Jess Dales 043


Coming Back Home

Jess Dales



On this episode, I talk with Jess Dales, a woman often without a permanent physical address who has decided to spend her life traveling the world and getting as close to nature as she can, as often as she can. She has decided to answer the call of her heart and take the path less traveled. Literally and figuratively.

We sit down together and talk about making decisions based on outside expectations, the universe making decisions made for us, recognizing what we really want, coming home, the power and importance of nature, life as an introvert with a massive following, the need to live more slowly more often, the similarities we all share, and much more.

Key Points

  • Where Jess grew up and what her childhood was like

  • The role her parents played in her draw to nature

  • Why she studied to become a lawyer and her deep curiosity for the sciences

  • How she slowly started to move away from her dreams and aspirations

  • How keeping busy kept her from realizing she wasn’t really feeling fulfilled in a lot of ways

  • The sombre day at the law firm that left Jess and her colleagues without jobs

  • When the universe makes decisions for us

  • Being ok with quitting something that no longer resonates with who you are now

  • The tough time between being let go and rediscovering her love for the outdoors

  • The “lottery ticket” The Enchantments her brother won that started the shift

  • Starting an Instagram account as a picture blog

  • Getting her real estate licence to support herself

  • Having to prioritize and give up old ways of being to allow for what felt good to come into her life

  • Getting back to the clarity and innocence of childhood

  • Figuring out who she was without the influence of other people

  • Constantly asking herself the question “what do I ACTUALLY want?”

  • Letting go of the story she thought she wanted to live, and the freedom that came with stepping further away from outside expectations

  • Wanting to respect and honour the places she travels by being mindful of how she shares about them with her audience

  • Separating her online presence from her at home presence and why it’s important to make that distinction

  • On being an introvert and needing to recharge

  • Where she feels most at home considering she often doesn’t have a consistent physical address

  • The power of spending time in nature and it’s ability to reconnect us to ourselves and to each other

  • Practicing keeping focus and reducing distractions

  • On craving routine and the benefits of having one

  • Insight on balance and goals

  • Where Jess as been recently and where she’s going next

  • On jetlag

  • Why it’s important to take the time to live slowly more often

  • On starting something new and comparison on social media

  • The isolation and loneliness that can come with social media and travel

  • Being ok with having down days

  • What meeting people all around the world has taught Jess about how we are similar and the barriers that get in the way of us seeing that

  • The importance of face-to-face connection

  • Jess’s advice to those who are just starting and why taking a big leap isn’t required for you to do so

Rapid Fire

  1. What is your favorite morning beverage?

  2. What is your favorite sound? Smell? Place?

  3. If you could spend 24-hours in someone else’s shoes, who would it be?

  4. What is a book or books you’ve read that you think are worth sharing?

  5. What advice would you give your 20-year-old self?

  6. What is your Rebel Cause?


Instagram: @jess.wandering


The Enchantments

Dianne Whelan’s Episode



Moab, Utah

Less - Book by Andrew Sean Greer


Intro/Transition: Custom Track by Extra Deluxe

Outro: Daydreamer by Nomyn