What is your grounding vision?

Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.

I can always wait tables

There was a time not long ago when I had very little safety net. Minimal savings. Some credit card debt from my divorce. And a startup that was on the rocks.

During that time, one thought kept me sane:

One of the happiest seasons of my life was waiting tables in Chicago.

I’d sleep in, take a run, read a book, then wander into work around 4 p.m. After closing down the restaurant, I’d enjoy late-night hangouts with friends. It was simple. And I was happy.

That memory reminded me: I didn’t need much to feel joy. That kept me afloat mentally during that difficult financial season.

Life today is different.

I live in my dream home by the beach. I have savings, investments, and I earn several multiples of what I did then.

But the fears? They still come.

What if it all goes away?

What if the market turns?

Savings vanish. A health crisis strikes. Something big changes.

It’s human to have these fears. To live is to be aware that everything is impermanent.

Today, I find grounding in a new vision:

I need my family.

I need nature.

I need a few close friends.

I need meaningful work.

If I lived in a small house in a small town and coached a small group of people—I’d be good. Really good.

I’m sharing this because I wonder: What is your grounding vision?

As founders, investors, creatives, and coaches, we are vulnerable to fear spirals.

A lost customer. A failed raise. A co-founder's departure.

Suddenly, the fear brain kicks in: this is the beginning of the end.

I hear it in my coaching calls every week.

And not just from founders, also from investors, therapists, designers, craftspeople.

Especially now, with so many roles being reshaped by AI.

So let me ask: What is your worst-case-scenario life—and would it actually be enough?

What truly matters that can’t be taken from you?

Take 10 minutes. Write it down.

Even better, share it with someone you trust.

Let them witness your fears—and your vision.

That kind of reflection can be profoundly freeing.

It unlocks courage. Creativity. Peace.

A few years ago, on one of my hardest days, my coach asked:

“If it all fell apart, what would you do to take care of your family?”

I cracked a smile. “I’d go back to waiting tables.”

He smiled back. And something in me relaxed.

I had it. I could rebuild. I could be okay.

Wishing you that same sense of peace. Wishing you the awareness of what you already have that is not at risk.

Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.

If I can be of assistance in your journey in any way, please reach out.

With love from LA,

Matt

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