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Today, we are joined by Kathleen Porter Kristiansen, who has a unique story that has taken her all across the world. She is an 8th generation “Mainer,” who grew up in Portland. While loving her hometown, Kathleen was always itching to travel aboard. When looking into law school, she found an education hack with the opportunity to go to law school for free in London. This allowed her to avoid over $200k of debt while gaining experience in the international law field.

Kathleen spent three years working for a law firm in London before switching to a new role that was stationed in Switzerland. While living full-time in a Marriott in Zurich, she got her first taste of travel points hacking. Even though she enjoyed her position, she was working over 100 hour weeks and knew that this life style was not sustainable.

Kathleen found a new role back in the UK in the field of legal technology, which she was extremely excited about. Over the next few years, she had two children and was able to take two years off for maternity leave. During this time, Kathleen kept thinking about what was next and started dabbling in different ventures. She purchased an apartment in Portland Maine to manage as an Airbnb and have a place to stay when visiting her hometown. With the first one being a success, she continued to purchase new properties to grow her Airbnb business.

Around the time, The Points Guy was looking to start a UK branch for his business. Kathleen sent multiple cold messages to the founder and was able to lock in a meeting as he was visiting the UK. This led to Kathleen being offered the opportunity to write content and she took the leap to quit her full-time job.

Fast forward, Kathleen manage three Airbnbs and has created an online brand called “Triple Passport” that focuses on travel, investing, and family content. She has been featured in several media outlets, such as CNN, CondeNaste, Vogue, etc. Also, Kathleen is a regular contributor to The Points Guy and The Points Guy UK.

If you are interested in learning more from Kathleen, feel free to follow her here.

Check out the conversation as we dive into the following:

  • How she used education hacking to go to law school for free

  • How she built an Airbnb business while still working a full-time job

  • How social media opened the opportunity to cold connect with others and how this changed her life

  • How content creation can be a roller coaster, but it is important to just keep creating

  • How she utilizes time blocking to manage time between her businesses and her family

Listen to Kathleen share her story and get inspired with her amazing advice to people thinking about following a similar path. Check out the full conversation on YouTube or Spotify by clicking the links below.

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Know someone who should be on Why I Quit? We’re looking for all types of stories and people to feature at the top of the show. To nominate yourself or someone else, email and tell us your name, where you’re from and what you want to talk about.