Adios Chicago | February 2021 Update

My word of the month for January was “clarity.” Five days into the month I paused and promptly booked a one-way flight. Let me explain…

I ~planned~ to backpack Asia in 2020 after teaching abroad in Korea. The Universe laughed. THEN, I decided I would move to Spain November 2020 thinking the whole pandemic situation would be over and done by then. (It’s okay to laugh.) Finally, I announced to the world, well YouTube and Instagram, that my new OFFICIAL plan was to leave for Spain mid-March. The moral of the story: don’t plan anything (or maybe don’t listen to me….)

“If you want to make God laugh, tell her your plans.” -Anne Lamott

I took the beginning of January off social media to refocus and get some much-needed clarity.

I thought to myself, “Europe might not open in March… then what? What’s your plan B? Should I stay in Chicago and get an apartment? Should I go somewhere else in the meantime? Should I wait it out? Is it time to go? Will I survive this winter……………?”

Shortly after, an Instagram friend (yes, they are real friends) announced she was heading to Puerto Vallarta, Mexico. I paused. I googled.

Puerto Vallarta (PV) is a beach resort town on the Pacific coast of Mexico known for its beautiful beaches, water sports, and LGBTQ+ friendly nightlife. It’s also an up and coming spot for digital nomads because of the abundance of co-working spaces and meet-ups. It’s pretty much a travel blogger’s dream: high search traffic for the blog, work-life balance culture, and super affordable (for expats/travelers).

I did what any sane person would do. I booked a f*cking flight to Puerto Vallarta, Mexico. I leave in four days.

DISCLAIMER: I am in no way promoting or encouraging international travel. The best thing to do is to stay home or explore locally while maintaining social distance. My situation (and possibly others who are traveling right now) extends further than meets the eye. I plan to travel responsibly and take necessary precautions.

When I quit my job to travel 7 years ago, I wasn’t sure where my path would lead. Travel has since become a way of life and my job.

Yesterday was my last shift working at the Cheesecake Factory. [Fun fact: Cheesecake Factory tips have funded about 75% of my travels. *Tip your servers.*] As I said my good-byes, I chatted with a co-worker who expressed how much she’d love to travel and I blindly encouraged her to do so. She revealed she is part of the DACA program and cannot leave the USA. DACA was created to protect undocumented young children from deportation. The program does not give Dreamers a pathway to citizenship or even legal permanent residency. Dreamers have to reapply for the DACA program every 2 years ($$$) and while applicants can leave the country there is a chance they could be denied re-entry, even if the government granted permission to travel.

I paused and was reminded how much of a privilege it is to travel. Someone out there dreams about having the life you have. Whether it’s affording a meal, having a family, a job, or traveling – we are #blessedAF.


Leaving Chicago feels like leaving a relationship. Why it is that right when you decide to leave, you are love-bombed (in jobs, relationships, etc)? All of the sudden, snow looks majestic. It’s not THAT cold out. I am flooded with opportunities urging me to stay in the warmth of the knowing.

Change is general is hard, no matter how exciting or good for you it might be.

As I always say, life gives you bits of sweet crumbs to stay, but there is often a buffet waiting for you at the other side.




  • Ariel
    February 4, 2021 at 10:13 am

    Me thinking if my job would let me work in Mexico …👀

  • Melissa Chavez Chavez
    February 4, 2021 at 2:31 pm

    How exciting! My fiancé’s grandmother lived there for 20+ years and loved it we went there January 2019 got lucky before the pandemic. You must visit Sayulita nearby such a cute town:.

    • Courtney
      February 15, 2021 at 11:18 am

      AHHH love!!! I think I’ll explore Sayulita next weekend, gracias!!

  • monica
    February 12, 2021 at 7:12 pm

    Glad to see you’re on the move Courtney! 🙂 Have a great time!

    • Courtney
      February 15, 2021 at 11:17 am

      Gracias Monica!!! <3


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