Lifestyle Cailyn and Gillian Lifestyle Cailyn and Gillian

Episode 143: Asking For A Friend: How Can I Be A Digital Nomad?

For all the sh*t we’ve been through since 2020, there was at least one positive societal change: we entered our remote work era. Not being tied down to an office 5 days a week has afforded us newfound freedom in prioritizing our work-life balance — it’s time to make the most of it. We’ve all dreamed of being able to work and live wherever we want, so let this be the year you shoot your shot. This week we have our resident world traveler, Gill, in the hot seat and she’s finally coming clean on how she’s getting away with all this travel while still killing it in the corporate world.



For all the sh*t we’ve been through since 2020, there was at least one positive societal change: we entered our remote work era. Not being tied down to an office 5 days a week has afforded us newfound freedom in prioritizing our work-life balance — it’s time to make the most of it.

We’ve all dreamed of being able to work and live wherever we want, so let this be the year you shoot your shot. This week we have our resident world traveler, Gill, in the hot seat and she’s finally coming clean on how she’s getting away with all this travel while still killing it in the corporate world. 

Grab a seat, book a plane ticket and buckle in because we’re about to become digital nomads!

Join us as we chat about:

  • The rise of workcations and why you should take one

  • How to choose your travel destinations

  • Navigating work in different timezones

  • Budgeting for your time working abroad 

  • Setting expectations and communicating at work

  • All the logistics you didn’t know you needed

  • How to make the most of balancing work and travel

We hope this episode helps you make your travel dreams a reality!


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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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


Related Episodes:

Read More
Lifestyle Cailyn and Gillian Lifestyle Cailyn and Gillian

Episode 87: How Do I Travel The World On My Own

Taking on the world by yourself can seem overwhelming, but if Eat, Pray, Love taught us anything it’s that solo travel can lead to some of our most liberating, life-changing experiences.

This week we’re diving into one of our most frequently asked questions for our in-house globe trotter, Gill: How do I travel alone? Travelling solo might feel entirely out of your comfort zone, but the benefits of taking time to explore a new place (and yourself) on your own terms can be a serious game-changer for your mental well-being, confidence, and fulfillment. So buckle up, because we’re taking you on a journey through the good, bad, and best parts of flying solo!



Taking on the world by yourself can seem overwhelming, but if Eat, Pray, Love taught us anything it’s that solo travel can lead to some of our most liberating, life-changing experiences. 

This week we’re diving into one of our most frequently asked questions for our in-house globe trotter, Gill: How do I travel alone? Travelling solo might feel entirely out of your comfort zone, but the benefits of taking time to explore a new place (and yourself) on your own terms can be a serious game-changer for your mental well-being, confidence, and fulfillment. So buckle up, because we’re taking you on a journey through the good, bad, and best parts of flying solo!

Join us as we chat about:

  • Gill’s epic trips and why she decided to travel on her own

  • How travelling solo can be healing during hard times

  • The importance of setting an intention for your trip

  • How to keep the vacation sparks alive when you’re back home

  • How to decide where you should go, and when

  • Ways to combat loneliness when you’re on your own

  • Tips for putting yourself out there and meeting new people

  • Planning your trips with “possibilities” vs. a strict itinerary

  • Key safety tips you need to know while travelling solo

  • Gill’s brutal experience getting mugged in Lisbon

  • 3 key tips for anyone who’s thinking about travelling alone

We hope this episode inspires you to take the leap and book your next solo trip! You won’t regret 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


Related Episodes:

Read More