Hi Hannah! I’m way out of your target demographic, but 20 years ago this was me right after getting my MBA from INSEAD and feeling pretty miserable as a management consultant. But I will tell you this — at 50 most of us are still going through the same thing. Getting laid off by ageist Corporate America, having to cover a big mortgage with another 10-20 years of raising kids ahead of us. A steady income these days is a blessing and often more important than excitement at work. If I could go back to 30, I would have picked a path that ages well, where experience is valued as knowledge and wisdom and not a sign of being outdated or expired. Personally I would have become a doctor, but other paths that value age include professor, therapist, politician… okay I guess not that many, I wish there were more. Anyway my point is similar to your first one — this is a problem as old as humans, but it’s also a problem that doesn’t get “solved”. And AI is only making the future of careers more uncertain. These days my thought is this: choose a path that requires you to be a physically present human. I might start over at 50 as a nurse.
This is awesome. One of the things I struggle the most with is finding the motivation to inspire all of the young women coming out of school and looking for advice. I’m starting this account for exactly that
Caroline, this resonates so much! The journey really is the same regardless of when you did your MBA. One thing I'd add, I went into my MBA with significantly more experience than most of my classmates, which shaped my expectations entirely differently. I however fell for the noise of corporate, when I was already past that phase and looking for something deeper, impact, building, sustainability. That gap between what the MBA promises and what it actually delivers on entrepreneurship is real, and I felt it sharply. Like you, I wish I'd spent more time building for myself than playing the traditional MBA game. Your point about choosing paths that age well really hit home, experience should be a currency, not a liability.
fellow INSEADer here! Your note about what you would do at 30 feels a propos, I've just arrived there. I think I agree with your point about finding professions where they value experience in a career, though I think a common thread across the ones you listed is they feel fundamentally human in a way so many ever-changing corporate careers do not, and also involve serving other humans in some capacity. Maybe that's imposing my own views and current direction I'm moving towards.
Wow what a great response! This really has me thinking. I’ve been thinking a lot about how to “future-proof” my career because of ageism in the work place. I’m no where near 50 but I’m anxious for sure. Now I’m thinking that for age 50 and beyond, having my own business might just be the way. What business? I don’t actually know. Just a thought about what would make sense for my future.
The line I keep coming back to is “stop trying to manufacture an interest that isn’t there.” Most advice in this genre can’t bear to say that—it has to promise a hidden passion if you just journal hard enough. There’s a quieter version I’ve lived, where the not-knowing wasn’t a fog to clear so much as a room I had to actually live in for a while before anything honest showed up. The side quests didn’t hand me the answer; they just gave me enough quiet to stop auditioning for the old one. Enjoy the two weeks fully offline—that’s its own kind of side quest. 🫶🏻
Hi Hannah, thank you I needed to read this today, it’s honest and describes exactly how I’m currently feeling. Love the tarot too! It was really insightful
The fog you're describing is its own kind of honesty. Not the brain overworked and needing recovery, but the specific numbness that comes after years of chasing targets that were never actually yours. You say "stop trying to manufacture interest" but the thing you're circling is harder: you've spent so long borrowing other people's definitions of what excites you that you've forgotten what it looks like when something speaks to you first, before the ambition calculates its worth. How do you rebuild a voice when the system that trained you to be excellent at shutting it down was actually, in every measurable way, working?
We hit the ground running so young. Study, get the good job, chase the promotion, head down, never coming up for air. Then the older we get, the better we know ourselves (well, I'd like to think we do), and we start questioning what we're actually doing and where it's going. Maybe being stuck isn't a breakdown at all. It's just the first time we’ve had a chance to put our heads up long enough to look around.
Love your posts Hannah. I quit my job and while in phase #2 of resting it actually gave me the room to think and create, and ultimately inspired me to write on substack and create a wellness app to help regulate the nervous system - https://sakoon.ai
I wrote an article on my page called “access is not the problem, focus is.” It’s about how our “potential” is dangerous as ambitious people and talks about some things to do when you’re confused about what to work on! May be useful to some people here
I consistently get stuck in my head and find motion to be the best way out of it. A very tactical reset I found effective was “The 12 hr walk.” It hits most of these points and is a simple decision to just set aside a day of your life.
1. Walk for 12 hrs, take as many breaks as you want
2. Start and end at your house so it’s contextualized to your daily life and not compartmentalized to an exotic trek
3. Do it by alone and actively mitigate extended human interactions
4. Airplane mode/ no music
The guy that made it has a book and whole thing - I found it useful!
The distinction between nothing feeling interesting and having too many interests is doing a lot of work here - though I've felt myself oscillating between both across different periods of my life. We tend to prescribe focus for both, but narrowing your options makes little sense when none of them feels worth pursuing. I'm definitely in your target demographic (INSEAD MBA, corporate > startup world) and I think the AI era has amplified both those feelings at the same time whereby everything you were once interested in, every niggling idea feels possible, and could be pursued with greater ease than before but then also the question of where do you come in? If everything is possible because it can be delegated to a system, as someone whose built their identity on increasingly replicable 'intellectual skills' what is left that actually feels worth pursuing?
The distinction between consuming clarity and generating it is the one I'd keep from this whole piece. I spent about two years thinking my way through a career shift that only clarified when I actually did something small and badly. The information you get from that is different from any reading.
I’ve genuinely never heard anyone articulate this feeling in a way that’s so eloquent but still SO relatable. It feels like you’re talking to a friend who’s giving you advice from lived experience. Absolutely loved this one!!
This definitely applied to me when I first started working after being at uni. It was incredibly difficult seeing online all the paths my friends were taking and doubting if you’re making the right choice. You’re right- sometimes we need to step back and take a view. Such a helpful read!
Yes!! I quit my management consulting job nearly 10 years ago, and moved to East Africa to build agriculture businesses that serve farmers who make less than 2 dollars a day. I love your point about just doing something, anything! We can only get more data points with more action. PS I am obsessed with a good side quest.
Hi Hannah! I’m way out of your target demographic, but 20 years ago this was me right after getting my MBA from INSEAD and feeling pretty miserable as a management consultant. But I will tell you this — at 50 most of us are still going through the same thing. Getting laid off by ageist Corporate America, having to cover a big mortgage with another 10-20 years of raising kids ahead of us. A steady income these days is a blessing and often more important than excitement at work. If I could go back to 30, I would have picked a path that ages well, where experience is valued as knowledge and wisdom and not a sign of being outdated or expired. Personally I would have become a doctor, but other paths that value age include professor, therapist, politician… okay I guess not that many, I wish there were more. Anyway my point is similar to your first one — this is a problem as old as humans, but it’s also a problem that doesn’t get “solved”. And AI is only making the future of careers more uncertain. These days my thought is this: choose a path that requires you to be a physically present human. I might start over at 50 as a nurse.
Thank you for sharing your retrospective!
This is awesome. One of the things I struggle the most with is finding the motivation to inspire all of the young women coming out of school and looking for advice. I’m starting this account for exactly that
Caroline, this resonates so much! The journey really is the same regardless of when you did your MBA. One thing I'd add, I went into my MBA with significantly more experience than most of my classmates, which shaped my expectations entirely differently. I however fell for the noise of corporate, when I was already past that phase and looking for something deeper, impact, building, sustainability. That gap between what the MBA promises and what it actually delivers on entrepreneurship is real, and I felt it sharply. Like you, I wish I'd spent more time building for myself than playing the traditional MBA game. Your point about choosing paths that age well really hit home, experience should be a currency, not a liability.
fellow INSEADer here! Your note about what you would do at 30 feels a propos, I've just arrived there. I think I agree with your point about finding professions where they value experience in a career, though I think a common thread across the ones you listed is they feel fundamentally human in a way so many ever-changing corporate careers do not, and also involve serving other humans in some capacity. Maybe that's imposing my own views and current direction I'm moving towards.
Wow what a great response! This really has me thinking. I’ve been thinking a lot about how to “future-proof” my career because of ageism in the work place. I’m no where near 50 but I’m anxious for sure. Now I’m thinking that for age 50 and beyond, having my own business might just be the way. What business? I don’t actually know. Just a thought about what would make sense for my future.
The line I keep coming back to is “stop trying to manufacture an interest that isn’t there.” Most advice in this genre can’t bear to say that—it has to promise a hidden passion if you just journal hard enough. There’s a quieter version I’ve lived, where the not-knowing wasn’t a fog to clear so much as a room I had to actually live in for a while before anything honest showed up. The side quests didn’t hand me the answer; they just gave me enough quiet to stop auditioning for the old one. Enjoy the two weeks fully offline—that’s its own kind of side quest. 🫶🏻
Ok I love this comment bc I’ve never been able to journal consistently in my life and think “just go journal” is the worst advice in the world
Hi Hannah, thank you I needed to read this today, it’s honest and describes exactly how I’m currently feeling. Love the tarot too! It was really insightful
The fog you're describing is its own kind of honesty. Not the brain overworked and needing recovery, but the specific numbness that comes after years of chasing targets that were never actually yours. You say "stop trying to manufacture interest" but the thing you're circling is harder: you've spent so long borrowing other people's definitions of what excites you that you've forgotten what it looks like when something speaks to you first, before the ambition calculates its worth. How do you rebuild a voice when the system that trained you to be excellent at shutting it down was actually, in every measurable way, working?
So true! It’s like the key to incubation effect is slowing down when all you want to do is push harder to solve the problem
We hit the ground running so young. Study, get the good job, chase the promotion, head down, never coming up for air. Then the older we get, the better we know ourselves (well, I'd like to think we do), and we start questioning what we're actually doing and where it's going. Maybe being stuck isn't a breakdown at all. It's just the first time we’ve had a chance to put our heads up long enough to look around.
Love your posts Hannah. I quit my job and while in phase #2 of resting it actually gave me the room to think and create, and ultimately inspired me to write on substack and create a wellness app to help regulate the nervous system - https://sakoon.ai
I wrote an article on my page called “access is not the problem, focus is.” It’s about how our “potential” is dangerous as ambitious people and talks about some things to do when you’re confused about what to work on! May be useful to some people here
I consistently get stuck in my head and find motion to be the best way out of it. A very tactical reset I found effective was “The 12 hr walk.” It hits most of these points and is a simple decision to just set aside a day of your life.
1. Walk for 12 hrs, take as many breaks as you want
2. Start and end at your house so it’s contextualized to your daily life and not compartmentalized to an exotic trek
3. Do it by alone and actively mitigate extended human interactions
4. Airplane mode/ no music
The guy that made it has a book and whole thing - I found it useful!
https://12hourwalk.com
This is so helpful, thank you 🫶🏼
The distinction between nothing feeling interesting and having too many interests is doing a lot of work here - though I've felt myself oscillating between both across different periods of my life. We tend to prescribe focus for both, but narrowing your options makes little sense when none of them feels worth pursuing. I'm definitely in your target demographic (INSEAD MBA, corporate > startup world) and I think the AI era has amplified both those feelings at the same time whereby everything you were once interested in, every niggling idea feels possible, and could be pursued with greater ease than before but then also the question of where do you come in? If everything is possible because it can be delegated to a system, as someone whose built their identity on increasingly replicable 'intellectual skills' what is left that actually feels worth pursuing?
I am such a big fan of your content. I started substack because of you and today is my first day. Thanks so much :)
I’m so honored to hear that!!!!
The distinction between consuming clarity and generating it is the one I'd keep from this whole piece. I spent about two years thinking my way through a career shift that only clarified when I actually did something small and badly. The information you get from that is different from any reading.
Really resonated with this one
I’ve genuinely never heard anyone articulate this feeling in a way that’s so eloquent but still SO relatable. It feels like you’re talking to a friend who’s giving you advice from lived experience. Absolutely loved this one!!
Aw happy to hear!
This definitely applied to me when I first started working after being at uni. It was incredibly difficult seeing online all the paths my friends were taking and doubting if you’re making the right choice. You’re right- sometimes we need to step back and take a view. Such a helpful read!
Yes!! I quit my management consulting job nearly 10 years ago, and moved to East Africa to build agriculture businesses that serve farmers who make less than 2 dollars a day. I love your point about just doing something, anything! We can only get more data points with more action. PS I am obsessed with a good side quest.
That’s so cool!