This Was Supposed to be Easy Podcast

By supposedtobeeasy

Your go-to podcast for connection, joy, and a good dose of laughter. Hosted by 2 friends who’ve seen enough of life to know that it’s never as simple as it sounds (or looks), each conversation cele

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FAQs about This Was Supposed to be Easy Podcast:

How many episodes does This Was Supposed to be Easy Podcast have?

The podcast currently has 54 episodes available.

This Was Supposed to be Easy Podcast episodes:

October 29, 2025S2 Episode 34: We Thought Noticing the Good Was Supposed to Be Easy
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 positivity. From confirmation bias at work to social media algorithms, gratitude habits, and photographing everyday symbols (hello, heart-shaped clouds and Blue Jays), this is a grounded, science-meets-woo conversation for leaders and humans who want more good in their day.
Key topics & takeaways
Warm open: Girls’ trip vs. destination wedding at home (Mackinac!) and Michigan’s wild weather mood swings.
RAS, in plain English: A brainstem network that filters sensory input, letting through what’s urgent or important and muting the rest.
Top-down training: You can influence your RAS by setting intentions and goals (what you want to notice) so it highlights more of that.
Leadership lens: Beware confirmation bias, leaders tend to find evidence for what they already believe about their teams. Choose better default beliefs and you’ll notice more of the behaviors you want to reinforce.
Algorithm analogy: Your attention works a lot like TikTok’s feed. Engage with something, and you’ll get more of it, for better or worse.
Joy is not toxic positivity: This is not glitter over hard things. It’s using neuroplasticity intentionally to notice genuine goodness alongside reality.
Simple practices that work:
Daily or weekly gratitude reps (e.g., 3 things and why they mattered).
Photo-log your symbol (hearts, Blue Jays, a color you love).
Start meetings with “What’s going great?” to shift the room’s state.
Stories that stick: Bronco Sport “Happy Blue,” heart-shaped clouds, Blue Jays as messages, and how one negative icebreaker can tank a meeting.
Memorable lines
“Our brains are wired to find what we’re looking for”, Cheryl
“It’s fortunate we can train our RAS easier than we can train our algorithm”, Cheryl
“We tune in to what we want to see”, Amy
“This isn’t fake glitter over hard things”, Cheryl
“Ask, what’s going great? and watch the energy change”, Cheryl
“All the stuff is still happening, we’re just choosing where to focus”, Amy
Challenge for the week
Find Your Signal (7-Day Mini-Experiment)
Pick a symbol you’ll look for (hearts, a bird, a color, a word).
Snap a photo or jot a note each time you spot it (aim for 10+ finds).
Gratitude add-on: Write one sentence on why one find mattered that day.
Leadership nudge: Open one meeting with “What’s going great?”
Share it: Post your favorite find and tag us so we can cheer you on.
Additional resources or links
Mel Robbins, The High Five Habit (RAS + a simple daily experiment)
Ways to connect
If this episode sparked something for you:
Follow/Subscribe on your favorite podcast app so you never miss an episode.
Rate & Review, it helps new listeners find the show.
Say hi on social (Instagram, Facebook, etc.) and share what you’re noticing, tag us so we can celebrate with you!
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37min
October 22, 2025S2 Episode 33: We Hoped Dating After Widowhood Would Be Easier (Part 2)
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 like to "choose yourself" first. This conversation is tender, honest, and surprisingly funny, because sometimes the best way through a rollercoaster is to laugh, take notes, and keep your friends on speed dial.
Guest Introduction
Lee is a licensed counselor and thoughtful truth‑teller who recently spent six months exploring online dating after widowhood. With equal parts compassion and curiosity, she shares both her personal experiences and professional perspective on what helps, and what hurts, when you’re ready to connect again.
Key Topics & Takeaways
AI & authenticity online: Profiles can read like travel ads, overly polished, tidy “lists of three,” and wording that doesn’t match the person’s real-time messages. Trust the mismatch; it’s data.
Spotting scams & red flags: Look for formulaic language, over-religious signaling like “seeking a God-fearing woman,” and writing that feels generic or too perfect. Photos are often stolen; the writing is the tell.
“Choose yourself” first: You can’t genuinely choose a partner until you’ve chosen yourself, liked yourself, backed yourself, and named your non‑negotiables.
Dating takes work: For Lee, six months of dating across four platforms felt like a part-time job, time-consuming and not cheap. Effort in doesn’t always equal effort back.
Hold the opposites: Take dating seriously and stay light-hearted. Hope for connection and release attachment to outcomes. Be invested and okay if it’s not forever.
Boundaries are kindness: Protect your peace fiercely. Clarity about what you want, and what you won’t do, saves time, money, and heartache.
Resilience after loss: Healing isn’t linear. A painful discovery set Lee back for a while; honesty (with herself and others) helped her recalibrate.
Where Lee is now: Enjoying a high‑quality connection that’s currently limited by travel and availability, and taking a break from paid apps while life sorts itself out.
Memorable Lines
“You can’t choose someone else without first choosing yourself.”
“Dating was a part‑time job for six months.”
“Protect yourself fiercely. Be on your own side.”
“A good relationship makes the hard things softer and the good things better.”
“Can you hold out hope and let go of attachment to an outcome?”
“Have dinner with your girlfriends and tell them all your crazy stories.”
Connect with Us
If today’s episode landed for you:
Subscribe & Review on your favorite podcast app
Share this episode with a friend who’s dipping a toe back into dating.
Join us on Instagram and Facebook @ThisWasSupposedToBeEasy for weekly prompts and behind‑the‑scenes.
— Amy & Cheryl
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37min
October 15, 2025S2 Episode 32: We Hoped Dating After Widowhood Would Be Easier (Part 1)
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 of navigating online dating while healing. She brings a counselor’s insight and a human heart to every detail, reminding us that finding connection starts with knowing who you are first.
This episode is packed with “aha” reflections, tender truths, and practical advice like how to tell when someone’s profile was clearly written by AI (spoiler: it’s the overuse of lists of three). And as always, Amy and Cheryl bring their mix of humor and heart to the table, making even the awkward parts of dating feel like an act of courage.
Guest introduction
Lee is a licensed counselor and thoughtful truth‑teller who recently spent six months exploring online dating after widowhood. With equal parts compassion and curiosity, she shares both her personal experiences and professional perspective on what helps, and what hurts, when you’re ready to connect again.
Key topics & takeaways
Grief meets dating: Lee’s therapist reframed the hurdle: dating wouldn’t be about being “ready,” but about making the loss feel more real and final, and that’s what’s scary.
A planned re-entry: Lee chose Thanksgiving through New Year’s 2024 to rejoin apps, anticipating a grief wave when clients cancel more often; it happened, she processed it, and emerged ready.
Apps tested (and what worked): eHarmony, Match, a plus-size–focused app, and OurTime. Best yield: Match and OurTime.
Profile strategy: Lee intentionally wrote a longer, clearer profile (3–4 short paragraphs), highlighted values, and kept her occupation vague (“mental health services”) to avoid being cast as a fixer.
Photo ethos: Real, current, no filters. A mix of full-body/close-ups; made-up and no-makeup. She expects the same effort from others.
The “lazy like” filter: Hundreds of empty likes rolled in. Her stock reply: “Besides my photos, what in my profile made you reach out?” Non-answers = no.
Safety & judgment cues: She avoids profiles showing young kids’ faces; prefers when faces are obscured for privacy.
The “real‑life translation” test: If a photo pose/setting would be off‑putting in a real first encounter (gym mirror biceps, urinal selfie, scowling car pic), that’s a pass.
Quality over quantity: Goal is not mass appeal; it’s alignment. Being “picky” about effort and reciprocity is healthy.
What the numbers said: She scanned 5,000+ profiles (ages ~41–55) and interacted with <2%. Fewer than ~10% had truly written profiles.
Algorithms & empty engagement: Many “likes” are to juice visibility; don’t take it personally.
AI & scams-red flags: Over‑polished, PR‑like prose; repetitive “lists of three”; religiosity tropes (e.g., “God‑fearing woman”); writing voice in chat that doesn’t match the profile because AI wrote it.
Self-respect first: “You can’t choose someone else until you’ve chosen yourself.” Confidence and effort are non‑negotiable.
Memorable lines (quotes)
“It’s not about whether you’re ‘ready’ to date. It’s that dating can make the loss feel more real, and that’s what’s frightening.”
“If someone won’t read two paragraphs, they’re not my person.”
“A profile is your digital first impression, if the best you can do is a bathroom selfie, that tells me what effort will look like later.”
“I’m not McDonald’s, ‘billions served’ is not the goal. Alignment is.”
“You can’t choose someone else without first choosing yourself.”
A challenge for the week
Try Lee’s Intentional Dating Audit, a playful but powerful exercise to bring mindfulness back to your search for love:
Write (or update) your profile to include: values, how you spend time, what reciprocity looks like. Aim for 2–4 short paragraphs.
Photo check: 4–6 recent photos, including a full‑body shot and a natural look. Ditch the filters and show your real smile.
Set your lazy like reply: “Besides my photos, what in my profile made you reach out?”
Define 3 effort cues you require (e.g., a written profile, recent photos, a thoughtful first message).
Run the real‑life test on your own photos, and on others’. Would this vibe feel good in person?
Ways for listeners to connect
Subscribe and leave a review—it helps others find the show.
Follow us: Instagram & Facebook — links in episode description.
Share this episode with a friend who’s re‑entering dating after loss or just needs a laugh and a little courage.
This is Part 1 of 2. In Part 2: the “worst date in human history,” how Lee screens for readiness, and how to spot AI-written profiles in the wild (with examples).
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38min
October 08, 2025S2 Episode 31: We Thought Listening Was Going to be Easy (Part 2)
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”), real talk about discomfort, and a gentle push to listen in ways that improve relationships.
Key Topics & Takeaways
Covey’s Levels of Listening: ignoring, pretend, selective, attentive, and empathic use awareness to notice (and shift) your current level.
Selective & Pretend Listening: why we drift, and the hilarious “hook word” story that snaps people back.
The Power of the Pause: count to three before responding; silence invites depth (and stops hijacking the convo).
Reflective Practice (without parroting): reflect meaning or emotion so people feel heard and can move on.
Validation Loop: repeating often means “I’m not sure you heard me.” Reflect to break the loop.
Nonverbals Speak Loudly: tone, pace, eye contact, posture listen to the spoken and unspoken.
Ask Open-Ended, Invitation Questions: “What was that like for you?” “Tell me more…” and then actually listen.
Designing for Joy & Curiosity: in families, teams, and trainings, listen for what’s said and unsaid to create autonomy and engagement.
Relationships First: better listening → better connection.
Memorable Lines
“Maybe more awareness will help me notice when I’m in a level I don’t want to be in.” – Cheryl
“If you ask the question, listen to the answer.” – Amy
“Reflect the emotion when you can’t reflect the words.” – Amy
“Silence can be an invitation, not an absence.” – Cheryl (on leaving thinking pauses)
“When you develop the skill of listening, you’re really improving relationships.” – Amy
Challenge for the Week
Pick one conversation and practice the 3–2–1:
Count 3 seconds after they finish.
Reflect 2 things you heard (one content, one feeling).
Ask 1 open-ended follow-up (“What felt most important about that?”).
Notice what changes in them and in you.
Additional Resources or Links
Stephen R. Covey, The 7 Habits of Highly Effective People (Levels of Listening).
Brené Brown’s recent podcast conversations with Adam Grant—notice how the pauses are left in to model reflective listening.
M. Scott Peck quote (from Part One): “Listening is being able to be changed by another person.”
Ways to Connect
Love this series? Share it with a friend who’s practicing better listening.
Follow: @thiswassupposedtobeeasy (Instagram & Facebook)
Subscribe & leave a review—tell us how you used the 3–2–1 challenge!
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29min
October 01, 2025S2 Episode 30: We Thought Listening Was Going to be Easy
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.
Through personal stories, reflections on ADHD, family dynamics, sarcasm, and even the role of technology, Amy and Cheryl unpack how listening shapes connection, and why it’s harder than we think.

Key Topics & Takeaways
Listening as a skill we can practice and develop.
How family and cultural backgrounds influence listening styles.
The difference between hearing and listening.
Interrupting, cutting off, and the habit of “finishing” someone else’s thoughts.
The role of distractions (phones, watches, competing priorities).
Listening with intention: to respond, to learn, or simply to support.
Why setting boundaries around time can improve listening.
The trap of listening to fix versus listening to understand.
Insights from Suzanne Axelsson’s work on.

Memorable Lines
“Listening is being able to be changed by another person.” – M. Scott Peck
“Hearing and listening are not the same thing. Hearing is vibration on your eardrum. Listening is doing something with it.” – Amy
“Sometimes we need the courage to keep our mouths shut, even if we have opinions.” – Cheryl
“Am I speaking to hear myself speak, or am I speaking because I have value to add?” – Amy

Challenge for the Week
This week, notice the why behind your listening. Are you listening to respond? To fix? To connect? Try pausing and asking yourself:
Do I need to add something here, or would silence serve better?
What does the other person really need from me in this moment?

Additional Resources
Suzanne Axelsson’s The Original Learning Approach (chapter on Listening)
Stephen Covey’s The 7 Habits of Highly Effective People (levels of listening).

Stay Connected
If this episode made you think differently about listening, don’t miss Part Two coming soon!
Follow us on Instagram & Facebook: @thiswassupposedtobeeasy
Subscribe to the podcast so you never miss an episode.
Leave us a review-we’d love to hear how you are practicing listening in your own life.
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31min
September 24, 2025S2 Episode 29: Who Knew That Trying Glamping Would be Easy?
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, and even transformational.
Key Topics & Takeaways
Start with comfort to try something new: Pick conditions (people, place, amenities) that make you excited, not overwhelmed.
Environment matters: Design, small touches, and thoughtful amenities can flip a maybe into a yes.
Nostalgia as a bridge: Keep the cozy parts (fires, walks with flashlights, coffee chats) while removing deal-breakers (cold, long bathroom treks).
Reframe “inconveniences”: When the overall experience is positive, the tiny hassles don’t define the story.
Baby steps aren’t cheating: Ease into new territory so you can show up as your best self and actually enjoy it.
Growth through positivity: You don’t have to be in crisis to evolve joyful experiences that create change, too.
Memorable Lines
“Think about all the little successes, even if it wasn't exactly as you imagined.”-Amy
“Permission to take a baby step into something new.”-Cheryl
“We decided that we were going to try things that we have been interested in.”-Cheryl
Challenge
Try one small “glamping-style” upgrade in an area you’ve been curious about:
Pick your new thing (something that genuinely appeals to you).
Add comfort: choose one or two “luxury” touches that remove your biggest barrier (location, gear, schedule, or a buddy).
Invite the right people: do it with someone who makes the experiment feel safe and fun.
Name the win: after you try it, identify 2–3 little successes—no matter how small.
Join the Conversation
Let us know what you are actually committed to trying in the very near future. What is the thing, what comforts will you add, and who might you invite to join you? We want all the deets and pics afterwards!
Resources & Links Mentioned
Silver Birch Resort (Williamsburg, MI) — glamping domes near Traverse City.
https://silverbirchmichigan.com/
Traverse City area — food, fun, and new-thing opportunities.
https://www.traversecity.com/
Stay Connected
This Was Supposed to Be Easy with Amy and Cheryl
Subscribe & Review: https://supposedtobeeasy.com/
Instagram: @supposedtobeeasy
Facebook: Supposed to be Easy
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32min
September 17, 2025Season 2 Episode 28 - We Thought Showing Kindness Would Be Easy (with Suzanne Axelsson)
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 a safe space to practice them.
This episode also touches on cultural norms (pleases/thank‑yous), the risks and rewards of discomfort, and how educators can move beyond forced “I’m sorry” scripts toward authentic repair and connection.
Guest
Suzanne Axelsson (Sweden) - educator, international speaker, play activist, and author of The Original Learning Approach. Suzanne brings an autistic lens to questions of fairness, inclusion, and how communities cultivate genuine kindness.
Key Topics & Takeaways
Kindness ≠ Niceness: Niceness seeks approval; kindness centers well‑being (yours and others) even when it’s uncomfortable.
Authentic Repair: Replace forced apologies with empathy‑building prompts that invite needs and solutions.
Play as Practice: Play is the “safe lab” where children rehearse empathy, listening, and self‑regulation without high‑stakes consequences.
Bravery Matters: Kindness often requires tolerating discomfort and saying firm, caring “no’s.”
Skills Stack: Listening, patience, curiosity, self‑regulation, and community‑building scaffold kindness over time.
Culture Counts: Words like “please/thank you” can be niceness scripts; gratitude and care can be expressed beyond language rules.
Adults Are Learners Too: Give yourself permission to be new; refinement comes from repetition and reflection.
Memorable Lines
"Kindness is rooted in a genuine empathy, understanding, caring for other people, and that we're doing it, because we know it's the right thing." - Suzanne
"Kindness ripples."-Suzanne
"It takes bravery to be kind."-Suzanne
"Are girls taught to be nice more than boys?"-Suzanne
"Democracy has to be lived, not just learned about."-Suzanne
"Play is the safe space where we can practice being kind."-Suzanne
Try‑It‑Now (for educators & parents)
Swap “Say you’re sorry” with: “I see you’re upset. Is there anything I can do?”
Debrief conflicts with three questions: What happened? How do they feel? What would help now?
Build a kindness skills menu: listening, turn‑taking, waiting, asking open questions, checking in.
Create low‑stakes practice: cooperative games, role‑plays, and rebuilding together after mishaps.
Resources & Links
Suzanne Axelsson-Substack, social links, and projects (https://suzanneaxelsson.substack.com/)
Book: The Original Learning Approach (https://www.redleafpress.org/The-Original-Learning-Approach-Weaving-Together-Playing-Learning-and-Teaching-in-Early-Childhood-P2704.aspx)
Purposeful Gatherings event (https://cherylpriest.com/purposeful-gatherings-in-early-childhood/)
Study Group: Sweden & Finland (May 2026)-interest form (https://cherylpriest.com/inspiring-places-practices-sweden-finland/)
Connect with Us
Podcast: This Was Supposed to Be Easy with Amy & Cheryl
Subscribe/Review: If this episode resonated, leave a rating and share it with a friend.
Instagram: @supposedtobeeasy
Facebook: @Supposed to be Easy
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34min
September 10, 2025S2 Episode 27 We Thought Learning How to Delegate Would Be Easy
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 struggle with delegation and mental load.
The common excuses: “It’s faster if I do it myself” and “No one can do it as well as I can.”
Teaching kids life skills through delegation (laundry, cooking, chores).
Delegation at work: handing off grading, sharing responsibilities, using AI.
Avoiding micromanagement and learning to trust the process.
How genuine recognition of others’ strengths builds trust and connection.
Themes
Delegation as survival: letting go to reduce burnout.
Life skills and empowerment: giving others the tools to thrive.
Redefining success: focusing on outcomes instead of perfection.
Mental load and fairness: sharing responsibility beyond just tasks.
Identity and control: questioning why we tie self-worth to “doing it all.”
Listener’s Challenge
Identify one task this week that you could delegate. Ask yourself: Is this something only I can do? Or is this something someone else could take on and even enjoy? Then actually hand it off whether to a family member, a colleague, or even technology. We’d love to know how it goes!

Ask Yourself Some Questions
What tasks drain my energy but could easily be done by someone else?
Do I struggle to delegate because I want control, or because I haven’t built trust?
How might teaching someone else a skill benefit them in the long run?
Am I delegating tasks and the mental load, or am I still carrying the hidden weight?
Where am I micromanaging instead of trusting the process?

Key Quotes (Amy & Cheryl)
“The day I step into adulthood is the day I take 100% responsibility for my actions… including sharing the love.” – Cheryl
“It will take you longer to explain it once, twice, maybe three times. But then you’re not the one doing it anymore.” – Amy
“My proud moment was walking into the laundry room and catching my son teaching his younger cousin how to do laundry.” – Cheryl
“Delegation isn’t a weakness.” – Cheryl
“Sometimes delegating the mental load is what we really need to do.” – Amy
“Which matters more; the how or the what? That’s the key to avoiding micromanagement.” – Amy
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42min
September 03, 2025S2 Episode 26: We Thought Getting to Season Two and Trying New Things Would Be Easy
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 share ideas for and stories about trying new things so we can continue to be brave together—in community.
Highlights
Framing Season 2 as “a year of trying new things” together and in community
Amy’s first passport + New Zealand trip prep (long-haul flight jitters, extra entry requirements and more)
Cheryl’s courage cue: a possible mini–class reunion and a spring study tour to Sweden & Finland
A conversation about the different “buckets” of new things that we’ve thought about trying and are getting ready to take action including:
Creativity bucket: sugared pansies on a cake, air-dry clay projects, glassblowing ornaments and more
Food & drink bucket: pasta and cheesemaking classes, charcuterie, craft mocktails
Nature & adventure bucket: boat outings, foraging chanterelles, forest bathing, Michigan outdoors
Play & connection bucket: escape rooms, karaoke/trivia, dance, language crash courses
The core lens for the season: keeping a strength focus, reframing, trying new things of course, and more honest stories about when things aren’t “easy”
Open invitation to listeners to suggest ideas publicly (social posts) and share experiences in being new at something
Themes
Brave curiosity in community
Permission to be human (and to say no)
Creativity as fuel
Reframing expectations vs. lived experience
Everyday adventures (local and global)
Hospitality of stories: learning from novices and experts
Listener’s challenge
Pick one new thing to try in the next few weeks.
Choose a category (Creativity, Food/Drink, Nature/Adventure, Play/Connection) or make your own.
Define a tiny first step (15–60 minutes, make it low cost or even free).
Do it with someone or invite us to try it on your behalf.
Share a pic or a 3-sentence reflection on our socials so others can get inspired.
Ask yourself some questions
What’s one thing I’ve been low-key curious about but keep postponing? Why?
If “brave” were 10% more than I feel today, what tiny step would I take?
Do I want to hear from beginners trying it for the first time, or from seasoned guides (or both)?
How will I make this social-who will I invite, and where will I share my story?
If it isn’t easy at first, how could I reframe the experience, so it still counts as a win?
Key quotes (Amy & Cheryl)
“We can do it together. We can do it in community, and we can share our stories with each other.” -Cheryl
“Sprinkling adventure and opening ourselves up to curiosity throughout this upcoming season.” -Cheryl
“We’ll see how brave I am feeling.” -Amy
“This is… this is permission to be human, permission to be messy, permission to be brave, and permission to say no sometimes.” -Cheryl
“Food and drinks, a definite category that draws my attention.” -Cheryl
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28min
August 27, 2025S1 Episode 25 – Season Finale: Celebrating This Was Supposed to Be Easy
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, you’ll hear:
Our behind-the-scenes journey—how a nine-month idea became a podcast with over 1.2K downloads.
Fun listener stats (17 countries strong!) and what that milestone means to us.
The episodes that surprised us, moved us, and resonated most with you (hint: friendships, strengths, joy, and workplace well-being).
Heartfelt listener feedback that reminded us why we started.
Why Fall might be our favorite season (sweaters, nail polish, and pumpkin bread included).
The importance of taking imperfect action, because waiting until you’re “ready” means you may never start.
Looking ahead:
Season Two is coming NEXT WEEK! We’ll be bringing you more conversations, inspiring guests, and ways for YOU to join in.
We’d love to hear from you, what are some of the things in life that you thought were supposed to be easy, but weren’t? Drop us a note on social media or send us a message, we’re building Season 2 with you in mind.
Thank you for being part of our community. Whether you’ve listened to one episode or all 25, we’re so grateful you’re here.
Don’t forget to subscribe so you get notified the moment Season Two drops!
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36min

FAQs about This Was Supposed to be Easy Podcast:

How many episodes does This Was Supposed to be Easy Podcast have?

The podcast currently has 54 episodes available.