How a brush with death shaped my long game

Last February, I opened my laptop and began writing a goodbye letter to my 18-month-old daughter.

“Dear Bea,” I began. “I want you to know how much I loved you…” I then carefully organized passwords to my computer, e-mail, and online brokerage accounts. My wife and I sat across from each other on the couch in stunned silence.

Hours earlier, I was told by ER doctors that I’d need emergency brain surgery to remove what they called a “rapidly enhancing lesion” in the center of my cerebellum, the part of my brain just above the brainstem. The lesion was about the size of a walnut. 

At that point, doctors were unsure what it was. They explained it could either be a Stage 4 glioblastoma — terminal brain cancer — or an abscess that could pop at any point. If it was an abscess, the infection would likely prove fatal as well, given its proximity to my brainstem. 

I sent out texts to friends and family, telling them my news, and that I loved them. My parents boarded a flight out west. My closest friends mobilized to support my wife with whatever she needed. 

That night, hours before the brain surgery, I laid in bed unable to sleep. I remember thinking about the crushing irony of my particular situation. For the last several years, I had built my professional identity around the idea of long-termism. I wrote a weekly newsletter about long-term investing; about compounding over many decades. I loved to quote investors like Warren Buffett, who said things like, “​​Our favorite holding period is forever.” I truly believed it, too. I believed in the notion that all good things take time…

And yet, here I was: 35 years old, and out of time. No more compounding. No more long-termism. Hell, our firm’s tagline — that I myself wrote — was “investors focused on the future.” 

As for me, that future was collapsing. Time had run out. At that precise moment, the idea of long-termism or “playing the long game” began to feel almost embarrassing — or ridiculous. The idea was like an act of hubris. The future isn’t earned; we’re lucky to experience it. 

The truth is that I had never even considered this possibility. I hadn’t modeled out this scenario as a tail risk in my life’s prospectus. Sure, we all intuitively know that life is precious and can end at any moment. We are all familiar with the hackneyed expressions — life is short, carpe diem — but how often do we actually think about this until it matters?

I certainly didn’t. I took my youth for granted. 

Even if I survived the surgery, I was told, metastatic cancer of the brain meant a nearly-certain death. The neurologist in the ER suggested, somewhat nonchalantly, I could have three months left to live. Maybe six. I thought: I won’t make it to my daughter’s 2nd birthday. For the first time in years, I cried.

Before this episode, I never had a significant health problem. But the truth is that I wasn’t living an entirely healthy, long-term-oriented lifestyle. I was constantly stressed at work. I had stopped exercising. I was glued to my phone — and to the market. In the months leading up to my condition, we were having a rough year, and it was all I could think about. I’d dream about stock prices. I’d wake up in a panic. 

Despite the ideals of long-termism I professionally and publicly promoted, I was, in fact, living a lifestyle that was just the opposite. I was myopically focused on the short-term —on success, on the day-to-day. I avoided seeing friends; my marriage was becoming strained. Things were unraveling. 

And then, one afternoon in January 2023, seemingly at the bottom of my turmoil, the symptoms began. In one of my hospital visits before the second MRI found the lesion in my brain, I texted one of my friends, Tom, about my situation. Weeks earlier, I had confided in Tom about the stress and anxiety I was feeling at work. Tom, a former finance guy himself, had a blunt, if not philosophical take. “This kind of shattering event is showing up right on schedule,” he wrote me. “It doesn’t mean it will be at all pleasant but it might be redemptive. It’s the horrendous reset that’s going to set you up for the real creative synthesis stage.”

On the morning of my surgery, I tried to finish the goodbye letter to my daughter that I had started the night before. The clock was ticking. Parents, I ask you: what do you write to your 18-month-old child the day before you die? Sure, you tell them you love them. But what else? How do you cram a lifetime of knowledge into one little letter? 

I wanted to write about creativity. I wanted to write about risk — and how to stay safe. I wanted to write about money, investing and security. I wanted to write about heartbreak. I wanted to give her an instruction manual for life. If you are a parent, you will understand this implicitly: the only thing in your life that matters is your child’s safety. And when you cannot protect them, you are destroyed. 

That morning, I hugged and kissed my daughter. They shaved my head and readied me for surgery. I held my wife. I called my parents. 

I texted my closest group of guy friends. I tried to keep a sense of humor. Take care of my family, I wrote to them. “Or else… I’ll haunt your asses as a ghost.”

And that was it. The anesthesiologist stepped into the room. “Count backwards from 10, 9, 8…” Darkness.

In my mind, I traveled a million miles. And then, a funny thing happened. 

I woke up.  

Here is the good news: Sometimes it just works out. 

The craniotomy was a tough procedure. They removed a large chunk of skull in the back of my head, spread open my brain with forceps, and removed the lesion. 

When I woke up in the intensive care unit, I saw my surgeon standing there. 

“Is it cancer?” I asked. 

“I don’t think so,” he said. 

He explained the pathology report needed to come back, but he was confident it was, indeed, a one-in-a-million rare brain abscess. A bizarre infection. 

Finally — and it’s easy in hindsight to breeze over the days it took — the report came back conclusive: an infection. Not cancer. 

Later, I’d find out that typical abscesses rupture after 10 days or so. Mine had been in my head for at least 4 weeks. No doctor could explain it. I had a ticking time bomb in my brain that simply didn’t explode. Maybe the detonator malfunctioned. 

Months of tests following the surgery didn’t provide many answers. No source of the infection could ever be found. It was like an episode of House, one of my nurses said, but without an ending. After dozens of doctors visits, no one could ever explain why it happened. Or why I’m still alive. 

Does it matter? Like my friend Tom said, perhaps this was the “horrendous reset” I desperately needed. It was a wake-up call, and a dramatic one indeed. 

So here I am. Call it a miracle. Call it luck. My heart is beating. My daughter turns 3 in July. The sun is shining. Or it’s cloudy. It doesn’t matter. If you are reading this, take a pause. Take a breath. You are alive. In August, my wife and I, closer than ever, are going to have another child: girl number two.

When people ask about how the experience has changed me, I simply say I’m re-committed to playing the long game. 

Playing the long game isn’t just about structure and process and systems that are designed to withstand the long-term: it’s about the joy and gratitude of getting to play the game in the first place. For me, up until that point in my life, I had been making short-term decisions that led to stress and burnout. And, in retrospect, my “always on” lifestyle likely led to my near-fatal brush with death. Stress and playing short-term games quite literally nearly killed me. 

My focus was all on the wrong things.

Coming out of this experience, I proactively shifted my focus. I decided to make both personal and business decisions that would create an environment where the most important things in my life could flourish long after I was gone. I read more. I talked to new people. I made more effort in my relationships — I no longer think about getting through the day, but what I’m building over the long-run. I put down my phone. I made new connections. I asked, “how can I set up my life today to ensure my kids — and their kids — will be set up?” In business, I asked, “how can I set up my business today to ensure it exists in 50 years — or even 100 years?” 

In essence, I took a big step back and looked at what really mattered to me: family — my wife and kids — and building my business with a more thoughtful approach towards longevity. This required change, which is hard. That’s the point. Playing the long game is not easy.

Ultimately, the reason I play the long game is simple: the long game isn’t actually very long. Life is short. I want to enjoy it. But we have limited time to make decisions and set up structures in our life to maximize the chances that things work out in the future. So we need a strategy to play the long game — we need a playbook. 

I’m writing The Long Game column because I know there are so many people out there who want to play the long game — in business, investing, and life — but don’t. Our culture is obsessed with the short-term. With metrics. With 24/7 breaking news. It’s hard to step above the fray and make hard, consistent decisions that lead to compounding magic. But I know there is a desire to live more intentionally in this way. 

The Long Game columns will feature lessons and ideas inspired by writers and thinkers and entrepreneurs and investors and artists and therapists and buddhists and philosophers. It’s about people and businesses who have achieved extraordinary things over the long-term. Much of our popular media tends to focus on overnight successes, the “30 under 30” lists, and so on. This column is different. It’s about how to think long-term, while still acting decisively in the moment. As an investor, this is all I think about: how do I make decisions today that will play out well in the coming years? There is a playbook, and I want to share it. 

In the last year, I’ve realized something. Being long-term is not actually about the future. It’s about the present. It’s about consistency; it’s about discipline. It’s about giving yourself a reason to be in the game over the long-term. So, why do I play the long game? I play it because I can. Every day is a bonus. I’m very privileged to be here. 

I wish you all health and luck, in that order. 

Until next time.