Can't Take It with You

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I started reading Bill Perkins’s “Die with Zero” while I was waiting for my plane to take off last night, and this blog post began percolating in my head by the time I hit page 12. I had already finished the piece that I planned to publish today, but I scrapped it and started this one around 9:30 PM at 33,000 feet. I hope you enjoy.

“I’ll take you anywhere in the world for two weeks, name the spot.”

The year was 2008, I was a few months shy of my eleventh birthday, and my grandma, Mama Ruth, had just offered me one hell of a proposition.

I was a geography nerd as a kid, and I knew the globe better than most fifth graders. At the time I probably could have named 100 or so countries, and I was familiar with the Sahara and Atacama deserts, the Nile and the Amazon, Everest and Kilimanjaro, and the Great Barrier Reef and the Outback.

So my imagination began running with ideas of adventure "anywhere."

But I didn’t think Mama Ruth really meant anywhere. There are some pretty insane places on this planet, after all.

After mulling over the idea in my 10-year-old mind, I decided to test the waters. Something international, but not too exotic. Something fun, but not too crazy.

“Costa Rica! We can zip-line through the rainforest and see all sorts of cool animals!” I said.

“If that’s really what you want to do, we can go to Costa Rica. But are you sure there isn’t anywhere else you’d rather go, or anything else you’d rather do? You can pick *anywhere*. The Great Wall of China? Somewhere in Africa or Europe? Be creative!”

Of course Costa Rica wasn’t my first choice. Don’t get me wrong, Costa Rica is awesome. But if I could really pick anywhere, I was going to pick the coolest place possible.

What is cooler than zip-lines in Costa Rica?

Lions, giraffes, rhinos, hippos, and cheetahs. Steve Irwin (RIP) played an outsized role in my childhood, obviously.

The answer, the real answer, could only be one thing:

“Can we go on a safari in Africa?”

“Sure. I’ll start looking for different tours.”

Six months later, I was boarding a flight to Arusha, Tanzania for a two-week safari with my grandmother.

I have visited 25 countries over the last year, allowing me to do and see some pretty cool stuff: hiking the Patagonia region of Argentina, seeing the Northern Lights in Tromsø, Norway, and cliff jumping on the Adriatic coast in Croatia, to name a few.

But nothing beats that pure joy I experienced as an 11-year-old seeing elephants and giraffes on the Serengeti Plain.

As a kid, I thought the trip was random, but it didn’t necessarily strike me as weird. My grandparents had taken me on business trips with them all over the States since I was old enough to talk, so what was one more trip with Mama Ruth?

But as I grew older, I became increasingly aware of just how rare and wild that trip was. What grandmother takes their 11-year-old grandson on an excursion to Tanzania by themselves? Wandering the streets of Arusha (even if we did have a guard)? Living in a tent in the shadow of Mt. Kilimanjaro? Flying a hot air balloon over the Serengeti (and almost crashing and dying as our "pilot" hit a tree on the way down)?Yeah, that's not a normal trip for an 11-year-old and his grandma. An insanely fun trip, but certainly not normal.

Five years later, while hanging out with my grandparents, curiosity got the best of me.

"Mama Ruth, why did you offer me a trip anywhere in the world? That's a pretty wild proposal for an 11-year-old."

"Well Jack, I have plenty of money, I'm not going to be around forever, and I can't take it with me. I could either spend it on my grandkids now or leave it to them as an inheritance. What better way to spend some of that money than on trips with my grandchildren?"

Mama Ruth has since taken my sister and 3/4 of my younger cousins on similar trips around the world, from China to Europe. I actually tagged along for the last one in Italy and Spain a few months back. 

"I can't take it with me."

Such a simple statement, but one of the few universal truths. You spend your life accumulating money, then you die and your stuff gets left behind. We humans tend to focus on the first part of this equation while ignoring the latter until the lights come on, Closing Time by Semisonic plays on the speaker, and we realize that it's time to go.

For the unaware, this is the 3 AM "bar is closing" ritual consistent across all of America's greatest dive bars.

As a kid, I just thought it was cool that Mama Ruth took me to Africa while most grandparents just go to Florida. As I grew older, I began to realize both how important and intentional this decision to travel with her grandkids was.

We obsess about money. We want to make as much as possible, we want to retain as much as possible, and we fear that we may one day run out of money. But this fear is largely unfounded.

As my friend Nick Maggiulli pointed out in a recent blog post, the average retiree leaves behind hundreds of thousands of dollars when they die. To use a casino analogy, they never cash out some of their chips.

Nick's recent post pointed me toward Bill Perkins's Die with Zero, a book that explains the unorthodox philosophy of spending as much of one's money as possible while still alive.

(I highly recommend this book, by the way.)

Perkins took a quantitative, almost mathematical approach to the idea of spending the majority of one's money. If money and experiences are two variables, and you are constrained by time, you want to spend as much of your money as possible on the experiences that you value while you are alive.

He echoed the sentiment that my grandma told me a decade ago: You can't take it with you.

Money is only as valuable as the experiences that it buys, and your window of opportunity to realize some experiences is quite short. As Mama Ruth understood, grandparents only have so much time to share experiences with their grandchildren. As Perkins discovered a few years too late, young adults only have so many years to experience the thrill of hostel hopping through Europe or Asia.

Once a window of opportunity closes, it's gone forever. You can always make more money. You can't "buy back" time gone by, or experiences not experienced. No dollar amount can give 65-year-old you the vagabonding adventure that you skipped in your 20s.

When you spend most of your life ignoring the reality of your final destination, you never develop a sense of urgency. When you think you have all the time in the world, you risk falling asleep at the wheel, going through life as a passenger instead of an active participant.

I think all people, at some point in their lives, experience an existential shock that radically changes how they spend both their money and their time. When you realize just how finite your time is, you start maximizing how you use it.

Unfortunately, most people only grasp this reality of the human condition when it's too late to do anything about it. Old age and a terminal diagnosis often serve as catalysts for being more intentional with one's life, but by then you lack the time and energy to take advantage of your newfound epiphany.

Starting with the end in mind is uncomfortable, but it offers you the chance to build the life you want. To be captain of your own vessel, charting your path through the sea.

I experienced my own existential reckoning at the ripe age of 23. At the time, I thought it was a curse. I mean dude, I was 23. What 23-year-old wants to deal with questions of "meaning" and "the shortness of time"? What kind of Ryan Holiday BS was this? I just wanted to hang out with my friends. Save the existential dread for the stoics.

In hindsight, this wake-up call was a blessing. I was still young enough to take advantage of all of the world's experiences. To construct a life that I wanted, instead of falling in line with some preordained path.

I took my wake-up call and ran with it, and I can honestly say the last year has been the best year of my life.

I can't tell you how to spend your money or your time. What I can tell you is that I have never once regretted spending money on experiences, but I know plenty of older folks who would pay anything to have a second chance at the experiences they missed.

Can't take it with you.

- Jack

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Jack's Picks

• In the spirit of this article, I highly recommend giving "Die with Zero" a read. Bill Perkins is a hedge fund manager, professional poker player, and travel enthusiast who has figured "life" out. Check out his book here.

• Nick's piece that led me to Bill's book was great as well. Give it a read.