What would your eighty-year-old self tell you today?

A forty-five-year-old man is considering an excellent job offer: more money, more status, more opportunity - but also less home, less time with the children and more travel.

His father, nearly eighty, asks only one question: how old are the children? Then he says: money can sometimes be earned again. Promotions can come later. But a six-year-old child will be six only once.

“Ask your father and he will tell you, your elders and they will say to you” (Deuteronomy 32:7). Sometimes an older person does not give us new information. He gives us proportions that time has taught him.

Some things have no column in a spreadsheet: an hour with a parent, a Shabbat with a child, a prayer said with attention. The things hardest to measure can become the things we later discover were most valuable.

Before a major decision, ask a non-financial question: what would the eighty-year-old version of me beg me not to waste today?

Borrow a little of that later perspective now.

If you looked back at today thirty years from now, what would you beg yourself not to postpone?

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A forty-five-year-old man spent months debating whether to accept a new job offer. Financially it was an excellent offer, with a much higher salary and a more prestigious position, but it had a price: frequent travel abroad, very long hours, and less time at home. He did what we usually do when we are undecided. He opened a table, wrote down pros and cons, calculated money, promotion possibilities, pension, professional status, and risks. After weeks of thinking he still could not decide.

One day he went to visit his elderly father, who was already close to eighty. The son told him about the dilemma and presented all the numbers. The father listened and asked, “How old are your children?” He answered, “Twelve, nine, and six.” The father was silent for a moment and said, “I cannot tell you which job to take. But I can tell you something you are still too young to know. Money you lose can sometimes be earned later. A promotion you did not get may come a few years from now. But a six-year-old child will be six only once.”

The son returned home with the same job offer and the same numbers, but it was no longer the same dilemma. His father had not given him any new information about the workplace. He had given him something else: a view of life from farther away.

There are things one sees at eighty that are difficult to see at forty.

Not because an eighty-year-old is necessarily wiser about every subject, and not because every older person is always right. But because time changes proportions. Things that once looked enormous shrink. Things pushed aside reveal themselves as precious. A person has already seen successes that were forgotten, quarrels that turned out to be unnecessary, children who grew up too quickly, opportunities that did not return, and people he was certain would always be here.

In the Song of Haazinu, Moses says: “Remember the days of old, understand the years of generation after generation; ask your father and he will tell you, your elders and they will say to you” (Deuteronomy 32:7).

Why must one ask the elders?

Rashi explains the verse in the context of history and God’s conduct with the generations: “Ask your father - these are the prophets who were called fathers... your elders - these are the sages” (Deuteronomy 32:7). Moses tells Israel: do not try to understand all of reality from the tiny moment in which you presently stand. There is a past. There are generations. There are people who can see things from a wider perspective.

But perhaps there is also a great lesson here for teshuvah. Most decisions we later regret are not made because we want to destroy our lives. They are made because, at the moment of decision, something small looks very large and something truly large looks very far away.

In a moment of anger, the need to answer now feels enormous, while the price that one sentence will exact an hour later seems distant. In a moment of temptation, the pleasure of this minute feels tangible, while tomorrow’s regret is not yet felt. When a person is immersed in work, the task on the desk feels terribly urgent, while the child growing beside him looks as though he will remain a child for many years. When one’s honor is hurt, the need to prove oneself right feels critical, while the possibility that ten years from now one will regret the relationship that was destroyed hardly enters the calculation.

Perhaps part of wisdom is learning to bring into the room the person I will be in the future.

Imagine that you are eighty-five. Thank God, your mind is clear. You sit in an armchair and look back over your life. The children are grown. Perhaps there are grandchildren and great-grandchildren. Your career is behind you. Many of the things that troubled you at fifty no longer exist. Then you are given the chance to return for one hour to your life today.

Not for an entire year.

For one hour.

Where would you go?

Would you ask to enter the office again to finish a few more messages?

Would you want to return to that argument in order to win it?

Would you ask for another hour in front of a screen?

Or perhaps would you run to the house where the children are still small, sit beside them, and be in no hurry to go anywhere?

Perhaps you would want one more Shacharit when the body is still strong and you can stand without pain.

Perhaps you would want one more Shabbat at the table with your parents.

Perhaps you would want to open a Gemara again while your eyes still see clearly and your mind is still sharp.

This question is not meant to make us sad. It is meant to restore proportion to what we possess now.

Because the tragedy is not only losing something precious. Sometimes the tragedy is holding something precious in your hand for years and understanding its value only after it is no longer in your hand.

Moses says: “Ask your father and he will tell you, your elders and they will say to you.” There is wisdom a person can receive before paying for it through personal experience. A wise person does not have to make every mistake himself in order to learn from it. He can listen to someone who has already traveled the road.

The Mishnah in Pirkei Avot says: “Who is wise? One who learns from every person” (Avot 4:1). This is a fascinating definition. Wisdom is not only how many answers I have, but how capable I am of learning even from lives that are not my own.

A younger person can sit beside an older person and hear from him what truly remains after fifty years of marriage. A son can ask his father what he would do differently if he could return to his age. A student can ask an older rabbi which things in serving God became clear over the years as essential and which turned out to be noise.

But there is a reason we almost never ask these questions.

We are busy asking people how to succeed, and much less busy asking them what not to regret.

We ask a successful person how he built a business, bought a house, and advanced. Perhaps sometimes it would be worthwhile to ask an eighty-year-old a different set of questions: what are you glad you gave time to? What do you regret spending years on? Which quarrel was unnecessary? Which fear turned out to mean nothing? What do you wish you had understood twenty years earlier?

Those are Shabbat Shuvah questions.

Because teshuvah is not only looking backward at what I did. Teshuvah is also an attempt to prevent the confession of the future.

There are confessions we say on Yom Kippur about the year that passed, and there are confessions that, if we are wise enough, perhaps we will not need to say twenty years from now.

I regret that I was not present enough with my children.

I regret that I spent so many years angry with my brother.

I regret that I was so occupied with what people thought about me.

I regret that I postponed learning until a time when I would have more leisure.

I regret that I did not say thank you while there was still someone to hear it.

The question is whether we must reach eighty in order to know these things.

King Solomon says: “It is better to go to a house of mourning than to go to a house of feasting, for that is the end of every person, and the living will take it to heart” (Ecclesiastes 7:2). The verse does not ask a person to live in sadness. It says that an encounter with the finiteness of life can teach the living how to live.

“And the living will take it to heart.”

Not the dead.

The living.

The purpose of thinking about the end is not to become preoccupied with death. The purpose is to make better decisions in life.

And perhaps this is something we need especially during the Ten Days of Repentance. We say “Remember us for life,” but in order to ask for life honestly, sometimes we must remember that life is not infinite.

Not in order to be afraid.

In order to choose.

If we had infinitely many Shabbatot, this Shabbat would have no special significance. If children stayed small forever, we could always speak with them tomorrow. If parents lived forever, the phone call could wait. If we had infinitely many Yom Kippurs, we could do teshuvah next year.

But precisely because time is limited, choice becomes meaningful.

Maimonides writes: “A person should always see himself as though he is inclined toward death, for perhaps he will die at that hour and be found standing in his sin; therefore he should repent of his sins immediately” (Mishneh Torah, Hilkhot Teshuvah 7:2). Maimonides does not say this in order to paralyze a person with fear, but to break one of our greatest illusions: the word “later.”

Later I will repair.

Later I will ask forgiveness.

Later I will learn.

Later I will invest in my home.

Later I will pray properly.

But “later” is not time we were given. The only time in our hands is now.

So I want to suggest a very different kind of self-examination for this Shabbat. Instead of asking only, “What did I do this year?” sit for a few minutes and write a letter from your eighty-five-year-old self to the person you are today.

What would he say to you?

What would he ask you to stop wasting energy on?

With whom would he ask you to make peace?

Whom would he tell you to call?

What would he tell you to stop postponing?

What would he say about the children?

What would he say about your Torah?

What would he say about all the time you invest in things you do not truly want to carry into the story of your life?

This could be the strongest mussar conversation, because no one is preaching to me.

I am simply trying to look at my day from the other end of life.

Then we may discover something surprising. Many of the things that pressure us today will barely appear there. We will not remember most of the messages we answered. We will not remember who cut us off, who did not show us enough respect, or who won some small argument.

But we will remember people.

We will remember moments.

We will remember whether we were there when they needed us.

We will remember what we built.

We will remember whether there was Torah in the home.

We will remember whether the children felt they could speak with us.

We will remember whether we knew how to ask forgiveness.

We will remember whether we lived only in order to get things done, or whether we also managed to live.

And perhaps we can hear a new meaning in the words “Ask your father and he will tell you, your elders and they will say to you.” Do not wait to become old in order to acquire the proportions of old age. Ask now.

There are things an older person can give you that cannot be transferred as a financial inheritance. He can give you perspective.

He can tell you: the thing you think will collapse if you do not deal with it today may not matter at all five years from now. And the person to whom you say today, “I don’t have time,” may be the person from whom, thirty years from now, you would most want one more hour.

Shabbat Shuvah is not only a Shabbat on which we ask how to repair what was.

It is a Shabbat on which we can save ourselves from a regret that has not yet been born.

So before Yom Kippur I would like each person to take one decision and pass it through a simple test: when I am eighty-five and look back at this moment, will I be glad that I chose this way?

Not every decision in life can be solved by this test. There are complex questions and many considerations. But this test can quickly expose several things that deep down we already know and that the noise of the present is hiding.

The elderly father at the beginning did not tell his son which job to choose. He only reminded him of something his spreadsheet did not know how to calculate: a six-year-old child will be six only once.

Some things do not have a column in Excel.

You cannot calculate longing.

You cannot calculate an hour with your father.

You cannot calculate a Shabbat with a child.

You cannot calculate one prayer said with full presence.

But as life moves forward, we sometimes discover that the things we could not calculate were worth more than everything else.

Moses stands at the end of his life. He can already see the land he will not enter. And precisely from that place he tells us: “Ask your father and he will tell you, your elders and they will say to you.”

Do not wait until the end of the road to understand what mattered on the road.

Borrow now a little of the perspective of the person you will be at its end.

And ask him one question:

If you could return to this day for only one hour, what would you beg me not to waste?

And after you hear the answer, do not save it for age eighty.

Live it now.