Hey Yew Jin, just an appreciation comment! Everything you write is so deep and insightful. There’s so much thought and structure in the way you put things, and it comes through with such clarity. One thing that really resonated with me was: “Wandering isn’t the same as being lost. Lost is not knowing where you are. Wandering is exploring without a fixed destination. One is panic, the other is possibility.” Such a powerful statement. Please keep writing, I honestly haven’t come across thoughts this deeply rooted before :)
There are two realities: the one the news keeps bombarding us with about so and so having how many trillions and the things which sound like they are going to impact the world at scale. And in this reality, there are billions of regular individuals whose importance rounds to zero. Then there is that other reality, or rather the billions of realities of experienced life which includes the joy from family, friends and neighbors, which counts for nothing in the economy. In this reality, the contributions of the trillionaire pale in comparison to the well-seasoned turkey.
As an economist this bugs me, but it seems like most people find their way around it. Or do they? Maybe not enough. Especially when economic fear is such an effective and nowadays widely-wielded tool. Near death experiences help, but the insight attained that way often fades. Being aware of the constant and unpredictable possibility of death, morbid though it is, seems to be one of the few (hopefully not the only) durable ways, but it is hard to get past the fatalism that comes with having that as a philosophical grounding. Can one feel the same joy without also feeling the sorrow of impending loss of that moment? Not sure.
Hey Yew Jin, thanks for sharing your experience. I am on a similar journey, quitting tech, as an engineering director. Your reflections resonate with me, and one especially, although you don't mention this word explicitly: the extra *headspace*. Headspace to learn about random topics, headspace to listen to your subconscious, and crucially headspace for your relationships. Your friends, your family, your partner, now have your full attention. Relationships deepen, and there's still space for more.
Hi Yew Jin, your note resonated a lot with me. As someone who also works in big tech for a bit over a decade, I haven’t made the jump but recently I started to find myself scared when thinking about what if I work like this for another 10/20 years and could leave the world like this. By then I won’t feel I have expressed myself or left any personal trace behind. I find someone who simply does vlog probably showcased more of themselves than I do. In big corp life, I feel praised for solving problems like an intelligent machine, less so as a unique human being. Anyhow, thanks for writing this note. It gives me a bit more validation about what I’m feeling. And one day when the time is right, maybe the jump will reveal itself too. But for now, I will try to create space for wandering as much as possible. Enjoy your wandering and pls continue sharing your journey!🫡
Hey Yew Jin, thank you for sharing this. I'm in a different phase of life than you are, but if im lucky enough to find myself in your situation one day, I'll look back and reflect on this article.
I love this, thank you for writing Yew Jin. I also took my jump from Big Tech a couple years ago with a similar desire to pursue what felt meaningful to me. I actually read this Wait But Why article on how short life is (https://waitbutwhy.com/2015/12/the-tail-end.html) back then that inspired me to build a chrome extension to visualize my time left on my new tab page :) Now I spend my days building what I love, even if it doesn't scale 10x, and it's been a beautiful ride.
I installed LifeLeft and used it - although to be honest I did go back as I did miss my new tab page, but precisely the point to reflect on the finite moments we have left!!
This is a great writing - precisely what I have been thinking but with richer expansions. Particularly the part to scale - that makes human experiences inevitably becomes commodity. What we want is authenticity. Best luck to your future explorations!
This series was a fantastic read on career and life choices!
I personally resonated with the first two posts a lot, especially as a PM in their 30s reflecting on my own growth and future direction. The final post will definitely serve as a guide for what lies ahead. I really appreciate the entire perspective on time, identity, and what success truly means. This series is going to stick with me for a long time.
This is brilliant, and so resonant for someone on the same path. I move on in 2021 from senior role to being a solo - and pursuing things that don't scale, but lead to contentment. Thank you for writing this deep insightful piece that tells me, "you're not alone"
Hey Yew Jin, learned a lot from the post. Could you articulate on how you have experienced the compounding of freedom?. im curious to know the perspective that a 6-month break wont give v/s a full transition. I'm sure like everything in life, freedom also compounds, but unable to visualize given that most of us doesn't get a full break until retirement.
Thanks for the thoughtful question! In all honesty, ask me again in 3 months - I've only been out for 3 months myself, so I'm still in the early chapters of understanding how this freedom actually compounds. :-)
But here's what I can share so far: I was actually offered a 6-month sabbatical/extended leave, and I turned it down. For me, the difference was crucial - a sabbatical is a pause with an expiration date. I felt that I could never fully let go because I would be aware of the countdown.
My north star is spending meaningful time with my aging parents and my growing children. I didn't want to be mentally tracking how many weeks I had left before returning. I think there's something fundamentally different about jumping with no return ticket. And until all ties are actually cut, there is a part of me which would be still tethered.
The compounding I'm starting to experience comes from that complete loosening of ties. When there's no craving to anything work related, and I am imagining and digging into the alternatives - I am free to move in whatever direction feels right. Each day of not having to switch contexts back to the old identity makes the new path clearer.
It's early days, but the compound effect feels right now less like interest accumulating and more like shedding weight - each anchor I release makes the next step lighter. The compounding comes from the steps taken in the same direction after that.
Thank you for this breath of fresh air! It reminds me St. Thérèse of Lisieux who taught that you can find peace through simple, everyday actions—the "little things".
I smiled as I read this, my fellow traveler on this journey. My path is near identical with a few twists and turns, and am currently a few steps ahead of you.
After a couple of years stepping away from corporate America, I think I have found the energy to be curious again, and follow my curiosity wherever it may lead. The flicker of ambition is starting to burn again, but the destination is something quite different from where I planted my original flag. It’s still shrouded in haze and not perfectly visible, but I’m walking towards that anyway. I may veer off course and that is ok, the idea is to simply follow my curiosity till it crystallizes into conviction.
Thank you for sharing this glimpse of what's ahead. It's reassuring to hear from someone a few steps further along - especially that the curiosity does return and the ambition rekindies, just aimed differently. Right now I'm just writing and running. :-)
'Follow my curiosity till it crystallizes into conviction' - great phrase - wishing you clarity as the haze lifts, and enjoying hearing that veering off course is part of the journey, not a departure from it.
Hey Yew Jin, just an appreciation comment! Everything you write is so deep and insightful. There’s so much thought and structure in the way you put things, and it comes through with such clarity. One thing that really resonated with me was: “Wandering isn’t the same as being lost. Lost is not knowing where you are. Wandering is exploring without a fixed destination. One is panic, the other is possibility.” Such a powerful statement. Please keep writing, I honestly haven’t come across thoughts this deeply rooted before :)
Appreciate the kind note! I'm glad the writing resonates with you!
Huge +1 to this ^ , couldn’t have said it better.
There are two realities: the one the news keeps bombarding us with about so and so having how many trillions and the things which sound like they are going to impact the world at scale. And in this reality, there are billions of regular individuals whose importance rounds to zero. Then there is that other reality, or rather the billions of realities of experienced life which includes the joy from family, friends and neighbors, which counts for nothing in the economy. In this reality, the contributions of the trillionaire pale in comparison to the well-seasoned turkey.
As an economist this bugs me, but it seems like most people find their way around it. Or do they? Maybe not enough. Especially when economic fear is such an effective and nowadays widely-wielded tool. Near death experiences help, but the insight attained that way often fades. Being aware of the constant and unpredictable possibility of death, morbid though it is, seems to be one of the few (hopefully not the only) durable ways, but it is hard to get past the fatalism that comes with having that as a philosophical grounding. Can one feel the same joy without also feeling the sorrow of impending loss of that moment? Not sure.
Enjoyed this read a lot.
I went on a 12-month career break to live the first year of my daughter’s life.
It was the best decisione of my life (so far - I know I’ll take even better ones).
Welcome to Substack 🙂
Congrats on the brave (and best) decision! Best of luck!
Hey Yew Jin, thanks for sharing your experience. I am on a similar journey, quitting tech, as an engineering director. Your reflections resonate with me, and one especially, although you don't mention this word explicitly: the extra *headspace*. Headspace to learn about random topics, headspace to listen to your subconscious, and crucially headspace for your relationships. Your friends, your family, your partner, now have your full attention. Relationships deepen, and there's still space for more.
Hi Yew Jin, your note resonated a lot with me. As someone who also works in big tech for a bit over a decade, I haven’t made the jump but recently I started to find myself scared when thinking about what if I work like this for another 10/20 years and could leave the world like this. By then I won’t feel I have expressed myself or left any personal trace behind. I find someone who simply does vlog probably showcased more of themselves than I do. In big corp life, I feel praised for solving problems like an intelligent machine, less so as a unique human being. Anyhow, thanks for writing this note. It gives me a bit more validation about what I’m feeling. And one day when the time is right, maybe the jump will reveal itself too. But for now, I will try to create space for wandering as much as possible. Enjoy your wandering and pls continue sharing your journey!🫡
Thanks for the thoughts, though the gpt writing is shining through.
Hey Yew Jin, thank you for sharing this. I'm in a different phase of life than you are, but if im lucky enough to find myself in your situation one day, I'll look back and reflect on this article.
I love this, thank you for writing Yew Jin. I also took my jump from Big Tech a couple years ago with a similar desire to pursue what felt meaningful to me. I actually read this Wait But Why article on how short life is (https://waitbutwhy.com/2015/12/the-tail-end.html) back then that inspired me to build a chrome extension to visualize my time left on my new tab page :) Now I spend my days building what I love, even if it doesn't scale 10x, and it's been a beautiful ride.
Here's the link to that chrome extension in case it adds some joy to your day: LifeLeft - https://chromewebstore.google.com/detail/lifeleft/mmdgeflfnendogpjpfleimfgolkkljnb
Thanks for sharing, and I can't wait to stay tuned on your projects.
Great recommendation. I enjoyed the article!
I installed LifeLeft and used it - although to be honest I did go back as I did miss my new tab page, but precisely the point to reflect on the finite moments we have left!!
Love it, I'm glad you liked it! Indeed, let's make the most of our time in this beautiful life we get!!
This is a great writing - precisely what I have been thinking but with richer expansions. Particularly the part to scale - that makes human experiences inevitably becomes commodity. What we want is authenticity. Best luck to your future explorations!
This series was a fantastic read on career and life choices!
I personally resonated with the first two posts a lot, especially as a PM in their 30s reflecting on my own growth and future direction. The final post will definitely serve as a guide for what lies ahead. I really appreciate the entire perspective on time, identity, and what success truly means. This series is going to stick with me for a long time.
This is brilliant, and so resonant for someone on the same path. I move on in 2021 from senior role to being a solo - and pursuing things that don't scale, but lead to contentment. Thank you for writing this deep insightful piece that tells me, "you're not alone"
Hey Yew Jin, learned a lot from the post. Could you articulate on how you have experienced the compounding of freedom?. im curious to know the perspective that a 6-month break wont give v/s a full transition. I'm sure like everything in life, freedom also compounds, but unable to visualize given that most of us doesn't get a full break until retirement.
Thanks for the thoughtful question! In all honesty, ask me again in 3 months - I've only been out for 3 months myself, so I'm still in the early chapters of understanding how this freedom actually compounds. :-)
But here's what I can share so far: I was actually offered a 6-month sabbatical/extended leave, and I turned it down. For me, the difference was crucial - a sabbatical is a pause with an expiration date. I felt that I could never fully let go because I would be aware of the countdown.
My north star is spending meaningful time with my aging parents and my growing children. I didn't want to be mentally tracking how many weeks I had left before returning. I think there's something fundamentally different about jumping with no return ticket. And until all ties are actually cut, there is a part of me which would be still tethered.
The compounding I'm starting to experience comes from that complete loosening of ties. When there's no craving to anything work related, and I am imagining and digging into the alternatives - I am free to move in whatever direction feels right. Each day of not having to switch contexts back to the old identity makes the new path clearer.
It's early days, but the compound effect feels right now less like interest accumulating and more like shedding weight - each anchor I release makes the next step lighter. The compounding comes from the steps taken in the same direction after that.
Thank you
Thank you for this breath of fresh air! It reminds me St. Thérèse of Lisieux who taught that you can find peace through simple, everyday actions—the "little things".
I smiled as I read this, my fellow traveler on this journey. My path is near identical with a few twists and turns, and am currently a few steps ahead of you.
After a couple of years stepping away from corporate America, I think I have found the energy to be curious again, and follow my curiosity wherever it may lead. The flicker of ambition is starting to burn again, but the destination is something quite different from where I planted my original flag. It’s still shrouded in haze and not perfectly visible, but I’m walking towards that anyway. I may veer off course and that is ok, the idea is to simply follow my curiosity till it crystallizes into conviction.
Thank you for sharing this glimpse of what's ahead. It's reassuring to hear from someone a few steps further along - especially that the curiosity does return and the ambition rekindies, just aimed differently. Right now I'm just writing and running. :-)
'Follow my curiosity till it crystallizes into conviction' - great phrase - wishing you clarity as the haze lifts, and enjoying hearing that veering off course is part of the journey, not a departure from it.
Looking forward to reading about your journey and sharing any notes!
Love the title image (and of course the message!) big fan 🫶
Thanks! Lots of prompt engineering. Also thankfully Nano Banana is a thing otherwise I will go crazy with these AI art tweaks!!!