Most mainstream retirement content—books, blogs, financial advice, even lifestyle tips—is written by and for the middle class. These narratives often reflect middle-class anxieties: fear of running out of money, identity loss, the importance of staying “productive,” etc. As a result, retirement is framed as a cautious, defensive phase rather than a liberating one. Scarcity, not abundance, is the underlying tone. “Success” is still defined in terms of hustle, busyness, budgeting, or passive income hacks—not freedom, leisure, or optionality.
In contrast, the wealthy tend to retire very differently—often earlier, with more confidence, and on their own terms. But we rarely hear their stories because the truly wealthy don’t need to justify or explain their lifestyle.
Their lives are often private or intentionally under the radar.
When they do speak, it’s more likely through the lens of entrepreneurship, legacy building, or philanthropy—not “retirement.”
In a nutshell, much of the mainstream retirement narrative is limited as the microphone is held by those still living within a middle-class frame. That skews what “retirement” even means in the public imagination.
Thanks again, Jordan, for providing rich content outside the mainstream.
This is sort of a hidden benefit of self employment. Theres no upward smooth trajectory of income and therefore you have to get comfortable with spending more than you make sometimes. This helped me realize I had my own fears of spending I’ve decided to tango with
Yeah. I learned business spending first and then that helped with personal spending.
I’ve been thinking through this a lot because there aren’t really typical “budgeting” ways to internalize this. For the most part it takes a dance between the intuition and gut feel and the reality on paper via checkins.
Why does spending money have to correlate to living with purpose? Running shoes are cheap. Pushups are free. Curiosity is a mindset and information and knowledge are more accessible by 1000 fold than at any point in the past.
I’m not saying it’s unhealthy to spend - I just don’t automatically associate spending and living with purpose. No argument that it can help when used intentionally - but it is far from the first barrier.
Spending money can feel like pulling teeth for those of us who are extra frugal. I fall into that category and do question if I should reshape my spending habits sometimes. I go out of my way to be a penny pincher and sometimes that can backfire on me.
I'd like to comment on "Decumulation mindset." Almost universally in FIRE blogs and podcasts (and in conventional retirement forums as well), the fear of spending down a nest egg once retired is seen as a psychological flaw or error. But I think it conflates several things, at least a couple of which are rational, prudent behaviors missing from discussions:
1) Loss aversion bias: evolutionary psychology causes humans to fear loss more than value gain.
2) Familiarity bias: humans fear the unfamiliar, so for someone used to net savings, switching to net spending is unfamiliar, and thus scary. But this fades with time after being retired for a while.
3) A bizarre expectation that people who spent the bulk of their working lives living "below their means" (which was necessary to save and invest for retirement), and generally to avoid risk of overspending and uncontrolled debt, should suddenly switch to living precisely at their means once retired, throwing out the risk management aspect. This is what it means to retire as soon as you reach your FI number (whether you believe that is 25X or 33X your living expenses) rather than building a cushion beyond that, so you can typically spend below your Safe Withdrawal Rate (regardless of whether you believe it is 3%, 4%, or 5%). This is pervasive in FIRE social media, though much less so in conventional retirement planning spaces.
4) Not spending down a nest egg can be prudent risk management in general. Michael Kitces says: "The end result is that while in theory a retirement portfolio is meant to be spent, in practice most retirees faced with an ever-open-ended potential of living many more years will feel compelled to keep extra assets available, just in case… and never actually reach the point of depleting the retirement portfolio at all! Which, notably, isn’t a sign of inefficient portfolio spending or a consumption gap, but merely the prudent reality of dealing with an uncertain future!" (https://www.kitces.com/blog/consumption-gap-in-retirement-why-most-retirees-will-never-spend-down-their-portfolio/).
To me, it seems far more natural (and rational) to continue living below my means in retirement, just as I have during accumulation (not as much below, as saving for retirement is no longer required, of course). That should be a conscious choice, not a default to suddenly live at your means, and I view it as rational risk management, not a fear-based emotional response. And to put this in perspective, my pre-retirement professional expertise is in risk management.
In contrast, some loss aversion bias needs to be overcome to spend rationally in retirement, and familiarity bias will fade in time. But shifting to spending at your means from below your means should not be taken lightly or by default. It is a rational reason for a couple/few years of "one more year syndrome".
I’m going pay my parents to give me grandchildren. I don’t think my daughters are going to feel like they “didn’t earn it” when they can afford to have kids younger or stay home with them more.
Most mainstream retirement content—books, blogs, financial advice, even lifestyle tips—is written by and for the middle class. These narratives often reflect middle-class anxieties: fear of running out of money, identity loss, the importance of staying “productive,” etc. As a result, retirement is framed as a cautious, defensive phase rather than a liberating one. Scarcity, not abundance, is the underlying tone. “Success” is still defined in terms of hustle, busyness, budgeting, or passive income hacks—not freedom, leisure, or optionality.
In contrast, the wealthy tend to retire very differently—often earlier, with more confidence, and on their own terms. But we rarely hear their stories because the truly wealthy don’t need to justify or explain their lifestyle.
Their lives are often private or intentionally under the radar.
When they do speak, it’s more likely through the lens of entrepreneurship, legacy building, or philanthropy—not “retirement.”
In a nutshell, much of the mainstream retirement narrative is limited as the microphone is held by those still living within a middle-class frame. That skews what “retirement” even means in the public imagination.
Thanks again, Jordan, for providing rich content outside the mainstream.
Totally relate to your perspective, well said
This is sort of a hidden benefit of self employment. Theres no upward smooth trajectory of income and therefore you have to get comfortable with spending more than you make sometimes. This helped me realize I had my own fears of spending I’ve decided to tango with
I've found that owning your own business helps make more bold decisions in general by necessity. Spending probably is one of them.
Yeah. I learned business spending first and then that helped with personal spending.
I’ve been thinking through this a lot because there aren’t really typical “budgeting” ways to internalize this. For the most part it takes a dance between the intuition and gut feel and the reality on paper via checkins.
Very on point!
Why does spending money have to correlate to living with purpose? Running shoes are cheap. Pushups are free. Curiosity is a mindset and information and knowledge are more accessible by 1000 fold than at any point in the past.
I’m not saying it’s unhealthy to spend - I just don’t automatically associate spending and living with purpose. No argument that it can help when used intentionally - but it is far from the first barrier.
Spending money can feel like pulling teeth for those of us who are extra frugal. I fall into that category and do question if I should reshape my spending habits sometimes. I go out of my way to be a penny pincher and sometimes that can backfire on me.
Great piece!
I'd like to comment on "Decumulation mindset." Almost universally in FIRE blogs and podcasts (and in conventional retirement forums as well), the fear of spending down a nest egg once retired is seen as a psychological flaw or error. But I think it conflates several things, at least a couple of which are rational, prudent behaviors missing from discussions:
1) Loss aversion bias: evolutionary psychology causes humans to fear loss more than value gain.
2) Familiarity bias: humans fear the unfamiliar, so for someone used to net savings, switching to net spending is unfamiliar, and thus scary. But this fades with time after being retired for a while.
3) A bizarre expectation that people who spent the bulk of their working lives living "below their means" (which was necessary to save and invest for retirement), and generally to avoid risk of overspending and uncontrolled debt, should suddenly switch to living precisely at their means once retired, throwing out the risk management aspect. This is what it means to retire as soon as you reach your FI number (whether you believe that is 25X or 33X your living expenses) rather than building a cushion beyond that, so you can typically spend below your Safe Withdrawal Rate (regardless of whether you believe it is 3%, 4%, or 5%). This is pervasive in FIRE social media, though much less so in conventional retirement planning spaces.
4) Not spending down a nest egg can be prudent risk management in general. Michael Kitces says: "The end result is that while in theory a retirement portfolio is meant to be spent, in practice most retirees faced with an ever-open-ended potential of living many more years will feel compelled to keep extra assets available, just in case… and never actually reach the point of depleting the retirement portfolio at all! Which, notably, isn’t a sign of inefficient portfolio spending or a consumption gap, but merely the prudent reality of dealing with an uncertain future!" (https://www.kitces.com/blog/consumption-gap-in-retirement-why-most-retirees-will-never-spend-down-their-portfolio/).
To me, it seems far more natural (and rational) to continue living below my means in retirement, just as I have during accumulation (not as much below, as saving for retirement is no longer required, of course). That should be a conscious choice, not a default to suddenly live at your means, and I view it as rational risk management, not a fear-based emotional response. And to put this in perspective, my pre-retirement professional expertise is in risk management.
In contrast, some loss aversion bias needs to be overcome to spend rationally in retirement, and familiarity bias will fade in time. But shifting to spending at your means from below your means should not be taken lightly or by default. It is a rational reason for a couple/few years of "one more year syndrome".
And those kids end up not enjoying it anyway because they didn't earn it.
I’m going pay my parents to give me grandchildren. I don’t think my daughters are going to feel like they “didn’t earn it” when they can afford to have kids younger or stay home with them more.