Do We Need to Be Miserable to Connect?

Jan 6

Do we need to be miserable to belong?

I’ve been sitting with this question lately, especially after noticing how carefully many of us manage our happiness around others.

Do we see happiness as a mask?
As denial?
As a sign that someone’s life must be so perfect they couldn’t possibly relate?

Does happiness block connection?

What research suggests is that it’s not the emotion of happiness that creates distance, it’s how we express it, and how much we monitor ourselves while doing so.

That’s where my curiosity has landed: self-monitoring.

How often do we quietly ask:

If they aren’t happy, will my honesty feel insensitive?
Will it highlight something they’re struggling with?
Does happiness tempt fate, inviting misfortune, illness, or loss?

Can we claim where we are, happy, steady, content, without managing how it lands?

Or does happiness need to be a quiet joie de vivre; felt, but not spoken?

And if we can’t name steadiness or contentment out loud, how do we expect to build energized teams, psychologically safe workplaces, or cultures where people feel permission to thrive?

Happiness, Privilege, and the Fear of Being Misunderstood

I felt this tension recently when I shared a post about slowing down and resting during the holiday season.

Before hitting “publish,” I hesitated.

Will this sound like privilege?
Will it feel tone-deaf?

Which led me to a deeper question: Is happiness purely circumstantial or is it also a choice?

I think the answer depends on how we define it.

For me, happiness isn’t about everything going right.
It’s a state of being satisfied.

Not chasing more.
Not comparing.
Feeling steady in where I am, who I’m with, and how I spend my time.

It’s knowing I may not meet conventional standards of “excellence” in every area—career, health, relationships, spirituality—and being okay with that.

And rest, for me, isn’t just time off.

It’s letting go of what’s expected of me.
Allowing my mind to move from output to imagination.
From urgency to play.
No clock. No finish line.

What This Has to Do With Leadership

When I worked full-time as a leader, happiness and rest were not handed to me.

They were active choices.

In many ways, the system is designed to keep us going, draining just enough while offering a paycheque every two weeks to sustain the cycle.

I remember early in my career, complaining that I wasn’t being recognized for my hard work. My boss, known for her bluntness, looked at me and said:

“That’s what your paycheque is for.”

At the time, I was taken aback.
Today, I see the truth in it.

When leaders rely on external validation as a measure of worth, they stay locked in self-monitoring; constantly scanning for approval, editing their emotional expression, adjusting themselves to feel acceptable.

And leadership rooted in self-monitoring is exhausting.

This isn’t about toxic positivity.
It’s about regulated leadership.

Regulated leadership is the ability to stay grounded in your internal state (your values, emotions, and sense of enoughness) without outsourcing emotional stability to how others respond or what the future guarantees.

When leaders are regulated, they don’t need to mute their happiness, inflate their struggle, or perform resilience to belong. They can hold complexity and steadiness at the same time.

This is where self-trust begins to replace self-monitoring.

And when that shift happens, leaders create environments where others don’t feel pressure to perform their emotions either—where authenticity, psychological safety, and sustainable engagement become possible.