Planning for Serendipity

“Beware of missing chances; otherwise it may be altogether too late some day.”
— Franz Liszt

For most of my life, I had two styles of planning.

The first was trying to eliminate every possibility.

A clear path.

A rigid schedule.

Be here.

Go there.

Do this.

Leave by this time.

The idea was simple: if everything was planned, everything would be easier to manage.

The second approach was the complete opposite.

Just show up and hope for the best.

Neither one really worked.

One required hours—sometimes days—of research before I ever left the house.

The other left me wondering if I'd missed something important.

Did I spend enough time there?

Should I have gone somewhere else?

What didn't I even know to look for?

Had I been paying attention, I probably would have realized I was giving myself an impossible choice.

Either plan every detail until the adventure felt like another job...

Or plan almost nothing and spend the entire trip wondering whether I'd overlooked the best parts.

Both approaches created the same problem.

One replaced discovery with obligation.

The other replaced confidence with uncertainty.

This was where my tool worked best.

Not at either extreme.

In the gray area between rigid planning and blind spontaneity.

The place where I needed help navigating the questions I hadn't thought to ask yet.

Because that's what happens when Someday becomes the bandage.

You stop looking at the wound.

You stop asking why it's there.

Instead, you focus on the day the bandage will finally come off.

Someday.

The questions that matter don't disappear.

They simply go unasked.

And sometimes, it only takes the right question to start the journey.

...

It started with Seneca Rocks.

Well, not really.

It started with Fallout 76.

From a quick photo taken with friends.

Somehow, it appeared on my screen at the right time for me to start asking the right questions.

Where was Seneca Rocks in West Virginia?

Google it.

The image that came up only created more questions.

What's at the top?

How long would it take?

What's the closest airport?

I dove into the rabbit hole.

At the time, I had already been looking at property in the mountains and hills of surrounding states, so this was a good way to tackle two problems at once.

Explore a place I was curious about.

And learn more about the possibility of creating a different kind of future.

Google would work.

It would give me information.

It would give me possibilities.

And it would give me chaos to sort out.

So, I turned to ChatGPT.

I asked for a plan.

A low-cost trip for two travelers.

Seneca Rocks.

A property I was interested in buying in West Virginia.

And the Redwood forests of California.

I entered those destinations without expecting the shift I was about to enter.

Suddenly, the plan started forming.

Extremely slowly at first.

Because communication is a skill.

And I was learning how to communicate with a new kind of tool.

Mostly me.

But also ghosts in the machine.

Misunderstandings.

Wrong assumptions.

Unexpected answers.

A strange conversation between human curiosity and artificial intelligence.

But somewhere in that process, something changed.

The chaos was still there.

It was just becoming navigable.

To keep our flights tight enough for a good schedule, I needed days.

I only had so many.

I could have spent all the days in two spots.

There would have been nothing wrong with that.

But I had other thoughts.

Visiting the property.

Seeing sights with my son.

Learning more about the world.

Experiencing places instead of simply passing through them.

My curiosity never stops,

only my willingness to act on it.

So I kept asking more questions.

Where can I stay around there?

What else can I do there?

What are some interesting facts and historical sites?

A waterfall of answers.

A few questions, and suddenly I was setting up an itinerary.

Two weeks.

Multiple destinations.

A journey that had started from a random image in a video game.

With my new hybrid tool, I started cooking.

Hotels.

Flights.

Cars.

Is this the right date?

What else is around this place?

The answers would offer other questions.

The questions would create better plans.

The AI started recognizing some of my patterns, helping guide me when needed.

Other times, it would be a hindrance.

At times, I would find myself working forward five steps only to go back to the first.

But that's how we learn.

Failure shouldn't be a bandage either.

More like a salve.

A reminder of what not to do.

A lesson from the path that didn't work.

Because navigation isn't about never choosing the wrong direction.

It's about learning how to adjust when you do.