Lifestyle, Career Cailyn and Gillian Lifestyle, Career Cailyn and Gillian

Episode 42: How To Stop Overthinking Everything

If you’re an overthinker like us, worrying about the future, dwelling on the past, and overanalyzing every single decision can be totally paralyzing in your day-to-day life. Overthinking can make decision-making impossible, and it can create tons of unnecessary stress that holds us back from living a life we truly want. And TBH, it’s usually all over nothing!



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If you’re an overthinker like us, worrying about the future, dwelling on the past, and overanalyzing every single decision can be totally paralyzing in your day-to-day life. Overthinking can make decision-making impossible, and it can create tons of unnecessary stress that holds us back from living a life we truly want. And TBH, it’s usually all over nothing!

But today can literally be the day you take control of your thoughts rather than letting your thoughts control you. Spiralling thought patterns are learned, and they can also be unlearned. The key is just to identify what’s triggering your overthinking, and then work on changing your mindset. In this week’s episode we have tons of expert and research-backed advice on how to do exactly that.  

Tune in as we chat about:

  • The difference between ruminating vs worrying 

  • Why learning to just act and “think less, do more” can change your life and propel you forward

  • Why you should carve out designated time to overthink/worry

  • How to rewrite the stories you are telling yourself in your head

  • Tricks for taking back control over your thoughts 

  • Tips for challenging perfectionism

  • The 10/10/10 test for gaining perspective

  • How simple mindfulness practices can calm your racing mind

We hope this episode helps you take control of your thoughts! If you have tried and true tactics for stopping those overthinking spirals, we would LOVE to hear them, so DM us if there’s something else that’s worked for 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 41: How To Buy Or Rent Your Next Home

The housing market is absolutely insane in North America right now, especially in the major cities of Canada (helllllo, Toronto and Vancouver). The market is hotter than ever, and Canadian house prices and home sales hit record highs this March. So in today’s quickie, we’re diving into everything you need to know to navigate renting or buying your next home.



The housing market is absolutely insane in North America right now, especially in the major cities of Canada (helllllo, Toronto and Vancouver). The market is hotter than ever, and Canadian house prices and home sales hit record highs this March. So in today’s quickie, we’re diving into everything you need to know to navigate renting or buying your next home. 

Whether you’re moving out into a rental for the first time or thinking about taking the plunge and buying real estate, there’s a lot to consider that can help you with your decision. Hosts Cailyn and Gillian bring their different experiences and perspectives as renters and homeowners to offer up realtalk on the process and logistics of landing your next home. 

It’s daunting AF, but there’s still a ton of hope. It’s a good time to rent right now since we’re in a renter’s market, and if you’re looking into homeownership, interest rates are super low for the time being. 

 Tune in as we chat about:

  • Trends in the Canadian real estate market, and how much buying a home or renting a condo could set you back in major cities

  • How to decide between renting and buying based on your goals, values and finances (and the pros and cons of each)

  • The % of your income you should be sending on your home

  • The importance of location and neighbourhood

  • The team of real estate agents, mortgage brokers and lawyers you’ll need in your corner

  • Everything you need to know about mortgages, explained 

  • The hidden and unexpected costs of buying a home that you should prep for

  • The process from submitting an offer to picking up the keys on your closing date

  • The requirements checklist you should use for finding your ideal rental

  • How to negotiate your rent like a boss

  • The paperwork, proof and process you’ll need to secure your rental home

We hope this episode helps you in your search for the perfect rental or your first home. Happy house-hunting, 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 40: How To Love Yourself More

If you have an idea that you can’t stop dreaming about, this week’s episode is the inspo you need. We chat with Ashley Freeborn, the founder and CEO of the renowned fashion brand Smash + Tess, about all things brand building, entrepreneurship, using fear to fuel your fire, and tapping your network to help get your idea off the ground.

You’ve probably seen people rocking Ashley’s rompers on instagram, or heard about her epic collabs with Jillian Harris, Sarah Landry of The Birds Papaya and Hilary Duff, just to name a few. Her brand started the #romperrevolution but here’s why we honed in on Smash + Tess for today’s episode: Ashley isn’t a serial entrepreneur or longtime business or fashion mogul, she just had an idea to fill a gap in the market, and made her dream a huge reality. What she created is so much more than a clothing company, it’s a community, a lifestyle and an inclusive brand that empowers women to live their best lives.


This episode is brought to you by Dove


Roxy Earle

Vaxxed girl summer is in full swing, and there’s so much good energy and hope again! But summer can also be a very triggering time for a lot of people when it comes to body image and insecurities. We polled you guys on Instagram about how you’re feeling in terms of confidence and self-acceptance, and we learned that we’re definitely not alone in this feeling. 76% of you said that summer triggers your insecurities, while 77% of you are feeling anxious about re-emerging from lockdowns with all the physical and mental changes we’ve undergone. 91% of you said that you struggle with negative self-talk, and we feel you...we can all be our own worst critics and bullies.

That’s why we called in body positivity activist and the Queen of confidence, Roxy Earle. We’re on a mission to help everyone (including ourselves) positively develop the single most important relationship we’ll ever have — our relationship with ourselves. And that requires unconditional self-love, compassion, gratitude and some helpful tools to get us out of negative spirals when we’re struggling with our self-esteem or body image. 

Roxy is a former marketing professional turned model, entrepreneur, body positivity activist and a star on Real Housewives of Toronto. She started the #MySizeRox movement, which advocates that confidence comes in all shapes and sizes. She’s worked with brands like Knix, H&M, Le Chateau and Joe Fresh to bring more inclusive sizing and styles to their stores, and is launching the Ana App, which is a tool to increase positivity & confidence while also optimizing your health. 

Tune in as we chat about:

  • Gill’s mindset shift for dealing with negative spirals, finding pride and respect in herself, and abandoning clothing sizes

  • Cailyn’s newfound outlook on self-love & body image as a soon-to-be mom

  • The moment that inspired Roxy to start the #MySizeRoxs movement

  • How confidence became her secret sauce and how to cultivate it (hint: it’s not genetic, it’s accountability!)

  • Roxy’s tips for practicing positive self-talk and self-love daily

  • Why Roxy is advocating for inclusivity and representation in the fashion industry

  • How a gratitude practice can help you combat insecurities and change your life

  • Why filters and body contouring apps are unattainable, exhausting and quite honestly...boring!

  • The mindset shift to have a healthier relationship with your body

  • The importance of practicing and modelling self-love as a parent

  • The #1 tip for looking and feeling your best in photos

We hope this episode inspires you to wear the damn shorts this summer and to start loving yourself unconditionally. You deserve it. And if you need any support on your self-love journey, we’re here for you.


Follow Roxy:

@luxuriousroxy

Get the Ana App (coming soon): 

instagram.com/theanaapp/


This episode is brought to you by Dove. Visit teachmehowtoadult.ca/dove for details on how to try a free sample of their Deep Moisture Hand Sanitizer that we can’t stop raving about!


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 39: How To Have An Adult AF Home

A big part of levelling up in adulthood for us has been moving past those university-dorm-room living habits and creating an actual adult home. Because anyone who’s ever called their parents asking for laundry tips or cooking questions knows...adulthood hits differently when you have your sh*t together at home!

So this is your quick and dirty guide to all the kitchen tools you *actually* need now that you’re adulting, the scoop about everything from pans and knives, to linens and laundry, grown-ass bedding and those fancy touches that will make your space functional and elevated. Are laundry tips sexy? No. Are we all trying to figure this stuff out? Yes. We hope this episode shows you that you DON’T need to wait for a wedding registry to get nice things that make you feel at home where you live, because even small investments in yourself and how you live can make a huge difference in your happiness and efficiency.


This episode is brought to you by Dove


Adult AF Home.jpeg

A big part of levelling up in adulthood for us has been moving past those university-dorm-room living habits and creating an actual adult home. Because anyone who’s ever called their parents asking for laundry tips or cooking questions knows...adulthood hits differently when you have your shit together at home!

So this is your quick and dirty guide to all the kitchen tools you *actually* need now that you’re adulting, the scoop about everything from pans and knives, to linens and laundry, grown-ass bedding and those fancy touches that will make your space functional and elevated. Are laundry tips sexy? No. Are we all trying to figure this stuff out? Yes. We hope this episode shows you that you DON’T need to wait for a wedding registry to get nice things that make you feel at home where you live, because even small investments in yourself and how you live can make a huge difference in your happiness and efficiency. 

And even though we’re covering a lot of things that you can buy for your place, we just want to flag that today’s advice isn’t all about spending a lot of money and acquiring a bunch of stuff. This can all be really budget-friendly, so wherever you’re at with your living situation and your budget, and whether you rent or own, know that you can follow these tips with super limited savings!

Tune in as we chat about:

  • The kitchen tools and unexpected appliances that are actually worth it

  • The essential kitchen knives you need and how to care for them

  • The different pans on the market and why we’re cast iron and non-stick fans

  • Fancy dishware, glassware and barware for your home

  • Why a good, luxurious bed is the best investment you can make 

  • How steamers, air purifiers and humidifiers will change the game in your bedroom (and skincare routine)

  • The lowdown on linens: how many you need, and the right way to launder them

  • How a good couch can make your living room whole and how to get one on a dime

  • The importance of mood lighting and music

  • Which plant babies are the easiest to take care of and will look cute in your home


We hope this episode inspires you to make your home feel like yours, and to invest in easy upgrades that will make all the difference in your grownup space.


This episode is brought to you by Dove. Visit teachmehowtoadult.ca/dove for details on how to try a free sample of their Deep Moisture Hand Sanitizer that we can’t stop raving about!


Products mentioned in this episode:


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 38: How To Grow a Business Through Community & Collabs

If you have an idea that you can’t stop dreaming about, this week’s episode is the inspo you need. We chat with Ashley Freeborn, the founder and CEO of the renowned fashion brand Smash + Tess, about all things brand building, entrepreneurship, using fear to fuel your fire, and tapping your network to help get your idea off the ground.

You’ve probably seen people rocking Ashley’s rompers on instagram, or heard about her epic collabs with Jillian Harris, Sarah Landry of The Birds Papaya and Hilary Duff, just to name a few. Her brand started the #romperrevolution but here’s why we honed in on Smash + Tess for today’s episode: Ashley isn’t a serial entrepreneur or longtime business or fashion mogul, she just had an idea to fill a gap in the market, and made her dream a huge reality. What she created is so much more than a clothing company, it’s a community, a lifestyle and an inclusive brand that empowers women to live their best lives.


This episode is brought to you by Dove


Instagram Episode Drop 3.png

If you have an idea that you can’t stop dreaming about, this week’s episode is the inspo you need. We chat with Ashley Freeborn, the founder and CEO of the renowned fashion brand Smash + Tess, about all things brand building, entrepreneurship, using fear to fuel your fire, and tapping your network to help get your idea off the ground.

You’ve probably seen people rocking Ashley’s rompers on instagram, or heard about her epic collabs with Jillian Harris, Sarah Landry of The Birds Papaya and Hilary Duff, just to name a few. Her brand started the #romperrevolution but here’s why we honed in on Smash + Tess for today’s episode: Ashley isn’t a serial entrepreneur or longtime business or fashion mogul, she just had an idea to fill a gap in the market, and made her dream a huge reality. What she created is so much more than a clothing company, it’s a community, a lifestyle and an inclusive brand that empowers women to live their best lives.

Ashley is a fellow Canadian, who worked as a teacher and then in the finance sector before going all in on her passion project, Smash + Tess. Smash + Tess has since grown from two employees into a team of 40+ in five years, and in 2020, the company achieved 66% YOY growth, surpassing $16.5 million in sales. In 2020, Ashley was named one of Canada’s Top 40 Under 40, led Smash + Tess through their biggest growth year, and was listed in The Globe + Mail’s Top Growth Companies in 2020 – being the #1 woman-led company on the list! She is passionate about creating clothing that celebrates femininity, strength, style, and comfort in women of all shapes and sizes.

Tune in as we chat about:

  • How Ashley made the leap to quit her 9-5 and go all in on Smash + Tess

  • The journey of bringing Smash + Tess from an idea to a best-seller

  • The secret sauce to cultivating a strong community

  • How to use social media as a listening tool for growth

  • Tips for entrepreneurs to overcome impostor syndrome and use fear or rejection as fuel

  • The 3 most important traits to crush it as an entrepreneur

  • How to know when it’s time to go all in on your side hustle

  • Why you don’t necessarily need professional background in the industry you’re breaking into

  • How to avoid burnout as an entrepreneur

  • How to create successful collabs that move the needle

We hope this episode inspires you to pursue that side hustle and Smash (& Tess) all of your biz ideas and goals!


Follow Ashley:

@afreeborn

smashtess.com

@smashtess


This episode is brought to you by Dove. Visit teachmehowtoadult.ca/dove for details on how to try a free sample of their Deep Moisture Hand Sanitizer that we can’t stop raving about!


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 37: How To Start Investing My Money

Sure, #selfcaresundays are good for the soul, but do you know what else feels good? Financial empowerment. So today we’re talking all things investing with millennial money expert, Jessica Moorehouse.

This is one of our most-requested topics and it’s no surprise why. In our recent Instagram poll, 80% of you said that you find investing intimidating — and we totally get that. A lot of us might believe that investing is only for super rich, middle-aged people, but we promise you that is not the case. It is SO key to start investing even the smallest amount while you’re young, so you can reap the benefits of those early investments later on in life. Hello early retirement!


DOVE logo (1) (1).png

This episode is brought to you by Dove


Instagram Episode Drop 3.png

Sure, #selfcaresundays are good for the soul, but do you know what else feels good? Financial empowerment. So today we’re talking all things investing with millennial money expert, Jessica Moorehouse.  This is one of our most-requested topics and it’s no surprise why. In our recent Instagram poll, 80% of you said that you find investing intimidating — and we totally get that. A lot of us might believe that investing is only for super rich, middle-aged people, but we promise you that is not the case. It is SO key to start investing even the smallest amount while you’re young, so you can reap the benefits of those early investments later on in life. Hello early retirement!

And as we learned in this episode, investing isn’t actually *that* complicated, so those who try to make it sound more difficult than it is have some sort of M.O. But we are ready to flip the script on that narrative to start building our financial skillset and investing with confidence!

Jessica is a millennial money expert, speaker, Accredited Financial Counsellor Canada®, award-winning blogger, host of the More Money Podcast and founder of the Millennial Money Meetup, a series of empowering personal finance events. Her mission is to teach others how to take control of their lives by taking control of their money and we are here for that! 

Tune in to hear more about: 

  • The basic investing terminology you should know

  • How to tell when you’re ready to invest

  • The different types of investments people can buy

  • Types of investing accounts you should open

  • How to invest if you don’t have a ton of money

  • Understanding your risk tolerance and creating a balanced portfolio

  • The benefits of investing in increments VS going all in

  • The top 3 things people should look for when investing in a company


Follow Jessica:

jessicamoorhouse.com

@jessicaimoorhouse

More Money Podcast


This episode is brought to you by Dove. Visit teachmehowtoadult.ca/dove for details on how to try a free sample of their Deep Moisture Hand Sanitizer that we can’t stop raving about!


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


Related Episodes:

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Episode 31: How To Crush Your To-Do List and Organize Your Life

If you, like us, have been struggling to cross literally ANYTHING off of your never-ending to-do lists, we are here to help!

In this week’s quickie, we’re giving you tips on how we structure our days (or at least try to), three of the top to-do list methods that pros swear by, and the tools you can use to help you crush all of your goals and leave you worry-free at the end of the day. It all comes down to prioritization.



THE QUICKIE WAVE TO DO.png

If you, like us, have been struggling to cross literally ANYTHING off of your never-ending to-do lists, we are here to help!

There are so many reasons why tackling your to-do list can cause anxiety and overwhelm. If you’re super burnt out right now you could be feeling errand paralysis, or if you’re insanely busy these days, those lists can feel so daunting because EVERYTHING seems urgent. 

So in this week’s quickie, we’re giving you tips on how we structure our days (or at least try to), three of the top to-do list methods that pros swear by, and the tools you can use to help you crush all of your goals and leave you worry-free at the end of the day. It all comes down to prioritization.

Listen along to learn more about:

  • The Ivy Lee Method

  • The Eisenhower Matrix

  • Warren Buffet’s Two List Method

  • Cailyn’s tips for getting through to-do lists

  • Gill’s hot 15-minutes-or-less tip

We hope this episode helps you smash your to-do list and accomplish all of the daily tasks and goals you set out 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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