Finding your second mountain

I came across something last week that I haven’t been able to stop thinking about: David Brooks’ idea of the Second Mountain.

He writes that we each live two lives:
the one we’re told to want, and the one we quietly crave.

On the first mountain, we follow the script.
We build the career.
We collect the achievements.
We learn how to be taken seriously.
We figure out the rules and we try to play them well.

We measure ourselves by the signals the world rewards.

And that works…
until it doesn’t.

Most people don’t talk about that moment, the moment at the top where, instead of feeling joy, you find yourself asking:

“Is this really it?”

For many, including myself, that realization isn’t a tidy epiphany.
It’s triggered by something unexpected: a scare, a loss, a rupture, a shift you didn’t see coming.

I had my own version of this in 2018.

It’s the valley, the place where the old story stops fitting but the new one hasn’t arrived yet.
The place where you can’t go back, but you don’t yet know how to go forward.

And…
it’s also where the second mountain becomes a possibility.

The second mountain is different.
The first mountain is about ambition, identity, proving yourself.
The second mountain is about meaning, alignment, and building a life that actually feels like yours.

You don’t climb it with hustle or force.
You don’t power your way up.
You listen your way up.

I see second-mountain moments all the time in my work:

• The leader who’s built an incredible career and suddenly wants something more human
• The founder craving depth instead of constant acceleration
• The parent rewriting their priorities after kids
• The high performer who wants to feel their life again, not just manage it

If you’re in that in-between space, where something inside you is tugging for a different kind of life, you’re not lost.

You’re just standing at the base of the second mountain.

And if you want support as you figure out what that climb could look like, I’m offering a complimentary one-hour coaching session.

No pressure.
Just space.
A quiet place to hear yourself again.

👉 Book a complimentary session: here

Here’s to the mountain that’s been waiting for you.

— Jenny

(and don't forget to checkout the below offer, which is bookable until the end of the year)

🎁 Limited Time: The Gift of Coaching: $495

Available to purchase through December 31, sessions can be used anytime in 2026

This 3-session coaching package is offered at $495 (regular price: $800), a special limited-time rate for the holiday season. It includes three 1:1 Zoom coaching sessions designed to help you (or someone you care about) build confidence, gain clarity, and create meaningful momentum heading into the new year.

Whether it’s a gift for yourself or someone in your life, this is a powerful way to start 2026 feeling supported and grounded.

If this resonates, or if someone came to mind as you were reading, feel free to reply directly to this email, forward this on, send me a DM, or book a 30-minute discovery call. I’m always happy to chat about whether coaching is the right fit.

Here’s to ending the year with intention and beginning the next with clarity.