I know what you mean about missing the paycheck. It’s not so much the money, it’s that validation. But here you are and I enjoyed your article. If I could give you a gold star, I would. I will give you a virtual one instead. ⭐️
This entire conversation is so layered. The balance between preparing and just "living." The burden of responsibility to provide for the future versus the joy and expansion that comes from travel and new experiences. You have left me noticing that we are (in the US) living in a world that has leaned so far away from community and sharing—"the village." I so appreciate your concise and vulnerable sharing here, sparking others to deeply consider life beyond the paycheck.
love the word " Freedom Fund I am in the same boat as you .It can be difficult to switch from saving for life to actually living it. Many of us spend decades learning discipline but almost no time learning permission. I love the idea that money was never the destination. It was simply the tool that made freedom possible. That feels like one of the hardest lessons of retirement.
"Money was never the destination. It was simply the tool that made freedom possible."
Yes — exactly that. And the permission to actually use it after decades of building it turns out to be its own whole lesson. So glad this one resonated.
The Freedom Fund idea is brilliant because it turns permission into structure. Not reckless spending. Not "treat yourself" as a personality disorder... Though I can't help but hear Parks & Rec here... "Treat Yo'Self!!" hahaha
This is such an important conversation. To give permission to accepting rather than giving. The change of identity is a huge shift. I could have taken the plunge this year and quite the day job but I'm finding the loss of structure and identity a bit much. Lots of other changes happening right now means trying to take one change at a time inatead of tossing everything out at once. Its nice to have the luxury of time and choice in the process.
One change at a time is its own kind of courage, even when it doesn't look as dramatic as the leap. Rooting for you as you find the pace that's actually yours.
I can so relate to this — the arrows are forever pointing in directions that don't always align with where you thought they would!
I was discussing retirement plans with my husband — and in the course of a few weeks we went from downsizing, to buying a travel trailer, to looking at property in the Appalachians. Literally, arrows pointing east, west, north, and south!
Arrows pointing every direction is such a good way to put it. We've had our own version — one conversation it's "stay put and simplify," the next it's "sell everything and go."
I don't think the arrows ever fully settle. I think you just get better at living inside the uncertainty instead of waiting for it to resolve.
This resonated far beyond finances. It feels as though you're describing the challenge of receiving after a lifetime of building. So many of us become fluent in sacrifice and preparation, only to discover that enjoying what we've carefully created requires a different kind of courage altogether. Beautifully written. X
That's a good way to put it — receiving takes its own kind of courage, not just the sacrifice. There was luck in it too. We don't take any of it for granted.
This is why I refuse to spend 30 years wiring my brain only to watch a number go up, just to face the psychological crisis of learning how to bleed it back down later.
Instead of waiting for retirement to build a "Freedom Fund" from scratch, I manage my capital like a CFO right now, ordering every dollar to work hard today.
As an entrepreneurial investor, I use a barbell strategy pairing a high-yield covered ETF like PAYG for immediate monthly cash flow with VT for long-term global growth.
I use that cash flow here and now to actively design my life and eliminate friction, while the rest automatically compounds for the future.
It’s not about waiting to retire; it's about being the CEO of your own life today. 💼🚀
That's the harder version of the same lesson — it shouldn't take a health scare to give ourselves permission. I'm glad you got there, even if the path to it wasn't fair.
When I retired from my professional dance career a few years ago, I was surprised (and still am, really) by how much it bothers me to not be markedly contributing financially. Even though I received an inheritance from my mom that greatly impacts our overall financial situation, I do not like the feeling of not contributing a regular paycheck to our coffers. It has surprised me because although I have many friends who were stay at home moms and I never thought any less of their choices, I am not wholly comfortable in that role myself. I am very lucky to be earning a little bit of money from my writing, but the lack of a steady paycheck has been an adjustment. All that being said, I have never been happier, more creatively alive, or more fully present in my life. Thanks for sharing and for triggering this self reflection.
I know what you mean about missing the paycheck. It’s not so much the money, it’s that validation. But here you are and I enjoyed your article. If I could give you a gold star, I would. I will give you a virtual one instead. ⭐️
Thank you for the star. Seems like even without the paycheck validation, having people like you send a note is even more priceless.
I feel like I’ve joined such a warm space filled with fascinating people here in Substack. It is a joy to meet you.
This entire conversation is so layered. The balance between preparing and just "living." The burden of responsibility to provide for the future versus the joy and expansion that comes from travel and new experiences. You have left me noticing that we are (in the US) living in a world that has leaned so far away from community and sharing—"the village." I so appreciate your concise and vulnerable sharing here, sparking others to deeply consider life beyond the paycheck.
love the word " Freedom Fund I am in the same boat as you .It can be difficult to switch from saving for life to actually living it. Many of us spend decades learning discipline but almost no time learning permission. I love the idea that money was never the destination. It was simply the tool that made freedom possible. That feels like one of the hardest lessons of retirement.
"Money was never the destination. It was simply the tool that made freedom possible."
Yes — exactly that. And the permission to actually use it after decades of building it turns out to be its own whole lesson. So glad this one resonated.
The Freedom Fund idea is brilliant because it turns permission into structure. Not reckless spending. Not "treat yourself" as a personality disorder... Though I can't help but hear Parks & Rec here... "Treat Yo'Self!!" hahaha
Treat Yo'Self, if Tom Haverford kept a spreadsheet. That tracks.
This is such an important conversation. To give permission to accepting rather than giving. The change of identity is a huge shift. I could have taken the plunge this year and quite the day job but I'm finding the loss of structure and identity a bit much. Lots of other changes happening right now means trying to take one change at a time inatead of tossing everything out at once. Its nice to have the luxury of time and choice in the process.
One change at a time is its own kind of courage, even when it doesn't look as dramatic as the leap. Rooting for you as you find the pace that's actually yours.
I can so relate to this — the arrows are forever pointing in directions that don't always align with where you thought they would!
I was discussing retirement plans with my husband — and in the course of a few weeks we went from downsizing, to buying a travel trailer, to looking at property in the Appalachians. Literally, arrows pointing east, west, north, and south!
Arrows pointing every direction is such a good way to put it. We've had our own version — one conversation it's "stay put and simplify," the next it's "sell everything and go."
I don't think the arrows ever fully settle. I think you just get better at living inside the uncertainty instead of waiting for it to resolve.
What did you decide?
Wow, I loved this. Thank you so much for sharing!
So glad it landed with you — thank you for reading.
This resonated far beyond finances. It feels as though you're describing the challenge of receiving after a lifetime of building. So many of us become fluent in sacrifice and preparation, only to discover that enjoying what we've carefully created requires a different kind of courage altogether. Beautifully written. X
That's a good way to put it — receiving takes its own kind of courage, not just the sacrifice. There was luck in it too. We don't take any of it for granted.
This is why I refuse to spend 30 years wiring my brain only to watch a number go up, just to face the psychological crisis of learning how to bleed it back down later.
Instead of waiting for retirement to build a "Freedom Fund" from scratch, I manage my capital like a CFO right now, ordering every dollar to work hard today.
As an entrepreneurial investor, I use a barbell strategy pairing a high-yield covered ETF like PAYG for immediate monthly cash flow with VT for long-term global growth.
I use that cash flow here and now to actively design my life and eliminate friction, while the rest automatically compounds for the future.
It’s not about waiting to retire; it's about being the CEO of your own life today. 💼🚀
When I retired I thought I had given myself permission to spend but it wasn’t until a major health issue that I committed fully to it.
That's the harder version of the same lesson — it shouldn't take a health scare to give ourselves permission. I'm glad you got there, even if the path to it wasn't fair.
Thank you.
When I retired from my professional dance career a few years ago, I was surprised (and still am, really) by how much it bothers me to not be markedly contributing financially. Even though I received an inheritance from my mom that greatly impacts our overall financial situation, I do not like the feeling of not contributing a regular paycheck to our coffers. It has surprised me because although I have many friends who were stay at home moms and I never thought any less of their choices, I am not wholly comfortable in that role myself. I am very lucky to be earning a little bit of money from my writing, but the lack of a steady paycheck has been an adjustment. All that being said, I have never been happier, more creatively alive, or more fully present in my life. Thanks for sharing and for triggering this self reflection.
The paycheck thing is its own grief, separate from the money. I think we attached more identity to the contribution than we knew.
I think you are correct!