A few months ago, I published a piece called Life Lessons from 1,000 Years based on my request for life advice from a number of wise nonagenarians.

The advice that these 90-year-olds offered to their younger selves ranged from playful and witty to deeply moving. Some were common tropes repeated over the years (and for good reason, as they bear repeating!), others were original and thought-provoking.

The whole exercise sparked my thinking about regret: Specifically, I became fascinated by what these folks seemed to regret about the way they had lived their lives during their prime years.

• What had they done (or not done) that they had come to regret later in life?
• Could these regrets have been avoided by heeding this advice?

I began to wonder if there was a way to reverse engineer the process—to figure out what regrets I was likely to have at the tail end of my life, so that I could live life today to avoid them.

I wondered if we could take a peek into our future in order to establish our core values for the present.

In today's piece, I'd like to walk you through the exercise I developed to do just that...

The Deathbed Regret Exercise

"If you do not change direction, you may end up where you are heading." – Lao Tzu

We're often told that we should live life according to a core set of values. The challenge, of course, is in determining and defining what these core values are.

The Deathbed Regret List is the most efficient and illuminating process I've discovered for defining and clarifying the core values with which we should live our lives. It forces you to begin with the end in mind.

The exercise has three key steps:

1. List Your Regrets: Make a list of your most likely deathbed regrets. What are the things you know you'd regret on your deathbed? This is deeply personal—don't write down what you think you should say, write down what you will actually regret. This is an exercise for you, not for anyone else.
2. Establish Your Values: Formulate a set of 3-5 core personal values that are highlighted by your regret list. What are the common themes of the regrets you listed? These common themes are likely to shine a light on the things you value most deeply in life.
3. Determine Your Actions: For each core personal value, determine the actions you can take today to behave in line with that value (and avoid the eventual regrets). Are you currently acting in line with these values, or in a manner inconsistent with these values? Be honest. If you continue on your current path, will you have these regrets? If so, what changes need to be made to avoid them? How can you redesign your life to avoid these regrets?

In order to bring this exercise to life, here is my list of deathbed regrets, plus the actions and commitments I am making to avoid them...

My Deathbed Regret List

Deathbed Regret: Not spending enough time with my kids during the Magic Years.

There's a devastatingly short window of time during which you are your child's entire world.

After it, they have friends and partners that fill that role.

I refuse to miss those precious years. I will be a present father and manage my professional commitments and time to embrace those years.

Deathbed Regret: Not spending enough time with my parents during their remaining years.

The time we have with our parents is limited—the vast majority of it behind you by the time you leave school.

I won't hide from the scary math—I will prioritize this special time with them.

Deathbed Regret: Not training my body and mind during my middle years.

It's easy to let other priorities step in front of your physical and mental health in your middle years.

But if you stop training body/mind, they will fail you in your later years.

I will prioritize it.

Deathbed Regret: Allowing true friendships to atrophy over time.

True friends are few and far between.

It's easy to let these friendships wither—distance and life make get togethers harder.

I will be the friend who checks in and plans the gatherings to keep them thriving.

Deathbed Regret: Allowing negativity to linger in my life.

It's easier to allow negativity to linger than to have the tough conversations to eliminate it.

But negativity is a black hole—it sucks the happiness from your universe.

I will confront it and ruthlessly eliminate it.

Deathbed Regret: Letting money control my life.

There are very few things in the world I find as sad as the "rich-yet-miserable" existence.

I have no desire to be the person who lets money rob me of my time or fulfillment.

Assuming our basic needs are met, I will always place family ahead of money.

Deathbed Regret: Not leaving something that lasts beyond my life.

Your children and grandchildren will remember you, but your great-grandchildren probably won't.

Family memories only go so far.

I will strive to leave a mark on the lives of those less fortunate than I was.

Deathbed Regret: Wasting precious time stressing about stupid little things.

It's so easy to get caught up in the daily stresses of life.

But if you get absorbed by every little stress, life takes on a sad dullness.

I will handle real stressors and "opt out" of stupid stress.

Deathbed Regret: Not working on things I consider meaningful.

We get one chance, so why use our precious mental energy on things that feel small.

This isn't about someone else's definition of meaning—it's about yours.

I will make sure I work on meaningful projects.

My bet is that if I do deep, focused work on projects I consider meaningful, I will create something valuable for others, which implies that the money will take care of itself.

Deathbed Regret: Allowing my quest for more to distract me from the beauty of enough.

Ambitious people will chase whatever more is on the horizon.

But true wealth is found not in attaining more, but in discovering your version of enough.

I will always be grounded by my enough.

What Are Your Deathbed Regrets?

Those were the 10 things I know I'd regret on my deathbed—and my plans for how to live to avoid them.

I conducted this exercise to clarify my core values and design my life in a way that would minimize my regrets in the end.

I first went through it by myself, but am now encouraging all of my family and friends to do the same. My intention is that we will have a "summit" where we can all walk through the learnings from our exercise together and find points of alignment where we can grow closer as a unit.

The Deathbed Regret List is an illuminating and inspiring exercise that everyone should consider going through.

To conduct your own, simply ask yourself these questions:

• What are the things you know you'd regret on your deathbed?
• If you continue on your current path, will you have those regrets?
• If so, what changes need to be made to avoid them?
• How can you design your life to avoid those regrets?

I recommend doing the exercise by yourself, but then coming together with a group of loved ones to discuss and reflect on your learnings.

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