Not Everything Good Can Be Optimized

Some of my favorite moments arrived while I was trying to do something else.

A small cafe discovered on the way somewhere. Meeting an old friend by accident. Finding a forgotten book. Hearing the right song at a time I had not planned for it.

These moments feel different from planned pleasures.

Planning creates an image before the experience arrives. The restaurant has reviews. The trip has photos. The event has expectations. Reality then has to compete with a version that already exists in the mind.

Serendipity has no preview.

That may be part of its pleasure.

Modern life is extremely good at reducing uncertainty. Maps choose routes. Reviews rank restaurants. Recommendation systems suggest books, music, films, and places based on what we already liked. Calendars protect time. Search removes wandering.

Most of this is useful.

But optimization has a hidden assumption: that the best experience is the one we can identify in advance.

I am not sure that is true.

Some value appears only because we did not know to look for it.

A recommendation system can help me find more of what resembles my preferences. It is less good at creating the strange encounter that changes those preferences.

The same is true of time.

A completely planned day may be efficient and satisfying. It also leaves very little surface area for interruption.

Of course, spontaneity can be romanticized. Getting lost is not always charming. An unplanned expense is still an expense. Surprise can be unpleasant.

The point is not to reject planning.

It is to notice that planning and discovery solve different problems.

Planning helps us reach known goods.

Openness gives unknown goods a chance to appear.

This is why I like leaving small amounts of life unresolved. Walk without choosing every stop. Enter the unfamiliar shop. Keep an hour without assigning it a task. Say yes occasionally when the invitation is interesting but inefficient.

Serendipity cannot be scheduled.

But conditions can be created in which it is still possible.

Maybe that is enough.

Not everything good in life can be optimized before we encounter it.