Reflecting on Work: Was It Worth Doing?

Editor's Note: This essay forms part of the Cultivated canon — a body of work exploring how ideas become valuable in organisations. It focuses on a recurring failure in modern work: not a lack of effort, but a lack of reflection on whether that effort was ever worth making.

Reflecting on Work: Was It Worth Doing?

Having spent decades inside organisations, I’ve noticed a quietly destructive pattern.

An extraordinary amount of work is started — and just as quietly abandoned.

Change programmes stall halfway through. Tools are rolled out, trained on, and slowly ignored. Workshops generate energy that evaporates within weeks. Slide decks are created, shared once, and never opened again. Teams stay busy, but value remains elusive.

This is not just a financial problem.

It is a human one.

People want their work to matter. They want to see effort translate into progress, learning, or something tangible that improves the organisation. When work disappears without explanation, something erodes — trust, motivation, hope and belief that effort is worth giving.

So why does this keep happening?

And more importantly, how do we prevent it?

Three questions worth stealing

The writer Henry James once proposed three questions for judging a work of art:

What was the artist trying to achieve?
Did they succeed?
Was it worth doing?

These questions translate remarkably well to organisational life.

And yet, they are rarely asked.

When initiatives end — whether they “succeed” or quietly fade — organisations tend to move on quickly. Reflection is skipped. Inquiry is avoided. Sometimes this is due to time pressure. Sometimes it is embarrassment. Often, it is simply habit.

But without reflection, work, and mistakes, do not just compound. They also accumulate.

The most dangerous question we don’t ask

Consider a familiar example: introducing a new work management tool.

Time is spent evaluating options. Licences are purchased. Training sessions are run. Teams are asked to adapt how they work. Other priorities are displaced.

Months later, the tool is either embedded, partially used, or effectively abandoned.

At that point, the most important question is not whether the tool was “good”.

It is simpler, and more uncomfortable:

Was it worth doing?

Not in hindsight judgement — but in learning.

If it was worth doing, what made it succeed?
If it wasn’t, what signals did we miss?
What should we repeat next time — and what should we avoid?

Without asking this, the organisation pays twice: once in effort, and again in ignorance.

Reflection is not a private act

Reflection that happens only in leadership meetings is incomplete.

The people who did the work must be part of the inquiry.

Including teams in reflection does two things. First, it surfaces insight that leaders alone will never see. Second, it honours the effort people gave — even if the outcome was disappointing.

When reflection is skipped, teams experience silence as dismissal. The work disappears, and so does any sense that learning mattered.

Leaders sometimes move on quickly to save face.

In doing so, they guarantee the same mistakes will be repeated.

Preventing wasted work before it starts

The most effective place to stop wasted effort is before momentum builds.

Henry James’ questions can be reframed as a simple pre-flight check for work:

What problem are we actually trying to solve?
How will we know if we’ve solved it?
Is this problem worth solving at all?

These questions do not slow work down. They prevent work that should never begin.

They force clarity of purpose. They surface hidden assumptions. They expose initiatives driven by fashion, pressure, or optimism rather than need.

Most importantly, they protect people’s time, energy, and attention — the scarcest resources in any organisation.

Reflection as an ability

Reflection is often treated as an event: a retrospective, a post-mortem, a lessons-learned session.

In reality, it is an ability.

Teams that reflect well learn faster. They abandon bad ideas earlier. They repeat good patterns deliberately. Over time, they build judgement and taste — not just activity.

Sometimes reflection leads to an uncomfortable conclusion:

No — it wasn’t worth doing.

That answer is not failure. Failing to learn from it is.

When organisations normalise reflection, wasted work decreases not because people try harder, but because they choose more carefully.

And when effort consistently turns into learning or value, work starts to feel meaningful again.

That is how ideas stop evaporating — and begin to matter.