This is the most honest, heartfelt, and beautifully expressed essay I’ve ever read. I’ve been in the valley myself for the past three years and still can’t see the second mountain. Your words made me feel seen. Every line resonated deeply.
Thank you for creating something so beautiful and moving Andy!
Do your best to remind yourself that the valley is an invitation to connect deeply with yourself. It's an opportunity for rebirth. And you may also find that the second mountain isn't a mountain at all. Maybe, it's a river to float down gently :)
I am quite sure that you don't follow Indian cinema. There is this beautiful movie (Tamasha) on this topic in Hindi language - https://www.imdb.com/title/tt3148502/
True! For a millennial like me, Tamasha is the most cathartic experience. It’s like peeling an onion. Each layer reveals something new about me and there is new meaning every time you see it. I have made a habit of watching it every few months.
Andy, thank you for writing this. I am in the valley between 2 mountains right now as my first mountain was corporate America for the last 20 years until they blindsided me last summer. Now I am in the valley and reading your article makes me feel less alone. Your work is inspiring. 💜
I had to wonder if the Substack algorithm had access to my brain directly... lately I've been toying with the same intuition as you had—maybe what I was out to do, what I told the world I would accomplish no matter what, isn't what ultimately makes me happy. I'm still reeling on it, I am still feeling afraid and confused to whether I can leave this mountain behind (because I do not have a lot of money, my salary is not one of the US), but everyday the thought gets louder and louder... Your essay was very inspiring and, I think, most of all, the exact essay I needed to read. I am also happy you're better now, and I think you were very brave. Thank you very much for your words!
This moved me deeply. Thank you for sharing your story with such honesty, vulnerability, and clarity. You’ve given language to an experience many of us feel but rarely articulate so completely — the unraveling of identity, the ache of the valley, and the slow reassembling of self in a way that feels more true.
So many lines echoed parts of my own path, but this one especially stopped me: “The work to be done here is not on your laptop. The work is with your body, mind, heart, and soul.” That hits. The productivity patterns, the desire to fix or accelerate the process, the inner bargaining — I know them well. And yet, as you write so beautifully, it’s the slowing down, the listening, the making space that allows something real to emerge.
I’m incredibly grateful for this reflection. Not just for how much it resonated, but for the care and depth you brought to every section. It’s a gift to feel less alone in this kind of transition — to be reminded that the fog, the grief, the nonlinear progress… all of it belongs.
Thank you again for walking this path and sharing the view.
Thank you. I am in my 4th year of retirement after a 35 yr career as a surgeon and educator. I’ve experienced everything you’ve described, and I’ve struggled to explain what I’m experiencing, even to those closest to me. Your words and insights felt as though we were occupying the same existence, even the same consciousness, so precisely did you describe my journey. The hardest part for me has been the realization you described that so many of the people I thought were my closest friends were, in fact, just professional acquaintances, their affinity for me transactionally based on what I did, not who I am. It was only when I read your piece that I understood that this is natural, and not a failure on either of our parts. That has allowed me to let go of the hurt I’ve been experiencing, and the loss. Thank you again, and good luck on your journey.
Thank you very much for sharing. It means a lot to receive a message like this. Everything is changing at all times—it always has and always will. Change is the fundamental constant. That naturally includes the people we relate to throughout a lifetime. Those relationships served a role for a stage of life. I'm sure many positive memories. But sometimes, we move on and have to let go, which includes recognizing the good memories and the bare truth that they may no longer be the right relationships. Holding both simultaneously is the way to make peace with it :)
This has put into words a lot of what I've been going through. Not just the rejection of the previous life but also the weird things out brains try and trick us into doing.
I was a serial entrepreneur and we recently inherited enough to live on for the rest of our lives, as long as we keep a little coming in with some passive side projects.
But my brain had been so wired to constantly expand and create from my entrepreneur days that I spend hours planning and researching new ideas only to realise this isn't what I want, and that I'm giving myself a job I don't need just to align to someone else's idea of success.
I see other people in my field launching things and think, I could do that, but I don't want to. So I'm learning that just because I CAN doesn't mean I SHOULD.
It was almost simpler when I needed the money, because then these ideas would make sense to pursue. When you have the money not to work, then you come up with an idea that would make money but involve you now working then it doesn't make sense.
I suppose my challenge is that every thing that isn't purely hedonistic involves some degree of external validation (otherwise we'd all be volunteering on children cancer wards), so where is the line between wanting to achieve something and it only being for your ego?
It’s ok if the desire to create or achieve comes from ego/identity, so long as it’s not coming from a place of feeling less-than or not good enough. If it’s coming from an identity that feels whole, then bring whatever it is you want into the world. That’s the key distinction.
An identity based on feeling less-than can be a powerful driver for survival, especially if coming from a difficult childhood. In that case, it serves an important purpose of survival. But, if you feel less-than AND you aren’t in an insecure or difficult situation, then it’s the wrong ‘fuel source’ powering your desire to create and achieve.
It’s all about if it’s the right ‘fuel source’ given your situation. Find your way to feeling whole and good enough, and then create and achieve from that basis.
This is possibly the single most true and beautifully written piece I’ve read yet on Substack. It’s like you’ve written about what’s happening to me right now. Boy is that valley hard going but I’m starting to glimpse a path, or at least I’m carving one. Thank you for writing this, I hope one day my writing reaches this quality and profundity
A dear friend, my spiritual partner/guide sent this to me, and it resonates deeply. However, I must interject a perhaps, heretofore (I didn't read all 176 comments so I go on assumption), "zinger"into the conversation. Death. Imminent. the beauty and struggle you discuss with clarity and heart, come up against a full stop; the knowledge that death is near, and possibly only half way up the mountain, renders the wandering in the valley even more fraught with loss and wandering. Doubly so when faced with two losses at once.
In the summer of 2023 I lost the love of my life, my inner compass, my reason for being; my husband of 43 years. Four months later I was diagnosed with terminal cancer. One to five years, I'm entering year 3, possibly, maybe, less, but not more, no one knows, we'll see how treatment goes or doesn't.
The beauty and struggle you discuss, wandering the valley, finding the trailhead, taking the first steps upward, for me, come face to face with this reality.
I had to drop out of my much loved workplace within 30 days of my diagnosis to start treatment. I was not struggling in a position I yearned to change; conversely, it was a life-line between losing my beloved and starting a new solo life, a job I loved...and then all that changed. Over the course of the past year I've released my identity with my job and have embraced my unstructured time. But I am cast adrift in the valley. I look to my spiritual path, it gives me solace, for a time, but the questions surrounding "what is living, and where do I belong" take on special meaning when the clock in the room isn't a reminder of time passing, but a reminder that "it's not time that passes, but us"...I offer this as another thread to weave into your excellent narrative. I am an innately positive person and am living every day, but never forget, dear reader, that disappearance, or transition, whichever death turns out to be, is a mystery to be considered on this road called life.
Love & resonate with your story. I retired early from Silicon Valley 5 years ago & have never looked back.
I lost my beloved husband to a small plane accident just as we gave notice at work. As I grieved & healed, I found love again. I learned so much once I let go of control & opened myself to allow things to happen at the natural pace of the “River of life”. Discovered inner spaciousness & how to live life fully in the present moment! I wrote about this journey in my book Forever Fly Free which launches this October.
My favorite quote is from Eckhart Tolle - “Life’s and adventure not a packaged tour!”
I look forward to reading more of your writing as you continue your journey. I joke about making a prison break from SV. But we are all on our path to learn our life lessons. We can help others more when we’ve struggled ourselves.
That's exactly right. We take our pain and transmute it into a gift that helps replenish others. That's how this works :) You're doing inspiring work, Jenny. Best of luck to you!
I feel *so* caught in the grey areas of life right now. Not just leaving a career in tech (either temporarily or permanently, don't know yet), but becoming a new mother and navigating marriage with someone who grew up in a different culture.
Like you, I consider my daily walks a lifeline. I also find cooking very grounding, which I suppose is my version of the embodiment that you spoke of feeling after leaving the grind of the tech world.
But I miss the intellectual stimulation of my former career, and I yearn for more conversations that are not about motherhood. I find inspiration in a few podcasts, as well as your writings.
Although I sometimes have a short attention span these days, I loved reading this long essay from start to finish. Thank you much!
Such a thoughtful and well written article. Everything resonated with me. This has been my first hand experience - "Many experience a heightened sensitivity to beauty and meaning during transition. Without the deadening effects of chronic stress and overwork, your perceptual field expands. " Thanks so much Andy!
Dude. Well, well, well let me shake your hand and "hell, yes" high-five ye on your articulations and observations. SO GOOD! This rules. As someone who also actively choose to enter their valley (and is very much still residing in traversing its expanse), so much of this speaks resonant. Thank you for this energy... your experiential expression without-a-doubt helps me personally feel seen, understood, and less alone in the mystery, uncertainty, and hope of it all. Nice to "meet" you, fellow traveler.
This is the most honest, heartfelt, and beautifully expressed essay I’ve ever read. I’ve been in the valley myself for the past three years and still can’t see the second mountain. Your words made me feel seen. Every line resonated deeply.
Thank you for creating something so beautiful and moving Andy!
Do your best to remind yourself that the valley is an invitation to connect deeply with yourself. It's an opportunity for rebirth. And you may also find that the second mountain isn't a mountain at all. Maybe, it's a river to float down gently :)
Thanks for the advice Andy! Will keep coming back to this essay.
There is lot of suffering in the process though. Feels quite tough. Tougher than everything else I have done so far.
Same. It's been one of the greatest challenges in my life. Transformation doesn't come easy.
I am quite sure that you don't follow Indian cinema. There is this beautiful movie (Tamasha) on this topic in Hindi language - https://www.imdb.com/title/tt3148502/
Just thought of sharing with you :)
True! For a millennial like me, Tamasha is the most cathartic experience. It’s like peeling an onion. Each layer reveals something new about me and there is new meaning every time you see it. I have made a habit of watching it every few months.
thank you!
Andy - this is such a heart felt article ! Thank you for doing this …
Andy, thank you for writing this. I am in the valley between 2 mountains right now as my first mountain was corporate America for the last 20 years until they blindsided me last summer. Now I am in the valley and reading your article makes me feel less alone. Your work is inspiring. 💜
Thank you, Tam. You're definitely not alone.
I had to wonder if the Substack algorithm had access to my brain directly... lately I've been toying with the same intuition as you had—maybe what I was out to do, what I told the world I would accomplish no matter what, isn't what ultimately makes me happy. I'm still reeling on it, I am still feeling afraid and confused to whether I can leave this mountain behind (because I do not have a lot of money, my salary is not one of the US), but everyday the thought gets louder and louder... Your essay was very inspiring and, I think, most of all, the exact essay I needed to read. I am also happy you're better now, and I think you were very brave. Thank you very much for your words!
Thank you, Andrea.
This is a deeply reflective and beautifully written piece Andy. I appreciated the long format that asked that I give it my undivided attention.
It’s an earned piece.
I can tell you’ve spent time in the valley and learnt to reconnect with your body’s wisdom.
Thank you for sharing it with the world. There’s some beautiful insights in it that will resonate with others!
Thank you, Arthur!
This moved me deeply. Thank you for sharing your story with such honesty, vulnerability, and clarity. You’ve given language to an experience many of us feel but rarely articulate so completely — the unraveling of identity, the ache of the valley, and the slow reassembling of self in a way that feels more true.
So many lines echoed parts of my own path, but this one especially stopped me: “The work to be done here is not on your laptop. The work is with your body, mind, heart, and soul.” That hits. The productivity patterns, the desire to fix or accelerate the process, the inner bargaining — I know them well. And yet, as you write so beautifully, it’s the slowing down, the listening, the making space that allows something real to emerge.
I’m incredibly grateful for this reflection. Not just for how much it resonated, but for the care and depth you brought to every section. It’s a gift to feel less alone in this kind of transition — to be reminded that the fog, the grief, the nonlinear progress… all of it belongs.
Thank you again for walking this path and sharing the view.
Thank you for such an eloquent response. You said it well :)
Thank you. I am in my 4th year of retirement after a 35 yr career as a surgeon and educator. I’ve experienced everything you’ve described, and I’ve struggled to explain what I’m experiencing, even to those closest to me. Your words and insights felt as though we were occupying the same existence, even the same consciousness, so precisely did you describe my journey. The hardest part for me has been the realization you described that so many of the people I thought were my closest friends were, in fact, just professional acquaintances, their affinity for me transactionally based on what I did, not who I am. It was only when I read your piece that I understood that this is natural, and not a failure on either of our parts. That has allowed me to let go of the hurt I’ve been experiencing, and the loss. Thank you again, and good luck on your journey.
Thank you very much for sharing. It means a lot to receive a message like this. Everything is changing at all times—it always has and always will. Change is the fundamental constant. That naturally includes the people we relate to throughout a lifetime. Those relationships served a role for a stage of life. I'm sure many positive memories. But sometimes, we move on and have to let go, which includes recognizing the good memories and the bare truth that they may no longer be the right relationships. Holding both simultaneously is the way to make peace with it :)
This has put into words a lot of what I've been going through. Not just the rejection of the previous life but also the weird things out brains try and trick us into doing.
I was a serial entrepreneur and we recently inherited enough to live on for the rest of our lives, as long as we keep a little coming in with some passive side projects.
But my brain had been so wired to constantly expand and create from my entrepreneur days that I spend hours planning and researching new ideas only to realise this isn't what I want, and that I'm giving myself a job I don't need just to align to someone else's idea of success.
I see other people in my field launching things and think, I could do that, but I don't want to. So I'm learning that just because I CAN doesn't mean I SHOULD.
It was almost simpler when I needed the money, because then these ideas would make sense to pursue. When you have the money not to work, then you come up with an idea that would make money but involve you now working then it doesn't make sense.
I suppose my challenge is that every thing that isn't purely hedonistic involves some degree of external validation (otherwise we'd all be volunteering on children cancer wards), so where is the line between wanting to achieve something and it only being for your ego?
I can't tell yet but I loved this article.
It’s ok if the desire to create or achieve comes from ego/identity, so long as it’s not coming from a place of feeling less-than or not good enough. If it’s coming from an identity that feels whole, then bring whatever it is you want into the world. That’s the key distinction.
An identity based on feeling less-than can be a powerful driver for survival, especially if coming from a difficult childhood. In that case, it serves an important purpose of survival. But, if you feel less-than AND you aren’t in an insecure or difficult situation, then it’s the wrong ‘fuel source’ powering your desire to create and achieve.
It’s all about if it’s the right ‘fuel source’ given your situation. Find your way to feeling whole and good enough, and then create and achieve from that basis.
I hope that helps.
This is possibly the single most true and beautifully written piece I’ve read yet on Substack. It’s like you’ve written about what’s happening to me right now. Boy is that valley hard going but I’m starting to glimpse a path, or at least I’m carving one. Thank you for writing this, I hope one day my writing reaches this quality and profundity
Thank you. That's very kind of you to say. Wishing you well on your journey!
I love the conclusion you come to, that there's wisdom in allowing ourselves to get lost. And that transformation needs gentleness to unfold.
Good morning Andy,
A dear friend, my spiritual partner/guide sent this to me, and it resonates deeply. However, I must interject a perhaps, heretofore (I didn't read all 176 comments so I go on assumption), "zinger"into the conversation. Death. Imminent. the beauty and struggle you discuss with clarity and heart, come up against a full stop; the knowledge that death is near, and possibly only half way up the mountain, renders the wandering in the valley even more fraught with loss and wandering. Doubly so when faced with two losses at once.
In the summer of 2023 I lost the love of my life, my inner compass, my reason for being; my husband of 43 years. Four months later I was diagnosed with terminal cancer. One to five years, I'm entering year 3, possibly, maybe, less, but not more, no one knows, we'll see how treatment goes or doesn't.
The beauty and struggle you discuss, wandering the valley, finding the trailhead, taking the first steps upward, for me, come face to face with this reality.
I had to drop out of my much loved workplace within 30 days of my diagnosis to start treatment. I was not struggling in a position I yearned to change; conversely, it was a life-line between losing my beloved and starting a new solo life, a job I loved...and then all that changed. Over the course of the past year I've released my identity with my job and have embraced my unstructured time. But I am cast adrift in the valley. I look to my spiritual path, it gives me solace, for a time, but the questions surrounding "what is living, and where do I belong" take on special meaning when the clock in the room isn't a reminder of time passing, but a reminder that "it's not time that passes, but us"...I offer this as another thread to weave into your excellent narrative. I am an innately positive person and am living every day, but never forget, dear reader, that disappearance, or transition, whichever death turns out to be, is a mystery to be considered on this road called life.
Love & resonate with your story. I retired early from Silicon Valley 5 years ago & have never looked back.
I lost my beloved husband to a small plane accident just as we gave notice at work. As I grieved & healed, I found love again. I learned so much once I let go of control & opened myself to allow things to happen at the natural pace of the “River of life”. Discovered inner spaciousness & how to live life fully in the present moment! I wrote about this journey in my book Forever Fly Free which launches this October.
My favorite quote is from Eckhart Tolle - “Life’s and adventure not a packaged tour!”
Jenny, thanks for sharing this with me. What a powerful story. I’m excited to read it.
I look forward to reading more of your writing as you continue your journey. I joke about making a prison break from SV. But we are all on our path to learn our life lessons. We can help others more when we’ve struggled ourselves.
That's exactly right. We take our pain and transmute it into a gift that helps replenish others. That's how this works :) You're doing inspiring work, Jenny. Best of luck to you!
It's like you were me from the future providing me with exactly what I needed to read/hear. Bravo! I'm blown away by this essay.
thank you :)
I feel *so* caught in the grey areas of life right now. Not just leaving a career in tech (either temporarily or permanently, don't know yet), but becoming a new mother and navigating marriage with someone who grew up in a different culture.
Like you, I consider my daily walks a lifeline. I also find cooking very grounding, which I suppose is my version of the embodiment that you spoke of feeling after leaving the grind of the tech world.
But I miss the intellectual stimulation of my former career, and I yearn for more conversations that are not about motherhood. I find inspiration in a few podcasts, as well as your writings.
Although I sometimes have a short attention span these days, I loved reading this long essay from start to finish. Thank you much!
Thank you, Ariel! You're going through a lot of change. I'm sending you love and support as you navigate it and allow it to unfold.
This was a challenge for me as my identity was my company. Good stuff.
Wrote about my experience here https://ainars.beehiiv.com/p/why-it-is-not-good-idea-to-merge-your-identity-with-your-business
Such a thoughtful and well written article. Everything resonated with me. This has been my first hand experience - "Many experience a heightened sensitivity to beauty and meaning during transition. Without the deadening effects of chronic stress and overwork, your perceptual field expands. " Thanks so much Andy!
Dude. Well, well, well let me shake your hand and "hell, yes" high-five ye on your articulations and observations. SO GOOD! This rules. As someone who also actively choose to enter their valley (and is very much still residing in traversing its expanse), so much of this speaks resonant. Thank you for this energy... your experiential expression without-a-doubt helps me personally feel seen, understood, and less alone in the mystery, uncertainty, and hope of it all. Nice to "meet" you, fellow traveler.
My pleasure, Mish! You definitely aren’t alone 🤝