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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Perhaps no one has quit their job like my guest today, Cory Richards. Richards, still a world-renowned photographer, abruptly ended his career as an elite mountaineer in April 2021 at the foot of the world’s seventh-highest peak. Over several days, Richards experienced what he later described as a mixed bipolar episode.

With one hundred thousand dollars spent and a film in the works, Richards announced to his team at Dhaulagiri’s cold and windblown base camp that he was quitting—not just the expedition, but climbing altogether. He told his livid teammates he planned to move to Los Angeles to pursue filmmaking and writing. The pressure cooker of personal history, fame, high achievement, and perhaps the exhaustion of living someone else’s life boiled over.

In 2011, Richards became the first and only American to climb one of the world’s 8000-meter peaks in winter. On the descent, the team narrowly escaped death in an avalanche. In the aftermath, Richards snapped the iconic frozen selfie that adorned the cover of National Geographic’s 125th-anniversary issue. He was the 2012 National Geographic Adventurer of the Year and a 2014 National Geographic Photographer Fellow. He summited Everest without oxygen, garnering over two billion media impressions with his partner Adrian Ballinger as they Snapchatted their way up the mountain in 2016.

For years, people lived vicariously through him. He garnered over a million Instagram followers. Everyone told him he had the dream job. He traveled nine months each year across the globe to distant and stunningly beautiful lands to climb and take pictures. But in his own words, he “hated it.” He was an addict, fueling a burning fire with alcohol, sex, and tremendous pressure to do more and go bigger in increasingly deadly circumstances. Then it all fell apart.

His memoir, The Color of Everything, is set to release on July 9. It’s a gripping and shockingly frank account of Cory’s life struggles. From his adolescent mental health diagnosis to a life of addiction and denial, he’s found the slow path toward acceptance. This is a story of personal growth, societal pressures, and the complex interplay between vulnerability, achievement, and emotional resilience.

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Recently, I’ve been increasingly conflicted by several dueling experiences and sensations:

1. Reduced Stress: Since departing from the Standard Corporate Office Environment (SCOE), I’ve enjoyed decreased stress and anxiety levels. While stress has its upsides, reducing chronic stress is foundational to living a good life.
2. Mounting pressure to be part of society. I’ve been working on this project for six years, but being a home-based blogger and podcaster isn’t fully satisfying some of the key pillars of a meaningful life.
3. Decreased Motivation: I’m finding it hard to engage tasks not entirely aligned with my vision of a good life. Paradoxically, a good life involves doing hard things.

Here's the good news on how to maintain a strong financial base and do work you love.

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Imagine being faced with the daunting task of predicting the future with nothing but incomplete information and a handful of hunches. Perhaps you're considering new experiences, like travel or moving to a different town. When I imagined quitting my job, I envisioned a happier world, free from the perceived burden of corporate work. In the following months, however, my expectations were shattered upon realizing that I still largely felt the same despite my newfound freedom. In recent years, this recognition has remained vivid, sparking my curiosity about why predicting outcomes in the face of uncertainty is so difficult.

Whether anticipating a geopolitical event, forecasting stock market trends, or simply contemplating life’s next move, accurate prediction is an ever-present challenge. As I began to journal in earnest some years ago, I uncovered a fascinating trend hidden between the mundane details: my predictions were fraught with overblown concern and startling inaccuracy. Delving into the complexities of prediction and expertise, it becomes clear that many factors—from biases and cognitive distortions to the whims of randomness—shape our perceptions of certainty and accuracy. Despite these hurdles, new research offers a glimmer of hope.

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