Chapter 1: A Glimpse into Rick's Journey

The clock struck 9 PM as my former CIO, Richard—whom we call Rick—wrapped up a call with the headquarters in France. He provided them with the necessary updates while absorbing the stress they had transferred to him. Little did we know, Rick was grappling with more than just his job; he was battling his own emotions.

That night took on a significant meaning. Rather than enjoying dinner, Rick resorted to instant noodles at his desk, inundated with a flood of emails, all while a relentless thunderstorm raged outside. He felt overwhelmed, both angry and emotional.

Rick ultimately decided to leave that evening.

"I faced a storm of emotions and a false sense of financial security," he later recounted to me.

I wasn't aware of Rick's struggles until two years later when he reached out via LinkedIn. Initially, I assumed he wanted to recruit me for a new, enticing position. Yes, he remembered me, but unfortunately, he was seeking a job rather than offering one.

I found myself in a tricky position; I had nothing that would suit his aspirations. Even if I did, Rick remained deeply passionate about IT operations, while I had moved on to software sales, where I found greater satisfaction.

Despite our different paths, we agreed to meet, curious about what had unfolded in his life since his self-proclaimed retirement.

"I left my job because the pressures became too much. My workload increased significantly, and my budget was cut by 60%, all while I was expected to initiate new projects. It was too much,” he admitted.

This is the harsh reality of IT operations. The pressure to innovate is immense, but austerity measures can make it feel impossible. Imagine being tasked with constructing a bungalow while only being given a penknife—that was Rick's daily struggle.

He was caught in a relentless squeeze from both ends, and it wore him down.

“I will never forget that night. My emotions overwhelmed me. I checked my brokerage account and saw a significant increase in my portfolio. I felt financially secure enough to quit, so I did. I thought I’d be okay.”

That was in 2019, just before the COVID-19 pandemic swept through Singapore in early 2020.

Rick soon came to a stark realization: his management skills held little value outside of the workplace.

This realization hit him hard. He had believed that his expertise would be in demand, but as he sought to leverage his skills, he found that he had underestimated the market's shift towards artificial intelligence, Python, and analytics.

Rick's management background was becoming obsolete, and he faced rejection from three universities where he had applied to teach Information Systems Management and Project Management.

Compounding his woes, his cash reserves began to dwindle. Though his investment portfolio had initially given him the confidence to resign, it was not sustaining him in this new phase of life.

“My tech stocks aren’t providing dividends, and I’m forced to liquidate my investments to generate cash. I feel foolish for drawing down my reserves before turning 60!” he lamented.

This was during the tumultuous period of 2020 to 2021.

It's crucial to note that major companies like Meta and Alphabet only began issuing dividends recently, leaving Rick with unrealized gains rather than cash flow.

As his reserves evaporated, he started selling his stocks bit by bit, feeling the weight of his financial decisions bear down on him.

Rick spent five years trying to navigate the entrepreneurial landscape, searching for viable business ventures that could turn a profit. It wasn’t straightforward; he was uncertain about what direction to take and ultimately lost $40,000 in the process.

With mounting financial pressures from car loans and mortgage payments, he decided to return to the corporate world.

Time was not on his side.

The Conclusion: Lessons from Rick's Experience

Is there a silver lining in Rick's tale? Absolutely.

It serves as a reminder that when we let negative emotions overwhelm us, our decision-making can become clouded, leading us to make regrettable choices.

Rick's experience illustrates that it’s essential to think carefully before acting, especially in emotionally charged situations.

If you found this story enlightening, consider subscribing for more insights! And if you're feeling generous, a cup of black coffee would be much appreciated!

Chapter 2: Reflections on Retirement

The video titled "My Company Fired Me, But After 49 Calls, the CEO Finally Asked Who I Am. Here's What Happened..." provides a compelling narrative that resonates with Rick's experience and the broader implications of career transitions.