In what ways, if any, would knowing the date of your death help you plan your life? How many more years do you honestly believe you have left?

Last week’s question about whether we’d open an envelope containing our death date sparked something I wasn’t expecting. The responses poured in—thoughtful, conflicted, passionate arguments on both sides. Some readers accused me of cowardice for refusing to look. Others thanked me for articulating their own instinctive revulsion at the idea. But the question that kept surfacing in the comments was this: okay, but what if you did know? What then?

This week’s follow-up from Gregory Stock’s The Book of Questions forces us past the initial decision and into murkier territory. It’s one thing to declare you wouldn’t want to know when you’ll die. It’s another thing entirely to examine what that knowledge might actually change about how you live. The question assumes knowledge we’ve already established might be toxic, then asks us to consider whether that toxicity might serve a purpose.

It’s a masterful bit of psychological misdirection. Just when you’ve convinced yourself that ignorance is bliss, Stock pulls the rug out and asks you to consider whether that same ignorance might also be… wasteful.

The Seductive Logic of Death-Driven Planning

There’s an undeniable appeal to the idea that knowing your expiration date would clarify your priorities. In our culture of endless options and competing demands, the death envelope represents the ultimate constraint—and constraints, as any creative person will tell you, can be liberating. With a finite timeline clearly established, all those agonizing decisions about how to spend your time would suddenly become manageable. Should you stay in that soul-crushing but well-paying job? Well, how much time do you have left? Is it worth spending a third of your remaining days miserable for the sake of security you might not live to enjoy?

The logic feels bulletproof: perfect information about your most important deadline would enable perfect decision-making about everything else. No more wondering whether to save money for a retirement that might never come. No more debating whether it’s worth learning a new skill that takes years to master. No more hesitating about telling people how you really feel because there might be a better time later.

From this perspective, those of us who would leave the envelope sealed aren’t just choosing ignorance—we’re choosing inefficiency. We’re opting to stumble through life making suboptimal choices based on incomplete information when we could be living with surgical precision, making every day count because we know exactly how many days we have to work with.

It’s a compelling argument, and I understand why some readers found my refusal to open the envelope frustrating. What’s the point of having access to the ultimate life hack if you’re too squeamish to use it?

The Planning Paradox

But here’s where the fantasy starts to break down: I’m not convinced that knowing my death date would actually change much about how I live my life. And this realization is more unsettling than I expected.

If I knew I had exactly ten years left, what would I do differently? The honest answer is: probably not much. I’d still go to work—I’d need the money and the health insurance, and besides, I actually find my work meaningful. I’d still spend my evenings writing, reading, watching movies, building Lego sets. I’d still struggle with the same lifestyle changes I know I should make: eating better, exercising more, taking better care of my aging body.

This is either deeply reassuring or deeply depressing, depending on how you look at it. On one hand, it suggests that I’m already living according to my values, that I don’t need the specter of imminent death to motivate me to pursue what matters. On the other hand, it raises uncomfortable questions about whether what I consider “what matters” is actually just comfortable routine disguised as meaningful choice.

The planning paradox is this: the people who would benefit most from knowing their death date—those who are currently wasting their lives on trivial pursuits or trapped in situations that don’t serve them—are probably the least likely to use that information effectively. Meanwhile, those who are already living intentionally might find that the knowledge doesn’t change their behavior so much as it changes their experience of that behavior, transforming peaceful contentment into anxious calculation.

This isn’t to say the knowledge would be useless. There are certainly scenarios where a known expiration date would clarify difficult decisions. If you knew you had only two years left, you probably wouldn’t waste time on a four-year degree program. You might be more willing to take financial risks, less concerned with building long-term wealth, more focused on immediate experiences rather than future security.

But these are edge cases, extreme scenarios where the death date is uncomfortably close. For most of us, most of the time, the knowledge might be less transformative than we imagine.

The Uncomfortable Arithmetic of Remaining Time

The second part of this week’s question forces an even more uncomfortable reckoning: how many years do you honestly believe you have left? It’s one thing to philosophize about hypothetical envelopes. It’s another to do the math on your own mortality.

I’m in my forties, which means I’m probably closer to the end than to the beginning, though exactly how close is anyone’s guess. I’m not in great shape—my back aches, my knees complain, I carry more weight than I should. But I’m not in poor health either. I don’t smoke, I don’t drink heavily, I have access to decent healthcare. If I had to guess, I’d say I probably have somewhere between twenty and thirty years left, assuming I don’t make any dramatic changes to how I take care of myself.

But here’s what’s interesting: even without knowing my exact expiration date, I have a rough sense of my timeline, and it’s not motivating me the way the death-driven planning advocates would predict. I know I should eat better. I know I should exercise more. I know that making these changes now could add years to my life and life to my years. And yet… I don’t.

This isn’t because I’m lazy or indifferent to my health. It’s because behavior change is hard, and it gets harder as you age. The feedback loops that motivated me in my twenties—seeing rapid results from diet and exercise changes—no longer work the same way. My body responds more slowly, recovers more grudgingly, protests more loudly when I ask it to do things it’s not used to doing.

So even with a reasonable estimate of my remaining time, even with clear knowledge of what I could do to extend it, I find myself stuck in patterns that aren’t serving my long-term interests. Would having an exact death date change this? I doubt it. If anything, it might make the problem worse, adding temporal anxiety to all the other barriers that already make healthy changes difficult.

The Myth of Death-Bed Clarity

There’s a persistent cultural myth that proximity to death brings clarity, that people become suddenly wise and purposeful when they know their time is running out. We tell stories about terminal diagnoses that inspire radical life changes, about people who discover what really matters only when faced with imminent loss.

But this narrative might be more comforting than accurate. The reality is that people facing death often struggle with the same psychological patterns that governed their lives when they thought they had unlimited time. Depression, anxiety, denial, and poor decision-making don’t magically disappear when the timeline becomes clear. If anything, they might become more intense under the pressure of a ticking clock.

Consider how most people handle ordinary deadlines. Do we become models of efficiency and focus when we know exactly when a project is due? Sometimes, but more often we procrastinate, panic, or rush through important decisions. Why would the ultimate deadline be different?

The death envelope fantasy assumes we would respond to perfect temporal information with perfect rationality, but this ignores everything we know about human psychology under stress. Knowledge of our death date might be just as likely to paralyze us with choice overload or drive us to make impulsive decisions we’d later regret—if we lived long enough to regret them.

The Value of Imperfect Information

What strikes me most about wrestling with these questions is how much they reveal about the limitations of information itself. We live in a culture that treats knowledge as inherently valuable, that assumes more data always leads to better decisions. But the death envelope scenario suggests there might be optimal levels of uncertainty, sweet spots where we have enough information to make reasonable plans but not so much that we become paralyzed by the weight of perfect knowledge.

Most of us already live with rough estimates of our remaining time. We know we’re not immortal. We have some sense of our health status, our family history, the statistical likelihood of various outcomes. This imperfect information might actually be more useful than perfect information because it allows for hope, adaptability, and the kind of long-term thinking that makes civilization possible.

With a known death date, would I be able to plant a garden whose maturity I might not see? Would I be willing to start projects that might not pay off within my lifetime? Would I be capable of the temporal generosity that allows us to invest in things that outlast us?

These questions matter because much of what makes life meaningful depends on our ability to act as if we have more time than we might actually have. The parent who saves for a child’s education, the scientist who starts experiments that will take decades to complete, the writer who begins a novel knowing it might not be finished—all of these acts require a kind of productive ignorance about our personal timelines.

Living Backward from an Unknown End

Perhaps the real insight here isn’t about what we’d do differently if we knew our death date, but about what we can do differently with the information we already have. We don’t need perfect temporal knowledge to recognize that our time is limited, that our choices matter, that delay and procrastination come with real costs.

The uncomfortable truth is that most of us already know what we should be doing differently. We know we should exercise more, eat better, spend more time with people we love, pursue work that feels meaningful, take reasonable risks in service of meaningful goals. The problem isn’t lack of information—it’s the gap between knowing and doing, between intention and action.

This gap wouldn’t magically close if we knew our exact expiration date. If anything, it might widen under the pressure of perfect temporal awareness. The person who can’t motivate themselves to exercise when they have an unknown amount of time left probably won’t suddenly develop discipline when that time becomes precisely quantified.

What might work better is learning to live backward from an unknown end—to make choices based on our values and priorities rather than our temporal calculations. This means accepting that we’ll never have perfect information about how much time we have left, but we can still make reasonable guesses about what we want that time to contain.

For me, this exercise has been clarifying in unexpected ways. Thinking about what I’d do if I knew my death date has helped me recognize that I’m already mostly living according to my actual priorities, not just my stated ones. I say I value health and fitness, but my behavior reveals that I value comfort and routine more. I say I want to make the most of my remaining time, but I define “making the most” as continuing to do work I find meaningful and spending my free time on activities I genuinely enjoy.

This isn’t necessarily admirable or optimal, but it’s honest. And perhaps honesty about our actual priorities is more valuable than fantasy about our optimal ones.

The Courage of Ordinary Time

In the end, both versions of the death envelope question—whether we’d look and what we’d do if we knew—point toward the same fundamental challenge: learning to live fully within uncertainty. This doesn’t mean being passive or indifferent to the future. It means recognizing that perfect information isn’t necessary for meaningful choice, that uncertainty can be productive rather than paralyzing, that ordinary days lived according to our actual values might be more precious than extraordinary days lived in service of temporal anxiety.

The person who exercises because they enjoy it, not because they’re calculating its effect on their lifespan, might be healthier in the long run than the person who’s constantly monitoring their biological clock. The person who pursues work they find meaningful, regardless of how much time they have left to do it, might contribute more than the person who’s constantly recalibrating their goals based on temporal spreadsheets.

My envelope can stay sealed, and my timeline can remain comfortably vague. I’d rather spend my unknown number of remaining days doing things that feel worthwhile for their own sake rather than because they optimize my remaining time allocation. There’s something beautifully stubborn about choosing to live according to your values rather than your deadlines, about finding meaning in the doing rather than the duration.

After all, if the goal is to make the most of whatever time we have left, maybe the best strategy is to stop calculating and start living.

What about you? How do you think knowing your death date would change your planning? And how many years do you honestly believe you have left? Share your thoughts in the comments—I’m fascinated to hear how others navigate the intersection of mortality and meaning.