Kristen Ripmaster standing confidently in a blue dress and white blazer, representing a bold career shift and stepping into personal power

When Comfort Becomes the Cage: What I’d Tell My Pre-Mom, Pre-CEO Self

July 10, 20252 min read

When Comfort Becomes the Cage: What I’d Tell My Pre-Mom, Pre-CEO Self

I was recently asked during a speaking panel, “What advice would you give your pre-mom self?”

And wow—did the answers pour out of me.

At the top of the list? I would tell her this:
Take more chances. Say yes to new roles. Explore new companies. Do it more often.

Why? Because staying too comfortable can mean staying stagnant.
Because working under different leadership sharpens your skills.
Because every bold move can come with a bold raise—both in salary and in confidence.

And yes, I know the loyalty thing. I gave 20 years to the same company. Climbed the ladder. Landed in the C-suite. But that comfort came at a cost.

The truth is: tenure doesn’t equal security.

I’ve seen it firsthand—
The 2008 recession: long-time employees let go.
The pandemic: loyalty didn’t save anyone.
Entire companies folded, with no warning and no parachute.

That’s when it hit me.
This is your life. Your career. Your growth.
You are not required to stay where you no longer grow, no matter how “good” it looks on paper.

Yes—even if you’re climbing the ladder.
Because what’s the point of climbing if it’s the wrong building?

You don’t owe your company loyalty at the expense of your dreams.
You owe yourself a career—and a life—that challenges you, excites you, and reminds you what you're made of.

So if your Sundays feel heavy…
If you’re outgrowing your role or constantly wondering what’s next
That’s not just a rough patch. That’s your intuition knocking.

And no, I’m not telling you to blow up your life like I did (I literally walked away from a 20-year career without a master plan). But I am telling you this:
Listen to that voice inside.
Get honest with yourself.
Make the move—even if it’s small, messy, or unclear at first.

Because growth never lives in comfort.
And regret? It loves to linger in places where we stayed too long.

You get one life. One shot to build something meaningful.
So take the step—even if it’s wobbly.
Bet on yourself—even if it scares you.

And if you need someone in your corner for that journey? I’m here.

Let’s rewrite your story—on your terms.

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