Career Cailyn and Gillian Career Cailyn and Gillian

Episode 218: How To Work While Traveling The World (And Hacks To Do It On A Budget)

If you’ve dreamt of travelling the world while you work and living that #DigitalNomad life, it’s time to stop dreaming and start planning, because it’s more possible than you might think.



If you’ve dreamt of travelling the world while you work and living that #DigitalNomad life, it’s time to stop dreaming and start planning, because it’s more possible than you might think. For remote WFH employees, freelancers and entrepreneurs, our ability to work from just about anywhere is wildly underused. There’s a whole world out there that we can enjoy between meetings, with better views than our kitchen table.

So shoot your workcation shot and tune into this updated throwback episode with Gill and Cailyn on all the tips and planning hacks to kill it in your career while travelling to epic places. 

Prepare for takeoff as we chat about:

  • Why workcations can work for corporate employees

  • How to choose your travel destinations

  • Navigating working in different timezones

  • Budgeting tips for your time working abroad

  • Setting expectations at work and communicating with managers/clients

  • The logistics of planning a trip around your work schedule

  • How to make the most of balancing work and travel

Travel on a budget with Kindred’s members-only house-swapping! Earn free credits with my invite code: GIL.BER1

PS: If you’ve been toying with the idea of launching a podcast but aren’t sure where to start or how to grow, check our consulting services at teachmehowtoadult.ca/howtopodcast!


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

@yunggillianaire


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Career Cailyn and Gillian Career Cailyn and Gillian

Episode 216: How To Navigate The Changing Corporate World, Communicating Better At Work, Building Side Hustles And The Power Of Generalists

Corporate culture is changing faster than ever before. We have quiet quitting and AI, mass layoffs and Gen-Z disruptors, side hustles and WFH warriors. How do you stand out, and how do we even figure out what we want from our careers?



Corporate culture is changing faster than ever before. We have quiet quitting and AI, mass layoffs and Gen-Z disruptors, side hustles and WFH warriors. How do you stand out, and how do we even figure out what we want from our careers? 

I'm joined today by TMHTA team member Carolyn Schissler for a roundtable on our experiences, successes, and failures in the workplace, the state of work, and how we can make it work for us. 

Tune in as we chat about:

  • The keys to corporate success, from getting hired to standing out

  • Being authentic and true to yourself VS assimilating into corporate culture

  • Being a generalist VS a specialist

  • Dealing with shitty bosses and brutal coworkers

  • The power of honest communication at work

  • The case for side hustles

  • The realities of working from home

  • Are work besties real friendships? What about office romances?

  • Networking on LinkedIn

PS: If you’ve been toying with the idea of launching a podcast but aren’t sure where to start or how to grow, check our consulting services at teachmehowtoadult.ca/howtopodcast!


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

@yunggillianaire


Related Episodes:

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Relationships Cailyn and Gillian Relationships Cailyn and Gillian

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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