Intro
Ruby Tan is a Singaporean outdoor instructor and adventure guide based in New Zealand. After years of searching for meaning in a fast-paced city life, she left her career in media to study outdoor education — a decision that took her from cubicles to classrooms under the open sky.
In this conversation, we talk about how Ruby discovered her love for the outdoors, what it means to find belonging far from home, and how she rebuilt her life and identity through nature. From quitting her job and planting cucumbers in Nepal to kayaking and hiking across New Zealand, Ruby’s story is a lesson in courage, reinvention, and faith in the unknown.
Story Highlights
- Leaving a corporate job to pursue outdoor education in New Zealand
- Discovering purpose through nature and guiding
- Overcoming loneliness and depression after returning to Singapore
- Moving between countries and learning to start again
- Finding meaning in discomfort, resilience, and connection
Quote
“I just always had that faith that something will happen, the right thing will come along at the right time. All I knew at that point was I just needed to stop and go figure myself out. I had to come to this place of acceptance that I have to chase my dream without my mom’s approval.”
About Ruby Tan
Ruby Tan is a Singaporean outdoor educator and guide now based in New Zealand. She began her career in media before discovering her calling in nature, training in outdoor education, and later leading expeditions across Asia and Oceania. Through her work, she helps students and travelers connect with the natural world and themselves. Her journey from urban life to mountain trails is a story about courage, independence, and finding belonging in motion.
Why This Conversation Matters
Ruby’s journey shows that fulfillment sometimes requires walking away from comfort to find clarity. Her reflections on identity, mental health, and home reveal how joy can coexist with struggle, and how the wilderness can teach us what we forget in routine — presence, patience, and purpose.
Turning Points
Ruby’s first turning point came when she left a promising media career to work on a farm in Nepal, where she realized her need to live a life outdoors. Later, studying in New Zealand transformed that desire into a profession. Returning to Singapore during the pandemic challenged everything she’d built, forcing her to confront isolation, depression, and rediscovery. But through therapy, travel, and persistence, she found her way back to New Zealand — and to herself.
Key Lessons
- Trust your instincts. Faith often comes before clarity.
- Discomfort reveals truth. Growth happens where comfort ends.
- Home can change. Belonging is something we build, not inherit.
- Rest is part of resilience. Even adventurers need stillness.
- Meaning requires courage. Fulfillment is found by those willing to start again.
If You Enjoyed This Episode
You might also like:
- Rob Lilwall on Adventure, Resilience, and the Courage to Keep Going — exploring perseverance through uncertainty.
- Kenneth Tay on Fighting, Failure, and Finding Balance — about rebuilding strength through discipline.