I’ll begin with a secret: I never cared much about the nuts and bolts of personal finance (the means), but I was rather enamored with the idea of a financially secure life (the ends). In 2018, climbing media was still full of narratives glorifying the poor dirtbag ideal, but that didn’t align with my lived experience. I wanted to climb hard, while also yearning for meaningful work and financial security. That’s the first half of this story.

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From a market perspective, history has always favored the unfazed, the patient, the forgetful. Drastic action in times of great uncertainty is almost always the wrong move. Time and again—just like now—people convinced themselves of imminent disaster. And in nearly all cases, they were wrong. Financial writers and hardened optimists are right to remind us: “This time isn’t different.”

But I’ll be straight with you: This time might be different.

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I’ve made it my goal over the past few years to steer people toward financial independence but away from early retirement. I have many reasons, and I’ve laid those out over numerous blog posts and podcast episodes. These are the big themes:

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I’ve drifted in and out of the meritocracy trap over the years, but mostly, I’ve stayed stuck in its sticky web. I quickly learned the value of good grades and securing better jobs. Once I landed a good job and the race to secure it was over, I descended into despair at the thought of doing it for the next forty years. Fast-forward a decade, and financial independence allowed me to sidestep the meritocracy trap. However, this too felt like another shiny merit badge. When I reached that point, I looked around and realized, like a bus rider stepping off at the wrong stop: damn it—this isn’t it.

Who would have thought you couldn't find happiness by looking for it?

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My wife and I stood at the edge of the world—or at least what felt like it—squinting through the murk and sea spray to snap photos of a decommissioned lighthouse. Less like some beacon of hope, its white tower loomed like a ghost, haunting the craggy cliffs of coastal Victoria and my vacation prospects. We’d arrived at the sleepy Victorian coastal town of Port Fairy expecting sunshine, a pleasant breeze—and if not asking too much—maybe a kangaroo or two bounding in silhouette against the sunset. Instead, a spectrum of misery lay before us: wind that could strip the paint from a car and rain in erratic, bipolar bursts.

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Australians, it seems, are utterly smitten with coffee. The beverage of choice appears to be the flat white, a silky yet buttoned-down cousin to the latte or cappuccino. We landed in Sydney at dawn, dragging two hefty bags from baggage claim. Our first order of business was to snag a flat white before leaving the terminal. Ever the minimalist, I settled for an espresso, watching the crowd in a bleary-eyed daze, squinting at the sun as if it were a new concept. My wife, meanwhile, sat busy photographing her artfully swirled toothpick masterpiece. Soon enough, we embraced the day and ventured out into the land of sculpted asses in Bondi Beach.

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They say that grief comes on like a tsunami, a wave of incredible power and uncontrollable force that washes over us. The metaphors are many—trains and dump trucks, roller coasters and rivers—and they all check out. Grief comes on hard and renders us powerless in its wake. But I’ve been consumed less by a powerful force and more by the emptiness of where something used to be. Because grief is, after all, an empty hole. And it hurts because I allowed myself to love so deeply and unexpectedly. After all, loving never came easy until I met this dog.

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Retirement is often an ideal detached from reality. When overwhelmed by daily routines, it’s easy to imagine retirement as a stress-free life with a blank calendar and complete freedom. However, retirement often brings unexpected psychological challenges, including a lack of purpose, boredom, relationship strain, and a troubling sense of isolation.

Today’s guest, David Champion, retired from his software development career at 53. Nearly five years later, a line from one of his blog posts for Can I Retire Yet? titled Confessions of an Early Retiree jumped off the page. He wrote: “I am a proponent of retiring as early as possible.” While he had no regrets about retiring early, he later admitted to experiencing significant psychological challenges. In our conversation, David reconciles his “no regrets” view of early retirement with the difficulties of adapting to life without traditional work. Throughout, David highlights the need for self-awareness and embracing one’s true identity to find fulfillment in retirement (and climbing).

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