Alan Nelson ran nightclubs in New York before he ever made a living with a camera — and he definitely didn't plan on teaching in Nagoya.In this episode of Career Thoughts Over Coffee, Alan and I talk about the twenty-some years since his first trip to Japan: the subway ad that pointed him toward a classroom, the year he had to sell his camera just to make rent, and the long way back to the abstract, motion-blur photography that made him fall for a lens in the first place. We also get into something a lot of us are quietly sitting with right now — what AI is doing to creative work, and why loving an AI-made song can feel like a small betrayal of everyone who makes art for a living.This one's for anyone whose career didn't go the way they planned — and turned out fine anyway.In this episode:Growing up in 1980s–90s New York, and how it shaped himNightlife, DJing, and running clubs in NYC — including TwiloThe first trip to Japan that changed who he wasBuilding a life, a marriage, and an unplanned teaching career in NagoyaSelling his camera to get by, and finding his way back to photographyWhy he calls himself a "serious" photographer, not a "professional" oneAI, art, and the guilt of loving something a machine madeWhat he'd tell his 20-year-old selfAbout Alan: Alan Nelson grew up in New York City, working his way through the city's nightlife scene — DJing, bartending, and eventually serving as music director at Twilo — before a first stint in Japan changed the direction of his life. He's now based in Nagoya, where he teaches and shoots serious, abstract photography built around motion blur and long exposure, working across film and digital, with his focus increasingly turning toward exhibitions and fine art.https://www.instagram.com/goodbar___/Subscribe for more honest career conversations — because no career path is a straight line.

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/