⛰️ Trail & Error: Choosing Your Low Point

Welcome back to ⛰️ Trail & Error, your guide to building a life on your terms. 

Most people wait for rock bottom to happen to them.
But what if you could choose your turning point—before you start to spiral?

The path to freedom and fulfillment isn’t always smooth.
Sometimes it starts by getting radically honest, drawing a line in the sand, and deciding: This is the low point. And I’m building from here.

Let’s talk about what it means to write your comeback story—on purpose. 👇

Choosing Your Low Point

Every so often, you hit a moment that feels like a reckoning.

Not the kind that shows up with sirens and flashing lights.
But the quiet kind.
Where the weight of your choices suddenly lands—hard.
And you start to wonder if you’ve lost the thread.

For many of us who’ve stepped off the traditional career path—into coaching, consulting, or independent work—there comes a time when the ideals meet the pressure.

You realize you’ve been doing a lot of pondering, but not enough proving.
You’ve been holding space for others, but not creating momentum for yourself.
You’ve been trying to reassure people who love you that this will all work out—without quite believing it yourself.

I have had a few mornings like that, including one recently. Maybe you have too.

But here’s the reframe I’ve been working with lately:

What if I declare this moment the low point in my story?

What if, instead of waiting for things to get worse, I take control of the situation back by drawing a line and saying:

This is the bottom. And I’m building from here.

Then, instead of spiraling, I can start:

• Getting radically honest with myself

• Asking for help before things hit crisis

• Turning ideas into actions that build trust and income

• Recommitting to my deeper "why"—but with sharper execution

It doesn’t mean everything changes overnight. But this reframe made me feel a lot better. It allowed me to get back to action very quickly, after just a 20 minute journaling session while my kids were asleep.

Less floating. More foundation.

Less proving value through thoughtfulness alone, and more through tangible progress.

Because the goal isn’t just to feel free.
It’s to build a life where freedom, income, and alignment coexist.
One that doesn’t collapse under pressure—but flexes and adapts.

So if you’re in a dip right now—or if things are “fine,” but you feel off—maybe try this:

Draw the line. Choose the low point.

Then start building the comeback story you’ll be proud to tell.

That’s the trail I’m on right now.
And if you are too, I see you.

I’m here if you need anything, just hit reply and let me know what’s top of mind for you right now!

—Sean