Lifestyle Cailyn and Gillian Lifestyle Cailyn and Gillian

Episode 135: Asking For A Friend: How Do I Stay Safe While Traveling (And What To Do If You Get Robbed)

It’s OOO season, friends! Between bachelorette weekends, road trips, summer vacay plans, and everyone decidedly going to Italy this month, travel is top of mind this time of year. And as the saying goes, “Travel is the only thing you buy that makes you richer”...But what happens if your phone is stolen, you lose your wallet, and your identity is compromised while abroad!? #truestory



It’s OOO season, friends! Between bachelorette weekends, road trips, summer vacay plans, and everyone decidedly going to Italy this month, travel is top of mind this time of year. And as the saying goes, “Travel is the only thing you buy that makes you richer”...But what happens if your phone is stolen, you lose your wallet, and your identity is compromised while abroad!? #truestory

In this week’s Asking For A Friend, our resident travel expert, Gill, is in the hot seat to drop some hard-earned lessons on how to stay safe while traveling (especially as a solo traveler), and to share her first-hand experience with what to do if you get robbed abroad.

Tune in as we chat about:

  • Prioritizing safe areas to say

  • Why you should *always* turn on Find My iPhone and share your location with family/friends

  • Keeping important itinerary details with you at all times

  • Safe transportation tips while traveling

  • What happened when Gill got mugged abroad, and everything she learned from it

  • The stuff you should actually pack to keep you safe

  • How to avoid losing your belongings

  • Protecting your personal data & banking info while traveling

  • The power of trusting your gut

At the end of the day, fear should never hold you back from traveling and experiencing this beautiful planet. With proper preparation and staying smart and aware, the world is truly your oyster.

If you have any other burning questions for us and want to get us in the hot seat DM us or send us an email at contact@teachmehowtoadult.ca and we’ll dive into it in an upcoming Asking For A Friend! 

Big thank you to Telus Online Security for sponsoring this episode. You can learn more and check out their plans at Telus.com/online-security.


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 133: The Quickie: How To Breakup Without Being An Asshole

Breakups are generally unavoidable in life, but that doesn’t mean we’re any good at them. The stressful conversation, the guilt, the division of friendships, navigating all the emotions and aftermath… it’s not a fun time. So this week, we’re taking inspiration from our girl TSwift, the breakup queen herself, and diving deep on how to call things off, in the kindest way possible.



Breakups are generally unavoidable in life, but that doesn’t mean we’re any good at them. The stressful conversation, the guilt, the division of friendships, navigating all the emotions and aftermath… it’s not a fun time. So this week, we’re taking inspiration from our girl TSwift, the breakup queen herself, and diving deep on how to call things off, in the kindest way possible. 

The key to a healthy breakup (or a conscious uncoupling, a la Gwenyth) is honesty and accountability. No two relationships or breakups are the same, but the modern era of dating has seen a rise in general assholery when it comes to ghosting and ending relationships. So whether you’re trying to end a casual situationship, a long term relationship, or something in between, tune in for tips on how to lead with compassion and break up with grace.

Join us as we chat about:

  • The era of ghosting and dating douchebaggery 

  • What to consider before broaching the conversation

  • How to be honest, without being cruel

  • Constructive criticism and “I” statements

  • Getting real with yourself about the actual reason for the breakup, and the role you played

  • Avoiding a prolonged breakup

  • Co-creating your conscious uncoupling, and setting expectations 

  • Breakup sex?!?!

  • Answering the age-old debate: Can you stay friends?


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 131: Asking For A Friend: How Can I Be An Amazing Manager

Being a manager isn’t easy. (Seriously, just ask Mary Fitzgerald.) Leading a whole team of diverse humans with varying needs and goals can feel super overwhelming. So how do you confidently step into a management role and show others that you've got it figured out, even when you’re drowning in impostor syndrome? We got you.



Being a manager isn’t easy. (Seriously, just ask Mary Fitzgerald.) Leading a whole team of diverse humans with varying needs and goals can feel super overwhelming. So how do you confidently step into a management role and show others that you've got it figured out, even when you’re drowning in impostor syndrome? We got you. 

This week, Cailyn’s jumping into the hot seat as TMHTA's resident people manager to spill the tea on how to be a killer boss, whether you're a first-timer or leading a brand-new team. 

So if you’re looking to avoid an Oppenheim Group situation on your team (just steer clear of brokers opens!), tune in as we chat about:

  • Dealing with imposter syndrome as a first-time manager

  • Setting mutual expectations with your team

  • Why it’s essential to delegate as a manager

  • The key to helping your team thrive

  • How to give constructive feedback 

  • Tips for dealing with conflict among employees 

  • Finding a mentor or coach to guide you


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 129: Teach Me How To Get The Fuck To Sleep, with Sleep Expert Alanna McGinn

The more adulting we do, the more we realize how essential getting good quality sleep is to literally every aspect of our lives. From our physical health to our mood and mindset, sleep is the key to solving a whole lot of our problems. We’re sick of burning the candle at both ends and tossing and turning each night, and we’re not alone: the past few decades have seen a downward trend in the quality and quantity of sleep that people are getting. So… let’s talk about sleep, baby!



The more adulting we do, the more we realize how essential getting good quality sleep is to literally every aspect of our lives. From our physical health to our mood and mindset, sleep is the key to solving a whole lot of our problems. 

We’re sick of burning the candle at both ends and tossing and turning each night, and we’re not alone: the past few decades have seen a downward trend in the quality and quantity of sleep that people are getting. So… let’s talk about sleep, baby! 

We’re clearly not the experts on this (read sleep-deprived), so we called in Alanna McGinn. Alanna is the founder and lead sleep expert at Good Night Sleep Site, host of the ‘This Girl Loves Sleep’ podcast and author of ‘This Baby Loves Sleep’. Alanna and her team of sleep consultants are certified through The Family Sleep Institute and have helped thousands of families around the world overcome their sleep challenges and establish healthy nighttime habits. Alanna is the resident sleep expert for publications like Forbes, Maclean’s and Today’s Parent, and the media sleep expert on Cityline, Breakfast Television, CBC Radio, and more. 

Join us as we chat about:

  • The mental and physical impact of sleep deprivation

  • Creating a routine that supports healthy sleep

  • Why your morning wakeup is the most important factor to good sleep

  • How to figure out the amount of sleep we really need

  • Tricks to optimize our sleep cycles and REM sleep 

  • Realtalk on magnesium and natural remedies 

  • How to catch up after an all-nighter and adjust to new timezones 

  • Can we keep napping???

  • The power of the napuccino 

We hope this episode helps you create healthy sleep habits so you can get the quality sleep you deserve!

Follow Alanna:

goodnightsleepsite.com
@gnsleepsite
@alanna.mcginn


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 127: The Quickie: How To Eat Nutritiously On A Budget

Apparently, a big part of adulting is learning how to feed yourself, but with all the expensive health foods and skyrocketing grocery prices, eating well can feel financially overwhelming. So this week we’re talking about how to balance our nutrition without breaking the bank, because if we’ve learned anything on our wellness journeys, it’s that there is no one-size-fits-all solution for healthy eating and finding what works for your body can have a huge impact on how you feel.



Apparently, a big part of adulting is learning how to feed yourself, but with all the expensive health foods and skyrocketing grocery prices, eating well can feel financially overwhelming. So this week we’re talking about how to balance our nutrition without breaking the bank, because if we’ve learned anything on our wellness journeys, it’s that there is no one-size-fits-all solution for healthy eating and finding what works for your body can have a huge impact on how you feel. 

Whatever your health goals are, we should all aspire to a solid balance of protein, healthy fats, and fibre at every meal—and it doesn’t have to cost your whole paycheck. Join us as we get back to the basics on a budget!

Tune in as we chat about:

  • Myth-busting expensive health foods

  • The healthy changes Gill and Cailyn have made

  • Easy ways to keep costs down with meal-planning

  • How to hack your grocery shopping 

  • Getting the most out of what you make

  • The benefits of growing your own food

We hope this episode inspires you to keep that wallet and booty thick on your pursuit of healthy eating! Special thanks to Clover Leaf Flavoured Tuna for sponsoring today’s episode. Check out cloverleaf.ca for delicious and easy recipe ideas.


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 125: Teach Me How To Have Difficult Conversations | Part 2, with Anna Sale, Host of Death, Sex & Money

We’re back with more of our conversation on hard conversations with the fabulous Anna Sale. This week we’re leaving our comfort zones behind and learning how to confront our mess head-on, for the good of our relationships and our sanity. From finances to family dynamics and grief, we’re getting all the tips on how to approach the most hush-hush topics and have the courage to admit when the status quo isn't good enough anymore.



We’re back with more of our conversation on hard conversations with the fabulous Anna Sale. This week we’re leaving our comfort zones behind and learning how to confront our mess head-on, for the good of our relationships and our sanity. From finances to family dynamics and grief, we’re getting all the tips on how to approach the most hush-hush topics and have the courage to admit when the status quo isn't good enough anymore.

Anna is the creator and host of WNYC studios’ wildly popular and award-winning Death, Sex, & Money podcast, where she's been doing interviews about "the things we think about a lot and need to talk about more" since 2014. 

The New York Times dubbed her “a therapist at happy hour”, and we could not agree more. Anna and her guests have direct thought-provoking conversations about the topics we’re often too squeamish, polite, or nervous to bring up. She’s the author of Let’s Talk About Hard Things, where she dives into death, sex, money, family, and identity. 

Join us as we dive into:

  • Why money feels so taboo to talk about

  • How to navigate financial differences with friends and family

  • Addressing family conflict in a constructive way

  • Knowing when it’s time to take a break from someone

  • How to support someone who is dealing with grief

We hope this episode reminds you that you can do hard things!

Listen to part 1 of our conversation with Anna here!


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 123: Teach Me How To Have Difficult Conversations | Part 1, with Anna Sale, Host of Death, Sex & Money

Calling all our non-confrontational queens, this one’s for you! If you’ve ever avoided or put off a difficult conversation (you know the one), you’re not alone. We all struggle with confronting tough issues head-on in fear of being judged, shamed or rejected for expressing how we feel. But here's the thing – shying away from the hard, messy stuff means that we're leaving key parts of ourselves out of our most important relationships. So, it's time to learn how to navigate tough talks with confidence and grace!



Calling all our non-confrontational queens, this one’s for you! If you’ve ever avoided or put off a difficult conversation (you know the one), you’re not alone. We all struggle with confronting tough issues head-on in fear of being judged, shamed or rejected for expressing how we feel. But here's the thing – shying away from the hard, messy stuff means that we're leaving key parts of ourselves out of our most important relationships. So, it's time to learn how to navigate tough talks with confidence and grace!

Thankfully we called in someone who has literally written the book on hard conversations, Anna Sale. Anna is the creator and host of WNYC studios’ wildly popular and award-winning Death, Sex, & Money podcast, where she's been doing interviews about "the things we think about a lot and need to talk about more" since 2014. 

The New York Times dubbed her “a therapist at happy hour”, and we could not agree more. Anna and her guests have direct thought-provoking conversations about the topics we’re often too squeamish, polite, or nervous to bring up. She’s the author of Let’s Talk About Hard Things, where she dives into death, sex, money, family, and identity. 

Join us for a deep convo about: 

  • Why tough conversations are so necessary

  • What really holds us back from talking about difficult or taboo topics

  • The anatomy of a productive, hard conversation (and how to prepare for it)

  • Why good conversations don’t always lead to tidy resolutions

  • Why hard conversations with family can be so much more difficult

  • Advice for avoidant and anxious people to get better at direct communication

  • Anna’s take on radical honesty and the use of fibbing in relationships

  • How to “pick your battles” and decide when a big discussion is warranted

Be sure to tune in next week for part 2 of our chat! 

We hope this episode helps you have the honest, hard conversations that can help us connect more deeply. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 121: Asking For A Friend: How Can I Prepare For Labour And What’s Childbirth Really Like

Unlike labour, this week’s Asking For A Friend episode is a quickie and we’re getting real on giving birth! From birth plans to hospital bags, labour pains to pelvic floor prep, we’ve got TMHTA’s resident mom, Cailyn, in the hot seat to get all the juicy details on the highs and lows of creating life.



Unlike labour, this week’s Asking For A Friend episode is a quickie and we’re getting real on giving birth! From birth plans to hospital bags, labour pains to pelvic floor prep, we’ve got TMHTA’s resident mom, Cailyn, in the hot seat to get all the juicy details on the highs and lows of creating life.

As the saying goes, “You don’t know until you know,” and that’s especially true in the case of labour and delivery. Birth, like so much of life, rarely goes the way we plan, but being prepared mentally and physically can help lessen anxiety and stress on your big day. There are a lot of opinions on what the ‘best’ way to give birth is, but at the end of the day, getting mom and baby through it safely is the only thing that matters...so do you boo! 

Tune in as we chat about:

  • Coping with anxiety about going into labour

  • Telling your partner/support team what you need 

  • How strengthening your pelvic floor can help during labour

  • Advocating for yourself in the delivery room

  • Making a birth plan, but keeping an open mind

  • Meditation and breathwork apps to help you through contractions

  • Cailyn's experience getting an epidural 

  • Hospital bag essentials you'll want to have

  • The scoop on poop during childbirth

  • The healing process post-delivery

If you have any burning questions for us and you want to get us in the hotseat, DM or email us your Qs at contact@teachmehowtoadult.ca and we’ll dive into them in an upcoming Asking For A Friend. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 119: How To Make Sustainable And Eco-Friendly Changes (That Are Actually Doable), with Julia Grieve

Tbh, it can be overwhelming trying to be more environmentally conscious with all the things we're “supposed” to be doing. Between recycling, conserving water, composting, and reducing waste, it feels like we're just not doing enough. But here’s the thing: it’s less about being the perfect environmentalist and more about finding sustainable swaps that work with your lifestyle — progress over perfection!



Just in time for Earth Day, it’s the perfect time to start reevaluating our consumption habits and doing our part to protect the planet. 

Tbh, it can be overwhelming trying to be more environmentally conscious with all the things we're “supposed” to be doing. Between recycling, conserving water, composting, and reducing waste, it feels like we're just not doing enough. But here’s the thing: it’s less about being the perfect environmentalist and more about finding sustainable swaps that work with your lifestyle — progress over perfection!

So today, we’re getting the tea from the accidental environmentalist herself, Jules Grieve, for an honest, realistic and straight-up sustainable approach to how we can all live greener.

Julia is a TV personality, entrepreneur, fashion designer, former international model, and founder of the incredible Preloved, North America’s leading sustainable fashion brand that has diverted over a million sweaters from landfills. 

 She’s CityLine’s eco expert and regularly appears on Global News and in Canada’s biggest media outlets. Her mission is to show people how simple changes, over time, can have a huge impact, and she’s showing the world how we can take an eco-friendly approach to home design, health, food, fashion and lifestyle. 

Tune in as we chat about:

  • How Julia became an “accidental environmentalist” and started Preloved

  • Julia’s fave sustainable swaps that anyone can make

  • Tips for cutting out plastic and reducing your waste

  • Working towards a circular economy 

  • Ways to repair, upcycle, and thrift to extend the lifecycle of our things 

  • Hacks for cutting down on food waste (and keeping those avocados fresh!) and the truth about recycling 

  • Why its key to be mindful of your water consumption

We hope this episode helps inspire you to take small sustainable actions that will help protect this beautiful planet. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 117: The Quickie: How To Save Money And Budget Better | Rerelease

Spring has arrived, and just like the flowers outside, your finances deserve to bloom and flourish this season too! But with interest rates and inflation on the rise, saving money can feel like we’re all trying to swim upstream. So this week we’re throwing it back to an oldie but a goldie where we dive into some easy ways to save money and budget better, literally starting today! Because adulting just hits differently when you have your financial shit together.



Spring has arrived, and just like the flowers outside, your finances deserve to bloom and flourish this season too! But with interest rates and inflation on the rise, saving money can feel like we’re all trying to swim upstream.

So this week we’re throwing it back to an oldie but a goldie where we dive into some easy ways to save money and budget better, literally starting today! Because adulting just hits differently when you have your financial shit together.

Tune in to get the financial scoop on:

- Understanding your spending triggers

- Investing in everyday items

- Why negotiating with cash is King

- How to save on your fave clothes each season

- Automating your banking to help you save 

- Hacking your utility bill

- How to avoid paying annual fees on credit cards

- Tips on getting a higher interest rate on your savings account

- What Gill and Cailyn both realized they need to cut back on

We hope this episode inspires you to save a little money and achieve all of your financial dreams! 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 116: How to I Balance It All And Prioritize — Without The Overwhelm And Guilt?

In the words of Sharpay Evans “I want it all!” and we’re conditioned to believe that we should have it all — a career, a family, good health, a social life, nice things, without having to give anything up. But let’s be honest, our time and energy are finite resources and everything in life comes with tradeoffs. So the real key to “balance” is figuring out what you want to prioritize right now, and what can take the backseat.



In the words of Sharpay Evans “I want it all!” and we’re conditioned to believe that we should have it all — a career, a family, good health, a social life, nice things, without having to give anything up. But let’s be honest, our time and energy are finite resources and everything in life comes with tradeoffs. So the real key to “balance” is figuring out what you want to prioritize right now, and what can take the backseat.  

This week we’re tackling a question about how to balance and prioritize everything when you’re feeling overwhelmed and stretched too thin. Juggling work, family and friends can leave us feeling like we aren’t succeeding at any of it, but it’s time to give ourselves a little grace and accept the season that we’re in. 

Join us as we chat about:

  • The myth of having it all and the truth about balance

  • The “seasons” Gill and Cailyn are currently in

  • The best advice from Shonda Rhimes

  • The difference between “legitimate overwhelm” and “lifestyle overwhelm” 

  • Mel Robbins’ antidote to overwhelm

  • Identifying lies we tell ourselves

  • How to actually prioritize 

You *can* have it all. Just not all at once. Let the journey unfold as you become ready for it. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 114: How To Say “No” To Get More Of What You Really Want

This might come as a surprise, but telling people “no” isn’t actually one of the seven deadly sins. Here’s what actually happens when you say “no” to things you don’t align with that consistently drain you: You open up all of the doors for the “HELL YES” opportunities to come flooding in!



This might come as a surprise, but telling people “no” isn’t actually one of the seven deadly sins. Here’s what actually happens when you say “no” to things you don’t align with that consistently drain you: You open up all of the doors for the “HELL YES” opportunities to come flooding in!

But if you’re anything like us and tend towards people pleasing, creating boundaries can feel foreign. And that inherent desire to avoid conflict and keep the peace can often do more harm than good. That’s why we’ve committed to learning how, and when, to prioritize our own needs, so we can show up as our best selves for all the wonderful things we say yes to. Because we can’t do it all, and our time and energy are finite resources. 

There's a lot of talk, and a lot to be said, for the power of Yes, but No hasn’t gotten the same star treatment and we think it’s time to change that. From increasing productivity and preventing burnout to building healthy relationships, this week we’re giving “No” the rebrand it deserves!

Join us as we chat about:

  • Overcoming the need to people-please

  • How to rewire your brain to make different decisions

  • Our one exception for avoiding “no” 

  • The ways no has changed our lives and opened new doors

  • How to set healthy boundaries and communicate effectively

  • Tips for getting better at saying no

  • The importance of honesty and vulnerability 

  • The 3 questions to help you make any decision

We hope this helps you harness the power of doing less shit that you don’t enjoy, so you can make space for all the stuff that’s worth it.


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 112: Asking For A Friend: How Do I Navigate Friendships When We’re All In Different Life Stages?

As we go through our 20s and 30s, we all start adulting in different ways and at different rates, and maintaining our ride-or-die connections can start to feel complicated. Navigating these different life stages means that our friendships sometimes end up at the bottom of the list, or we start growing in different directions and losing common ground. But every friendship goes through different seasons, and change doesn’t need to be a bad thing!



Picture this: You just turned 30. One friend just bought a home, while another is traveling the world. One is starting their own business, and one is skyrocketing up the corporate ladder. Some are getting married and having babies, and some are single AF. None of us can decide on a date to catch up, and where to go for dinner. So no one told you life was gonna be this way… 

As we go through our 20s and 30s, we all start adulting in different ways and at different rates, and maintaining our ride-or-die connections can start to feel complicated. Navigating these different life stages means that our friendships sometimes end up at the bottom of the list, or we start growing in different directions and losing common ground. But every friendship goes through different seasons, and change doesn’t need to be a bad thing! 

This week we’re tackling two juicy Qs: How to maintain our friendships when we’re at different life stages, and how to deal with comparison when those big milestones crop up. 

Join us as we chat about:

  • How to stop comparing and start leading with curiosity

  • Getting rid of timelines and expectations for where you *should* be 

  • Navigating feelings of isolation during a big life change

  • Why it’s as important to be there in the good times as it is in the bad

  • Celebrating your friend’s wins like they’re your own

  • Giving your friends the space to change and grow

  • Finding new ways to make memories together

  • How to communicate and self-regulate when your friendship dynamics shift

  • Bringing your people along for the journey

No matter where you’re at in life, your closest friendships are worth nurturing — they’re the family we get to choose! — and we’re choosing to fight for them. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 110: How To Be More Compassionate Towards Yourself And Others

We humans are social creatures, we thrive on community and connection. But in these times of social media comparison and cancel culture, it can feel like we’ve lost sight of something vital — compassion. With mean girls dominating the news cycle, we thought this would be the perfect time to get deep and teach ourselves a lesson on the importance of compassion, how to give it to others and most importantly, how to give it to ourselves.

At its core, compassion is about putting aside judgment and making an effort to understand the struggles within ourselves and others. It helps us create meaningful connections, build healthy relationships, and develop emotional intelligence, which coincidentally all make for a well-adjusted adult! We’re all a lot more similar than we are different so let’s get positive (but not in a toxic way we promise).



We humans are social creatures, we thrive on community and connection. But in these times of social media comparison and cancel culture, it can feel like we’ve lost sight of something vital — compassion. With mean girls dominating the news cycle, we thought this would be the perfect time to get deep and teach ourselves a lesson on the importance of compassion, how to give it to others and most importantly, how to give it to ourselves.

At its core, compassion is about putting aside judgment and making an effort to understand the struggles within ourselves and others. It helps us create meaningful connections, build healthy relationships, and develop emotional intelligence, which coincidentally all make for a well-adjusted adult! We’re all a lot more similar than we are different so let’s get positive (but not in a toxic way we promise). 

Tune in as we chat about:

  • What compassion actually means

  • The difference between pity, sympathy, empathy and compassion

  • The importance of finding similarities with others

  • How assuming positive intent can shift your mindset

  • Why we should validate someone before trying to find solutions

  • How to hold space for someone's pain

  • Using the "RAIN" method to cultivate self-compassion

  • Gill's favourite Loving-Kindness mediation for next-level compassion

We hope this episode helps you have more compassion for the people in your life, but most importantly, for yourself.


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 108: Teach Me How To Plan My Dream Wedding (Without All The Stress), with Wedding Planner Rebecca Chan

Wedding season will soon be upon us, and if you’re planning to tie the knot, dreaming up a future wedding, or supporting a bride/groom in your life — this one’s for you. Whether you’re planning the event of the year, or an intimate and budget-friendly micro-celebration, every single wedding is a beautiful opportunity to celebrate love, so don’t lose sight of what’s important.

But no matter the scale or scope, weddings can be stressful, so we got the inside scoop from luxury wedding planner Rebecca Chan. Rebecca is the owner and lead planner of Rebecca Chan Weddings & Events, which specializes in planning beautiful, luxury weddings and events in Toronto and abroad. She’s been orchestrating stunning events for over a decade and is a regular Cityline guest expert. She’s even planned events for celebrities like Rupi Kaur!



Wedding season will soon be upon us, and if you’re planning to tie the knot, dreaming up a future wedding, or supporting a bride/groom in your life — this one’s for you. Whether you’re planning the event of the year, or an intimate and budget-friendly micro-celebration, every single wedding is a beautiful opportunity to celebrate love, so don’t lose sight of what’s important. 

But no matter the scale or scope, weddings can be stressful, so we got the inside scoop from luxury wedding planner Rebecca Chan. Rebecca is the owner and lead planner of Rebecca Chan Weddings & Events, which specializes in planning beautiful, luxury weddings and events in Toronto and abroad. She’s been orchestrating stunning events for over a decade and is a regular Cityline guest expert. She’s even planned events for celebrities like Rupi Kaur!

So if you're ready to say "I do,” tune in as we chat about:

  • Planning for the wedding that YOU want

  • Getting clear on what matters most

  • The big-ticket items you need to plan for

  • Hidden fees you might not know about

  • How to navigate the guest list and avoid hurt feelings

  • Subtle ways to ask for cash instead of gifts

  • Pro tips for having the perfect timeline on the day of your wedding

  • When you should start dress shopping

  • Qs to ask when finding the perfect venue 

We hope this episode helps you plan the wedding of your dreams, minus all the nerves and overspending. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 106: Asking For A Friend: How Do I Prepare For Pregnancy (The Good, The Bad & The Mood Swings)?

If you’re starting to think about having a bébé, or newly expecting (congrats!), it’s totally normal for a laundry list of Qs — like, WTF IS THIS GOING TO FEEL LIKE!? — to start building up. The unknowns can feel daunting, and there are so many aspects of pregnancy that still aren’t openly talked about. Like the whole nipple situation.

Luckily for us, Cailyn tried out pregnancy for nine whole months, all so that we may benefit from her experiences and advice. Buckle up, because our resident mama is here to spill the tea on everything she learned during pregnancy.



If you’re starting to think about having a bébé, or newly expecting (congrats!), it’s totally normal for a laundry list of Qs — like, WTF IS THIS GOING TO FEEL LIKE!? — to start building up. The unknowns can feel daunting, and there are so many aspects of pregnancy that still aren’t openly talked about. Like the whole nipple situation. 

Luckily for us, Cailyn tried out pregnancy for nine whole months, all so that we may benefit from her experiences and advice. Buckle up, because our resident mama is here to spill the tea on everything she learned during pregnancy.  

Join us as we chat about:

  • How to know if you’re ready to start trying for a baby

  • WTF to do when you first find out you’re pregnant

  • Debunking the narrative that you should wait three months to tell people

  • How to approach telling your boss that you’re pregnant

  • Wild pregnancy symptoms you may not know about

  • How to know if you're doing all the right things

  • Having compassion for yourself and your body

  • The honest scoop on how Cailyn’s body changed

  • The best pregnancy advice Cailyn received 

Stay tuned for our upcoming deep-dives into fertility, labor, postpartum realtalk, and life with a baby! Wherever you are in your pregnancy/fertility journey, we hope you have all the support and love you deserve during this incredible time in your life.  

If you have any burning questions for us and you want to get us in the hotseat, DM or email us your Qs at contact@teachmehowtoadult.ca and we’ll dive into them in an upcoming Asking For A Friend. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 104: Teach Me How To Communicate Better In My Relationship, with Therapist Liz Earnshaw

Good communication is the golden key to a healthy relationship, but like most things, it’s easier said than done. So today, we’re continuing our love month theme and throwing it back to a collection of game-changing advice from our episode on communication and conflict with licensed family and marriage therapist, Liz Earnshaw.

Liz takes us on a relationship deep dive, breaking down everything from our physiology during conflict, to identifying power dynamics and creating healthy communication strategies. And even if you’re not in a relationship, this episode can help anyone work towards becoming the securely attached communicative human we all strive to be.



Good communication is the golden key to a healthy relationship, but like most things, it’s easier said than done. So today, we’re continuing our love month theme and throwing it back to a collection of game-changing advice from our episode on communication and conflict with licensed family and marriage therapist, Liz Earnshaw.

Liz takes us on a relationship deep dive, breaking down everything from our physiology during conflict, to identifying power dynamics and creating healthy communication strategies. And even if you’re not in a relationship, this episode can help anyone work towards becoming the securely attached communicative human we all strive to be.

Tune in as we chat about:

  • The biggest relationship issues she sees in couples 

  • How The Four Horsemen can harm the way we communicate 

  • Dealing with criticism and feedback

  • How to heal from hurt or betrayal 

  • The power struggles that crop up during conflict 

  • How to set healthy boundaries with your partner 

We hope this episode helps you create closer bonds and communicate effectively in conflict!


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 103: Asking For A Friend: What Are Some Major Red & Green Flags In A Relationship?

A wise person once said, love is blind. But let's be real…sometimes love can be straight up oblivious! Whether you’re single and dating or in a long-term relationship, green flags and red flags always seem to come up as signs that things are either going great, could use some work, or that it’s time to GTFO.

So, today we’re tackling a question that a lot of our friends and listeners have been talking about lately — how to spot a red or green flag in a relationship, and what to do when those red flags start adding up. Pour yourself a glass of your favourite bevy (it’s a fun one!) and join us as we read, rate, and drink our way through the red and green flags you DM’d us on IG, and discuss/debate how good or bad each scenario really is.



A wise person once said, love is blind. But let's be real…sometimes love can be straight up oblivious! Whether you’re single and dating or in a long-term relationship, green flags and red flags always seem to come up as signs that things are either going great, could use some work, or that it’s time to GTFO. 

So, today we’re tackling a question that a lot of our friends and listeners have been talking about lately — how to spot a red or green flag in a relationship, and what to do when those red flags start adding up. Pour yourself a glass of your favourite bevy (it’s a fun one!) and join us as we read, rate, and drink our way through the red and green flags you DM’d us on IG, and discuss/debate how good or bad each scenario really is.

Tune in to hear our thoughts on: 

  • Staying friends with their ex

  • When they’re jealous AF

  • Bad texters 

  • When they want to do everything together

  • When they’re a Mama’s boy

  • What constitutes good VS bad fighting

  • When they’re extra cheesy & write you love letters, songs and poems 

  • Low libidos 

  • Love bombing

  • And more!!

We hope this episode helps you navigate any potential red flags that come your way and helps you find the love you deserve. If you have any burning questions for us and you want to get us in the hotseat, DM or email us your Qs at contact@teachmehowtoadult.ca and we’ll dive into them in an upcoming Asking For A Friend. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 101: How To Navigate Attachment Styles And Create Secure Relationships, with psychotherapist Jessica Baum

Hello lovers and friends, we’re back just in time for Valentine’s day with an episode that might just solve all your relationship blues (even if you’re just dating you!). This week we’re digging into the four attachment styles — what they are, how they show up in relationships, and how to navigate them like a thoroughly therapized pro.

Whether you’re aware of them or not, everyone has repeated patterns and automatic responses that crop up in their love life. Sometimes those reactions aren’t healthy, but luckily for us, we can do the work to create security and stability. That’s where attachment styles come in — the four attachment styles (secure, anxious, avoidant, disorganized) are influenced by our formative years, and they characterize how we interact and behave in relationships as adults.



Hello lovers and friends, we’re back just in time for Valentine’s day with an episode that might just solve all your relationship blues (even if you’re just dating you!). This week we’re digging into the four attachment styles — what they are, how they show up in relationships, and how to navigate them like a thoroughly therapized pro. 

Whether you’re aware of them or not, everyone has repeated patterns and automatic responses that crop up in their love life. Sometimes those reactions aren’t healthy, but luckily for us, we can do the work to create security and stability. That’s where attachment styles come in — the four attachment styles (secure, anxious, avoidant, disorganized) are influenced by our formative years, and they characterize how we interact and behave in relationships as adults.

But any attachment anxieties that crop up can be healed, and we called in Jessica Baum (who literally wrote the book on anxious attachment) to help! Jessica is a psychotherapist and couples counselor, founder of The Relationship Institute of Palm Beach, and the founder of Be Self-full®, a company that provides counseling, group coaching and courses for couples and individuals. 

This is a juicy one, so join us as we discuss:

  • The four attachment styles and how they show up in relationships

  • How your childhood influences your attachment style

  • Ways your attachment style plays into chemistry and  attraction

  • Strategies for self-soothing and working towards secure attachments 

  • Self-regulating vs co-regulation with your partner

  • What a codependent relationship might look like 

  • The key to supporting your partner’s attachment style

We hope this episode helps you create secure attachments and prioritize self-improvement. In case we don’t say it enough, we love you!

Take Jessica’s quiz to find out what your attachment style is!

Follow Jessica:

@jessicabaumlmhc

Beselffull.com

Buy Jessica’s book Anxiously Attached: Becoming More Secure in Life and Love


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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Episode 99: Asking for a friend: how do I date my damn self?

It’s officially the month of love (and the unofficial Miley-buy-yourself-flowers month!), so we’re kicking it off with an episode dedicated to the real love of our life – ourselves! It’s easy to get so focused on dating and romance, that we forget about the importance of self-love, and we’re ready to change that.

Whether you’re feeling lonely or single, or craving some you-time in your relationship, learning to date yourself is a practice that can literally change your life. Because the way you treat yourself will impact the love you attract and the future fulfillment you feel. 



It’s officially the month of love (and the unofficial Miley-buy-yourself-flowers month!), so we’re kicking it off with an episode dedicated to the real love of our life – ourselves! It’s easy to get so focused on dating and romance, that we forget about the importance of self-love, and we’re ready to change that.

Whether you’re feeling lonely or single, or craving some you-time in your relationship, learning to date yourself is a practice that can literally change your life. Because the way you treat yourself will impact the love you attract and the future fulfillment you feel. 

And this isn’t just for the singles! Learning to fulfill your own needs, take yourself out, and romanticize your day-to-day will positively affect all your relationships, and it starts with showing up for your damn self. Luckily, Gill has been on a self-love journey through singledom and solo living, and she’s here to spill the tea on everything she’s learned along the way. 

So if you’re ready to enter your Miley era, join us as we chat about:

  • What dating yourself *actually* means

  • Why it’s time to stop putting your life on hold

  • Reclaiming your alone time and reframing loneliness

  • How to take yourself on a solo date 

  • Ways to romance yourself in the day-to-day

  • Why you should be giving yourself your love language 

  • The deep inner work that will increase self-compassion and self-love 

We hope this episode inspires you to hold your own damn hand and start prioritizing YOU! If you have any burning questions for us and you want to get us in the hotseat, DM or email us your Qs at contact@teachmehowtoadult.ca and we’ll dive into them in an upcoming Asking For A Friend. 


If you have a topic you’d like us to cover or a guest you want us to interview, comment or DM us on Instagram:

@teachmehowtoadultpodcast

@cailynmichaan 

@yunggillianaire


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