Ask Faleskini - The Midlife Crisis Clarity Compass
This is the Ask Faleskini - The Midlife Crisis Clarity Compass podcast. All the Life Lessons You Need to Thrive in Midlife. This is your Guided Path from Chaos to Clarity, Confidence, and Purpose.
Peter Faleskini and his guests discuss everything midlifers are worried about or interested in.
Peter Faleskini and chosen guests will help you distinguish what is sustainable in life, relationships, health, and the economy from what is not. Not everything that shines is gold, and not all mud is dirty.
Ask Faleskini - The Midlife Crisis Clarity Compass
Are You One Yes Away From Solving Your Midlife Crisis? Jeanne Chung
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
Most people treat a midlife crisis as an emergency to suppress, but true midlife discontent is rarely solved by superficial fixes. It is resolved when you close the gap between rigid societal expectations and true personal contentedness.
In this episode of Ask Faleskini, Peter Faleskini sits down with former investment banker, wellness entrepreneur, menopause startup founder, and author Jeanne Chung. Jeanne shares how writing her memoir allowed her to "metabolize" her past—from understanding her father's escape from North Korea and navigating her brother's stroke to repeatedly reinventing her career across Wall Street, international yoga studios, and tech startups. Together, they explore how auditing your past decision points and saying bold new "yeses" can turn midlife uncertainty into a launchpad for your next era.
Key Takeaways in This Episode:
- Metabolizing Your Past: Why processing your life story digests both grief and accomplishments, converting past experiences into a solid foundation for your next chapter.
- Breaking the "Plan" Trap: How clinging to early-life timelines creates artificial midlife failure, and why letting go of the original plan opens space for authentic direction.
- The Power of the Unconventional "Yes": How saying yes to radical pivots—from banking to opening yoga studios in Singapore—builds the internal proof required to trust yourself.
- Happiness vs. Contentedness: Why midlife crisis resolution isn't about chasing temporary thrills, but taking stock of what brings deep, sustained contentedness to your life and work.
- Pivoting into AI at 58: How Jeanne is stepping into business process optimization and AI tooling, proving that age is never a barrier to learning new industries.
About Jeanne Chung: Jeanne Chung is a former investment banker (MIT graduate), yoga teacher, wellness entrepreneur, and menopause startup founder. She is an author, speaker, and consultant helping leaders map their major life decisions to step deliberately into their next chapter.
- Website & Worksheet: https://jeannechung.com/ (Download the "Mapping Your Yeses" worksheet)
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Peter's books
The Clarity Compass
Stop Midlife Burnout, Escape the Matrix, and Resolve Faleskini’s Complex
Faleskini’s complex
Diagnosing the Systemic Costs of Midlife Crisis and Advancing Holistic Pathways of Resolution
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Welcome to the Ask for the Skinny Podcast with a guest. I'm proud to present Jean Cheng. Jean, welcome to the show. Please tell us more about yourself. What is your story?
SPEAKER_01Hi, Peter. So nice to be here. I am my story is unusual. It starts with being raised by a tiger mom. Both my parents were from North Korea, so they're very strict about what I was supposed to do with my life. And then I became a yoga teacher, built in the yoga uh yoga world. I like to say built in the yoga and wellness world when wellness was lowercase wellness before it became uppercase wellness, Julian dollar industry. And then I built into menopause. So my last company was a menopause startup. And what I found is in the topic of midlife is it's the point where we understand things are shifting so deeply. And looking back to what we've gone through to me is a great exercise to help understand what we can lean into next. And so right now I'm writing a memoir. And the memoir, it's kind of an interesting story why it started a memoir. So I mentioned both my parents are North Korean immigrants. My father was a very one of the very famous North Korean escape of his time. And his story, as I learned over years, is kind of like a movie. And I always thought that I was gonna, I really wanted to write the movie, the uh this the script for the movie. And I would send my dad books on how to write an autobiography and all these things, and he never responded. And at some point I realized, well, you know what? This is not my story to tell. It's his story to tell. And if he doesn't want to tell it, there's nothing I can do about it. And then I had the second thought was, oh, you know, my story to tell is how I learned about his story. Because I learned about his story over years and years and years, little breadcrumbs. And that was the motivation to think about that arc of how I learned that through life, and then I how I had all these other stories. And I are and I've crafted a whole bunch of stories about my life, but that was the motivation. And what I found was just so powerful about writing the memoir is not just the art of what's in my head, what my experience was, and be able to write it on a piece of paper for someone else or in the laptop for someone else to consume and understand and also learn from. Like that's a big piece. That's the most obvious piece, rather. For me, it's about the idea of at this point in my life, I'm now going through all of these things that happen in a very deliberate way. And it's it's the opportunity for me to metabolize all of that so that it's now part of me and I own it fully. The good, the bad, the fun, the beautiful, the difficult, the grief, all of it. And where I am now with it is to really appreciate for myself that it becomes the foundation for what comes next. And I wouldn't have been able to do that in my younger self in my 30s or even in my 40s, right? It's something that is very clear to me now, being 58, that there's a lot to digest, that there's a lot to metabolize. And it's out of curiosity now, I stand, think about like where I'm gonna go next. Very cool.
SPEAKER_00Yeah, amazing. I like how you have explained um somehow that it's not just uh you writing the book that also a book writes yourself or helps rewrite your story.
SPEAKER_01Yeah, absolutely. So it was it was so fascinating. So you think about stories as almost like little cards. You have every story as a card. And I always carried stories in a certain way, like this card is blue, this card is green. And with my editors, like, isn't there something deeper here? What really happened? And what did you learn? And what can other people? So it's one thing to say, like, my dad was a North Korean escape, like that sounds nice, um, like headline, like clickbait, basically.
unknownRight.
SPEAKER_01Uh, but what is what did it mean for him? What did it mean for me and my relationship to him? And how does it um how do I carry that? Right, the big bold steps that he had taken and apply it to big bold steps that I had taken also in my young life, and to understand that we were really quite the same. We both had this uh adventurous desire to see the world and break boundaries. And I didn't understand that when I was younger, but I understand that now.
SPEAKER_00So when uh you're looking back and see the same story, would you say that you tell the same story differently in a way that your experience has shaped you, and now you see your past differently? You hinted that that every so uh when you were going through that, uh it was intense, but now when you're looking um back, uh you hinted that uh not everything happened to you, that something happened for you with and that this is the way that you want to see your stories. Is that correct?
SPEAKER_01Yeah, I think that's the process of owning the story, or uh the architecture of the story, is thinking like what all of the things that happened and what do they mean to me now? So, one of the stories is my younger brother had a massive stroke when he was 43. And it was, as a lot of people have experienced stroke in a family, it is traumatic, it is um kind of changes everything, it's very like disorder, there's so much chaos, so many things to learn. Uh, it's very disruptive. Uh, and it was very, very hard, extremely hard. Uh, I'm now his full guardian, I was his healthcare advocate, I was taking care of all of his uh life uh aspects as well. And when I look at it now during it, during it, it was very hard. And telling people the story, people have a lot of empathy and sympathy for me because it was hard, and it was hard for our family. Looking back at it now, in retrospect, more than 10 years, is I understand it from a real deep sense of gratitude. In the middle of it, it was so painful, so painful. Uh, and after it is this thing that gave me two things. One is it gave me the ability to demonstrate my love for my little brother through dedication, through just dedicated service for months and months and months. And that was something for me is such a big gift. And I know when I see him now, he feels loved. Like he does not doubt love. And I think that is the most important thing that's come out of this, primarily. Secondarily, I feel it's gonna, it's gonna sound maybe egotistical, but I feel so good about myself, the way that I showed up. And yeah, I've been an investment banker, I went to MIT for graduate school, I did all these things, uh, and I can talk about my accomplishments. But to know for myself, right, that I'm the person that shows up, that I'm the person that prioritized my love for him in this really difficult situation, it helps me love myself.
SPEAKER_00Amazing story. Um can I go uh a bit deeper into how you understand uh midlife crisis because that was one of the crises and it happened around your midlife. But how you understand midlife crisis and if possible, um how how do you see differently than a mainstream US uh is seeing midlife crisis now? Because mainstream US, if I may be uh a bit uh uh if I may be a bit of a simp here, uh they see it as getting uh either uh divorce and uh buying a sports car or something like that. But there are so many layers to midlife crisis, and you mentioned that uh things change and that we have a new insight. Can you talk uh about uh your point of view of uh midlife crisis with your experience, uh with your background, how you see it? Is it is it something we should be ashamed of, or is it something we should learn about in school and to be prepared for that uh time?
SPEAKER_01Yeah, it's such a good question. You know, the my last uh startup was in menopause. So menopause is the big midlife journey for women. And yeah, I agree. In America, we're like midlife crisis, and we have to lash out and do all these things to compensate. I look at I look at midlife as a place where we have to understand the delta. And the delta is right, where we expect it to be and where we are. So that's one, right? Am I 45 and expect to look like I'm 35? Am I 55 and expect my knees to work like I'm still 22? Right. So this is like, what's the delta where I am now to understand, like almost like take your assessment? Like, here I am now, and what's troubling me? Right. So for women, it's a lot of aging, how my face ages, how my body ages, how I become increasingly irrelevant and visible to society, which uh is so obsessed with youth culture. Right. So, how do we deal with that? And that's something we have to hold for ourselves, right? What's the delta? How do I feel about myself now? How do I want to look? And how much is outside of me? Right. So that process is part of midlife for women. I think the other part is about understanding the delta from the plan, right? So when I was when I was in college, my grandfather, he wasn't his like not actually my grandfather, but my grandfather uh in name and relationship to the family. Uh, he was an important part. He said to me, Okay, you're 20 now, you'll get married when you're 23, you'll have some kids, you'll start having kids in your family when you're 26. He's, you know, telling me my life. And I really held on to that for a long time. And I thought I'm missing the plan, his plan. And by default, it, you know, I had to buy into that plan. So when I turned 37, I thought, oh shit, like I'm 10 years off the plan, right? Or 11 years off the plan. And it's problematic, right? Because I'm so we're so fixated to the plan. What's your plan? Have you achieved your plan? And what I know now, and part of going back to the memoir, is the plan that you have for your life, no matter how smart you are or thoughtful or like purposeful you are, can't hold the life that's awaiting for you. It can't, you have no idea who you can be, right? What's in store for you, good and bad, right? Life happens, strokes happen, right? A flash of an idea to write a memoir just happens. And so I I think we have a lot of difficulty midlife because we're expecting to be somewhere else. So that's one. The other is the emotional part tied to not being on the planet, right? So we talk a lot about discontent. I was listening to tons of um podcasts and reading Substacks about this. Like we are why why did we do everything right and yet feel today so discontent?
unknownRight.
SPEAKER_01And it's not I'm not happy, I could be happy, but for me, it's it's about contentness. How do I feel about my world around me, about my home, about my relationships? And that to me is the root of the midlife crisis. It's not so obvious where you're like, you know what, I need a Ferrari. So I'm just gonna get a Ferrari. Do I look great? I'm gonna drive in front of my friends, it's gonna solve some need, but it's not a deeper level of content. Like, what is contentedness? And I think the cool thing about midlife is we've had enough life now that we have the capability to start understand closer, get deeper from happiness. Why am I not happy? To what will make me content. And I think that's harder when you're 25. It's maybe impossible when you're 25, but you see a lot of young people that really know themselves. So I'm very I'm admired it very much. I think people who our age, uh, late millennials and Gen Xers, are like really struggling with like who we are and who we can be and what's supposed to happen. Uh, so that's my perspective. The plan, it's okay to be off plan, right? In fact, open yourself up to being more off plan and then find what's shaking you about your contentedness.
SPEAKER_00Amazing. Jean, can you tell us a bit more about what you do uh next to just uh writing the memoirs? Because I'm sure that that is not the only thing you do. And can you tell our audience a bit more? Because you're experts in so many fields. So uh what are you working on now?
SPEAKER_01Right now, so uh with the memoir, the extension from the memoir is I want to start speaking, and I want to start talking about this idea of where you are in your life right now, looking back, looking back at all the decision points, say the places where you said yes, where you went off your plan, and what it gave you. And then what it gave you, you own that so that you can make your next yes. And the reason I want to share it like that is this is how I understand it in my life. When I was an investment banker, I quit, I became a yoga teacher. I was at a yoga studio, and after class, a woman said, you know, I'm going to go to this yoga teacher training. She's going to be a teacher. And this woman was, I didn't know it then, but she was the local one of the drug dealers in the neighborhood. And I was like, wait a minute, a drug dealer is gonna become a yoga teacher? I was like, that's impossible. I go, she's gonna do it, I'm gonna do it. And so I went. This idea, like I said yes to something that was so crazy that she was doing it, that I was doing it, it was also crazy, but I said yes. After I became a yoga teacher, I had the opportunity to open a yoga studio in Singapore. Also, completely crazy. I was an investment banker, I never thought to run my own business, I had zero skills, but I said yes. And I did it, and it turned out I was pretty good at it. I have a very business brain, which I never would have understood if I not didn't say yes. So I did those two things and it changed my life. I taught yoga students, I had yoga studios, I had teacher trainings where I uh transformed yoga students into teachers from 40 different countries. It was super rewarding. And then when I hit perimenopause and I decided to start a company. And because I had done these things, because I'd worked directly with people, because I'd already started a bunch of businesses, I didn't hesitate. That yes was, I didn't even think about it. When I look back, it's because I said those other yeses, because I'd shown myself the pieces of what was inside me that I didn't know before, that I could own that. This is all in retrospect, right? So now I'm looking back when I opened the menopause company. I didn't think about owning these skills, but intuitively I did. And so I opened it. And so what I want to do for the book is start talking about this process. Take a moment, map your yeses, map the big decisions, map where you went off plan, right? Understand what it gave you, but proved about yourself so that this can be preparation for your next yes. So that's the book part. The other part, of course, you won't be surprised is I'm leaning into AI, which is not, and this is um perfect for the conversation about midlife because you never know what is next. I am not a software person at all. I mean, I just dabble as a consumer, but I've never built any software. And I'm leaning in with my partner, my fiance. He's built uh a product, an enterprise product with using AI tools. And we're looking into how we lean into small medium businesses, give them a light build on AI tools so they can solve some of the really intractable problems in running their business. And so this is something that I'm getting starting to geek out on a little bit of AI tooling, but mostly about, and this is where I excel is what are business processes in place? What is the goal? What are the problems here? What screwed up about it? What can we fix? Like I love fixing business problems. So this is something I'm just starting to dabble in, which is very um, it makes me laugh because I'm not at all your typical AI software person, but it's kind of cool.
SPEAKER_00Yeah, amazing. Gene, where can our uh listeners and viewers get in touch with you?
SPEAKER_01Oh, you can find me at my website, which is www.geneshunk.com, J-E-A-N-N-E-C-H-U-N-G.com. It has kind of the story, it has a link for my memoir once it's published, and also has a link you can do a you can do a worksheet for mapping your yeses.
SPEAKER_00Amazing. Gene, thank you for all these insights. It was really nice talking to you. Uh, and uh thank you for being my guest tonight.
SPEAKER_01Yeah, thank you for having me. It was a great conversation, really appreciate it.