Knowing When to Get Off the Wrong Train: The Courage to Pivot in Your Career

Administrative Profession Culture & Events Goal Setting July 25, 2025

A Japanese legend says:
“If you get on the wrong train, get off at the nearest station; the longer it takes you to get off, the more expensive the return trip will be.”

Sometimes the bravest thing you can do is admit you’re on the wrong train.

In our profession, and in life, we sometimes cling to roles, relationships, or routines that no longer serve us.
Because we’ve already invested time.
Because we don’t want to let someone down.
Because change is uncomfortable.

But staying on the wrong track doesn’t make it right. It just makes the journey longer, harder, and more costly to recover from.

This is your permission slip:
To reassess.
To pivot.
To protect your peace.
To change direction if where you’re headed isn’t aligned with where you want to go.

Your value is not tied to how long you endure something that isn’t working.
It’s tied to your courage to choose better – for yourself, and for your future.

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If your assistant always agrees with you, you don’t have a partner.
You have a mirror.

And a mirror can’t warn you when you’re about to walk off a cliff.

Here’s the thing:

• The best assistants sense-check decisions and ask why.
• They push back on processes that waste time.
• They flag risks you don’t want to see.

That isn’t insubordination.
That’s what partnership looks like.

Many executives still confuse silence with loyalty. It isn’t.
Silence is fear. And fear kills performance.

If you’ve hired well, you already have someone who sees what you don’t. When they speak up, they’re not undermining you. They’re protecting you. That’s their job.

I tell every assistant I train: your role is not to be afraid of your executive, but to be afraid for them.

So the next time your assistant challenges you, pause before shutting them down. Ask yourself: What am I missing?

Because here’s the paradox: the voice you silence might be the very one that saves you.
The smartest voice in the room isn’t always the loudest.
Sometimes, it’s the one you’re not ready to hear.

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