scheduled—walking through a park, discovering a favorite café, or watching children explore nature in ways that spark new professional insights. For Cheryl, leaving space in the itinerary isn’t a planning mistake—it’s a deliberate design choice that allows people to experience a place more deeply.
Throughout the conversation, Cheryl shares what she has learned after many years of leading trips: expect the unexpected, plan the essentials carefully, and leave room for curiosity, connection, and discovery.
Key Takeaways
Planning travel for a group requires thinking about many perspectives, personalities, and needs, not just logistics.
Strong preparation behind the scenes actually makes it easier to be flexible when things inevitably change.
Building a sense of community and grace within the group can prevent small irritations from becoming larger conflicts.
Reflection practices—such as journaling about gratitude and strengths—can deepen learning and connection during a trip.
A well-designed travel experience includes intentional open space, not just scheduled activities.
Unexpected moments—like getting lost, discovering a new place, or taking a spontaneous walk—often become the most memorable parts of travel.
Asking participants what they want from the trip can make the experience more meaningful for everyone involved.
Planning the “skeleton pieces” (housing, transportation, key experiences) provides stability while leaving room for exploration.
Challenge
If you’re planning a trip for friends, family, colleagues, or students, try approaching it with curiosity rather than control.
Before finalizing your plans, ask the people traveling with you:
What’s one experience you hope to have on this trip?
What kind of pace helps you enjoy travel the most?
What would make this trip memorable for you?
Then design your itinerary around a few key “anchor experiences” and intentionally leave open time for wandering, discovering, and reflecting.
Sometimes the most meaningful travel memories don’t happen on the schedule—they happen in the spaces between the plans.
Note: This episode reflects personal experiences only and is not therapy or legal advice. For personal situations, consult a qualified professional.
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy
We want to hear from you! Follow and share your key takeaways, ideas, and inspiration!

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.
They talk about the planning, the rescheduling, the moments of compromise, and the joy that comes from finally saying, “Let’s just make it happen.” Along the way, they explore the value of maintaining traditions, creating space for connection, and recognizing that sometimes the most meaningful moments come from simply being together.
This episode is a reminder that friendships, like many good things in life, often require intention, flexibility, and a willingness to show up.
Key Topics and Takeaways
Why is gathering with friends becoming more complicated as life gets busier
The reality of scheduling around eight adults with full lives
The importance of protecting time for friendship and connection
How traditions (like holiday gift exchanges) evolve over time
Why the experience of being together often matters more than the details of the event itself
The reminder that meaningful friendships require intention, not just good intentions
 
A Challenge for the Week
Think about the people in your life who matter to you but who you haven’t seen in a while.
Instead of waiting for the perfect time, consider choosing a date and simply saying:
“Let’s just make it happen.”
Connection doesn’t require perfection, just intention.
  
Ways to Connect
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy

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 stories, parenting moments, and a little humor (including a throwback to the D.A.R.E. program of the 1980s), Amy and Cheryl unpack the complicated dynamics behind hearing, and honoring, the word “no.”
Together they explore the gray areas: the difference between conversation and persuasion, when explanations help, and how we can respectfully repeat our boundaries when others keep pushing.
 
Key Topics and Takeaways
Why people sometimes ignore or push past a “no.”
The emotional reasons we might struggle to accept someone else’s boundary—or enforce our own.
The role of ego, disappointment, and wanting to help in pushing past someone’s limits.
How relationships can create patterns where “no” starts to feel negotiable.
The difference between dialogue and pressure in conversations.
How explaining your reasoning can sometimes create clarity, even when the answer stays the same.
The importance of recognizing when persistence becomes boundary-crossing.
The “broken record technique” of calmly repeating your no when someone keeps pushing.
 
Memorable Lines
“There’s been a lot of times lately where, even when we’ve said no… people haven’t listened.” — Cheryl Priest
“More often than not, when I probably pushed through somebody’s boundary of no, it was because I really didn’t want to be disappointed.” — Amy Bond
“They might always see no as negotiable.” — Cheryl Priest
“No is a complete sentence… but there’s also sometimes an opportunity for conversation.” — Amy Bond
“You think you want me because I’m the easy ask, but you really don’t want me to do this.” — Amy Bond
“Sometimes people don’t hear your no, they hear that it’s negotiable.” — Cheryl Priest
“It was the broken record technique. Just keep saying no.” — Amy Bond
 
Challenge for the Week
Pay attention this week to moments when you say no, or when someone says no to you.
Ask yourself:
Am I respecting the boundary that was set?
Do I assume “no” is negotiable in certain relationships?
Is there space for healthy conversation without pressure?
Practice the broken record technique if needed: calmly repeat your boundary without apology or escalation.
Sometimes the most respectful thing we can do for ourselves, and others is simply allow “no” to stand.
 
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
Subscribe: Apple Podcasts | Spotify | Amazon Music/Audible | iHeartRadio
Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy
We want to hear from you! Follow and share your key takeaways, ideas, and inspiration!
Thanks for listening to This Was Supposed to Be Easy with Amy and Cheryl.

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 cost?
Through honest stories (including one very long stretch of highway driving), we unpack the emotional weight of overcommitting, the guilt that can follow a boundary, and the quiet strength it takes to choose sustainability over approval. This conversation is about self-trust, integrity, and learning to honor our limits before burnout makes the decision for us.
Key Topics & Takeaways
The difference between “I can” and “I have the capacity.”
Why saying no often feels like letting someone down.
The hidden cost of overcommitment.
Capacity is not a reflection of character.
Listening to exhaustion as information, not weakness.
Why sustainable living requires honest boundaries.
Every “yes” carries a cost — sometimes that cost is you.
Memorable Lines
“Just because I can make it work doesn’t mean it’s wise.”
“Capacity is not character.”
“Exhaustion is information.”
“Every yes costs something.”
“Sometimes the bravest choice is staying home.”
Challenge for the Week
Before you automatically say yes to the next request, pause and ask yourself:
Do I want to do this — or do I feel I should?
What will this yes cost me?
If I say no, what am I protecting?
Practice one intentional pause this week. Even if you still choose yes, let it be a conscious one.