Retirement Series #5: Retire Or Get Retired
A Perspective on Intentional Retirement
Executive Summary
For most of human history, work ended only when the body failed, the land was lost, or the household collapsed. Choice was a luxury afforded to almost no one.
Today, for the first time at scale, retirement can be intentional, not merely endured. Optionality is not just a financial outcome; it is a generational gift. One that can be squandered quietly, or received deliberately.
“Retire or get retired” should be viewed as an invitation: to recognize that we live in a narrow window of history where time, capital, and longevity can be aligned, if we act before momentum fades.
The Idea, Reconsidered
Retirement has long been framed as an ending. Less obvious is that retirement is a handoff → from necessity to discretion.
To “get retired” is not a failure of character. It is what has happened to nearly everyone who came before us. When strength faded, when clients moved on, when skills and relevance shifted, work simply stopped. Life adjusted seemingly downward.
What is new is the possibility of stepping aside while capacity remains, with health intact, curiosity alive, and choice abundant.
This is not about escape from work. It is about retaining authorship in a framework of intentional optionality.
Optionality as a Gift
When one considers optionality, it is often described clinically: liquidity, flexibility, diversification. But its true nature is more humane.
Retirement optionality is waking without urgency. It is saying no without apology. It is choosing patience in a world addicted to speed. It allows work to become expression rather than obligation.
This condition, where survival no longer dictates every decision, has appeared before only briefly, and only for elites. We now treat it as ordinary, even though it is anything but.
What Preserves the Gift
We’ve seen how starting early in planning for retirement and creating a retirement narrative serve as foundational building blocks to retiring (or Pre-tiring) on one’s own terms.
Ironically, the option to retire on one’s own terms survives less through brilliance, and more through restraint.
It is preserved when fixed costs are kept modest enough that life can bend without breaking. When ambition does not harden into permanence. When spending remains adjustable, and dignity is not driven by keeping up appearances.
It endures when income arrives quietly, without requiring performance or permission. When liquidity is held not as fear, but as time stored in a usable form.
Optionality strengthens when plans acknowledge volatility without trying to outsmart it; when early years are treated gently, and resilience is valued over precision.
And it deepens when skills are kept warm, not because they must be used, but because they could be. The knowledge that one can re-engage changes how risk feels.
Why This Moment Is Different
Intentional retirement and the optionality it affords comes with a growing list of never befores:
Never before have people lived this long with this much accumulated surplus and this degree of personal autonomy.
Never before has identity been so decoupled from station.
Never before has learning been so accessible, nor work so modular.
Never before has it been possible to step back without vanishing.
This is not just a financial shift. It is a civilizational anomaly. But anomalies close. Careers narrow. Bodies change. Systems optimize.
Options rarely disappear dramatically. They decay invisibly and by slow neglect. The tragedy is not losing choice. It is failing to notice that one had it.
A More Generous Ending
To retire intentionally is not to withdraw from life. It is to receive the gift fully.
It is to look at one’s circumstances - financial, physical, relational - and say: I will not wait until choice decays before placing a value on it.
It is to design life so that work can continue, but never at gunpoint. So that time can stretch, wander, or concentrate, at will. So that the later chapters are not merely longer, but lighter.
A Final Invitation
Do not ask whether you are ready to retire. Ask whether you are ready to protect the ability to choose.
Audit your fixed costs.
Measure your time “runway.”
Build liquidity before optimization.
Preserve and develop skills, not just assets.
Engineer flexibility, now, while no one is forcing you to.
If you live in this age - this strange, abundant sliver of history - then optionality is already within reach. Not guaranteed. Not permanent. But possible.
That alone makes this moment extraordinary. Treat it accordingly.
Up Next:
Sunday - The Plight of Desperation Capitalism
This publication is for brains, not bets. The Other Side of Obvious shares ideas, stories, and general financial information - not personalized investment, tax, or legal advice. Investing comes with risk (including losing money). Talk to a pro before you act. Please take time to read these important disclosures before you get started.