Mandatory Fun Day

I’ve worked for many different companies over the years, and I’ve experienced a wide range of workplace cultures and traditions. I feel grateful for many of the teams I’ve been part of, but I’ve also noticed how much companies struggle with one particular thing: employee engagement.

Some companies do nothing at all.
Some companies do a lot—sometimes almost too much.
And a few, in my opinion, strike the right balance of engagement, culture, and benefits.

But here’s what I believe is more important than any of that.

Most people today don’t celebrate unless their company prompts them to.

Think about how often managers take teams out to lunch—but only if it’s company-paid. My husband once had a manager who regularly treated his team to lunch out of his own pocket. That small difference made it feel genuine, personal, and intentional—not transactional.

When everything is paid for, planned, and expected, it creates a lack of emotional investment. People often don’t care more when they’re incentivized to care; they care when something actually means something.

I’ve also noticed a generational gap in expectations. Older generations often expected little from their employers, while younger generations tend to expect generosity, work-life balance, and workplace perks. In response, many companies now plan “mandatory fun days”—events designed to bring coworkers together and build culture.

Sometimes they work.
But more often, I believe they create experiences rather than real connections.

These events are planned.
They’re paid for.
And they’re expected.

That makes them feel anything but organic.

Worse, they sometimes send a subtle message: You don’t need to step up—because the company will handle it for you. Over time, that removes personal responsibility and intention from leadership and teams.

I don’t believe big events create better culture. If anything, the older I get, the more I realize that it’s the small, immaterial things that truly matter.

A thoughtful handwritten thank-you card—not one that’s templated or rubber-stamped.
An impromptu conversation.
A spontaneous lunch to celebrate something meaningful in someone’s life.

Recently, a new coworker said to me, “I only go out with people because it’s company-paid and I have to.” That comment made me genuinely sad. It showed a lack of appreciation and intention—two things I believe are essential to a healthy workplace.

If you’re a manager, learn how to show appreciation with intention.
Don’t create mandatory fun days just because you feel obligated to.
Create a simple philosophy around stewardship—of people and of company resources—especially if your organization doesn’t have deep pockets or large expense accounts.

Culture isn’t built through obligation.
It’s built through care.