Today we talk with with Heather, an executive and leadership development coach, facilitator, and community builder in Tokyo’s startup ecosystem.

Heather’s career started with psychology and English literature, then moved through teaching in Korea, educational leadership in Japan, program leadership at an IT bootcamp, and eventually coaching leaders, founders, and people navigating major transitions.

The conversation explores the difference between coaching and therapy, why advice is often overrated, how moving abroad changes your sense of competence, the myth of the “correct” career path, entrepreneurship, burnout, relationships, and the additional challenges women entrepreneurs face in Japan.

At its heart, this episode is about learning to recognize when an old version of your life no longer fits — and how to move toward the next one with more awareness.

In this episode of Career Thoughts Over Coffee, I speak with Brandon about building a career that does not fit into one simple box. Brandon is a New York-qualified lawyer based in Japan, a coach, and a university lecturer. His journey has taken him from the US to Singapore, Kyoto, law school, international legal practice, teaching, and coaching. But what makes his story especially interesting is not only what he does — it is how his career became a combination of different roles, interests, and unexpected opportunities. We talk about working across cultures, what coaching really means, why language matters when building a career in Japan, the discomfort of networking, and how careers can become richer when they do not go exactly as planned.

Brandon's Contacts:

https://whittakercoaching.com/

https://www.linkedin.com/in/brandonwhittaker/

In this episode of Career Thoughts Over Coffee, I sit down with Matthew to talk about a career path that was anything but straightforward. From philosophy and heavy metal to Japan, data, disaster response, real estate, and problem-solving, Matthew’s story shows how unexpected experiences can shape the way we work, think, and create value. This conversation is about turning chaos into direction, learning from difficult moments, and building a career that could never have been planned on paper.

https://www.mkultraman.com/

In this episode of Career Thoughts Over Coffee, I sit down with Monika to talk about identity, career change, burnout, and what it means to build a path that actually feels true to who you are. From moving to Japan at a young age and trying to fit in, to leaving a job without a clear Plan B and eventually discovering that being different can become a real professional strength, Monika’s story is honest, thoughtful, and full of lessons for anyone questioning where their career is heading.

In this solo episode of Career Thoughts Over Coffee, I reflect on burnout, overthinking, and the quiet pressure of trying to build a career and life that actually feels meaningful. This is an honest conversation about hitting a wall, questioning direction, and trying to reconnect with the things that once gave work and creativity a sense of purpose.

Gear that I use: Cameras I use for the Podcast: • Canon EOS R6 (Kit) https://amzn.to/30xxXOy • DJI OMSO Pocket 3 https://amzn.to/2OZQZrh Lenses I use to Capture the thumbnails: • Canon RF28mm F2.8 STM https://amzn.to/4dE9WsF • Samyang 85mm f1.4 RF mount https://amzn.to/3lhoGncMics that I use to record the Podcast: • RODE Microphones Wireless GO II https://amzn.to/3E5nwE7 • RODE Interview Go https://amzn.to/4efdqlTTable Top Gear: • Microphone Stand https://amzn.to/4dQtZUR • Microphone Holder https://amzn.to/4gpViXV

Sherif is back and today we discuss Stoicism and how it can help us career wise and also in our personal life. Gear that I use: Cameras I use for the Podcast: • Canon EOS R6 (Kit) https://amzn.to/30xxXOy • DJI OMSO Pocket 3 https://amzn.to/2OZQZrh Lenses I use to Capture the thumbnails: • Canon RF28mm F2.8 STM https://amzn.to/4dE9WsF • Samyang 85mm f1.4 RF mount https://amzn.to/3lhoGncMics that I use to record the Podcast: • RODE Microphones Wireless GO II https://amzn.to/3E5nwE7 • RODE Interview Go https://amzn.to/4efdqlTTable Top Gear: • Microphone Stand https://amzn.to/4dQtZUR • Microphone Holder https://amzn.to/4gpViXV

Alejandro's socials:https://www.linkedin.com/in/alex-pascual/Website:https://mynago.com/login

Elder's socials:

https://www.instagram.com/elderinjapan/

https://www.linkedin.com/in/elder-ripper/

Website:

https://studenthousingjapan.com/

Sasha's Insta:https://www.instagram.com/sasha_hanim/My social media Accounts: https://www.instagram.com/untitled.thoughtsovercoffee/ https://www.instagram.com/frame.watcher/Gear that I use: Cameras I use for the Podcast: • Canon EOS R6 (Kit) https://amzn.to/30xxXOy • DJI OMSO Pocket 3 https://amzn.to/2OZQZrh Lenses I use to Capture the thumbnails: • Canon RF28mm F2.8 STM https://amzn.to/4dE9WsF • Samyang 85mm f1.4 RF mount https://amzn.to/3lhoGncMics that I use to record the Podcast: • RODE Microphones Wireless GO II https://amzn.to/3E5nwE7 • RODE Interview Go https://amzn.to/4efdqlTTable Top Gear: • Microphone Stand https://amzn.to/4dQtZUR • Microphone Holder https://amzn.to/4gpViXV