Great piece Iwana! Detaching your identity from corporate (especially in tech where emotional investment is expected) is from my experience one of the first (and not easy but) needed steps to think beyond false stability and security. I’m still in tech (by conscious choice) yet I have always had a portfolio of”small bets” on the side, sometimes more, sometimes less depending on my capacity. The danger is really to get too comfortable with the golden handcuffs and not carve out time to live a creative life full of different pieces of a puzzle.
Yeah, I think what you say is key. It's not about quitting today, but being aware of this, not getting too comfortable, questioning the status quo from time to time, and slowly building optionality on the side in whatever way your life allows right now.
The 'External security vs. internal safety' part is central I think. As you said, no matter how much money is in the bank, people always worry about money... or they don't.
Developing the internal safety side and believing in your core that no matter what, you'll be ok because of WHO you are (your identity, your abilities, your skills, etc) can be transformative.
Job security was something true for our parents... a few decades ago, having a job was actually safe in most countries. As you say, those days it means nothing. It's an old narrative we are holding on to... to feel safe I guess, and no freak out.
Money is such a "weird" thing also though. Ultimately who is right... the person putting money aside monthly to secure their future... sacrificing the now for a future not guaranteed... or the one enjoying life to the fullest now without thinking of tomorrow. There isn't a right answer I think.
I tend to approach it like that as well… building for the future without sacrificing today. It’s not always easy though, there are many temptations out there.
I burned out 3 times during my 25 years of work in tech. I decided to quit in 2015 and never looked back. What also helped me is a frugal lifestyle. What I believed I needed was simply a societal conditioning, implanted desire, not an authentic need. We only need air, water, food, and shelter. Luxury cars, lots of travel, and mansions are not necessary for a fulfilling life, but of course, the social media says you do.
It’s true that we often think it’s irresponsible to ‘leave money on the table’ and often feel safety is the constant thriving for more.
I know I have more than enough, yet sometimes it doesn’t feel like it. I’m about to go travelling in the summer in the nordics in our van, and my aim by then is to feel the security internally - to know that I can enjoy 2 months of travel with 15 hours of week working, and know it’s enough. Enough to live, develop myself, and most importantly be present in a once in a lifetime opportunity.
Thank you for reminding us that safety is a choice we can find within ourselves 💙
Thank you, Fiona! You‘re so right that it’s a choice we can find within ourselves and something we can train to get better over time. So glad you guys are taking the time to travel in the summer - sounds amazing!!!
“Portfolio careers aren’t meant to be fixed. They’re meant to evolve throughout life. Components are added, paused, or dropped as your interests, capacity, and circumstances change.” YES YES YES!!! This is what makes life so exciting! We are constantly co-creating!
Haha, love the enthusiasm! I couldn’t agree more, when I learned about portfolio careers, I got so genuinely excited about it and all the possibilities it creates for living life on my own terms!
So many golden nuggets in here - you’ve reminded me I haven’t done my financial
Floor in a while. Really worth me checking in on that even while I’m in this portfolio journey, it’s not just set and forget it! And I definitely find little tiny acts outside work that build self trust are super helpful
To manage the “planting seeds” phase of starting new
Reframing security as an inside job is one of the key mindset shifts we need to make right now. Trusting ourselves - backing ourselves - to find our way through this disruption is such an important part of building new approaches to life and career.
Great piece Iwana! Through some tough lessons I have had to learn that relying on the job market alone for security is not a good idea. Interests dont perfectly align. I’ve been introduced to the idea of a portfolio career through my time here on Substack, and the empowerment from being in charge of your own future is just different.
One key takeaway for me was pillar 4, diversifying your safety signal, to not just put money on a pedestal, ask yourself if youre happy with the hours, work-life balance, etc.
Thanks, Ashwin! I’m glad it was helpful and yes I think it’s a key step to redefine your success criteria beyond money! Thanks for sharing your thoughts. 🙂
We tend to do anything we can to protect our perceived identities. There are many ways to make these career/work/identity transitions from just jumping in to creating the stable floor you discuss above.
I used to think I had to leave my very stable and very identity focused profession in medicine. But, shockingly, that was *terrifying* to me. I’ve now been working barely part-time. It’s allowed me to redefine success as how many family dinners I make each week or how many days I write. It’s more a focus on enjoyment versus achievement, which is a radical shift for me.
Having the security of the part-time work has given me space to be human again and begin to explore other paths and possibilities.
But perhaps the most shocking aspect of part-time work is that I actually love being a physician again.
Thank you, Cobin! You’re bringing up so many valuable points — but the last one especially has been on my mind: we often do enjoy our work, just not when it’s pushed to the extreme, leaving no room for the other things that matter and ultimately turning it into a liability.
A part-time physician with the headspace to explore other things, a stable floor, and a broader definition of success - it really sounds like you’re living the article! 😉
Love the framing to internal security - I think the evidence of earning side income for the first time is powerful but sometimes those fears and voices still creep in. How do you remind yourself of your capabilities?
Yeah, I feel you. I reflect more about this in my piece on identity, if you’re curious.
One thing that’s really helped me is building my own kind of “hall of fame” - a place where I keep the best feedback I’ve received, my achievements, and a clear list of my strengths and capabilities. It’s something I come back to in moments of doubt to ground myself in what’s actually true. I also sometimes use AI as a coach just to talk through fears, get perspective, and not spiral alone.
The external security vs internal safety distinction is something I've been circling around in my own writing without ever naming it this cleanly...and you just did it in one sentence!! I've been exploring this from a slightly different angle: what happens when women lose the external structure of a career or a city all at once, and suddenly realise they've never been taught to build the internal version.
The scripts piece resonated so much.. especially this: Security scripts don't change because we decide they should. They change over time through awareness, small interruptions, and collecting new evidence. That's exactly the slower, messier, more honest version of how this actually works. Thank you for writing this with such precision. it's genuinely one of the clearest frameworks I've read on this topic
I loved your essay! You were able to put in words so many thoughts I had during my own transition journey, but could never elaborate on fully. The part on internal safety is amazing, and I now understand that this is what really makes a difference in the way we see ourselves in corporate or as entrepreneurs
Thank you so much, I’m really glad it helped! It was fascinating to look back at my own journey and see how my perspective shifted over time - especially while my husband had been thinking about it differently all along.
I absolutely loved this essay, I am going through this right at this very moment, but I keep telling myself there’s so many opportunities I can’t see and this forces me to trust myself which is perhaps one of the most important life skills!
Thank you, Maria! I’m glad if this essay helped you. I agree that often we don’t realize how many options and opportunities exist until we step outside the familiar. It can be scary, but also incredibly exciting to explore. 🙂
Extremely interesting article! I find surviving uncertainty extremely difficult - but it is so nice to read someone who already took the steps I want to take! Thank you Iwana :)
Great piece Iwana! Detaching your identity from corporate (especially in tech where emotional investment is expected) is from my experience one of the first (and not easy but) needed steps to think beyond false stability and security. I’m still in tech (by conscious choice) yet I have always had a portfolio of”small bets” on the side, sometimes more, sometimes less depending on my capacity. The danger is really to get too comfortable with the golden handcuffs and not carve out time to live a creative life full of different pieces of a puzzle.
Yeah, I think what you say is key. It's not about quitting today, but being aware of this, not getting too comfortable, questioning the status quo from time to time, and slowly building optionality on the side in whatever way your life allows right now.
This is brilliant Iwana, on so many levels.
The 'External security vs. internal safety' part is central I think. As you said, no matter how much money is in the bank, people always worry about money... or they don't.
Developing the internal safety side and believing in your core that no matter what, you'll be ok because of WHO you are (your identity, your abilities, your skills, etc) can be transformative.
Job security was something true for our parents... a few decades ago, having a job was actually safe in most countries. As you say, those days it means nothing. It's an old narrative we are holding on to... to feel safe I guess, and no freak out.
Money is such a "weird" thing also though. Ultimately who is right... the person putting money aside monthly to secure their future... sacrificing the now for a future not guaranteed... or the one enjoying life to the fullest now without thinking of tomorrow. There isn't a right answer I think.
Thank you, Jeremie! I agree and I find that reflection around saving/sacrificing versus fully enjoying the present really interesting.
For me, like with most things in life, it comes down to balance. Building for the future matters but so does actually living it now.
I tend to approach it like that as well… building for the future without sacrificing today. It’s not always easy though, there are many temptations out there.
I burned out 3 times during my 25 years of work in tech. I decided to quit in 2015 and never looked back. What also helped me is a frugal lifestyle. What I believed I needed was simply a societal conditioning, implanted desire, not an authentic need. We only need air, water, food, and shelter. Luxury cars, lots of travel, and mansions are not necessary for a fulfilling life, but of course, the social media says you do.
Yeah, totally agree! And everyone defines ‘luxury’ differently. I’d choose joyful work and peace of mind over excess luxury any day.
Loved this Iwana!
It’s true that we often think it’s irresponsible to ‘leave money on the table’ and often feel safety is the constant thriving for more.
I know I have more than enough, yet sometimes it doesn’t feel like it. I’m about to go travelling in the summer in the nordics in our van, and my aim by then is to feel the security internally - to know that I can enjoy 2 months of travel with 15 hours of week working, and know it’s enough. Enough to live, develop myself, and most importantly be present in a once in a lifetime opportunity.
Thank you for reminding us that safety is a choice we can find within ourselves 💙
Thank you, Fiona! You‘re so right that it’s a choice we can find within ourselves and something we can train to get better over time. So glad you guys are taking the time to travel in the summer - sounds amazing!!!
Agree and THANk YOU! 😊 we’re excited!
“Portfolio careers aren’t meant to be fixed. They’re meant to evolve throughout life. Components are added, paused, or dropped as your interests, capacity, and circumstances change.” YES YES YES!!! This is what makes life so exciting! We are constantly co-creating!
Haha, love the enthusiasm! I couldn’t agree more, when I learned about portfolio careers, I got so genuinely excited about it and all the possibilities it creates for living life on my own terms!
So many golden nuggets in here - you’ve reminded me I haven’t done my financial
Floor in a while. Really worth me checking in on that even while I’m in this portfolio journey, it’s not just set and forget it! And I definitely find little tiny acts outside work that build self trust are super helpful
To manage the “planting seeds” phase of starting new
Thanks Ella! Yeah it’s a continuous balance between covering the floor and planting the seeds as you said…🙂
Reframing security as an inside job is one of the key mindset shifts we need to make right now. Trusting ourselves - backing ourselves - to find our way through this disruption is such an important part of building new approaches to life and career.
Couldn't agree more, Jill, it's one of the key mindset shifts and it's a tough one!
This is such a helpful and informative article, Iwana - thanks for sharing, I'll be returning to it in future when I need a reminder!!
I’m glad to hear that! I wrote this as much for myself as a reminder for when the doubts inevitably creep in again. 😉
Great piece Iwana! Through some tough lessons I have had to learn that relying on the job market alone for security is not a good idea. Interests dont perfectly align. I’ve been introduced to the idea of a portfolio career through my time here on Substack, and the empowerment from being in charge of your own future is just different.
One key takeaway for me was pillar 4, diversifying your safety signal, to not just put money on a pedestal, ask yourself if youre happy with the hours, work-life balance, etc.
Thanks, Ashwin! I’m glad it was helpful and yes I think it’s a key step to redefine your success criteria beyond money! Thanks for sharing your thoughts. 🙂
Beautiful piece, Iwana!
We tend to do anything we can to protect our perceived identities. There are many ways to make these career/work/identity transitions from just jumping in to creating the stable floor you discuss above.
I used to think I had to leave my very stable and very identity focused profession in medicine. But, shockingly, that was *terrifying* to me. I’ve now been working barely part-time. It’s allowed me to redefine success as how many family dinners I make each week or how many days I write. It’s more a focus on enjoyment versus achievement, which is a radical shift for me.
Having the security of the part-time work has given me space to be human again and begin to explore other paths and possibilities.
But perhaps the most shocking aspect of part-time work is that I actually love being a physician again.
Thank you, Cobin! You’re bringing up so many valuable points — but the last one especially has been on my mind: we often do enjoy our work, just not when it’s pushed to the extreme, leaving no room for the other things that matter and ultimately turning it into a liability.
A part-time physician with the headspace to explore other things, a stable floor, and a broader definition of success - it really sounds like you’re living the article! 😉
Love the framing to internal security - I think the evidence of earning side income for the first time is powerful but sometimes those fears and voices still creep in. How do you remind yourself of your capabilities?
Yeah, I feel you. I reflect more about this in my piece on identity, if you’re curious.
One thing that’s really helped me is building my own kind of “hall of fame” - a place where I keep the best feedback I’ve received, my achievements, and a clear list of my strengths and capabilities. It’s something I come back to in moments of doubt to ground myself in what’s actually true. I also sometimes use AI as a coach just to talk through fears, get perspective, and not spiral alone.
The external security vs internal safety distinction is something I've been circling around in my own writing without ever naming it this cleanly...and you just did it in one sentence!! I've been exploring this from a slightly different angle: what happens when women lose the external structure of a career or a city all at once, and suddenly realise they've never been taught to build the internal version.
The scripts piece resonated so much.. especially this: Security scripts don't change because we decide they should. They change over time through awareness, small interruptions, and collecting new evidence. That's exactly the slower, messier, more honest version of how this actually works. Thank you for writing this with such precision. it's genuinely one of the clearest frameworks I've read on this topic
Thank you, Ann-Christin, appreciate it! The internal vs. external categorization was a game-changer for me to realize too! Glad it resonated.
I loved your essay! You were able to put in words so many thoughts I had during my own transition journey, but could never elaborate on fully. The part on internal safety is amazing, and I now understand that this is what really makes a difference in the way we see ourselves in corporate or as entrepreneurs
Thank you so much, I’m really glad it helped! It was fascinating to look back at my own journey and see how my perspective shifted over time - especially while my husband had been thinking about it differently all along.
I absolutely loved this essay, I am going through this right at this very moment, but I keep telling myself there’s so many opportunities I can’t see and this forces me to trust myself which is perhaps one of the most important life skills!
Thank you, Maria! I’m glad if this essay helped you. I agree that often we don’t realize how many options and opportunities exist until we step outside the familiar. It can be scary, but also incredibly exciting to explore. 🙂
Extremely interesting article! I find surviving uncertainty extremely difficult - but it is so nice to read someone who already took the steps I want to take! Thank you Iwana :)
Thank you Chiara! I agree it’s not easy and it’s a journey but it’s certainly manageable. 🙂💪🏻
Great series of articles!
Thank you so much for reading and letting me know! 🙂
You’re welcome. I’ve also subscribed. Tom