Rabbi Eliezer would say, “Repent one day before your death." (Ethics of the Fathers 2:10) Asked his disciples, “Does a man know on which day he will die?” Said he to them, “So being the case, he should repent today, for perhaps tomorrow he will die; hence, all his days are passed in a state of repentance.”



Hey, everyone. It’s my birthday today. I’m 120 years old! And today is the last day of my life. Thus begins the Torah portion Vayeilech, which chronicles Moses’s farewell to the Jewish people, in which he gives his final words of instruction and comfort, and passes the baton of leadership to Joshua.

Unlike Moses, however, most of us don’t know the actual day of our death. Proponents of mindfulness exhort us, however, to imagine that it was, with positive clichés—as if urging us to live each day as if it were our last would somehow cure our existential procrastination. But that doesn’t work for me. Last day, huh? OK, I think I’ll have the nachos grande (with sour cream, of course), an order of mozzarella sticks and a pineapple mojito. Veggie burger on a lettuce wrap? Don’t think so.

In other words, “Seize the day!” doesn’t necessarily lead me to the right place.

Fast-Forwarding Your Life

Instead of pretending that today were the last day of your life, what if you were to realize, instead, that it’s the first day of the rest of your life? What if you could make use of a preferred future to inspire and focus your present behavior? What if you could hold a vision of a realized potential and chart a path towards that goal? How great would it be to age with vitality and quality of life, and still show up for flamenco classes at age 75? Hmm, that veggie burger sounds pretty good after all.

I had a client who was struggling with “doing the right thing.” Knowing how important this man’s relationship was with his son and how he wanted to be a good role model as a dad, I asked him a classic coaching question: “What would you want your son to say about you at your 80th birthday party?” As a technique for shaping present behavior, I think fast-forwarding 20, 30 or more years ... even to an imagined deathbed, is a powerful exercise. When an upset intrudes into my life, for example, I ask myself whether this state of affairs will exist or matter at the end of my life. Knowing that I probably won’t even remember something that’s bothering me now gives me the healthy perspective I need to make better choices about how to cope.

On the other hand, when I am struggling with a decision, I can also ask my future self whether I will someday regret that I didn’t make a certain choice. I visualize looking back on my life as having gone down either path, and I imagine how I will feel having lived with the consequences of each choice. Will I feel remorse or peace, sorrow or fulfillment?

Getting Advice From a Trusted Advisor: Your Future Self

Researchers for the keys to “doing the right thing” have come up with a fascinating experiment testing whether projecting oneself into the future could shape better decisions for today. Groups of college students were asked what they would do if they were strapped financially, needed a new computer and were told by a friend that he happened to know where they could get one cheap—wink wink, nod nod.

Before answering that question, however, all of the students were directed to write a letter to their future selves—describing themselves as if the future were now. One group was told to write to a future self three months hence, and the other group was told to write a letter to a future self 20 years out. And then they answered the question whether they would buy a stolen computer or not.

The students who wrote letters to themselves in the near future were much more likely to take the offer, while those who wrote to a distant future were much more apt to decline it. The reason is simple. Imagining yourself three months from now doesn’t give you a different perspective. You’re still in your same skin, identified with the “now” of your life. So if your present self were tempted by the offer, projecting three months into the future would be irrelevant.

When students described their imagined self in 20 years, however, they were able to step out of their narrative and craft a preferred vision of themselves. And as if this wiser and future doppelganger were reaching back in time, these students tended to make better choices that aligned with that wiser and better self.

Take the Moses Challenge

Try writing your obituary. Who will you be at the end of your days? What will have mattered, and what won’t? What do you want your loved ones to say about you and to have learned from you? What do you want to leave as your legacy? And then work your way backward, to today, and make choices that are designed to get you there. It’s never too late to do the right thing. You’re always one decision away from a totally different life. Do one thing today your future self will thank you for; it’s easier than you think.

Internalize & Actualize:

  1. When you were asked to write your obituary, how did that make you feel? No one wants to think about his or her death, but what was the initial response or feeling that you had? Use that feeling to motivate how you now think about your future. If you responded with dread that you haven’t done what you want to do, write down five things you can start doing to change that. If you felt at peace that you have lived a productive, filled life, write down what led to that and how you can continue to increase what you are doing for even more satisfaction.
  2. Think about a mistake you have made that at the time felt irreparable. Looking back now, was it as damaging as you initially thought? Even if the consequences were grave, what you have learned from that, and how has it shaped you?
  3. What is something you are worried about now? Is it something fixable? Will it be something that stays with you in the future? Write about this situation, but in 10 years from now, and see how much of an impact it will really have. Use that to help determine how much of your time and energy should be focused on it at this point in your life.