Optimize for Aliveness

For most of my adult life, I optimized spreadsheets.

Not literally — though there were plenty of those — but functionally. Where should we live? What's the return? What's efficient? What reduces risk?

Those were good questions. They built a life I'm proud of.

But they weren't the only questions.

And now, they're not the primary ones.

The Subtle Shift

Recently, someone asked me what I think will matter most when the novelty of this next phase settles.

My answer surprised me.

Energy.

Not tax efficiency. Not cost of living. Not even convenience.

Energy.

When I say energy, I mean:

• How I feel when I wake up in a place
• Whether I move more or less without forcing it
• Whether conversations feel expansive or routine
• Whether I'm curious, or just comfortable
• Whether I feel pulled outward — or lulled into autopilot

Some places are beautiful, but quiet your edge. Others are imperfect, but wake something up in you.

I've started to pay attention to that.

From Optimization to Aliveness

For years, I made decisions that made sense.

Now I'm trying to make decisions that feel aligned.

That doesn't mean abandoning discipline or practicality. It means not letting them dominate the conversation.

It means asking a different primary question:

Does this place, this decision, this structure make me feel more alive?

Because I'm starting to believe that aliveness is the real asset.

What Travel Has Shown Me

Over the past months, Shirley and I have spent time in places like Barcelona and across Africa.

We didn't just see them — we felt them.

Barcelona had a kind of hum: walkable, layered with history, full of movement and conversation.

Africa had something else entirely: scale, wildness, humility, presence.

In both places, we noticed something simple: we were more awake. More engaged. More curious. More there.

And when we left, we didn't say, "I'm glad we experienced that."

We said, "I want more of that."

That's data.

The Pull Test

At the same time, something else became clear.

We weren't pulled home.

Not because our home was wrong. It served its purpose beautifully. It held decades of life, family, and work.

But when we imagined returning, there wasn't anticipation. No "I can't wait to get back."

That absence of pull told us more than any analysis could.

And it led to a decision we've been circling for some time — one that still stretches me.

We're selling the house.

I haven't arrived at this quickly or easily. The gravity of it is real. But I've come to believe that staying put out of comfort rather than conviction is its own kind of risk.

Not a rejection of what was. A recognition of what's next.

The Danger of Premature Permanence

Five years ago, we seriously considered buying a condo on Maui.

It would have been a good decision — by most measures.

But I've told Shirley more than once recently: I'm glad we didn't.

Because it would have created gravity. We would have returned out of habit, out of justification, out of ownership.

And right now, what we feel most drawn to is not returning. It's exploring.

That experience taught me something important:

Designing Around Energy

As we look ahead, we've started to imagine what a more settled rhythm might look like someday.

Not one home. But a small number of places we return to.

When I think about what those places will have in common, it's not a checklist. It's a feeling.

Places where we say: "I can't wait to get back."

Not because they're easy. But because they activate something in us.

Maybe one place for mountains and movement. One for culture and depth. One for raw adventure.

Not redundancy. Complementarity.

A portfolio of energy.

What This Is (and Isn't)

This isn't about rejecting stability.

It's about redefining it.

Stability doesn't have to come from a fixed address.

It can come from health, relationships, discipline, financial security, a clear internal compass.

Those travel with you.

The New Filter

I still care about the practical questions.

But they've moved down the list.

Now, when I think about where to go, where to stay, what to build next, I find myself returning to the same questions I started with. They're simple. They're harder to fake than a spreadsheet. And they've become the primary filter.

Because at this stage of life, I'm less interested in maintaining what we built — and more interested in designing a life that continues to stretch me.

Closing Thought

I'm not trying to maximize comfort.

I'm not trying to minimize risk.

I'm not trying to accumulate experiences.

I'm trying to stay engaged. To stay curious. To stay capable. To stay connected.

If I get that right, everything else tends to follow.