Chief Change Officer
#329 Gary Bremermann: Hitchhikes, Burnouts, and Building a Career Worth Living
Tue, 29 Apr 2025
Tokyo-based American Gary Bremermann didn’t stumble into career clarity—he fought for it across countries, careers, and crises. From hitchhiking North America to building and burning out of his first company, Gary’s story is a blueprint for real Gen X reinvention: practical, nonlinear, and painfully honest. In this first of a two-part series, he shares how early travel, entrepreneurial scars, and the brutal experience of misaligned success shaped the recruiter and career coach he is today. For Gen Xers still figuring out their next chapter—or building a life while surviving their own rough drafts—this episode offers both grit and grounded hope.The National Geographic Kid“I grew up with every issue ever printed—and a mind wired to explore.”Gary shares how childhood dreams of travel sparked a lifelong hunger for exploration, curiosity, and career experimentation.Hitchhiking Lessons You Don’t Learn in Business School“I learned how to talk to anyone, anywhere, about anything.”Gary reflects on how crossing the U.S. and Canada on foot and rail taught him real-world communication skills he still uses as a recruiter and coach.Dropping Out—Twice“School couldn’t hold me—but neither could drifting forever.”He talks about his struggles with traditional education, dropping out, traveling the world, and ultimately rebuilding himself on his own terms.Entrepreneurial Burnout: The Hidden Cost of Chasing Money“I was expanding globally—and being crushed by my own business.”Gary shares how chasing financial success without personal alignment almost destroyed him—and why selling his first company saved his life.Finding Freedom on Different Terms“Money isn’t the goal. Alignment is.”After exiting his business and hiring a life-changing coach, Gary explains how he reframed financial success as a byproduct of purpose, not the point._____________________Connect with us:Host: Vince Chan | Guest: Gary Bremermann --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Gary Bremermann and what is his career background?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chan, your ambitious human host. Our show is a modernist humility for change progressives in organizational and human transformation from around the world. Today, we are diving into career transformation with Gary Berman.
Gary is a recruiter, career coach, and Japan talent market expert who has spent 25 years helping professionals navigate change. But his own journey wasn't a straight line. Gary hitchhiked across North America, dropped out of college two times, built a global business, and burned out before finally finding his true calling.
In this two-part series, we'll explore how he discovered his passion for coaching, the seven rules of career clarity, and the harsh realities of Japan's talent market, including ageism and the fear of change. Whether you're rethinking your career, hiring talent, or just wondering what's next, this series will change the way you see work. Let's get started. Gary, good afternoon to you.
Welcome to the show. Welcome to Chief Change Officer.
Thanks for having me, Vance. It's a pleasure to be here.
Gary and I have a mutual friend, also happens to be a podcast guest. And now, it's like a snowball effect. More and more people reaching out to be on the show. But I'm still very mindful about finding the right fit. And anyone listening to this episode will see that Gary is exactly that. I'll let him share his story, his ideas, his high sights, insights, and foresights.
But first, Gary, tell us a bit about yourself. What's your journey been like? Give us all the juice and then we'll dive into different elements and unpack some of your wisdom and intelligence.
All right. Thank you. I guess we'll start with where I'm at now. So I'm currently residing in Tokyo. I've been here for 25 years and I'm a recruiter and a career coach. And I've been recruiting for 23 years and I've been career coaching for a decade. And I didn't find my calling in life until my mid-30s. So I've been, this is my calling.
I'm very fortunate to have found my dream job and my dream life. But it took me a long time to get there. So I wanted to share with you part of my story today. And so I recruit advertising and marketing professionals. I career coach for bilingual professionals in Japan. from all different industries, all ages, different people with different stories.
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Chapter 2: How did Gary's love for travel begin in childhood?
And I help companies build teams of talented individuals. And in my coaching practice, it's helping people accelerate their career growth and find more joy in the work they do.
You are in Tokyo now, one of the dream destinations for so many people, whether for travel, work, or even living. What brought you there? It might seem like a simple question, but I feel like there's a bigger story behind it. Let's trace back. Where are you originally from? And how did your journey lead you from one place to another, eventually landing you in Tokyo?
So it goes way back. And I was born and raised in San Diego. And I was very fortunate to grow up in a house that had a copy of every single National Geographic magazine ever published. And it started in 1888. So in my house, we had a wall that had every National Geographic from... And I would, on a rainy day, as a young boy, I would pull issues off the shelf and...
read through them and get super excited about what's out there, what's out there in the world. And that's really what started to lead me to Tokyo, was wanting to explore the world. So that was the start of my wanting to go places and see things and do things. I first came to Tokyo in 1985, but I've lived here now a total of about 30 years. So I've been back and forth between California and Tokyo.
Before social media, before Instagram made picture-perfect moments so accessible, you were already living with the whole world in front of you. Even as a kid, you were constantly on the move. So can I say you were a world traveler from the start?
In my mind, for sure, yeah. And it was definitely very analog. I grew up with black and white TV, no internet, and now all those national geographics are on the internet, or for a time there it was on a CD-ROM. But back then it was analog, and it was fantastic.
Before moving to Asia, you had quite a journey, especially in North America. Tell us about that. What was your experience like?
So, yeah, I was talking about how it took me a long time to find my calling in life in my mid-30s. And as I started working on my career coaching practice and working with other people to help them find their own callings, I realized that you can find clues from your early life that inform or give you ideas about what you can do to find your calling.
And so when I started doing the work on myself, I looked back and I realized there were some life experiences in my early days that really informed what I'm doing now and why I enjoy what I'm doing now so much. So the first one was that National Geographic story. But another one was when I was 18 years old, I was in university for my first year in university.
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Chapter 3: What lessons did Gary learn from hitchhiking across North America?
So I dropped out of university at I was 18 years old at the time, and I hitchhiked from Santa Barbara, California, to Newfoundland. And it wasn't in a straight line. So I hitchhiked all over the United States and Newfoundland's an island. And I was I caught a ride with someone who put their car on a ferry. So I technically hitchhiked to an island.
And then I took the train across Canada, the Canadian rail train, and then hitchhiked back from Vancouver back to Santa Barbara. And one thing I learned along the way, everyone along the way said, Gary, don't be stupid. Go back to school. Get an education and then you can do whatever you want, because I had really determined to quit school.
But the other thing, looking back in terms of how it informed my career choices is or the thing that I got from it was I learned how to talk to people from all walks of life. young, old, men, women, all over the country, people would pick me up, very kind people, had some few rough experiences. But at a very early age, I learned how to communicate with people who were very different from me.
So that was one of my life forming experiences.
Even within North America, you've experienced life across different states, different time zones, and completely different cultures. East goes West goes Midwest. You've seen it all. And then there's Canada. A mutual friend once mentioned that some of his friends wanted to move from the US to Canada, thinking it would be the same. And he said, no, Canada is not just another version of the US.
There are a lot of differences, a lot of nuances. You've learned that firsthand, didn't you? And not just from books, but from real life experience. You mentioned struggling in school at one point, but you did go back, right?
Yes, I eventually did. And that was a good decision. And you know what's funny, Vince, is that a lot of people in my world don't know about my hitchhiking experience. It's not something that I share with everyone. So if anyone's listening to this that's known me for quite a while, they might not know that I had that grand hitchhiking adventure. But it was a really life-forming experience.
How did you support yourself financially along the way? What kind of work did you do to keep things moving while navigating your journey?
Yeah, in terms of making the trip happen, I had very little money. I did have some cash on me, but I carried a tent and a backpack and I would sleep wherever I could. But also a lot of kind people took me in. And they invited me to stay at their house.
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Chapter 4: Why did Gary drop out of college twice and what did he do afterward?
And I was a young man living in Japan and at the time the Japanese economy was really booming and growing fast and it was the bubble years and it was a very dynamic time to be here. And then I went back to the United States and got a graduate degree. So after dropping out twice from university, I ended up going to grad school and getting a graduate degree.
And then the biggest thing that happened to me in that decade before I found my calling was I graduated from university from the grad school and started my own business. And that was 10 years of heaven and hell. Great things happened. It was a great challenge, but it was also the business was crushing me. I had gotten into business because of a very strong desire to be financially successful.
and make a lot of money. Richard Branson was one of my childhood heroes. I read books about him and I thought he was so cool. And I thought, I want to be Richard Branson. I want to be, at the time it was multimillionaire. Now he's a billionaire and do diverse fun businesses. So I started a company in the United States and I operated that company for nine and a half, 10 years. Mm-hmm.
And in my last year, I realized that the business was crushing me. I had expanded the business. We had an office in London. I was based in California, moved the office from San Diego to Los Angeles and an office in Tokyo. And I worked around the clock. I never took vacations and I experienced burnout. And that was a huge turning point in my life.
You had a business back then, didn't you?
I had a business where I was exporting consumer goods, American style, American culture goods. It started out in exporting it to Japan because we had connections and an interest in Japan, expanded into Korea and then expanded into Europe. And it was things like apparel, sporting goods, health and beauty products. And so I was an intermediary between manufacturers and customers.
in Asia and Europe. And it was exciting, but it was it was so hard in some ways. And the reality was, I wasn't that interested in consumer goods. I wasn't that interested in fashion. I love sports, but it was just I was doing it for the money. Also for the freedom. I've been an entrepreneur all my life. Also the freedom aspect of it. But when you're a slave to your business, you're not free.
And so I was very fortunate. My company was acquired. Yeah. right before it crushed me was it burnout stage and at that time i engaged a coach so i had a coach and i tell my coach at that time that he saved my life and i mean it he was he really helped me to get clarity
on what I was doing, why I was doing it, showed me that there were alternatives, and then helped guide me through the sale of my business. So it was a real, talk about change, it was a real turning point for me. So I sold my business and decided to move back to Japan.
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Chapter 5: How did Gary support himself financially during his travels?
And so when I had that experience with my business almost crushing me, it's my next phase in life, I'm going to be doing something where I get paid decently, make good money, have the opportunity as an entrepreneur, but also do something that's really helping others and aligned with my strengths. And so that kind of ties back to with the ability to talk to different people.
And so money was more of a side effect. Of course, I'm very, as a business person, I'm very financially minded and keep an eye on cashflow and revenues and profits. But it's really being able to do something where I feel like it's aligned with my true self. And I feel blessed to be able to be doing that.
Not sure if you saw this, But there was a survey. Some organizations published results about financial success across different generations. They asked baby boomers, Gen X, millennials, and Gen Z what they think it takes to be financially successful. And this went viral because of Gen Z's response. Their expectation on annual salary is at least $600,000 a year.
All that, yes. Oh my gosh, yeah.
I am a Gen X, so when I saw that, I had to take a step back. And that's why so many people started debating it. Now, my question isn't about disputing the number itself. It's just a data point and honestly, I'm not sure how they even conducted the survey. I tend to question the analytics and assumptions behind these things.
But just assuming the number is reasonably representative does reflect something interesting. It seems like younger workers, especially those just starting out, have a huge appetite for financial success. Meanwhile, those who are more established, who've been through it, so to speak, tend to have a different perspective. Of course, when we are young, we all want to prove ourselves.
We want to make money, be successful. And you were no different. You once chased financial success. But now, you not only have that experience, you also help people figure out their own career paths. Whether they stay in a corporation or transition into entrepreneurship, both of which come with financial shifts.
So after everything you've learned, what does financial success actually mean to you now? And if you were advising younger people, knowing what you know now, what would you tell them about what really matters when it comes to money and success?
Yeah, that's a tough question because these drivers for when you're a young person setting out on your early stages of your career, and if you're young and hungry and motivated and You want to go out and make an impact and do something big. And I had that bug and it may have been because I read about Richard Branson that I was just bound and determined. Now maybe it's Elon Musk.
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Chapter 6: What diverse people and cultures did Gary encounter on his hitchhiking journey?
And then having some extra money to enjoy your life. And then having money to put away for your retirement or whatever. But I find with people when I'm working as a career coach...
That maybe their parents or their generation has put expectations on them and they go to the best schools and they work for the best companies or they go get their MBA at a top 20 B school and they spend their time and energy chasing success. fortune or fame or status because they think that's the right thing to do. And that's the measure of your value.
And I recall when I had my business in the 90s and the business was my identity. That was it. And if the business did well, I was doing well. And if the business wasn't doing well, then I wasn't doing well as a person. And I think being able to step away with that comes with maturity.
But also, I really give a lot of value to my coach who because I had someone to it's lonely being an entrepreneur, but I had someone to talk to about it. And so I had this coach and he, as I mentioned, he saved my life. And I was like, I don't think I could ever do what he does as a coach. I had so much respect and admiration from him.
And then it took me another 15 years to get to the point where I put my coaching shingle out, where I felt confident enough to be a coach, to help people see things from a different angle. To help people understand that it's okay to not be super successful. Or it's okay to not be a millionaire.
Or help people find work and a lifestyle that's in alignment with their interests and their needs and their passions. So it's been a long journey. It's been rough at times. And it's still not always smooth sailing, even at this stage in my life. But I really feel like I found a place.
That's the end for today. We've explored Gary's unconventional journey from hitchhiking across North America to building a global business, burning out, and finally discovering his real and true calling as a career coach. But the real question is, how do you find your own career clarity today?
In Part 2, Gary breaks down his seven rules of career clarity and tackles the biggest hiring challenges in Japan, from ageism to the fear of change. Don't miss it! Thank you so much for joining us today. If you like what you heard, Don't forget, subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media. I'm Vince Chen, your ambitious human host.
Until next time, take care.
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