When Two Things Are True at the Same Time

After writing about failure versus fit, (Link to full article HERE) we began reflecting about the stories we tell ourselves when work becomes difficult. Often, we need someone to be wrong for our experience to make sense. This follow-up piece looks at what happens when we resist that pull and hold more than one truth at once.

One of the most destabilizing moments at work is realizing this:

My experience is real, AND... it may not be the whole truth.

I can believe, with conviction, that my boss is terrible.

I can have examples.
Receipts.
Moments that left me feeling dismissed, undermined, or exhausted.

And at the same time, and this is the part we resist, that same boss might be an effective leader. Well-regarded. Even deeply valued by others.

Both things can be true.

The Discomfort of Holding Tension

Most of us are trained, consciously or not, to collapse complexity.

We like clean stories:

• Good leader / bad leader
• Healthy culture / toxic culture
• Right / wrong
• Capable / incompetent

They help us make sense of pain. They give us something solid to stand on when work becomes difficult.

But leadership and systems don’t actually work that way.

Your boss can be:

• Highly effective with one team
• Poorly attuned to another
• Brilliant in crisis
• Awful with emotional nuance
• Aligned with the organization’s values
• Completely misaligned with yours

None of this invalidates your experience.

It contextualizes it.

Experience Is Not the Same as Character Judgment

Here’s where things often go sideways.

When we’re struggling, we don’t just say:

“This isn’t working for me.”

We often slide into:

“This person is bad at what they do.”

Sometimes that’s true.

But often, it’s something more subtle and harder to name:

• A mismatch of expectations
• Different definitions of leadership
• A cultural norm we can’t or won’t adapt to
• Power dynamics that amplify friction
• A system that rewards behaviours that cost us something personally

When those conditions are present, it can feel personal, even when it isn’t.

Fit Is a Relational Concept

This connects back to the idea that fit is not a moral judgment.

Fit is relational.
Contextual.
Systemic.

A leader who thrives in one environment may struggle in another.
An employee who feels constantly misunderstood in one role may be deeply valued elsewhere.

That doesn’t make either party wrong.

It means the relationship, between person, role, culture, and system, isn’t working.

And relationships, not individuals, are often where things break down.

Why This Is So Hard to Accept

Holding “two things at once” is emotionally demanding.

It asks us to:

• Let go of simple villains
• Accept that our pain doesn’t require someone else to be bad
• Grieve without blaming
• Leave without needing to be right

That’s not nothing.

Especially when we’ve been hurt.

Especially when the cost has been high.

A More Spacious Question

Instead of asking:

“Who’s right here?”

A more useful question might be:

“What is this system making possible (and impossible) for each of us?”

Or:

“What does this environment reward, and what does it quietly punish?”

These questions don’t erase harm.
They don’t excuse poor behaviour.
And they don’t ask you to gaslight yourself.

They simply widen the lens.

Letting Complexity Be Kind

Sometimes, recognizing that two things can be true at once is the most compassionate move available.

Compassion for yourself, because your experience matters.
Compassion for others, because no one is only the version you encountered.

And compassion for the reality that work is a human system, full of imperfect fits, partial truths, and unresolved tensions.

You don’t have to decide who’s good or bad to decide what’s right for you.

And you don’t have to flatten the story to move on.