I just returned from Japan—a trip my family and I had dreamed about for years. We went to explore. I went to reflect.
There’s something about being immersed in a culture so grounded in meaning and intentionality that makes you pause and ask big questions.
While standing at Shibuya Crossing—surrounded by thousands moving in every direction—it hit me:
This is what most careers look like.
Everyone working hard. Everyone trying to move forward.
But also—everyone blending in.
It made me think back on four moments in my career when I made a very different choice. I chose to stand out. Even when it didn’t make sense to others.
2002 – Breaking the Mold
I was working in finance at IBM after a rocky start post-9/11. The world was uncertain—and so was I. So I made a bold move: I left to become a teacher. Everyone thought I was crazy. It was one of the best decisions I’ve ever made.2007 - First Big Leap – Leaving Consulting for the Unknown
After grad school, I landed a great consulting gig. But then came an unexpected offer—from a company I had never heard of: FirstService. I took a leap. That leap became a career-defining chapter.2016 - The Sabbatical Ask – 100+ Days Off
After a decade at FirstService, I was given a chance to rejoin the corporate team—this time as a named executive. I asked for something executives don’t typically ask for: 100+ days off to travel the world with my young family. I had no idea how we’d pay for it. But we figured it out. And we made memories that will last a lifetime.2023 - The Most Recent Risk – Quitting at the Peak
After 17 years, I stepped down to pursue a dream: finish my doctoral research and chase some entrepreneurial ideas. That story is still being written.
I’ve always been comfortable taking steps that feel different, even risky.
And more often than not, it’s made all the difference.
Because in my opinion, there’s nothing appealing about being like everyone else.
What Japan Can Teach Us About Career Growth
During this trip, I revisited a few powerful Japanese concepts that have shaped not just their culture—but can profoundly shape your career:
Kaizen (改善) – Continuous Improvement
Small, consistent upgrades over time lead to exponential results.
In your career: show up daily, improve by 1%, and never settle.Ikigai (生き甲斐) – Your Reason for Being
Where what you love, what you're good at, what the world needs, and what you can be paid for intersect.
In your career: align passion with purpose and contribution.Shokunin (職人) – The Mastery Mindset
A deep, almost spiritual commitment to craftsmanship.
In your career: don’t chase titles. Chase mastery.Wabi-Sabi (侘寂) – Beauty in Imperfection
The acceptance of impermanence and flaws.
In your career: perfection is a trap. Embrace learning in motion.Gaman (我慢) – Enduring with Patience and Dignity
Quiet strength and resilience during hard times.
In your career: the path won’t always be easy. Stick with it.
I even made this video for you to go a little deeper into how to apply Kaizen to your career:
Want to Go Deeper?
Here are two powerful reads I recently finished that I highly recommend (yes, affiliate links—so if you buy, I earn a small commission):
Ikigai by Hector Garcia
A beautifully simple book that explores how to live with purpose, meaning, and joy—based on the lives of the world’s longest-living people in Okinawa.A Brief History of Japan by Jonathan Clements
A fast, insightful read on the evolution of Japanese culture and society. Helps you appreciate why these timeless concepts still matter.
Final Thought
If you feel like you're moving with the crowd but not getting ahead, you’re not broken.
You’re just blending in.
The antidote?
Stand out on purpose.
Start small. Improve daily. Align your career with what matters.
Because in the end, that’s how you go from one of many…
to the one who gets chosen.
Best regards,
Roger