The Game We Play

How Death and These Two Questions that Changed the Way I see Time, Money, and Meaning

How foolish are we that just because we have taken one breath, we believe we will take another” - Unknown

This Father’s Day felt empty. Since my dad’s passing in April, I’ve amassed a mental list of life updates and sporting events that make me want to call my dad and to give him the latest, and that desire was far stronger than I expected this past weekend. I felt guilty. I couldn’t recall what we talked about last Fathers Day, but I had this feeling I probably called him while I was in the middle of something else. How many times could I have picked up the phone just to say hi and I didn’t? There’s no chance to course correct.

My dad’s health (and particularly his mental health) had been deteriorating for well over a year. He needed help, but he often refused it. Over the course of the last year, I had considered that it was possible that he could die, perhaps a coping mechanism more than anything else.

It is the mere fact that one day he was here and gone the next that is impossible for me to reconcile. I fear that you have to experience this type of loss to understand. You simply are…and then you’re aren’t. You are no longer able to write your own story. Your legacy is determined by the strength of other people’s memories.

Perhaps I’ve spent a little too much time contemplating mortality over the last few years. It’s easy to think we have so much life ahead of us. Heck, in financial planning, we plan for long lives in retirement and we constantly talk about the benefits of delayed gratification. My dad only made it three years into his retirement. Every time I see a post about the benefits of delayed gratification, I want to throw up. There is a useful principle in there, sure. I don’t think we should YOLO every decision in our lives. But, if I can use my dad’s experience as a cautionary tale, under zero circumstances should we delay living.

In 2023, I read this quote from Michael Singer’s The Untethered Soul. I actually hadn’t read the book yet, but this quote popped up on a blog from a fellow planner turned good friend, Justin Castelli.

“You fear death because you crave life. You fear death because you think there’s something to get that you haven’t experienced yet. Many people feel that death will take something away from them. The wise person realizes that death is constantly giving them something.”

"If you are living every experience fully, then death doesn’t take anything from you. There’s nothing to take because you’re already fulfilled.”

That quote changed my life. I had spent far too much time thinking about things I couldn’t do, or couldn’t do yet. The time wasn’t right. I hadn’t built any meaningful good will in my career. I was just starting to save money for the first time. The list could go on.

I realized I was a squirrel accumulating nuts for a winter I never intended to live through. Build career capital, save money, work hard, store nuts. That was my mentality. Until after ten years you just realize that you need more of all of those things still. At some point I needed to ask myself, “What fucking treadmill am I walking on.”

Singer’s quote changed the way I thought about the travel I’ve always talked about. It reminded me of the business I always wanted to start. It helped me think about my relationships with my friends and family. If I didn’t make conscious choices about those things now, the right time might never come. I would be the subject in Bronnie Ware’s Top Five Regrets From Dying. I could see myself on my own deathbed 50+ years from now (if I’m lucky) looking at the periods of my life that had passed me by, all while I dreamed that I had done something different.

I promise there is hope in this story. As I’ve continued my own contemplations of my mortality, I’ve come across a few questions that have given me the power to contemplate death in a meaningful way. My hope in sharing isn’t to scare you, but to serve as an offering. It is an offering of hope, an offering to create meaning and connection, and a reminder that our time on this earth isn’t given lightly. Your life is a gift.

How to Safely Contemplate Our Finitude

As I reflect on my journey the last few years, there are two questions I’ve been trying to sit with almost every day. Instead of ignoring these questions, I’ve spent time with each of them. In return, I’ve found a clearer sense of direction, and more importantly, a gratitude for the fragility of life.

How Many Times Left?

I used to have a poster on my desk at work with a print out inspired by Tim Urban’s “Your Life in Weeks.” It’s a simple visual. Fifty two small dots across a page, each representing a week. 90 rows of dots, each representing a year.

My cube neighbors would joke that I was far too existential, but to me it was a simple reminder of just how short life is. Within the self help space, I hear this question pop up repeatedly. How many times left will you have?

How many more summers do you have with your kids at home before they leave the nest? If you want to narrow it even further, how many years will your kids and your dog be around?

How many Christmases might you have left in your life? How many might you have left that overlap with your parents? How many of those would you expect to be the same, perhaps before your parents start to require ongoing care?

How many times can you get together with friends from growing up before life gets busy? Before they move across the country to start their own family?

How many times might we be able to take big adventures in our life, before our bodies start to rebel against us?

What was a rather large board of sequential dots with opportunity galore, has been sifted into remarkably small and short stretches of time. I find that we walk through life often believing that we have an infinite number of dots in our future. We tell ourselves that we will always have time to achieve our goals later, often neglecting the reality that the chances of achieving our dreams, hopes, and aspirations are slowly dwindling over time. The idea of spending time with the people we love can feel like a nagging or annoying requirement at times, a thing to be “slotted in” to our otherwise busy and important schedules. We don’t realize how terrifyingly narrow our windows of opportunity in life may be for the people we care about and the things we dream about.

I was no different. Early in my career, I passed up opportunities for travel and adventure thinking I could always do it later, particularly when I was more established in my career and had more money. I’ve had a friend tell me about a ski trip they always wanted to do with their dad, only for age and knee troubles to throw a wrench in those plans. I once had a dream that I would take my dad to the rest of the ballparks we hadn’t been to, and complete the tour he started with me when I was a kid. Since he passed, I’ve struggled to accept that dream will never come to life.

For me, the question is a stark reminder of just how few opportunities we have left in our life for the things that are important to us. People grow up, friends have families and move away. Life gets more complicated as we get older, there is no doubt. We are asked to juggle more responsibilities at work, and we do what we can to carve out whatever remaining time for our families and our hobbies. Circumstances, logistics, and cost will always make things complicated, but the harsh reality is, when we choose the busyness of life over creating moments, memories, and meaning, we are consciously erasing an opportunity that we will never get back.

More optimistically, the “how many times left” question is also a reminder to truly cherish those moments when they do happen. It’s so easy to think, “just another Christmas with the family” or to complain about how expensive flights might be. I’ve been caught in that trap myself. I came across the Japanese concept of Ichi-go, Ichi-e recently. It roughly translates to “one time, one meeting.” The idea is to treasure the uniqueness of each moment because no two moments are ever the same.

Yes, we might go home for Christmas every year. Yes, we might meet up with our friends once a month for happy hour. But how many times do you go do those things and proceed to scroll through your phone? Maybe you catch up a little bit, but the odds are that we start to feel the “regularity” of those events and we start to take them for granted instead of seeing the beauty of each of those tiny interactions. There is always something beautiful to cherish in each of those moments, and it often sits just on the other side of discomfort (which is the moment you normally decide to pull out your phone).

Kinder’s Three Questions

The idea of life planning was born out of George Kinder’s Three Questions. The questions are as follows:

1. I want you to imagine that you are financially secure, that you have enough money to take care of your needs, now and in the future. The question is, how would you live your life? What would you do with the money? Would you change anything? Let yourself go. Don’t hold back your dreams. Describe a life that is complete, that is richly yours.

2. This time, you visit your doctor who tells you that you have five to ten years left to live. The good part is that you won’t ever feel sick. The bad news is that you will have no notice of the moment of your death. What will you do in the time you have remaining to live? Will you change your life, and how will you do it?

3. This time, your doctor shocks you with the news that you have only one day left to live. Notice what feelings arise as you confront your very real mortality. Ask yourself: What dreams will be left unfulfilled? What do I wish I had finished or had been? What do I wish I had done?

The purpose of the third question undoubtedly forces us to contemplate our mortality. As I’ve worked with clients, the most meaningful and important bits of life rise to the surface, often coupled with intense emotion. But to me it’s the order of the questions that makes this exercise so powerful.

The first question allows you to explore what’s possible and to dream without restraint. So often we wait to dream until the circumstances are perfect or we whittle our big dreams down to something that is hardly recognizable based on our current circumstances. The question allows us to dream with childlike wonder again.

The second question helps us arrange what’s most important in our lives. Having to consider our own mortality allows what’s truly important to bubble up to the surface. Spoiler alert to most employers out there….most people want to quit their jobs.

But it’s the last question that truly shines a light on what we consider most meaningful in our lives. For me, taking big risks (particularly as it relates to starting this business) wasn’t in my DNA. It conflicted with my need for safety and security. I was a squirrel collecting my nuts! But Kinder’s third question forced me to consider that I would regret not taking the risk. I would never get to explore this future with enthusiasm, and fear, and pain. And while it felt like I could avoid some of those feelings by trudging along a certain path, I realized that the magic to create, to live, and to be free requires feeling each of those emotions. Deeply.

A Way Forward

Since my dad’s passing, I’ve felt remarkably ok. I feel like people kept looking at me like they expect me to be broken or assume I’ve lost everything. I am devastated that I won’t get to share any more memories with my dad. But for the last few years, I’ve tried to embrace the essence of these questions and to regularly contemplate my own mortality.

The gift I’ve received from contemplating death is that every moment is precious, and nothing is guaranteed. In my experience, many of us eventually come to this conclusion, but it often comes in the form of pain and immense heartbreak. Often we have to lose someone, or something unexpectedly, to cherish and appreciate the gift of life. To consider these questions allowed me to truly see my father in every moment. Some were more difficult than others, but the thing I would have regretted most was not showing him love and gratitude for everything he’s given me.

So ask yourself “What chips am I wagering today?” How many opportunities might you have left when you look at your 52x90 block of dots? If your doctor told you that you only had a day left, who did you not get to be? What did you not get to do?

I encourage you to sit with these questions for longer than you might be comfortable. Listen to what your heart, your mind, and your soul are telling you. They will give you your North Star.

Whether we acknowledge it or not, we are wagering our lives every day. That’s the magnitude of the game we are playing. And it makes each moment feel a bit more important and full of joy when we know what’s at stake.

Thank you for everything, Dad

“Putting things off is the biggest waste of life: it snatches away each day as it comes, and denies us the present by promising the future. The greatest obstacle to living is expectancy, which hangs upon tomorrow and loses today. You are arranging what lies in Fortune’s control, and abandoning what lies in yours. What are you looking at? To what goal are you straining? The whole future lies in uncertainty: live immediately.” - Seneca