Chapter 1: The Corporate Landscape for Generation X

Imagine being handed a treasure map leading to abundant resources in a far-off land. You are informed that the journey will be lengthy—spanning decades—but that you’ll be generously rewarded for your perseverance. This enticing proposition was what Generation X was promised for many years. Now, as we find ourselves in our 40s and 50s, it’s become clear that the roadmap we received for achieving corporate success has proven largely ineffective, leaving many Gen Xers feeling unprepared for retirement yet exhausted from years in the corporate grind.

Generation X includes individuals born from 1965 to 1980, making them between 41 and 56 years old as of 2021. So what went wrong for this “overlooked” generation that pursued higher education in the hope of landing stable office jobs with solid benefits? The answer, succinctly put, is technology—particularly the rise of the World Wide Web and the Dotcom boom, which heralded a new era for powerful tech and social media enterprises. We found ourselves caught between the traditional corporate landscape and the innovative new world.

Raised by Baby Boomers—those born between 1946 and 1964—Generation X was conditioned to believe that a lengthy tenure with a single company would lead to a comfortable retirement. My father, for example, received a beautiful Howard Miller grandfather clock from his bank after working there for over four decades.

Being influenced by the Boomers, we were taught to excel academically, with the understanding that college was the ticket to a rewarding office position. Today, the notion of “being smart enough” to attend college seems almost outdated, especially as an entire generation has learned to harness technology to achieve success outside traditional corporate frameworks.

I recall my first corporate internship, where I was informed of the office hierarchy: proximity to the corner office signified importance. Window offices overlooking the exterior were more coveted than those facing the building’s interior, so new managers often received the less desirable spots.

As members of Generation X, we were expected to be patient, respect authority, save diligently for retirement, start families, and purchase homes in suburban areas. Like many of my peers, I attempted to adhere to this traditional Boomer roadmap. However, when it was finally our turn to ascend to leadership roles, we found the path drastically altered, with the promised rewards appearing tarnished or entirely absent.

The conversation about office hierarchies faded as the corporate world shifted toward open floor plans, promoting collaboration and equal validation of ideas. I often jested that my largest office was merely a vacant room during my internship. As I advanced in my career, my workspaces became increasingly smaller and more open.

Ironically, two decades later, while many Gen Xers pursued office positions, the real prize turned out to be the ability to work from home—a trend that gained significant traction even before the pandemic. Now, these same individuals are discovering that remote work presents its own challenges, requiring an entirely new skill set.

The first video explains how Generation Z is influencing the future of corporate America, showcasing their unique perspectives and approaches.

Chapter 2: The Evolution of Work and Compensation

In the wake of COVID-19, the landscape of remote work has transformed dramatically.

The concept of salary has also shifted over the years. I recall discussions in my twenties about receiving 15% raises with promotions, but now, such increases have dwindled to below 10% for many similar roles. While technology has made operations more efficient and profitable, these gains have not consistently translated into higher wages for employees.

Generation X has had to report to Baby Boomer managers even as Millennials entered the workforce—the very group we were expected to lead. We were conditioned to view employment as a privilege, placing immense value on work ethic. I vividly remember receiving emails from my Boomer manager while she was hospitalized, contrasted with a Millennial team member who requested additional time off on her first day back from vacation. This Millennial seemed unfazed by the optics of her prioritizing personal time after just returning from a break.

With each new generation, a gap emerges in how they engage with society. Traditional complaints about younger generations have persisted, but the technological revolution has widened this divide significantly. With technology comes increased freedom and insights into leading a more fulfilling life at work and beyond. Social media has introduced diverse philosophies, careers, and lifestyles that past generations could scarcely imagine.

Millennials, in particular, have consciously or unconsciously chosen not to center their lives around climbing the corporate ladder. They recognize that technology has opened numerous pathways to success and income generation. Job hunting has become markedly more efficient thanks to platforms like LinkedIn and Indeed—far removed from how people discovered job opportunities in the 70s and 80s.

For Generation X, the process of acquiring knowledge was often manual and time-consuming. It was entirely possible to reach adulthood without even knowing about certain career options. In this sense, ignorance was somewhat blissful. Generation X resembled Neo before he chose to take the red pill.

The second video discusses the reality of corporate layoffs and how Millennials are navigating their careers in a precarious economic environment.

Millennials, on the other hand, resemble those who were born free in The Matrix. They possess significantly more resources and knowledge due to advancements in technology. They have access to a superior roadmap—a high-definition one at that.

Generation X has often been told, “Life isn’t fair; this is the minimum wage; these are the jobs available—deal with it.” Millennials have responded with determination, asserting, “We will create equity, mobilize quickly for better pay, and explore diverse income sources if necessary.”

Where Boomers once relied on pensions and social security for retirement security, Generation X has been cautioned about potential inadequacies in these systems. Millennials refuse to sit idly and wait to see how retirement unfolds. They are bold and are actively creating multiple income streams—fully embracing the potential of cryptocurrency, for example.

Generation X finds itself caught in the middle, weighing whether to adhere to traditional investment strategies advocated by their parents or to follow the more progressive paths of younger generations, fearing being left behind. Imagine if Bitcoin were to soar to $100,000 USD per coin!