At just 41 years old, Jeremy Finney believed he had achieved the ultimate American dream: the freedom to walk away from his lucrative tech career, having saved enough to never work again. His journey to early retirement was marked by relentless dedication, often clocking 70-hour weeks filled with back-to-back meetings and even a staggering stretch of over 50 hours straight without a wink of sleep. Typical workweeks had him leaving his Windsor, Ontario home as early as 4 a.m. on Mondays for trips to Chicago, only to return late on Fridays.

“Work-life balance? I completely abandoned that concept,” reflected Finney, now 45 and approaching his 46th birthday. But upon retiring five years ago, instead of experiencing the expected liberation, he found himself engulfed in a feeling of emptiness.

"I realized that my driving force wasn't just financial gain; it was my passion for the work itself. Once that passion disappeared after I left, I realized I hadn’t cultivated any alternatives to fill that void,” he shared. Finney is among an increasingly prominent group of Canadians opting for early retirement in their 30s and 40s, many influenced by the FIRE (Financial Independence, Retire Early) movement. Yet, these early retirees often face an unexpected emotional fallout: regret.

A 2019 poll by CIBC revealed that over 25% of retired Canadians expressed remorse regarding their decision to retire, with nearly a quarter attempting to return to the workforce. Alarmingly, close to 60% cited a lack of intellectual engagement as a primary reason for re-entering employment.

For individuals like Finney, who sacrificed personal relationships and hobbies to achieve financial freedom, the sense of regret can be magnified. As they chase an idealized vision of leisure, they often discover that retirement is not the joyful respite they envisioned. Finney, whose demanding job hindered him from savoring holidays, believes the relentless stress may have even contributed to the breakdown of his marriage.

Initially, Finney's exit from a high-pressure job felt perfectly timed: the global COVID-19 pandemic was keeping everyone indoors, and with two young children to care for, there was certainly no shortage of responsibilities. However, as time dragged on, he began to grapple with the absence of structure and a sense of purpose in his life.

“I need more than just freedom to feel fulfilled,” he admitted. “I assumed that after years of a fast-paced life, I would fully enjoy doing nothing, but that didn’t turn out to be the case.”

Financial planners, like Winnipeg’s Kaitlyn Douglas, note that around 75% of her clients are interested in retiring before 65. Yet, she has seen many struggle to find purpose in their lives after walking away from their careers. The FIRE philosophy often promotes extreme frugality, where individuals can find themselves sacrificing relationships and hobbies in the relentless pursuit of wealth.

Ainsley Mackie, a chartered investment manager at Verecan Capital Management, frequently hears from early retirees who wish they hadn’t sacrificed so much in their chase for financial independence. “By saving so aggressively while they’re young, they often miss out on valuable life experiences, negatively impacting their overall quality of life,” she notes. It’s a lonely experience for many young retirees, who find themselves without peers to share their newfound leisure time.

For those who reconsider their choice to retire early and aim to return to work, the process is fraught with challenges. CIBC's study indicated that only one-third of retirees seeking to re-enter the job market find positions comparable in status or salary, while the majority either settle for lower-paying jobs or simply give up.

Finney is currently navigating these rough waters. Today, he plays the Irish fiddle part-time but is contemplating rejoining the tech industry full-time. Yet, in a field that evolves at lightning speed, he feels as though he may have fallen behind, saying, “Five years can feel like a lifetime in technology. The thought of making a comeback without significant retraining is daunting.”

As people like Finney reflect on their early retirement decisions, it's clear there are deeper lessons to be learned. The journey to financial independence may be alluring, but without proper preparation for life beyond work, the golden years may not shine as brightly as anticipated.

In a world where the promise of early retirement is heavily marketed, it begs an important question: is it worth it? Only time will tell for those navigating the complexities of life after work.