I read about Khe Hy in The Wall Street Journal and his story fascinated me. Here’s this young guy (mid 30s) at the top of his game on Wall Street—the youngest Managing Director in BlackRock’s history—and he was walking away, moving to California. Surfing every day. Being around for his kids. Living his best life.
It was like he had cracked the code:
Get in. Make your millions. Hit your number. Get out.
It all sounded so logical and aspirational on paper. I couldn’t help but immediately buy in. I wanted to talk to him, learn from him, really hear how he felt about the decision after a few years.
Like, “Hey man, how do you see it now? You’re older. You’re married. You’ve got kids. They’re getting older. Is this all you thought it would be? Has life cracked up, or stacked up, the way you imagined?”
So I reached out, and he was gracious enough to join me for a ‘How I See It’ conversation.
He’s given some phenomenal talks online and I wanted to make sure we got pst the boilerplate stuff. Like what he’s really learned. How he’s built his newsletter to over 50,000 subscribers. And how he feels as a dad and man.
Photo: Kevin Gilligan @photosbykag
When we finally connected, what I found was a man deep in reflection. At a crossroads. Right at that intersection we talk about so often: where personal passion meets professional experience.
And he was thinking the same things we all think in midlife:
Did I leave too much money on the table?
Did I walk away too early?
Why am I still renting instead of owning?
These kids are expensive.
What do I really want to do with my time, my energy, my life?
Now there’s AI. And he’s telling me how interested he is in that space. How he wants to learn, teach, engage. It was an honest conversation and we found a lot of common ground.
We both like expensive things. We have expensive taste. We appreciate quality. We want the freedom to do what we want, when we want, with who we want—for as long as we want.
But here’s the deal with authenticity:
Chasing authenticity where authenticity doesn’t exist, is exhausting.
At different stages of life, it’s not that we’re being inauthentic, it’s that we’re evolving. What was once us, authentically, shifts. The message, the persona, the brand, it changes. Sometimes subtly. Sometimes radically. And even when we pivot, we still reserve the right to change our minds again.
Because midlife isn’t just about learning new things. It’s about unlearning too. It’s about being open to both. This was one of my favorite conversations. Because I like both versions of Khe Hy. I like Part One, what he built, what he walked away from.
And I really like where he’s headed now. Like me, and like so many of you, he’s just getting started. There is no timeline. No finish line.
Just forward motion. Please check out Khe’s newsletter on future-proofing your career with AI, and enjoy this week’s ‘How I See It’ with Khe Hy right here:
How Khy Hy Sees It:
On Valuing Liquidity:
“I just love being a renter. Like 95% of the time, I’m like, I’m so happy. I rent because I value liquidity, I value cognitive ease.”
On Loving the Pace of Wall Street:
“I love the pace of it. It was really fast-paced. I love markets. I love intellectually challenging problems. I love being around smart, driven, really ambitious people when they’re not trying to stab you in the back.”
On Seeking Control Over Time:
“The biggest one was I just wanted to control my time. The goal was never to not work. The goal was to own your time.”
On Financial Transparency:
“I had three years where I made over a million dollars… 85% of my paycheck, I’m like, at some point, you gotta monetize your savings, or else you’re just saving for the sake of saving.”
On Workplace Culture:
“I didn’t like the industry of Wall Street… I wanted to opt out of a world where the default setting is to stab the person in the back to get ahead.”
On Curiosity and Growth:
“I’m just a curious person… there’s so much more to life than quantitative trading hedge funds, and I didn’t want to be compensated by being an expert in a thin sliver.”
On Experimenting Before Quitting:
“I was just trying stuff for probably two to three years… What that told me is, you can move the needle this much with eight hours of your lowest energy hours. Imagine what would happen if you could give 60 of your best hours to that?”
On Facing Criticism:
“Someone who was a big advocate of my career, said, “I see this all the time with these finance guys, they think they’re entrepreneurs, but they’re not. They spend way more than they think and earn way less.’”
Photo: Kevin Gilligan @photosbykag
On Being a Mirror:
“When you do something like what I’m doing, you are a mirror to other people, because you are doing something that either someone wants to do and might do, but usually you’re mirrored to someone who wants to do it, who knows that they will never do it.”
On Prioritizing Family:
“I made family a big part of why I did this. Being the parent that I want to be… I could show up, make a one-year commitment to be in my kid’s class, without hesitation.”
On Following Aliveness:
“I have a personal motto, which is follow aliveness… things that bring me aliveness, I just do more of them, and things that make me feel dead inside, I do less of them.”
On Post-Achievement Struggles:
“Post-achievement is like you’ve had so much achievement that no achievement feels good anymore. You’re like, ‘What do I do next?'”
On Coaching Philosophy:
“A lot of times, people just want to be seen and loved… ambition and money and status, you just want someone to say, ‘I see you, you’re a good human.'”
In health,
BONUS: Want to join the conversation with ALL of our cover story guests? Now you can with MLM Live. It’s simple. We send you a link before our conversation and you can join us. Even better, you can submit questions for Greg to ask ahead of time or ask them yourself. The last 15 minutes are set aside for what’s on your mind. Become a member of MLM Live here.
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Greg Scheinman
Founder, Midlife Male
52. Husband. Father. Entrepreneur. Coach.
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