Sleepless Nights

Before diving into the heart of this article, let me share a quick update on last week’s piece, "Fun and the Fellas." My son actually read it, a feat accomplished thanks to his sister's gentle—or perhaps relentless—prompting. His feedback? A single text pointing out a crucial error: I’d called his adventures "side treks" when they are, in fact, "side quests." He followed this correction with a grinning emoji, which I’ve decided to interpret as a sign of his approval for the article, rather than just a punctuation mark on my mistake.

Since trading the daily grind of full-time employment for a new chapter, one major change has been the quality of my sleep. The frequency of "sleepless nights" has plummeted. Gone are the 3 AM wake-ups spent stewing over some intractable work problem. Now, when those nights happen, they feel like a glaring anomaly, forcing me to truly confront the root cause of the lost sleep. This reflection has naturally led to a much deeper, retrospective look at why sleepless nights were such a constant companion during my career. I’ve realized the work-induced insomnia fell neatly into two categories: "Rent-Free" and "Rent-Paid."

Rent-Free:

I’m sure you’re familiar with the phrase "living rent-free in your head." It’s that maddening state where a frustrating person, topic, or experience becomes an obsessive, persistent loop in your thoughts, offering zero value in return. My career was peppered with these episodes, often leading to a physical "presence" at work and home but a complete mental absence, ultimately triggering bouts of insomnia.

But here’s the interesting part: looking back over my entire 30+ year professional career, this obsessive thinking wasn't always the norm. Early in my career, the work was arguably far more stressful—dealing with crises like sexual assaults, violence, and mental health emergencies involving students in residence. Yet, I don’t recall insomnia being a major issue. Two factors, I believe, kept sleepless nights at bay.

First, I wasn’t fighting those battles alone. I was always surrounded by colleagues grappling with the same challenges. Whether their situation was better or worse than mine, we shared a common, unspoken understanding of the difficulty of the work. This shared experience, though not intentionally therapeutic, provided a sense of safety and quiet for my mind.

Second, I was, frankly, emotionally immature. Empathy isn't my natural default, and in those early years, it was easy to create a professional distance from the problems of others. That, combined with a robust ego, created a kind of emotional armour, making it rare for work challenges to burrow obsessively into my mind.

As I climbed the ladder and embraced new roles, focusing more on good leadership, the frequency of those "rent-free" mental takeovers grew. The work wasn't necessarily harder—in some cases, it was far less impactful or stressful. So, what changed?

First, the isolation increased. Moving into senior roles meant fewer people truly understood the challenges I faced. Those who did were often siloed, both by organizational structure and what I now call "leadership arrogance." Hierarchy inherently limits the number of individuals who can genuinely grasp the rigours of senior leadership. This isolation is compounded by a false sense of overconfidence that often comes with titles. As you progress from manager to director to executive, we often mistakenly inflate our own abilities. This arrogance widens the psychological gap between you and your team. When that gap becomes too large, the brain becomes fertile ground for negative, obsessive thinking that helps no one.

The second factor was a shift in focus. As leading others and prioritizing their success became my main objective, I lost the ability to maintain emotional separation. My natural emotional empathy didn't suddenly grow, but my cognitive empathy and compassion for those in my influence certainly did. The combined force of structural isolation and genuine emotional concern resulted in countless sleepless nights and an unfortunate, unintended emotional dissociation from family and friends. Work consumed my mind, day and night.

Rent-Paying:

Ironically, this period of frequent sleeplessness was also a time of significant personal and professional achievement. My teams and I were performing at peak levels—connected, engaged, innovative, and compassionate. Work was genuinely joyful. But the success didn't alleviate the psychological burden. I knew my approach wasn't sustainable and needed a radical change. My goal became transforming "rent-free" thoughts into "rent-paying" thoughts, all without sacrificing my professional ambitions or my commitment to leadership excellence.

In the final third of my full-time career, I implemented changes that drastically improved my well-being. I had to confront and reduce the negative effects of organizational distance and my own leadership arrogance. Throughout my career, I felt a deep responsibility to challenge and disrupt the status quo to achieve the best outcomes. This approach, as you can imagine, generated immense tension, which, in my sleepless phase, manifested as "rent-free" thinking. I'd obsess over the lack of candid engagement, the resistance to change, and other factors completely outside my control.

Turning these experiences "rent-paying" required reframing my style without abandoning my nature. I realized that reducing organizational distance was fully within my control. My approach wasn't to avoid disruption; it was to radically refocus my energy. I chose to pour my relational efforts into those I could influence, those who truly needed me, those who also wanted change, and those who would directly benefit from the work. This wasn’t about abandoning other relationships; it was about investing my energy for maximum, co-created impact. I intentionally ignored the hierarchical approach to success. Those obsessed with the chain of command simply fell out of my active mental space, and "rent-free" began to shift toward "rent-paying." Collective success became my leadership style, not just a positive byproduct. The people, topics, and frustrations that once consumed me because I was trying to change them dissolved from my consciousness. I knew they existed, but I successfully moved them aside to make space for alignment, opportunity, and engagement. While I didn't ace this new approach every time, I got significantly better at pushing past the psychological weight and actually doing something.

This transition was also marked by an increase in transparency and authenticity. I didn't realize it then, but I was actively dismantling my leadership arrogance. Showing more of myself meant embracing vulnerability, and creating a safe space for my team to do the same was paramount. This combination helped me see my flaws and limits clearly, allowing me to act with greater purpose to benefit others. My ego is a beast I wrestle with constantly; it's still alive and kicking, landing me in hot water more often than I'd like, but now, at least, I enter the fray with my eyes open and a desire to adapt and accept fault.

I could have abandoned my commitment to care and compassion to sleep better, but I chose instead to put those acts into a new, "rent-paying" context. Earlier in my career, I helped people and hoped for some form of reciprocity. When that return didn't come or meet my expectations, the "rent-free" thinking flared up. I now understand that my acts of care are not about others; they are about me. I do them because I feel better, and doing so with zero expectation of a return is what transforms "rent-free" into "rent-paying" thought. When someone in my sphere is in need, my mental energy goes into actionable steps: How can I help? What can I do differently? I didn’t revert to my early-career emotional distance; I became more realistic about demonstrating concern and changed how I measured its impact. Empathetic behaviours became a vital source of fuel, driving me to seek perspectives and experiences that were productively uncomfortable. My mental energy shifted from negative, obsessive paralysis to positive, inclusive, and actionable thinking.

There are powerful lessons I wish I’d learned sooner. First, as you advance, actively fight the structural and positional isolation that comes with promotion. Stay connected and deeply committed to the people who are doing the real work of the organization. Second, empathy and compassion are true leadership superpowers only if they are given freely, without expectation of return; if you show vulnerability; and if you create a culture where people can bring their whole selves to work.

Finally, if I were to lead a team again, my first question would be: What work-related people, topics, or experiences are costing you sleep? Leaders have an absolute obligation to reduce, prevent, and eliminate "rent-free" thinking in their teams. Showing you care opens up easy avenues to help people convert those draining thoughts into "rent-paying" ones. I’m not immune to a sleepless night, but I am infinitely better at making that conversion. It has made me happier, profoundly benefited my teams, and hasn't negatively impacted success one bit.