This Was Supposed to be Easy Podcast

This Was Supposed to Be Easy with Amy & Cheryl
The holidays are supposed to feel magical, connected, and full of ease, but often they come with pressure, unspoken expectations, emotional landmines, and complicated relationships. In this episode, Amy and Cheryl take a heartfelt and humorous look at psychological safety during the holiday season and all the ways it can be challenged. They unpack why the dynamics we grew up with can impact how safe (or unsafe) we feel now, how to recognize when your nervous system is signaling danger, and how to create moments of emotional safety for yourself and the people you love.
Blending research from Amy Edmondson, Brené Brown, and the broader psychological safety literature with lived experience, this conversation offers real talk, permission to breathe, and gentle strategies for navigating family, traditions, and triggers, without losing yourself.
Key Topics & Takeaways
The Myth of “Holiday Ease”
Many adults carry the belief that holidays should feel joyful and effortless.
The pressure to host perfectly, avoid conflict, or keep the peace often leads to emotional overload.
Psychological safety allows people to show up authentically, but holidays often highlight the places where authenticity feels risky.
Psychological Safety in Family Systems
Family is the first place we learn what is safe or unsafe.
Old patterns, roles, and expectations often resurface during holidays because those early relational imprints are activated.
You may regress into “younger you” versions of yourself around certain relatives.
Navigating Triggers & Emotional Overload
Holidays can amplify comparison, perfectionism, people-pleasing, and resentment.
Your body often responds before your brain increases heart rate, irritability, shutting down, or over-functioning.
Recognizing the signs early can help you intervene with self-kindness.
Boundaries & Psychological Safety
You are allowed to say no.
You are allowed to leave early.
You are allowed to create new traditions.
Safety is built through clarity, consistency, and communication not through avoiding discomfort.
Trust, Repair, and the Stories We Tell Ourselves
Brené Brown’s framework of trust as a set of small behaviors (BRAVING) applies strongly to holiday dynamics.
When trust has been ruptured in relationships, psychological safety will be fragile.
Repairing, when possible, requires honesty, empathy, and accountability.
Rewriting Holiday Narratives
You don’t have to repeat the same patterns you grew up with.
You can choose what “holiday safety” looks like for your adult self.
Traditions that drain you can be retired; traditions that nourish you can be expanded.
Memorable Lines
During a moment of reflection on holiday interactions and relational rupture, Amy shares:
Amy: “That does not feel good. I do not trust that I can be myself around you for whatever reason.”
As Cheryl reflects on what it feels like to prepare for family or community events, she names something deeply relatable about the anticipation we often carry into holiday spaces:
Cheryl: “Those moments will exist where we don’t feel safe to be our true authentic self.”
 
A Challenge for the Week
Choose one moment this holiday season to intentionally create psychological safety, for yourself or someone else.
Options include:
Setting a small boundary (leaving early, saying no, simplifying plans)
Practicing a self-regulation strategy before a gathering
Naming what you need (“I want this year to feel calm, not perfect.”)
Offering someone else a safety cue (“You’re not alone; I’ve got you.”)
Changing or skipping a tradition that no longer aligns with who you are
Pick one. Make it doable. Let it shift your holiday experience.
 
Additional Resources
Amy Edmondson’s work on psychological safety
Brené Brown’s BRAVING framework
Diary of a CEO interview with Brené Brown (Trust & Emotional Literacy)
Polyvagal theory basics (safety cues & nervous system responses)
Tools for emotion regulation and boundary-setting
Links to your previous episodes on authenticity, belonging, and leadership (optional)
 
 References
Edmondson, A. C. (1999). Psychological safety and learning behavior in work teams. Administrative Science Quarterly, 44(2), 350–383. https://doi.org/10.2307/2666999
Edmondson, A. C., & Lei, Z. (2014). Psychological safety: The history, renaissance, and future of an interpersonal construct. Annual Review of Organizational Psychology and Organizational Behavior, 1, 23–43. https://doi.org/10.1146/annurev-orgpsych-031413-091305
Brown, B. (2018). BRAVING: The anatomy of trust. In Dare to lead: Brave work. Tough conversations. Whole hearts. Random House.
Note: The BRAVING framework originates from Brown’s talks and writing and is most formally published in Dare to Lead. If you want to cite a specific podcast explanation, see below.
Brown, B. (Guest). (2023). Diary of a CEO: Discussing trust, boundaries, and emotional honesty [Audio podcast episode]. In S. Bartlett (Host), The Diary of a CEO.

In this “oh no I do that” conversation, Amy and Cheryl explore the complicated emotions wrapped up in something that should be simple: giving a gift. From the meaning we attach to presents, to the anxiety of letting go once the gift leaves our hands, this episode dives into the psychology behind generosity, expectations, and the stories we create around what a gift “should” mean.
With personal anecdotes and gentle wisdom, this episode invites listeners to reconsider the way we approach gift-giving and maybe release a little pressure in the process.
Key Topics & Takeaways
The emotional weight behind gift-givingGiving a gift isn’t always a simple transaction, it can bring up feelings of obligation, identity, or wanting to be understood.
Letting go of control once the gift is givenA gift doesn’t come with rules. Once it’s given, it belongs to the other person, even if they use it differently than you imagined.
The invisible “meaning” we attach to objectsMany of us unintentionally project hopes, expectations, or interpretations onto the gifts we give.
Why generosity is often tied to self-worthHow we give can reveal what we believe about ourselves, our relationships, and what we’re trying to communicate.
The tension between intention and interpretationJust because a giver sees a gift one way doesn’t mean the receiver will experience it that way, and that’s okay.
Releasing the pressure to make every gift perfectGift-giving is about connection, not performance. Imperfection is part of the beauty.
Permission to make gifting simplerGifts can be joyful, thoughtful, small, practical, or even easy, if we let them be.
 Memorable Lines
“Once you give a gift, it’s no longer yours to manage. That’s the whole point, the letting go is part of the gift.”
“It’s wild how we attach all these emotions to objects, like the gift is holding the relationship.”
“I didn’t realize I had expectations until I saw them not being met. Then I thought, oh… maybe this is my stuff to unpack.”
“Sometimes the simplest gifts are the ones that mean the most, because they’re given without an agenda.”
“If the gift becomes a burden to them, that doesn’t mean your intention was wrong. It means they get to choose what they need.”
Challenge for the Week
Give a gift (big or small) with absolutely no expectations attached.Try this:
Choose something simple or meaningful.
Give it freely, without overthinking.
Don’t monitor how it’s used.
Let the gift go, emotionally and practically.
Notice how the experience changes when you detach from the outcome.
 
Ways to Connect
Website: https://supoposedtobeeasy.com/
Our Podcast Home: http.//supposedtobeeasy.podbean.com/
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In this creative episode, Cheryl and Amy explore the idea of thankfulness as a lifestyle and how gratitude becomes even more powerful when shared in community. Together, they dive into playful, accessible, and joy-filled ways to gamify gratitude—from gratitude walks to Pictionary, paper chains, pottery, and meaningful group activities that spark connection. Whether you're looking to deepen your own gratitude practice or inspire your family, workplace, or community, this episode is full of ideas to help you cultivate more joy, awareness, and appreciation every single day.
Key Topics & Takeaways
Thankfulness as a lifestyle rather than a seasonal practice
How gratitude expands when shared with family, friends, coworkers, and community
The impact of intentionally looking for the good
Creative ideas for “Gratitude Games” that bring playfulness into the practice
How gamification can boost motivation and awareness
Using nature, art, and simple materials to create shared gratitude rituals
Revisiting past gratitude to see growth and continuity over time
Building community bonding through activities that recognize each other’s strengths
Gratitude Game Ideas Mentioned
Gratitude Walks / Gratitude I-Spy Hikes
Gratitude Tree
DIY Branch Gratitude Tree
Gratitude Paper Chain
Gratitude Bingo
Gratitude Pictionary
Pass-Around Keepsake Object
Pottery or Creative Keepsakes
Memorable Lines & Quotes
“Thankfulness as a lifestyle… that is the launching pad for this conversation.”
“How can we look for and think about spreading gratitude into our greater community?”
“When we can make a game out of it—especially with other people—it connects us and helps us see things we didn’t realize we were grateful for.”
“You don’t need the tree from Target. Grab a fallen branch and build gratitude right into your space.”
“Any concrete item made by your community becomes a meaningful reminder that even in tough seasons, there is still joy.”
Challenge
Join the Conversation! Have you enjoyed a group or community gratitude game or practice? We’d love to hear about it! If not, which one are you willing to try this week and who are you going to try it with?
Give one of our gratitude games a try and let us know how it goes!
Resources, Apps & Past Episodes Mentioned
99 Walks AppAn app Cheryl used to gamify walking by setting goals and earning bracelets as rewards. (no longer in operation)
Episode 34 Referenced:We Thought Noticing the Good Was Supposed to be Easy
Connect with us
Website: https://supposedtobeeasy.com/
Our Podcast Home: https://supposedtobeeasy.podbean.com/
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When the calendar starts bossing you around, joy taps out, so Amy and Cheryl share how they took it back: trading obligation math for memory-making, flexing dates, and building traditions that actually fit real life.
Key topics & takeaways
Why “the day on the calendar” doesn’t have to rule your plans
Swapping obligation for flexibility (and sanity)
Thanksgiving reimagined: restaurants, leftovers, and low-lift joy
Christmas Day at home: open-door, pajamas, and appetizers all day
New traditions: Christmas Eve movies, turkey trots, Black Friday sister dates
Making room for teens/partners/in-laws, and for people who’d otherwise be alone
The magic question: “What’s the one thing that makes it feel like the holidays for you?”
Moments we loved
“Control is expensive, presence is richer.”
“It’s not the number on the calendar; it’s the people in the room.”
“Our garage becomes the auxiliary fridge. #Michigan”
Challenge for the week
The One-Thing List: Ask each person, “What one activity/food makes it feel like the holidays?” Prioritize those, skip the rest.
Pajama Open House: Appetizers all day, drop-in welcome, no formal meal.
Date Drift: Celebrate with extended family on the nearest low-stress weekend.
Outsource Thanksgiving: Book a restaurant/hotel buffet; play games afterward.
Anchor & Float: Choose one anchored tradition (e.g., Christmas Eve movie) and let everything else float year to year.
Shout-outs mentioned
Turkey trot (walkers welcome)
Christmas Eve movie + Chinese takeout tradition
Matching family pajamas (dog bandana optional… or not)
Note: While we talk about our own family holidays and traditions, we know that it does not fully represent all that people celebrate. Please help us learn more about the holidays that you celebrate and the traditions that you share!
Connect with us
Website: https://supposedtobeeasy.com/ 
Our Podcast Home: https://supposedtobeeasy.podbean.com/
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Episode description
Fresh off a “Joyful Leadership” workshop, Amy and Cheryl dig into the quiet engine behind joy and happiness: trust. They unpack how trust (or the lack of it) shows up at work, in partnerships, parenting, even in how we talk to ourselves. Expect real stats, relatable stories (hello, micromanaging), and practical ways to build, rebuild, and protect trust without burning out.
Key topics & takeaways
Trust turbocharges wellbeing & results. In high-trust environments: 74% less stress, 50% higher productivity, 106% more energy, 76% more engagement, 40% less burnout, and 13% fewer sick days (stats cited in episode from workplace happiness research).
Micromanaging = “I don’t trust you.” Surveillance, keystroke tracking, or over-prescribing the “how” erodes autonomy and joy, and people either disengage or leave.
Parallel at home: Treat partners as partners (not “babysitters”). Let different but safe approaches stand; over-functioning is exhausting and signals mistrust.
Teens & trust: Pushback is developmentally normal; assume capability, set clear boundaries, and notice where cultural scripts (“you can’t trust teens”) bias your lens.
Repair beats rumination. One breach can outweigh many positives. Own it fast, name impact, and map concrete repair steps; rebuilding takes repeated trustworthy moments.
Five ways to build trust (daily):
Be honest (including “I don’t know”).
Listen with empathy before solving.
Give it time, trust accrues through consistency.
Invest in relationships/belonging (create chances to know one another).
Hold clean boundaries so your yes stays a yes (say no to over-commitment).
Mind the story your brain tells. Use the Brené Brown prompt: “The story I’m telling myself is…” Then check it with the other person before your brain fills the gaps.
Self-trust is practice. Align choices with values, get help when needed (therapy is a green flag), and make your mind a more trustworthy narrator.
Memorable lines
“Control is expensive, at work and in relationships.”
“I’m not micromanaging; I’m guaranteeing the outcome… is still micromanaging.”
“Boundaries make presence possible.”
“Before you spiral, verify: ‘The story I’m telling myself is…’”
Challenge for the week
Pick one trust move and do it twice:
Work: Delegate outcome, not method. Ask, “What do you need from me to succeed?” then step back.
Home: Let a partner handle a routine their way (safety first); say thank you, not “next time do it like…”.
Self: When a fear-story pops up, text or tell the person: “Hey,quick check. The story I’m telling myself is ____. Is that accurate?”
Additional resources / links
Referenced research & ideas:
Meik Wiking’s work on happiness (incl. workplace studies)
The Five Dysfunctions of a Team, Patrick Lencioni (trust as the base layer)
Brené Brown & Adam Grant on values alignment and repair (podcast conversations)
Related episodes: Ep.27 Delegation (for anti-micromanaging tactics); Ep 3, 17, 34 Joyful Leadership series
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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Listener requests for real-life parenting topics led us to a candid conversation with Shannon, a newly divorced mom navigating co-/parallel-parenting with firm boundaries, smart tools, and a lot of self-work. From rewriting a custody agreement and using a parenting app, to protecting her peace (and her daughter’s), Shannon shares what helped, what she’d do again, and what she wishes she’d known sooner. This one’s practical, validating, and full of “copy/paste into your plan” ideas.
Guest introduction
Shannon (“SayItShay05” on TikTok)
Mom to a 10-year-old
Legally divorced in 2022; separation and full boundary-setting journey in 2023
Shares parts of her story (emotional/financial abuse, rebuilding, and co-parenting strategies) on TikTok: @SayItShay05
Key topics & takeaways
Start with safety + assets. First moves: change locks, secure personal/financial accounts, and consult legal/estate planning support.
Custody: ask for everything (then scale back if needed). Spell out specifics you’ll actually enforce: travel permissions, holiday splits, pickup logistics, sleeping arrangements/privacy, medical/education communication, and use of a parenting app.
Know your context better than anyone. Bring cultural/legal nuances to your attorney (e.g., international travel/return risks) and insist they’re written into orders.
Parallel parenting over constant conflict. Different houses, different rules—opt out of fights that don’t improve your child’s wellbeing.
Put communication in one place. A parenting app (e.g., Our Family Wizard) time-stamps messages/expenses, reduces triggers, and creates a clean record for court if needed.
Enforcement matters. Wage garnishment and state enforcement can reduce missed child-support payments and remove you from the reminder/chasing role.
Boundaries save energy later. Holding the line early made medical-crisis coordination possible later—without emotional fallout.
Self-care is strategy, not fluff. Therapy, walks, gardening, and small, finishable projects (hello, DIY patio) helped Shannon think clearly and heal.
Coach the kid without poisoning the well. Be honest at their level, avoid disparagement, and teach skills for spotting/managing gaslighting.
Find your allies. Build a loop of friends/family/professionals who won’t judge and can help you take the next right step.
Memorable lines
“Ask for everything now and give back later—don’t forget to ask for something you’ll need.”
“The app holds everyone accountable— including me.”
“I’m not his secretary anymore.”
“Boundaries up front saved us from conflict when things got hard.”
“Don’t eat the elephant—one scoop at a time.”
Challenge for the week
If this speaks to you, pick one boundary or system you can implement (or tighten) this week. Options:
Move all co-parent comms to a parenting app and stop texting elsewhere.
Draft the specific custody clause you wish you had (sleeping arrangements, holiday rotation, pickup rules) and share it with your attorney for next steps.
Set a personal de-trigger routine (e.g., read messages at set times only; take a 10-minute walk before replying).
Additional resources / links
Shannon on TikTok: @SayItShay05
Parenting app mentioned: Our Family Wizard
Creator referenced: Ugly Truth of Co-Parenting (parallel parenting)
Related episode: Our finances episode with Jeremy (for post-divorce money moves)
Note: This episode reflects personal experiences, not legal advice. Laws vary by state/country—consult a qualified attorney for your situation.
Connect with us
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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!

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

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).

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
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