After the Long Weekend
For many of us, the Labour Day long weekend already feels like an eternity ago.
Between the back-to-school rush and Costco already stocking Halloween and Christmas gear on the shelves, summer slipped past without giving us a chance to catch our breath. Sitting with my wife recently, we found ourselves reflecting on how chaotic the last few months felt. Nothing truly bad happened. In fact, the good far outweighed the difficult. Yet there was this persistent, low-grade hum of uncertainty, a lack of control, and almost zero meaningful downtime.
If you asked whether I was happy this summer, I’d tell you I was neither happy nor unhappy. There were flashes of pure joy and moments of real misery, but day in and day out, things felt stagnant, moving forward, but devoid of deeper traction. Then Labour Day was here then gone.
Labour Day was originally conceived as a circuit breaker: a dedicated space to pause, establish boundaries, and reassess how our work connects to who we are. Instead, modern work culture has reduced it to a retail marker and a seasonal pivot point. It has been over a decade since my own work routine afforded that kind of deliberate, built-in reflection or time for detachment.
This isn’t another essay on preventing burnout or finding a mythical work-life balance. It’s about solving a deeper, more pervasive leadership puzzle: understanding what actually fulfills human beings at work.
Look back across your career, and you’ll likely find that what satisfied you at one stage completely failed at another. In my early twenties, I spent a few summers working as a whitewater river guide. It was stable, entertaining, deeply social, and just plain fun. For an 18-to-22-year-old mindset, it was total bliss. Whenever I sensed a colleague wasn’t enjoying it, it did not compute. How could you not love this?
Today, I watch leaders bump up against that exact same disconnect every single week. You see it in the remote work debate: some thrive in isolation and in the space of their choosing, others wither, and many swing between the two depending on the day and task. When perks, flexibility, or policy changes fail to satisfy a team, frustrated managers inevitably utter the familiar refrain: “They are never happy.”
We fall into the trap of assuming fulfillment is synonymous with positive emotion. We launch surface-level wellness initiatives designed to boost comfort and smile counts, expecting performance to follow. But pleasure and comfort can be fleeting, and it cannot carry the weight of sustained job fulfillment on its own.
If I returned to river guiding today, the novelty of the lifestyle would wear off within a couple of weeks, leaving me disengaged. Not simply because I’m older, but because the work wouldn't connect to a larger, enduring purpose.
For more than twenty years of my career, I traded comfort for purpose-driven work. Very little of the day-to-day grind was "fun". I didn't enjoy navigating dense bureaucracy, enforcing policy, or triaging student crises. Yet I went home deeply fulfilled because I knew the friction was shaping lives and strengthening an institution and our communities.
Naturally, contemporary leadership has leaned heavily into this second lever: purpose. We craft soaring mission statements and preach the "why". We actively and authentically engage. Yet leaders are frequently stunned when employees still burn out or detach. Why? Because not every role or every person finds fulfillment in being a crusader for an institutional mission.
Happiness isn't enough. Purpose isn't enough.
If I returned to the river today and wanted to find fulfillment, it wouldn't be from fun in the sun or a grand mission, it would be from the psychological engagement the work provoked. The river alters its shape every day. Water levels fluctuate, rapids mutate, and each crew of guests brings unpredictable human dynamics that force you to adapt in real time. From the outside, navigating that cold, turbulent water might not look like "happiness," but it demands cognitive stretch, constant problem-solving, and deep focus.
Creating an environment where people feel genuinely fulfilled isn't a fool's errand, it simply requires a richer framework. True work fulfillment relies on three distinct yet interconnected pillars: pleasure, meaning, and challenge. Because every individual weighs these elements differently depending on the task, their career stage, and their personal lives, effective leaders must take the time to truly understand their people. Rather than letting Labour Day pass as just another seasonal transition, we should reclaim its original spirit. Human beings are multi-dimensional, and we thrive best when our professional and personal lives continuously enrich each other.
The next time you catch yourself wondering why your team "is never happy," change the lens. Stop trying to manufacture happiness, and start building an environment that gives people the room, complexity, and perspective to truly expand.
This article was inspired by the work of Shigehiro Oishi, Professor of Psychology at the University of Chicago.
