Keep Singing

On a recent trip to New York, we saw Hadestown.

Near the end of the show comes a line that has stayed with me:

“It’s an old song… but we sing it again.”

It’s tempting to hear that line as resignation — a shrug at inevitability. The story repeats, the ending is known, and still we go through the motions.

But Hadestown isn’t a story about inevitability.

It’s a story about hope practiced without guarantees.

The song is sung again not because success is assured, but because stopping would guarantee failure. That distinction matters in art, in life, and in business.

This Is Not About Positive Thinking

This is not an argument for optimism as cheerfulness.

It’s not advice to “stay positive.”

It’s not denial of risk, loss, or disappointment.

This is a philosophy about how humans engage uncertainty.

We’re not talking about what to think.

We’re talking about how to think when outcomes are uncertain and effort must be repeated.

Optimism, Persistence, and Probability

Optimism and pessimism are often treated as personality traits: fixed dispositions that color how people see the world. In practice, they function more powerfully as patterns of engagement.

Optimism increases the likelihood that a person will persist, will try again, stay in the game, re-enter the cycle after partial failure.

Pessimism accelerates exit. It encourages premature closure, mistaking early variance or discomfort for a final verdict.

This matters because probability doesn’t operate on single moments.

It operates across series.

A single attempt may have low odds of success. Persistence does not improve the odds of any one attempt. But repeated attempts, assuming they don’t permanently degrade the system, increase the probability of eventual success.

Persistence doesn’t change the odds of failure on any attempt; it reduces the probability that failure is the final outcome.

The only move that collapses probability to zero is exit.

Acting Before Certainty

This is the same logic behind acting at “70%,” committing to action before certainty, moving when you have enough information to proceed, knowing you will learn the rest by doing.

70% thinking isn’t reckless. It assumes imperfection, expects adjustment, and treats early results as information rather than verdicts.

Optimism gets us into motion.

Learning keeps us honest.

Endurance Pays for Persistence

Persistence, however, is not free.

Trying again costs something: energy, capital, morale, time, identity.

Persistence is behavioral.

Endurance is economic.

Endurance is the capacity to absorb friction without impairing future action. It is recovery, slack, margin, and replenishment.

This is as true for organizations as it is for people.

Burnout is rarely a motivation problem. It’s an endurance problem: a system consuming resources faster than it replenishes them.

A Necessary Caveat

Pessimism is not irrational. In many situations it is the most logical stance, particularly when failure is irreversible, resources are scarce, or the system cannot safely absorb error.

The point is not that pessimism is wrong, but that it becomes costly when it closes the door too early in situations where learning, adjustment, and re-entry are still possible.

Why This Matters in Business

Many strategies don’t fail because they’re wrong. They fail because organizations exit too early.

Markets, relationships, transformations, and reputations are series efforts, not one-and-done endeavors.

The critical leadership questions are not:

Is this uncomfortable?

Did the first attempt work?

But:

Is this a series or a one-and-done effort?

Have we funded endurance long enough for probability to converge?

Are we exiting because of evidence, or exhaustion?

Satisfaction, Memory, and What We Choose to Remember

Optimism and pessimism also shape how experiences are remembered, not because optimists feel better in the moment, but because they are less likely to let a single difficult episode stand in for the whole.

Satisfaction isn’t about denying friction. It’s about proportion.

A Philosophy, Not a Formula

This framework offers no guarantees. It doesn’t promise success, happiness, or winning outcomes.

What it offers is intellectual honesty about how uncertainty actually works when humans are part of the system.

Why We Sing the Song Again

In Hadestown, the ending doesn’t change. The loss is real. And still, the song is sung again.

That is not naïve optimism.

That is disciplined hope.

Probability offers no certainty.

Keep Singing anyway.