Career Cailyn and Gillian Career Cailyn and Gillian

Asking For A Friend: How Do I Pursue A Freelance Career?

Welcome to our first ever Asking For A Friend episode series, where we tackle your biggest questions and deep dive into our own personal experiences and expertise.

We’re kicking it off with a Q&A with Gill, all about how she pursued a career as a freelancer. With The Great Resignation and more demand for flexibility and remote work, working on contract has never been more popular (#youwontbreakmysoul).



Welcome to our first ever Asking For A Friend episode series, where we tackle your biggest questions and deep dive into our own personal experiences and expertise.

We’re kicking it off with a Q&A with Gill, all about how she pursued a career as a freelancer. With The Great Resignation and more demand for flexibility and remote work, working on contract has never been more popular (#youwontbreakmysoul).

A third of Americans are gig workers, and 13% of Canadians are freelancers, but it can be tough knowing how to start, how to pitch your services, and how to price your work. 

Whether you want to quit corporate and be your own boss, or start a side hustle to earn some extra cash, this is your guide to networking, building a portfolio, and finding balance amidst the crazy workload. 

Tune in as we chat about:

  • How Gill started her freelance career

  • The importance of building a strong network

  • How to price your services and set income goals

  • Figuring out what marketable skills you can offer

  • Balancing multiple clients, scarcity mindset and avoiding burnout

  • The pros and cons for going freelance

  • Why building routine and consistency are key

DM us if you have any burning questions that you’re Asking For A Friend, and we’ll dive into them in our next Q&A!


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 57: Our Top 8 Tips on Launching a Business

Take it from us: building a successful side hustle or business is time consuming, especially if you’re juggling it between your 9-5 and all of life’s other commitments. But being your own boss definitely has its perks and it seems the entrepreneurial feeling is catching on. Gig workers now represent more than one in 10 Canadian adults, and 20% of millennials – the next could be you!

If you’ve been thinking about giving your own biz a go, this ones for you! We’re all about sharing the wisdom, so in this Quickie we’re passing along the most important lessons we’ve learned starting our own business and how to set yourself up for success.



Take it from us: Building a successful side hustle or business is time-consuming and scary, but being your own boss has some serious perks, and it seems the entrepreneurial feeling is catching on. Gig workers now represent more than 20% of millennials in Canada…you could be next! (And we love that journey for you.) 

If you’ve been thinking about giving your own biz idea a go, this quickie is for you! We’re passing along the most important lessons we’ve learned starting our own business—the good, the bad, the hilarious—and how to set yourself up for success.

Tune in as we launch into:

  • Why you need to stop waiting for the perfect time to start

  • Defining your mission and value proposition

  • Understanding your consumer and audience

  • The importance of setting up your finances and legal structure

  • Creating killer branding

  • How to launch with a bang

  • The metrics that matter for your launch

  • How to avoid burnout and stay committed 

We hope this episode inspires you to take the leap and launch your dream idea! And remember, the key is to just start and keep learning as you go. 


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