This Was Supposed to be Easy Podcast

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 “supposed to be easy” has turned into something deeper: a space for honest conversation, imperfect learning, and meaningful connection. In this episode, we name the themes that kept surfacing again and again, and share what happens when you’re willing to press record, even when you don’t have the whole path figured out.
Key Topics & Takeaways
Connection is built through intention, not ease
Joy is something you practice, not something you wait for
Growth often begins with letting go
Confidence is built in motion, not certainty
Being heard is sometimes more powerful than being fixed
Seasons matter, rest, pauses, and timing all have value
You don’t need the whole plan to start, just the willingness to begin
Consistency builds trust, even when things aren’t perfect
Creating something public is vulnerable, and worth it
Impact isn’t always loud, but it is real
 
Memorable Lines
“Connection is built through intention, not ease.” -  Amy
“Letting go can be just as loving as holding on.” -  Cheryl
“Confidence is built in motion, not certainty.” -  Amy
“Being heard is sometimes more powerful than being fixed.” -  Amy
“The meaningful things rarely are easy, but they’re worth showing up for anyway.” -Cheryl
A Challenge for the Week
Take a few quiet minutes and ask yourself:
What season am I in right now?
What might I need to let go of, or lean into,  to honor it?
Where could I take one small step forward, even without certainty?
No fixing. No rushing. Just noticing.
 
Additional Notes
This episode is a thank-you,  to each other, and to you. Whether you’ve been here since Episode 1 or just found us recently, we’re so glad you’re part of this community. Here’s to the next 50 conversations.
 
Ways to Connect
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
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Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy

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 “marshmallow fluff.” From “good news” algorithms, to boundaries that protect mental health, to Cheryl’s seed-ordering ritual as a tiny act of future-facing faith, this episode offers grounded ways to build hope—especially when it doesn’t come naturally. The conversation closes with Emily Dickinson’s “Hope is the Thing with Feathers,” an invitation to carry hope together.
Key Topics and Takeaways
Hope vs. Optimism (and why it’s not toxic positivity): Hope doesn’t ignore hard things—it acknowledges reality and believes change is possible.
Hope is buildable: You’re not either “born hopeful” or not. Hope can be practiced and strengthened over time through small, intentional shifts.
Mindset + action: Hope isn’t passive wishing. It includes agency (“I have influence”) and pathways (finding a route forward)—a nod to Snyder’s Hope Theory and VIA Character Strengths.
How to “train your attention” toward hope: Curating what you consume (news, social media, “good news” accounts) and noticing kindness in everyday moments can restore perspective.
Boundaries are part of hope: Being hopeful doesn’t mean giving everyone access to you. Protecting your mental health can be a hopeful act.
Hope and grief can coexist: Amy names the difference between hoping and wishing—how “wishing things were different” can activate grief, and how hope can live alongside grieving what was or what could have been.
Micro-practices that cultivate hope:
“Two good things” noticing (acts of kindness, small goodness)
Hope journaling (future-oriented reflection + next steps)
Turning hope into a SMART goal (one small step counts)
Having multiple pathways ready (Plan A, B, C)
Leaning on hopeful people—hope grows when shared
Memorable Lines
“True optimism, true hope, is actually grounded in action.”
“Hope is mindset plus action together.”
“It’s not blinders… it helps to see the good things that are also happening.”
“One of the ways for me to remain hopeful is to be aware of what I need to be hopeful… and it doesn’t mean everyone gets access to me.”
“I wish you peace… I hope you find comfort… I hope you meet your goals in a way that doesn’t cause harm to other people.”
“I’m going to grieve the loss of what was… and hope for the best.”
“There’s so much hope inside the seed.”
“Hope grows when it’s shared with others.”
 
This Week’s Gentle Challenge
Try a “Hope Practice” for several days—small on purpose. Choose one:
Two Glimpses of GoodEach day, notice two moments of kindness, humor, or decency (tiny counts). Write them down or text them to someone.
Hope Journaling (5 minutes)Answer: What’s one thing I’m looking forward to?Then: What’s one baby step I can take this week?Bonus: Write two alternate pathways in case your first plan doesn’t work.
Plant a Seed (literal or metaphorical)Do one small future-facing action that says: I believe something good can grow here.Order seeds. Start a file. Send the email. Make the appointment. Take the walk.
And if you’re willing: share your hope practice with Cheryl and Amy—your story might become someone else’s “crumb” of hope this week.
Note: This episode reflects personal experiences and cited research summaries; 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/
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Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy
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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 how leadership has changed, why it feels heavier than it used to, and what organizations (and individuals) might need to rethink if they want leadership to feel sustainable, and worth it, again.
This conversation isn’t about convincing anyone to lead. It’s about understanding what leadership actually costs today, what support is missing, and how we might redesign leadership in ways that feel human.
 
Key Topics & Takeaways
Why does leadership no longer feel like an obvious or attractive next step for many people
How COVID, burnout, and constant change reshaped expectations of leaders
The emotional and invisible labor that often comes with leadership roles
Why boundaries, clarity, and support matter more than ever
The difference between being good at your job and wanting to manage people
How organizations unintentionally push strong contributors away from leadership
Rethinking leadership as a choice, not an obligation
 
Memorable Lines
“Leadership used to feel like growth, now it often feels like weight.”  - Amy
“We tell people they should want leadership, but we don’t always tell the truth about what it requires.” - Cheryl
“Not wanting leadership doesn’t mean you lack ambition.”  - Amy
“Support isn’t a perk, it’s the infrastructure leadership needs to survive.” - Cheryl
 
This Week’s Gentle Challenge
Take a few minutes to reflect on your own relationship with leadership:
What parts of leadership appeal to you?
What parts give you pause?
If leadership felt more supported, more bounded, or more human, would your answer change?
There’s no right response here. Curiosity is the goal.
Note: This episode reflects personal experiences and cited research summaries; 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!

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-week experiment in organization.
Together, they explore how clutter isn’t just about “stuff,” but about habits, unfinished business, mental noise, and the weight of all the things we keep meaning to do. Amy reflects on the tension between being a collector of meaningful materials and recognizing when something no longer serves her current work or life. Cheryl offers solidarity, not expertise—sharing her own struggles with letting go of notebooks, curricula, and “just in case” resources from years past.
As the conversation unfolds, the focus widens from physical space to headspace, and finally to time. What happens when we stop carrying unfinished tasks around in our minds? How much energy is lost to reminders we haven’t acted on yet? And what might shift if we dealt with the small things instead of letting them pile up—on our desks and in our thoughts?
This episode marks the beginning of an eight-week shared experiment. Amy and Cheryl invite listeners to join them in choosing one habit, one space, or one pattern to gently work on—together, imperfectly, and with curiosity.
Key Topics & Takeaways
How physical clutter directly impacts mental clarity
The difference between “new you” and new habits
Why buying organizing tools isn’t the same as using them
Letting go of materials tied to old roles, certifications, or identities
The mental weight of unfinished business (and why it matters)
Organization as a form of self-support, not self-improvement
How clarity can change our experience of time—even when schedules stay full
Using accountability and shared reflection to support sustainable change
Memorable Lines
“I physically feel less scattered in my brain because my space is a little less cluttered.”
“It’s not a new me. It’s new habits.”
“My space feels muffled—like a room full of people talking.”
“The weight of unfinished business is very significant.”
“I’m really good at creating a beautiful space. I’m terrible at keeping it that way.”
A Gentle Challenge for Listeners
Choose one space—a desk, a drawer, a bag, or even a digital folder—and try this:
Make two piles:
This has fully lived its life
This might still have a purpose (I’ll decide later)
Deal with one piece of unfinished business that’s been taking up mental space.
Notice how it feels—not just in your space, but in your body and your thoughts.
You’re invited to stick with this for the next eight weeks, checking in with yourself (and with us) along the way.
Resources & References Mentioned
Change management and behavior change theory
Dr. Katy Milkman’s work on habit formation and change
Marie Kondo’s approach to decluttering (informally referenced)
Use of digital tools (including ChatGPT and search) as alternatives to holding onto physical materials
Full-spectrum light therapy and the impact of winter on mood and focus

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 them lead the way?
This conversation is about resisting urgency, noticing what’s steady, and choosing intention over overhaul as we step into a new year.
Key Topics & Takeaways
The overwhelming “fix everything” energy that often shows up in January
Why constant self-improvement can crowd out reflection and rest
The difference between resetting and re-entering
How small, already working habits can act as amplifiers for more
Letting lived experience, not social pressure, guide next steps
Permission to move into the new year without a full life overhaul
Memorable Lines
Amy: “It feels like everywhere you look; someone is telling you what needs to be fixed.”
Cheryl: “I don’t know that I was ready to jump back in at full speed.”
Amy: “Maybe we don’t need to start over maybe we need to notice what’s already holding.”
Cheryl: “What if keeping what works is the work?”
A Challenge for the Week
Instead of asking “What do I need to change?”, try this:
Name three things that are already working in your life or routines
Ask yourself how you might protect or gently expand one of them
Let that be enough for now
No overhaul required.
Additional Resources & Gentle References
The concept of “re-entry” vs. “reset” after rest or time away
Reflection practices that focus on continuity instead of reinvention
Conversations about seasonal energy, pacing, and sustainability
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
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Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy
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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 of expectations.
Along the way, the two reflect on what it means to stop waiting for something to feel “easy” before you do it—whether that’s planning a trip, pursuing a big goal, or simply giving yourself an unscheduled day to breathe.
Key Topics & Takeaways
Why New Zealand was a “trying something new” momentAmy shares how New Zealand has called to her since 2018, when she first encountered early childhood research connected to the country, and how that dream never fully went away.
The reality of travel vs. the story we tell ourselves about itAmy admits she expected entering the country to feel intimidating, but it ended up being far simpler than she imagined, especially with English (and Māori) visible everywhere.
The “getting there” part was easier than expected… the coming home part was notAmy describes the different emotional/physical experience of the long travel days and how adrenaline, planning tools, and listener tips helped.
Tiny culture surprises that reminded her: you’re not in the U.S.From walking patterns in stores (left vs. right) to the surprising reality of no iced tea and very little ice, Amy shares the small moments that made the experience feel real.
Expectation shifts: childcare center visits + the train ride that didn’t happenAmy talks about really wanting to visit early childhood programs, but running into practical barriers (including the inability to call local numbers). She also describes deciding not to take a 10-hour train trip for a one-hour stop and how that became a “next time” plan instead of a disappointment.
Letting go of “I should be doing more”One of the biggest takeaways: giving herself permission to rest even in another country without guilt.
Strengths in action: learning as a travel compassAmy notices how her “learning” strength shaped her solo days—libraries, museums, cultural experiences, and conversations with locals.
Don’t wait for it to feel easy — make it possibleAmy shares a practical mindset shift: prioritize what matters by investing money, time, energy, and planning in small ways over time.
Memorable Lines
“New Zealand specifically… kind of calls to me.” — Amy
“Don’t… wait for it to just magically happen, or feel easy.” — Cheryl
“In making it possible, it felt easy on the other side.” — Amy
A Challenge for the Week
Choose one thing you’ve been “waiting to feel easy” before you do it and take one step to make it possible instead.
Here are a few easy-to-try options (pick one):
Make a tiny “future me” fund (even $5/week) for something you want to do.
Cancel one subscription and redirect that money toward your goal.
Spend 20 minutes researching the thing (watch one vlog, read one thread, save one article).
Plan one unscheduled block of time this week,no list, no errands, no productivity pressure. Just be.
Then ask yourself: What changed in my body when I stopped waiting for easy and started choosing possible?
Connect with us
Website: https://supposedtobeeasy.com/
Our Podcast Home: https://supposedtobeeasy.podbean.com/
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Social Media: Instagram @supposedtobeeasy / Facebook @Supposed to be Easy
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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 of laughter (including orange peels that are not pizza), gentle wisdom, and questions you can take with you into the rest of the year.
Guest introduction
Dr. JoDell Heroux returns with her signature blend of insight, honesty, and heart, sharing what it looks like to live in your values, make space for creativity, and reject the pressure to always be productive.
Dr. Holly Hoffman brings her joyful, connection-first energy and reminds us that meaningful relationships can be found everywhere, even on a flight when you didn’t pay to pick your seats.
Key topics and takeaways
A question to start your year: What’s something new you want to learn or try in 2026?
Creativity as care: JoDell shares how doodling became a mindfulness practice, and how giving yourself permission to create (without producing) can unlock new energy and ideas.
The power of “unproductive” moments: Quiet drives, clay play, doodles, rest… and how those things can make us more connected and more present.
Travel dreams and “homebody eras”: New Zealand kindness foundations, Sweden/Finland/Estonia adventures, Ireland and Scotland dreams, and the very real joy of staying home with your dogs.
Reflection across the year: What are you proud of from 2025, and what do you hope you’ll be proud of when 2026 ends?
Values in action: Living in alignment with your core values can create contentment, clarity, and a deeper sense of balance.
How do you want others to feel after interacting with you? The group shares intentions like valued, important, authentic, and truly connected.
Memorable lines (quotes)
“The more we take time to be what we would consider unproductive, the more productive we end up being.”-JoDell
“I want people to feel valued… like their time, their brilliance, their person was valued.”- JoDell
“I want them to know that they’re important… their ideas, their presence is important.”- Holly
“Somebody in my presence would feel like they could be exactly who they are, and that that’s okay.”- Amy
“How can I bring time back in and offer it to others?”- Cheryl
A challenge for the week
Pick one question from this episode and write your answer down, no overthinking, just honesty.
Try one of these:
What’s something new you want to learn or try this year?
Where is somewhere new (or different) you’d like to go, or how do you want to experience “home” differently?
What do you want to be proud of when this year ends?
How do you want people to feel after interacting with you?
Bonus: share your answer with someone you trust, or with us.
 
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
Stay curious, stay connected, and keep wondering.

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 stories of seeds, silence, family life, and personal growth, Amy and Cheryl offer permission to slow down, tend to what matters, and trust that even quiet movement is still meaningful progress.
Key Topics & Takeaways
Why traditional New Year’s resolutions often create pressure, guilt, and burnout
The concept of wintering as a season for reflection, rest, and gentle dreaming
Using bingo cards, vision boards, or wishes as flexible intention-setting tools
How breaking goals into “baby steps” can support motivation and self-compassion
Letting intentions stay open-ended so they can grow in unexpected ways
Challenging all-or-nothing thinking (full wins, half wins, and hearts count too)
Creating categories for intentions (rest, relationships, personal growth, energy)
The importance of curiosity when comparing how others approach goals
Making space for quiet—silence, slowness, and reflection—as a form of care
Moving forward without speed, urgency, or a perfect master plan
Memorable Lines & Quotes
“Moving forward doesn’t have to be fast to be meaningful.”
“Permission to be human gives us permission to show up less than perfect.”
“What if we thought about direction without the speed… yet?”
“It doesn’t have to be all or nothing—sometimes it’s a half-heart.”
“Wintering invites us to tend, not push.”
“Slower movement is still movement.”
“There have to be seasons where it’s not about becoming more, but becoming truer.”
“You don’t have to do everything right now.”
“What do I want to nurture and offer care and attention to?”
Resources & Episodes Mentioned
Episode 42 – Wintering, Rest, and Reflection
Referenced multiple times as the foundation for this continued conversation
VIA Character Strengths Assessment
Discussed in relation to love, learning, wisdom, and shifting priorities
Intention-Setting Tools Referenced
Bingo cards (annual or seasonal)
Vision boards
Wishes rituals
Word of the Year practices
Upcoming Resources
Watch our social media for additional details on categories of rest will be shared via social media and the website

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 comes next.
Key Topics & Takeaways
What “wintering” means beyond cozy aesthetics
The pull between hibernation and ongoing responsibilities
Reflecting on goals without labeling them as success or failure
Why bingo cards allow for reflection that SMART goals sometimes don’t
How intentions can shift as life unfolds
The importance of rest in creating space for clarity and future direction
Different types of rest and how to identify what you need right now
Letting go of internal criticism and practicing grace during reflection
 
 Memorable Lines
Amy: “Creating some time and some space to not have to produce as much.”
Cheryl: “You don’t know what you don’t know.”
Amy: “I don’t think I failed. I think I reprioritized my time, effort, energy, and resources.
Amy: “When I rest, it gives my brain the space to reflect.”
 
This Week’s Gentle Challenge
As you listen, ask yourself:
What type of rest do I need right now?
Is it:
Intellectual rest
Emotional rest
Sensory rest
Social rest
Physical rest
Spiritual rest
Mental rest
Choose one area and give yourself permission to lean into it, without guilt, productivity pressure, or needing it to lead somewhere yet. We will be posting ideas for each on our Social Media and website!
 
 Additional Resources
Wintering: The Power of Rest and Retreat in Difficult Times by Katherine May
Making Winter: A Hygge-Inspired Guide to Surviving the Winter Months by Emma Mitchell
Atomic Habits by James Clear
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!

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 stick. Plus: holiday concerts, cozy movies, and a listener invitation to help us build the ultimate winter-holiday playlist.
Key topics and takeaways
Why holiday music is so powerful: it connects to our senses and makes memories more vivid (and more retrievable later).
Nostalgia playlists: childhood albums, record players, and the songs that instantly bring you back.
When is it “allowed” to start holiday music? November 1st, day-after-Thanksgiving traditions… and yes, even August (no judgment… mostly).
Holiday decorating as a whole experience: music, rituals, themed trees, and making the work feel worth it.
The “new music vs. traditions” debate: keeping favorites sacred while still letting new songs earn a place in your holiday story.
Holiday concerts & events: Nutcracker, orchestral shows, jazzy Christmas, Mannheim Steamroller, and dream events like Trans-Siberian Orchestra and candlelight concerts.
Holiday movies as mood-setters: from classics like Elf and Home Alone to cozy, predictable Hallmark/streaming movies you can wrap gifts too.
Songs you love… and songs you cannot: the funny (and emotional) stories behind the “skip it immediately” list.
Listener invitation: share your favorite winter-holiday songs, especially from holidays and traditions beyond the ones Amy and Cheryl grew up with, so we can build a community playlist.
Memorable lines
“One of my favorite things about the holidays… is music.”- Amy
“What makes Christmas special to me is that it’s a finite amount of time.”- Amy
“We are saturated in Christmas music.”- Amy
“It’s important to me to be in that top 0.5% of listeners…”- Cheryl
“You’re not watching it because you’re like, ‘What’s gonna happen next?’ You’re watching it because it’s sweet and mindless.”- Amy
“Those times that our senses are engaged, those are those moments when we might remember a moment.” - Cheryl
“I would love for our listeners to share some of their favorites.” - Cheryl
 
A challenge for the week
Pick one memory you want to strengthen this season and pair it with a song on purpose.
Choose a “signature song” for decorating, baking, driving, or wrapping gifts.
Play it every time you do that activity.
Notice how quickly your brain starts linking the music with the feeling.
Bonus: add one new-to-you holiday song to your rotation and see if it earns a permanent spot.
Additional resources or links
The Art of Making Memories (book mentioned by Cheryl)
We’ll be creating a Winter Holiday Playlist, and we want your favorites!
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!